WO2013018928A1 - Fused heterocyclic compound and use thereof for pest control - Google Patents

Fused heterocyclic compound and use thereof for pest control Download PDF

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Publication number
WO2013018928A1
WO2013018928A1 PCT/JP2012/070409 JP2012070409W WO2013018928A1 WO 2013018928 A1 WO2013018928 A1 WO 2013018928A1 JP 2012070409 W JP2012070409 W JP 2012070409W WO 2013018928 A1 WO2013018928 A1 WO 2013018928A1
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Prior art keywords
group
optionally substituted
halogen atoms
group optionally
atom
Prior art date
Application number
PCT/JP2012/070409
Other languages
French (fr)
Inventor
Masaki Takahashi
Takamasa Tanabe
Mai Ito
Yoshihiko Nokura
Atsushi Iwata
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to CA2844241A priority Critical patent/CA2844241C/en
Priority to AU2012290923A priority patent/AU2012290923B2/en
Priority to ES12751378T priority patent/ES2571488T3/en
Priority to MX2014000556A priority patent/MX366942B/en
Priority to RU2014108038A priority patent/RU2606119C2/en
Priority to BR112014001175-3A priority patent/BR112014001175B1/en
Priority to US14/234,717 priority patent/US9018134B2/en
Priority to KR1020147005753A priority patent/KR101840511B1/en
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to CN201280037185.2A priority patent/CN103717598B/en
Priority to EP12751378.6A priority patent/EP2739624B1/en
Publication of WO2013018928A1 publication Critical patent/WO2013018928A1/en
Priority to ZA2013/09160A priority patent/ZA201309160B/en
Priority to IL229835A priority patent/IL229835A/en
Priority to US14/669,492 priority patent/US9120823B2/en
Priority to US14/801,978 priority patent/US9353110B2/en
Priority to IL243374A priority patent/IL243374A/en
Priority to US15/041,097 priority patent/US9403771B2/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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • 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
    • C07D213/81—Amides; Imides
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to a fused heterocyclic compound and the use thereof for pest control.
  • Patent Literature 1 JP-A-2004-3 438
  • the present invention includes the followings:
  • A represents -NR -, an oxygen atom or a sulfur atom
  • R 1 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y,
  • R 2 , R 3 and R 4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR 10 , -S(0) m R 10 , -S (0 ) 2 NR 10 R 1:L , - NR 10 R , -NR 10 CO 2 R 11 , -NR 10 C (0 ) R 11 , -C0 2 R 10 , -C(0)R 10 , C(O)NR 10 R 1:i" , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 5 and R 6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR 10 , -S(0) m R 10 , -S (0 ) 2 NR 10 R U , - NR 10 R , -NR 10 C02R U , -NR 10 C (0 ) R 11 , -C0 2 R 10 , -C(0)R 10 , C(O)NR 10 R 1:L , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom (wherein R 5 and R 6 do not represents a hydrogen atom at the same time), R 7 represents a C1-C6 chain hydrocarbon group
  • R 8 and R 9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen, atoms, -OR 10 , -S(0) m R 10 , -NR 10 R n , -C0 2 R 10 , - C(0)R 10 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 10 and R 11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom,
  • each m independently represents 0, 1 or 2
  • n 0, 1 or 2
  • Group X the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one.
  • halogen atoms a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more .
  • halogen atoms a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups, a cyano group, a hydroxy group and a halogen atom,
  • Group Y the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms and a halogen atom,
  • Group Z the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group optionally substituted
  • Group W the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfInyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optional
  • the present compound or an N-oxide thereof (hereinafter referred to as "the present compound”) .
  • a 1 is -NR 7 -, an oxygen atom or a sulfur atom,
  • R 1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X,
  • R 2 , R 3 and R 4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR 10 , -S(0) m R 10 , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 5 and R 6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR 10 , S(0) m R 10 , -SF 5 , a halogen atom or a hydrogen atom
  • R 7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is- optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), or a hydrogen atom,
  • R is a C1-C6 chain hydrocarbon group ' optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom, and
  • R 9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom.
  • a 1 is -NR 7 -, an oxygen atom or a sulfur atom,
  • R 1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl group) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2 and. R 4 are the same or different each other and each represents a halogen atom or a hydrogen atom
  • R 3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen, atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR 10 , -S(0) m R 10 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 5 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , -SF 5 or a halogen atom
  • R 6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom
  • R 10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • R 7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a . C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or ' groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms, R is a C1-C6
  • R 9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom.
  • a la represents -NR 7a -, an oxygen atom or a sulfur atom,
  • R la represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R a and R 4a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) , -OR 20a (wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21a (wherein R 21a represents a C1-C6 al
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 2 a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 2 a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms)
  • -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1
  • n 0, 1 or 2
  • R la is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups),
  • R 2 and R 4a both are a. hydrogen atom
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen
  • R 5a is a C1-C6 haloalkyl group
  • -OR 2a wherein R 22a is a Cl- C6 haloalkyl group
  • -S(0) m R 23a (wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF 5 or a halogen atom, and
  • R 7a is a " C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one .
  • atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) .
  • R lb represents an ethyl group or a cyclopropylmethyl group
  • R 7 represents methyl group or a propargyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21b (wherein R 21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, . m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b (wherein R 22b represents a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF 5 or a halogen atom, and
  • n 0, 1 or 2
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b (wherein R 2 represents a C1-C6 haloalkyl group)
  • -S(0) m R 23 (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF 5 or a halogen atom, and
  • n 0, 1 or 2
  • R lb represents an ethyl group or a cyclopropylmethyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m Fr iD (wherein R 1b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 5b represents a C1-C6 haloalkyl group,.
  • -OR 22b (wherein R 22 represents a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2 ) , -SF5 or a halogen atom, and
  • n 0, 1 or 2
  • R represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms
  • R la represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2a and R 4a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and .
  • a C1-C3 alkoxy group optionally substituted by one or more halogen atoms a C1-C3 alkoxy group optionally substituted by one or more halogen atoms
  • -OR 20a wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21a (wherein R 21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 2a wherein R 22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 23a wherein R 23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF 5 or a halogen atom
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms)
  • -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2)
  • n .0, ,1 or 2
  • a pest control composition comprising a compound according to any one of the above [1] to [ 18] and an inert carrier .
  • a method for controlling a pest which comprises applying an effective amount of the compound according to any one of the above [1] to [ 18] to the pest or a habitat of the pest.
  • a la represents -NR 7a -, an oxygen atom or a sulfur atom
  • R a represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is . optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,.
  • - R 2a and R 4a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group Optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 .
  • R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2
  • R 5a represents a C1-C6 alkyl group, optionally substituted by one or more halogen atoms
  • -OR 22a (wherein R 2a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 3a (wherein R 23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2)
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , a halogen atom or a hydrogen atom,
  • n 0, 1 or 2
  • V 2 represents a halogen atom
  • A represents -NR -, an oxygen atom or a sulfur atom
  • R 2a and R a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted, by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered.
  • aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR 20a (wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R 5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 22a (wherein R 22a represents a C1-C6 alkyl group optionally substituted
  • R 7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is.
  • halogen atom optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and -
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms )
  • -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • V 2 represents a halogen atom
  • a la represents -NR 7a -, an oxygen atom or a sulfur atom,
  • R 2a and R 4a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or ⁇ -membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) , -OR 20a (wherein n
  • R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21a (wherein R 21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R 5a represents a C1-C6 alkyl .
  • R 22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 23a represents a C1-C6 .
  • R 7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the .5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and R
  • the present compound has an excellent controlling effect on pests and is useful as 1 an active ingredient of a pest control agent.
  • N-oxide in the present . compound means a compound wherein a nitrogen atom constituting a ring in a heterocyclic group is oxidized.
  • heterocyclic group which can form the N-oxide in the present compound include a pyridine ring.
  • the "Ca-Cb chain hydrocarbon group” means a linear or branched, saturated or unsaturated hydrocarbon group having a to b carbon atoms;
  • the "Ca-Cb alkyl group” means a linear or branched hydrocarbon group having a to b carbon atoms;
  • Ca-Cb alkenyl group means a linear or branched, unsaturated hydrocarbon group having a to b carbon atoms and one or more double bonds within the molecule;
  • Ca-Cb alkynyl group means a linear or branched, unsaturated hydrocarbon group having a to b carbon atoms and one or more triple bonds within the molecule;
  • the "Ca-Cb haloalkyl group” means a linear or branched alkyl group having a to b carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are substituted by one or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other;
  • the Ca-Cb alkoxy group means a linear or branched alkyl-O-group having a to b carbon atoms;
  • Ca-Cb alkenyloxy group means a linear or branched alkenyl-O-group having a to b carbon atoms and one or more double bonds within the molecule;
  • Ca-Cb alkynyloxy group means, a linear or branched alkynyl-O-group having a to b carbon atoms and one or more triple bonds within the molecule;
  • Ca-Cb alkylsulfanyl group means a linear or branched alkyl-S-group having a to b carbon atoms
  • Ca-Cb alkylsulfinyl group means a linear or branched alkyl-S (0 ) -group having a to b carbon atoms;
  • Ca-Cb alkylsulfonyl group means a linear or branched alkyl-S (0 ) 2 -group having a to b carbon atoms;
  • Ca-Cb alkyl carbonyl group means a linear or branched alkyl-C (0 ) -group having a to b carbon atoms;
  • Ca-Cb alkoxycarbonyl group means a linear or branched alkyl-O-C (0 ) -group having a to b carbon atoms;
  • the "Ca-Cb alicyclic hydrocarbon group” means a cyclic nonaromatic hydrocarbon group having a to b carbon atoms
  • the "Ca-Cb cycloalkyl group” means a cyclic alkyl group having a to b carbon atoms
  • Ca-Cb alkylamino group means a linear or branched alkyl-NH-group having a to b carbon atoms
  • Ca-Cb dialkylamino group means a linear or branched dialkylamino group, wherein the alkyl groups have the same or different carbon atoms and the total number of carbon atoms is a to b;
  • Ca-Cb alkoxyalkyl group means a linear or branched alkyl-0-alkyl group, wherein the alkyl groups have the same or different carbon atoms and the total number of carbon atoms is a to b.
  • the "halogen atom" in the present compound includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X" in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one or more atoms or groups selected from Group X, and when the group is substituted by two or more atoms or groups selected from Group X, these atoms or groups are the same or different from each other.
  • Examples of the "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X" in the present compound include Cl- C6 alkyl groups optionally substituted by one or more atoms or groups selected from Group X, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl ⁇ group, a pentyl group, a neopentyl group, a hexyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert- butyloxymethyl group, a 2-methoxyethyl group, a 2- ethoxyethyl group,
  • C2-C6 alkenyl groups optionally substituted by one or more atoms or groups selected from Group X, such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-l-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like; and
  • C2-C6 alkynyl groups optionally substituted by one or more atoms or groups selected from Group X, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group and a 4,4,4- trifluoro-2-butynyl group, and the like; which is selected depending on a given range of carbon atoms.
  • Group X such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group and a 4,4,4- trifluoro-2-butynyl group, and the like; which is selected depending on a given range of carbon atoms.
  • the "C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y" in the present compound means a cyclic non- aromatic hydrocarbon group having 3 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom ( s ) is/are optionally substituted by one or more atoms or groups selected from Group Y, and when the group is substituted by two or more atoms or groups selected from Group Y, these atoms or groups are the same or different from each other.
  • Examples of the "C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y" in the present compound include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2- cyclohexenyl group, a 3-cyclohexenyl group, a 1- methylcyclohexyl group, a 2-methylcyclohexyl group, a 3- methylcyclohexyl group, a -methylcyclohexyl group, a 2- methoxycyclohexyl group, a 3-methoxycyclohexyl group, a 4- methoxycyclohexyl group, a 1-fluorocyclohexyl group, a 2- fluorocyclohexyl group, a 3-fluorocyclohexyl group, and
  • the "C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms" in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one . or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other.
  • Examples of the "C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms" in the present compound include C1-C6 alkyl groups optionally substituted by ⁇ one or more halogen atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2 , 2-difluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, and the like;
  • C2-C6 alkenyl groups optionally substituted by one or more halogen, atoms such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-l- propenyl group, a 1-butenyl group, a 2-butenyl group, a 3- butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like; C2-C6 alkynyl groups optionally substituted by one or more halogen atoms such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a l-pentynyl group, a 1-hexynyl group, a 4 , 4 , 4-trifluoro-2-butyn
  • phenyl group optionally substituted by one or more atoms or groups selected from Group Z in the present compound means a phenyl group, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one or more atoms or groups selected from Group Z, and when the group is substituted by two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
  • Examples of the "phenyl group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound include a phenyl group, a 2- fluorophenyl group, a 3-fluorophenyl group, a 4- fluorophenyl group, a 2 , 3-difluorophenyl group, a 2,4- difluorophenyl group, a 2 , 5-difluorophenyl group, a 2,6- difluorophenyl group, a 3 , -difluorophenyl group, a 3,5- difluorophenyl group, a 2 , 3 , 4 , 5 , 6-pentafluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4- chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4 -bromophenyl group
  • heterocyclic group in the present compound means a residue of a heterocyclic compound having one or more nitrogen atoms, oxygen atoms or sulfur atoms in addition to carbon atoms in the ring structure.
  • the "5-membered heterocyclic group” in the present compound means a 5-membered aromatic heterocyclic group or 5-membered non-aromatic heterocyclic group
  • the "6- membered heterocyclic group” means a 6-membered aromatic heterocyclic group or a. 6-membered non-aromatic heterocyclic group.
  • heterocyclic group in the "5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound means a residue of a heterocyclic compound having one or more nitrogen atoms, oxygen atoms or sulfur atoms in addition to carbon atoms in the ring structure, wherein the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
  • the "5- or 6-membered heterocyclic group" in the present compound means a 5- or ⁇ -membered aromatic heterocyclic group, or a 5- or 6-membered non-aromatic heterocyclic group.
  • Examples of the "5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound include 5 or 6-membered non-aromatic heterocyclic groups optionally substituted by one or more atoms or groups selected from Group Z, such as a pyrrolidin-l-yl group, a 3,3,4,4- tetrafluoropyrrolidin-l-yl group, a tetrahydrofuran-2-yl group, a piperidyl group, a morpholyl group, a thiomorpholyl group, and the like;
  • 5- or 6-membered aromatic heterocyclic groups optionally substituted by one or more atoms or groups selected from Group Z, such as a 2-pyrroly group, a 2-furyl group, a 3- furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1- pyrroly group, a l-methyl-2-pyrroly ' group, a 2- methylsulfanyl-l-pyrroly group, a 2-methylsulfinyl-1- pyrroly.
  • Group Z such as a 2-pyrroly group, a 2-furyl group, a 3- furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1- pyrroly group, a l-methyl-2-pyrroly ' group, a 2- methylsulfanyl-l-pyrroly group, a 2-methylsulfinyl-1- pyrroly.
  • Examples of the "C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z) " in the present compound include a phenylmethyl group, a 4 -chlorophenylmethyl group and a 4- trifluoromethyl phenylmethyl group, and the like. When the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
  • Examples of the "C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z ) " in the present compound include 5 or 6-membered non-aromatic heterocyclic groups such as a tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2- ylmethyl group, a tetrahydropyran-3-ylmethyl group, and the like;
  • 5- or 6-membered aromatic heterocyclic groups such as a thiazol-5-ylmethyl group, a 2-chlorothiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3- ylmethyl group, a 6-trifluoromethylpyridin-3-ylmethyl group, and the like.
  • the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
  • Examples of the "5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyrroly group, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrroly group, a l-methyl-2-pyrroly group, a 5- bromo-2-furyl group, a 5-methoxy-2-furyl group, a 2-methyl- 3-furyl group, a 2 , 5-dimethyl-3-furyl group, a 2,4- dimethyl-3-furyl group, a 5-methyl-2
  • C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups)
  • the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups
  • examples of the "C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups)" in the present compound include a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, an
  • Examples o "the "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W” in the present compound include Cl- C6 alkyl groups optionally substituted by one or more atoms or groups selected from Group W, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2 , 2-difluoroethyl group, a 2,2,2- trifluoroethyl group, a pentafluoroethyl group, a methoxymethyl group, an ethoxymethyl group, a prop
  • C2-C6 alkenyl groups optionally substituted by one or more atoms or groups selected from Group W, such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1- methylvinyl group, a 2-methyl-l-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, pentafluoroallyl group, and the like;
  • Group W such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1- methylvinyl group, a 2-methyl-l-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-
  • C2-C6 alkynyl groups optionally substituted by one or more atoms or groups selected from Group W, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4,4,4- trifluoro-2-butynyl group, and the like.
  • Group W such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4,4,4- trifluoro-2-butynyl group, and the like.
  • Group W such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentyny
  • Examples of the "C1-C6 alkoxy group optionally substituted by one or more halogen atoms" in the present compound include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2 , 2 , 2-trifluoroethoxy group, .a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, and the like.
  • Examples of the "C2-C6 alkenyloxy group substituted by one or more halogen atoms" in the present compound include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2- butenyloxy group, a 3-butenyloxy group, a 2-pentenyloxy group, a 2-hexenyloxy group, a 3, 3-difluoroallyloxy group, a 3,3-dichloro allyloxy group, and the like.
  • Examples of the "C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms" in the present compound include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 2-hexynyloxy group, a 4 , 4 , -trifluoro-2-butynyl oxy group, and the like.
  • Examples of the "C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms" in the present compound include . a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl .
  • Examples of the "C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms" in the present compound include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2 , 2 , 2-trifluoroethylsulfinyl group, a pentafluoroethylsulfinyl group, and the like.
  • Examples of the "C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms" in the present compound include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2 , 2 , 2-trifluoroethylsulfonyl group, a pentafluoroethylsulfonyl group, and the like.
  • C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms examples include an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, a hexanoyl group, a trifluoroacetyl group, and the like.
  • Examples of the "C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms" in the present compound include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a pentyloxycarbonyl group, a tert-butyloxycarbonyl group, a 2 , 2 , 2-trifluoroethyloxycarbonyl group, and the like.
  • Examples of the "C1-C6 alkylamino group optionally substituted by one or more halogen atoms" in the present compound include a methylamino group, an ethylamino group, a 2 , 2 , 2-trifluoroethylamino group, a propylamino group, an isopropylamino group, a butylamino group, and the like.
  • Examples of the "C2-C8 dialkylamino group optionally substituted by one or more halogen atoms" in the present compound include a dimethylamino group, a diethylamino group, a bis ( 2 , 2 , 2-trifluoroethyl ) amino group, a dipropylamino group, and the like.
  • Examples of the "C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms" in the present compound include a cyclopropyl group, a 2,2- difluorocyclopropyl group, a 2 , 2-dichlorocyclopropyl group, a 2 , 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
  • Examples of the "C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more Cl- C3 . alkyl groups" in the present compound include a cyclopropyl group, a 1-methylcyclopropyl group, a 2- methylcyclopropyl group, a 1-fluorocyclopropyl group, a 2 , 2-difluorocyclopropyl group, a 2 , 2-dichlorocyclopropyl group, a 2 , 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
  • C2-C6 alkyl group examples include an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, and the like.
  • C1-C6 haloalkyl group in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are substituted by one or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other.
  • Examples of the "C1-C6 haloalkyl group" in the present compound include a fluoro methyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group-, a bromodifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2 , 2-difluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, and the like.
  • Examples of the "C4-C9 cyclopropylalkyl group (wherein the cyclopropyl ⁇ group is optionally substituted by one or more halogen atoms or one or more Cl-C.3 alkyl groups)" in the present compound include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a 1-cyclopropylethyl group, a 1- methylcyclopropyl group, and the like.
  • C1-C6 perfluoroalkyl group examples include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, and the like.
  • Examples of the "C1-C6 alkyl group optionally substituted by one or more halogen atoms" in the present compound include a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2
  • Examples of the "C2-C6 alkenyl group optionally substituted by one or more halogen atoms" in the present compound include a vinyl group, a 1-propenyl group, a 2- propenyl group, a 1-methyl vinyl group, a 2-methyl-l- propenyl group, a 1-butenyl group., a 2-butenyl group, a 3- butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1, 1-difluoroallyl group, a pentafluoroallyl group, and the like .
  • Examples of the "C2-C6 alkynyl group optionally substituted by one or more halogen atoms" in the present compound include an ethynyl group, a propargyl group, a 2- butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1- hexynyl group, a 4 , , 4-trifluoro-2-butynyl group, and the like.
  • Examples of the "C3-C6 alkenyl group optionally substituted by one or more halogen atoms" in the present compound include a 1-propenyl group, a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-l-propenyl group, a 1- butenyl group, a 2-butenyl group, a 3-butenyl group, a 1- pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like.
  • Examples of the "C3-C6 alkynyl . group optionally substituted by one or more halogen atoms" in the present compound include a propargyl group, a 2-butynyl group, a 3- butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4 , 4 , 4-trifluoro-2-butynyl group, and the like.
  • Examples of the "C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms" in the present compound include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, a 2- (methoxy) ethyl group, a 1- (ethoxy) ethyl group, a 2- (ethoxy) ethyl group, a 2,2,2- trifluoroethoxymethyl group, and the like.
  • Examples of the "pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 5-trifluoromethyl-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, and the like.
  • Examples of the "pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyrimidinyl group, a 4- pyrimidinyl group, a 5-pyrimidinyl group, a 2-chloro-4- pyrimidinyl group, and the like.
  • Examples of the present compound include the following compounds: A compound represented by the formula (1-1) :
  • a la represents -NR 7a -, an oxygen atom or a sulfur atom,
  • R l represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2a and R 4a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one " or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a.
  • R 5a represents a C1-C6 alkyl group optionally substituted
  • halogen atoms by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 23a (wherein R 23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
  • R 7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atom, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms),
  • R 9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 2 a wherein R 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 25 wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • n 0, 1 or 2
  • R lb represents an ethyl group or a ' cyclopropylmethyl group
  • R 7b represents methyl group or a propargyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20b wherein R 20b represents a C1-G6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21b (wherein R 21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b (wherein R 22b represents a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF 5 or a halogen atom, and
  • n 0, 1 or 2
  • R l represents an ethyl group or a ' cyclopropylmethyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 1b wherein R 21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b represents a C1-C6 haloalkyl group
  • -S(0) m R 23b wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom,
  • n 0, 1 or 2
  • R lb represents an ethyl group or a cyclopropylmethyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20b wherein R 20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21b wherein R 21b represents a C1-C6 alkyl group optionally, substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b (wherein R 22b represents a C1-C6 haloalkyl group), -S(0) m R 3b (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF 5 or a halogen atom, and
  • n 0, 1 or 2
  • R a represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms
  • R la represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2a and R a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms ) , -OR 20a (wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21a (wherein R 21a represents a C1
  • R 5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 22 .
  • R 22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 23a (wherein R 23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF 5 or a halogen atom,
  • R a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • m represents 0, 1 or 2
  • n 0, 1 or 2
  • R 70a is a hydrogen atom or a C2-C6 alkoxyalkyl group
  • R la is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2a and R a are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR 20a (wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21a (wherein R 21a represents a C1-C6 alky
  • R 5a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 22a (wherein R 22 represents a C1-C6 alkyl group optionally substituted by one or more ' halogen atoms), _-S(0) m R 23a (wherein R 23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
  • R 9a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted ' by one or more halogen atoms), -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom
  • R 9a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 24a (wherein R 24a represents a C1-C6 alkyl group optionally substituted ' by one or more halogen atoms)
  • -S(0) m R 25a (wherein R 25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents
  • n 0, 1 or 2
  • R 70b represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms,
  • R lb represents an ethyl group or a cyclopropylmethyl group
  • R 3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21b (wherein R 21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a halogen atom or a hydrogen atom
  • R 5b represents a C1-C6 haloalkyl group
  • -OR 22b (wherein R 22b represents a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
  • n 0, 1 or 2
  • a compound represented by the formula (1) wherein A 2 R 8 -, and A 3 is a nitrogen atom;
  • a compound represented by the formula (1) wherein A 2 R 8 -, and A 3 is CR 9 -;
  • a compound represented by the formula (1) wherein A 1 R 7 -, and A 2 is CR 8 -;
  • a compound represented . by the formula (1) wherein A 1 R 7 -, A 2 is CR 8 -, and A 3 is a nitrogen atom;
  • a compound represented by the formula (1) wherein A 1 oxygen atom, and A 2 is CR 8 -;
  • a compound represented by the formula (1) wherein A 1 is an oxygen atom, A 2 is CR 8 -, and A 3 is a nitrogen atom;
  • a compound represented by the. formula (1) wherein A 1 is a sulfur atom, and A 2 is CR 8 -;
  • a compound represented by the formula (1) wherein A 1 is a sulfur atom, A 2 is CR 8 -, and A 3 is a nitrogen atom;
  • R 1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X;
  • R 1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms;
  • R 3 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group .
  • Z a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR 10 , -S(O) m R X0 , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom;
  • R 3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a .
  • a compound represented by the formula (1) wherein R 5 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR 10 , -S(0) m R 10 , -SF 5 , a halogen atom or . a hydrogen atom;
  • a halogen atom selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms
  • a C1-C6 alkyl group substituted by one 6-membered aromatic heterocyclic group wherein the 6- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms
  • a halogen atom a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen
  • a compound represented by the formula (1) wherein when A 2 is CR 8 -, R 8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 2 is CR 8 -, R 8 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 (wherein R 10 is a C1-C6 alkyl group optionally substituted by one. or more halogen atoms), -S(0) m R 10 (wherein R 10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 2 is CR 8 -, R 8 is a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 2 is CR 8 -, R 8 is a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 3 is CR 9 -, R 9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 (wherein R 10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 10 (wherein R 10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), a halogen atom or a hydrogen atom; [ 0061]
  • R 1 is a C1-C6. alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-.C3 alkyl groups);
  • R 1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R 1 is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R 1 is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
  • R 1 is an ethyl group or a cyclopropylmethyl group
  • a compound represented by the formula (1) wherein R 1 is an ethyl group;
  • a compound represented by the formula (1) wherein R 3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the
  • R 3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20b wherein R 0b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21b wherein R 21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
  • a 2- pyridyl group a 5-trifluoromethyl-2-pyridyl group, a 2- pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • R 5 is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF 5 or a halogen atom;
  • R 5 is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a C1-C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
  • R 5 is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a C1-C6 haloalkyl group), -S(0) m R 23b (wherein . R 23b is a . C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
  • R 5 is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a C1-C6 haloalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
  • R 5 is a C1-C6 perfluoroalkyl group, -OR 10 (wherein R 10 is a Cl- C6 perfluoroalkyl group) or -S(0) m R 10 (wherein R 10 is a Cl- C6 perfluoroalkyl group) ;
  • a compound represented by the formula (1) wherein when A 3 is CR 9 -, R 9 is a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 3 is CR 9 -, R 9 is a fluorine atom, a chlorine atom, a bromine atom, an iodine ' atom or a hydrogen atom;
  • a compound represented by the formula (1) wherein when A 3 is CR 9 -, R 9 is a fluorine atom or a hydrogen atom;
  • R 1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X,
  • R 2 , R 3 and R 4 are the same or different each other and each represents a C1-C6 ' chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected, from Group Z, -OR 10 , -S(0) m R 10 , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom, R 5 and R 6 are the same or different each other and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR 10 , -S(0) ra R 10 , -SF 5 a halogen
  • R 7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5-membered heterocyclic group (wherein the 5-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) , a C1-C6 chain hydrocarbon group substituted by one 6-membered heterocyclic group (wherein the 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) or a hydrogen atom,
  • R 8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom,
  • R 9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom.
  • R 1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
  • R 2 and R 4 are the same or different each other and each represents a halogen atom or a hydrogen atom
  • R 3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), 6-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more hal
  • R 5 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , -SF 5 or a halogen atom
  • R 6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom
  • R 10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • R 7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- membered.
  • aromatic heterocyclic group (wherein the 5- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a C1-C6 alkyl group substituted by one 6-membered aromatic heterocyclic group (wherein the 6- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group,
  • R 8 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(Q) m R 10 , a halogen atom or a hydrogen atom,
  • R 9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , a halogen atom or a hydrogen atom.
  • a la is -NR 7a - , and A 3a is a nitrogen atom;
  • a compound represented by the formula (1-1) wherein A la is -NR 7a - , and A 3a is CR 9a - compound;
  • a compound represented by the formula (1-1) wherein A la is an oxygen atom, and A 3a is CR 9a - compound;
  • R l is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R la is a C1-C6 -alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R la is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R la is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
  • R la is an ethyl group
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -OR 20a wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21a wherein R 21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
  • R 3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF 2 CF 3 , - C F2C F2C F3 , -CF(CF 3 ) 2 , -CF 2 CF 2 CF 2 CF3, -OCF3, -OCF 2 CF 3 , -SCF3, -S(0)CF 3 , -S(0) 2 CF 3 , -SCF2CF3, -S(0)CF 2 CF 3 , S(0) 2C F 2 C F3 , a 2-pyridyl group, a 5-trifluoromethyl-2- pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom
  • R 5a is a C1-C6 haloalkyl group, -OR 22a (wherein R 22a is a Cl- C6 haloalkyl group), -S(0) m R 23a (wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF 5 or a halogen atom;
  • R 5a is a C1-C6 haloalkyl group
  • -OR 22a wherein R 22a is a Cl- C6 haloalkyl group
  • -S(0) m R 23a wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
  • R 5a is a C1-C6 haloalkyl group, -OR 2a (wherein R 22a is a Cl- C6 haloalkyl group), -S(0) m R 3a (wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
  • R 5 is a trifluoromethyl group., -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S(0)CF 3 , -S(0) 2 CF 3 , -SCF 2 CF 3 , - S(0)CF 2 CF 3 , -S (0) 2 CF 2 CF 3 , SF 5 , a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
  • a compound represented by the formula (1-1) wherein when A 3a is CR 9a -, R 9a is a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1-1) wherein when A 3a is CR 9a -, R 9a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the formula (1-1) wherein when. A 3a is CR 9a -, R 9a is a fluorine atom or a hydrogen atom;
  • a compound represented by the formula (1-2) wherein A is CR - compound;
  • R 3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, .
  • a trifluoromethyl group - CF 2 CF 3 , -CF2CF2CF3, -CF(CF 3 ) 2 , -C F2C F2C F2C F3 , -OCF3, -OCF 2 CF 3 , -SCF 3 , -S(0)CF 3 , -S(0) 2 CF 3 , -SCF 2 CF 3 , -S(0)CF 2 CF 3 , S(0)2CF 2 CF 3 , a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group) , -S (0 ) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5. or a halogen atom;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23 (wherein R 23b is a C1-C6 haloalkyl group, and m is 0,.1 or 2) or -SF5;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 2b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
  • R 5 is a G1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- G6 haloalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
  • R 5b is a C1-C6 perfluoroalkyl group, -OR 22b (wherein R 22b is a C1-C6 perfluoroalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 perfluoroalkyl group) ;
  • R 5b is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S(0)CF 3 , -S(0) 2 CF 3 , -SCF 2 CF 3 , - S(0)CF 2 CF 3 , -S (0) 2 CF 2 CF 3 , SF 5 , a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
  • a compound represented by the formula (1-2) wherein when A 3b is CR 9b -, R 9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the formula (1-2) wherein when A 3b is CR 9b -, R 9 is a fluorine atom or a hydrogen atom;
  • a compound represented by the formula (1-3) wherein A 3b is CR 9b - compound; [ 0077]
  • R 3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF 2 CF 3 , -CF2CF2CF3, -CF(CF 3 ) 2 , -C F2C F2C F2C F3 , -OCF3, -OCF 2 CF 3 , -SCF3, -S(0)CF 3 , -S(0) 2 CF 3 , - SC F2C F3 , -S(0)CF 2 CF 3 ,
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF 5 ;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b .is a Cl- C6 haloalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
  • R 5b is a C1-C6 perfluoroalkyl group, -OR 22b (wherein R 22b is a C1-C6 perfluoroalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 perfluoroalkyl group) ;
  • R 5b is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S(0)CF 3 , -S(0) 2 CF 3 , -SCF 2 CF 3 ,
  • a compound represented by the formula (1-3) wherein when A 3b is ' CR 9b -, R b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the formula (1-3) wherein when A 3b is CR 9b -,.. R 9b is a fluorine atom or a hydrogen atom;
  • a compound represented by the formula (1-4) wherein A 3b is CR 9b - compound;
  • R 3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF 2 CF 3 , -C F2C F2C F3 , -CF(CF 3 ) 2 , - C F2C F2C F2C F3 , -O C F3 , -OCF 2 CF 3 , -SCF3, -S(0)CF 3 , -S(0) 2 CF 3 , - SC F2C F3 , -S(0)CF 2 CF 3 , - S(0) 2C F2C F 3 , a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0.) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF 5 or a halogen atom;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
  • R 5 is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
  • R 5b is a C1-C6 perfluoroalkyl group, -OR 22b (wherein R 22b is a C1-C6 perfluoroalkyl group) or -S(0) ffi R 23b (wherein R 23b is a C1-C6 perfluoroalkyl group) ;
  • R 5b is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -OCF 3 , -OCF 2 CF 3 , -SCF 3 , -S(0)CF 3 , -S(0) 2 CF 3 , -SCF 2 CF 3 ,
  • a compound represented by the formula (1-4) wherein when A 3b is CR 9b -, R 9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the formula (1-4) wherein when A 3b is CR 9b -, R 9b is a fluorine atom or a hydrogen atom;
  • a 3a is a nitrogen atom
  • a compound represented by the formula (1-5) wherein A 3a is CR 9a - compound;
  • R is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups) ;
  • R la is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R la is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
  • R la is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
  • R la is an ethyl group or a cyclopropylmethyl. group
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 al
  • halogen atoms or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms
  • -OR 20a wherein R 20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • -S(0) m R 21a wherein R 21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom;
  • R 3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR 20a (wherein R 20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0) m R 21a (wherein R 1a . represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
  • R 3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, -CF2CF2CF3, -CF(CF 3 ) 2 , -CF2CF2CF2CF3, -OCF 3 , -OCF2CF3, -SCF3, -S(0)CF 3 , -S(0) 2 CF 3 , -SCF2CF3, -S(0)CF 2 CF 3 , S(0) 2 CF 2 CF 3 , a fluorine atom, a chlorine atom, a bromine atom, art iodine atom or a hydrogen atom;
  • R 5a is a C1-C6 haloalkyl group, -OR 22a (wherein R 22a is a Cl- C6 haloalkyl group), -S(0) m R 23a (wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
  • R 5a is a C1-C6 haloalkyl group, -OR 22a (wherein R 2 a is a Cl- C6 haloalkyl group), -S(0) m R 23a (wherein R 23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
  • R a is a C1-C6 haloalkyl group, -OR 22 (wherein R 22a is a Cl- C6 haloalkyl group) or -S(0) m R 23 (wherein R 23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
  • R 5a is a C1-C6 perfluoroalkyl group, -OR 2a (wherein R 22a is a C1-C6 perfluoroalkyl group) or -S(0) m R 23a (wherein R 3a is a C1-C6 perfluoroalkyl group) ;
  • R 70a is a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group;
  • a compound represented by the formula (1-5) wherein when A 3a is CR 9a -, R 9a is a halogen atom or a hydrogen atom; ⁇
  • a compound represented by the formula (1-5) wherein when A 3a is CR 9a -, R 9a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the. formula (1-5) wherein when A 3 is CR 9a -, R 9a is a fluorine atom or a hydrogen atom;
  • R 3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF 3 , -CF2CF 2 CF 3 , -CF(CF 3 ) 2 , .
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF 5 or a halogen atom;
  • R 5b is a C1-C6 haloalkyl group
  • -OR 22b wherein R 22b is a Cl- C6 haloalkyl group
  • -S(0) m R 23b wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF 5 ;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group), -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2 ) or a halogen atom;
  • R 5b is a C1-C6 haloalkyl group, -OR 22b (wherein R 22b is a Cl- C6 haloalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
  • R 5b is a Cl-C-6 perfluoroalkyl group, -OR 22 (wherein R 22b is a C1-C6 perfluoroalkyl group) or -S(0) m R 23b (wherein R 23b is a C1-C6 perfluoroalkyl group) ;
  • R 5b is a trifluoromethyl group, -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -OCF3, -OCF2CF3, -SCF3, -S(0)CF 3 , -S(0) 2 CF 3 , -SCF2CF3, - S(0)CF 2 CF 3 , -S (0) 2 CF 2 CF 3 , SF 5 , a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;.
  • R 70b is a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group;
  • a compound represented by the formula (1-6) wherein when A 3b is CR 9b -, R 9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
  • a compound represented by the formula (1-6) wherein when A 3b is CR 9b -, R 9b is a fluorine atom or a hydrogen atom;
  • a fused heterocyclic compound represented by the formula ( 1-7 ) is represented by the formula ( 1-7 ) :
  • a c represents -NR c -, an oxygen atom or a sulfur atom
  • R represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X c or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y c ,
  • R 2c and R 4c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S(O) m R 10c , -NR 10c R llc , -CO 2 R 10c , -C(O)R 10c , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 3c represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z c , a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z c , a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z c , -OR 10c , -S(O) m R 10c , -NR 10c R llc , -CO 2 R 10c , -C(0)R c , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 5c and R 6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X c , a phenyl group optionally substituted by one or more atoms or groups selected from Group Z c , a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z c , a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z c , -OR 10c , -S(O) m R 10c , -S (0 ) 2 NR 10c R llc , - NR 10c R llc , -CO. 2 R 10c , -C(O)R 10c , -SF 5 , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 7c represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W c , -CO 2 R 10c , -C(O)R 10c , or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y c ,
  • R 8c and R 9c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S(O) m R 10c , -NR 10c R llc , -CO 2 R 10c , -C(O)R 10c , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
  • R 10c and R llc are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms or a hydrogen atom,
  • n 0, 1 or 2
  • n 0, 1 or 2.
  • R 5c and R 6c do not represents a hydrogen atom at the same time, and in the -S(O) m R 10c , R 10c does not a hydrogen atom when m is 1 or 2,
  • Group X c the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a hydroxy group and a halogen atom,
  • Group Y c the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms and a halogen atom,
  • Group Z c the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group
  • Group W c the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfony
  • a compound represented by the formula (1-7) wherein A 3c is a nitrogen atom or CR 9c -, and R 9c is a halogen atom or a hydrogen atom;
  • a compound represented by the formula (1-7) wherein A 2c is a nitrogen atom, A 3c is CR 9c -;
  • a compound represented by the formula (1-7) wherein A 2c is CR 8c -, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is -NR 7c -, A 2c is a nitrogen atom, A 3c is CR 9c -;
  • a compound represented by the formula (1-7) wherein A lc is -NR 7c -, A 2c is CR 8c -, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is -NR /C -, A 10 is CR -, R sc is a hydrogen atom, A JC is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is -NR 7c -, R 7c is a methyl group, and A 2c is CR 8c -, R 8c is a. hydrogen atom, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is an oxygen atom, and A 2c is a nitrogen atom, A 3c is CR 9c -;
  • a compound represented by the formula (1-7) wherein A lc is an oxygen atom, and A 2c is CR 8c -, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is an oxygen atom, and A 2c is CR 8c -, R 8 is a hydrogen atom, A 3c is a nitrogen atom;
  • a lc is an oxygen atom, and A 2c is a nitrogen atom, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A is a sulfur atom, and A is a nitrogen atom, A is CR 9c -;
  • a compound represented by the formula (1-7) wherein A lc is a sulfur atom, and A 2c is CR 8c -, A 3c is a nitrogen atom;
  • a compound represented by the formula (1-7) wherein A lc is a sulfur atom, and A 2c is CR 8c -, R 8c is a hydrogen atom, A 3c is a nitrogen atom;
  • R lc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • R lc is a C1-C6 alkyl group optionally substituted by one or more halogen atoms
  • R 2c .and R c are the same or different and each represents a hydrogen atom or a halogen atom
  • R 3c is a C1-C6 chain hydrocarbon group optionally substituted . by one or more halogen atoms., -OR 10c , a halogen atom or a hydrogen atom;
  • R 3c is a -C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a halogen atom or a hydrogen atom;
  • R 2c and R 4c both are a hydrogen atom
  • R 3c is a phenyl group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms, a 5-membered heterocyclic group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms or a 6-membered heterocyclic group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms;
  • R 2 , R 3c and R 4c is a hydrogen atom
  • R 5c and R 6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S (0 ) m R 10c , a halogen atom or a hydrogen atom;
  • R 5c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S(O) m R 10c or a halogen atom, R c is a hydrogen atom;
  • R 5c is a C1-C3 alkyl group substituted by one- or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, . a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfiny ' l group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom, R 6c is a hydrogen atom;
  • R lc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • R 2c and R 4c are the same or different and each represents a hydrogen atom or a halogen atom
  • R 3c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • -OR 10c a halogen atom or a hydrogen atom
  • R 5c and R 6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S(O) m R 10c , a halogen atom or a hydrogen atom
  • a lc is -NR 7c -
  • R 7c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group substituted by one
  • a 2c CR 8c -
  • R 9c is a halogen atom or a hydrogen atom
  • R lc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • R 2c and R 4c are the same or different and each represents a halogen atom or a hydrogen atom
  • R 3c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -S(O) m R 10c , a halogen atom or a hydrogen atom
  • R 5c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10c , -
  • a compound represented by the formula (1-7) wherein A lc is a sulfur atom, and A 2c is CR 8c -, R 8c is a hydrogen atom, A 3c is a nitrogen atom, R lc is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, R 2c and R 4c both are a hydrogen atom
  • R 3c is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, a halogen atom or a hydrogen atom
  • R 5c is a C1-C3 alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom
  • R is a hydrogen atom
  • R 3c is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom
  • R 5c is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, a bromine atom or an iodine atom
  • R 6c is a hydrogen atom
  • a fused heterocyclic compound represented by the formula ( 1-8 ) is represented by the formula ( 1-8 ) :
  • a ld represents -NR 7d - or a sulfur atom
  • R ld represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • R 2d and R d are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a halogen atom or a hydrogen atom
  • R 3d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10d , a halogen atom or a hydrogen atom
  • R 5d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10d , -S(O) m R 10d , a bromine atom or an iodine atom,
  • R 7d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • R 9d represents a halogen atom or a hydrogen atom
  • R 10d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms
  • n 0, 1 or 2
  • n 0, 1 or 2;
  • a compound represented by the formula (1-8) wherein A 3d is CR 9d -;
  • a compound represented by the formula (1-8) wherein A ld is -NR 7d - , and A 3d is CR 9d -;
  • a compound represented by the formula (1-8) wherein A ld is a sulfur atom, and A 3d is CR 9d -;
  • a ld is a sulfur atom, and A 3d is a nitrogen atom;
  • R 5d is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;
  • R 5d is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;
  • a compound represented by the formula (1-8) wherein A ld is -NR 7d - , and R 7d is a methyl group, and A 3d is CR 9d -, and R ld is an ethyl group, R 2d and R 4d are the same or different and each represents a halogen atom or a hydrogen atom, R 3d is a trifluoromethyl group, a halogen atom or a hydrogen atom, R 5d is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine
  • a compound represented by the formula (1-8) wherein A ld is -NR 7d - or a sulfur atom, R 7d is a methyl group, and A 3d is CR 9d -, and R ld is an ethyl group, R 2d and R 4d is a hydrogen atom, R 3d is a chlorine atom, a bromine atom, a trifluoromethyl group or a hydrogen atom, R 5d is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;
  • R 1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y,
  • R 2 , R 3 and R 4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a hydrogen atom,
  • R 5 and R 6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR 10 , S(0) m R 10 , -NR 10 R U , -C0 2 R 10 , -C (0) NR 10 R n , -SF 5 , a cyano group, a halogen atom or a hydrogen atom,
  • R 7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6- membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) or a hydrogen atom,
  • R 8 and R 9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR 10 , -S(0) m R 10 , -NR 10 R , a cyano group, a halogen atom or a hydrogen atom,
  • R 10 and . ' R 11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom,
  • each m independently represents 0, 1 or 2
  • n 0, 1 or 2;
  • the present compound and the intermediate compound thereof can be produced by, for example, the following (Production process 1) to (Production process 24).
  • the present compound represented by the formula (1) wherein n is 1 or 2 can be produced by oxidizing the present compound wherein n is 0.
  • the present compound represented by the formula (1-nl) wherein n is 1 can be produced by oxidizing the present compound (1-nO) wherein n is 0.
  • the oxidation reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include aliphatic halogenated ' hydrocarbons such- as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.
  • Examples of the oxidant to be used in the reaction include sodium periodate and m-chloroperbenzoic acid.
  • the amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the present compound (1-nO) .
  • the reaction temperature of the reaction is generally within a range of -20°C to 80°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 12 hours.
  • the present compound (1-nl) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, washing the organic layer with, optionally an agueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer.
  • a reduction agent e.g., sodium sulfite and sodium thiosulfate
  • a base e.g., sodium hydrogen carbonate
  • the present compound represented by the formula (l-n2) wherein n is 2 can be produced by reacting the present compound (1-nl) wherein n is 1 in the presence of an oxidant.
  • the reaction is generally conducted in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.
  • Examples of the oxidant to be used in the reaction include m-chloroperbenzoic acid and a hydrogen peroxide solution.
  • the amount of the oxidant to be used in the reaction is generally 1 to 4 moles, preferably 1 to 2 moles, relative to 1 mole of the present compound (1-nl).
  • the reaction temperature of the reaction is generally within a range of -20°C to 120°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 12 hours.
  • the present compound (l-n2) can be isolated by post-treatments, for example, extracting the reaction mixture, with an organic solvent, washing the organic layer with, optionally an aqueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer.
  • a reduction agent e.g., sodium sulfite and sodium thiosulfate
  • a base e.g., sodium hydrogen carbonate
  • the present compound represented by the formula (l-n2) wherein n is 2 can be also produced in one step (one pot) by reacting the present compound (1-nO) wherein n is 0 in the presence of an oxidant.
  • the reaction is generally conducted in the presence of a solvent.
  • Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.
  • Examples of the oxidant to be used in the reaction include m-chloroperbenzoic acid and a hydrogen peroxide solution.
  • the reaction may be conducted in the presence of a catalyst.
  • a catalyst examples include sodium tungstate.
  • the amount of the oxidant to be used in the reaction is generally 2 to 5 moles, preferably 2 to 3 moles, relative to 1 mole of the present compound (1-nO) .
  • the amount of the catalyst to be used. in the reaction is generally 0.01-0.5 moles relative to 1 mole of the present compound (1-nO) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 120°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 12 hours.
  • the present compound (l-n2) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, washing the organic layer with, optionally an aqueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer.
  • a reduction agent e.g., sodium sulfite and sodium thiosulfate
  • a base e.g., sodium hydrogen carbonate
  • the present compound (1) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M2) or the intermediate compound (M18) to give the intermediate compound (M3), and then condensing the resultin intermediate compound (M3) within the molecule.
  • the intermediate compound (M3) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M2) in the presence of a condensing agent .
  • the reaction is generally conducted . in the presence of a solvent.
  • ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as "THF"), and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate, and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as N, N-dimethylformamide (hereinafter referred to as "DMF”), N-methylpyrrolidone (hereinafter referred to as "NMP”), 1 , 3-dimethyl-2- imidazolidinone, and dimethyl
  • DMF N-di
  • Examples of the “condensing agent” to be used in the reaction include carbodiimides . such as l-ethyl-3- (3- dimethylaminopropyl ) carbodiimide hydrochloride (hereinafter referred to as "WSC”) and 1 , 3-dicyclohexyl carbodiimide.
  • carbodiimides such as l-ethyl-3- (3- dimethylaminopropyl ) carbodiimide hydrochloride (hereinafter referred to as "WSC”) and 1 , 3-dicyclohexyl carbodiimide.
  • the reaction may be conducted in the presence of a catalyst.
  • a catalyst examples include 1-hydroxybenzotriazol (hereinafter referred to as "HOBt " ) .
  • the amount of the intermediate compound (M2) to be used in the reaction is generally 0.5 to 2 moles relative to 1 mole of the intermediate compound (Ml) .
  • the amount of the condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml) .
  • the amount of the catalyst to be used in the reaction is generally 0.01 to 1 moles relative to 1 mole of the intermediate compound (Ml).
  • the reaction temperature of the reaction is generally within a range of 0°C to 120°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M3) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated intermediate compound (M3) can be further purified by recrystallization, chromatography, and the like.
  • the intermediate compound (M3) can be also produced by reacting the intermediate compound (Ml) with the intermediate compound (M18) .
  • the reaction is generally conducted in the presence of a solvent.
  • a solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as. acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • the reaction can be optionally conducted in the presence of a base.
  • a base examples include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the . amount of the intermediate compound (M18) to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (Ml) .
  • the reaction temperature of the reaction is generally within a range of -20°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M3) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M3) can be further purified by chromatography, recrystallization, and the like.
  • the present compound (1) can be produced by condensing the intermediate compound (M3) within the molecule.
  • the reaction is generally conducted in the presence of a solvent.
  • the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane , chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate, and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP., 1,3- dimethyl-2-imidazolidinone, and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
  • ethers such as 1,4-dioxane, diethyl ether, THF, and tert-but
  • the reaction may be conducted in the presence of a condensing agent, an acid, a base or a chlorinating agent.
  • Examples of the condensing agent to be used in the reaction include acetic acid anhydride, trifluoroacetic acid anhydride, WSC, a mixture of triphenyl phosphine, a base, and carbon tetrachloride or carbon tetrabromide, a mixture of triphenyl phosphine and azodiesters such as diethyl azodicarboxylate.
  • Examples of the acid to be used in the reaction include sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid; polyphosphoric acid; and the like.
  • Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2 , 6-lutidine, 1 , 8-diazabicyclo[ 5.4.0] - 7-undecene (hereinafter referred to as "DBU"), and 1,5- diazabicyclo[ 4.3.0] -5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as tripotassium phosphate, potassium carbonate, and sodium hydride.
  • nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2 , 6-lutidine, 1 , 8-diazabicyclo[ 5.4.0] - 7-undecene (hereinafter referred to as "DBU"), and 1,5- diazabicyclo[ 4.3.0] -5-nonene
  • tertiary amines such as triethy
  • chlorinating agent to be used in the reaction examples include phosphorous oxychloride; and the like.
  • the amount of the condensing agent is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3) .
  • the amount of the acid is generally 0.1 to 5 moles relative to 1 mole of the intermediate, compound (M3) .
  • the amount of the base is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3).
  • the amount of the chlorinating agent is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of .0.1 to 24 hours.
  • the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1) can be further purified by recrystallization, chromatography, and the like .
  • the present compound (1) can be also produced in one step (one pot) by reacting the intermediate compound (Ml) with the intermediate compound (M2) in the presence of a condensing agent.
  • the reaction is generally conducted in the presence of a solvent.
  • the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloro ethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, 1,3- dimethyl-2-imidazolidinone , and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
  • ethers such as 1,4-dioxane, diethyl ether, THF, and tert-buty
  • Examples of the condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3- dicyclohexyl carbodiimide .
  • the reaction may be conducted in the presence of a catalyst.
  • a catalyst examples include 1-hydroxybenzotriazol.
  • the amount of the intermediate compound (M2) to be used in the .reaction is generally 0.5 to . 2 moles relative to 1 mole of the intermediate compound (Ml) .
  • the amount of the condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml).
  • the amount of the catalyst to be used in the reaction is generally 0.01 to 1 moles relative to 1 mole of the intermediate compound (Ml).
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1) can be further purified by recrystallization, chromatography, and the like .
  • the present compound (1) can be also produced in one step (one pot) by reacting the intermediate compound (Ml) with the intermediate compound (M18) .
  • the reaction is generally conducted in the presence or absence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • aromatic hydrocarbons such as toluen
  • the reaction may be conducted in the presence of a base.
  • a base examples include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N, N-diisopropylethylamine; nitrogen- containing aromatic compounds such as pyridine and 4- dimethylaminopyridine; and the like.
  • the amount of the intermediate compound (M18) to be used; in the reaction is generally 1 to 3 moles relative to
  • the amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (Ml).
  • the reaction temperature of the reaction is generally within a range of 20°C to 200°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (1) can- be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated present compound (1) can be further purified by chromatography, recrystallization, and the like.
  • the present compound (P20) represented by the formula (1) wherein A 1 is a sulfur atom, and A 3 is a nitrogen atom can be produced by reacting the intermediate compound (M9) with the intermediate compound (M2) or the intermediate compound (M18) to give the intermediate compound (M14), and then reacting the resulting intermediate compound (M14) with a sulfating agent.
  • the intermediate compound (M14) can be produced by reacting. the intermediate compound (M9) with the intermediate compound (M2).
  • the reaction is generally conducted in the presence or absence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, N P, and DMSO; nitrogen-containing aromatic compounds such as pyridine. and quinoline; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and oct
  • Examples of the dehydrating condensing agent to be used in the reaction include carbodiimides such as WSC, 1 , 3-dicyclohexylcarbodiimide, and BOP agents.
  • the amount of the intermediate compound (M2) to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M9) .
  • the amount of the dehydrating condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M9) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M14) can be isolated by post-treatments, for ' example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M14) can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound (M14) can be also produced by reacting the intermediate compound (M9) with the intermediate compound (M18) .
  • the reaction is generally conducted in the presence or absence of a solvent, and may be conducted in the presence of a base .
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such . as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; nitrogen-containing aromatic compounds such as pyridine and guinoline; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aliphatic hydrocarbons such as hexane, heptane, and oc
  • Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N, -diisopropylethylamine; nitrogen- containing aromatic compounds such as pyridine and 4- dimethylaminopyridine; and the like.
  • the amount of the intermediate compound (M18) to be used in the reaction is generally 1 to 3 moles . relative to 1 mole of the intermediate compound (M9) .
  • the amount of the base to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M9).
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M14) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M14) can be further purified by chromatography, recrystallization, and the like.
  • the present compound (P20) can be produced by reacting the intermediate compound (M14) with a sulfating agent.
  • the reaction is generally conducted in the presence or absence of a solvent.
  • solvents such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butylmethyl ether, and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1 , 2-dichloroethane, and chlorobenzene ; aromatic hydrocarbons such as toluene, benzene, and xylene; nitriles such as acetonitrile; nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine, and quinoline;. and mixtures thereof.
  • sulfating agent examples include phosphorus pentasulfide, Lawesson's reagent ( 2 , 4-bis- ( 4-methoxyphenyl ) -1 , 3-dithia-2 , 4- diphosphetane-2, 4-disulfide) ; and the like.
  • the amount of the sulfating agent to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M14) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of 1 to 24 hours.
  • the present compound (P20) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (P20) can be further purified by recrystallization, chromatography, and the like.
  • the present compound (1) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M4) in the presence of an oxidant.
  • the reaction is generally conducted in the presence of a solvent.
  • the solvent to be used in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF, and tert- butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, 1 , 3-dimethyl-2- imidazolidinone, and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
  • alcohols such as methanol and ethanol
  • ethers such as 1,4-di
  • the reaction may be conducted in the presence of an acid.
  • the acid to be used in the reaction include sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid; polyphosphoric acid; and the like .
  • the reaction may be conducted in the presence of a sulfite.
  • a sulfite examples include sodium hydrogen sulfite, and disodium sulfite.
  • oxidant to be used in the reaction examples include oxygen, copper (II) chloride, DDQ; and the like.
  • the amount of the intermediate compound (M4) to be used in the reaction is generally 1 to 2 moles relative to 1 mole of the intermediate compound (Ml).
  • the amount of the acid to be used in the reaction is generally 0.1 to 2 moles relative to 1 mole of the intermediate compound (Ml) .
  • the amount of the sulfite to be used in the reaction is generally 1 to 5 moles relative to 1. mole of the intermediate compound (Ml) .
  • the amount of the oxidant to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 200°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1) can be further purified by recrystallization, chromatography, and the like.
  • the present compound represented by the formula (1) wherein n is 0 can be produced by reacting the intermediate compound (M6) with the intermediate compound (M7) in the presence of a base.
  • V 2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
  • the reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; water; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • aprotic polar solvents such as DMF, NMP, and DMSO
  • water and mixtures thereof.
  • Examples of the base to be used in the reaction include, alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metal hydrides such as sodium hydride.
  • the amount of the intermediate compound (M7) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M6) .
  • the amount of the base to be used in' the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M6) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 150°C.
  • the reaction time of the reaction is generally within a range of 0.5 to 24 hours.
  • the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
  • V 2 is preferably a fluorine atom or a chlorine atom.
  • the intermediate compound (M6) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M19) or the intermediate compound
  • V represents a halogen atom, and the other symbols are as defined in the formula (1) .
  • the intermediate compound (M20) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M19) instead of the intermediate compound (M2 ) .
  • the intermediate compound (M20) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M39) instead of the intermediate compound (Ml8 ) .
  • the intermediate compound (M6) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M20) instead of the intermediate compound (M3 ) .
  • the intermediate compound (M6) can be produced in one step (one pot) in the same manner as in Production process 2 except for using the intermediate compound (M19) instead of the intermediate compound (M6) .
  • the intermediate compound (M6) can. be produced in one step (one pot) in the same manner as in Production process 2 except for using the intermediate compound (M39) instead of the intermediate compound (M2).
  • V 2 is preferably a fluorine atom or a chlorine atom.
  • the present compound represented by the formula (1) wherein n is 0 can be produced by condensing the resulting intermediate compound (M3) within the molecule.
  • V 2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
  • the intermediate compound represented by the formula (M3) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M20) instead of the intermediate compound (M6) .
  • the present compound represented by the formula (1) wherein n is 0 can be produced in the same manner as in Production process 2 except for using the intermediate compound represented by the formula (M3) wherein n is 0 instead of the intermediate compound (M3) .
  • the present compound represented by the formula (1) wherein n is 0 can be produced in one step (one pot) in the same manner as in Production process 5 except for using the intermediate compound (M20) instead of the intermediate compound ( ⁇ ) .
  • n is 0
  • V 2 is preferably a fluorine atom or a chlorine atom.
  • the present compound represented by the formula (1) wherein n is 0 can be produced by reacting the intermediate compound (M8) or a disulfide thereof, the intermediate compound (M8 ' ) , with the intermediate compound (M17) in the presence of a base.
  • L is a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and the other symbols are as defined in the formula (1) .
  • the reaction is generally conducted in the presence of a solvent.
  • a solvent examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, N P, and DMSO; and mixtures thereof.
  • Examples of the base to be used in the reaction include inorganic bases such as alkali metal or alkaline earth metal hydrides, e.g., sodium hydride, potassium hydride, and calcium hydride; sodium carbonate; and potassium carbonate; and organic base such as triethylamine .
  • inorganic bases such as alkali metal or alkaline earth metal hydrides, e.g., sodium hydride, potassium hydride, and calcium hydride; sodium carbonate; and potassium carbonate
  • organic base such as triethylamine .
  • the reaction is generally conducted in the presence of a reductant.
  • Examples of the reductant to be used in the . reaction include sodium hydroxymethanesulfinate (trade name: Rongalite) .
  • the amount of the intermediate compound ( 17) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M8) .
  • the amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M8).
  • the amount of the intermediate compound (M17) to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the intermediate compound (M8 ' ) .
  • the amount of the base to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the intermediate compound (M8 ' ) .
  • the amount of the reductant to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M8 ' ) ⁇
  • the reaction temperature of the reaction is generally within a range of 0°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
  • the present compound represented by the formul'a (1) wherein n is 0 can be produced by reacting the intermediate compound (M8 ' ) with the intermediate compound (M17'-l) or the intermediate compound (M17'-2).
  • V 3 is a chlorine atom, a bromine atom, or an iodine atom, and the other symbols are as defined in the formula (1) .
  • the reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • aprotic polar solvents such as DMF, NMP, and DMSO
  • the amount of the intermediate compound (M17'-l) to be used in the reaction is generally 1 to 2 moles relative to 1 mole of the intermediate compound ( 8 ' ) .
  • the intermediate compound (M17'-2) is generally used in an amount of 1 to 2 moles relative to 1 mole of the intermediate compound (M8 ' ) .
  • the reaction temperature of the reaction is generally within a range of -80°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound (M8) can be produced by reacting the intermediate compound (M6) with a sulfating agent.
  • the intermediate compound (M8 ' ) which is a disulfide of the intermediate compound (M8), can be produced by oxidizing the intermediate compound (M8).
  • V 2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
  • the intermediate compound (M8) can be produced in the same manner as in Production process 5 except for using sodium sulfide, sodium hydrogen sulfide, hydrogen sulfide or the like instead of the intermediate compound (M7) .
  • V 2 is preferably a fluorine atom or a chlorine atom.
  • the intermediate compound (M8 ' ) can be produced by reacting the intermediate compound (M8) with an oxidant.
  • the reaction is generally conducted in the presence of a solvent.
  • Examples of the solvent to be used in the reaction include water; alcohols such as methanol and ethanol; ethers such as THF, ethylene glycol dimethyl ether, tert- butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; carboxylic acids such as acetic acid; and mixtures thereof.
  • alcohols such as methanol and ethanol
  • ethers such as THF, ethylene glycol dimethyl ether, tert- butylmethyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • aprotic polar solvents such as DMF, NMP, and DMSO
  • carboxylic acids such as acetic acid
  • oxidant to be used in the reaction examples include oxygen, iodine, . hydrogen peroxide solution, potassium ferricyanide; and the like.
  • the amount of the oxidant to be used in the reaction is generally 0.5 to 10 moles relative to 1 mole of the intermediate compound ( 8).
  • the reaction temperature of the reaction is generally within a range of 0°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M8 ' ) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound. (M8 ' ) can be further purified by chromatography, recrystallization, and the like [ 0133]
  • a 1 is —NR 71 — can be produced by reacting the present compound (P2) represented by the formula (1) wherein A 1 is —NH- with the intermediate compound (M10) in the presence of a base.
  • R 71 is any of the groups for R 7 other than a hydrogen atom in the formula (1)
  • L is an leaving group such as a chlorine atom, a bromine atom, an iodine atom, a -trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and the other symbols are as defined in the formula ( 1 ) .
  • the reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; . aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, N P, and DMSO; and mixtures thereof .
  • Examples of the base to be used in the reaction include alkali metal or alkaline earth metal hydride such as sodium hydride, potassium hydride, and calcium hydride; inorganic bases such as sodium carbonate, and potassium carbonate; organic bases such as triethylamine ; and the like .
  • the amount of the intermediate compound (M10) to be used in. the reaction is generally 1 to 5 moles relative to 1 mole of the present compound (P2) .
  • the amount of the base to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the present compound ( P2 ) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the present compound (P3) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated present compound (P3) can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound (M2) can be produced by hydrolyzing the intermediate compound ( 37).
  • an aqueous solution of the acid is generally used as a solvent in the reaction.
  • Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid.
  • the reaction temperature of the reaction is generally within a range of 0°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M2) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M2) can be further purified by chromatography, recrystallization, and the like [ 0135]
  • the hydrolysis is conducted by using a base
  • the reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, -dioxane; alcohols such as methanol and ethanol; water; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, -dioxane
  • alcohols such as methanol and ethanol
  • water and mixtures thereof.
  • Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the amount of the base to be used in the reaction is generally 1 to 10 moles, relative to 1 mole of the intermediate compound (M37) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 120°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M2) can be isolated by post-treatments, for example, acidifying the reaction solution, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M2) can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound ( 18) can be produced by reacting the intermediate compound (M2) with a chlorinating agent .
  • the reaction is generally conducted in the presence of a solvent .
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4 -dioxane; aromatic hydrocarbons such as toluene and xylene; aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4 -dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • aliphatic halogenated hydrocarbons such as dichloromethane and chloroform
  • chlorinating agent to be used in the reaction examples include thionyl chloride, oxalyl dichloride, phosphorous oxychloride; and the like.
  • the amount of the chlorinating agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M2) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound ( 18) can be isolated by removing the solvent from the reaction mixture.
  • the intermediate compound (M2) , the intermediate compound (M4) or the intermediate compound (M37) can be produced by reacting the intermediate compound (M7) with the intermediate compound (M19), the intermediate compound
  • the intermediate compound (M2) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M19) instead of the intermediate compound (M6) .
  • the intermediate compound (M4) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M22) instead of the intermediate compound (M6).
  • the intermediate compound (M37) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M36) instead of the intermediate compound (M6) .
  • the intermediate compound (M2) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M2) wherein n is 0 instead of the present compound (1) wherein n is 0.
  • the intermediate compound (M4) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M4) wherein n is 0 instead of the present compound (1) wherein n is 0.
  • the intermediate compound (M37) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M37) wherein n is 0 instead of the present compound (1) wherein n is 0.
  • V 2 is preferably a fluorine atom or a chlorine atom.
  • the intermediate compound (M30) can be produced by nitrating the intermediate compound (M29) , or reacting the intermediate compound (M33) with the intermediate compound (M28). By reducing the resulting intermediate compound (M30), the intermediate compound (Ml) represented by the formula (Ml) wherein A 1 is -NR 7 - can be produced.
  • the intermediate compound (M30) can be produced by reacting the intermediate compound (M33) with the intermediate compound (M28) in the presence of a base.
  • the reaction is generally conducted in the presence of a solvent.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • aprotic polar solvents such as DMF, NMP, and DMSO
  • the reaction may be conducted in the presence of a base .
  • Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, and potassium carbonate; tertiary amines such as triethylamine and N, -diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4- dimethylaminopyridine .
  • alkali metal hydrides such as sodium hydride
  • alkali metal carbonates such as sodium carbonate, and potassium carbonate
  • tertiary amines such as triethylamine and N, -diisopropylethylamine
  • nitrogen-containing aromatic compounds such as pyridine and 4- dimethylaminopyridine .
  • the amount of the intermediate compound (M28) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M33) .
  • the amount of the base to be used in the reaction is generally 0 to 10 moles relative to 1 mole of the intermediate compound (M6) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 150°C.
  • the reaction time of the reaction is generally within a range of 0.5 to 24 hours.
  • the intermediate compound (M30) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization, and the like [ 0142]
  • the intermediate compound (M30) can be produced by reacting the intermediate compound (M29) with a nitrating agent .
  • the reaction is generally conducted in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons such . as dichloromethane, and chloroform; acetic acid, concentrated sulfuric acid, concentrated nitric acid, water; and mixtures thereof.
  • nitrating agent to be used in the reaction examples include concentrated nitric acid; and the like.
  • the amount of the nitrating agent to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M29) .
  • the reaction temperature of the reaction is generally within a range of -10°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (M30) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M30) can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound (M30) wherein R 7 is a group other than a hydrogen atom can be produced in the same manner as in Production process 11 except for using the intermediate compound (M30) wherein R 7 is a hydrogen atom instead of the present compound (P2) .
  • the intermediate compound (Ml) wherein A 1 is -NR 7 - can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenating catalyst.
  • the reaction is generally conducted in the presence of a solvent, under hydrogen atmosphere at 1 to 100 atm.
  • solvent to be used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; water ; and mixtures thereof.
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane
  • esters such as ethyl acetate and butyl acetate
  • alcohols such as methanol and ethanol
  • water and mixtures thereof.
  • Examples of the hydrogenating catalyst to be used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
  • the amount of the hydrogen to be used in the reaction is generally 3 moles relative to 1 mole of the intermediate compound (M30 ) .
  • the amount of the hydrogenating catalyst to be used in the reaction is generally 0.001 to 0.5 moles relative to 1 mole of the intermediate compound (M30).
  • the reaction may be conducted in the presence of an acid or a base, if necessary.
  • Examples of the acid to be used in the reaction include acetic acid, hydrochloric acid, and the like.
  • Examples of the base to be used in the reaction include tertiary amines such as triethylamine; magnesium oxide; and the like.
  • the reaction temperature of the reaction is generally within a range of -20°C to 100°C.
  • the reaction time of the reaction is generally within a range of 0.1 to 24 hours.
  • the intermediate compound (Ml) wherein A 1 is -NR 7 - can be isolated by post- treatments, for example, filtrating the reaction mixture, optionally extracting the reaction mixture with an organic solvent., and drying and concentrating the organic layer.
  • the isolated intermediate compound (Ml) wherein A 1 is -NR 7 - can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound (M30) can be produced by acetylating the intermediate compound (M29) to give the intermediate compound (M29 1 ), nitrating the resulting intermediate compound ( ⁇ 29') to give the intermediate compound ( ⁇ 30'), and hydrolyzing the resulting intermediate compound (M30 ' ) .
  • the intermediate compound ( ⁇ 29') can be produced by reacting the intermediate compound (M29) with an acylating agent .
  • the reaction is generally conducted in the presence of a solvent or using the acylating agent as a solvent.
  • solvent to be used in the reaction examples include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, 4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
  • aliphatic halogenated hydrocarbons such as dichloromethane and chloroform
  • ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, 4-dioxane
  • aromatic hydrocarbons such as toluene and xylene
  • nitriles such as acetonitrile
  • aprotic polar solvents such as DMF, NMP, and DMSO
  • acylating agent examples include acetic acid anhydride, para- acetoxynitrobenzene; and the like.
  • the reaction may be conducted in the presence of a base.
  • Examples of the base to be used in the reaction include tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4 -dimethylaminopyridine .
  • the amount of the acylating agent to be used in the reaction is generally not less than 1 mole relative to 1 mole of the intermediate compound (M29) .
  • the amount of the base to be used in the reaction is generally 0.1 to 10 moles relative to 1 mole of the intermediate compound (M29) .
  • the reaction temperature of the reaction is generally within a range of 0°C to 150°C.
  • the reaction time of the reaction is generally within a range of 0.5 to 24 hours.
  • the intermediate compound ( ⁇ 29') can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
  • the isolated intermediate compound (M29 1 ) can be further purified by chromatography, recrystallization, and the like.
  • the intermediate compound ( ⁇ 30') can be produced in the same manner as in Production process 15 except for using the ⁇ intermediate compound (M29 1 ) instead of the intermediate compound (M29) .
  • the intermediate compound (M30) can be produced by hydrolyzing the intermediate compound (M30 ' ) in the presence of an acid or a base.
  • an aqueous solution of the acid is generally used as a solvent in the reaction.
  • Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid and sulfuric acid; and carboxyli.c acids such as acetic acid and trifluoroacetic acid.

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Abstract

There is provided a compound having an excellent controlling effect on pests represented by the formula (1):

Description

DESCRIPTION
FUSED HETEROCYCLIC COMPOUND AND USE THEREOF FOR PEST
CONTROL
Technical Field
[ 0001]
The present application is filed claiming the priority of the Japanese Patent Application Nos. 2011-170833, 2012- 079323 and 2012-122837, the entire contents of which are herein incorporated by reference.
The present invention relates to a fused heterocyclic compound and the use thereof for pest control.
Background Art.
[ 0002]
For controlling pests, various compounds have been developed and used practically.
Further, some fused heterocyclic compounds are known (see, Patent Literature 1).
Citation List
[ 0003]
Patent Literature
Patent Literature 1: JP-A-2004-3 438
Summary of Invention Technical Problem
[ 0004]
An object of the present invention is to provide a novel compound having an excellent controlling effect on pests and a method for controlling pests with said compound
Solution to Problem
[ 0005]
The inventors of the present invention have intensively studied, and as a result, they have found that a fused heterocyclic compound represented by the following formula (1) has an excellent controlling effect on pests. Thus, the present invention has been completed.
[ 0006]
The present invention includes the followings:
[ 1] A fused heterocyclic compound represented by the formula ( 1 ) :
Figure imgf000003_0001
wherein
A represents -NR -, an oxygen atom or a sulfur atom,
A2 represents a nitrogen atom or =CR8-,
A3 represents a nitrogen atom or =CR9-,
R1 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y,
R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -S (0 ) 2NR10R1:L, - NR10R , -NR10CO2R11, -NR10C (0 ) R11, -C02R10, -C(0)R10, C(O)NR10R1:i", -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -S (0 ) 2NR10RU, - NR10R , -NR10C02RU, -NR10C (0 ) R11, -C02R10, -C(0)R10, C(O)NR10R1:L, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom (wherein R5 and R6 do not represents a hydrogen atom at the same time), R7 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl, group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), -CO2R10, -C(0)R10, a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y or a hydrogen atom,
R8 and R9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen, atoms, -OR10, -S(0)mR10, -NR10Rn, -C02R10, - C(0)R10, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R10 and R11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom,
each m independently represents 0, 1 or 2, and
n represents 0, 1 or 2,
wherein the -S (0 ) mR10, R10 does not a hydrogen atom when m is 1 or 2,
Group X: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one. or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more . halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups, a cyano group, a hydroxy group and a halogen atom,
Group Y: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms and a halogen atom,
Group Z: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group optionally substituted by one or more halogen atoms, a halogen atom, a cyano group and a nitro group,
Group W: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfInyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, hydroxy group, a halogen atom and a cyano group,
or an N-oxide thereof (hereinafter referred to as "the present compound") .
[ 2] The compound according to the above [ 1] , wherein
A1 is -NR7-, an oxygen atom or a sulfur atom,
A2 is a nitrogen atom or =CR8-,
A3 is a nitrogen atom or =CR9-,
R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X,
R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, S(0)mR10, -SF5, a halogen atom or a hydrogen atom, R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is- optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), or a hydrogen atom,
R is a C1-C6 chain hydrocarbon group ' optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom, and
R9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
[ 3] The compound according to the above. [ 1] , wherein
A1 is -NR7-, an oxygen atom or a sulfur atom,
A2 is a nitrogen atom or =CR8-,
A3 is a nitrogen atom or =CR9-,
R1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl group) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2 and. R4 are the same or different each other and each represents a halogen atom or a hydrogen atom,
R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen, atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR10, -S(0)mR10, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, -SF5 or a halogen atom, R6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom,
R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms,
R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a. C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or' groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms, R is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom,, and
R9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
[ 4] The compound according to any one of the above [ 1] to [ 3] , wherein A1 is -NR7- .
[ 5] The compound according to any one of the above [ 1] to [ 3] , wherein A1 is an oxygen atom.
[ 6] The compound according to any one of the above [ 1] to [ 3] , wherein A1 is a sulfur atom.
[ 7] The compound according to any one of the above [ 1] to [ 6] , wherein A2 is =CR8- .
[ 8] The compound according to any one of the above [ 1] to
[ 6] , wherein A2 is =CR8-, and A3 is a nitrogen atom.
[ 9] The compound according to any one of the above [ 1] to
[ 6] , wherein A2 is =CR8-, and A3 is =CR9- .
[ 10] A compound represented by the formula (1-1) :
Figure imgf000012_0001
wherein
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9 -,
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
Ra and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) , -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms),
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R2 a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 11] The compound according to the above [ 10] , wherein Ala is -NR7a-, an oxygen atom or a sulfur atom,
A3a is a nitrogen atom or =CR9a-,
Rla is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups),
R2 and R4a both are a. hydrogen atom,
R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2 ) , a halogen atom or a hydrogen atom,
R5a is a C1-C6 haloalkyl group, -OR2a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom, and
R7a is a" C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one . or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) .
[ 12] The compound according to the above [ 10] or [ 11] , wherein Ala is -NR7a- .
[ 13] The compound according to the above [ 10] or [ 11] , wherein Ala is an oxygen atom.
[ 14] The compound according to the above [ 10] or [ 11] , wherein Ala is a sulfur atom.
[ 15] A compound represented by the formula (1-2) :
Figure imgf000016_0001
wherein
A 3b represents a nitrogen atom or =CR - (wherein R 9b represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group,
R7. represents methyl group or a propargyl group,
R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, . m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 16] A compound represented by the formula (1-3) :
Figure imgf000017_0001
wherein
A 3b represents a nitrogen atom or =CR - (wherein R 9b represents a hydrogen atom or a halogen atom) , R represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R2 represents a C1-C6 haloalkyl group), -S(0)mR23 (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 17] A compound represented by the formula (1-4) :
Figure imgf000018_0001
wherein
A represents a nitrogen atom or =CR - (wherein R represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mFriD (wherein R1b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group,. -OR22b (wherein R22 represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2 ) , -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[18] A. compound represented by the formula (1-5):
Figure imgf000019_0001
wherein
R represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms,
A3a represents a nitrogen atom or =CR9a-,
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and . a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR2a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents .0, ,1 or 2,
or an N-oxide thereof.
[ 19] A pest control composition comprising a compound according to any one of the above [1] to [ 18] and an inert carrier .
[20] A method for controlling a pest, which comprises applying an effective amount of the compound according to any one of the above [1] to [ 18] to the pest or a habitat of the pest.
[21] A compound represented by the formula (M3-1):
Figure imgf000021_0001
wherein
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9a-, R a represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is . optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,. - R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group Optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 . alkoxy group optionally substituted by one or more halogen atoms ) , -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group, optionally substituted by one or more halogen atoms, -OR22a (wherein R2a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR3a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one- or more atoms or groups selected from the group consisting of a halogen atom, a C1-G3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms),
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , a halogen atom or a hydrogen atom,
n represents 0, 1 or 2, and
or an N-oxide thereof.
[ 22] A compound represented by the formula (M6-1) :
Figure imgf000024_0001
wherein
V2 represents a halogen atom,
A represents -NR -, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9a-,
R2a and Ra are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted, by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered. aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is. optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and -
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms ) , -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
or an N-oxide thereof.
[ 23] A compound represented by the formula (M20-1) :
Figure imgf000026_0001
wherein
V2 represents a halogen atom,
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9a-,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or β-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) , -OR20a (wherein n
R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl . group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6. alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the .5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and R a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25 represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
or an N-oxide thereof. Effect of Invention
[ 0007]
The present compound has an excellent controlling effect on pests and is useful as1 an active ingredient of a pest control agent.
Description of Embodiments
[ 0008] -
The "N-oxide" in the present . compound means a compound wherein a nitrogen atom constituting a ring in a heterocyclic group is oxidized. Examples of the
"heterocyclic group" which can form the N-oxide in the present compound include a pyridine ring.
[ 0009] .
The groups used herein will be illustrated in detail by way of examples. [ 0010]
In the present application, the "Ca-Cb chain hydrocarbon group" means a linear or branched, saturated or unsaturated hydrocarbon group having a to b carbon atoms; the "Ca-Cb alkyl group" means a linear or branched hydrocarbon group having a to b carbon atoms;
the "Ca-Cb alkenyl group" means a linear or branched, unsaturated hydrocarbon group having a to b carbon atoms and one or more double bonds within the molecule;
the "Ca-Cb alkynyl group" means a linear or branched, unsaturated hydrocarbon group having a to b carbon atoms and one or more triple bonds within the molecule;
the "Ca-Cb haloalkyl group" means a linear or branched alkyl group having a to b carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are substituted by one or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other; the Ca-Cb alkoxy group" means a linear or branched alkyl-O-group having a to b carbon atoms;
the "Ca-Cb alkenyloxy group" means a linear or branched alkenyl-O-group having a to b carbon atoms and one or more double bonds within the molecule;
the "Ca-Cb" alkynyloxy group" means, a linear or branched alkynyl-O-group having a to b carbon atoms and one or more triple bonds within the molecule;
the "Ca-Cb alkylsulfanyl group" means a linear or branched alkyl-S-group having a to b carbon atoms;
the "Ca-Cb alkylsulfinyl group" means a linear or branched alkyl-S (0 ) -group having a to b carbon atoms;
the "Ca-Cb alkylsulfonyl group" means a linear or branched alkyl-S (0 ) 2-group having a to b carbon atoms;
the "Ca-Cb alkyl carbonyl group" means a linear or branched alkyl-C (0 ) -group having a to b carbon atoms;
the "Ca-Cb alkoxycarbonyl group" means a linear or branched alkyl-O-C (0 ) -group having a to b carbon atoms;
the "Ca-Cb alicyclic hydrocarbon group" means a cyclic nonaromatic hydrocarbon group having a to b carbon atoms; the "Ca-Cb cycloalkyl group" means a cyclic alkyl group having a to b carbon atoms;
the "Ca-Cb alkylamino group" means a linear or branched alkyl-NH-group having a to b carbon atoms;
the. "Ca-Cb dialkylamino group" means a linear or branched dialkylamino group, wherein the alkyl groups have the same or different carbon atoms and the total number of carbon atoms is a to b;
the "Ca-Cb alkoxyalkyl group" means a linear or branched alkyl-0-alkyl group, wherein the alkyl groups have the same or different carbon atoms and the total number of carbon atoms is a to b. [ 0011]
In the "optionally substituted by one or more atoms or groups selected from Group X" used herein, when two or more atoms or groups selected from Group X are present, these atoms or groups selected from Group X are the same or different from each other.
In the "optionally substituted by one or more atoms or groups selected from Group Y" used herein, when two or more atoms or groups selected from Group Y are present, these atoms or groups selected from Group Y are the same or different from each other.
In the "optionally substituted by one or more atoms or groups selected from Group Z" used herein, when two or more atoms or groups selected from Group Z are present, these atoms or groups selected from Group Z are the same or different from each other.
In the "optionally substituted by one or more atoms or groups selected from Group W" used herein, when two or more atoms or groups selected from Group are present, these atoms or groups selected from Group W are the same or different from each other.
In the "optionally substituted by one or more halogen atoms" used herein, when two or more halogen atoms are present, these halogen atoms are the same or different from each other. [ 0012]
The "halogen atom" in the present compound includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
[ 0013]
The "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X" in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one or more atoms or groups selected from Group X, and when the group is substituted by two or more atoms or groups selected from Group X, these atoms or groups are the same or different from each other.
Examples of the "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X" in the present compound include Cl- C6 alkyl groups optionally substituted by one or more atoms or groups selected from Group X, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl ■group, a pentyl group, a neopentyl group, a hexyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert- butyloxymethyl group, a 2-methoxyethyl group, a 2- ethoxyethyl group, a 2-propyloxyethyl group, a 2- isopropyloxyethyl group, a 2-butyloxyethyl group, a 2-sec- butyloxyethyl group, a 2-tert-butyloxyethyl group, a trifluoromethyl group, a trichloromethy'l group, a 2- fluoroethyl group, a 2 , 2-difluoroethyl group, a 2,2,2- trifluoroethyl group and a pentafluoroethyl group, a methylsulfanylethyl group, a ethylsulfanylethyl group, a methylsulfinylethyl group, a methylsulfonylethyl group, a 2-hydroxy ethyl group, a cyclopropylmethyl group, a 1- methylcyclopropylmethyl group, a 2,2- difluorocyclopropylmethyl group, and the like;
C2-C6 alkenyl groups optionally substituted by one or more atoms or groups selected from Group X, such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-l-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like; and
C2-C6 alkynyl groups optionally substituted by one or more atoms or groups selected from Group X, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group and a 4,4,4- trifluoro-2-butynyl group, and the like; which is selected depending on a given range of carbon atoms. [ 0014]
The "C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y" in the present compound means a cyclic non- aromatic hydrocarbon group having 3 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom ( s ) is/are optionally substituted by one or more atoms or groups selected from Group Y, and when the group is substituted by two or more atoms or groups selected from Group Y, these atoms or groups are the same or different from each other.
Examples of the "C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y" in the present compound include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2- cyclohexenyl group, a 3-cyclohexenyl group, a 1- methylcyclohexyl group, a 2-methylcyclohexyl group, a 3- methylcyclohexyl group, a -methylcyclohexyl group, a 2- methoxycyclohexyl group, a 3-methoxycyclohexyl group, a 4- methoxycyclohexyl group, a 1-fluorocyclohexyl group, a 2- fluorocyclohexyl group, a 3-fluorocyclohexyl group, and a 4-fluorocyclohexyl group.
[ 0015]
The "C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms" in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one . or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other.
Examples of the "C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms" in the present compound include C1-C6 alkyl groups optionally substituted by^ one or more halogen atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2 , 2-difluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, and the like;
C2-C6 alkenyl groups optionally substituted by one or more halogen, atoms such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-l- propenyl group, a 1-butenyl group, a 2-butenyl group, a 3- butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like; C2-C6 alkynyl groups optionally substituted by one or more halogen atoms such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a l-pentynyl group, a 1-hexynyl group, a 4 , 4 , 4-trifluoro-2-butynyl group, and the like; which is selected depending on a given range of carbon atoms .
[ 0016]
The "phenyl group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound means a phenyl group, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are optionally substituted by one or more atoms or groups selected from Group Z, and when the group is substituted by two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
Examples of the "phenyl group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound . include a phenyl group, a 2- fluorophenyl group, a 3-fluorophenyl group, a 4- fluorophenyl group, a 2 , 3-difluorophenyl group, a 2,4- difluorophenyl group, a 2 , 5-difluorophenyl group, a 2,6- difluorophenyl group, a 3 , -difluorophenyl group, a 3,5- difluorophenyl group, a 2 , 3 , 4 , 5 , 6-pentafluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4- chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4 -bromophenyl group, a 2-iodophenyl group, a 3- iodophenyl group, a 4 -iodophenyl group, a 2-trifluoromethyl phenyl group, a 3-trifluoromethylphenyl group, a 4- trifluoromethylphenyl group, a 2-trifluoromethoxyphenyl group, a 3-trifluoromethoxyphenyl group, a 4- trifluoromethoxyphenyl group, a 2- trifluoromethylsulfanylphenyl group, a 3- trifluoromethylsulfanylphenyl group, a 4- trifluoromethylsulfanylphenyl group, a 4- methoxycarbonylphenyl group, a 4-nitrophenyl group, a 4- cyanophenyl group, a 4-methylaminophenyl group, a 4- dimethylaminophenyl group, a 4-methylsulfinylphenyl group, a 4-methylsulfonylphenyl group, a 4-acetylphenyl group and a 4-methoxycarbonylphenyl group.
[ 0017]
The "heterocyclic group" in the present compound means a residue of a heterocyclic compound having one or more nitrogen atoms, oxygen atoms or sulfur atoms in addition to carbon atoms in the ring structure.
The "5-membered heterocyclic group" in the present compound means a 5-membered aromatic heterocyclic group or 5-membered non-aromatic heterocyclic group, and the "6- membered heterocyclic group" means a 6-membered aromatic heterocyclic group or a. 6-membered non-aromatic heterocyclic group. [ 0018]
The "heterocyclic group" in the "5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound means a residue of a heterocyclic compound having one or more nitrogen atoms, oxygen atoms or sulfur atoms in addition to carbon atoms in the ring structure, wherein the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
The "5- or 6-membered heterocyclic group" in the present compound means a 5- or β-membered aromatic heterocyclic group, or a 5- or 6-membered non-aromatic heterocyclic group.
Examples of the "5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z" in the present compound include 5 or 6-membered non-aromatic heterocyclic groups optionally substituted by one or more atoms or groups selected from Group Z, such as a pyrrolidin-l-yl group, a 3,3,4,4- tetrafluoropyrrolidin-l-yl group, a tetrahydrofuran-2-yl group, a piperidyl group, a morpholyl group, a thiomorpholyl group, and the like;
5- or 6-membered aromatic heterocyclic groups optionally substituted by one or more atoms or groups selected from Group Z, such as a 2-pyrroly group, a 2-furyl group, a 3- furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1- pyrroly group, a l-methyl-2-pyrroly ' group, a 2- methylsulfanyl-l-pyrroly group, a 2-methylsulfinyl-1- pyrroly. group, a 2-methylsulfonyl-l-pyrroly group, a 2- methylamino-l-pyrroly group, a 2-dimethylamino-l-pyrroly group, a 5-bromo-2-furyl group, a 5-nitro-2-furyl group, a 5-cyano-2-furyl group, a 5-methoxy-2-furyl group, a 5- acetyl-2-furyl group, a 5-methoxycarbonyl-2-furyl group, a 2-methyl-3-furyl group, a 2 , 5-dimethyl-3-furyl group, a 2 , 4 -dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a
3-methyl-2-thienyl group, a l-methyl-3-trifluoromethyl-5- pyrazolyl group, a 5-chloro-l , 3-dimethyl-4 -pyrazolyl group, pyrazol-l-yl group, a 3-chloro-pyrazol-l-yl group, a 3- bromopyrazol-l-yl group, a 4-chloropyrazol-l-yl group, a.4- bromopyrazol-l-yl group, an imidazole-l-yl group, a 1,2,4- triazol-l-yl group, a 3-chloro-l , 2 , 4 -triazol-l-yl group, a 1 , 2 , 3 , 4-tetrazol-l-yl group, a 1 , 2 , 3 , 5-tetrazol-l-yl group, a 2-thienyl group, a 3-thienyl group, a 3-trifluoromethyl- 1, 2, 4-triazol-l-yl group, a 4 -trifluoromethyl pyrazol-l-yl group, pyrazinyl group, a 4-pyrimidinyl group, a 5- pyrimidinyl group, a 2-pyridyl group, a 3-pyridyl group, a
4-pyridyl group, a 3-fluoro-2-pyridyl group, a 4-fluoro-2- pyridyl group, a 5-fluoro-2-pyridyl group, a 6-fluoro-2- pyridyl group, a 2-pyrimidinyl group, a 3-chloro-5- trifluoromethylpyridin-2-yl group, a 5- trifluoromethylpyridin-2-yl group, and the like.
[ 0019]
Examples of the "C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z) " in the present compound include a phenylmethyl group, a 4 -chlorophenylmethyl group and a 4- trifluoromethyl phenylmethyl group, and the like. When the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
[ 0020]
Examples of the "C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z ) " in the present compound include 5 or 6-membered non-aromatic heterocyclic groups such as a tetrahydrofuran-2-ylmethyl group, a tetrahydropyran-2- ylmethyl group, a tetrahydropyran-3-ylmethyl group, and the like;
5- or 6-membered aromatic heterocyclic groups such as a thiazol-5-ylmethyl group, a 2-chlorothiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3- ylmethyl group, a 6-trifluoromethylpyridin-3-ylmethyl group, and the like. When the group has two or more atoms or groups selected from Group Z, these atoms or groups are the same or different from each other.
[ 0021]
Examples of the "C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a thiazol- 5-ylmethyl group, a 2-chlorothiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group, a 6-trifluoromethylpyridin-3-ylmethyl group, and the like.
[ 0022]
Examples of the "5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyrroly group, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrroly group, a l-methyl-2-pyrroly group, a 5- bromo-2-furyl group, a 5-methoxy-2-furyl group, a 2-methyl- 3-furyl group, a 2 , 5-dimethyl-3-furyl group, a 2,4- dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a 3- methyl-2-thienyl group, a l-methyl-3-trifluoromethyl-5- pyrazolyl group, a 5-chloro-l, 3-dimethyl-4-pyrazolyl group, a pyrazol-l-yl group, a 3-chloro-pyrazol-l-yl group, a 3- bromopyrazol-l-yl group, a 4 -chloropyrazol-l-yl group, a 4- bromopyrazol-l-yl group, an imidazole-l-yl group, a' 1,2,4- triazol-l-yl group, a 3-chloro-l, 2, 4-triazol-l-yl group, a 1, 2, 3, 4-tetrazol-l-yl group, a 1 , 2 , 3 , 5-tetrazol-l-yl group, a 2-thienyl group, a 3-thienyl group, a 3-trifluoromethyl- 1, 2, 4-triazol-l-yl group, a 4-trifluoromethyl pyrazol-l-yl group, a pyrazinyl group, a 4 -pyrimidinyl group, a 5- pyrimidinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-fluoro-2-pyridyl group, a 4-fluoro-2- pyridyl group, a 5-fluoro-2-pyridyl group, a 6-fluoro-2- pyridyl group, a 2-pyrimidinyl group, a 3-chloro-5- trifluoromethylpyridin-2-yl group, a 5- trifluoromethylpyridin-2-yl group, and the like.
[ 0023]
Examples of the "C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups)" in the present compound include a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, an isobutyl group, a sec-butyl group, a tert- butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2 , 2-difluoroethyl group, a 2,2,2- trifluoroethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a cyclopropylmethyl group, a 2- cyclopropylethyl group, a 1-cyclopropylethyl group, a 1- methylcyclopropylmethyl group, and the like.
[ 0024]
Examples o" the "C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W" in the present compound include Cl- C6 alkyl groups optionally substituted by one or more atoms or groups selected from Group W, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2 , 2-difluoroethyl group, a 2,2,2- trifluoroethyl group, a pentafluoroethyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, an isobutyloxymethyl group, a tert-butyloxymethyl group, a methoxyethyl group, an ethoxyethyl group, a propyloxyethyl group, an isopropyloxyethyl group, a butyloxyethyl group, a sec-butyloxyethyl group, an isobutyloxyethyl group, a tert- butyloxyethyl group, a methylsulfanylethyl group, an ethylsulfanylethyl group, a methylsulfinylethyl group, methylsulfonylethyl group, a methoxycarbonylmethyl group, a methoxycarbonylethyl group, a 2-cyanoethyl group, a 2- oxopropyl, a cyclopropylmethyl group, a cyclohexylmethyl group, and the like;
C2-C6 alkenyl groups optionally substituted by one or more atoms or groups selected from Group W, such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1- methylvinyl group, a 2-methyl-l-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, pentafluoroallyl group, and the like;
C2-C6 alkynyl groups optionally substituted by one or more atoms or groups selected from Group W, such as an ethynyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4,4,4- trifluoro-2-butynyl group, and the like. When the group has two or more atoms or groups selected from Group W, these atoms or groups are the same or different from each other .
[ 0025]
Examples of the "C1-C6 alkoxy group optionally substituted by one or more halogen atoms" in the present compound include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2 , 2 , 2-trifluoroethoxy group, .a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, and the like.
[ 0026]
Examples of the "C2-C6 alkenyloxy group substituted by one or more halogen atoms" in the present compound include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2- butenyloxy group, a 3-butenyloxy group, a 2-pentenyloxy group, a 2-hexenyloxy group, a 3, 3-difluoroallyloxy group, a 3,3-dichloro allyloxy group, and the like.
[ 0027]
Examples of the "C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms" in the present compound include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 2-hexynyloxy group, a 4 , 4 , -trifluoro-2-butynyl oxy group, and the like.
[ 0028] Examples of the "C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms" in the present compound include . a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl . group, , a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2 , 2 , 2-trifluoroethylsulfanyl group, a pentafluoroethylsulfanyl group, and the like.
[ 0029]
Examples of the "C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms" in the present compound include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2 , 2 , 2-trifluoroethylsulfinyl group, a pentafluoroethylsulfinyl group, and the like..
[ 0030]
Examples of the "C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms" in the present compound include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a 2 , 2 , 2-trifluoroethylsulfonyl group, a pentafluoroethylsulfonyl group, and the like.
[ 0031]
Examples of the "C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms" in the present compound include an acetyl group, a propionyl group, a butyryl group, a pentanoyl group, a hexanoyl group, a trifluoroacetyl group, and the like.
[ 0032]
Examples of the "C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms" in the present compound include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a pentyloxycarbonyl group, a tert-butyloxycarbonyl group, a 2 , 2 , 2-trifluoroethyloxycarbonyl group, and the like.
[ 0033]
Examples of the "C1-C6 alkylamino group optionally substituted by one or more halogen atoms" in the present compound include a methylamino group, an ethylamino group, a 2 , 2 , 2-trifluoroethylamino group, a propylamino group, an isopropylamino group, a butylamino group, and the like.
[ 0034]
Examples of the "C2-C8 dialkylamino group optionally substituted by one or more halogen atoms" in the present compound include a dimethylamino group, a diethylamino group, a bis ( 2 , 2 , 2-trifluoroethyl ) amino group, a dipropylamino group, and the like.
[ 0035]
Examples of the "C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms" in the present compound include a cyclopropyl group, a 2,2- difluorocyclopropyl group, a 2 , 2-dichlorocyclopropyl group, a 2 , 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
[ 0036]
Examples of the "C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more Cl- C3 . alkyl groups" in the present compound include a cyclopropyl group, a 1-methylcyclopropyl group, a 2- methylcyclopropyl group, a 1-fluorocyclopropyl group, a 2 , 2-difluorocyclopropyl group, a 2 , 2-dichlorocyclopropyl group, a 2 , 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
[ 0037]
Examples of the "C2-C6 alkyl group" in the present compound include an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec- butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, and the like.
[ 0038]
The "C1-C6 haloalkyl group" in the present compound means a linear or branched hydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/are substituted by one or more halogen atoms, and when the group is substituted by two or more halogen atoms, these halogen atoms are the same or different from each other.
Examples of the "C1-C6 haloalkyl group" in the present compound include a fluoro methyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group-, a bromodifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2 , 2-difluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, and the like.
[ 0039]
Examples of the "C4-C9 cyclopropylalkyl group (wherein the cyclopropyl■ group is optionally substituted by one or more halogen atoms or one or more Cl-C.3 alkyl groups)" in the present compound include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a 1-cyclopropylethyl group, a 1- methylcyclopropyl group, and the like.
[ 0040]
Examples of the "C1-C6 perfluoroalkyl group" in the present compound include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, and the like.
[ 0041]
Examples of the "C1-C6 alkyl group optionally substituted by one or more halogen atoms" in the present compound include a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a trichloromethyl group, a 2- fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a 2 , 2-difluoroethyl group, a 2 , 2 , 2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, and the like.
[ 0042]
Examples of the "C2-C6 alkenyl group optionally substituted by one or more halogen atoms" in the present compound include a vinyl group, a 1-propenyl group, a 2- propenyl group, a 1-methyl vinyl group, a 2-methyl-l- propenyl group, a 1-butenyl group., a 2-butenyl group, a 3- butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1, 1-difluoroallyl group, a pentafluoroallyl group, and the like .
' [ 0043]
Examples of the "C2-C6 alkynyl group optionally substituted by one or more halogen atoms" in the present compound include an ethynyl group, a propargyl group, a 2- butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1- hexynyl group, a 4 , , 4-trifluoro-2-butynyl group, and the like.
[ 0044]
Examples of the "C3-C6 alkenyl group optionally substituted by one or more halogen atoms" in the present compound include a 1-propenyl group, a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-l-propenyl group, a 1- butenyl group, a 2-butenyl group, a 3-butenyl group, a 1- pentenyl group, a 1-hexenyl group, a 1 , 1-difluoroallyl group, a pentafluoroallyl group, and the like.
[ 0045]
Examples of the "C3-C6 alkynyl . group optionally substituted by one or more halogen atoms" in the present compound include a propargyl group, a 2-butynyl group, a 3- butynyl group, a 1-pentynyl group, a 1-hexynyl group, a 4 , 4 , 4-trifluoro-2-butynyl group, and the like.
[ 0046]
Examples of the "C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms" in the present compound include a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group, a 2- (methoxy) ethyl group, a 1- (ethoxy) ethyl group, a 2- (ethoxy) ethyl group, a 2,2,2- trifluoroethoxymethyl group, and the like.
[ 0047]
Examples of the "pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 5-trifluoromethyl-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, and the like.
[ 0048]
Examples of the "pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a 2-pyrimidinyl group, a 4- pyrimidinyl group, a 5-pyrimidinyl group, a 2-chloro-4- pyrimidinyl group, and the like.
[ 0049]
Examples of the "C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one. or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a ( thiazol-5-yl ) methyl group, a ( 2-chlorothiazol-5-yl ) methyl group, a 1- ( 2-chlorothiazol-5-yl ) ethyl group, and the like.
[ 0050]
Examples of the "C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms)" in the present compound include a (pyridin-5-yl ) methyl group, a ( 2-chloropyridin-5-yl ) methyl group, a 1- ( 2-chloropyridin-5-yl ) ethyl group, a (2- trifluoromethylpyridin-5-yl ) methyl group, and the like.
[ 0051]
Examples of the present compound include the following compounds: A compound represented by the formula (1-1) :
Figure imgf000054_0001
wherein
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9a-,
Rl represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one "or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a. C1-C3 alkoxy group optionally substituted by one or more halogen atoms ), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5a represents a C1-C6 alkyl group optionally substituted
99
by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atom, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms),
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR2 a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25 (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 0052]
A compound represented by the formula (1-2) :
Figure imgf000056_0001
wherein
A3 represents a nitrogen atom or =CR9b- (wherein R9b represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a ' cyclopropylmethyl group, R7b represents methyl group or a propargyl group,
R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-G6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 0053]
A compound represented by the formula (1-3) :
Figure imgf000057_0001
wherein
A represents a nitrogen atom or =CR - (wherein R represents a hydrogen atom or a halogen atom),
Rl represents an ethyl group or a' cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR 1b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof,
t 0054]
A compound re resented by the formula (1-4) :
Figure imgf000058_0001
wherein
A3 represents a nitrogen atom or =CR9b- (wherein R9b represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally, substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR3b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 0055]
A compound represented : by the formula (1-5):
Figure imgf000059_0001
wherein
R a represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms,
A3a represents a nitrogen atom or =CR9a-,
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and Ra are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms ) , -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22 . (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
Ra represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 0056]
A compound represented by- the formula (1-5) wherein R70a is a hydrogen atom or a C2-C6 alkoxyalkyl group,
A is a nitrogen atom or =CR -,
Rla is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and Ra are the same or different and each represents a halogen atom or a hydrogen atom,
R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22 represents a C1-C6 alkyl group optionally substituted by one or more' halogen atoms), _-S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom,
R9a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted ' by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n is 0, 1 or 2,
or an N-oxide thereof.
[ 0057] A compound represented by the formula (1-6) :
Figure imgf000063_0001
wherein
R70b represents a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms,
A3b represents a nitrogen atom or =CR9b- (wherein R9b represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
[ 0058] A compound represented by the formula (1):
Figure imgf000064_0001
A compound represented by the formula (1) wherein A1 R7-;
A compound represented by the formula (1) wherein . A1 oxygen atom;
A compound represented by the formula (1) wherein A1 sulfur atom;
A compound represented by the formula (1) wherein A2 R8-;
A compound represented by the formula (1) ; wherein A2 R8-, and A3 is a nitrogen atom;
A compound represented by the formula (1) wherein A2 R8-, and A3 is =CR9-;
A compound represented by the formula (1) wherein A1 R7-, and A2 is =CR8-;
A compound represented . by the formula (1) wherein A1 R7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (1) wherein A1 R7-, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (1) wherein A1 oxygen atom, and A2 is =CR8-; A compound represented by the formula (1) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (1) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the. formula (1) wherein A1 is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (1) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (1) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
[ 0059]
A compound represented by the formula (1) wherein R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X;
A compound represented by the formula (1) wherein R1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms;
[ 0060]
A compound represented by the formula (1) wherein R3 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group . Z, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(O)mRX0, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a . C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-.C3 alkoxy group optionally substituted by one or more halogen atoms), 6-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), a cyano group, a nitro group, a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R2 and R4 are the same or different each other and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R2 and R4 are the same or different each other and each represents a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R5 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, -S(0)mR10, -SF5, a halogen atom or . a hydrogen atom; A compound represented by the formula (1) wherein R5 is a -C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, -S(0")MR10, -SF5 or a halogen atom;
A compound represented by the formula (1) wherein R5 is a C1-C6 alkyl group optionally substituted by one or. more halogen atoms, -OR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)MR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -SF5 , or a halogen atom;
A compound represented by the formula (1) wherein when A1 is - R7-, R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5-membered heterocyclic group (wherein the 5-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 6-membered heterocyclic group (wherein the 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) or a hydrogen atom; A compound represented by the formula (1) wherein when A1 is -NR7- , R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- membered aromatic heterocyclic group (wherein the 5- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a C1-C6 alkyl group substituted by one 6-membered aromatic heterocyclic group (wherein the 6- membered aromatic heterocyclic group is ■ optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group;
A compound represented by the formula (1) wherein when A1 is -NR7-, R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms; a C1-C6 alkyl group substituted by one 5- membered aromatic heterocyclic group (wherein the 5- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents . selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one 6-membered aromatic heterocyclic group (wherein the 6- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms);
A compound represented by the formula (1) wherein when A1 is -NR7-, R7 is a C1-C6. alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) , a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group;
A compound -represented by the formula (1) wherein when A1 is -NR7-, R7 is a methyl group, an ethyl group, a propyl group, an allyl group, a propargyl group, a (2- chlorothiazol-5-yl ) methyl group, a ( 2-chloropyridin-5- yl ) methyl group, a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group; .
A compound represented by the formula (1) wherein A1 is -NR7-, and R7 is a hydrogen atom or a C2-C6 alkoxyalkyl ■ group;
A compound represented by the formula (1) wherein A1 is -NR7-, and R7 is a hydrogen atom, a methoxymethyl group, .an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group;
A compound represented by the formula (1) wherein when A2 is =CR8-, R8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A2 is =CR8-, R8 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one. or more halogen atoms), -S(0)mR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A2 is =CR8-, R8 is a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A2 is =CR8-, R8 is a hydrogen atom;
A compound represented by the formula (1) wherein when
A3 is =CR9-, R9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A3 is =CR9-, R9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR10 (wherein R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), a halogen atom or a hydrogen atom; [ 0061]
A compound represented by. the formula (1) wherein R1 is a C1-C6. alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-.C3 alkyl groups);
A compound represented by the formula (1) wherein R1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1) wherein R1 is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1) wherein R1 is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
A compound represented by the formula (1) wherein R1 is an ethyl group or a cyclopropylmethyl group;
A compound represented by the formula (1) wherein R1 is an ethyl group; A compound represented by the formula (1) wherein R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3- alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R0b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein R3 is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, -CF2CF3, CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -OCF3, -OCF2CF3, -SCF3, - S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, -S (0 ) 2CF2CF3., a 2- pyridyl group, a 5-trifluoromethyl-2-pyridyl group, a 2- pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1) wherein R3 is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, . an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, -CF2CF3, CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -OCF3, -OCF2CF3, -SCF3, - S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, -S (0 ) 2CF2CF3, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
[ 0062]
A compound represented by the formula (1) wherein R2 and R4 both are a. hydrogen atom; [ 0063]
A compound represented by the formula (1) wherein R5 is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1) wherein R5 is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1) wherein R5 is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a C1-C6 haloalkyl group), -S(0)mR23b (wherein. R23b is a. C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
A compound represented by the formula (1) wherein R5 is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a C1-C6 haloalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
A compound represented by the formula (1) wherein R5 is a C1-C6 perfluoroalkyl group, -OR10 (wherein R10 is a Cl- C6 perfluoroalkyl group) or -S(0)mR10 (wherein R10 is a Cl- C6 perfluoroalkyl group) ;
A compound represented by the formula (1) wherein R5 is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, - OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
[ 0064]
A compound represented by the formula (1) wherein when A1 is -NR7- , R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms ) ;
A compound represented by the formula (1) wherein when A1 is -NR7-, R7 is a methyl group, an ethyl group, a propyl group, an allyl group, a propargyl group, ( 2-chlorothiazol- 5-yl) methyl group, or, (2-chloropyridin-5-yl ) methyl group; A compound represented by the formula (1) wherein when A1 is -NR7-, R7 is a methyl group or a propargyl . group;
[ 0065]
A compound represented by the formula (1) wherein when A3 is =CR9-, R9 is a halogen atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A3 is =CR9-, R9 is a fluorine atom, a chlorine atom, a bromine atom, an iodine' atom or a hydrogen atom;
A compound represented by the formula (1) wherein when A3 is =CR9-, R9 is a fluorine atom or a hydrogen atom;
[ 0066]
A compound represented by the formula (1) wherein R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X,
R2, R3 and R4 are the same or different each other and each represents a C1-C6 ' chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected, from Group Z, -OR10, -S(0)mR10, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5 and R6 are the same or different each other and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, -S(0)raR10, -SF5 a halogen atom or a hydrogen atom,
when A1 is -NR7-, R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5-membered heterocyclic group (wherein the 5-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) , a C1-C6 chain hydrocarbon group substituted by one 6-membered heterocyclic group (wherein the 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) or a hydrogen atom,
when A2 is =CR8-, R8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom,
when A3 is =CR9-, R9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
[ 0067] A compound represented by the formula .(1) wherein, R1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2 and R4 are the same or different each other and each represents a halogen atom or a hydrogen atom,
R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), 6-membered aromatic heterocyclic group (wherein the aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR10, -S(0)mR10, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, -SF5 or a halogen atom, R6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom,
R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms,
when A1 is -NR7-, R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- membered. aromatic heterocyclic group (wherein the 5- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a C1-C6 alkyl group substituted by one 6-membered aromatic heterocyclic group (wherein the 6- membered aromatic heterocyclic group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group,
when A2 is =CR8-, R8 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(Q)mR10, a halogen atom or a hydrogen atom,
when A3 is =CR9-, R9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
[ 0068]
A compound represented by the formula (1-1) wherein Ala is -NR7a-;
A compound represented by the formula (1-1) wherein Ala is an oxygen atom;
A compound represented by the formula (1-1) wherein Ala is a sulfur atom;
A compound represented by the formula (1-1) wherein
Ala is -NR7a- , and A3a is a nitrogen atom;
A compound represented by the formula (1-1) wherein Ala is -NR7a- , and A3a is =CR9a- compound;
A compound represented by the formula (1-1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom; A compound represented by the formula (1-1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula (1-1) wherein Al is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (1-1) wherein
Al is a sulfur atom, and A3a is =CR9a- compound;
[ 0069]
A compound represented by the formula (1-1) wherein Rl is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1-1) wherein Rla is a C1-C6 -alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1-1) wherein Rla is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1-1) wherein Rla is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
A compound represented by the formula (1-1) wherein Rla is an ethyl group or a cyclopropylmethyl group;
A compound represented by the formula (1-1) wherein
Rla is an ethyl group;
A compound represented by the formula (1-1) wherein R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), ^S(0)mR21a (wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom;
A compound represented by the formula (1-1) wherein R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
A compound represented by the formula (1-1) wherein
R3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, - C F2C F2C F3 , -CF(CF3)2, -CF2CF2CF2CF3, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, S(0) 2C F2C F3 , a 2-pyridyl group, a 5-trifluoromethyl-2- pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-1) wherein R3a is methyl group, a fluoromethyl group, a difluoromethyl group, a. trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - C F2C F3 , CF2CF2CF3, -CF(CF3)2, -C F2C F2C F2C F3 , -OCF3, -OC F2C F3 , -SCF3, - S(0)CF3, -S(0)2CF3, - SC F2C F3 , -S(0)CF2CF3, -S (0 ) 2CF2CF3, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
[ 0070]
A compound represented by the formula (1-1) wherein R2a and R4a both are a hydrogen atom;
[ 0071]
A compound represented by the formula (1-1) wherein R5a .is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1-1) wherein R5a is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1-1) wherein R5a is a C1-C6 haloalkyl group, -OR2a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR3a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
A compound represented by the formula (1.-1) wherein R5a is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group) or -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2); A compound represented by the formula (1-1) wherein R5a is a C1-C6 perfluoroalkyl group, -OR22a (wherein R22a is a C1-C6 perfluoroalkyl group) or -S(0)mR23a (wherein R23a is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-1) wherein
R5 is a trifluoromethyl group., -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, - S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
[ 0072]
A compound represented by the formula (1-1) wherein when Ala is -NR7a- , R7a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted, by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms);
A compound represented by the formula (1-1) wherein when Ala is -NR7a-, Ra is a methyl group, an ethyl group, a propyl group, an allyl group, a propargyl group, (2- chlorothiazol-5-yl ) methyl group, or, ( 2-chloropyridin-5- yl) methyl group;
A compound represented by the formula (1-1) wherein when Ala is -NR7a-, R7a is a methyl group or a propargyl group;
[ 0073]
A compound represented by the formula (1-1) wherein when A3a is =CR9a-, R9a is a halogen atom or a hydrogen atom;
A compound represented by the formula (1-1) wherein when A3a is =CR9a-, R9a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-1) wherein when. A3a is =CR9a-, R9a is a fluorine atom or a hydrogen atom;
[ 0074]
A compound represented by the formula (1-2) wherein A3b is a nitrogen atom;
A compound represented by the formula (1-2) wherein A is =CR - compound;
[ 0075] -
A compound represented by the formula (1-2) wherein Rlb is an ethyl group;
A compound represented by the formula (1-2) wherein
R3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, . a trifluoromethyl group, - CF2CF3, -CF2CF2CF3, -CF(CF3)2, -C F2C F2C F2C F3 , -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, S(0)2CF2CF3, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-2) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group) , -S (0 ) mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5. or a halogen atom;
A compound represented by the formula (1-2) wherein R5b.is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23 (wherein R23b is a C1-C6 haloalkyl group, and m is 0,.1 or 2) or -SF5;
A compound represented by the formula' (1-2) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R2b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
A compound represented by the formula (1-2) wherein R5 is a G1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- G6 haloalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
A compound represented by the formula (1-2) wherein R5b is a C1-C6 perfluoroalkyl group, -OR22b (wherein R22b is a C1-C6 perfluoroalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-2) wherein R5b is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, - S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
A compound represented by the formula (1-2) wherein when A3b is =CR9b-, R9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-2) wherein when A3b is =CR9b-, R9 is a fluorine atom or a hydrogen atom;
[ 0076]
A compound represented by the formula (1-3) wherein A3b is a nitrogen atom;
A compound represented by the formula (1-3) wherein A3b is =CR9b- compound; [ 0077]
A compound represented by the formula (1-3) wherein Rlb is an ethyl group;
A compound represented by the formula (1-3) wherein R3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, -CF2CF2CF3, -CF(CF3)2, -C F2C F2C F2C F3 , -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, - SC F2C F3 , -S(0)CF2CF3,
S(0) 2C F2C F3 , a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-3) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1-3) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1-3) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom; A compound represented by the formula (1-3) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b.is a Cl- C6 haloalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
A compound represented by the formula (1-3) wherein
R5b is a C1-C6 perfluoroalkyl group, -OR22b (wherein R22b is a C1-C6 perfluoroalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-3) wherein R5b is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3,
S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
A compound represented by the formula (1-3) wherein when A3b is'=CR9b-, Rb is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-3) wherein when A3b is =CR9b-,.. R9b is a fluorine atom or a hydrogen atom;
[ 0078]
A compound represented by the formula (1-4) wherein A3b is a nitrogen atom;
A compound represented by the formula (1-4) wherein A3b is =CR9b- compound;
[ 0079] A compound represented by the formula (1-4) wherein Rlb is an ethyl group;
A compound represented by the formula (1-4) wherein R3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, -C F2C F2C F3 , -CF(CF3)2, - C F2C F2C F2C F3 , -O C F3 , -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, - SC F2C F3 , -S(0)CF2CF3, - S(0) 2C F2C F3 , a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-4) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0.)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1-4) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1-4) wherein R5 is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
A compound represented by the formula (1-4) wherein FTD is a C1-C6 haloalkyl group, -OR^ (wherein RZD is a Cl- C6 haloalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
A compound represented by the formula (1-4) wherein R5b is a C1-C6 perfluoroalkyl group, -OR22b (wherein R22b is a C1-C6 perfluoroalkyl group) or -S(0)ffiR23b (wherein R23b is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-4) wherein R5b is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3,
S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
A compound represented by the formula (1-4) wherein when A3b is =CR9b-, R9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-4) wherein when A3b is =CR9b-, R9b is a fluorine atom or a hydrogen atom;
[ 0080]
A compound represented by the formula (1-5) wherein
A3a is a nitrogen atom;
A compound represented by the formula (1-5) wherein A3a is =CR9a- compound;
[ 0081]
A compound represented by the formula (1-5) wherein R is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups) ;
A compound represented by the formula (1-5) wherein Rla is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1-5) wherein Rla is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups);
A compound represented by the formula (1-5) wherein Rla is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group or a cyclopropylmethyl group;
A compound represented by the formula (1-5) wherein
Rla is an ethyl group or a cyclopropylmethyl. group;
A compound represented by the formula (1-5) wherein Rla is an ethyl group;
A compound represented by the formula (1-5) wherein R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or substituents selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one . or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom;
A compound represented by the formula (1-5) wherein
R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R 1a . represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom;
A . compound represented by the formula (1-5) wherein R3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, . -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, S(0)2CF2CF3, a 2-pyridyl group, a 5-trifluoromethyl-2- pyridyl group, a 2-pyrimidinyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-5) wherein R3a is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, -CF2CF2CF3, -CF(CF3)2, -CF2CF2CF2CF3, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3, S(0)2CF2CF3, a fluorine atom, a chlorine atom, a bromine atom, art iodine atom or a hydrogen atom;
[ 0082]
A compound represented by the formula (1-5) wherein R2a and R4a both are a hydrogen atom;
[ 0083] A compound represented by the formula (1-5) wherein R5a is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1-5) wherein R5a is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1-5) wherein
R5a is a C1-C6 haloalkyl group, -OR22a (wherein R2 a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or a halogen atom;
A compound represented by the formula (1-5) wherein Ra is a C1-C6 haloalkyl group, -OR22 (wherein R22a is a Cl- C6 haloalkyl group) or -S(0)mR23 (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2);
A compound represented by the formula (1-5) wherein R5a is a C1-C6 perfluoroalkyl group, -OR2a (wherein R22a is a C1-C6 perfluoroalkyl group) or -S(0)mR23a (wherein R3a is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-5) wherein R5a is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, - S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
[ 0084]
A compound represented by the formula (1-5) wherein R70a is a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group;
[ 0085]
A compound represented by the formula (1-5) wherein when A3a is =CR9a-, R9a is a halogen atom or a hydrogen atom; ·
A compound represented by the formula (1-5) wherein when A3a is =CR9a-, R9a is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the. formula (1-5) wherein when A3 is =CR9a-, R9a is a fluorine atom or a hydrogen atom;
[ 0086]
A compound represented by the formula (1-6) wherein A3b is a nitrogen atom;
A compound represented by the formula (1-6) wherein
A3b is =CR9b- compound;
A compound represented by the formula (1-6) wherein Rlb is an ethyl group;
A compound represented by the formula (1-6) wherein R3b is a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, an ethyl group, an ethenyl group, an ethynyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, - CF2CF3, -CF2CF2CF3, -CF(CF3)2, . -C F2C F2C F2C F3 , -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, -S(0)CF2CF3,
S(0)2CF2CF3, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
[ 0087]
A compound represented by the formula (1-6) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23 is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom;
A compound represented by the formula (1-6) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group) , -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2) or -SF5;
A compound represented by the formula (1-6) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group), -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2 ) or a halogen atom;
A compound represented by the formula (1-6) wherein R5b is a C1-C6 haloalkyl group, -OR22b (wherein R22b is a Cl- C6 haloalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 haloalkyl group, and m is 0, 1 or 2); A compound represented by the formula (1-6) wherein R5b is a Cl-C-6 perfluoroalkyl group, -OR22 (wherein R22b is a C1-C6 perfluoroalkyl group) or -S(0)mR23b (wherein R23b is a C1-C6 perfluoroalkyl group) ;
A compound represented by the formula (1-6) wherein
R5b is a trifluoromethyl group, -CF2CF3, -CF2CF2CF3, -CF(CF3)2, -OCF3, -OCF2CF3, -SCF3, -S(0)CF3, -S(0)2CF3, -SCF2CF3, - S(0)CF2CF3, -S (0) 2CF2CF3, SF5, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;.
[ 0088]
A compound* represented by the formula (1-6) wherein R70b is a hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a 1- (methoxy) ethyl group or a 1- (ethoxy) ethyl group;
A compound represented by the formula (1-6) wherein when A3b is =CR9b-, R9b is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom;
A compound represented by the formula (1-6) wherein when A3b is =CR9b-, R9b is a fluorine atom or a hydrogen atom;
[ 0089]
A fused heterocyclic compound represented by the formula ( 1-7 ) :
Figure imgf000102_0001
wherein
A c represents -NR c-, an oxygen atom or a sulfur atom,
Ac represents a. nitrogen atom or =CR -,
A c represents a nitrogen atom or =CR -,
R represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Xc or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Yc,
R2c and R4c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c, -NR10cRllc, -CO2R10c, -C(O)R10c, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R3c represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a phenyl group optionally substituted by one or more atoms or groups selected from Group Zc, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Zc, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Zc, -OR10c, -S(O)mR10c, -NR10cRllc, -CO2R10c, -C(0)R c, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5c and R6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Xc, a phenyl group optionally substituted by one or more atoms or groups selected from Group Zc, a 5-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Zc, a 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Zc, -OR10c, -S(O)mR10c, -S (0 ) 2NR10cRllc, - NR10cRllc, -CO.2R10c, -C(O)R10c, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R7c represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Wc, -CO2R10c, -C(O)R10c, or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Yc,
R8c and R9c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c, -NR10cRllc, -CO2R10c, -C(O)R10c, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R10c and Rllc are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms or a hydrogen atom,
m represents 0, 1 or 2, and
n represents 0, 1 or 2.
wherein R5c and R6c do not represents a hydrogen atom at the same time, and in the -S(O)mR10c, R10c does not a hydrogen atom when m is 1 or 2,
Group Xc: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a hydroxy group and a halogen atom,
Group Yc: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms and a halogen atom,
Group Zc: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group - optionally substituted by one or more halogen atoms, a halogen atom, a cyano group and a nitro group,
Group Wc: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, hydroxy group, a halogen atom and a cyano group. [ 0090]
A compound represented by the formula (1-7) wherein Alc is -NR7c-;
A compound represented by the formula (1-7) wherein Alc is an oxygen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, Rc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a Cl- C6 chain hydrocarbon group substituted by one C1-C6 alkoxy group optionally substituted by one or more halogen atoms, or a cyclopropyl group;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, R7c is a methyl group, an ethyl group, a methoxymethyl group or an ethoxymethyl group;
[ 0091]
A compound represented by the formula (1-7) wherein A2c is a nitrogen atom;
A compound represented by the formula (1-7) wherein
A2c is =CR8c-;
A compound represented by the formula (1-7) wherein A2c is =CH-;
A compound represented by the formula (1-7) wherein A3c is a nitrogen atom; A compound represented by the formula (1-7) wherein
A3c is =CR9c-;
A compound represented by the formula (1-7) wherein A3c is a nitrogen atom or =CR9c-, and R9c is a halogen atom or a hydrogen atom;
[ 0092]
A compound represented by the formula (1-7) wherein A2c is =CR8c-, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein A2c is a nitrogen atom, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein A2c is =CR8c-, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein A^c is a nitrogen atom, AJC is a nitrogen atom;
A compound represented by the formula (1-7) wherein
A2c is =CR8c-, R8c is a hydrogen atom, A3c is a nitrogen atom;
[ 0093]
A compound represented by the formula (1-7) wherein Alc is -NRc-, A2c is =CR8c-, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, A2c is a nitrogen atom, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, A2c is =CR8c-, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is -NR/C-, A10 is =CR -, Rsc is a hydrogen atom, AJC is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, R7c is a methyl group, and A2c is =CR8c-, R8c is a. hydrogen atom, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is -NRc-, A2c is a nitrogen atom, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is an oxygen atom, and A2c is =CR8c-, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein Alc is an oxygen atom, and A2c is a nitrogen atom, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein Alc is an oxygen atom, and A2c is =CR8c-, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is an oxygen atom, and A2c is =CR8c-, R8 is a hydrogen atom, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein
Alc is an oxygen atom, and A2c is a nitrogen atom, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is =CR8c-, A3c is =CR9c-;
A compound represented by the formula (1-7) wherein A is a sulfur atom, and A is a nitrogen atom, A is =CR9c-;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is =CR8c-, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is =CR8c-, R8c is a hydrogen atom, A3c is a nitrogen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is a nitrogen atom, A3c is a nitrogen atom;
[ 00.94]
A compound represented by the formula (1-7) wherein Rlc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms;
A compound represented by the , formula (1-7) wherein Rlc is a C1-C6 alkyl group optionally substituted by one or more halogen atoms;
[ 0095]
A compound represented by the formula (1-7) wherein
R2c .and Rc are the same or different and each represents a hydrogen atom or a halogen atom, R3c is a C1-C6 chain hydrocarbon group optionally substituted . by one or more halogen atoms., -OR10c, a halogen atom or a hydrogen atom;
A compound represented by the formula (1-7) wherein R c and R c both are a hydrogen atom
, R3c is a -C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a halogen atom or a hydrogen atom;
A compound represented by the formula (1-7) wherein
R2c and R4c both are a hydrogen atom, R3c is a phenyl group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms, a 5-membered heterocyclic group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms or a 6-membered heterocyclic group optionally substituted by one or more halogen atoms or a C1-C3 alkyl group optionally substituted by one or more halogen atoms;
A compound represented by the formula (1-7) wherein
R2 , R3c and R4c is a hydrogen atom;
[ 0096]
A compound represented by the formula (1-7) wherein R5c and R6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S (0 ) mR10c, a halogen atom or a hydrogen atom;
A compound represented by the formula (1-7) wherein R5c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c or a halogen atom, R c is a hydrogen atom;
A compound represented by the formula (1-7) wherein R5c is a C1-C3 alkyl group substituted by one- or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, . a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfiny'l group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom, R6c is a hydrogen atom;
A compound represented by the formula (1-7) wherein Rlc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, R2c and R4c are the same or different and each represents a hydrogen atom or a halogen atom, R3c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, a halogen atom or a hydrogen atom, R5c and R6c are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c, a halogen atom or a hydrogen atom, Alc is -NR7c-, R7c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 chain hydrocarbon group substituted by one C1-C6 alkoxy group optionally substituted by one or more halogen atoms, or a cyclopropyl group, and A2c is =CH-, and A3c is a nitrogen atom or =CR c-, and R is a halogen atom or a hydrogen atom;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, an oxygen atom or a sulfur atom,, R7c is a Cl- C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6. chain hydrocarbon group substituted by one C1-C6 alkoxy group optionally substituted by one or more halogen atoms or a C1-C6- chain hydrocarbon group, A2c is =CR8c-, A3c is a nitrogen atom or =CR9c-, and R9c is a halogen atom or a hydrogen atom, Rlc is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, R2c and R4c are the same or different and each represents a halogen atom or a hydrogen atom, R3c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c, a halogen atom or a hydrogen atom, R5c is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10c, -S(O)mR10c or a halogen atom, R6c is a hydrogen atom, R10c is a C1-C6 alkyl group optionally substituted by one or more halogen atoms;
A compound represented by the formula (1-7) wherein Alc is -NR7c-, R7c is a C1-C6 alkyl group, A2c is =CR8c-, A3c is =CR9c-, and Rlc is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, R2c and R4c both are a hydrogen atom, R3c is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, a halogen atom or a hydrogen atom, R5c is a C1-C3 alkyl group substituted by one or more, fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, a C.1-C3 alkylsulfonyl - group substituted by one or more fluorine atoms or a halogen atom, R6c is a hydrogen atom;
A compound represented by the formula (1-7) wherein
Alc is -NR7c-, R7c is a C1-C6 alkyl group, A2c is =CR8c-, R8c is a hydrogen atom, A3c is a nitrogen atom, Rlc is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, R2c and R4c both are a hydrogen atom, R3c is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, a halogen atom or a hydrogen atom, R5c is a C1-C3 alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom, R6c is a hydrogen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is =CR8c-, A3c is =CR9c-, and Rlc is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, R2c and R4c both are a hydrogen atom , R3c is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, a halogen atom or a hydrogen atom, R5c is a C1-C3 alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom, R6c is a hydrogen atom;
A compound represented by the formula (1-7) wherein Alc is a sulfur atom, and A2c is =CR8c-, R8c is a hydrogen atom, A3c is a nitrogen atom, Rlc is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, R2c and R4c both are a hydrogen atom
, R3c is a C1-C3 alkyl group optionally substituted by one or more fluorine atoms, a halogen atom or a hydrogen atom, R5c is a C1-C3 alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or a halogen atom, R is a hydrogen atom;
[ 0097]
A compound represented by the formula (1-7) wherein Alc is -NR7c-, R7c is a methyl group, an ethyl group, a methoxymethyl group or an ethoxymethyl group, Rlc is a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, sec-butyl group, an- isobutyl group, tert-butyl group, cyclopropyl group, a trifluoromethyl group, 2 , 2 , 2-trifluoroethyl group, R2c and R4c both are a hydrogen atom
, R3c is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom or a hydrogen atom, R5c is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, a bromine atom or an iodine atom, R6c is a hydrogen atom;
[ 0098]
A fused heterocyclic compound represented by the formula ( 1-8 ) :
Figure imgf000116_0001
wherein
Ald represents -NR7d- or a sulfur atom,
A3d represents a nitrogen atom or =CR9d-,
Rld represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms,
R2d and Rd are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a halogen atom or a hydrogen atom, R3d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10d, a halogen atom or a hydrogen atom,
R5d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10d, -S(O)mR10d, a bromine atom or an iodine atom,
R7d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms,
R9d represents a halogen atom or a hydrogen atom,
R10d represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms,
m represents 0, 1 or 2, and
n represents 0, 1 or 2;
[ 0099] A compound represented by the formula (1-8) wherein Ald is -NR7d- ;
A compound represented by the formula (1-8) wherein Ald is a sulfur atom;
[ 0100]
A compound represented by the formula (1-8) wherein A3d is a nitrogen atom;
A compound represented by the formula (1-8) wherein A3d is =CR9d-;
[ 0101]
A compound represented by the formula (1-8) wherein Ald is -NR7d- or a sulfur atom, R7d is a methyl group, and A3d is a nitrogen atom;
A compound represented by the formula (1-8) wherein Ald is -NR7d- , and A3d is =CR9d-;
A compound represented by the formula (1-8) wherein Ald is a sulfur atom, and A3d is =CR9d-;
A compound represented by the formula (1-8) wherein Ald is -NR7d- , and A3d is a nitrogen atom;
A compound represented by the formula (1-8) wherein
Ald is a sulfur atom, and A3d is a nitrogen atom;
[ 0102]
A compound represented by the formula (1-8) wherein Rld is a C1-C3 alkyl group;
[ 0103] A compound represented by the formula (1-8) wherein R2d and R4d is a hydrogen atom, R3d is a chlorine atom, a bromine atom, a trifluoromethyl group or a hydrogen atom;
A compound represented by the formula (1-8) wherein R2d, R3d and R4d is a hydrogen atom;
[ 0104]
A compound represented by the formula (1-8) wherein R5d is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;
A compound represented by the formula (1-8) wherein
R5d is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;
[ 0105]
A compound represented by the formula (1-8) wherein Ald. is -NR7d- or a sulfur atom, R7d is a methyl group, and A3d is a nitrogen atom, Rld is an ethyl group, R2d and Rd are the same or different and each represents a halogen atom or a hydrogen atom, R3d is a trifluoromethyl group, a halogen atom or a hydrogen atom, R is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;
A compound represented by the formula (1-8) wherein Ald is -NR7d- , and R7d is a methyl group, and A3d is =CR9d-, and Rld is an ethyl group, R2d and R4d are the same or different and each represents a halogen atom or a hydrogen atom, R3d is a trifluoromethyl group, a halogen atom or a hydrogen atom, R5d is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;
A compound represented by the formula (1-8) wherein Ald is -NR7d-, and R7d is a methyl group or a hydrogen atom, A3d is a nitrogen atom, Rld is an ethyl group, R2d and R4d are the same or different and each represents a halogen atom or a hydrogen atom, R3d is a trifluoromethyl group, a halogen atom or a hydrogen atom, R is a C1-C3 chain hydrocarbon group substituted by one or more fluorine atoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one or more fluorine . atoms, a C1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;
A compound represented by the formula (1-8) wherein Ald is -NR7d- or a sulfur atom, R7d is a methyl group, and A3d is =CR9d-, and Rld is an ethyl group, R2d and R4d is a hydrogen atom, R3d is a chlorine atom, a bromine atom, a trifluoromethyl group or a hydrogen atom, R5d is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;
A compound represented by the formula (1-8) wherein' Ald is -NR7d- or a sulfur atom, R is a methyl group, and A3d is a nitrogen atom, Rld is an ethyl group, R2d and Rd is a hydrogen atom, R3d is a chlorine atom, a bromine atom, a trifluoromethyl group or a hydrogen atom, R5d is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;
[ 0106]
A compound represented. by the formula (1) wherein A1 is -NR.7-, an oxygen atom or a sulfur atom,
A2 is . =CR8-,
A3 is a nitrogen atom or =CR9-,
R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y,
R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a hydrogen atom,
R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, S(0)mR10, -NR10RU, -C02R10, -C (0) NR10Rn, -SF5, a cyano group, a halogen atom or a hydrogen atom,
R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6- membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z) or a hydrogen atom,
R8 and R9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, -NR10R , a cyano group, a halogen atom or a hydrogen atom,
R10 and. 'R11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom,
each m independently represents 0, 1 or 2, and
n represents 0, 1 or 2;.
[ 0107]
The production processes of the present compound are described below.
[ 0108]
The present compound and the intermediate compound thereof can be produced by, for example, the following (Production process 1) to (Production process 24).
[ 0109]
(Production process 1)
The present compound represented by the formula (1) wherein n is 1 or 2 can be produced by oxidizing the present compound wherein n is 0.
Figure imgf000123_0001
(1-n0) (1 -n1) (1-n2)
wherein the symbols are as defined in the formula (1) .
[ 0110]
The present compound represented by the formula (1-nl) wherein n is 1 can be produced by oxidizing the present compound (1-nO) wherein n is 0.
The oxidation reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic halogenated ' hydrocarbons such- as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.
Examples of the oxidant to be used in the reaction include sodium periodate and m-chloroperbenzoic acid.
The amount of the oxidant to be used in the reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the present compound (1-nO) .
The reaction temperature of the reaction is generally within a range of -20°C to 80°C. The reaction time of the reaction is generally within a range of 0.1 to 12 hours.
After the completion of the reaction, the present compound (1-nl) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, washing the organic layer with, optionally an agueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer. The isolated present compound (1-nl) can be further purified by chromatography, recrystallization, and the like.
[ 0111]
The present compound represented by the formula (l-n2) wherein n is 2 can be produced by reacting the present compound (1-nl) wherein n is 1 in the presence of an oxidant.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.
Examples of the oxidant to be used in the reaction include m-chloroperbenzoic acid and a hydrogen peroxide solution.
The amount of the oxidant to be used in the reaction is generally 1 to 4 moles, preferably 1 to 2 moles, relative to 1 mole of the present compound (1-nl).
The reaction temperature of the reaction is generally within a range of -20°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 12 hours.
After the completion of the reaction, the present compound (l-n2) can be isolated by post-treatments, for example, extracting the reaction mixture, with an organic solvent, washing the organic layer with, optionally an aqueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer. The isolated present compound (1-nl) can be further purified by chromatography, recrystallization, and the like. The isolated present compound (l-n2) can be further purified by chromatography, recrystallization, and the like..
[ 0112]
The present compound represented by the formula (l-n2) wherein n is 2 can be also produced in one step (one pot) by reacting the present compound (1-nO) wherein n is 0 in the presence of an oxidant.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. Examples of the oxidant to be used in the reaction include m-chloroperbenzoic acid and a hydrogen peroxide solution.
The reaction may be conducted in the presence of a catalyst. Examples of the catalyst to be used in the reaction include sodium tungstate.
The amount of the oxidant to be used in the reaction is generally 2 to 5 moles, preferably 2 to 3 moles, relative to 1 mole of the present compound (1-nO) .
The amount of the catalyst to be used. in the reaction is generally 0.01-0.5 moles relative to 1 mole of the present compound (1-nO) .
The reaction temperature of the reaction is generally within a range of 0°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 12 hours.
After the completion of the reaction, the present compound (l-n2) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, washing the organic layer with, optionally an aqueous solution of a reduction agent (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and then drying and concentrating the organic layer. The isolated present compound (l-n2) can be further purified by chromatography, recrystallization, and the like. [ 0113]
(Production process 2)
The present compound (1) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M2) or the intermediate compound (M18) to give the intermediate compound (M3), and then condensing the resultin intermediate compound (M3) within the molecule.
Figure imgf000127_0001
wherein the symbols are as defined in the formula (1) .
[ 0114]
The intermediate compound (M3) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M2) in the presence of a condensing agent .
The reaction is generally conducted . in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as "THF"), and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate, and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as N, N-dimethylformamide (hereinafter referred to as "DMF"), N-methylpyrrolidone (hereinafter referred to as "NMP"), 1 , 3-dimethyl-2- imidazolidinone, and dimethylsulfoxide (hereinafter referred to as "DMSO"); nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
Examples of the "condensing agent" to be used in the reaction include carbodiimides . such as l-ethyl-3- (3- dimethylaminopropyl ) carbodiimide hydrochloride (hereinafter referred to as "WSC") and 1 , 3-dicyclohexyl carbodiimide.
The reaction may be conducted in the presence of a catalyst. Examples of the "catalyst" used in the reaction include 1-hydroxybenzotriazol (hereinafter referred to as "HOBt " ) .
The amount of the intermediate compound (M2) to be used in the reaction is generally 0.5 to 2 moles relative to 1 mole of the intermediate compound (Ml) . The amount of the condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml) .
The amount of the catalyst to be used in the reaction is generally 0.01 to 1 moles relative to 1 mole of the intermediate compound (Ml).
The reaction temperature of the reaction is generally within a range of 0°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M3) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated intermediate compound (M3) can be further purified by recrystallization, chromatography, and the like.
[ 0115]
The intermediate compound (M3) can be also produced by reacting the intermediate compound (Ml) with the intermediate compound (M18) .
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as. acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
The reaction can be optionally conducted in the presence of a base. Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
The . amount of the intermediate compound (M18) to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (Ml) .
The reaction temperature of the reaction is generally within a range of -20°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M3) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M3) can be further purified by chromatography, recrystallization, and the like.
[ 0116]
The present compound (1) can be produced by condensing the intermediate compound (M3) within the molecule.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane , chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate, and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP., 1,3- dimethyl-2-imidazolidinone, and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
The reaction may be conducted in the presence of a condensing agent, an acid, a base or a chlorinating agent.
Examples of the condensing agent to be used in the reaction include acetic acid anhydride, trifluoroacetic acid anhydride, WSC, a mixture of triphenyl phosphine, a base, and carbon tetrachloride or carbon tetrabromide, a mixture of triphenyl phosphine and azodiesters such as diethyl azodicarboxylate. Examples of the acid to be used in the reaction include sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid; polyphosphoric acid; and the like.
Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2 , 6-lutidine, 1 , 8-diazabicyclo[ 5.4.0] - 7-undecene (hereinafter referred to as "DBU"), and 1,5- diazabicyclo[ 4.3.0] -5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as tripotassium phosphate, potassium carbonate, and sodium hydride.
Examples of the chlorinating agent to be used in the reaction include phosphorous oxychloride; and the like.
When a condensing agent is used in the reaction, the amount of the condensing agent is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3) .
When an acid is used in the reaction, the amount of the acid is generally 0.1 to 5 moles relative to 1 mole of the intermediate, compound (M3) .
When a base is used in the reaction, the amount of the base is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3).
When a chlorinating agent is used in the reaction, the amount of the chlorinating agent is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M3) .
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of .0.1 to 24 hours.
After the completion of the reaction, the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1) can be further purified by recrystallization, chromatography, and the like .
[ 0117]
The present compound (1) can be also produced in one step (one pot) by reacting the intermediate compound (Ml) with the intermediate compound (M2) in the presence of a condensing agent.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloro ethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, 1,3- dimethyl-2-imidazolidinone , and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
Examples of the condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3- dicyclohexyl carbodiimide .
The reaction may be conducted in the presence of a catalyst. Examples of the catalyst to be used, in the reaction include 1-hydroxybenzotriazol.
The amount of the intermediate compound (M2) to be used in the .reaction is generally 0.5 to. 2 moles relative to 1 mole of the intermediate compound (Ml) .
The amount of the condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml).
The amount of the catalyst to be used in the reaction is generally 0.01 to 1 moles relative to 1 mole of the intermediate compound (Ml).
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1) can be further purified by recrystallization, chromatography, and the like .
[ 0118]
The present compound (1) can be also produced in one step (one pot) by reacting the intermediate compound (Ml) with the intermediate compound (M18) .
The reaction is generally conducted in the presence or absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
The reaction may be conducted in the presence of a base. Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N, N-diisopropylethylamine; nitrogen- containing aromatic compounds such as pyridine and 4- dimethylaminopyridine; and the like.
The amount of the intermediate compound (M18) to be used; in the reaction is generally 1 to 3 moles relative to
1 mole of the intermediate compound (Ml) .
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (Ml).
The reaction temperature of the reaction is generally within a range of 20°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (1) can- be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (1) can be further purified by chromatography, recrystallization, and the like.
[ 0119] '
(Production process 3)
The present compound (P20) represented by the formula (1) wherein A1 is a sulfur atom, and A3 is a nitrogen atom can be produced by reacting the intermediate compound (M9) with the intermediate compound (M2) or the intermediate compound (M18) to give the intermediate compound (M14), and then reacting the resulting intermediate compound (M14) with a sulfating agent.
Figure imgf000137_0001
wherein the symbols are as defined in the formula (1) .
[ 0120]
The intermediate compound (M14) can be produced by reacting. the intermediate compound (M9) with the intermediate compound (M2).
The reaction is generally conducted in the presence or absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, N P, and DMSO; nitrogen-containing aromatic compounds such as pyridine. and quinoline; and mixtures thereof.
Examples of the dehydrating condensing agent to be used in the reaction include carbodiimides such as WSC, 1 , 3-dicyclohexylcarbodiimide, and BOP agents.
The amount of the intermediate compound (M2) to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M9) .
The amount of the dehydrating condensing agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M9) .
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M14) can be isolated by post-treatments, for' example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization, and the like. [ 0121]
The intermediate compound (M14) can be also produced by reacting the intermediate compound (M9) with the intermediate compound (M18) .
The reaction is generally conducted in the presence or absence of a solvent, and may be conducted in the presence of a base .
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such . as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; nitrogen-containing aromatic compounds such as pyridine and guinoline; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N, -diisopropylethylamine; nitrogen- containing aromatic compounds such as pyridine and 4- dimethylaminopyridine; and the like.
The amount of the intermediate compound (M18) to be used in the reaction is generally 1 to 3 moles . relative to 1 mole of the intermediate compound (M9) .
The amount of the base to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M9).
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M14) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M14) can be further purified by chromatography, recrystallization, and the like.
[ 0122]
The present compound (P20) can be produced by reacting the intermediate compound (M14) with a sulfating agent.
The reaction is generally conducted in the presence or absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butylmethyl ether, and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1 , 2-dichloroethane, and chlorobenzene ; aromatic hydrocarbons such as toluene, benzene, and xylene; nitriles such as acetonitrile; nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine, and quinoline;. and mixtures thereof.
Examples of the sulfating agent to be used in the reaction include phosphorus pentasulfide, Lawesson's reagent ( 2 , 4-bis- ( 4-methoxyphenyl ) -1 , 3-dithia-2 , 4- diphosphetane-2, 4-disulfide) ; and the like.
The amount of the sulfating agent to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M14) .
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of 1 to 24 hours.
After the completion of the reaction, the present compound (P20) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (P20) can be further purified by recrystallization, chromatography, and the like.
[ 0123]
(Production process 4)
The present compound (1) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M4) in the presence of an oxidant.
Figure imgf000142_0001
(M 1 ) wherein the symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF, and tert- butylmethyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane, and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, 1 , 3-dimethyl-2- imidazolidinone, and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.
The reaction may be conducted in the presence of an acid. Examples of the acid to be used in the reaction include sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid; polyphosphoric acid; and the like .
The reaction may be conducted in the presence of a sulfite. Examples of the sulfite to be used in the reaction include sodium hydrogen sulfite, and disodium sulfite.
Examples of the oxidant to be used in the reaction include oxygen, copper (II) chloride, DDQ; and the like.
The amount of the intermediate compound (M4) to be used in the reaction is generally 1 to 2 moles relative to 1 mole of the intermediate compound (Ml).
The amount of the acid to be used in the reaction is generally 0.1 to 2 moles relative to 1 mole of the intermediate compound (Ml) .
The amount of the sulfite to be used in the reaction is generally 1 to 5 moles relative to 1. mole of the intermediate compound (Ml) .
The amount of the oxidant to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (Ml) .
The reaction temperature of the reaction is generally within a range of 0°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (1) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1) can be further purified by recrystallization, chromatography, and the like.
[ 0124]
(Production process 5)
The present compound represented by the formula (1) wherein n is 0 can be produced by reacting the intermediate compound (M6) with the intermediate compound (M7) in the presence of a base.
Figure imgf000144_0001
(M 6) (1 ) n = 0
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; water; and mixtures thereof.
Examples of the base to be used in the reaction include, alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metal hydrides such as sodium hydride.
The amount of the intermediate compound (M7) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M6) .
The amount of the base to be used in' the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M6) .
The reaction temperature of the reaction is generally within a range of 0°C to 150°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
In reaction, V2 is preferably a fluorine atom or a chlorine atom. [ 0125]
(Production process 6)
The intermediate compound (M6) can be produced by reacting the intermediate compound (Ml) with the intermediate compound (M19) or the intermediate compound
(M39) to give the intermediate compound (M20), and then condensing the resulting intermediate compound (M20) within the molecule.
Figure imgf000146_0001
wherein V represents a halogen atom, and the other symbols are as defined in the formula (1) .
[ 0126]
The intermediate compound (M20) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M19) instead of the intermediate compound (M2 ) .
The intermediate compound (M20) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M39) instead of the intermediate compound (Ml8 ) .
The intermediate compound (M6) can be produced in the same manner as in Production process 2 except for using the intermediate compound (M20) instead of the intermediate compound (M3 ) .
The intermediate compound (M6) can be produced in one step (one pot) in the same manner as in Production process 2 except for using the intermediate compound (M19) instead of the intermediate compound (M6) .
The intermediate compound (M6) can. be produced in one step (one pot) in the same manner as in Production process 2 except for using the intermediate compound (M39) instead of the intermediate compound (M2).
In reaction, V2 is preferably a fluorine atom or a chlorine atom.
[ 0127]
(Production process 7)
The intermediate compound represented by the formula
(M3) wherein n is 0 can be produced by reacting the intermediate compound (M20) with the intermediate compound ( 7).
The present compound represented by the formula (1) wherein n is 0 can be produced by condensing the resulting intermediate compound (M3) within the molecule.
Figure imgf000148_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
[ 0128]
The intermediate compound represented by the formula (M3) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M20) instead of the intermediate compound (M6) .
The present compound represented by the formula (1) wherein n is 0 can be produced in the same manner as in Production process 2 except for using the intermediate compound represented by the formula (M3) wherein n is 0 instead of the intermediate compound (M3) .
The present compound represented by the formula (1) wherein n is 0 can be produced in one step (one pot) in the same manner as in Production process 5 except for using the intermediate compound (M20) instead of the intermediate compound (Μβ) . ·
In reaction, V2 is preferably a fluorine atom or a chlorine atom.
[ 0129]
(Production process 8)
The present compound represented by the formula (1) wherein n is 0 can be produced by reacting the intermediate compound (M8) or a disulfide thereof, the intermediate compound (M8 ' ) , with the intermediate compound (M17) in the presence of a base.
Figure imgf000149_0001
( 8 ')
wherein L is a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, N P, and DMSO; and mixtures thereof.
Examples of the base to be used in the reaction include inorganic bases such as alkali metal or alkaline earth metal hydrides, e.g., sodium hydride, potassium hydride, and calcium hydride; sodium carbonate; and potassium carbonate; and organic base such as triethylamine .
When the intermediate compound (M8 ' ) , which is a sulfide, is used, the reaction is generally conducted in the presence of a reductant.
Examples of the reductant to be used in the. reaction include sodium hydroxymethanesulfinate (trade name: Rongalite) .
The amount of the intermediate compound ( 17) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M8) .
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M8).
When the intermediate compound (M81 ) , which is a disulfide, is used, the amount of the intermediate compound (M17) to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the intermediate compound (M8 ' ) . The amount of the base to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the intermediate compound (M8 ' ) . The amount of the reductant to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M8 ' ) ·
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
[ 0130]
(Production process 9)
The present compound represented by the formul'a (1) wherein n is 0 can be produced by reacting the intermediate compound (M8 ' ) with the intermediate compound (M17'-l) or the intermediate compound (M17'-2).
Figure imgf000152_0001
(M 8 ') wherein V3 is a chlorine atom, a bromine atom, or an iodine atom, and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
The amount of the intermediate compound (M17'-l) to be used in the reaction is generally 1 to 2 moles relative to 1 mole of the intermediate compound ( 8 ' ) .
When the intermediate compound (M17'-2) is used, the intermediate compound (M17'-2) is generally used in an amount of 1 to 2 moles relative to 1 mole of the intermediate compound (M8 ' ) .
The reaction temperature of the reaction is generally within a range of -80°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (1) wherein n is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (1) wherein n is 0 can be further purified by chromatography, recrystallization, and the like.
[ 0131]
(Production process 10)
The intermediate compound (M8) can be produced by reacting the intermediate compound (M6) with a sulfating agent. The intermediate compound (M8 ' ) , which is a disulfide of the intermediate compound (M8), can be produced by oxidizing the intermediate compound (M8).
Figure imgf000153_0001
(Μ 8 ')
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
The intermediate compound (M8) can be produced in the same manner as in Production process 5 except for using sodium sulfide, sodium hydrogen sulfide, hydrogen sulfide or the like instead of the intermediate compound (M7) .
In this case, the reaction from the intermediate compound ( 8) to the intermediate compound (M81 ) is easily progressed, and thus the intermediate compound (M8 ' ) may be produced in the synthesis of the intermediate compound (M8)
In reaction, V2 is preferably a fluorine atom or a chlorine atom.
[ 0132]
The intermediate compound (M8 ' ) can be produced by reacting the intermediate compound (M8) with an oxidant.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include water; alcohols such as methanol and ethanol; ethers such as THF, ethylene glycol dimethyl ether, tert- butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; carboxylic acids such as acetic acid; and mixtures thereof.
Examples of the oxidant to be used in the reaction include oxygen, iodine,. hydrogen peroxide solution, potassium ferricyanide; and the like.
The amount of the oxidant to be used in the reaction is generally 0.5 to 10 moles relative to 1 mole of the intermediate compound ( 8).
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M8 ' ) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound. (M8 ' ) can be further purified by chromatography, recrystallization, and the like [ 0133]
(Production process 11)
The present compound (P3) represented by the formula
(1) wherein A1 is —NR71— can be produced by reacting the present compound (P2) represented by the formula (1) wherein A1 is —NH- with the intermediate compound (M10) in the presence of a base.
Figure imgf000155_0001
(P2) (P3)
wherein R71 is any of the groups for R7 other than a hydrogen atom in the formula (1), L is an leaving group such as a chlorine atom, a bromine atom, an iodine atom, a -trifluoromethanesulfonyloxy group and a methanesulfonyloxy group, and the other symbols are as defined in the formula ( 1 ) .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4-dioxane; . aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, N P, and DMSO; and mixtures thereof .
Examples of the base to be used in the reaction include alkali metal or alkaline earth metal hydride such as sodium hydride, potassium hydride, and calcium hydride; inorganic bases such as sodium carbonate, and potassium carbonate; organic bases such as triethylamine ; and the like .
The amount of the intermediate compound (M10) to be used in. the reaction is generally 1 to 5 moles relative to 1 mole of the present compound (P2) .
The amount of the base to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the present compound ( P2 ) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (P3) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (P3) can be further purified by chromatography, recrystallization, and the like.
[ 0134]
(Production process 12)
The intermediate compound (M2) can be produced by hydrolyzing the intermediate compound ( 37).
Figure imgf000157_0001
(M 37) (M 2)
wherein the symbols are as defined in the formula (1).
When the hydrolysis is conducted by using an acid, an aqueous solution of the acid is generally used as a solvent in the reaction.
Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M2) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization, and the like [ 0135]
When the hydrolysis is conducted by using a base, the reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, -dioxane; alcohols such as methanol and ethanol; water; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
The amount of the base to be used in the reaction is generally 1 to 10 moles, relative to 1 mole of the intermediate compound (M37) .
The reaction temperature of the reaction is generally within a range of 0°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M2) can be isolated by post-treatments, for example, acidifying the reaction solution, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M2) can be further purified by chromatography, recrystallization, and the like.
[ 0136]
(Production process 13)
The intermediate compound ( 18) can be produced by reacting the intermediate compound (M2) with a chlorinating agent .
Figure imgf000159_0001
(M 2)
wherein the symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent .
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4 -dioxane; aromatic hydrocarbons such as toluene and xylene; aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; and mixtures thereof.
Examples of the chlorinating agent to be used in the reaction include thionyl chloride, oxalyl dichloride, phosphorous oxychloride; and the like.
The amount of the chlorinating agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M2) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound ( 18) can be isolated by removing the solvent from the reaction mixture.
[ 0137]
(Production process 14)
The intermediate compound (M2) , the intermediate compound (M4) or the intermediate compound (M37) can be produced by reacting the intermediate compound (M7) with the intermediate compound (M19), the intermediate compound
(M22) or the intermediate compound (M36) , respectively, and optionally oxidizing the resulting compound.
Figure imgf000161_0001
(M 37) n = 0 (M 37) n = 1 , 2 wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1) .
[ 0138]
The intermediate compound (M2) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M19) instead of the intermediate compound (M6) .
The intermediate compound (M4) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M22) instead of the intermediate compound (M6).
The intermediate compound (M37) wherein n is 0 can be produced in the same manner as in Production process 5 except for using the intermediate compound (M36) instead of the intermediate compound (M6) .
[ 0139]
The intermediate compound (M2) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M2) wherein n is 0 instead of the present compound (1) wherein n is 0.
The intermediate compound (M4) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M4) wherein n is 0 instead of the present compound (1) wherein n is 0.
The intermediate compound (M37) wherein n is 1 or 2 can be produced in the same manner as in Production process 1 except for using the intermediate compound (M37) wherein n is 0 instead of the present compound (1) wherein n is 0.
In reaction, V2 is preferably a fluorine atom or a chlorine atom.
[ 0140]
(Production process 15)
The intermediate compound (M30) can be produced by nitrating the intermediate compound (M29) , or reacting the intermediate compound (M33) with the intermediate compound (M28). By reducing the resulting intermediate compound (M30), the intermediate compound (Ml) represented by the formula (Ml) wherein A1 is -NR7- can be produced.
Figure imgf000163_0001
(M 29)
wherein the symbols, are as defined in the formula
[ 0141]
The intermediate compound (M30) can be produced by reacting the intermediate compound (M33) with the intermediate compound (M28) in the presence of a base.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
The reaction may be conducted in the presence of a base .
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, and potassium carbonate; tertiary amines such as triethylamine and N, -diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4- dimethylaminopyridine .
The amount of the intermediate compound (M28) to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M33) .
The amount of the base to be used in the reaction is generally 0 to 10 moles relative to 1 mole of the intermediate compound (M6) .
The reaction temperature of the reaction is generally within a range of 0°C to 150°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the intermediate compound (M30) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization, and the like [ 0142]
The intermediate compound (M30) can be produced by reacting the intermediate compound (M29) with a nitrating agent .
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such . as dichloromethane, and chloroform; acetic acid, concentrated sulfuric acid, concentrated nitric acid, water; and mixtures thereof.
Examples of the nitrating agent to be used in the reaction include concentrated nitric acid; and the like.
The amount of the nitrating agent to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound (M29) .
The reaction temperature of the reaction is generally within a range of -10°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the . completion of the reaction, the intermediate compound (M30) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization, and the like.
The intermediate compound (M30) wherein R7 is a group other than a hydrogen atom can be produced in the same manner as in Production process 11 except for using the intermediate compound (M30) wherein R7 is a hydrogen atom instead of the present compound (P2) .
[ 0143] The intermediate compound (Ml) wherein A1 is -NR7- can be produced by reacting the intermediate compound (M30) with hydrogen in the presence of a hydrogenating catalyst.
The reaction is generally conducted in the presence of a solvent, under hydrogen atmosphere at 1 to 100 atm.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; water ; and mixtures thereof.
Examples of the hydrogenating catalyst to be used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
The amount of the hydrogen to be used in the reaction is generally 3 moles relative to 1 mole of the intermediate compound (M30 ) .
The amount of the hydrogenating catalyst to be used in the reaction is generally 0.001 to 0.5 moles relative to 1 mole of the intermediate compound (M30).
The reaction may be conducted in the presence of an acid or a base, if necessary.
Examples of the acid to be used in the reaction include acetic acid, hydrochloric acid, and the like.
Examples of the base to be used in the reaction include tertiary amines such as triethylamine; magnesium oxide; and the like.
The reaction temperature of the reaction is generally within a range of -20°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (Ml) wherein A1 is -NR7- can be isolated by post- treatments, for example, filtrating the reaction mixture, optionally extracting the reaction mixture with an organic solvent., and drying and concentrating the organic layer. The isolated intermediate compound (Ml) wherein A1 is -NR7- can be further purified by chromatography, recrystallization, and the like.
[ 0144]
As shown below, the intermediate compound (M30) can be produced by acetylating the intermediate compound (M29) to give the intermediate compound (M291), nitrating the resulting intermediate compound (Μ29') to give the intermediate compound (Μ30'), and hydrolyzing the resulting intermediate compound (M30 ' ) .
Figure imgf000167_0001
(M 29) (Μ 29') (Μ 30') (M 30) wherein the symbols are as defined in the formula (1) .
The intermediate compound (Μ29') can be produced by reacting the intermediate compound (M29) with an acylating agent .
The reaction is generally conducted in the presence of a solvent or using the acylating agent as a solvent.
Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, 4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the acylating agent to be used in the reaction include acetic acid anhydride, para- acetoxynitrobenzene; and the like.
The reaction may be conducted in the presence of a base.
Examples of the base to be used in the reaction include tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4 -dimethylaminopyridine .
The amount of the acylating agent to be used in the reaction is generally not less than 1 mole relative to 1 mole of the intermediate compound (M29) .
The amount of the base to be used in the reaction is generally 0.1 to 10 moles relative to 1 mole of the intermediate compound (M29) .
The reaction temperature of the reaction is generally within a range of 0°C to 150°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the intermediate compound (Μ29') can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M291) can be further purified by chromatography, recrystallization, and the like.
[ 0145]
The intermediate compound (Μ30') can be produced in the same manner as in Production process 15 except for using the^ intermediate compound (M291) instead of the intermediate compound (M29) .
[ 0146]
The intermediate compound (M30) can be produced by hydrolyzing the intermediate compound (M30 ' ) in the presence of an acid or a base.
[ 0147]
When the hydrolysis is conducted by using an acid, an aqueous solution of the acid is generally used as a solvent in the reaction.
Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid and sulfuric acid; and carboxyli.c acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M30) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recrystallization, and the like [ 0148]
When the hydrolysis is conducted by using a base, the reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; alcohols such as methanol and ethanol; water ; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; hydrazine; and the like.
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (Μ301)· The reaction temperature of the reaction is generally within a range of 0°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M30) can be isolated by post-treatments, for example, acidifying the reaction solution, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M30) can be further purified by chromatography, recryst.allization, and the like.
[ 0149]
(Production process 16)
The intermediate compound (Ml) wherein A1 is -NR7- can be produced by brominating the intermediate compound (M29) to give the intermediate compound (M35), and aminating the resulting intermediate compound (M35).
Figure imgf000171_0001
(M29) (M35) (M 1) A1 = -NR7- wherein the symbols are as defined in the formula
[ 0150]
The intermediate compound (M35) can be produced by reacting the intermediate compound (M29) with a brominating agent .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include, water; acetic acid; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such as ethyl acetate and butyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2- dichloro ethane; nitriles such as acetonitrile ; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof .
Examples of the brominating agent to be used in the reaction include N-bromosuccinimide, bromine, and the like.
The amount of the brominating agent to be used in the reaction is generally 1 to 3 moles relative to 1 mole of the intermediate compound ( 29) .
The. reaction temperature of the reaction is generally within a range of -10°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (M35) can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and concentrating the organic layer; pouring water to the reaction mixture, and collecting a solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated intermediate compound (M35) can be further purified by recrystallization, chromatography, and the like.
[ 0151]
The intermediate compound (Ml) wherein A1 is -NR7- can be produced by reacting the intermediate compound (M35) with an aminating agent in the presence of a copper compound.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include water; alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such as ethyl acetate and butyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1 , 2-dichloroethane; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof .
Examples of the aminating agent to be used in the reaction include ammonia, aqueous ammonia, lithium amide, and the like.
Examples of the copper compound to be used in the reaction include copper, · copper (I) iodide, copper (I) oxide, copper (II) oxide, acetylacetone copper (II), copper (II) acetate, copper (II) sulfate, and the like. The reaction may be conducted in the presence of a ligand. Examples of the ligand to be used in the reaction include acetylacetone , salen, phenanthroline, and the like.
The reaction may be conducted in the presence of a base.
Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1,5- diazabicyclo[ 4.3.0] -5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as tripotassium phosphate, potassium carbonate, cesium carbonate, and sodium hydroxide.
The amount of the aminating agent to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M35).
The amount of the copper compound to be used in the reaction is generally 0.02 to 0.2 moles relative to 1 mole of the intermediate compound (M35) .
The amount of the base to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the intermediate compound (M35).
The reaction temperature of the reaction is generally within a range of 30°C to 200°C. The reaction time of the reaction is generally within a range of 0.1 to 48 hours.
After the completion of the reaction, the intermediate compound (Ml) wherein A1 is -NR7- can be isolated by post- treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (Ml) wherein A1 is -NR7- can be further purified by chromatography, recrystallization, and the like.
[ 0152]
(Production process 17)
The intermediate compound (Ml) represented by the formula (Ml) wherein A1 is an oxygen atom can be produced by nitrating the intermediate compound (M31) to give the intermediate compound (M32), and reducing the resulting intermediate compound (M32) .
Figure imgf000175_0001
(M 31) (M 32) (M 1) A1 = -0- wherein the symbols are as defined in the formula (1) .
[ 0153]
The intermediate compound (M32) can be produced in the same manner as in Production process 15. except for using the intermediate compound (M31) instead of the intermediate compound (M29 ) .
The intermediate compound (Ml) wherein A1 is an oxygen atom can be produced in the same manner as in Production process 15 except for using the intermediate compound (M32) instead of the intermediate compound (M30) .
[ 0154]
(Production process 18)
The intermediate compound (Ml) represented by the formula (Ml) wherein A1 is a sulfur atom can be produced by reacting the intermediate compound (M33) with a sulfating agent to give the intermediate compound (M34), and reducing the resulting intermediate compound (M34).
Figure imgf000176_0001
(M 33) (M 34) (M 1) A1 = -S- wherein the symbols are as defined in the formula (1).
The intermediate compound (M34) can be produced by reacting the intermediate compound (M33) with . thiourea in the presence of a base.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; water; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydroxide such as sodium hydroxide and potassium hydroxide.
The amount of the thiourea to be used in the reaction is generally 0.5 to 3 moles relative to 1 mole of the intermediate compound (M33).
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (M33).
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound" (M34) can be isolated by post-treatments, for example, adding an acid to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (M34) can be further purified by chromatography, recrystallization, and the like.
[ 0155]
The intermediate compound (Ml) wherein A1 is a sulfur atom can be produced by reacting the intermediate compound (M34) with, a reductant.
The reduction reaction may be conducted in the presence of, for example, metal powder such as iron powder, and zinc powder; acids such as hydrochloric acid and acetic acid; and water.
The reaction is generally conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1, 4-dioxane; esters such as ethyl acetate and butyl acetate;, alcohols such as methanol and ethanol; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the reductant to be used in the reaction include, metal powders such as iron powders, zinc powders and tin dichloride powders.
The amount of. the metal powder to be used in the reaction is generally 3 to 10 moles relative to 1 mole of the intermediate compound ( 34) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the intermediate compound (Ml) wherein A1 is a sulfur atom can be isolated by post-treatments, for example, pouring water to the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (Ml) wherein A1 is a sulfur atom can be further purified by chromatography, recrystallization, and the like.
[ 0156]
(Production process 19)
The present compound' (P7) represented by the formula (1) wherein R5 is a C1.-C6 perfluoroalkyl group can be produced by reacting the present compound (P4) represented by the formula (1) wherein R5 is a halogen atom, the intermediate compound (Mil) or the intermediate compound (Mil') in the presence of a copper compound.
Figure imgf000179_0001
wherein V1 represents a halogen atom, Rf represents a C1-C6 perfluoroalkyl group, and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent .
Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the copper compound to be used in the reaction include copper, copper (I) iodide.
When the intermediate compound (Mil) is used, the amount of the intermediate compound (Mil) to be used in the reaction is- generally 1 to 10 moles relative to 1 mole of the present compound (P4) . 'The amount of the copper compound to be used in the reaction is generally 0.5 to 10 moles relative to 1 mole of the present compound (P4) . The reaction temperature of the reaction is generally within a range of 100°C to 200°C. The reaction time of the reaction is generally within a range of 0.5 to 48 hours.
When the intermediate compound. (Mil') is used, the reaction may be conducted in the presence of potassium fluoride. The amount of the intermediate compound (Mil') to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the present compound (P4). The amount of the copper compound to be used in the reaction is generally 0.1 to 10 moles relative to 1 mole of the present compound (P4). The amount of the potassium fluoride to be used in the reaction is generally 0.1 to 5 moles relative to 1 mole of the present compound (P4) .. The reaction temperature of the reaction is generally within a range of 0°C to 150°C. The reaction time of the reaction is generally within a range of 0.5 to 48 hours.
After the completion of the reaction, the present compound (P7) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
The isolated present compound (P7) can be further purified by chromatography, recrystallization, and the like.
In the reaction, V1 is preferably a bromine atom and an iodine atom.
[ 0157] (Production process 20)
The present compound (P9) wherein R5 is -SH can be produced by reacting the present compound (P4) with a sulfating agent. The intermediate compound (P91), which is a disulfide of the present compound (P9) , can be produced oxidizing the present compound (P9) .
Figure imgf000181_0001
(Ρ9 ')
wherein V1 represents a halogen atom, and the other symbols are as defined in the formula (1) .
The present compound (P9) can be produced by reacting the present compound (P4) with a thioesterifica.ting agent and a catalyst.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the thioesterificating agent to be used in the reaction include sodium sulfide, sodium sulfide 9- hydrate, and thiourea.
Examples of the catalyst to be used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
The reaction may be conducted in the presence of a ligand .
Examples of the ligand . to be used in the reaction include acetylacetone, salen, phenanthroline; and the like The reaction may be conducted in the presence of a base.
Examples of the base to be used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate; and organic bases triethylamine .
The amount of the thioesterificating agent to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (P4) .
The amount of the catalyst to be used in the reaction is generally 0.1 to 5 moles relative to 1 mole of the intermediate compound (P4) .
The amount of the ligand to be used in the reaction is generally 1 to 2 moles relative to 1 mole of the intermediate compound (P4).
The reaction temperature of the reaction is generally within a range of 50°C to 200°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the present compound (P9 can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (P9) can be further purified by chromatography, recrystallization, and the like.
In the reaction, V1 is preferably a bromine atom and an iodine atom.
In the reaction, the reaction from the present compound (P9) to intermediate compound (Ρ9') is easily progressed, and thus the intermediate compound (Ρ9') may be produced during the synthesis of the present compound (P9) .
[ 0158]
The intermediate compound (P9V) can be produced by reacting the present compound (P9) with an oxidant.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include water; alcohols such as methanol and ethanol; ethers such as THF, ethylene glycol dimethyl ether, tert- butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; carboxylic acids such as acetic acid; and mixtures thereof.
Examples of the oxidant to be used in the reaction include oxygen, iodine, hydrogen peroxide solution, potassium ferricyanide, and the like.
The amount of the oxidant to be used in the reaction is generally 0.5 to 10 moles relative to 1 mole of the intermediate compound (P9) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion1 of the reaction, the intermediate compound (Ρ9') can be isolated by post-treatments, for example,, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (Ρ9') can be further purified by chromatography, recrystallization, and the like
[ 0159]
The present compound ,(P9) can be produced by thioesterifying the present compound (P4) to give the intermediate compound (P9-1), and then hydrolyzing the resulting intermediate compound (P9-1).
Figure imgf000184_0001
wherein R ' is any of the groups other than a hydrogen atom for R10. in the formula (1), and the other symbols are as defined in the formula (1) .
The intermediate compound (P9-1) can be produced by reacting the present compound (P4) with a thioesterifying agent, in the presence of a base and a catalyst.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the thioesterifying agent to be used in the reaction include thiobenzoic acid, and the like.
Examples of the catalyst to be used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
The reaction may be conducted in the presence of a ligand .
Examples of the ligand to be used in the reaction include acetylacetone, salen, phenanthroline; and the like.
Examples of the base to be used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate; and organic bases such as triethylamine . The amount of the thioesterifying agent is generally 1 to 10 moles relative to 1 mole of the present compound (P4) .
The amount of the catalyst is generally 0.1 to 5 moles relative to 1 mole of the present compound (P4) .
The amount of the ligand is generally 0.1 to 5 moles relative to 1 mole of the present compound (P4) .
The amount of the base is generally 1 to 2 moles relative to 1 mole of the present. compound (P4) .
The reaction temperature of the reaction is generally within a range of 50°C to 200°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the intermediate Compound (P9-1) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
The isolated intermediate compound (P9-1) can be further purified by chromatography, recrystallization, and the like.
In the reaction, V1 is preferably a bromine atom and an iodine atom.
[ 0160]
The present compound (P9) can be produced by hydrolyzing the intermediate compound (P9-1).
When the hydrolysis is conducted in the presence of an acid, an aqueous solution of the acid -is generally used as a solvent. Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid.
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (P9) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic ; layer . The isolated present compound (P9) can be further purified by chromatography, recrystallization, and the like.
When the hydrolysis is conducted in the presence of a base, the reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; alcohols such as methanol and ethanol; water; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (P9.-1) .
The reaction temperature of the reaction is generally within a range of 0°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (P9) can be isolated by post-treatments, for example, acidifying the reaction solution, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (P9) can be further purified by chromatography, recrystallization, and the like.
In the reaction, the reaction . from the present compound (P9) to intermediate compound (P9\) is easily progressed, and thus the intermediate compound (Ρ9') may be produced during the synthesis of the present compound (P9) .
[ 0161]
(Production process 21)
The present compound (PlO-mO) wherein R5 is -S(0)mR10' and m is 0 can be produced by reacting the present compound (P9) or a disulfide thereof, the intermediate compound (Ρ9'), and the compound (M13). The present compound (P10) represented by the formula (1) wherein R5 is -S(0)mR10' and m is 1 or 2 can be produced by oxidizing the present compound (PlO-mO) wherein m is 0.
Figure imgf000189_0001
(Ρ9 ') (P10)m = 1,
wherein R ' is any of the groups other than a hydrogen atom for R10 in the formula (1), L is a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and a methanes.ulfonyloxy group, and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the base to be. used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride, calcium hydride; inorganic bases such as sodium carbonate and potassium carbonate; and organic bases such as triethylamine .
When the intermediate compound (Ρ9'), which is a disulfide, is used, the reaction is generally conducted in the presence of a reductant .
Examples of the reductant to be used in the reaction include sodium hydroxymethanesulfinate (trade name: Rongalite) .
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the present compound ( P9 ) .
When the intermediate compound (P91), which is a disulfide, is used, the amount of the intermediate compound (M13) to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the present compound (P91) . The amount of the base to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the present compound (P9) . The amount of the reductant to be used in the reaction is generally 1 to 5 moles relative to 1 mole of the present compound (P9) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (PlO-mO) wherein m is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (PlO-mO) wherein m is 0 can be further purified by chromatography, recrystallization, and the like.
[ 0162]
Among the present compounds (PlO-mO) wherein m is 0, the compound wherein R10 ' is a C1-C6 perfluoroalkyl group can be produced by reacting the intermediate compound (Ρ9'), perfluoroalkyl iodide and a reductant.
The reaction is generally conducted in the presence of a solvent .
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
Examples of the reductant to be used in the reaction include tetrakis (dimethylamino) ethylene .
Examples of the perfluoroalkyl iodide to be used in the reaction include trifluoromethane iodide, pentafluoroethane iodide, heptafluoro-2-iodopropane, and the like.
The amount of the perfluoroalkyl iodide to be used in the reaction is generally 2 to 10 moles relative to 1 mole of the intermediate compound (P91) .
The amount of the reductant to be used in the reaction is generally 1 to 5 moles relative to 1 . mole of the intermediate compound (P91 ) .
The reaction temperature of the reaction is generally within a range of -80°C to 50°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (PlO-mO) wherein m is 0 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (PlO-mO) wherein m is 0 can be further purified by chromatography, recrystallization, and the like.
[ 0163]
The present compound (P10) wherein m is 1 or 2 can be produced by reacting, the present compound (PlO-mO) wherein m is 0 with an oxidant.
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof. Examples of the oxidant to be used in the reaction include m-chloroperbenzoic acid and hydrogen peroxide solution..
The reaction may be conducted in the presence of a catalyst.
Examples of the catalyst to be used in the reaction include sodium tungstate.
The amount of oxidant is generally 1 to 5 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0.
The amount of catalyst is generally 0.01 to 0.5 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0.
In the production of the compound wherein m is 1, the amount of the oxidant is generally 0.8 to 1.2 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0. The amount of the catalyst to be used in the reaction is generally 0.05 to 0.2 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0.
In the production of the compound wherein m is 2, the amount of the oxidant is generally 1.8' to 5 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0. The amount of the catalyst to be used in the reaction is generally 0.05 to 0.2 moles relative to 1 mole of the present compound (PlO-mO) wherein m is 0. The reaction temperature of the reaction is generally within a range of -20°C to 120°C. The reaction time of the reaction is generally within a range of 0.1 to 12 hours.
After the completion of the reaction, the present compound (P10) wherein m is 1 or 2 can be isolated by post- treatments, for example, extracting the reaction mixture with an organic solvent, optionally washing the mixture with an aqueous solution of a reductant (e.g., sodium sulfite and sodium thiosulfate) , followed by an aqueous solution of a base (e.g., sodium hydrogen carbonate), and drying and concentrating the organic layer. The isolated present compound (P10) wherein m is 1 or 2 can be further purified by chromatography, recrystallization, and the like [ 0164]
(Production process 22)
The present compound (Pll) represented by the formula (1) wherein R5 is -OH can be produced via the intermediate compound (Pll1) from the present compound (P4).
Figure imgf000194_0001
wherein V1 represents a halogen atom, and the other symbols are as defined in the formula (1) .
The intermediate compound (Pll') can be produced by reacting the present compound (P4) with benzyl alcohol in the presence of a base.
The reaction is generally conducted in the presence of a solvent or used benzyl alcohol as a solvent.
Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as DMF, NMP, and DMSO; and mixtures thereof.
The reaction may be conducted in the presence of a catalyst.
Examples of the catalyst to be used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.
The reaction may be conducted in the presence of a ligand.
Examples of the ligand to be used in the reaction include acetylacetone, salen, phenanthroline; and the like.
The reaction is generally conducted in the presence of a base.
Examples of the base to be used in the reaction include inorganic bases such as potassium carbonate, cesium carbonate, and tripotassium phosphate.
The amount of the benzyl alcohol is generally 1 to 10 moles relative to 1 mole of the present compound (P4) .
The amount of the catalyst is generally 0.1 to 5 moles relative to 1 mole of the present compound (P4) .
The amount of the ligand is generally 0.1 to 5 moles relative to 1 mole of the present compound (P4) .
The amount of the base is generally 1 to 2 moles relative to 1 mole of the present compound (P4) .
The reaction temperature of the reaction is generally within a range of 50°C to 200°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the intermediate compound (ΡΙΙ') can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (ΡΙΙ') can be further purified by chromatography, recrystallization, and the like In the reaction, V1 is preferably a bromine atom and an iodine atom.
[ 0165]
The present compound (Pll) can be produced by reacting the intermediate compound (Pll') with hydrogen in the presence of a hydrogenating catalyst.
The reaction is generally conducted in the presence of a solvent under of hydrogen atmosphere at 1 to 100 atm.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; water; and mixtures thereof.
Examples of the hydrogenating catalyst to be used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
The amount of the hydrogen to be used in the reaction is generally 3 moles relative to 1 mole of the intermediate compound (Pll1) . .
The amount of the hydrogenating catalyst to be used in the reaction is generally 0.001 to 0.5 moles relative to 1 mole of the intermediate compound (Pll').
The reaction may be conducted in the presence of an acid or a base.
Examples of the acid to be used in the reaction include acetic acid, hydrochloric acid, and the like.
Examples of the base to be used in the reaction include tertiary amines such as triethylamine ; magnesium oxide; and the like.
The reaction temperature of the reaction is generally within a range of -20°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24. hours.
After the completion of the reaction, the present compound (Pll) can be isolated by post-treatments, for example, filtrating the reaction mixture, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound (Pll) can be further purified by chromatography, recrystallization, and the like.
[ 0166]
(Production process 23)
The present compound (P12) represented by the formula (1) wherein R5 is -OR10' can be produced by reacting the present compound (Pll) with the compound (M13).
Figure imgf000198_0001
(P11) (P12)
wherein R ' is any of the groups other than a hydrogen atom for R10 in the formula (1), and the other symbols are as defined in the formula (1) .
The reaction is generally conducted in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and 1 , 4 -dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as D F, NMP, and DMSO; and mixtures thereof.
Examples of the base to be used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride, calcium hydride; inorganic bases such as sodium carbonate and potassium carbonate; and organic bases such as triethylamine . The amount of the compound (M13) is generally 1 to 10 moles relative to 1 mole of the present compound (Pll).
The amount of the base is generally 1 to 10 moles relative to 1 mole of the present compound (Pll).
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.1 to 24 hours.
After the completion of the reaction, the present compound (P12) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer.
The isolated present compound (P12) can be further purified by chromatography, recrystallization, and the like.
[ 0167]
Among the present compounds (P12), the present compound (P12) wherein R10 ' is a trifluoromethyl group can be roduced by the following Production process.
Figure imgf000199_0001
(P11) (P11 ") (P12) R 0 '=CF3 wherein the symbols are as defined in the formula (1) . . The intermediate compound (Pll") can be produced by reacting the present compound (Pll), a base, carbon disulfide and a methylating agent.
The reaction is conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include aprotic polar -solvents such as DMF, NMP, and DMSO .
Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride.
Examples of the methylating agent to be used in the reaction include methyl iodide.
The amount of the base is generally ί to 2 moles relative to 1 mole of the present compound' (Pll) .
The amount of the carbon disulfide is generally 1 to 10 moles relative to 1 mole of the present compound (Pll) .
The amount of the methylating agent is generally 1 to
10 moles relative to 1 mole of the present compound (Pll) .
The reaction temperature of the reaction is generally within a range of 0°C to 100°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours.
After the completion of the reaction, the intermediate compound (Pll") can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated intermediate compound (Pll") can be further purified by chromatography, recrystallization, and the like. [ 0168]
Among the present compounds (P12), the present compound (P12) wherein R10 ' is a trifluoromethyl group can be produced by reacting the intermediate compound (Pll") with a fluorinating agent in the presence of a base.
The reaction is conducted in the presence of a solvent. Examples of the solvent to be used in the reaction include halogenated hydrocarbons such as dichloromethane , chloroform, carbon tetrachloride, and 1,2-dichloro ethane.
The reaction is conducted in the presence of a base and a fluorinating agent.
Examples . of the base to be used in the reaction include 1 , 3-dibromo-5 , 5-dimethyl hydantoin.
Examples of the fluorinating agent to be used in the reaction include tetra-n-butylammonium fluoride, and hydrogen fluoride pyridine complex.
The amount of the base to be used in the reaction is generally 1 to 10 moles relative to 1 mole of the intermediate compound (Pll").
The amount of the fluorinating agent is generally 1 to
10 moles relative to 1 mole of the intermediate compound (Pll") . .
The reaction temperature of the reaction is generally within a range of -80°C to 50°C. The reaction time of the reaction is generally within a range of 0.5 to 24 hours. After the completion of the reaction, the present compound (P12) wherein R10 ' is a trifluoromethyl group can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated present compound . (P12) wherein R101 is a trifluoromethyl group can be further purified by chromatography, recrystallization, and the like.
[ 0169]
(Production process 25)
An N-oxide having an oxidized nitrogen atom of. the present compound or the intermediate compound can be produced by reacting a compound having a nitrogen- containing heterocyclic group having a lone electron pair on the nitrogen atom with an oxidant.
Examples of the nitrogen—containing heterocyclic group to be used in the reaction include a pyridine ring.
The reaction can be conducted by, for example, a known method in the presence of a solvent such as halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene; alcohols such as methanol and ethanol; acetic acid; water; and the mixtures thereof, by using an oxidant such as m-chloroperbenzoic acid or hydrogen peroxide.
[ 0170] Examples of the intermediate compound (M3) include the following compounds.
[ 0171]
A compound represented by the formula (M3) wherein A1 is -NR7-;
A compound represented by the formula (M3) wherein A1 is an oxygen atom;
A compound represented by the formula (M3) wherein A1 is a sulfur atom;
A compound represented by the formula (M3) wherein A2 is =CR8-;
A compound represented by the formula (M3) wherein A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M3) wherein A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M3) wherein A1 is -NR7-, and A2 is =CR8-;
A compound represented by the formula (M3) wherein A1 is -NR7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M3) wherein A1 is -NR7-, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M3) wherein A1 is an oxygen atom, and A2 is =CR8-;
A compound represented by the formula (M3)' wherein' A1 is an oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom; A compound represented by the formula (M3) wherein A is an oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M3) wherein A is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (M3) wherein A is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M3) wherein A is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
[ 0172]
A compound represented by the formula (M3), which i: represented by the formula (M3-1) :
Figure imgf000204_0001
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M3-1) wherein Ala is -NR7a- ;
A compound represented by the formula (M3-1) wherein Ala is an oxygen atom;
A compound represented by the formula ( 3-1) wherein Ala is a sulfur atom;
A compound represented by the formula (M3-1) wherein Ala is -NR7a- , and A3a is a nitrogen atom;
A compound represented by the formula (M3-1) wherein Ala is -NR7a- , and A3a is =CR9a- compound;
A compound represented by the formula ( 3-1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom;
A compound represented by the formula (M3-1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented, by the formula (M3-1). wherein Ala is a sulfur atom, and A3 is a nitrogen atom;
A compound represented by the formula (M3-1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
[ 0173]
A compound represented by the formula (M3-1) , which is represented by the formula (M3-2):
the formula (M3-2)
Figure imgf000205_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M3-2) wherein A3b is a nitrogen atom;
A compound represented by the formula (M3-2) wherein A3b is =CR9b- compound;
[ 0174]
A compound represented by the formula (M3-1), which is represented by the formula (M3-3) :
Figure imgf000206_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M3-3) wherein A3b is a nitrogen atom;
A compound represented by the formula (M3-3) wherein
A3b is =CR9b- compound;
[ 0175]
A compound represented by the formula (M3-1), which is represented by the formula (M3-4):
Figure imgf000206_0002
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M3-4) wherein A3b is a nitrogen atom;
A compound represented by the formula (M3-4) wherein A3b is =CR9b- compound;
[ 0176]
Examples of the intermediate compound (M6) include the following compounds. ,
[ 0177] A compound represented by the formula (M6) wherein A1R7-;
A compound represented by the formula (M6) wherein A1 oxygen atom;
A compound represented by the formula (M6) wherein A1 sulfur atom;
A compound represented by the formula (M6) wherein A2R8-;
A compound represented by the formula (M6) wherein A2R8-, and A3 is a nitrogen, atom;
A compound represented by the formula (M6) wherein A2R8-, and A3 is =CR9-;
A compound represented by the formula (M6) wherein A1R7-, and A2 is =CR8-;
A compound represented by the formula (M6) wherein A1R7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M6) wherein A1R7-, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M6) wherein A1 oxygen atom, and A2 is =CR8-;
A compound represented by the formula (M6) wherein A1 oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M6) wherein A1 oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M6) wherein A1 is a sulfur atom, -and A2, is =CR8-;
A compound represented by the formula (M6) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M6) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
[ 0178]
A compound represented by the formula (M6) , which is re resented by the formula (M6-1) :
Figure imgf000208_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-1);
A compound represented by the formula (M6-1) wherein Ala is -NR7a- ;
A compound , represented by the formula (M6-1) wherein Ala is an oxygen atom;
A compound represented by the formula (M6-1) wherein Al is a sulfur atom;
A compound represented by the formula (M6-1) wherein Ala is -NR7a- , and A3a is a nitrogen atom;
A compound represented by the formula (M6-1) wherein Ala is -NR7a- , and A3a is =CR9a- compound;
A compound represented by the formula (M6-1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom; A compound represented by the formula (M6-1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula ( 6-1) wherein Ala is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (M6-1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
[ 0179]
A compound represented by the formula (M6-1), which is represented by the formula (M6-2):
Figure imgf000209_0001
wherein V2 represents a. halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (M6-2) wherein A3b is a nitrogen atom;
A compound represented by the formula (M6-2) wherein A3b is =CR9b- compound;
[ 0180]
A compound represented by the formula (M6-1), which is represented by the formula (M6-3) :
Figure imgf000209_0002
wherein V2 represents a halogen atom, and the other symbols are as defined. in the formula (1-2);
A compound represented by the formula (M6-3) wherein A3b is a nitrogen atom;
A compound represented by the formula (M6-3) wherein A3b is =CR9b- compound;
[ 0181]
A compound represented by the formula (Μβ-1), which is represented by the formula (M6-4) :
Figure imgf000210_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (M6-4) wherein A3b is a nitrogen atom;
A compound represented by the formula (M6-4) wherein A3b is =CR9 - compound;
[ 0182]
Examples of the intermediate compound (M8) and a disulfide thereof (M8 ' ) include the following compounds.
[ 0183]
A compound represented by the formula (M8) or (M81 ) wherein A1 is -NR7-;
A compound represented by the formula (M8) or (M81 ) wherein A1 is an oxygen atom; A compound represented by the formula (M8) or ( 81 ) wherein A1 is a sulfur atom;
A compound represented by the formula (M8) or (M8 ' ) wherein A2 is =CR8-;
A compound represented by the formula (M8) or (M81 ) wherein A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula" (M8) or (M81 ) wherein A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M8) or ( 8 ' ) wherein A1 is -NR7- , and A2 , is =CR8-;
A compound represented by the formula (M8) or (M8 ' ) wherein A1 is -NR7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M8) or (M8 ' ) wherein A1 is -NR7-,: A2 is =CR8-, and A3 is. =CR9-;
A compound represented by the formula (M8) or (M8 ' ) wherein A1 is an oxygen atom, and A2 is =CR8-;
A compound represented by the formula ( 8) or (M81 ) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M8) or (M8 ' ) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula ( 8) or (M8 ' ) wherein A1 is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (M8) or (M81 ) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen, atom;
A compound represented by the formula (M8) or (M8 ' ) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
[ 0184]
A compound represented by the formula (M8), which is represented by the formula (M8-1) :
Figure imgf000212_0001
wherein the symbols are as defined in the formula (1-1), or a compound represented by the formula (M81 ) , which is a disulfide thereof and represented by the formula (M8'-l) :
Figure imgf000212_0002
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M8-1) or (M8 ' - 1) wherein Ala is -NR7a- ;
A compound represented by the formula (M8-1) or (M81 - 1) wherein Ala is an oxygen atom;
A compound represented by the formula (M8-1) or (Μ8'- 1) wherein Ala is a sulfur atom;
A compound represented by the formula (M8-1) or (M8 ' - 1) wherein A a is -NR a-, and A is a nitrogen atom;
A compound represented by the formula (M8-1) or ( 8 ' - 1) wherein Ala is -NR7a- , and A3a. is =CR9a- compound;
A compound represented by the formula (M8-1) or (M8 ' - 1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom;
A compound represented by the formula ( 8-1) or ( 81- 1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula (M8-1) or (Μ8'- 1) wherein Ala is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (M8-1) or (Μ8'- 1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
[ 0185]
A compound represented by the formula (M8-1), which is represented by the formula (M8-2) :
Figure imgf000213_0001
wherein the symbols are as defined in the formula (1-2) or a compound represented by the formula (M8'-l), which is a disulfide thereof and represented by the formula (M8'-2):
Figure imgf000214_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M8-2) or (Μ8'- 2) wherein A3b is a nitrogen atom;
A compound represented by the formula (M8-2) or ( 8'- 2) wherein A3b is =CR9b- compound;
[ 0186]
A compound represented by the formula (M8-1), which is represented by the formula (M8-3) :
Figure imgf000214_0002
wherein the symbols are as defined in the formula (1-2) or a compound represented by the formula (M8'-l), which is a disulfide thereof and represented by the formula (M8'-3):
Figure imgf000214_0003
wherein the symbols are as defined in the formula (1-2) .
A compound represented by the formula (M8-3) or (M81 - 3) wherein A is a nitrogen atom;
A compound represented by the formula (M8-3) or (M8 ' - 3) wherein A3b is . =CR9b- compound;
[ 0187]
A compound represented by the formula (M8-1), which is represented by the formula (M8-4) :
Figure imgf000215_0001
wherein the symbols are as defined in the formula (1-2) or a compound represented by the formula (M8'-l), which is a disulfide thereof and represented by the formula (M8'-4): ■
Figure imgf000215_0002
wherein the symbols are as defined in the formula (1-2).
A compound represented by the formula (M8-4) or (M81- 4) wherein A3b is a nitrogen atom;
A compound represented by the formula (M8-4) or (M8 ' - 4) wherein A3b is =CR9b- compound;
[ 0188]
Examples of the intermediate compound (M20) include the following compounds.
[ 0189] A compound represented by the formula (M20) wherein A1R7-;
A compound represented by the formula (M20) wherein A1 oxygen atom;
A compound represented by the formula (M20) wherein A1 sulfur atom;
A compound represented by the formula (M20) wherein A2R8-;
A compound represented by the formula (M20) wherein A2R8-, and A3 is a nitrogen atom;
A compound represented by the formula (M20) wherein A2R8-, and A3 is =CR9-;
A compound represented by the formula (M20) wherein A1R7-, and A2 is =CR8-;
A compound represented by the formula (M20) wherein A1R7-, A2 is. =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M20) wherein A1R7-, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M20) wherein A1 oxygen atom, and A2 is =CR8-;
A compound represented by the formula (M20) wherein A1 oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M20) wherein A1 oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M20) wherein A1 is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (M20) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (M20) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (M20) wherein R2 and R4 is a hydrogen atom;
[ 0190]
A compound represented by the formula (M20) , which is represented by the, formula (M20-1) : ,
Figure imgf000217_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-1);
A compound represented by the formula (M20-1) wherein Ala is -NR7 - ;
A compound represented by the formula ( 20-1) wherein Ala is an oxygen atom;
A compound represented by the formula ( 20-1) wherein Ala is a sulfur atom;
A compound represented by the formula (M20-1) wherein Ala is -NR7a- , and A3a is a nitrogen atom;
A compound represented by the formula (M20-1) wherein Ala is -NR7a- , and A3a is =CR9a- compound;
A compound represented by the formula (M20-1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom;
A compound represented by the formula (M20-1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula (M20-1) wherein Ala is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (M20-1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
A compound represented by the formula (M20-1) wherein R2a and R4a is a hydrogen atom;
[ 0191]
A compound represented by the formula (M20-1), which is represented by the formula (M20-2):
Figure imgf000218_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (M20-2) wherein A3b is a nitrogen atom;
A compound represented by the formula (M20-2) wherein
A3b is =CR9b- compound;
[ 0192] A compound represented by the formula (M20-1), which is represented by the formula (M20-3) :
Figure imgf000219_0001
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (M20-3) wherein A3 is a nitrogen atom;
A compound represented by the formula (M20-3) wherein A3b is =CR9b- compound;
[ 0193]
A compound represented by the formula ( 20-1), which is represented by the formula (M20-4) :
Figure imgf000219_0002
wherein V2 represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (M20-4) wherein A3b is a nitrogen atom;
A compound represented by the formula (M20-4) wherein A3b is =CR9b- compound;
[ 0194]
As described above, the compound represented by the formula (P4) among the present compounds can be used as an intermediate in the production of the present compound. Examples of the present compound (P4) represented by the formula (1) include the following compounds.
[ 0195]
A compound represented by the formula (P4) wherein A1 is -NR7-;
A compound represented by the formula (P4) wherein A1 is an oxygen atom;
A compound represented, by the formula (P4) wherein A1 is a sulfur atom;
A compound represented by the formula (P4) wherein A2 is =CR8-;
A compound represented by the formula (P4) wherein A2 is =CR8-, and A3, is a nitrogen atom;
A compound represented by the formula (P4) wherein A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (P4) wherein A1 is -NR7-, and A2 is =CR8-;
A compound represented by the formula (P4) wherein A1 is -NR7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P4) wherein A1 is -NR7-, A2 is =CR8-, and A3 is =CR9-;
•a compound represented by the formula (P4) wherein A1 is an oxygen atom, and A2 is =CR8-; A compound represented by the formula (P4) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P4) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (P4) wherein A1 is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (P4) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P4) wherein A1 is a sulfur atom, A2 is =CR8-, and A3 is =CR9-;
[ 0196]
A compound represented by the formula (P4), which is represented by the formula (P4-1) :
Figure imgf000221_0001
wherein V1 represents a halogen atom, and the other symbols are as defined in the formula (1-1);
A compound represented by the formula (P4-1) wherein Ala is -NR7a- ;
A compound represented by the formula (P4-1) wherein Ala is an oxygen atom; .
A compound represented by the formula (P4-1) wherein Ala is a sulfur atom;
A compound represented by the formula (P4-1) wherein Ala is -NRa- , and A3a is a nitrogen atom;
A compound represented by the formula (P4-1) wherein Ala is -NR7a- , and A3 is =CR9a- compound;
A compound represented by the formula (P4-1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom;
A compound represented by the formula (P.4-1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula (P4-1) wherein Ala is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (P4-1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
[ 0197]
A compound represented by the formula (P4-1), which is represented by the formula (P4-2):
Figure imgf000222_0001
wherein V1 represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (P4-2) wherein A3b is a nitrogen atom;
A compound represented by the formula (P4-2) wherein
A3b is =CR9b- compound;
[ 0198]
A compound represented by the formula (P4-1), which is represented by the formula (P4-3):
Figure imgf000223_0001
wherein V represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by . the formula (P4-3) wherein A3b is a nitrogen atom;
A compound represented by the formula (P4--3) wherein A3b is =CR9b- compound;
[ 0199] :
A compound represented by the formula (P4-1), which is represented by the formula (P4-4):
Figure imgf000223_0002
wherein V represents a halogen atom, and the other symbols are as defined in the formula (1-2);
A compound represented by the formula (P4-4) wherein A3b is a nitrogen atom;
A compound represented by the formula (P4-4) wherein A3b is =CR9b- compound.
[ 0200]
As- described above, the compound represented by the formula (P9) among the present compounds can be used as an intermediate in the production of the present compound. The present compound (P9) represented by the formula (1) and a disulfide thereof (Ρ9') include the following compounds .
[ 0201]
A compound represented by the formula (P9) or the formula (Ρ9' ) wherein A1 is -NR7-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is an oxygen atom;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is a sulfur atom;
A compound represented by the formula (P9) or the formula (P91) wherein A2 is =CR8-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is -NR7-, and A2 is =CR8-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is -NR7-, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is -NR7-, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is an oxygen atom, and A2 is =CR8-;
A compound represented by the formula (P9) or the formula (P91) wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is an oxygen atom, A2 is =CR8-, and A3 is =CR9-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is a sulfur atom, and A2 is =CR8-;
A compound represented by the formula (P9) or the formula (Ρ9') wherein A1 is a sulfur atom, A2 is =CR8-, and
A3 is a nitrogen atom;
A compound represented by the formula (P9) or the formula (P91) wherein A1 is a sulfur atom, A2 is =CR8-, and
A3 is =CR9-;
[ 0202]
A compound represented by the formula (P9), which is represented by the formula (P9-1):
Figure imgf000225_0001
wherein the symbols are as defined in the formula (1-1), or a compound represented by the formula (Μ9'), which is a disulfide thereof and re resented by. the formula (M9'-l):
Figure imgf000226_0001
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is -NR7 - ;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is an oxygen atom;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is a sulfur atom;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is -NR7a-, and A3a is a nitrogen atom;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is -NR7a- , and A3a is =CR9a- compound;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is an oxygen atom, and A3a is a nitrogen atom;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is an oxygen atom, and A3a is =CR9a- compound;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is a sulfur atom, and A3a is a nitrogen atom;
A compound represented by the formula (P9-1) or (Ρ9'- 1) wherein Ala is a sulfur atom, and A3a is =CR9a- compound;
[ 0203] A compound represented by the formula (P9-1), which is represented by the formula (P9-2) :
Figure imgf000227_0001
wherein the symbols are as defined in the formula (1-2), a compound represented by the formula (M9'-l), which is disulfide thereof and represented by the formula (M9'-2):
Figure imgf000227_0002
wherein, the symbols are as defined in the formula (1-2).;
A compound represented by the formula (P9-2) or (Ρ9'- 2) wherein A3b is a nitrogen atom;
A compound represented by the formula (P9-2) or (P91- 2) wherein A3b is =CR9b- compound;
[ 0204]
A compound represented by the formula (P9-1), which is represented by the formula (P9-3) :
Figure imgf000227_0003
wherein the symbols are as. defined in the formula (1-2), or a compound represented by the formula ( 9'-l), which is a disulfide thereof and represented by the formula (M9'-3):-
Figure imgf000228_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (P9-3) or (P91- 3) wherein A3b is a nitrogen atom;
A compound represented by the formula (P9-3) or (Ρ9'- 3) wherein A3b is =CR9b- compound;
[ 0205]
A compound represented by the formula (P9-1), which is represented by the formula (P9-4) :
Figure imgf000228_0002
wherein the symbols are as defined in the formula (1-2), or a compound represented by the formula (M9'-l), which is a disulfide thereof and represented by the formula (M9'-4):
Figure imgf000228_0003
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (P9-4) or (Ρ9'- 4) wherein A3b is a nitrogen atom;
A compound represented by the formula (P9-4) or (Ρ9'- 4) wherein A3b is =CR9b- compound; [ 0206]
As described above, the compound represented by the formula (P2) among the present compounds can be used as an intermediate in the production of the present compound. The present compound (P2) represented by the formula (1) include the following . compounds .
[ 0207]
A compound represented by the formula (P2) wherein A2 is =CR8-;
A compound represented by the formula (P2) wherein A2 is =CR8-, and A3 is a nitrogen atom;
A compound represented by the formula (P2) wherein A2 is =CR8-, and A3 is =CR9-;
[ 0208]
A compound represented by the formula (P2), which is represented by the formula (P2-1) :
Figure imgf000229_0001
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (P2-1) wherein A3a is a nitrogen atom;
A compound represented by the formula (P2-1) wherein A3a is =CR9a- compound;
[ 0209] A compound represented by the formula (P2-1), which is represented by the formula (P2-2) :
Figure imgf000230_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (P2-2) wherein A3a is a. nitrogen atom;
A compound represented by the formula (P2-2) wherein A3a is =CR9a- compound;
[ 0210]
Examples of the intermediate compound (M2) include the following compounds .
[ 0211]
A compound represented by the formula (M2), which is represented by the formula (M2-1) :
Figure imgf000230_0002
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M2-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, n is 1 or 2;
A compound represented by the formula (M2-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, R3a is a trifluoromethyl group;
[ 0212]
A compound represented by the formula (M2-1), which is represented by the formula (M2-2):
Figure imgf000231_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M2-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, n is 1 or 2;
A compound represented by the formula (M2-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a trifluoromethyl group;
[ 0213]
Examples of the intermediate compound (M18) include the following compounds.
[ 0214]
A compound represented by the formula (M18), which is represented by the formula (M18-1):
Figure imgf000231_0002
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M18-1) wherein Rla is an ethyl group or a cyclopropylmethyl group;
[ 0215]
A compound represented by the formula (M18-1), which is represented by the formula (M18-2) :
Figure imgf000232_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M18-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a hydrogen atom;
A compound represented by the formula (M18-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a trifluoromethyl group;
[ 0216]
Examples of the intermediate compound (M4) include the following compounds.
[ 0217] , -
A compound represented by the formula (M4), which is represented by the formula (M4-1) :
Figure imgf000232_0002
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M4-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, R3a is a hydrogen atom;
A compound represented by the formula (M4-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, R3a is a trifluoromethyl group;
[ 0218]
A compound represented by the formula (M4-1), which is represented by the formula (M4-2):
Figure imgf000233_0001
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M4-2) wherein
Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a hydrogen atom;
A compound represented by the formula (M4-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a trifluoromethyl group;
[ 0219]
Examples of the intermediate compound (M37) include the following compounds.
[ 0220]
A compound represented by the formula (M37), which is represented by the formula (M37-1) :
Figure imgf000234_0001
wherein the symbols are as defined in the formula (1-1);
A compound represented by the formula (M37-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, n is 1 or 2;
A compound represented by the formula (M37-1) wherein Rla is an ethyl group or a cyclopropylmethyl group, R3a is a trifluoromethyl group;
[ 0221]
A compound represented by the formula ( 37-1), which is represented by the formula (M37-2) :
Figure imgf000234_0002
wherein the symbols are as defined in the formula (1-2);
A compound represented by the formula (M37-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, n is 1 or 2;
A compound represented by the formula (M37-2) wherein Rlb is an ethyl group or a cyclopropylmethyl group, R3b is a trifluoromethyl group.
[ 0222]
Next, specific examples of the present compound are described below.
The present compound is represented by the formul
Figure imgf000235_0001
wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . [ 0223] [ Table 1]
R1 ' A1 A3 n
Me NMe N 0
Me NMe N 1
Me NMe N .2
Et NMe N 0
Et NMe N 1
Et NMe N 2
Pr NMe N 0
Pr NMe N 1
Pr NMe N 2
iPr NMe N 0
iPr NMe N 1
iPr NMe N 2
tBu NMe N 0
tBu NMe N 1
tBu NMe N 2
CF3 NMe N o
CF3 NMe N 1 CF3 ' NMe N 2
CH2C F3 NMe N ■ 0
CH2C F3 NMe N 1
CH2C F3 NMe N 2
CH=CH2 NMe N 0
CH=CH2 NMe N 1
CH=CH2 NMe N 2
[ 0224] [ Table 2]
R1 A1 A3 n
CH2CH=CH2 NMe N 0
CH2CH=CH2 NMe N 1
CH2CH=CH2 NMe N 2
C≡CH NMe N 0
C≡CH NMe ' N 1
C≡CH NMe N 2
CH2C≡CH NMe N 0
CH2C≡CH NMe N 1
CH2C≡CH NMe N 2
CycPr NMe N 0
CycPr NMe N 1
CycPr NMe N 2
CH2CycPr NMe N 0
CH2CycPr NMe N 1
CH2CycPr NMe N 2
Me NMe CH 0
Me NMe CH 1
Me NMe CH 2
Et NMe CH . 0
Et NMe CH 1
Et NMe CH 2
Pr NMe CH 0
Pr NMe CH 1 2070409
236
Figure imgf000237_0001
[ 0225]
[ Table 3]
Figure imgf000237_0002
[ 0226]
[ Table 4]
R1 A1 A3 n CycPr NMe CH 0
CycPr NMe CH 1
CycPr NMe CH 2
CH2CycPr NMe CH 0
CH2CycPr NMe CH 1
CH2CycPr NMe CH 2
Me NMe CBr 0
Me NMe CBr 1
Me NMe CBr 2
Et NMe CBr 0
Et NMe CBr 1
Et NMe CBr 2
Pr NMe CBr 0
Pr NMe CBr 1
Pr NMe CBr 2 iPr NMe CBr 0 iPr NMe CBr 1 iPr NMe CBr 2 tBu NMe CBr 0 tBu NMe CBr 1 tBu NMe CBr 2
CF3 NMe CBr 0
CF3 NMe CBr 1
CF3 NMe CBr 2
[ 0227]
[ Table 5]
R1 A1 A3 n
CH2CF3 NMe CBr 0
CH2CF3 NMe CBr 1
CH2CF3 NMe CBr 2
CH=CH2 NMe CBr 0
CH=CH2 NMe CBr 1
CH=CH2 NMe CBr 2 12 070409
238
Figure imgf000239_0001
[ 0228]
[ Table 6]
R1 A1 A3 n
Me NH N 0
Me NH N 1
Me NH N 2
Et NH N 0
Et NH N 1
Et NH N 2
Pr NH N 0
Pr NH N 1
Pr NH N 2
iPr NH N 0
iPr NH N 1
iPr NH N 2
tBu NH N 0
tBu NH N 1
tBu NH N 2 2070409
239
Figure imgf000240_0001
[ 0229]
[ Table 7]
Figure imgf000240_0002
[ 0230] [ Table 8]
Figure imgf000241_0002
[ 0231] [ Table 9]
Figure imgf000241_0001
CH2CycPr NH CH 2
Me NH CBr 0
Me NH CBr 1
Me NH CBr 2
Et NH CBr 0
Et NH CBr 1
Et NH CBr 2
Pr NH CBr 0
Pr NH CBr 1
Pr NH CBr 2 iPr NH CBr 0 iPr NH CBr 1 iPr NH - CBr 2 tBu NH CBr 0 tBu NH CBr 1 tBu NH CBr 2
CF3 NH CBr 0CF3 NH CBr 1
CF3 NH CBr 2
[ 0232]
[ Table 10]
R1 A1 A3 n
CH2CF3 NH CBr 0
CH2CF3 NH CBr 1
CH2CF3 NH CBr 2
CH=CH2 NH CBr 0
CH=CH2 NH CBr 1
CH=CH2 NH CBr 2
CH2CH=CH2 NH CBr 0
CH2CH=CH2 NH CBr 1
CH2CH=CH2 NH CBr 2
C≡CH NH CBr 0
C≡CH NH CBr 1
C≡CH NH CBr 2
CH2C≡CH NH CBr 0
CH2C≡CH NH CBr 1
CH2C≡CH NH CBr 2 2012/070409
242
Figure imgf000243_0001
[ 0233]
[ Table
R1 A1 A3 n
Me N (CH2OMe) N 0
Me N(CH2OMe) N 1
Me N (CH2OMe) N 2
Et N (CH2OMe) N 0
Et N (CH2OMe) N 1
Et N(CH2OMe) N 2
Pr N (CH2OMe) N 0
Pr N (CH2OMe) N 1
Pr N (CH2OMe) N 2
iPr N (CH2OMe) N 0
iPr N(CH2OMe) N 1
iPr N(CH2OMe) N 2
tBu N (CH2OMe) N 0
tBu N (CH2OMe) N 1
tBu N (CH2OMe) N 2
CF3 . N(CH2OMe) N 0
CF3 N(CH2OMe) N 1
CF3 ' N (CH2OMe) N 2
CH2CF3 N (CH2OMe) N 0
CH2CF3 N(CH2OMe) N 1
CH2CF3 N (CH2OMe) N 2
CH=CH2 N (CH2OMe) N 0
CH=CH2 N (CH2OMe) N 1
CH=CH2 N (CH2OMe) N 2 [ 0234]
[ Table 12]
Figure imgf000244_0002
[ 0235]
[ Table 13]
Figure imgf000244_0001
iPr N (CH2OMe) CH 1 iPr N (CH2OMe) CH 2 tBu N(CH2OMe) CH 0 tBu N(CH2OMe) CH 1 tBu N (CH2OMe) CH 2
CF3 N (CH2OMe) CH 0
CF3 N (CH2OMe) CH 1
CF3 N (CH2OMe) CH 2
CH2CF3 N (CH2OMe) CH 0
CH2CF3 N (CH2OMe) CH 1
CH2CF3 N(CH2OMe) CH 2
CH=CH2 N (CH2OMe) CH 0
CH=CH2 N (CH2OMe) CH 1
CH=CH2 N(CH2OMe) CH 2
CH2CH=CH2 N(CH2OMe) CH 0
CH2CH=CH2 N (CH2OMe) CH 1
CH2CH=CH2 N (CH2OMe) CH 2
C≡CH N (CH2OMe) CH 0
C≡CH (CH2OMe) CH 1
C≡CH N (CH2OMe) CH 2
CH2C≡CH N(CH2OMe) CH 0
CH2C≡CH - - N (CH2OMe) CH 1
CH2C≡CH N(CH2OMe) CH 2
[ 0236] [ Table
R1 A1 A3 n
CycPr N (CH2OMe) CH 0
CycPr N (CH2OMe) CH 1
CycPr N(CH2OMe) CH 2
CH2CycPr N(CH2OMe) CH 0
CH2CycPr N ( CH2OMe) CH 1
CH2CycPr N (CH2OMe) CH 2
Me N(CH2OMe) CBr 0
Me N (CH2OMe) CBr 1
Me N (CH2OMe) CBr 2
Figure imgf000246_0001
[ 0237]
Figure imgf000246_0002
[ 0238]
[ Table 16]
Figure imgf000247_0002
[ 0239]
[ Table 17]
Figure imgf000247_0001
CycPr N(CH2OEt) 0
CycPr N (CH2OEt) N 1
CycPr N (CH2OEt) N 2
CH2CycPr N (CH2OEt) N 0
CH2CycPr N(CH2OEt) N 1
CH2CycPr N (CH2OEt) N 2
Me N (CH2OEt ) CH 0
Me N(CH2OEt) CH 1
Me N(CH2OEt) CH 2
Et N(CH2OEt) CH 0
Et N (CH2OEt) CH 1
Et N (CH2OEt) CH 2
Pr N (CH2OEt) CH 0
Pr N(CH2OEt) CH 1
Pr ' N (CH2OEt ) CH 2
[ 0240]
[ Table 18]
R1 A1 A3 n iPr N (CH2OEt ) CH 0 iPr N(CH2OEt) CH 1 iPr N(CH2OEt) CH 2 tBu N (CH2OEt) CH 0 tBu N(CH2OEt) CH 1 tBu N (CH2OEt) CH 2
CF3 - N (CH2OEt) CH 0
CF3 N (CH2OEt) CH 1
CF3 N (CH2OEt) CH 2
CH2CF3 N (CH2OEt) CH 0
CH2CF3 N (CH2OEt) CH 1
CH2CF3 N (CH2OEt) CH 2
CH=CH2 N (CH2OEt) CH 0
CH=CH2 N(CH2OEt) CH 1
CH=CH2 N(CH2OEt) CH 2
CH2CH=CH2 N (CH2OEt) CH 0
CH2CH=CH2 N(CH2OEt) CH 1
CH2CH=CH2 N (CH2OEt ) CH 2 C≡CH N (CH2OEt) CH 0
C≡CH N(CH2OEt) CH 1
C≡CH N(CH2OEt) CH 2
CH2C≡CH N (CH2OEt) CH 0
CH2C≡CH N (CH2OEt) CH 1
CH2C≡CH N(CH2OEt) CH 2
[ 0241] [ Table
R1 A1 A3 n
CycPr N (CH2OEt) CH 0
CycPr N(CH2OEt) CH 1
CycPr N(CH2OEt) CH . 2
CH2CycPr N (CH2OEt) CH 0
CH2CycPr N (CH2OEt ) CH 1
CH2CycPr . N (CH2OEt) CH 2
Me N(CH2OEt) CBr 0
Me N(CH2OEt) CBr 1
Me N(CH2OEt) CBr 2
Et N(CH2OEt) CBr 0
Et N (CH2OEt ) CBr 1
Et N (CH2OEt) CBr 2
Pr N (CH2OEt) CBr 0
Pr N (CH2OEt) CBr 1
Pr · N(CH2OEt) CBr 2 iPr N (CH2OEt ) CBr 0 iPr N (CH2OEt) CBr 1 iPr N(CH2OEt) CBr 2 tBu N (CH2OEt ) CBr 0 tBu N(CH2OEt) CBr 1 tBu N (CH2OEt ) CBr 2
CF3 N (CH2OEt) CBr 0
CF3 N(CH2OEt) CBr 1
CF3 N (CH2OEt)~ CBr 2 [ 0242]
[ Table 20]
Figure imgf000250_0001
[ 0243]
[ Table 21]
R1 A1 A3 n
Me N (CH2C≡CH) N 0
Me N (CH2C≡CH) N 1
Me N (CH2C≡CH) N 2
Et (CH2C≡CH) N 0 W
250
Figure imgf000251_0001
[ 0244]
[ Table 22]
R1 A1 A3 n
CH2CH=CH2 N(CH2C≡CH) N 0
CH2CH=CH2 N (CH2C≡CH) N 1
CH2CH=CH2 N(CH2C≡CH) N 2
C≡CH ( CH2C≡CH ) N 0
C≡CH (CH2C≡CH) N 1
C≡CH ( CH2C≡CH ) N 2
CH2C≡CH (CH2C≡CH) N 0
CH2C≡CH N (CH2C≡CH) N 1
CH2C≡CH (CH2C≡CH) N 2
CycPr N (CH2C≡CH) N 0
Figure imgf000252_0001
[ 0245]
[ Table 23]
R1 1 A3 n iPr N(CH2C≡CH) CH 0 iPr N (CH2C≡CH) CH 1 iPr (CH2C≡CH) CH 2 tBu N(CH2C≡CH) CH . 0 tBu N(CH2C≡CH) CH 1 tBu N(CH2C≡CH) CH 2
CF3 N (CH2C≡CH) CH 0
CF3 N (CH2C≡CH) CH 1
CF3 N(CH2C≡CH) CH 2
CH2CF3 N (CH2C≡CH). CH 0
CH2CF3 N(CH2C≡CH) CH r
CH2CF3 N(CH2C≡CH) CH 2
CH=CH2 N (CH2C≡CH) CH 0
CH=CH2 N.(CH2C≡CH) CH 1
CH=CH2 N (CH2C≡CH) CH 2
CH2CH=CH2 N (CH2C≡CH) . CH 0 CH2CH=CH2 N (CH2C≡CH) CH 1
CH2CH=CH2 N (CH2C≡CH) CH 2
C≡CH . N (CH2C≡CH) CH 0
C≡CH N (CH2C≡CH) CH 1
C≡CH (CH2C≡CH) CH 2
CH2C≡CH N(CH2C≡CH) CH 0
CH2C≡CH N (CH2C≡CH) CH 1
CH2C≡CH N(CH2C≡CH) CH 2
[ 0246]
[ Table 24]
R1 A1 A3 n
CycPr N (CH2C≡CH) CH 0
CycPr N(CH2C≡CH) CH 1
CycPr N (CH2C≡CH) CH 2
CH2CycPr N(CH2C≡CH) CH 0
CH2CycPr N ( CH2C≡CH ) CH 1
CH2CycPr N (CH2C≡CH) CH 2
Me N (CH2C≡CH) CBr 0
Me N (CH2C≡CH) CBr 1
Me N(CH2C≡CH) CBr 2
Et N (CH2C≡CH) CBr 0
Et N (CH2C≡CH) CBr 1
Et N(CH2C≡CH) CBr 2
Pr (CH2C≡CH) CBr 0
Pr N(CH2C≡CH) CBr 1
Pr N (CH2C≡CH) CBr 2 iPr (CH2C≡CH) CBr 0 iPr N(CH2C≡CH) CBr 1 iPr N (CH2C≡CH) CBr 2 tBu N (CH2C≡CH) CBr 0 tBu (CH2C≡CH) CBr 1 tBu (CH2C≡CH) CBr 2
CF3 N (CH2C≡CH) CBr 0 CF3 N(CH2C≡CH) CBr 1
CF3 N(CH2C≡CH) CBr 2
[ 0247]
[ Table 25]
Figure imgf000254_0001
[ 0248]
[ Table 26]
R1 A1 A3 n
Me 0 N 0
Me 0 N 1 Me 0 N 2
Et 0 N 0
Et 0 N 1
Et 0 N 2
Pr 0 N 0
Pr 0 N 1
Pr 0 N 2 iPr 0 N 0 iPr 0 N 1 iPr 0 N 2 tBu . 0 N 0 tBu 0 N 1 tBu 0 N 2
CF3 0 N 0
CF3 0 N 1
CF3 0 N 2
CH2CF3 0 N 0
CH2CF3 0 N 1
CH2CF3 0 N 2
CH=CH2 0 N 0
CH=CH2 0 N 1
CH=CH2 0 N 2
[ 0249]
[ Table 27]
R1 A1 A3 n
CH2CH=CH2 0 N o
CH2CH=CH2 0 N 1
CH2CH=CH2 0 N 2
C≡CH 0 N 0
C≡CH 0 N 1
C≡CH 0 ■ N 2
CH2C≡CH 0 N 0
CH2C≡CH 0 N 1 CH2C≡CH 0 N 2
CycPr 0 N 0
CycPr 0 N 1
CycPr 0 N 2
CH2CycPr 0 N 0
CH2CycPr 0 N 1
CH2CycPr 0 N 2
Me 0 CH 0
Me 0 CH 1
Me 0 CH 2
Et 0. CH 0
Et 0 CH 1
Et 0 CH 2
Pr 0 CH 0
Pr 0 CH 1
Pr 0 CH 2
[ 0250]
[ Table 28]
R1 A1 A3 n iPr 0 CH 0 iPr 0 CH 1 iPr 0 CH 2 tBu 0 CH 0 tBu 0 CH 1 tBu 0 CH 2
CF3 0 CH 0
CF3 0 CH 1
CF3 0 CH 2
CH2CF3 0 CH 0
CH2CF3 0 CH 1
CH2CF3 0 CH 2
CH=CH2 0 CH 0
CH=CH2 0 CH 1 CH=CH2 0 CH 2
CH2CH=CH2 0 CH 0
CH2CH=CH2 0 CH 1
CH2CH=CH2 0 CH 2
C≡CH 0 CH 0
C≡CH 0 CH 1
C≡CH 0 CH 2
CH2C≡CH 0 CH 0
CH2C≡CH 0 CH 1
CH2C≡CH 0 CH 2
[ 0251]
[ Table 29]
Figure imgf000257_0001
[ 0252]
[ Table 30]
Figure imgf000258_0001
[ 0253] [ Table 31]
R1 A1 A3 n
Me S N 0
Me S N 1
Me s N 2
Et s N 0
Et s N 1 W 201
258
Figure imgf000259_0002
[ 0254]
[ Table 32]
Figure imgf000259_0001
CycPr S N 2
CH2CycPr S N 0
CH2CycPr S N 1
CH2CycPr S N 2
Me S CH 0
Me S CH 1
Me S CH 2
Et S CH 0
Et S CH 1
Et S CH 2
Pr S CH o .
Pr S CH 1
Pr S CH 2
[ 0255]
[ Table 33]
R1 A1 A3 n iPr S CH 0 iPr s CH 1 iPr s CH 2 tBu s CH 0 tBu s CH 1 tBu s CH 2
CF3 s CH 0
CF3 s CH 1
CF3 s CH 2
CH2CF3 s CH 0
CH2CF3 s CH 1
CH2CF3 s CH 2
CH=CH2 s CH 0
CH=CH2 s CH 1
CH=CH2 s CH 2
CH2CH=CH2. s CH 0
CH2CH=CH2 s CH 1 CH2CH=CH2 S CH 2
C≡CH S CH . 0
C≡CH S CH 1
C≡CH S CH 2
CH2C≡CH S CH 0
CH2C≡CH S CH 1
CH2C≡CH S CH 2
[ 0256]
[ Table 34]
R1 A1 A3 n
CycPr S CH 0
CycPr S CH 1
CycPr s CH 2
CH2CycPr s CH 0
CH2CycPr s CH 1
CH2CycPr s CH 2
Me s CBr 0
Me s CBr 1
Me s CBr 2
Et s CBr 0
Et s CBr 1
Et s CBr 2
Pr s CBr 0
Pr s CBr 1
Pr s CBr 2 iPr s CBr 0 iPr s CBr 1 iPr s CBr 2 tBu s CBr 0 tBu s CBr 1 tBu s CBr 2
CF3 s CBr 0
CF3 s CBr 1 CF3 S CBr 2
[ 0257]
[ Table 35]
Figure imgf000262_0001
[ 0258]
In the above [ Table 1] to [ Table 35] , Me represents a methyl group, Et represents an ethyl group, Pr represents a n-propyl group, iPr represents isopropyl group, tBu represents a tert-butyl group, and CycPr represents cyclopropyl group.
[ 0259]
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by. the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in f Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented, by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in t Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group,, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to ■[ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group,. R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0260]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl . group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . -
A compound represented by the formula (A) wherein . R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . ·
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35]
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a pentafluoroethyl group, - and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3: and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by ' the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3; and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, . R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein . R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1]- to [ Table 35] .
[ 0261]
A compound represented by the formula (A) wherein R2,
R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] . -. .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a . methyl group, R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent . any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2. and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group,. R2 and R3 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2. and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a heptafluoroisopropyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0262]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1,. A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] . A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35]
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in. [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, . A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as. listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] . A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethoxy group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0263]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) . wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35]
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [. Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in t Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein -R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed, in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a. trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of .the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one. of the combinations as listed in [ Table 1] to [ Table 35] . ·.
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfanyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
t 0264]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35]
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and: n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed, in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented ;by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) . wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfinyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0265]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, . R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table -35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom,1 R5 is a trifluoromethylsulfonyl group, and R1, . A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R2 is a . trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl gr.oup, R2 and R4 are independently a hydrogen atom; R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, , R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] , to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0266]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by .the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and; R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a bromine atom, and. R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in. [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a bromine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0267]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom,. R5 is a iodine atom, and R1, . A1, A3 and n represent any one of the combinations as listed in [Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any. one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, R3 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in. [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is a iodine atom, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0268]
A compound represented by the formula (A) wherein R2, R3 and R4 are independently a hydrogen atom, R5 is -SF5, and R1,. A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a fluorine atom, R3 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . A compound represented by the formula (A) wherein R3 is a fluorine atom, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a fluorine atom, R2 and R3 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a chlorine atom, . R3 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and. n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a chlorine atom, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a chlorine atom, R2 and R3 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a bromine atom, R3 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a bromine atom, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [Table 35] .
A compound represented by the formula (A) wherein R4 is a bromine atom, R2 and R3 are independently a. hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a methyl group, R3 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of ' the combinations as listed in [ Table 1] to [ Table 35] .
A . compound represented by the formula (A) wherein R3 is a methyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a methyl group, R2 and R3 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R2 is a trifluoromethyl group, R3 arid R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R4 is a trifluoromethyl group, R2 and R3 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a trifluoromethoxy group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the* combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 3-chloro-2-pyridyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is a 2-pyrimidinyl group, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein R3 is -SF5, R2 and R4 are independently a hydrogen atom, R5 is -SF5, and R1, A1, A3 and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0269]
A compound represented by the formula (A) wherein A3 is =N(→0)-, R2 , R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R2 , R3 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R2 , R3 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(-→0)-, R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 . is a pentafluoroethyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R3 is a trifluoromethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] . A compound represented by the formula (A) wherein A3 is =N(→0)-, R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a pentafluoroethyl group, and R1, A1, " and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
A compound represented by the formula (A) wherein A3 is =N(→0)-, R3 is a pentafluoroethyl group, R2 and R4 are independently a hydrogen atom, R5 is a trifluoromethylsulfonyl group, and R1, A1, and n represent any one of the combinations as listed in [ Table 1] to [ Table 35] .
[ 0270]
Examples of pests on which the compound of the present invention exhibits a controlling effect include arthropod pests such as harmful insects and harmful mites, and more specifically, the following pests.
[ 0271]
Hemiptera :
Planthoppers ( Delphacidae ) such as small . brown planthopper {Laodelphax striatellus) , brown rice planthopper (Nilaparvata lugens) , and white-backed rice planthopper (Sogatella furcifera) ; leafhoppers
( Deltocephalidae ) such as green rice leafhopper (Nephotettix . cincticeps) , green , rice leafhopper {Nephotettix virescens) , and tea green leafhopper (Empoasca onukii) ; aphids (Aphididae) such as cotton aphid (Aphis gossypii) , green peach aphid [Myzus persicae) , cabbage aphid {Brevicoryne brassicae) , piraea aphid {Aphis spiraecola) , potato aphid (Macrosiphum euphorbiae) , foxglove aphid {Aulacorthum solani) , oat bird-cherry aphid (Rhopalosiphum padi) , tropical citrus aphid (Toxoptera citricidus) , and mealy plum aphid (Hyalopterus pruni) ; stink bugs ( Pentatomidae ) such as green stink bug (Nezara antennata) , bean bug {Riptortus clavetus) , rice bug {Leptocorisa chinensis) , white spotted spined bug {Eysarcoris parvus) , and stink bug (Halyomorpha mista) ; whiteflies (Aleyrodidae ) such as greenhouse whitefly (Trialeurodes vaporariorum) , sweetpotato whitefly (Bemisia tabaci) , silverleaf whitefly (Bemisia argentifolii) , citrus whitefly (Dialeurodes citri) , and citrus spiny white fly (Aleurocanthus spiniferus) ; scales (Coccidae) such as Calfornia red scale (Aonidiella aurantii) , San Jose scale (Comstockaspis perniciosa) , citrus north scale (Unaspis citri), red wax scale (Ceroplastes rubens), cottonycushion scale (Icerya purchasi) , Japanese mealybug (Planococcus kraunhiae) , Cosmstock mealybug ( Pseudococcus longispinis) , and white peach scale (Pseudaulacaspis pentagona) ; lace bugs (Tingidae) ; cimices such as Ci ex lectularius; psyllids ( Psyllidae ) ; etc.
[ 0272] Lepidoptera:
Pyralid moths (Pyralidae) such as rice stem borer {Chilo suppressalis) , yellow rice borer (Tryporyza incertulas) , rice leafroller {Cnaphalocrocis medinalis) , cotton leafroller {Notarcha derogata) , Indian meal moth {Plodia interpunctella) , oriental corn borer {Ostrinia furnacalis) , cabbage webworm {Hellula undalis) , and bluegrass webworm {Pediasia teterrellus) ; owlet moths (Noctuidae) such as common, cutworm (Spodoptera litura) , beet armyworm (Spodoptera exigua) , armyworm {Pseudaletia separata) , cabbage armyworm (Mamestra brassicae) , · black cutworm {Agrotis ipsilon) , beet semi-looper (Plusia nigrisigna) , Thoricoplusia spp., Heliothis spp . , and Helicoverpa spp.; white butterflies (Pieridae) such as common white (Pieris rapae) ; tortricid moths (Tortricidae ) such as Adoxophyes spp., oriental fruit moth [Grapholita molesta) , soybean pod borer (Leguminivora glycinivorella) , azuki bean podworm [Matsumuraeses azukivora) , summer fruit tortrix {Adoxophyes orana fasciata) , smaller tea tortrix (Adoxophyes honmai . ) , oriental tea tortrix (Homona magnanima) , apple tortrix (Archips fuscocupreanus) , and codling moth (Cydia pomonella) ; leafblotch miners (Gracillariidae) such as tea leafroller (Caloptilia theivora) , and apple leafminer (Phyllonorycter ringoneella) ; Carposinidae such as peach fruit moth {Carposina niponensis) ; lyonetiid moths (Lyonetiidae) such as Lyonetia spp.; tussock moths (Lymantriidae) such as Lymantria spp., and Euproctis spp.; yponomeutid moths (Yponomeutidae) such as diamondback (Plutella xylostella) ; gelechiid moths (Gelechiidae) such as pink bollworm ( Pectinophora gossypiella) , and potato tubeworm (Phthorimaea operculella) ; tiger moths and allies (Arctiidae) such as fall webworm {Hyphantria cunea) ; tineid moths (Tineidae) such as casemaking clothes moth {Tinea translucens) , and webbing clothes moth {Tineola bisselliella) ; etc.
[ 0273]
. Thysanoptera :
Thrips (Thripidae.) such as yellow citrus . thrips {Frankliniella occidentalis) , melon thrips {Thrips palmi) , yellow tea thrips { Scirtothrips dorsalis) , onion thrips {Thrips tabaci), flower thrips {Frankliniella intonsa) , etc t 02.74]
Diptera:
Culices such as common mosquito {Culex pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes -spp. such as yellow fever mosquito (Aedes aegypti), and Asian tiger mosquito {Aedes albopictus) ; Anopheles spp. such as Anopheles sinensis; chironomids (Chironomidae) ; house flies (Muscidae) such as Masca domestica, and Muscina stabulans; blow flies (Calliphoridae) ; flesh flies ( Sarcophagidae ) ; little house flies (Fanniidae); anthomyiid flies (Anthomyiidae ) such as seedcorn fly (Delia platura) , and onion fly (Delia antiqua) ; leafminer flies (Agromyzidae ) such as rice leafminer {Agromyza oryzae) , little rice leafminer {Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer [Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola) ; gout flies (Chloropidae) such as rice stem maggot (Chlorops oryzae); fruit flies (Tephritidae) . such as melon fly (Dacus cucurbitae) , - and Meditteranean fruit fly (Ceratitis capitata) ; Drosophilidae ; humpbacked flies (Phoridae) such as Megaselia spiracularis; moth flies ( Psychodidae) such as Clogmia albipunctata; Simuliidae; Tabanidae such as horsefly {Tabanus trigonus) ; stable flies, etc.
[ 0275] .
Coleoptera :
Corn root worms {Diabrotica spp.) such as Western corn root worm {Diabrotica virgifera virgifera) , and Sourthern corn root worm (Diabrotica undecimpunctata howardi) ; scarabs ( Scarabaeidae ) such as cupreous chafer [Anomala cuprea) , soybean beetle (Anomala rufocuprea) , and Japanese beetle (Popillia japonica); weevils such as maize weevil (Sitophilus zeamais) , rice water weevil (Lissorhoptrus oryzophilus) , azuki bean weevil {Callosobruchus chinensis) rice curculio {Echinocnemus squameus) , boll weevil (Anthonomus grandis) , and hunting billbug ( Sphenophorus venatus) ; darkling beetles (Tenebrionidae) such as yellow mealworm ( Tenebrio molitor) , and red flour beetle {Tribolium castaneum) ; leaf beetles (Chrysomelidae) such as rice leaf beetle [Oulema oryzae) , cucurbit leaf beetle (Aulacophora femoralis) , striped flea beetle (Phyllotreta striolata) , and Colorado potato beetle {Leptinotarsa decemlineata) ; dermestid beetles ( Dermestidae ) such . as varied carper beetle {Anthrenus verbasci) , and hide beetle (Deirmestes maculates) ; deathwatch beetles (Anobiidae) such as cigarette beetle (Lasioderma serricorne) ; Epilachna such as Twenty-eight-spotted ladybird (Epilachna vigintio.ctopunctata) ; bark beetles (Scolytidae) such as powder-post beetle {Lyctus brunneus) , and pine shoot beetle {Tomicus piniperda) ; false. powder-post beetles
(Bostrychidae) ; spider beetles (Ptinidae); longhorn beetles (Cerambycidae) such as white-spotted longicorn beetle {Anoplophora malasiaca) ; click beetles [Agriotes spp.); Paederus fuscipens, etc.
[ 0276]
Orthoptera :
Asiatic locust (Locusta migratoria) , African mole cricket [Gryllotalpa africana) , rice grasshopper {Oxya yezoensis) , rice grasshopper (Oxya japonica) , Gryllidae, etc.
[ 0277]
Shiphonaptera :
Cat flea {Ctenocephalides felis) , dog flea
{Ctenocephalides canis) , human flea {Pulex irritans) , oriental rat flea {Xenopsylla cheopis), etc.
[ 0278]
Anoplura:
Human body louse {Pediculus humanus corporis) , crab louse {Phthirus pubis), short-nosed cattle louse (Haematopinus eurysternus) , sheep louse {Dalmalinia ovis) , hog louse {Haematopinus . suis) , dog louse (Linognathus setosus ) , etc .
[ 0279]
Damalinia:
Sheep body louse (Dalmalinia ovis), cattle biting louse (Dalmalinia bovis), chicken louse ( enopon gallinae) , dog louse ( Trichodectes canis), cat louse (Felicola subrostrata) etc.
[ 0280]
Hymenoptera:
Ants (Formicidae) such as pharaoh ant {Monomorium pharaosis) , negro ant {Formica fusca japonica) , black house ant {Ochetellus glaber) , Pristomyrmex pungens, Pheidole noda, leaf-cutting ant {Acromyrmex spp.), and fire ant {Solenopsis spp.); hornets (Vespidae) ; bethylid wasps (Betylidae); sawflies (Tenthredinidae) such as cabbage sawfly {Athalia rosae) , and Athalia japonica, etc.
[ 0281]
Nematoda:
Rice white-tip nematode (Aphelenchoides besseyi) , strawberry bud nematode {Nothotylenchus acris) , southern root-knot nematode (Meloidogyne incognita) , northern root- knot nematode {Meloidogyne hapla) , Javanese root-knot nematode (Meloidogyne javanica) , soybean cyst nematode (Heterodera glycines) , potato cyst nematode (Globodera rostochiensis) , coffee root-lesion nematode (Pratylenchus coffeae) , California root-lesion nematode (Pratylenchus neglectus) , etc.
[ 0282]
Blattodea :
German cockroach (Blattella germanica) , smokybrown cockroach (Periplaneta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach (Blatta orientalis) ;
[ 0283]
Isoptera :
Termites such as Japanese subterranean termite (Reticulitermes speratus) , Formosan subterranean termite {Coptotermes formosanus) , western drywood termite (Incisiterm.es minor) , Daikoku drywood termite {Cryptotermes domesticus) , Odontotermes formosanus, Neotermes koshunensis , Glyptotermes satsumesis, Glyptotermes nakaj imai ,
Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis, Japanese dampwood termite {Hodotermopsis japonica) , Coptotermes guangzhoensis, Reticulitermes miyatakei, eastern subterranean termite {Reticulitermes flavipes amamianus) , Reticulitermes sp.f Nasutitermes takasagoesis, Pericapritermes nitobei, Sinocapritermes mushae, Reticuliterumes flavipes, Reticulitermes hesperus , Reticulitermes virginicus, Reticulitermes tibialis , Heterotermes aureus, and Zootermopsis nevadensis, etc.
[ 0284]
Acarina:
Spider mites (Tetranychidae) such as two-spotted spider mite {Tetranychus urticae) , Kanzawa spider mite {Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite {Panonychus ulmi) , and Oligonychus spp . ; eriophyid mites ( Eriophyidae ) such as pink citrus rust mite {Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite (Aculops lycopersici) , purple tea mite (Calacarus carinatus) , pink tea rust mite (Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite {Aculus schlechtendali) ; tarosonemid mites (Tarsonemidae ) such as broad mite {Polyphagotarsonemus latus); false spider mites (Tenuipalpidae) such as Brevipalpus phoenicis;
Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, American dog tick {Dermacentor variabilis) , Ixodes . ovatus, Ixodes persulcatus, black leg tick {Ixodes scapularis) , lone star tick (Amblyomma americanum) , Boophilus microplus, and Rhipicephalus sanguineus; Psoroptidae such as ear mite {Otodectes cynotis) ; itch mites ( Sarcoptidae ) such as Sarcoptes scabiei; folicle mites ( Demodicidae ) such as dog folicle mite {Demodex canis) ; acarid mites (Acaridae) such as mold mite {Tyrophagus putrescentiae) , and Tyrophagus similis; house dust mites ( Pyroglyphidae ) such as Dermatophagoides farinae, and Dermatophagoides ptrenyssnus; cheyletide mites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei; parasitoid mites ( Dermanyssidae ) such as tropical rat mite {Ornithonyssus bacoti) , northern fowl mite {Ornithonyssus sylviarum) , and poultry red mite {Dermanyssus gallinae) ; chiggers (Trombiculidae) such as Leptotrombidium akamushi; spiders (Araneae) such as Japanese foliage spider {Chiracanthium japonicum) , redback spider (Latrodectus hasseltii) , etc.
Chilopoda: house centipede (Thereuonema hilgendorfi) , Scolopendra subspinipes, etc.; Diplopoda: garden millipede (Oxidus gracilis) , Nedyopus tambanus, etc.;
Isopoda: common pill bug {Armadillidium vulgare) , etc . ;
Gastropoda: Li ax marginatus, Limax flavus, etc.
[ 0285]
The pest control agent of the present invention comprises the present compound and . an inert carrier. The pest control agent of the present invention generally comprises the present compound in combination with a solid carrier, a liquid carrier and/or a gaseous carrier, and if necessary, a surfactant or other formulation additives and takes the form of emulsifiable concentrate, oil solution, dusts, granules, wettable powder, suspension concentrate, microcapsules, aerosol, smoking agent, poison bait, resin formulation, shampoo formulation, paste, foam, carbon dioxide gas formulation, tablet or the like. The pesticidal composition of the present invention may be processed into mosquito coil, electric mosquito mat, electric mosquito liquid, smoking agent, fumigant, sheet, spot-on pesticide, or oral pesticide, and then be used.
The pesticidal composition of the present invention generally contains 0.01 to 95% by weight of the compound of the present invention.
[ 0286] Examples of the solid carrier to be used for formulation include a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay) , synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica), and chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) as well as synthetic resins (e . g ., polypropylene , polyacrylonitrile, polyester resins such . as methyl polymethacrylate and polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymer) .
[ 0287]
Examples of the liquid carrier include water, alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, and phenoxyethanol ) , ketones (e.g., acetone, methyl ethyl ketone, and cyclohexanone ) , aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, and methylnaphthalene) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosine, and light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, and propyleneglycol monomethyl ether acetate), nitriles (e.g., acetonitrile and isobutyronitrile) , ethers (e.g., diisopropyl ether, 1,4- dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, and 3-methoxy-3-methyl-l-butanol ) , acid amides (e.g., N, -dimethylformamide and N,N- dimethylacetamide) , halogenated hydrocarbons (e.g., dichloromethane, trichloroethane , and tetrachlorocarbon) , sulfoxides (e.g., dimethylsulfoxide ) , propylene carbonate, and vegetable oils (e.g., soy bean oil and cotton seed oil) [ 0288]
Examples of the gaseous carrier include fluorocarbons , butane gas, liquefied petroleum gas (LPG) , dimethyl ether, and carbon dioxide.
[ 0289]
Examples of the surfactant include nonionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, and polyethyleneglycol fatty acid ester; and anionic surfactant such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, and alkylsulfuric acid salts .
[ 0290]
Examples of the other formulation additives include binders, dispersants, colorants and stabilizers, and particularly for example, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acid), PAP (acidic isopropyl phosphate), BHT (2, 6-di-t-butyl-4-methylphenol) , and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol ) .
[ 0291]
Examples of a base material for the resin formulation include vinyl chloride polymers, and polyurethane . To the base material, if necessary, a plasticizer such as phthalate (e.g., dimethyl phthalate, dioctyl phthalate, etc.), adipate, stearic acid or the like may be added. The resin formulation is prepared by kneading the compound of the present invention into the. base material, using a conventional kneader, followed by molding such as injection molding, extrusion molding, press molding or the like. The resulting resin formulation may be formed into the shape of a plate, a film, a tape, a net, a string or the like via a further step of molding, cutting, or the like, if necessary. These resin formulations may be used, for example, the form of an animal collar, an animal ear tag, a sheet, a lead, or a horticultural post.
Examples of a base material of the poison bait include cereal powder, vegetable oil, sugar, and crystalline cellulose. To the base material, if necessary, an antioxidant such as dibutylhydroxytoluene . or nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent for preventing children or pets from erroneously eating such as hot pepper powder, a pest-attractive . perfume such as cheese perfume, onion perfume- or peanut oil or the like may be added.
[ 0292]
The method for controlling a pest of the present invention is applying an effective amount of the present compound to a pest directly and/or a habitat of a pest (e.g., plant,, soil, indoor, and in-body of animals). The present compound is generally used as the pest control agent of the present invention in the method for controlling pests of the present invention.
[ 0293]
When the pest control agent of the present invention is used for a control of pests in agriculture, the application amount is usually 1 to 10,000 g as the present compound per 10, 000 m2. When the pest control agent of the present invention is a formulation of emulsion, wettable powder or flowable, it is generally applied after a dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm. When the pest control agent of the present invention is a formulation of granules or dusts, they are generally applied as such.
[ 0294]
The formulations and the dilute aqueous solutions of the formulation may be sprayed directly to the plant to be protected from pests, or may be applied to the soil to control the pests living in a soil.
[ 0295]
Furthermore, the resin formulation of sheet or strip form can be applied by a method such as winding around plants, stretching in the vicinity of plants, and laying on the soil surface at the plant bottom.
[ 0296]
When the pest control agent of the present invention is used for a control of pests in indoor, the application amount is usually 0.01 to 1,000 mg as the present compound per 1 m2 in case of application for plane surface, and 0.01 to 500 mg as the present compound per 1 m3 in case of application for space. When the pest control agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.1 to 1, 000 ppm. When the pest control agent of the present invention is a formulation of oil solutions, aerosols, smoking agents and poison baits, they are usually applied as such.
[ 0297]
When the pesticidal composition of the present invention is used for controlling external parasites of livestock such as a cow, a horse, a pig, a sheep, a goat and a chicken, or small animals such as a dog, a cat, a rat and a mouse, it can be applied to said animals by a known method in the veterinary field. Specifically, when systemic control is intended, the pesticidal composition of the present invention is administered, for example, as a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.). When non-systemic control is intended, a method of using the pesticidal composition of the present invention includes spraying, pour-on treatment or a spot-on treatment with the pesticidal composition in the form of an oil solution or an aqueous liquid, washing an animal with the pesticidal composition in the form of a shampoo formulation, and attachment of a collar or a ear tag made of the pesticidal composition in the form of a resin formulation to an animal. When administered to an animal, the amount of the compound of the present invention is usually in the range of 0.1 to 1, 000 mg per 1 kg body weight of the animal.
[ 0298] The pest control agent of the present invention could be used in farmlands on which "crdps" shown below are cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, and tobacco;
Vegetables: Solanaceae vegetables (e.g., eggplant, tomato, green pepper, hot pepper, and potato), Cucurbitaceae vegetables (e.g., cucumber, pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (e.g., Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (e.g., burdock, garland chrysanthemum, artichoke, and lettuce), Liliaceae vegetables (e.g., Welsh onion, onion, garlic, and asparagus), Umbelliferae vegetables (e.g., carrot, parsley, celery, and parsnip), Chenopodiaceae vegetables (e.g., spinach, and Swiss chard), Labiatae vegetables (e.g., Japanese basil, mint, and basil), strawberry, sweat potato, yam, and aroid;
Fruit trees: pomaceous fruits (e.g.-, apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy -fruits (e.g., peach, plum, nectarine, Japanese plum, cherry, apricot, and prune), citrus plants (e.g., Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts (e.g., " chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut), berry fruits (e.g., blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and oil palm;
Trees other fruit trees: tea, mulberry, flowering trees (e.g., azalea, japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tulip poplar, crepe myetle, and orange osmanthus), street trees (e.g., ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, and horse-chestnut), sweet viburnum, Podocarpus macrophyllus , Japanese cedar, Japanese cypress, croton, spindle tree, and Chainese howthorn.
Lawn: zoysia (e.g., Japanese lawn grass . and mascarene grass), Bermuda grass (e.g., Cynodon dactylon), bent grass (e.g., creeping bent grass, Agrostis stolonifera, and Agrostis tenuis), bluegrass (e.g., Kentucky bluegrass and rough bluegrass), fescue (e.g., tall fescue,, chewing fescue, and creeping fescue), ryegrass (e.g., darnel and perennial ryegrass), cocksfoot, and timothy grass;
Others: flowers (e.g., rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners, gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, cymbidium, and begonia) , biofuel plants (e.g., Jatropha, curcas, safflower, Camelina alyssum, switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf, cassava, willow, and algae), and foliage plant.
[ 0299]
The "crops" include genetically modified crops.
[ 0300]
The pest control agent of the present invention can be used as a mixture with or together with other insecticides, acaricides, nematocides, fungicides, plant growth regulators, herbicides, and synergists. Examples of active ingredients of the insecticide, the acaricide, the nematocide, the fungicide, the herbicide, and the synergist are shown below.
[ 0301]
Examples of active ingredients of the insecticides include :
(1) organic phosphorus compounds:
acephate, aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos , chlorfenvinphos , chlorpyrifos , chlorpyrifos-methyl , cyanophos: CYAP, diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion : ECP, dichlorvos: DDVP, dimethoate, dimethylvinphos , disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion : MEP, fosthiazate, formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion : D TP, monocrotophos , naled: BRP, oxYdeprofos: ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos , temephos, tetrachlorvinphos , terbufos, thiometon, trichlorphon : DEP, vamidothion, phorate, and cadusafos.
(2) carbamate compounds:
alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: -MIPC, metolcarb, methomy1, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, and aldicarb.
[ 0302]
(3) synthetic pyrethroid compounds:
acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, , deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma- cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, profluthrin, dimefluthrin, 2 , 3 , 5 , 6-tetra fluoro-4- (methoxymethyl ) benzyl (EZ) - (IRS, 3RS; IRS, 3SR) -2,2- dimethyl-3-prop-l-enyl.cyclopropane carboxylate, 2,3,5,6- tetrafluoro-4-methylbenzyl (EZ) - (IRS, 3RS; IRS, 3SR) -2,2- dimethyl-3-prop-l-enylcyclopropane carboxylate, and
2, 3, 5, 6-tetrafluoro-4- (methoxymethyl) benzyl (IRS, 3RS; IRS, 3SR) -2 , 2-dimethyl-3- (2- methyl-l-propenyl ) cyclopropane carboxylate, 2,3,5,6- tetrafluoro-4- (methoxymethyl ) benzyl (EZ) - (IRS, 3RS; IRS, 3SR) - 2, 2-dimethyl-3- (2-cyano-l-propenyl) cyclopropane carboxylate.
(4) nereistoxin compounds:
cartap, bensultap, thiocyclam, monosultap, and bisultap.
[ 0303]
(5) neonicotinoid compounds:
imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, and clothianidin .
(6) benzoylurea compounds:
chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron. (7) phenylpyrazole compounds:
acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole .
(8) Bt toxin insecticides:
live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;
(9) hydrazine compounds:
chromafenozide, halofenozide, methoxyfenozide, and tebufenozide .
(10) organic chlorine compounds:
aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor .
[ 0304]
(11) other insecticides:
machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr , cyantraniliprole, cyromazine, D-D ( 1, 3-Dichloropropene ) , emamectin-benzoate, fenazaquin, flupyrazofos , hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metarn-ammonium, metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, Sulfur, metaflumizone, spirotetramat , pyrifluquinazone , spinetoram, chlorantranilxprole, tralopyril, cyantraniliprole, a compound represented by the following formula (K) :
Figure imgf000331_0001
wherein
R100 represents chlorine, bromine or a trifluoromethyl group, R200 represents chlorine, bromine or a methy group,
R300 represents chlorine, bromine or a cyano group, and
A compound represented by the following formula (L) :
Figure imgf000331_0002
wherein
R iooo represents chlorine, bromine or iodine.
[ 0305]
Examples of active ingredients of the acaricides include acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate, . chinomethionat , chlorobenzilate , CPCBS (chlorfenson) , clofentezine, cyflumetofen, dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite: BPPS, polynactins, pyridaben, Pyrimidifen, - tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet, and cyenopyrafen.
[ 0306]
Examples of active ingredients of the nematicides include DCIP, fosthiazate, levamisol, methyisothiocyanate, morantel tartarate, and imicyafos .
[ 0307]
Examples of active ingredients of the fungicides include azole fungicidal compounds such as propiconazole, prothioconazole , triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole , epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil , fenbuconazole, hexaconazole, fluquinconazole , triticonazole , bitertanol, imazalil, and flutriafol;
cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin;
benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl;
procymidone; cyprodinil; pyrimethanil ; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil ; captan; mepanipyrim; fenpiclonil ; fludioxonil ; dichlofluanid; folpet; kresoxim-methyl ; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide;. ethaboxam; amisulbrom; . iprovalicarb; benthiavalicarb; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil and tiadinil .
[ 0308]
Examples 'of active ingredients of the herbicides and the phytohormone agents include:
(1) phenoxyfatty acid herbicidal compounds such as 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide.
(2) benzoic acid herbicidal compounds such as 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
(3) urea herbicidal compounds such as diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron .
(4) triazine herbicidal compounds such as atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, triaziflam, and indaziflam.
(5) bipyridxnium. herbicidal compounds such as paraquat, and diquat .
[ 0309]
(6) hydroxybenzonitrile herbicidal compounds such as bromoxynil, and ioxynil.
(7) dinitroaniline herbicidal compounds such as pendimethalin, prodiamine, and trifluraliri .
(8) organic phosphorus herbicidal compounds such as amiprofos-methyl , butamifos, bensulide, piperophos, anilofos, glyphosate, ' glufosinate, glufosinate-P, and bialaphos.
(9) carbamate herbicidal compounds such as di-allate, tri- allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam.
(10) acid amide herbicidal compounds such as propanil, propyzamide, bromobutide) and etobenzanid.
[ 0310]
(11) chloroacetanilide herbicidal compounds such as acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and. pethoxamid.
(12) . diphenylether herbicidal compounds such as acifluorfen-sodium, bifenox, oxyfluorfen, lactofen) , fomesafen, chlomethoxynil , and aclonifen.
(13) cyclic imide herbicidal compounds such as oxadiazon, cinidon-ethyl , carfentrazone-ethyl , surfentrazone, flumiclorac-pentyl , flumioxazin, pyraflufen-ethyl , oxadiargyl, pentoxazone, fluthiacet-methyl , butafenacil , benzfendizone, bencarbazone, and saflufenacil .
(14) pyrazole herbicidal compounds such as benzofenap, pyrazo.late, pyrazoxyfen, topramezone, and pyrasulfotole .
(15) triketone herbicidal compounds such as isoxaflutole , benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione .
(16) aryloxyphenoxypropionic acid herbicidal compounds such as clodinafop-propargyl , cyhalofop-butyl , diclofop-methyl , fenoxaprop-ethyl , fluazifop-butyl , haloxyfop-methyl , and quizalofop-ethyl , metamifop.
(17) trioneoxime herbicidal compounds such as alloxydim- sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.
[ 0311]
(18) sulfonylurea herbicidal compounds such as chlorsulfuron, sulfometuron-methyl , metsulfuron-methyl , chlorimuron-ethyl , tribenuron-methyl , triasulfuron, bensulfuron-methyl , thifensulfuron-methyl , pyrazosulfuron- ethyl, primisulfuron-methyl , nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl , triflusulfuron-methyl , flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl , trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron .
(19) imidazolinone herbicidal compounds such as imazamethabenz-methyl , imazamethapyr , imazamox, imazapyr, imazaquin, and imazethapyr.
(20) sulfonamide herbicidal compounds such as flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl , penoxsulam, and pyroxsulam.
(21) pyrimidinyloxybenzoic acid herbicidal compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, and pyrimisulfan .
(22) other herbicidal compounds such as bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone , pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl , aminocyclopyrachlor, ipfencarbazone, and methiozolin. [ 0312] .
Examples of active ingredients of the synergists include, piperonyl butoxide, sesamex, sulfoxide, N-(2- ethylhexyl) -8, 9, 10-trinorborn-5-ene-2 , 3-dicarboximide (MGK 264 ) , N-declyimidazole, ARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH3I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ET .
Examples
[ 0313]
Hereinafter, the present invention is described in more detail by referrence to . Production Examples, Referece Production Examples, Formulation Examples and Test Examples which the present invention is not limited to.
Firstly, Production Examples of the present compound are descrbed below.
[ 0314]
Production Example 1(1)
A mixture of N2-methyl-5-trifluoromethylpyridin-2 , 3- diamine (0.76 g) , 3-fluoropyridin-2-carboaldehyde (0.50 g) , sodium hydrogen sulfite (0.50 g) and DMF (3 ml) was stirred at 120°C for 8 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- fluoropyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (0.43 g) , which is hereinafter referred to as "intermediate compound (M6-2)".
Intermediate compound (M6-2)
Figure imgf000338_0001
1H-NMR (CDC13) δ: 8.75 (lH,d), 8.66-8.63 (lH,m), 8.40 (lH,d), 7.73-7.67 (lH,m), 7.56-7.51 (lH,m), 4.16 (3H,s).
[ 0315]
Production Example 1(2)
To a mixture of the intermediate compound (M6-2) (1.23 g) and DMF (3.5 ml) was added sodium ethanethiolate (0.48 g) while ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanyl pyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H-imidazo[ 4,5- b] pyridine (1.39 g) , which is hereinafter .referred
"the present compound 1".
The present compound 1.
Figure imgf000339_0001
1H-NMR (CDC13) δ : 8.73 (lH,d), 8.53 (lH,dd), 8.39 (lH,d), 7.80 (lH,dd), 7.40 (lH,dd), 4.04 (3H,s), 2.97 (2H,q), 1.35 (3H,t).
[ 0316]
Production Examples 2 and 3
To a mixture of 2- ( 3-ethylsulfanyl pyridin-2-yl ) -3- methyl-6-trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.62 g) and chloroform (10 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.79 g) while ice-cooling, and then the mixture was stirred at room temperature for 5 hours. To the reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfinyl pyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (87 mg) , which is hereinafter referred to as "the present compound 2", and 2- ( 3-ethylsulfonylpyridin-2-yl ) -3-methyl-6-trifluoromethyl- 3H-imidazo[ , 5-b] pyridine (0.49 g) , which is hereinafter referred to as "the present compound 3".
The present compound 2
Figure imgf000340_0001
1H-N R (CDC13) δ: 8.85 (lH,dd), 8.77 (lH,s), 8.67 (lH,dd), 8.34 (lH,s), 7.69 (lH,dd), 4.36 (3H,s), 3.72-3.62 (lH,m), 3.14-3.04 (lH,m), 1.47 (3H,t).
The present compound 3
Figure imgf000340_0002
1H-NMR (CDCI3) δ: 9.01 (lH,dd), 8.76 (lH,s), 8.55 (lH,dd), 8.31 (lH,s), 7.74 (lH,dd), 3.88 (3H,s), 3.83 (2H,q), 1.37 (3H, t) .
[ 0317]
Production Example 4(1)
A mixture of N2-methyl-5-trifluoromethylpyridin-2 , 3- diamine (0.70 g) , 3-chloro-5-trifluoromethylpyridin-2- carboxylic acid (0.53 g) , WSC (0.82 g) , HOBt (42 mg) and pyridine (4.5 ml) was stirred at 60°C for 4 hours. To the cooled reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an intermediate compound (M20-3).
Figure imgf000341_0001
A mixture of the resulting intermediate compound (M3- 4) (total amount), p-toluenesulfonic acid monohydrate (1.04 g) and N-methylpyrrolidinone (4 ml) was stirred while heating to 150°C for 2.5 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The. resulting residue was subjected to silica gel column chromatography to give 2-{3- chloro-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.71 g) , which is hereinafter referred to as "intermediate compound (M6- 3 ) " .
Intermediate compound (M6-3)
Figure imgf000342_0001
1H-NMR (CDCI3) δ: 8.96 (lH,d), 8.79 (lH,d), 8.42 (lH,d), 8.22 (lH,d) , 4.02 (3H,s) .
[ 0318]
Production Example 4(2)
To a mixture of 2- ( 3-chloro-5-trifluoromethylpyridin- 2-yl ) -3-methyl-6-trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.71 g) and DMF ( ml) was added sodium ethanethiolate (0.24 g) while ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. . The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (0.76 g) , which is hereinafter referred to as "the present compound 4".
The present compound 4
Figure imgf000342_0002
1H-NMR (CDCI3) δ: 8.77 (lH,d), 8.75 (lH,d), 8.43 (lH,d), 7.93 (lH,d), 4.11 (3H,s), 3.02 (2H,q), 1.40 (3H,t).
[ 0319]
Production Example 5
To a mixture of 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (0.61 g) and chloroform (10 ml) was added m-chloroperbenzoic. acid (purity: not less than 65%)
(0.66 g) while ice-cooling, and the mixture was stirred at room temperature for 10 hours. To the reaction mixture were added aqueous 10% sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2-
( 3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ , 5-b] pyridine (0.62 g) , which is hereinafter referred to as "the present compound 5".
The present compound 5
Figure imgf000343_0001
""Ή-Ν ΡΧ (CDC13) δ: 9.25 (lH,d), 8.80 (lH,d), 8.79 (lH,d), 8.34 (lH,d), 3.96 (2H,q), 3.94 (3H,s), 1.42 (3H,t).
[ 0320] Production Example 6
A mixture of 2- (3-ethylsulfanyl-pyridin-2-yl ) -6-iodo- 3-methyl-3H-imidazo[ 4 , 5-b] pyridine (835 mg) , sodium pentafluoropropionate (2.0 g) , copper iodide (2.0 g) , NMP (10 ml) and xylene (50 ml) was stirred while heating to 150°C for 8 hours. After allowing to cool to room temperature, to the reaction mixture were added 40% aqueous ammonia solution and saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- ethylsulfanyl-pyridin-2-yl ) -3-methyl-6-pentafluoroethyl-3H- imidazo[ 4 , 5-b] pyridine (303 mg) , which is hereinafter referred to as "the present compound 6".
The present compound 6
Figure imgf000344_0001
H-NMR (CDC13) δ : 8.69 (lH,d), 8.52 (lH,dd), 8.40 (lH,d), 7.80 (lH,dd), 7.39 (lH,dd), 4.06 (3H,s), 2.97 (2H,q), 1.34
(3H, t) .
[ 0321]
Production Examples' 7 and 8 To a mixture of 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -3- methyl-6-pentafluoroethyl-3H-imidazo[ 4 , 5-b] pyridine (254 mg). and chloroform (10 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (266 mg) while ice-cooling The mixture was heated to room temperature and then stirred for 0.5 hours. To the mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-ethane sulfinyl-pyridin-2-yl ) - 3-methyl-6-pentafluoroethyl-3H-imidazo[ 4 , 5-b] pyridine (8 mg) , which is hereinafter referred to as "the present compound 7"), and 2- ( 3-ethanesulfonyl-pyridin-2-yl ) -3- methyl- 6-pentafluoroethyl-3H-imidazo[ 4 , 5-b] pyridine (235 mg) , which is hereinafter referred to as "the present compound 8".
The present compound 7
Figure imgf000345_0001
■""H-NMR (CDC13) δ: 8.85 (lH,dd), 8.72 (lH,d), 8.68 (lH,dd), 8.31 (lH,d), 7.69 (lH,dd), 4.36 (3H,s), 3.72-3.61 . ( 1H, m) , 3.17-3.06 (lH,m), 1.47 (3H,t).
The present compound 8
Figure imgf000346_0001
!H-NMR (CDCI3) δ: 9.00 (lH,dd), 8.72 (lH,d), 8.55 (lH,dd), 8.30 (lH,d), 7.73 (lH,dd), 3.89 (3H,s), 3.8 (2H,q), 1.37 (3H,t).
[ 0322]
Production Example 9(1)
To a mixture of 5-iodo-N2-methyl-pyridin-2 , 3-diamine (1.9 g) and pyridine (6 ml) were added WSC (1.28 g) , HOBt (86 mg) and 3-chloro-pyridin-2-carboxylic acid (1.3 g) , and the mixture was stirred at room temperature for 9 hours. To this reaction mixture was added water, and the mixture was filtered to collect the precipitated powder. The collected powder was washed with chloroform to give 3- chloro-pyridin-2-carboxylic acid ( 5-iodo-2-methylamino- pyridin-3-yl ) -amide (3.6 g) , which , is hereinafter referred to as "intermediate compound (M20-7)".
Intermediate compound (M20-7)
Figure imgf000347_0001
XH-NMR ( DMSO-d6) δ: 9.95 (lH,s), 8.65 (lH,d), 8.15-8.10 (2H,m), 8.00 (lH,d), 7.65 (lH,dd), 6.30 (lH,d), 2.81 (3H,d) [ 0323]
Production Example 9(2)
A mixture of the intermediate compound (M20-7) (3.4 g) , p-toluenesulfonic acid monohydrate (5.8 g) , DMF (30 ml) and toluene (120 ml) was stirred while heating to 130°C for 12 hours. After allowing to cool to room temperature, to the mixture was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3-chloro-pyridin-2-yl) -6-iodo-3-methyl-3H- imidazo[ 4 , 5-b] pyridine (2.0 g) , which is hereinafter referred to as "intermediate compound (M6-7)".
Intermediate compound (M6-7)
Figure imgf000347_0002
1H-NMR (CDC13) δ: 8.70 (lH,d), 8.66-8.63 (lH,m), 8.47-8.44 (lH,m), 7.95 (lH,d), 7.45 (lH,dd), 3.90 (3H,s).
[ 0324]
Production Example 9(3)
A mixture of the intermediate compound (M6-7) (2.0 g) , sodium ethanethiolate (888 mg) and DMF (45 ml) was stirred while heating at 50°C for 12 hours. After allowing to cool to room temperature, to the mixture was poured saturated aqueous sodium. hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -6- iodo-3-methyl-3H-imidazo[ 4 , 5-b] pyridine (1.0 g) , which is hereinafter referred to as "the present compound 9".
The present compound 9
Figure imgf000348_0001
■""H-NMR (CDC13) δ: 8.61 (lH,d), 8.51 (lH,dd), 8.45 (lH,d), 7.76 (lH,dd), 7.37 (lH,dd), 3.96 (3H,s), 2.94 (2H,q), 1.33 (3H,t).
[ 0325]
Production Example 10(1)
A mixture of 3-amino-5-trifluoromethylpyridin-2-thiol (0.45 g) , 3-chloro-5-trifluoromethylpyridin-2-carboxylic acid (0.55 g) , WSC (0.67 g) , HOBt (31 mg) and pyridine (4.5 ml) was stirred at 60°C for 4 hours. To the cooled reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give intermediate compound (M20-9) .
Intermediate compound (M20-9)
Figure imgf000349_0001
A mixture of the resulting intermediate compound (M20- 9) (total amount), p-toluenesulfonic acid monohydrate (1.04 g) and N-methylpyrrolidinone (3.5 ml) was stirred while heating to 150°C for 2 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-chloro-5- trifluoromethylpyridin-2-yl ) -6-
(trifluoromethyl) thiazolo[ 5, 4-b] pyridine (0.29 g) , which is hereinafter referred to as "intermediate compound. (M6-9)". Intermediate compound (M6-9)
Figure imgf000350_0001
■""H-NMR (CDCI3) δ: 8.94 (lH,d), 8.90 (lH,d), 8.69 (lH,d), 8.19 (lH,d) .
[ 0326]
Production Example 10(2)
2- ( 3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl ) -6- ( trifluoromethyl ) thiazolo[ 5 , 4 -b] pyridine (hereinafter referred to as "the present compound 10") was synthesized in the same manner as in Production Example 4(2) except for using the intermediate compound ( 6-9) instead of 2- (3- chloro-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine .
Figure imgf000350_0002
1H-NMR (CDCI3) δ: 8.91 (lH,d), 8.70-8.67 (2H,m), 7.91 (lH,s), 3.09 (2H,q), 1.51 (3H,t).
[ 0327]
Production Example 11
2- ( 3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl ) -6- (trifluoromethyl ) thiazolot 5, 4-b] pyridine (hereinafter referred to as "the present compound 11") was synthesized in the same manner as in Production Example 5 except for using 2- ( 3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl ) -6- ( trifluoromethyl ) thiazolo[ 5 , 4-b] pyridine instead of 2- (3- ethylsulfanyl-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine .
Figure imgf000351_0001
^- MR (CDC13) δ : 9.19 (lH,d), 8.98 (lH,d), 8.89 (lH,d), 8.61 (lH,d), 4.17 (2H,q), 1.49 (3H,t).
[ 0328]
Production Example 12(1)
A mixture of 3-amino-5-trifluoromethylpyridin-2-thiol (0.45 g) , 3-chloropyridin-2-carboxylic acid (0.39 g) , WSC (0.67 g) , HOBt (31 mg) and pyridine (4 ml) was stirred at room temperature for 12 hours. To the reaction mixture was added water, and the mixture was filtered to collect a solid. The resulting solid was washed with water, followed by n-hexane, and dried to give 3-chloropyridin-2-carboxylic acid ( 2-mercapto-5-trifluoromethylpyridin-3-yl ) -amide (0.45 g) , which is hereinafter referred to as "intermediate compound (M20-11)".
Intermediate compound (M20-11)
Figure imgf000352_0001
[ 0329]
Production Example 12(2)
A mixture of the intermediate compound (M20-11) (0.45 g) , p-toluenesulfonic acid monohydrate (0.70 g) and NMP (4 ml) was stirred at 150°C for 2 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- (3- chloropyridin-2-yl ) -6- ( trifluoromethyl )thiazolo[ 5,4- b] pyridine (0.47 g) , which is hereinafter referred to as "intermediate compound (M6-11)".
Intermediate compound (M6-11)
Figure imgf000352_0002
[ 0330]
Production Example 12(3)
2- (3-ethylsulfanyl-2-yl) -6- (trifluoromethyl) thiazolo[ 5 , 4 -b] pyridine (hereinafter referred to as "the present compound 41") was synthesized in the same manner as in Production Example 1 (2) except for using the intermediate compound (M6-11) instead of 2- (3- fluoropyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine .
Figure imgf000353_0001
1H-NMR (CDC13) δ: 8.87 (lH,d), 8.64 (lH,d), 8.48 (lH,dd), 7.76 (lH,dd), 7.37 (lH,dd), 3.06 (2H,q), 1.49 (3H,t) .
[ 0331]
Production Example 12(4)
To a mixture of 2- ( 3-ethylsulfanyl-2-yl ) -6- ( trifluoromethyl ) thiazolo[ 5 , 4-b] pyridine (0.36 g) and chloroform (5 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.56 g) , and the mixture was stirred at room temperature for 12 hours. To the reaction mixture were poured aqueous 10% sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution, and, the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2- ( 3-ethylsulfonyl-2-yl ) -6- ( trifluoromethyl ) thiazolo[ 5,4- b] pyridine (0.27 g) , which is hereinafter referred to as "the present compound 12", and 2- ( 3-ethylsulfonyl-2-yl ) -6- (trifluoromethyl) thiazolof 5, 4-b] pyridine 4-oxide (91 mg) , which is hereinafter referred to as "the present compound 22".
The present compound 12
Figure imgf000354_0001
1H-NMR (CDC13) δ: 8.98-8.93 (2H,m) , 8.66 (lH,dd), 8.57 (lH,d), 7.69 (lH,dd), 4.13 (2H,q), 1.45 (3H,t).
The present compound 22
Figure imgf000354_0002
^H-NMR (CDCI3) δ: 8.96 (lH,dd), 8.68 (lH,dd), 8.62 (lH,s), 8.20 (lH,s), 7.74 (lH,dd), 4.06. (2H,q), 1.44 (3H,t).
[ 0332]
Production Example 13(1)
A mixture of 2- ( 3-ethylsulfanyl-pyridin-2-yl )- 6-iodo- 3-methyl-3H-imidazo[ 4 , 5-b] pyridine (1.1 g) , copper iodide (160 mg) , sodium sulfide 9-hydrate (2.7 g) and D F (10 ml) was stirred at 110°C for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give a compound represented by the formula
Figure imgf000355_0001
(710 mg) , which is hereinafter referred to as "intermediate compound (P9'-l)".
Intermediate compound (P9'-l) ·
■""H-NMR ( DMSO-De) δ: . 8.56-8.55 (2H,m), 8.53-8.50 (2H,m), 8.38-8.36 (2H,m), 8.04 (2H,d)., 7.61-7.56 (2H,m) , 3.87 (6H,brs), 3.00 (4H,q), 1.23-1.16. (6H,m).
[ 0333] .
Production Example 13(2)
A mixture of the intermediate compound (P9'-l) (710 mg) and DMF (12 ml) was cooled to -60°C, and thereto was added trifluoroiodomethane (10 g) . To this mixture was added dropwise tetrakis (dimethylamino) ethylene (1.2 ml) at -40°C. The mixture was warmed to -10°C, and stirred at - 10°C for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- ethylsulfanyl-pyridin-2-yl ) -3-methyl-6- trifluoromethylsulfanyl-3H-imidazo[ 4 , 5-b] pyridine (530 mg) , which is hereinafter referred to as "the present compound 13". .
The present compound 13
Figure imgf000356_0001
1H-N R (CDC13) δ: 8.67 (lH,d), 8.52 (lH,dd), 8.46 (lH,d), 7.79 (lH,dd), 7.39 (lH,dd), 4.03 (3H,s), 2.97 (2H,q),. 1.36 (3H,t).
[ 0334]
Production Examples 1 and 15
A mixture of 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -3- methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4,5-b] pyridine (200 mg) , m-chloroperbenzoic acid (purity: not less than 65%) (230 mg) and chloroform (10 ml) was stirred while ice- cooling for 5 hours. To the reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfinyl-pyridin-2- yl ) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4,5- b] pyridine (89 mg) , which is hereinafter referred to as "the present compound 14", and 2- (3-ethylsulfonyl-pyridin- 2-yl ) -3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4 , 5- b] pyridine (130 mg) , which is hereinafter referred to as "the present compound 15".
The present compound 14
Figure imgf000357_0001
1H-NMR (CDCI3) δ: 8.87-8.83 (lH,m), 8.73-8.64 (2H,m), 8.41 (lH,d), 7.72-7.66 (lH,m), 4.34 (3H,s), 3.72-3.62 (lH,m), 3.17-3.05 (lH,m), 1.47 (3H,t).
The present compound 15
Figure imgf000357_0002
^-NMR (CDCI3) δ: 9.01-8.98 (lH,m), 8.71 (lH,d), 8.55-8.52 (lH,m), 8.39 (lH,d), 7.72 (lH,dd), 3.90-3.81 (5H,m), 1.36 (3H,t).
[ 0335]
Production Example 16
To a mixture of 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -3- methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4,5-b] pyridine (270 mg) , sodium tungstate dihydrate (110 mg) , and acetonitrile (5 ml) was added 30% hydrogen peroxide solution (2 ml) at 40°C. The mixture was heated to 80°C and then stirred for 24 hours. To the mixture was added saturated aqueous sodium thiosulfate solution, and the miture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfonyl-pyridin-2- yl ) -3-methyl- 6-trifluoromethylsulfonyl-3H-imidazo[ 4,5- b] pyridine (280 mg) , which is hereinafter referred to as "the present compound 16".
The present compound 16
Figure imgf000358_0001
"""H-NMR (CDC13) δ: 9.08 (lH,d), 9.04 (lH,dd), 8.71 (lH,d), 8.57 (lH,dd), 7.79 (lH,dd), 3.93 (3H,s), 3.82 (2H,q), 1.38 (3H, t) .
[ 0336]
Production Example 17(1)
A mixture of N2-methyl-5-pentafluoroethyl-pyridin-2 , 3- diamine (590 mg) , 3-chloro-5-trifluoromethyl-pyridin-2- carboxylic acid (560 mg) , WSC (520 mg) , HOBt (35 mg) , and pyridine (5 ml) was stirred at room temperature for 5 hours To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give intermediate compound (M20-17) .
Figure imgf000359_0001
The resulting intermediate compound (M20-17) was dissolved in a mixed solvent of DMF (7.5 ml) and toluene (30 ml), thereto was added p-toluenesulfonic acid monohydrate (1.5 g) , and the mixture was stirred at 160°C for 6 hours. The reaction mixture was allowed to cool to room temperature, thereto was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with t-butylmethyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- ( 3-chloro-5-trifluoromethyl- pyridin-2-yl ) -3-methyl-6-pentafluoroethyl-3H-imidazo[ 4, 5- b] pyridine (540 mg) , which is hereinafter referred to as "intermediate compound (M6-17)".
Intermediate compound (M6-17)
Figure imgf000360_0001
1H-NMR (CDCI3) δ: 8.96 (lH,d), 8.74 . (lH,d), 8.40 (lH,d), 8.23 (lH,d) , 4.03 (3H,s) .
[ 0337]
Production Example 17(2)
2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -3- methyl-6-pentafluoroethyl-3H-imidazo[ 4,5-b] pyridine
(hereinafter referred to as "the present compound 17") was synthesized; in the same manner as in Production Example 1(2) except for using the intermediate compound (M6-17) instead of 2- ( 3-fluoropyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4,5-b] pyridine.
The present compound 17
Figure imgf000360_0002
'H-NMR (CDCI3) δ: 8.75 (lH,d), 8.71 (lH,d), 8.42 (lH,d), 7.93 (lH,d), 4.12 (3H,s), 3.03 (2H,q), 1.41 (3H,t).
[ 0338]
Production Examples 18 and 19
2- ( 3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl ) -3- methyl-6-pentafluoroethyl-3H-imidazo[ 4,5-b] pyridine (hereinafter referred to as "the present compound 18") and 2- ( 3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl ) -3- methyl-6-pentafluoroethyl-3H-imidazo[ 4,5-b] pyridine
(hereinafter referred to as "the present compound 19") were synthesized in the same manner as in Production Examples 2 and 3 except for using 2- ( 3-ethylsulfanyl-5- trifluoromethyl-pyridin-2-yl ) -3-methyl-6-pentafluoroethyl- 3H-imidazo[ 4 , 5-b] pyridine instead of 2- (3-ethylsulfanyl pyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H-imidazo[ 4,5- b] pyridine .
The present compound118
Figure imgf000361_0001
1H-N R (CDCI3) δ: 9.10 (lH,d), 8.94 (lH,d), 8.76 (lH,d), 8.36 (lH,d), 4.41 (3H,s), 3.76-3.66 (lH,m),. 3.18-3.07 (lH,m) , 1. 9 (3H, t) .
The present compound 19
Figure imgf000361_0002
1H-NMR (CDCI3) δ: 9.27 (lH,d), 8.80 (lH,d), 8.76 (lH,s), 8.34 (lH,s), 4.01-3.94 (5H,m), 1.41 (3H,t). [ 0339]
Production Example 20
To a mixture of 2- ( 3-ethylsulfonyl-pyridin-2-yl ) -3- methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4,5-b] pyridine (500 mg) and chloroform (10 ml) was added m- chloroperbenzoic acid (purity: not less than 65%) (429 mg) while ice-cooling, and the mixture was stirred at room temperature for 1 hour and at 50 °C for 2 hours. To the reaction mixture were poured agueous sodium thiosulfate solution and aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfonyl-pyridin-2- yl ) -3-methyl-6-trifluoromethylsulfinyl-3H-imidazo[ 4,5- b] pyridine (353 mg) , which is hereinafter referred to as "the present compound 20".
The present compound 20
Figure imgf000362_0001
1H-NMR (CDC13) δ : 9.02 (lH,dd), 8.77 (lH,d), 8.60-8.52 (2H,m) , .7.75 (lH,dd), 3.91 (3H,s), 3.83 (2H,q), 1.38 (3H,t) .
[ 0340] Production Example 21(1)
To a mixture of 4-iodo-2-nitro-phenyl amine (2.0 g) , 60% sodium hydride (oil) (330 mg) , and DMF (20 ml) was added dropwise iodomethane (470pL) while ice-cooling. The reaction mixture was heasted to room temperature, and then stirred for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give (4- iodo-2-nitro-phenyl ) -methyl-amine (2.0' g) .
Figure imgf000363_0001
[ 0341]
Production Example 21(2)
A mixture of an iron powder (1.7 g) , acetic acid (2.2 ml), ethanol (80 ml), and water (25 ml) was stirred at 70°C. To the reaction mixture was added dropwise a mixture of (4- iodo-2-nitro-phenyl ) -methyl-amine (2.0 g) and ethanol (20 ml) . After that, the mixturee was stirred at 70°C for 6 hours. Then, the reaction mixture was filtrated and thoroughly washed with THF. The resulting filtrate was concentrated under reduced pressure. To the resulting residue was poured saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4-iodo-N1-methyl-benzene-l, 2-diamine (1.6 g) .
Figure imgf000364_0001
[ 0342]
Production Example 21(3)
A mixture of 4-iodo-N1-methyl-benzene-l , 2-diamine (850 mg) , 3-chloro-pyridin-2-carboxylic acid (590 mg) , SC (790 mg) , HOBt (46 mg) , and pyridine (10 ml) was stirred at 100°C for 12 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- chloro-pyridin-2-yl ) -5-ipdo-l-methyl-lH-benzimidazole (930 mg) , which is hereinafter referred to as "intermediate compound (M6-21)".
Intermediate compound (M6-21)
Figure imgf000364_0002
[ 0343]
Production Example 21(4)
2- ( 3-ethylsulfanyl-pyridin-2-yl ). -5-iodo-l-methyl-lH- benzimidazole (hereinafter referred to as . "the present compound 21") was synthesized in the same manner as in Production Example 1(2) except for using the intermediate compound (M6-21) instead of 2- ( 3-fluoropyridin-2-yl ) -3- methyl-6-trifluoromethyl-3H-imidazo[ 4,5-b] pyridine.
The present compound 21
Figure imgf000365_0001
1H-NMR (CDC13) δ: 8.49 (lH,dd), 8.22 (lH,d), 7.75 (lH,d)r 7.62 (lH,dd), 7.35 (lH,dd), 7.21 (lH,d), 3.87 (3H,s), 2.92 (2H,q) , 1.32 (3H,t) .
[ 0344]
Production Example 22(1)
A mixture of 4-amino phenyl sulfur pentafluoride (5.2 g) , acetic acid anhydride (2.7 ml), triethylamine (6.6 ml) and chloroform (20 ml) was stirred at room temperature for 3 hours. To the reaction mixture was poured water, and the mixture was extracted with chloroform. The resulting residue was subjected to recrystallization with hexane and ethyl acetate to give 4-acetoamide phenyl sulfur pentafluoride (5.4 g) .
Figure imgf000366_0001
[ 0345]
Production Example 22(2)
To a mixture of 4-acetoamide phenyl sulfur pentafluoride (5.4 g) and sulfuric acid (15 ml) was added dropwise fuming nitric acid (905 ml) while ice-cooling. After that, the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured onto ice, and the precipitated crystal was collected by filtration. The crystal was washed with water and dried to give 4-amino-3- nitro phenyl sulfur pentafluoride (5.2 g) .
Figure imgf000366_0002
[ 0346]
Production Example 22(3)
To. a mixture of -amino-3-nitro-phenyl sulfur pentafluoride (2.0 g) , 60% sodium hydride (oil) (310 mg) and DMF (15 ml) was added dropwise iodomethane (447 pL) while ice-cooling. After that, the mixture was stirred at room temperature for 3 hours. To the reaction mixture was poured water, and the precipitated solid was collected by filtration. The solid was washed with water and dried to give methyl- (2-nitro-4-pentafluorosulfanyl-phenyl ) -amine (2.0 g) .
Figure imgf000367_0001
^-NMR (CDC13) δ: 8.60 (lH,d), 8.28 (lH,brs), 7.78 (lH,dd), 6.89 (lH,d) , 3.10 (3H,d) .
[ 0347]
Production Example 22(4)
N1-methyl-4-pentafluorosulfanyl-benzene-1 , 2-diamine was synthesized in the same manner as in Production Example 21(2) except for using methyl- (2-nitro-4- pentafluorosulfanyl-phenyl ) -amine instead of (4-iodo-2- nitro-phenyl ) -methyl-amine .
Figure imgf000367_0002
[ 0348]'
Production Example 22(5)
3-chloro-pyridin-2-carboxylic acid (2-methylamino-5- pentafluorosulfanyl-phenyl ) -amide (hereinafter referred to as "intermediate compound (M20-23)") was synthesized in the same manner as in Production Example 9(1) except for using N1-methyl-4-pentafluorosulfanyl-benzene-1 , 2-diamine instead of 5-iodo-N2-methyl-pyridin-2, 3-diamine .
Intermediate compound (M20-23)
Figure imgf000368_0001
1H-NMR (CDCI3) δ : 9.57 (lH,s), 8.55 (lH,dd), 7.91 (lH,dd), 7.81 (lH,d), 7.59 ( 1H, dd) , 7.50-7.45 (lH,m), 6.71 (lH,d), 4.52 (lH,d) , 2.93 (3H,d) .
[ 0349]
Production Example 22(6)
To a mixture of the intermediate compound (M20-23) (405 mg) and DMF (10 ml) was added sodium ethanethiolate (193 mg) while ice-cooling, and then the mixture was stirred at room temperature for 8 hours and 60 °C for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanyl-5- trifluoromethyl-pyridin-2-yl ) -1-methyl-5- pentafluorosulfanyl-lH-benzimidazole (411 mg) , which is hereinafter referred to as "the present compound 23".
The present compound 23
Figure imgf000369_0001
1H-NMR (CDCI3) δ: 8.50, (lH,dd), 8.33 (lH,d), 7.79-7.74 (2H,m), 7.46-7.43 (lH,m), 7.37 (lH,dd), 3.92 (3H,s), 2.94 (2H,q), 1.33 (3H,t).
[ 0350]
Production Example 23
2- ( 3-ethylsulfonyl-pyridin-2-yl ) -l-methyl-5- pentafluorosulfanyl-lH-benzimidazole (hereinafter referred to as "the present compound 24") was synthesized in the same manner as in Production Example 11 except for using 2- (3-ethylsulfanyl-pyridin-2-yl ) -1-methyl-5- pentafluorosulfanyl-lH-benzimidazole instead of 2-(3- ethylsulfanyl-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine .
The present compound 24
Figure imgf000369_0002
"""H-NMR (CDCI3) δ: 8.96 (lH,dd), 8.50 (lH,dd), 8.24 (lH,d), 7.79 (lH,dd), 7.68 (lH,dd), 7.48 (lH,d), 3.82 (2H,q), 3.75 (3H, s) , 1.34 (3H,t) . [ 0351]
Production Example 24(1)
3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid ( 5-iodo-2-methylamino-pyridin-3-yl ) -amide (hereinafter referred to as "intermediate compound (M20-35)") was synthesized in the same manner as in Production Example 9(1) except for using 3-chloro-5-trifluoromethyl-pyridin-2- carboxylic acid instead of 3-chloro-pyridin-2-carboxylic acid.
Figure imgf000370_0001
^H-NMR (CDC13) δ: 9.33 (lH.,s), 8.80 (lH,d), 8.28 (lH,d), 8.17 (lH,d), 8.00 (lH,d), 4.60 (lH,s), 3.01 (3H,d) .
[ 0352]
Production Example 24(2)
2- ( 3-chloro-5-trifluoromethyl-pyridin-2-yl ) -6-iodo-3- methyl-3H-imidazo[ 4 , 5-b] pyridine (hereinafter referred to as "intermediate compound (M6-35)") was synthesized in the same manner as in Production Example 9(2) except for using the intermediate compound (M20-35) instead of 3-chloro- pyridin-2-carboxylic acid ( 5-iodo-2-methylamino-pyridin-3- yl) -amide.
Intermediate compound (M6-35)
Figure imgf000371_0001
""■H-NMR (CDCI3) δ : 8.95 (lH,s), 8.68 (lH,s), 8.49 (lH,s), 8.20 (1H, s) , 3.95 (3H, s) . "
[ 0353]
Production Example 24(3)
2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -6- iodo-3-methyl-3H-imidazo[ 4 , 5-b] pyridine (hereinafter referred to as "the present compound 42") was synthesized in the same manner as in Production Example 1(2) except for using the intermediate compound (M6-35) . instead of 2- (3- fluoropyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4,5-b] pyridine.
The present compound 42
Figure imgf000371_0002
1H-NMR (CDCI3) δ : 8.73 (lH,s), 8.65 (lH,d), 8.49 (lH,d), 7.91 (lH,s), 4.04 (3H,s), 3.01 (2H,q), 1.39 (3H,t).
[ 0354]
Production Example 24(4)
A mixture of 2-( 3-ethylsulfanyl-5-trifluoromethyl- pyridin-2-yl ) -6-iodo-3-methyl-3H-imidazo[ 4 , 5-b] pyridine (900 mg) , thiobenzoic acid 3(20 L) , copper iodide (45 mg) , 1 , 10-phenanthroline (85 mg), diisopropylethylamine (940 μΐ,) , and toluene (25 ml) was stirred at 110°C for 8 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give thiobenzoic acid S-[ 2-(3- ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -3-methyl-3H- imidazo[ 4,5-b] pyridine] ester (990 mg) .
Figure imgf000372_0001
1H-NMR (CDC13) 6: 8.74 (lH,s), 8.54 (lH,d), 8.33 (lH,d), 8.07 (2H,dd), 7.92 (lH,s),. 7.63 (lH,t),7.51 (2H,t),4.10 (3H,s), 3.01 (2H,q), 1.39 (3H,t).
[ 0355]
Production Example 24(5)
A mixture of thiobenzoic acid S-[ 2- ( 3-ethylsulfanyl-5- trifluoromethyl-pyridin-2-yl ) -3-methyl-3H-imidazo[ 4,5- b] pyridine] ester (1.8 g) , potassium carbonate (1.1 g) , and methanol (20 ml) was stirred at room temperature for 4.5 hours. To the reaction mixture was poured saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution., dried over sodium sulfate, and concentrated under reduced pressure to give 2- ( 3-ethylsulfanyl-5-trifluoromethyl- pyridin-2-yl ) -3-methyl-3H-imidazo[ 4, 5-b] pyridin-6-thiol (1.2 g) , which is hereinafter referred to as "the present compound .43" .
The present compound 43
Figure imgf000373_0001
^H-NMR (CDC13) δ: 8.73 (lH,s),. 8.46 (lH,d), 8.19 (lH,d), 7.90 (lH,s), 4.04 (3H,s),. 3.01 (2H,q), 1.39 (3H,t).
[ 0356]
Production Example 24(6)
To a mixture of ' 2- ( 3-ethylsulfanyl-5-trifluoromethyl- pyridin-2-yl ) -3-methyl-3H-imidazo[ 4, 5-b] pyridin-6-thiol (1.2 g) , iodine (20 mg) , and DMF (30 ml) was stirred at room temperature under air atmosphere for 12 hours. The reaction mixture was concentrated, and then the residue was subjected to silica gel column chromatography to give a compound represented by the formula:
Figure imgf000374_0001
(800 mg) , which is hereinafter referred to as "intermediate compound (P9!-4)".
Intermediate compound (P9'-4)
"""H-NMR (CDC13) δ: 8.73 (2H,s), 8.52 (2H,d), 8.35. (2H,d), 7.91 (2H,d), 4.06(6H,s), 3.04-2.98 (4H,m) , 1.39(6H,t).
[ 0357]
Production Example 24(7)
2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -3- methyl-6-trifluoromethylsulfanyl-3H-imidazo[ 4 , 5-b] pyridine (hereinafter referred to as "the present compound 28") was synthesized in the same manner as in Production Example 13(2) except for using the intermediate compound (P9'-4) instead of the intermediate compound (P9'-l) .
The present compound 28
Figure imgf000374_0002
^"H-NMR (CDCI3) δ: 8.75 (lH,d), 8.71 (lH,d), 8.50 (lH,d), 7.93 (lH,d), 4.10 (3H,s), 3.03 (2H,q), 1.41 (3H,t).
t 0358] Production Example 24(8)
To a mixture of 2- ( 3-ethylsulfanyl-5-trifluoromethyl- pyridin-2-yl ) -3-methyl-6-trifluoromethylsulfanyl-3H- imidazo[ 4 , 5-b] pyridine (299 mg) and chloroform (30 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.34 g) while ice-cooling, and the mixture was stirred while ice-cooling for 5 hours. To the reaction mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- (3- ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl ) -3-methy1- 6- trifluoromethylsulfanyl-3H-imidazo[ 4 , 5-b] pyridine (0.24 g) , which is hereinafter referred to as "the present compound 44".
The present compound 44
Figure imgf000375_0001
"'"H-NMR (CDC13) δ: 9.24 (lH,d), 8.79 (lH,d), 8.74 (lH,d), 8.40 (lH,d), 3.97 (2H,q), 3.93 (3H,s), 1.42 (3H,t).
[ 0359] Production Example 24(9)
2- ( 3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl ) -3- methyl-6-trifluoromethylsulfonyl-3H-imidazo[ 4, 5-b] pyridine (hereinafter referred to as "the present compound 25") was synthesized in the same manner as in Production Example 16 except for using 2- ( 3-ethylsulfanyl-5-trifluoromethyl- pyridin-2-yl ) -3-methyl-6-trifluoromethylsulfanyl-3H- imidazo[ 4 , 5-b] pyridine instead of 2- ( 3-ethylsulfanyl- pyridin-2-yl ) -3-methyl-6-trifluoromethylsulfanyl-3H- imidazo[ 4 , 5-b] pyridine .
The present compound 25
Figure imgf000376_0001
"""H-NMR (CDC13) δ: 9.28 (lH,d), 9.10 (lH,d), 8.80 (,lH,d), 8.72 (lH,d), 3.98 (3H,s), 3.93 (2H,q), 1.43 (3H,t).
[ 0360]
Production Example 25
A mixture of 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -5-iodo- 1-methyl-lH-benzimidazole (340 mg) , copper iodide (410 mg) , sodium pentafluoropropionate (800 mg) , NMP (5 ml), and xylene (5 ml) was stirred at 160°C for 5 hours. The reaction mixture was allowed to cool to room temperature, and then saturated aqueous sodium hydrogen carbonate solution and 28% ammonia solution were poured thereto. Then, the mixture was extracted with t-butylmethyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- ethylsulfanyl-pyridin-2-yl ) -1-methyl-5-pentafluoroethyl-lH- benzimidazole (240 mg) , which is hereinafter referred to as "the present compound 26".
The present compound 26
Figure imgf000377_0001
1H-NMR (CDC13) δ : 8.50 (lH,dd), 8.16 (lH,s), 7.77 (lH,dd), 7.57 (lH,d), 7.53 (lH,d), 7.36 (lH,dd), 3.93 (3H,s), 2.94 (2H, q) , 1.33 (3H, t) .
[ 0361]
Production Example 26
2- ( 3-ethylsulfonyl-pyridin-2-yl ) -l-methyl-5- pentafluoroethyl-lH-benzimidazole (hereinafter referred to as "the present compound 27") was synthesized in the same manner as in Production Example 5 except for using 2- (3- ethylsulfanyl-pyridin-2-yl ) -1-methyl-5-pentafluoroethyl-lH- benzimidazole instead of 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4,5-b] pyridine.
The present compound 27
Figure imgf000378_0001
^- MR (CDC13) δ: 8.98 (lH,dd), 8.53 (lH,dd), 8.06 (lH,s), 7.70 (lH,dd), 7.60 (lH,d), 7.56 (lH,d), 3.86-3.78 (5H,m), 1.34 (3H, t) .
[ 0362]
Production Example 27
To a mixture of 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethylsulfanyl-3H-imidazo[ 4 , 5-b] pyridine (0.18 g) and chloroform (4 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.21 g) while ice-cooling, and then the mixture was- stirred while ice-cooling for 5 minutes. To the reaction mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and the mixture was extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethylsulfanyl-3H-imidazo[ 4 , 5-b] pyridine (0.16 g) , which is hereinafter referred to as "the present compound 29" .
The present compound 29
Figure imgf000379_0001
1H-NMR (CDC13) δ: 9.10-9.07 (lH,m), 8.94-8.91 (lH,m), 8.77- 8.74 (lH,m), 8.46-8.44 (lH,m), 4.38 (3H,s), 3.76-3.65 (lH,m), 3.16-3.05 (lH,m), 1.49 (3H,t).
[ 0363]
Production Example 28(1)
3-chloro-pyridin-2-carboxylic acid (2-methylamino-5- trifluoromethyl-phenyl ) -amide (hereinafter referred to as "intermediate compound (M20-29)") was synthesized in the same manner as in Production Example 9(1) except for using N1-methyl-4-trifluoromethyl-benzene-1 , 2-diamine instead of 5-iodo-N2-methyl-pyridin-2 , 3-diamine .
Figure imgf000379_0002
1H-NMR (CDCI3) δ: 9.56 (lH,s), 8.55-8.54 (lH,m), 7.91 (lH,dd), 7.70 (lH,d), 7.49-7.43 (3H,m), 6.79 (lH,d), 2.93 (3H,d) .
[ 0364]
Production Example 28(2)
A mixture of the intermediate compound (M20-29) (800 mg) , sodium ethanethiolate (350 mg) , and DMF (10 ml) was stirred at 100°C for 5 hours. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and. then the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- ethylsulfanyl-pyridin-2-yl ) -1-methyl-5-trifluoromethyl-lH- benzimidazole (410 mg) , which is hereinafter referred to as "the present compound 30".
The present compound 30
Figure imgf000380_0001
"""H-NMR (CDC13) δ: 8.51 (lH,dd), 8.17 (lH,d), 7.78 (lH,dd), 7.61 (lH,dd), 7.52 (lH,d), 7.38 (lH,dd), 3.93 (3H,s), 2.94 (2H, q) , 1.33 (3H, t) .
[ 0365]
Production Example 29, 30
2- (3-ethylsulfinyl-pyridin-2-yl ) -l-methyl-5- trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 31") and 2- ( 3-ethylsulfonyl- pyridin-2-yl ) -l-methyl-5-trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 32") were synthesized in the same manner as in Production Examples 2 and 3 except for using 2- ( 3-ethylsulfanyl-pyridin-2-yl ) -1- methyl-5-trifluoromethyl-lH-benzimidazole instead of 2- (3- ethylsulfanyl pyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4, 5-b] pyridine.
The present compound 31
Figure imgf000381_0001
1H-NMR (CDC13) δ: 8.77 (lH,d), 8.61 (lH,d), 8.05 (lH,s),
7.61 (lH,dd), 7.55 (lH,d), 7.48 (lH,d), 4.20 (3H,s), 3.73- 3.61 (lH,m), 3.11-3.00 (lH,m), 1.47 (3H,t).
The present compound 32
Figure imgf000381_0002
XH-NMR (CDCI3) δ: 8.95 (lH,dd), 8.50 (lH,dd), 8.09 (lH,d), 7.66 (lH,dd), 7.61 (lH,d), 7.53 (lH,d), 3.83 (2H,q), 3.75 (3H, s) , 1.33 (3H, t) . [ 0366]
Production Example 31(1)
3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid (2-methylamino-5-trifluoromethyl-phenyl ) -amide (hereinafter referred to as "intermediate compound (M20-31)") was synthesized in the same manner as in Production Example 9(1) except for using N1-methyl-4 -trifluoromethyl-benzene- 1,2-diamine and 3-chloro-5-trifluoromethylpyridin-2- carboxylic acid instead of 5-iodo-N2-methyl-pyridin-2 , 3- diamine and 3-chloro-pyridin-2-carboxylic acid.
Figure imgf000382_0001
1H-NMR (CDC13) δ : 9.42 (lH,s), 8.80 (lH,d), 8.16 (lH,d), 7.71 (lH,s), 7.47 (lH,d), 6.81 (lH,d), 4.32 (lH,s), 2.93 (3H,d) ..
[ 0367]
Production Example 31(2)
2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-trifluoromethyl-lH-benzimidazole (hereinafter referred. to as "the present compound 33") and 3- ethylsulfanyl-5-trifluoromethyl-pyridin-2-carboxylic acid (2-methylamino-5-trifluoromethyl-phenyl ) -amide (hereinafter referred to as "intermediate compound (M3-32)") were synthesized in the same manner as in Production Example 28(2) except for using the intermediate compound (M20-31) instead of 3-chloro-pyridin-2-carboxylic acid (2- methylamino-5-trifluoromethyl-phenyl ) -amide .
The present compound 33
Figure imgf000383_0001
XH-NMR (CDCI3) δ: 8.72 (lH,d), 8.21 (lH,d), 7.91 (lH,d), 7.63 (lH,d), 7.54 (lH,d), 4.00 (3H,s), 3.00 (2H,q), 1.38 (3H, t) .
Intermediate compound (M3-32)
Figure imgf000383_0002
^"H-NMR (CDCI3) δ: 9.64 (lH,s), 8.53 (lH,d), 7.86 (lH,s), 7.76 (lH,d), 7.41 (lH,dd), 6.76 (lH,d), 4.35 (lH,d), 2.96 (2H,q), 2.90 (3H,d), 1.44 (3H,t) .
[ 0368]
Production Examples 32 and 33
2- ( 3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 34") and 2- (3- ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl ) -l-methyl-5- trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 35") were synthesized in the same manner as in Production Examples 2 and 3 except for using 2- (3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-trifluoromethyl-lH-benzimidazole instead of 2-(3- ethylsulfanyl pyridin-2-yl ) -3-methyl^6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine.
The present compound 34
Figure imgf000384_0001
1H-NMR (CDCI3) δ: 9.05 (lH,d), 8.91 (lH,d), 8.12 (lH,d), 7.67 (lH,dd), 7.60 (lH,d), 4.32 (3H,s), 3.80-3.70 (lH,m), 3.15-3.05 (lH,m), 1.51 (3H,t).
The present compound 35
Figure imgf000384_0002
■""H-NMR (CDCI3) δ: 9.22 (lH,d), 8.77 (lH,d), 8.10 (lH,d), 7.66 (lH,dd), 7.57 (lH,d), 3.98 (2H,q), 3.84 (3H,s), 1.40 (3H,t). -
[ 0369] Production Example 34, 35
To a mixture of 2- ( 3-ethylsulfonylpyridin-2-yl ) -3- methyl-6-trifluoromethyl-3H-imidazo[ 4, 5-b] pyridine (550 mg) and chloroform (15 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (750 mg) , and the mixture was heated under reflux for 20 hours. To the reaction mixture was poured aqueous 10% sodium 'thiosulfate ' solution, and the mixture was extracted with chloroform. The organic layerwas washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfonyl-l-oxy pyridin-2-yl) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (168 mg) , which is hereinafter referred to as "the present compound 36" and 2- ( 3-ethylsulfonylpyridin-2-yl ) -3-methyl-6-trifluoromethyl- 3H-imidazo[ , 5-b] pyridine 4-oxide (73 mg) , which is hereinafter referred to as "the present compound 37".
The present compound 36
Figure imgf000385_0001
1H-NMR (CDC13) δ: 8.79 (lH,.d), 8.54 (lH,dd), 8.33 (lH,d), 7.99 (lH,dd), 7.69 (lH,dd), 3.85-3.74 (4H,m) , 3.52-3.42 (lH,m) , 1.34 (3H, t) .
The present compound 37
Figure imgf000386_0001
"""H-NMR (CDC13) δ: 9.03 (lH,dd), 8.53 (lH,dd), 8.47 (lH,d), 7.92 (lH,d), 7.77 (lH,dd), 4.29 (3H,s), 3.69 (2H,q), 1.36 (3H,t).
[ 0370]
Production Example .36 ( 1 )
2- ( 3-chloro-5-trifluoromethyl-pyridin-2-yl ) -5-iodo-l- methyl-lH-benzimidazole (hereinafter referred to as "intermediate compound ( 6-41)") was synthesized in the same manner as in Production Example 4(1) except for using
4-iodo-N1-methyl-benzene-l, 2-diamine instead of N2-methyl-
5-trifluoromethylpyridin-2 , 3-diamine .
Intermediate compound (M6-41)
Figure imgf000386_0002
XH-NMR (CDCI3) δ: 8.92 (lH,d), 8.23 (lH,d), 8.17 (lH,d), 7.66 (lH,dd), 7.23 (lH,d), 3.85 (3H,s).
[ 0371]
Production Example 36(2) 2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -5- iodo-l-methyl-lH-benzimidazole (hereinafter referred to as "the present compound 45") was synthesized in the same manner as in Production Example 1(2) except for using the intermediate compound (M6-41) instead of 2- (3- fluoropyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine .
The present compound 45
Figure imgf000387_0001
[ 0372]
Production Example 36(3)
2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-pentafluoroethyl-ΙΗ-benzimidazole (hereinafter referred to as "the present compound 38") was synthesized in the same manner as in Production Example 25 except for using 2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -5- iodo-l-methyl-lH-benzimidazole instead of 2-(3- ethylsulfanyl-pyridin-2-yl ) -5-iodo-l-methyl-lH- benzimidazole .
The present compound 38
Figure imgf000388_0001
1H-NMR (CDCI3) δ: 8.72 (lH,d), 8.20 (lH,s), 7.91 (lH,d), 7.60 (lH,d), 7.55 (lH,d), 4.00 (3H,s), 3.01 (2H,q), 1.39 (3H,t).
[ 0373]
Production Example 37, 38
2- ( 3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-pentafluoroethyl-lH-benzimidazole (hereinafter referred to as "the present compound 39") and 2- (3- ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl ) -l-methyl-5- pentafluoroethyl-lH-benzimidazole (hereinafter referred to as "the present compound 40") were synthesized in the same manner as in Production Examples 2 and 3 except for using 2- ( 3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl ) -1- methyl-5-pentafluoroethyl-lH-benzimidazole instead of 2- (3- ethylsulfanylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4, 5-b] pyridine.
The present compound 39
Figure imgf000388_0002
^H-NMR (CDCI3) δ: 9.05 (lH,d), 8.91 (lH,d), 8.10 (lH,s), 7.66-7.60 (2H,m), 4.33 (3H,s), 3.80-3.69 (lH,m), 3.17-3.07 (lH,m) , 1.50 (3H, t) .
The present compound 40
Figure imgf000389_0001
1H-N R (CDCI3) δ: 9.22 (lH,d), 8.77 (lH,d), 8.08 (lH,s), 7.63 (lH,d), 7.58 (lH,d), 3.99 (2H,q), 3.84 (3H,s), 1.40 (3H,t).
[ 0374]
Production Example 39(1)
To a mixture of methyl- (2-nitro-4-trifluoromethyl- phenyl ) -amine (16 g) and acetonitrile (200 ml) was added N- bromosuccinimide (15 g) while ice-cooling. The reaction mixture was stirred at room temperature for 5 hours. To the resulting reaction mixture was poured saturated aqueous sodium hydrogen carbonate solution, and then the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give (2-bromo-6-nitro-4- trifluoromethyl-phenyl ) -methyl-amine (15 g) .
( 2-bromo- 6-nitr0-4 -trifluoromethyl-phenyl ) -methyl-amine
Figure imgf000390_0001
1H-NMR (CDCI3) δ: 8.12 (lH,s), 7.86 (lH,s), 6.48 (lH,brs), 3.07 (3H,d).
[ 0375]
Production Example 39(2)
To a mixture of an iron powder (11 g) , acetic acid (12 ml), THF (40 ml), and water (10 ml) was added dropwise a mixture of (2-bromo-6-nitro-4-trifluoromethyl-phenyl ) - methyl-amine (10 g) and THF (50 ml) while stirring and heating at 70°C. After that, the mixture was stirred at 70°C for 3 hours. The resulting reaction mixture was filtered through celite (registered trademark), and washed with THF. The resulting filtrate was concentrated under reduced pressure. . To the resulting residue was poured 10% sodium hydroxide aqueous solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to give 3-bromo-N2-methyl-5-trifluoromethyl- benzene-l , 2-diamine (11 g) .
3-bromo-N2-methyl-5-trifluoromethyl-benzene-l , 2-diamine
Figure imgf000390_0002
[ 0376]
Production Example 39(3)
3-chloro-pyridin-2-carboxylic acid (3-bromo-2- methylamino-5-trifluoromethyl-phenyl ) -amide (hereinafter referred to as "intermediate compound (M20-43)") was synthesized in the same manner as in Production Example 9(1) except for using 3-bromo-N2-methyl-5-trifluoromethyl- benzene-1 , 2-diamine instead of 5-iodo-N2-methyl-pyridin- 2,3-diamine.
Figure imgf000391_0001
1H-NMR (CDCI3) δ: 10.63 (lH,s), 8.77 (lH,d), 8.58 (lH,dd), 7.91 (lH,dd), 7.56 (lH,d), 7.47 (lH,dd), 3.75-3.68 (lH,m), 2.83 (3H,d) .
[ 0377]
Production Example 39(4)
2- ( 3-ethylsulfanyl-pyridin-2-yl ) -7-bromo-l-methyl-5- trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 75"), 3-ethylsulfanyl-pyridin-2- carboxylic acid ( 3-bromo-2-methylamino-5-trifluoromethyl- phenyl ) -amide (hereinafter referred to as "intermediate compound (M3-42 )" ) and 2- ( 3-chloro-pyridin-2-yl ) -7-bromo-l- methyl-5-trifluoromethyl-lH-benzimidazole (hereinafter referred to as "intermediate compound (M6-43)") were synthesized in the same manner as in Production Example 28(2) except for using the intermediate compound (M20-43) instead of the intermediate compound (M20-29) .
The present compound 75
Figure imgf000392_0001
"""H-NMR (CDC13) δ: 8.54 (lH,dd), 8.08 (lH,d), 7.79 (lH,dd), 7.72. (lH,d), 7.40 (lH,dd), 4.13 (3H,s), 2.94 (2H,q), 1.32 (3H, t) .
Intermediate compound (M3-42)
Figure imgf000392_0002
1H-NMR (CDCI3) δ: 10.80 (lH,s), 8.82 (lH,s), 8.38 (lH,dd), 7.74 (lH,d), 7.54 (lH,s), 7.42 (lH,dd), 3.75-3.65 (lH,brm) , 2.97 (2H,q), 2.82 (3H,d), 1.45 (3H,t).
Intermediate compound (M6-43)
Figure imgf000392_0003
1H-NMR (CDCI3) δ: 8.71 (lH,dd), 8.08 (lH,d), 7.95 (lH,dd), 7.74 (lH,d), 7.47 (lH,dd), 4.09 (3H,s).
[ 0378]
Production Example 4Ό
2- ( 3-ethylsulfonyl-pyridin-2-yl ) -7-bromo-l-methyl-5- trifluoromethyl-lH-benzimidazole (hereinafter referred to as "the present compound 46") was synthesized in the same manner as in Production Example 5 except for using 2- (3- ethylsulfanyl-pyridin-2-yl ) -7-bromo-l-methyl-5- trifluoromethyl-lH-benzimidazole instead of 2- (3- ethylsulfanyl-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4,5-b] pyridine.
The present compound 46
Figure imgf000393_0001
■""H-NMR (CDC13) δ: 8.99 (lH,dd), 8.51 (lH,dd), 8.00 (lH,d), 7.75 (lH,d), 7.72 (lH,dd), 4.03. (3H,s), 3.73 (2H,q), 1.33 (3H,t) .
[ 0379]
Production Examples 41 and 42
A mixture of 2- ( 3-ethylsulfanyl-5- trifluoromethylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (1.0 g) , m-chloroperbenzoic acid (purity: not less than 65%) (2.72 g) and chloroform (5 ml) was refluxed for 8 hours, and m-chloroperbenzoic acid (purity: not less than 65%) (2.0 g) was added thereto, and the mixture was further refluxed for5 hours. To the cooled reaction mixture was poured aqueous 10% sodium thiosulfate solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2- ( 3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl ) -3-methyl-6- trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine 4-oxide (362 mg) , which is hereinafter referred to as "the present compound 47"), and 2- ( 3-ethylsulfonyl-l-oxy-5- trifluoromethylpyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (45 mg) , which is hereinafter referred to as "the present compound 51".
The present compound 47
Figure imgf000394_0001
"""H-NMR (CDC13) δ: 9.27 (lH,d), 8.76 (lH,d), 8.49 (lH,d), 7.94 (lH,d), 4.33 (3H,s), 3.80 (2H,q), 1.40 (3H,t).
The present compound 51
Figure imgf000395_0001
1H-NMR (CDCI3) δ: 8.75 (lH,s), 8.50 (lH,s), 8.12 (lH,s), 7.94 (lH,s), 4.28 (3H,s), 3.75-3.65 (lH,m), 3.55-3.44 (lH,m) , 1.38 (3H, t) .
[ 0380]
Production Example 43(1)
A mixture of 2-chloro-3-nitro-5- trifluoromethylpyridine (2.60 g), 2 , 2 , 2-trifluoroethylamine
(0.79 g) , N, N-diisopropylethylamine (1.04 g) and N-methyl- 2-pyrrolidone (5 ml) was stirred at room temperature for 10 hours. To the reaction mixture was poured aqueous 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give ( 3-nitro-5-trifluoromethylpyridin- 2-yl) - (2, 2, 2-trifluoroethyl) amine (1.83 g) .
( 3-nit o-5-trifluoromethylpyridin-2-yl ) - ( 2 , 2 , 2- trifluoroeth l ) amine
Figure imgf000395_0002
1H-N R (CDCI3) δ: 8.72 (lH,d), 8.68 (lH,d), 8.59 (lH,brs), 4.54- .41 (2H,m) .
[ 0381]
Production Example 43(2)
A mixture of an iron powder (2.12 g) , ethanol 6 ml), water 4 ml) and acetic acid 0.1 ml) was added dropwise a mixture of ( 3-nitro-5-trifluoromethylpyridin-2-yl ) - ( 2 , 2 , 2- trifluoroethyl ) amine (1.83 g) and ethanol (10 ml) at 70°C, and then the mixture was stirred at 70°C for 1 hour. After allowing to cool, the cooled reaction mixture was filtrated To the filtrate was added water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure- to give N2- ( 2 ,2 , 2-trifluoroethyl ) -5- trifluoromethylpyridin-2 , 3-diamine (1.59 g) .
N2- ( 2 , 2 , 2-trifluoroethyl ) -5-trifluoromethylpyridin-2 , 3- diamine
Figure imgf000396_0001
XH-NMR (CDC13) δ : 8.04-8.02 (lH,m), 7.10-7.07 (lH,m), 4.81 (lH,brs), 4.31-4.20 (2H,m), 3.34 (2H,brs).
[ 0382]
Production Example 43(3)
A mixture of N2- ( 2 , 2 , 2-trifluoroethyl ) -5- trifluoromethylpyridin-2 , 3-diamine (0.52 g) , 3- ethylsulfanylpyridin-2-carboxylic acid (0.37 g) , WSC (0.46 g) , HOBt (27 mg) and pyridine (2 ml) was stirred at room temperature for 3 hours. To the reaction mixture was poured aqueous 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give 3-ethylsulfanyl pyridin-2-carboxylic acid [ 2- ( 2 , 2 , 2-trifluoroethyl ) amino-5- trifluoromethylpyridin-3-yl] amide (0.75 g) , which is hereinafter referred to as "intermediate compound (M3-43)". Intermediate compound (M3-43)
N NH
^CF3
[ 0383]
Production Example 43(4)
A mixture of the intermediate compound (M3-43) (0.75 g) and acetic acid (5 ml) was stirred while heating under reflux for 2 days. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanylpyridin-2-yl ) -3- ( 2 , 2 , 2- trifluoroethyl ) -6-trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.53 g) , which is hereinafter referred to as "the present compound 65".
The present compound 65
Figure imgf000398_0001
1H-NMR (CDC13) δ: '8.77-8.74 (lH,m), 8.48 (lH,dd), 8.45-8.42 (lH,m), 7.82 (lH,dd), 7.40 (lH,dd), 5.64 (2H,q), 2.99
(2H,q) , 1.35 (3H, t) .
[ 0384]
Production Example 44(1)
A mixture of N2- ( 2 , 2 , 2-trifluoroethyl ) -5- trifluoromethylpyridin-2 , 3-diamine (0.52 g) , 3- ethylsulfanyl-5-trifluoromethylpyridin-2-carboxylic acid (0.50 g) , WSC (0.46 g) , HOBt (27 mg) and pyridine (2 ml) was stirred at room temperature for 3 hours. To the reaction mixture was poured aqueous ' 10% citric acid solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to give 3-ethylsulfanyl-5-trifluoromethylpyridin- 2-carboxylic acid [ 2- (2, 2, 2-trifluoroethyl) amino-5- trifluoromethylpyridin-3-yl] amide (0.89 g) , which is hereinafter referred to as "intermediate compound (M3-44)". Intermediate compound (M3-44)
Figure imgf000399_0001
[ 0385]
Production Example 44 (2 )
A mixture of the intermediate compound (M3-44) (0.89 g) , p-toluenesulfonic acid monohydrate (1.14 g)., N-methyl- 2-pyrrolidone (10 ml) and xylene (10 ml) was heated under reflux while dehydrating with the Dean-Stark apparatus for 8 hours, and then the reaction mixture was allowed to cool. To the cooled reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2-(3- ethylsulfanyl-5-.trifluoromethylpyridin-2-yl ) -3- ( 2 , 2 , 2- trifluoroethyl ) -6-trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.76 g) , which is hereinafter referred to as "the present compound 66".
The present compound 66
Figure imgf000399_0002
1H-NMR (CDCI3) δ: 8.80 (lH,d), 8.70 (lH,d), 8.48 (lH,d), 7.96 (lH,d), 5.67 (2H,q), 3.04 (2H,q), 1.40 (3H,t).
[ 0386]
Production Example 45
To a mixture of the present compound 65 (0.32 g) and chloroform . (2 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.36 g) while ice-cooling. The mixture was heated, to room temperature, and stirred 1 hour. To the mixture were added saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and then the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfonylpyridin-2- yl) -3- (2,2, 2-trifluoroethyl ) -6-trifluoromethyl-3H- imidazof 4 , 5-b] pyridine (0.32 g) , which is hereinafter referred to as "the present compound 67".
The present compound 67
Figure imgf000400_0001
"""H-NMR (CDCI3) δ: 8.98 (lH,dd), 8.80 (lH,d), 8.59 (lH,dd),
8.37 (lH,d), 7.75 (lH,dd), 5.31 (2H,q), 3.95 (2H,q), 1.40 (3H, t) .
[ 0387]
Production Example 46
To a mixture of the present compound 66 (0.32 g) and chloroform (2 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.31 g) while ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour. To the mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate' solution, and the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude product was washed with hexane to give 2- ( 3-ethylsulfonyl-5-trifluoromethylpyridin- 2-yl) -3- (2, 2, 2-trifluoroethyl ) -6-trifluoromethyl-3H- imidazot , 5-b] pyridine (0.28 g) , which is hereinafter referred to as "the present compound 68".
The present compound 68
Figure imgf000401_0001
^"H-NMR (CDC13) δ : 9.22 (lH,d), 8.83-8.83 (2H,m) , 8.40 (lH,d), 5.36 (2H,q), 4.05 (2H,q), 1.45 (3H,t).
[ 0388] Production Example 47(1)
A mixture of 2-chloro-5-iodopyridine (20.0 g) , sodium pentafluoropropionate (77.8 g) , copper (I) iodide (31.8 g) , xylene (84 ml) and N-methyl pyrrolidone (84 ml) was heated to 160°C, and stirred while heating under reflux 6 hours. The reaction mixture was cooled to room temperature, and water was poured thereto. Then, the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 2-chloro-5-pentafluoroethyl pyridine .
2-c-hloro-5-pentafluoroethyl pyridine
Figure imgf000402_0001
""■H-NMR (CDC13) δ: 8.65-8.62 (lH,m), 7.85-7.81 (lH,m), 7.48- 7.44 (lH,m)
[ 0389]
Production Example 47(2)
A mixture of the half amount of 2-chloro-5- pentafluoroethyl pyridine obtained in Production Example 47(1), zinc (II) cyanide (14.4 g) , tetrakistriphenylphosphine palladium (2.42 g) and N-methyl pyrrolidone (84 ml) was heated to 80°C, and stirred for 2.5 hours. The reaction mixture was cooled to room temperature, and water and methyl-tert-butyl ether were poured thereto. The resulting precipitate was filtrated through celite (registered trademark) , and the residue was washed with methyl-tert-butyl ether. The filtrate was extracted with methyl-tert-butyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2-cyano-5-pentafluoroethyl pyridine .(4.19 g) .
2-cyano-5-pentafluoroethyl pyridine
Figure imgf000403_0001
1H-NMR (CDC13) δ : 8.97-8.96 (lH,m), 8.12-8.09 (lH,m), 7.90- 7.87 (lH,m)
[ 0390]
Production Example 47(3)
A mixture of water (17 ml) and concentrated sulfuric acid (17 ml) was heated to 100°C, and thereto was added dropwise 2-cyano-5-pentafluoroethyl pyridine (3.81 g) while heating. Then, the mixture was stirred at 100°C for 2.5 hours. After cooling to room temperature, the reaction mixture was poured to ice water. The precipitated solid was filtrated and washed with water. The resulting solid was dried under reduced pressure to . give 5- pentafluoropyridin-2-carboxylic acid (3.52 g) . 5-pentafluoropyridin-2-carboxylie acid
Figure imgf000404_0001
1H-NMR (CDCI3) δ: 8.92-8.88 (lH,m), 8.44-8.39 ( 1H, m) , . 8.25- 8.20 (lH,m)
[ 0391]
Production Example 47(4)
A mixture of tetramethyl piperidine (5.5 ml) and THF (58 ml) was cooled to -78°C, and thereto was added dropwise a solution of 1.6M n-butyl lithium in hexane. After heating to room temperature, the mixture was stirred for 10 minutes. The mixture was cooled to -78 °C again, and thereto was added dropwise a solution of 5-pentafluoropyridin-2- carboxylic acid (3.52 g) in THF. Then, the mixture was stirred at -78°C for 1 hour, and thereto was added dropwise diethyl disulfide (4.0 ml) at -78°. After heating to room temperature, the mixture was stirred for 1 hour. To the reaction mixture was poured IN hydrochloric acid, followed by a 5N aqueous sodium hydroxide solution. . Then, the aqueous layer was washed with methyl-tert-butyl ether, and thereto was poured 12N hydrochloric acid. The precipitated solid . was filtrated, and dissloved in methyl-tert-butyl ether. The solid was dried over sodium sulfate, and concentrated under reduced pressure to give 3- ethylsulfanyl-5-pentafluoroethyl pyridin-2-carboxylic acid (1.99 g) , which is hereinafter referred to as "intermediate compound (M2-7)".
Intermediate compound (M2-7)
Figure imgf000405_0001
1H-NMR (CDC13) δ: 8.51-8.50 (lH,m), 7.89-7.87. (lH,m), 3.01 (2H,q), 1.46 (3H,t)
[ 0392]
Production Example 47(5)
A mixture of N2-methyl-5-trifluoromethylpyridin-2 , 3- diamine (0.50 g) , the intermediate compound (M2-7) (0.79 g) , WSC (0.37 g) , HOBt (35 mg) and pyridine (5 ml) was stirred at room temperature for 3 hours. To the reaction mixture was poured water, and then the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 3-ethylsulfanyl-5-pentafluoroethyl pyridin-2- carboxylic ..acid (2-methylamino-5-trifluoromethylpyridin-3- yl ) amide, which is hereinafter referred to as "intermediate compound (M3-45)".
Intermediate compound (M3-45)
Figure imgf000406_0001
1H-NMR , (CDCI3) δ: 9.57 (lH,brs), 8.54-8.52 (lH,m), 8.37- 8.35 (lH,m), 7.94-7.92 (lH,m), 7.89-7.87 (lH,m), 4.97 (lH,brs), 3.08 (3H,d), 2.99 (2H,q), 1.45 (3H,t)
A mixture of the total amount of the resulting intermediate compound ( 3-45) and acetic acid (5 ml) was heated to 120°C, and stirred while heating under reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- (3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl ) -3- methyl-6-trifluoromethyl-3H-imidazo[ 4 , 5-b] pyridine (0.77 g) , which is hereinafter referred to as "the present compound 71".
The present compound 71
Figure imgf000406_0002
XH-NMR (CDCI3) δ: 8.78-8.76 (lH,m), 8.71-8.69 (lH,m) , 8.44- 8.42 (lH,m), 7.91-7.89 (lH,m), 4.13 (3H,s), 3.02 (2H,q), 1.39 (3H,t) [ 0393]
Production Example 48
To a mixture of the present compound 71 (0.47 g) and chloroform (10 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.57 g) while ice-cooling. Then, the mixture was heated to room temperature, and stirred for 1 hour. To the mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and then the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate,, and concentrated under reduced pressure. The crude product was subjected, to silica gel column chromatography to give 2- ( 3-ethylsulfonyl-5- pentafluoroethy.lpyridin-2-yl ) -3-methyl-6-trifluoromethyl- 3H-imidazo[ 4 , 5-b] pyridine (0.39 g) , which is hereinafter referred to as "the present compound 72".
The present compound 72
Figure imgf000407_0001
!fi- MR (CDC13) δ: 9.21-9.19 (lH,m), 8.81-8.79 (lH,m), 8.76-
8.75 (lH,m), 8.35-8.33 (lH,m), 3.99-3.93 (5H,m), 1.41 (3H,t)
[ 0394] Production Example 49 .
A mixture of N2-methyl-5-pentafluoroethylpyridin-2 , 3- diamine (0.50 g) , the intermediate compound (M2-7) (0.62 g) , WSC (0.29 g) , HOBt (28 mg) and pyridine (.4 ml) was stirred at room temperature for 3 hours . To the reaction mixture was poured water, and the mixture was extracted with methyl-tert-butyl ether. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 3-ethylsulfanyl-5-pentafluorpethylpyridin-2- carboxylic acid ( 2-methylamino-5-pentafluoroethyl pyridin- 3-yl) amide, which is hereinafter referred to as "intermediate compound (M3-46)".
Figure imgf000408_0001
1H-NMR (CDCI3) δ: 9.59 (lH,brs), 8.54-8.52 (lH,m), 8.32- 8.30 (lH,m), 7.89-7.87 (lH,m), 7.85-7.83 (lH,m), 5.04 (lH,brs), 3.09 (3H,d), 2.99 (2H,q), 1.45 (3H,t)
A mixture of the . total amount of the resulting intermediate compound (M3-46) and acetic acid (4 ml) was heated to 120°C, and stirred while heating under reflux for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography to give 2- ( 3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl ) -3- methyl-6-pentafluoroethyl-3H-imidazo[ , 5-b] pyridine (0.84 g) , which is hereinafter referred to as "the present compound 73".
The present compound 73
Figure imgf000409_0001
XH-N R (CDC13) δ : 8.72-8.69 (2H,m), 8.42-8.41 (lH,m), 7.90- 7.89 (lH,m), 4.15-4.12 (3H,m) , 3.02 (2H,q), 1.40 (3H,t)
[ 0395]
Production Example 50
To the mixture of the present compound 73 (0.54 g) and chloroform (11 ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.59 g) while ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour. To the mixture were poured saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and then the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to . silica gel column chromatography to give 2- ( 3-ethylsulfonyl-5- pentafluoroethyl pyridin-2-yl ) -3-methyl-6-pentafluoroethyl- 3H-imidazo[ 4 , 5-b] pyridine (0.34 g) , which is hereinafter referred to ,as "the present compound 74".
The present compound 74 ·
Figure imgf000410_0001
■""H-NMR (CDC13) δ: 9.21-9.20 (lH,m), 8.77-8.74 (2H,m), 8.32- 8.31 (lH,m), 4.00-3.94 (5H,m) , 1.41 (3H,t)
[ 039.6]
The compounds as described in Production Examples and the compounds produced in the same manner as in Production Examples are shown below.
[ 0397]
A com ound represented by the formula (1) :
Figure imgf000410_0002
wherein R1, R2, R3, R4, R5, R6, A1, A2, A3 and n are any of the combinations as listed in [ Table 36] to [ Table 58] .
[ 0398]
[ Table 36]
Figure imgf000410_0003
2 Et H H H CF3 H NMe CH N 1
3 Et H H H CF3 H NMe CH N 2
4 Et H CF3 H CF3 H NMe CH N 0
5 Et H CF3 H CF3 H NMe CH N 2
6 Et H H H CF2CF3 H NMe CH N 0
7 Et H H H CF2CF3 H NMe CH N 1
8 Et H H H CF2CF3 H NMe CH N 2
9 Et H H H I H NMe CH N 0
10 Et H CF3 H CF3 H S CH N 0
11 Et H CF3 H . CF3 H S CH N 2
12 Et H H H CF3 H S CH N 2.
13 Et H H H SCF3 H NMe CH N 0
14 Et H H H SCF3 H NMe CH N 1
15 Et H H H SCF3 H NMe CH N 2
16 Et H H H S02CF3 H NMe CH N 2
17 Et H CF3 H CF2CF3 H NMe CH N 0
18 Et H CF3 H CF2CF3 H NMe CH . N 1
19 Et , H CF3 H CF2CF3 H NMe CH N 2
20 Et H H H SOCF3 H NMe CH N 2
21 Et H H H I H NMe CH CH 0
22* Et . H H H CF3 H S CH N 2
23 Et H H H SF5 H NMe CH CH 0
24 Et H H Ή SF5 H NMe CH CH 2
25 Et H CF3 H S02CF3 H NMe CH N 2
[ 0399]
[ Table 37]
Figure imgf000411_0001
45 Et H CF3 H I H NMe CH CH 0
46 Et H H H CF3 H NMe CH CBr 2
47* Et H H H CF2CF3 H NMe CH CH 2
48* Et H CF3 H CF3 H NMe CH N 2
49 Et H H H OCF3 H NMe CH CH 0
50 Et H H H OCF3 H NMe CH CH 2
[ 0400]
[ Table 38]
Figure imgf000412_0002
[ 0401]
[ Table 39]
Figure imgf000412_0001
78 Et H CF3 H CF3 H NH CH N 0
79 Et H CF3 H CF3 H NH CH N 2
80 Et H H H CF3 H 0 CH N 0
81 Et H H H CF3 H 0 CH N 2
82 Et H CF3 H CF3 H 0 CH N 0
83 Et H CF3 H CF3 H 0 CH N 2
84 Et H H H CF3 H 0 CH CH 0
85 Et H H H CF3 H 0 CH CH 2
86 Et H CF3 H CF3 H 0 CH CH 0
87 Et H CF3 H CF3 H 0 CH CH 2
88 Et H H H CF3 CI NMe CH N 2
89 Et H CF3 H CF3 CI NMe CH N 2
90 Et H H H CF3 SEt NMe CH N 2
91 Et H CF3 H CF3 SEt NMe CH N 2
92 Et H H H CF3 OH NMe CH N 2
93 Et H CF3 H CF3 OH NMe CH N 2
94 Et H H H CF3 OMe NMe CH N 2
95 Et H GF3 H CF3 OMe NMe CH N 2
96 Et H H H CF3 SMe NMe CH N 2
97 Et H CF3 H CF3 SMe NMe CH N 2
98 Et H H H CF3 N e2 NMe CH N 2
99 Et H CF3 H CF3 NMe2 NMe CH N 2
100 Et H H H CF3 Ph NMe CH N 2
[ 0402]
[ Table 40]
Figure imgf000413_0001
pyridyl
115 Et H OCF3 H CF3 H NMe CH N 2
116 Et H SCF3 H CF3 H NMe CH N 2
117 Et H SOCF3 H CF3 H NMe CH N 2
118 Et H SQ2CF3 H CF3 H NMe CH N 2
119 Et H CF(CF3)2CF3 H CF3 H NMe CH N 2
120 Et H CF2CF2CF3 H CF3 H NMe CH N 2
121 Et H Br H CF3 H NMe CH N 2
122 Et H I H CF3 H NMe CH N 2
123 Et H Me H CF3 . H NMe CH N 2
124 Et H OMe H CF3 H NMe CH N 2
125 Et H H H CF(C H NMe CH N 2 F3 ) 2
[ 0403]
Figure imgf000414_0001
[ 0404]
[ Table 42]
Figure imgf000415_0002
[ 0405]
[ Table 43]
Figure imgf000415_0001
187 Et H H H Br H NMe CH N 1
188 Et H H H Br H NMe CH N . 2
189 Et H H H I H NMe CH N 1
190 Et H H H I H NMe CH N 2
191 Et H H H CN H NMe CH N 0
192 Et H H H CN H NMe CH N 1
193 Et H H H CN H NMe CH N 2
194 Et H H H CHO H NMe CH N 0
195 Et H H H CF2H H NMe CH N 0
196 Et H H H CF2H H NMe CH N 1
197 Et H H H . CF2H H NMe CH N 2
198 Et H H H Ph H NMe CH N 0
199 Et H H H Ph H NMe CH N 2
200 Et H H H 2-fluoro- H NMe CH N 0 phenyl
[ 0406]
[ Table 44]
Figure imgf000416_0001
221 Et H H H COCF3 H NMe CH N 0
222 Et H H H CI H N e CH N 0
223 Et H . H H CI H NMe CH N 1
224 Et H H H CI H NMe CH N 2
225 Et H H H Br H NMe CCHO N 0
[ 0407]
[ Table 45]
Figure imgf000417_0002
[ 0408]
[ Table 46]
Figure imgf000417_0001
Figure imgf000418_0001
[ 0409]
[ Table 47]
Figure imgf000418_0002
294 Et Me H H CF3 H NMe CH N 2
295 Et H Me H CF3 H NMe CH N 0
296 Et H Me H CF3 H NMe CH N 1
297 Et H H H 2-CF3-Ph H NMe CH N 1
298 Et H H H 2-CF3-Ph H NMe CH N 2
299 Et H H H 3-CF3-Ph H NMe CH N 1
300 Et H H H 3-CF3-Ph H NMe CH N 2
[ 0410]
[ Table 48]
Figure imgf000419_0001
324 Et H H H 4-chloro-l- H NMe CH N 2 pyrazolyl
325 Et H H H 3-chloro-l- H N e CH N 0 triazolyl
[ 0411]
[ Table 49]
Figure imgf000420_0001
[ 0412]
[ Table 50]
The R1 R^ RJ R4 Rb Rb A1 A^ AJ n present
compound
351 Et H H H S02CHzCF3 H NMe CH N 2
352 Et H H H SCH2CH=CH2 H NMe CH N 0
353 Et H H H SCF2CF3 H NMe CH N 0
354 Et H H H SCF2CF2CF3 H NMe CH N 0
355 Et H H H SCF(CF3)2 H NMe CH N 0
356 Et H H H CH(OH) CF3 H NMe CH N 0
357 Et H H H CH (CI) CF3 H NMe CH N 0
358 Et · H H H OH H NMe CH N 0
359 Et H H H OH H NMe CH N 2
360 Et H H H OCF2Br H NMe CH N 2
361 Et H H H OCF3 H NMe CH N 2
362 Et H H H SCF2CF3 H NMe CH N 1
363 Et H H H SCF2CF2CF3 H NMe CH N 1
364 Et H H H SCF2CF2C F3 H NMe CH N 2
365 Et H H H StBu H NMe CH N. 0
366 Et H H H S02tBu H NMe CH N 2
367 Et H CF3 H Br H NMe CH N 0
368 Et H CF3 H Br H NMe CH N 1
369 Et H CF3 H Br H NMe CH N 2
370 Et H H H SCH=C=CH2 H NMe CH N 0
371 Et H H H S02CH=C=CH2 H NMe CH N 2
372 Et H H H S02CH2CH=CH2 H NMe CH N 2
373 Et H I H CF2CF3 H NMe CH N 2
374 Et H NO 2 H CF3 H NMe CH N 0
375 Et H NO 2 H CF3 H NMe CH N 1
[ 0413]
[ Table 51]
Figure imgf000421_0001
392 Et H CF3 H SF5 H NMe CH CH 0
393 Et H CF3 H SF5 H NMe CH CH 1
394 Et H Me H CF2CF3 H NMe CH N 0
395 Et H Me H CF2CF3 H NMe CH N 1
396 Et H Me H CF2CF3 H NMe CH N 2
397 Et H H H I H S CH N 0
398 Et H CF3 H I H S CH N 0
399 Et H H H CF2CF3 H S CH N 0
400 Et H CF3 H CF2CF3 H S CH N 0
[ 0414]
[ Table 52]
Figure imgf000422_0001
[ 0415] [ Table 53]
Figure imgf000423_0002
[ 0416]
[ Table 54]
Figure imgf000423_0001
457 (CH2)3 H H H CF3 H NMe CH N 2 CH3
■ 458, CH2C02 H H H CF3 H NMe CH N . 2
Me
459 CH2CH= H H H CF3 H NMe CH N 2
CC12
460 CH2C≡C H H H CF3 H NMe CH N 2
CH3
461 CH2CN H H H CF3 ' H NMe CH N 2
462 CH2tBu H H H CF3 H NMe CH N 2
463 CH2CH2 H H H CF3 H N e CH N 2
CN
464 CH2Cyc H H H CF3 H NMe CH N 2
Bu
465 CF2Br H H H CF3 H NMe CH N 2
466 Et H CH2F H CF3 H NMe CH ' N 2
467 CH=CH2 H H H CF3 H NMe CH N 0
468 CH=CH2 H H H CF3 H NMe CH N 1
469 CH=CH2 H H H CF3 H NMe CH N 2
470 Et H H H H CF3 S CH N 0
471 Et H H H H CF3 S CH N 2
472 Et H OCF3 H CF2CF3 H NMe CH N 0
473 Et H OCF3 H CF2CF3 H NMe CH N 1
474 Et H OCF3 H CF2CF3 H NMe CH N 2
475 Et H CF3 H CF3 H NMe CH CMe 0
[ 0417]
[ Table 55]
Figure imgf000424_0001
488 Et H OCF3 H SCF3 H NMe CH N. 1
489 Et H OCF3 H SCF3 H NMe CH N 2
490 Et H CF3 H CF3 H NMe CH CBr 1
491 Et H CF3 H CF3 H NMe CH CBr 2
492 Et H H H 2- H NMe CH N 0 pyridyl
493 Et H H H 2- H NMe CH N 2 pyridyl
494 Et H H H 2-furyl H NMe CH N 0
495 Et H H H 2-furyl H NMe CH N 2
496 Et H H H 2- H NMe CH N 0 thienyl
497 Et H H H 2- H NMe CH N 2 thienyl
498 Et H H H CH=CH2 H NMe CH N 0
499 Et H H H CH=CH2 H NMe CH N 2
500 Et H H H COMe H NMe CH N 0
[ 0418]
[ Table 56]
Figure imgf000425_0001
thiazol-5- ylmethyl )
511* Et H H H CF3 H NMe CH N 2
512* Et H CF3 H CF3 H NMe CH N 2
513 Et H H H CF3 H NMe CH COMe 0
514 Et H H H CF3 H NMe CH CSMe 0
515 Et H H H CF3 H NMe CH CS02Me 2
516 Et H H H CF3 H NMe CH CSPh 0
517 Et H H H CF3 H NMe CH CS02Ph 2
518 Et H H H CF3 H NMe CH CS02CH2C 2
F3
519 Et H H H CF3 H NMe CH CCN 0
520 Et H CF3 H CF3 H NMe CNMe N 2
2
521 Et H CF3 H CF3 CO2 NMe CH N 2
H
522 Et H CF3 H CF3 CO NMe CH N 2
NH2
523* Et H CF3 H CF2CF3 H NMe CH N 2
524* Et H CF3 H CF2CF3 H NMe CH N 2
525 Et H CF3 H C02H H NMe CH N 0
[ 0419]
[ Table 57]
Figure imgf000426_0001
CH3)2
544 tBu H CF3 H CF2CF3 H NMe CH N 0
545 tBu H CF3 H CF2CF3 H N e CH N 2
546 CycPen H CF3 H CF2CF3 H NMe CH N 0
547 CycPen H CF3 H CF2CF3 H NMe CH N 2
548 CycHex H CF3 H CF2CF3 H NMe CH N 0
549 CycHex H CF3 H CF2CF3 H NMe CH N 2
550 CH2CF3 H CF3 H CF2CF3 H NMe CH N 0
[ 0420]
[ Table 58]
Figure imgf000427_0002
[ 0421]
In the above [Table 36] to [Table 58] , the symbol "* " in the present compound represents N-oxide. Specifically, the following compounds are mentioned.
The present compound 22
Figure imgf000427_0001
The present compound 36
Figure imgf000428_0001
The present compound 37
Figure imgf000428_0002
The present compound 47
Figure imgf000428_0003
The present compound 48
Figure imgf000428_0004
The present compound 51
Figure imgf000428_0005
The present compound 70
Figure imgf000429_0001
The present compound 511
Figure imgf000429_0002
The present compound 512
Figure imgf000429_0003
The present compound 523
Figure imgf000429_0004
The present compound 524
Figure imgf000429_0005
[ 0422] In the above [ Table 36] to [ Table 58] , "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "iPr" represents an isopropyl group, "Bu" represents a butyl group, "tBu" represents a tert-butyl group, "CycPr" represents a cyclopropyl group, "CycBu" represents a cyclobutyl group, "CycPen" represents a cyclopentyl group, "CycHex" represents a cyclohexyl group, "Ph" represents a phenyl group, "2-CF3-Ph" represents a 2-trifluoromethylphenyl group, "3-CF3-Ph" represents a 3-trifluoromethylphenyl group, "4-CF3-Ph" represents a 4-trifluoromethylphenyl group, "3-CF3- triazolyl" represents a 3-trifluoromethyl- ( lH-1 , 2 , 4- triazol ) -1-yl grorp, "3-CF3-5-Me-triazolyl " represents a 3- trifluoromethyl-5-methyl- ( lH-1 , 2 , 4-triazol ) -1-yl group, and "4-CF3-imidazolyl" represents a 4 -trifluoromethylimidazole- 1-yl group . .■ ■ ■·
[ 0423]
Hereinafter, """H-NMR data of the present compounds listed in [ Table 36] to [ Table 58] are shown.
The present compound 47
XH-NMR (CDC13) δ: 8.53 (lH,dd), 8.07 (lH,s), 7.98 (lH,dd), 7.65 (lH,dd), 7.62-7.56 (2H,m) , 3.90-3.77 (lH,m), 3.75 (3H,s), 3.52-3.42 (lH,m), 1.33 (3H,t).
The present compound 49
1H-NMR (CDCI3) δ: 8.61-7.00 ( 6H, m) , 3.90 (3H,s), 2.94 (2H,q), 1.33 (3H, t) .
The present compound 50
1H-NMR (CDC13) δ: 8.93 (lH,dd), 8.49 (lH,dd), 7.68-7.62 (2H,m), 7.43 (lH,d), 7.25 (lH,d), 3.84 (2H,q), 3.73 (3H,s), 1.31 (3H, q) .
The present compound 52
1H-NMR (CDCI3) δ: 8.48-8.44 (2H,m), 8.05 (lH,d), 7.74 (lH,dd), 7.65 (lH,dd), 7.35 (lH,dd), 3.05 (2H,q), 1.49 (3H, t) .
The present compound 53
1H-NMR (CDCI3) δ: 8.92 (lH,dd), 8.65 (lH,dd), 8.37 (lH,s), 8.11 (lH,d), 7.72 (lH,dd), 7.66 (lH,dd), 4,19 (2H,q), 1.45 (3H,t).
The present compound 54
1H-NMR (CDCI3) δ: 8.66 (lH,s), 8.50 (lH,s), 8.08 (lH,d),
7.90 (lH,s), 7.69 (lH,dd), 3.08 (2H,q), 1.52 (3H,t).
The present compound 55
: H-NMR (CDCI3) δ: 9.15 (lH,d), 8.88 (lH,d), 8.40 (lH,s),
8.14 (lH,d), 7.76 (lH,dd), 4.24 (2H,q), 1.49 (3H,t).
The present compound 56
1H-NMR (CDCI3) δ: 8.95 (lH,dd), 8.49 (lH,dd), 8.00 (lH,s),
7.66 (lH,dd), 6.96 (lH,s), 3.97 (3H,s), 3.84 (2H,q), 3.73
(3H, s) , 1.34 (3H, t) .
The present compound 57
^-NMR (DMSO-De) δ: 8.67 (lH,d), 8.56 (lH,dd), 8.23 (lH,d), 8.05 (lH,d), 7.91 (2H,s), 7.59 (lH,dd), 3.86 (3H,s), 3.00 (2H,q) , 1.21 (3H, t) .
The present compound 58
^- MR (CDC13) δ: 9.20 (lH,d), 9.01 (lH,dd), 8.74 (lH,d), 8.54 (lH,dd), 7.76 (lH,dd), 3.89 (3H,s), 3.86-3.76 (2H,m), 1.37 (3H, t) .
The present compound 59
1H-NMR (CDCI3) δ: 9.18 (lH,d), 8.82 (lH,d), 8.7 (lH,s), 7.92 (lH,s), 4.10 (3H,s), 4.00 (3H,s), 3.02 (2H,q), 1.40 (3H, t) .
The present compound 60
1H-NMR (CDCI3) δ: 9.26 (lH,s), 8.82-8.78 (2H,m) , 8.61 (lH,s), 3.99-3.91 (5H,m), 1.42 (3H,t).
The present compound 61
1H-NMR (CDCI3) δ: 8.50 (lH,dd), 8.22 (lH,d), 7.77 (lH,dd), 7.63 (lH,dd), 7.46 (lH,d), 7.39-7.34 (lH,m), 3.92 (3H,s), 2.95 (2H,q) , 1.34 (3H, t) .
The present compound 62
1H-NMR (CDCI3) δ: 8.79 (lH,d), 8.63 (lH,d), 8.13 (lH,s), 7.66-7.60 (2H,m), 7.49 (lH,d), 4.23 (3H,s), 3.74-3.64 (lH,m), 3.13-3.03 (lH,m), 1.47 (3H,t).
The present compound 63
1H-NMR (CDCI3) δ: 8.95 (lH,dd), 8.50 (lH,dd), 8.12 (lH,d), 7.69-7.61 (2H,m), 7.48 (lH,d), 3.86-3.80 (2H,m) , 3.75 (3H,s) , 1.34 (3H,t) . The present compound 64
1H-NMR (CDC13) δ: '8.91 (lH,dd), 8.46-8.40 (2H,m), 7.91 (lH,d), 7.69-7.61 (2H,m), 3.75-3.68 (5H,m), 1.25 (3H,t) . The present compound 69
1H-NMR (CDCI3) δ: 9.25 (lH,d), 9.20 (lH,d), 8.78 (lH,d), 8.73 (lH,d), 4.02-3.95 (5H,m), 3.94 (3H,s), 1.41 (3H,t) . The present compound 70
1H-NMR (CDCI3) δ: 9.26 (lH,d), 8.86 (lH,d), 8.76 (lH,d), 8.36 (lH,d), 4.34 (3H,s), 4.01 (3H,s), 3.81 (2H,q), 1.40 (3H, t) .
The present compound 76
^-NMR (CDCI3) δ: 8.75 (lH,s), 8.48 (2H,dd), 7.77 (lH,dd), 7.38 (lH,dd)., 3.07 (2H,q), 1.50 (3H,t). (No NH proton was detected)
The present compound 77
1H-NMR (CDCI3) δ: 12.11 . ( 1H, s ) , 8.98 (lH,dd), 8.80. (lH,s), 8.70 (lH,dd), 8.45 (lH,s), 7.70 (lH,dd), 4.30 (2H,q), 1.43 (3H, t) .
The present compound 78
1H-N R (CDCI3) δ: 8.75-8.70 (2H,m), 8.34 (lH,s), 7.96 (lH,d), 3.14-3.07 (2H,m)., 1.48 (3H,t) . (No NH proton was detected)
The present compound 79
1H-NMR (CDCI3) δ: 11.63 (lH,brs), 9.19 (lH,d), 8.93 (lH,d), 8.83 (lH,d), 8.48 (lH,d), 4.35 (2H,q), 1.47 (3H,t). The present compound 80
1H-NMR (CDCI3) δ: 8.75 (lH,dd), 8.62 (lH,dd), 8.46 (lH,.d), 7.81 (lH,dd), 7.45 (lH,dd), 3.07 (2H,q), 1.46 (3H,t).
The present compound 81
1H-NMR (CDCI3) δ: 9.06 (lH,dd), 8.79 (lH,d), 8.58 (lH,dd), 8.43 (lH,d), 7.78 (lH,dd), 3.88 (2H,q), 1.44 (3H,t).
The present compound 82
1H-NMR (CDCI3 ) δ: 8.82 (lH,s), 8.79 (lH,s), 8.50 (lH,s), 7.96 (lH,s), 3.11 (2H,q), 1.50 (3H,t).
The present' compound 83
1H-NMR (CDCI3) δ: 9.29 (lH,s), 8.84 (lH,s), 8.81 (lH,d), 8.47 (lH,d), 3.96 (2H,q), 1.48 (3H,t). '
The present compound 84
■"■H-NMR (CDCI3) δ : 8.59 ( 1H, dd) , 8.24-8.21 ( 1H, m) , 7.81-7.76 (2H,m), 7.69 (lH,dd), 7.42 (lH,dd), 3.06 (2H,q), 1.47
(3H,t).
The present compound 85
1H-NMR (CDCI3) δ: 9.03 (lH,dd), 8.60 (lH,dd), 8.16-8.13 (lH,m), 7.82-7.71 (3H,m), 4.01 (2H,q), 1.43 (3H,t),
The present compound 86
1H-NMR (CDCI3) δ: 8.79 (lH,dd), 8.26 (lH,dd), 7.94 (lH,d), 7.81 (lH,dd), 7.76-7.72 (lH,m), 3.11 (2H,q), 1.50 (3H,t). The present compound 87
""■H-NMR (CDCI3) δ: 9.25 (lH,d), 8.83 (lH,d), 8.18 (lH,s), 7.85-7.76 (2H,m) , 4.08 (2H,q), 1.47 (3H,t). The present compound 89
1H-NMR (CDC13) δ: 9.25 (lH,d), 8.78 (lH,d), 8.43 (lH,s), 3.97-3.87 (5H,m) , 1.41 (3H,t).
The present compound 99
1H-NMR (CDCI3) δ: 9.20 (lH,d), 8.76 (lH,d), 8.26 (lH,s), 4.02 (2H,q), 3.84 (3H,s), 3.04 (6H,s), 1.41 (3H,t).
The present compound 130
1 HNMR (CDCI3) δ: 9.01 (lH,dd), 8.68 (lH.,d), 8.55 (lH,dd),
8.37 (lH,d), 7.74 (lH,dd), 3.87 (3H,s), 3.83 (2H,q), 1.37 (3H, t) .
The present compound 138
1H-NMR (CDCI3) δ: 9.02 (lH,dd), 8.54 (lH,dd), 8.28 (lH,s), 7.95 (lH,s), 7.77 (lH,dd), 4.06 (3H,s), 3.74 (2H,q), 1.35 (3H, t) .
The present compound 144
■""H-NMR (CDCI3) δ: 9.00-8.95 (lH,m), 8.54-8.47 (lH,m), 7.71-
7.64 (2H,m), 6.94 (lH,s)> 4.00 (3H,s), 3.96 (3H,s), 3.81-
3.70 (2H,m), 1.37-1.29 (3H,m).
The present compound 190
XH-NMR (CDCI3) δ: 8.99 '(lH,dd), 8.65 (lH,d), 8.53 (lH,dd),
8.38 (lH,d), 7.71 (lH,dd), 3.83-3.80 (5H,m), 1.35 (3H,t). The present compound 255
1 H-NMR (CDCI3) δ: 8.78 (lH,d), 8.73-8.71 (lH,m), 8.65 (lH,d), 8.31-8.30 (lH,m), 4.35 (3H,s), 3.73-3.63 (lH,m), 3.16-3.06 (lH,m), 1.48 (3H,t) The present compound 386
1 H-NMR ( CDC13 ) δ: 8.95 (lH,d), 8.72-8.71 (lH,m), 8.53 (lH,d), 8.30-8.28 (lH,m), 3.94-3.87 (5H,m), 1.40 (3H,t)
The present compound 505
"""H-NMR (CDC13) δ: 9.05 (lH,dd), 8.79 (lH,t), 8.60 (lH,dd), 8.33 (lH,d), 7.78 (lH,dd), 7.58 (lH,s), 5.66 (2H,s), 3.98 (2H, q) , 1.40 (3H, t) .
The present compound 506
"""H-NMR (CDCI3) δ: 9.30 (lH,d), 8.84 (lH,d), 8.82 (lH,d), 8.36 (lH,d), 7.64 (lH,s), 5.70 (2H,s), 4.09 (2H,q), 1.45 (3H, t) .
The present compound 508
1H-NMR (CDCI3) δ: 9.28 (lH,d), 8.79 (lH,d), 8.48 (lH,s),
3.96 (3H,s), 3.89 (2H,q), 1.42 (3H,t).
The present compound 509
"""H-NMR (CDCI3) δ: 8.75 (lH,d), 8.58 (lH,dd), 8.42 (lH,d),
7.82 (lH,dd), 7.66 (lH,s), 7.44 (lH,dd), 5.96 (2H,s), 2.98
(2H,q) , 1.37 (3H,t) .
The present compound 510
^- R' (CDCI3) δ: 8.80 (2H,dd), 8.46 (lH,d), 7.97 (lH,d),
7.71 (lH,s), 5.99 (2H,s), 3.04 (2H,q), 1.42 (3H,t).
The present compound 511
"""H-NMR (CDCI3) δ: 8.53 (lH,dd), 8.48 (lH,d), 7.98 (lH,dd), 7.93 (lH,d), 7.71 (lH,dd), 4.27 (3H,s), 3.73-3.63 (lH,m), 3.47-3.37 (lH,m), 1.35 (3H,t). The present compound 512
^-NMR (CDC13) δ: 8.75 (lH,d), 8.49 (lH,d), 8.12 (lH,d), 7.94 (lH,d), 4.28 (3H,s), 3.75-3.65 (lH,m), 3.55-3.45 (lH,m) , 1.38 (3H, t) .
The present compound 513
1H-NMR (CDCI3) δ: 8.49 (lH,d), 7.76-7.74 (2H,m), 7.35 (lH,dd), 6.91 (lH,s), 4.05 (3H,s), 3.99 (3H,s), 2.95-2.85 (2H,m) , 1.34-1.24 (3H,m) .
The present compound 514
"""H-NMR (CDCI3) δ: 8.51 (lH,d), 7.97 (lH,s), 7.77 (lH,d), 7.42 (lH,s), 7.37 (lH,dd), 4.18 (3H,s), 2.91 (2H,q), 2.59 (3H,s) , 1.30 (3H,t) .
The present compound 515
■"■H-NMR (CDCI3) δ: 9.08-8.97 (lH,m), 8.58-8.46 (lH,m), 8.41- 8.26 (2H,m), 7.84-7.70 (lH,m), 4.12 (3H,s), 3.72-3.59 (2H,m), 3.33 (3H,s), 1.39-1.22 (3H,m).
The present compound 516
1H-NMR (CDCI3) δ: 8.49 (lH,dd), 8.18 (lH,d), 7.75 (lH,dd), 7.71 (lH,d), 7.50-7.48 (lH,m), 7.36 (lH,dd), 7.30-7.09 (4H,m), 4.02 (3H,s), 2.90 (2H,q), 1.28 (3H,t).
The present compound 517
1H-NMR (CDCI3) δ: 8.97 (lH,dd), 8.49 (lH,dd), 8.31 (lH,d), 8.17 (lH,d), 7.89 (2H,d), 7.72 (lH,dd), 7.69-7.64 (lH,m), 7.61-7.55 (2H,m), 3.87 (3H,s), 3.67 (2H,q), 1.32 (3H,t). The present compound 518 1H-NMR (CDCI3) δ: 9.02-8.97 (lH,m), 8.54-8.49 (lH,m), 8.33 (lH,s), 8.23 (lH,s), 7.80-7.71 (lH,m), 4.03-3.88 (3H,m), 3.75-3.63 (4H,m), 1.36-1.30 (3H,m).
The present compound 519
1H-NMR (CDCI3) δ: 8.55 (lH,dd), 8.37-8.35 (lH,m), 7.93-7.92 (lH,m), 7.81 (lH,dd), 7.43 (lH,dd), 4.19 (3H,s), 2.96 . (2H, q) , 1.33 (3H, t) .
The present compound 520
^H-NMR (CDCI3) δ: 9.22 (lH,t), 8.77 (lH,d), 8.53 (lH,s), 3.95 (2H,q), 3.84 (3H,s), 3.33 (6H,s), 1. 1. (3H, t) .
The present compound 521
XH-NMR (CDCI3) δ: 9.28 (lH,d), 8.80 (lH,d), 8.62 (lH,s), 3.97 (3H,s), 3.89 (2H,q), 1.42 (3H,t). (No active proton was detected)
The present compound 522
1H-NMR (CDCI3) δ: 9.27 (lH,d), 8.79 (lH,d), 8.56 (lH,s), 7.24 (lH,brs), 5.76 (lH,brs), 4.00-3.86 (5H,m), 1.42 (3H,t). The present compound 523
1H-NMR (CDCI3) δ: 9.27 (lH,d), 8.77 (lH,d), 8.45 (lH,s), 7.92 (lHfs), 4.34 (3H,s), 3.81 (2H,q), 1.40 (3H,t). ■
The present compound 524
"""H-NMR (CDCI3) δ: 8.80 (lH,s), 8.46 (lH,s), 8.13 (lH,s), 7.93 (lH,s), 4.27 (3H,s), 3.76-3.66 (lH,m), 3.55-3.45 (lH,m) , 1.38■ (3H, t)
The present compound 525 1H-NMR. (DMSO-D6) δ: 9.06 (lH,d), 8.95 (lH,s), 8.63 (lH,d), 8.31 (lH,s), 3.95 (3H,s), 3.15 (2H,q), 1.23 (3H,t). (No active proton was detected)
The present compound 526
1H-NMR (CDCI3) δ: 8.87 (lH,dd), 8.67 (lH,dd), 8.29 (lH,d), 7.96 (lH,d), 7.72 (lH,dd),. 4.57 (3H,s), 3.73-3.62 (lH,m), 3.17-3.07 (lH,m), 1.48 (3H,t).
The present compound 5-27
1H-NMR (CDC13) δ: 10.95 (lH,s), 8.46-8.42 (2H,m), 7.82 (lH,s), 7.76 (lH,dd), 7.38 (lH,dd), 3.07 (2H,q), 1.50
(3H,t) .
The present compound 528
^-NMR (CDCI3) δ: 9.16 (lH,d), 8.74 (lH,d), 8.70 (lH,d), 8.31 (lH,d), 3.93 (3H,s), 3.88 (2H,q), 3.28 (9H,s), 1.38 (3H,t).
The present compound 529
XH-NMR (CDCI3) δ: 8.51-8.46' (lH,m), 7.94 (lH,s), 7.86 (lH,s), 7.80-7.76 (lH,m), 7.40-7.35 (lH,m), 3.96 (3H,s), 2.96-2.90 (2H,m), 1.31-1.25 (3H,m).
The present compound 530
XH-NMR (GDCI3) δ: 8.99 (lH,dd), 8.54 (lH,dd), 7.97 (lH,s), 7.87 (lH,s), 7.72 (lH,dd), 3.95-3.88 (5H,m),. 1.37 (3H,t). The present compound 531
XH-NMR (CDCI3) .5: 8.93 (lH,dd), 8.45 (lH,dd), 8.19 (lH,s), 7.87 (1H,S) , 7.66 (lH,dd), 3.77-3.75 (3H,m), 3.63 (2H,q), 1.26 (3H, t) .
The present compound 532
1 H-NMR (CDC13) δ: 8.75 (lH,s), 8.72 (lH,s), 8.41 (lH,s), 7.90 (lH,s), 4.15 (3H,s), 2.54 (3H,s)
The present compound 533
1 H-NMR (CDCI3) δ: 9.25 (lH,s), 8.85 (lH,s), 8.75 (lH,s), 8.32 (lH,s), 3.96 (3H,s), 3.73 (3H,s)
The present compound 534
1 H-NMR (CDCI3) δ: 8.74 (lH,s), 8.71 (lH,s), 8.41 (lH,s), 7.93 (lH,s), 4.10 (3H,s), 2.97 (2H,t), 1.82-1.71 (2H,m), 1.08 (3H,t)
The present compound 535
1 H-NMR (CDCI3 ) δ: 9.24 (lH,s), 8.79 (lH,s), 8.74 (lH,s), 8.31 (lH,s), 3.95-3.88 (5H,m), 1.92-1.81 (2H,m) , 1.13 (3H,t)
The present compound 536
1 H-NMR (CDCI3) δ: 8.76 (lH,s), 8.71 (lH,s), 8.41 (lH,s), 8.01 (lH,s), 4.07 (3H,s), 3.64-3.53 (lH,m), 1.38 (6H,d)
The present compound 537
1 H-NMR (CDCI3) δ: 9.24 (lH,s), 8.75 (2H,d), 8.31 (lH,s), 4.71-4.60 (lH,m), 3.93 (3H,s), 1.39 (6H,d)
The present compound 538
1 H-NMR (CDCI3) δ: 8.74 (lH,s), 8.71 (lH,s), 8.41 (lH,s), 7.94 (1H,S) , 4.10 (3H,s) , 2.98 (2H,t), 1.76-1.67 ( 2H, m) , 1.55-1.44 (2H,m), 0.95 (3H,t) The present compound 539
1 H-NMR (CDC13) δ: 9.24 (lH,s), 8.79 (lH,s), 8.74 (lH,s), 8.29 (lH,s), 3.97-3.91 (5H,m), 1.85-1.77 (2H,m) , 1.59-1.48
(2H,m) , 0.99 (3H, t)
The present compound 540
1 H-NMR (CDCI3) δ: 8.76 (lH,s), 8.71 (lH,s), 8.40 (lH,s), 8.00 (lH,s), 4.05 (3H,s), 3.40-3.30 (lH,m), 1.80-1.55
(2H,m), 1.35 (3H,d), 1.02 (3H,t)
The present compound 541
1 H-NMR (CDCI3) δ: 9.23 (lH,s), 8.75 (2H,s), 8.28 (lH,s), 4.54-4,44 (lH,m), 3.92 (3H,s), 2.02-1.91 (lH,m), 1.71-1.57
(lH,m), 1.37 (3H,d), 1.07 (3H,t)
The present compound 542
1 H-NMR (CDCI3) δ: 8.74-8.73 (lH,m), 8.72-8.71 (lH,m), 8.41 (lH,d), 7.92 (lH,d), 4.09 (3H,s), 2.86 (2H,d), 2.03-1.91 (lH,m) , 1.08 (6H,d)
The present compound 543
1 H-NMR (CDCI3) δ: 9.24 (lH,s), 8.81 (lH,s), 8.75 (lH,s), 8.28 (lH,s), 3.93 (3H,s), 3.87 (2H,d), 2.42-2.30 (lH,m), 1.15 (6H,d)
The present compound 544
1 H-NMR (CDC13) δ: 8.98 (lH,dd), 8.71 (lH,d), 8.37 (lH,d), 8.35-8.32 (lH,m), 3.88 (3H,s), 1.26 (9H,s)
The present compound 545
1 H-NMR (CDCI3 ) δ: 9.26 (lH,s), 8.71 (lH,s), 8.66 (lH,s), 8.29 (lH,s), 3.71 (3H,s), 1.41 (9H,s)
The present compound 546
1 H-NMR (CDC13) δ: 8.73 (lH,s), 8.71 (lH,s), 8.41 (lH,s), 8.02 (lH,s), 4.10 (3H,s), 3.72-3.64 (lH,m), 2.27-2.16 (2H,m), 1.85-1.62 (6H,m)
The present compound 547
1 H-NMR (CDCI3) δ: 9.23 (lH,s), 8.76 (lH,s), 8.74 (lH,s), 8.31 (lH,s), 4.88-4.79 (lH,m), 3.90 (3H,s), 2.14-1.83
(6H,m), 1.80-1.69 (2H,m)
The present compound 548
1 H-NMR (CDCI3) δ: 8.76-8.74 (lH,m) , 8.71-8. 0 (lH,m), 8.41- 8.39 (lH,m), 8.01-7.99 (lH,m), 4.05 (3H,s), 3.36-3.27
(lH,m) , 2.07-1.22 (10H,m)
The present compound 549
1 H-NMR (CDCI3 ) δ: 9.23 (lH,s), 8.74 (lH,s), 8.72 (lH,s), 8.28 (lH,s), 4.43-4.34 (lH,m), 3.92 (3H,s), 2.03-1.20
(10H,m)
The present compound 550
1 H-NMR (CDCI3) δ: 8.90 (lH,s), 8.74 (lH,s), 8.40 (lH,s), 8.18 (lH,s), 4.13 (3H,s), 3.68 (2H,q)
The present compound 551
1 H-NMR (CDCI3) δ: 9.30-9.28 ( 1H, m) , .8.87-8.85 (lH,m), 8.78- 8.76 (lH,m), 8.36-8.34 (lH,m), 5.16 (2H,q), 4.04 (3H,s)
The present compound 552
1H-NMR (CDCI3) δ: 8.66 (lH,d), 8.63 (lH,d), 8.36 (lH,d), 7.87 (lH,d), 4.00 (3H,s), 2.95 (2H,q), 1.30 (3H,t).
The present compound 553
1H-NMR (CDC13) δ: 8.55 (lH,dd), 8.35 (lH,s), 7.93 (lH,s), 7.81 (lH,dd), 7.43 (lH,dd), 3.95-3.93 (3H,m), 2.95 (2H,q), 1.32 (3H, t) .
The present compound 554
1H-NMR (CDCI3) δ: 8.72 (2H,d), 8.41 (lH,d), 7.83 (lH,d), 6.98 (2H,d), 6.68 (2H,d), 5.81 (2H,s), 3.71 (3H,s), 2.89 (2H,q) , 1.27 (3H, t) .
The present compound 555
^-NMR (CDCI3) δ: 8.83 (lH,d), 8.71 (lH,s), 7.90 (lH,s), 7.84 (lH,d), 7.05 (2H,d), 6.78 (2H,d), 5.65 (2H,s), 3.75 (3H,s), 2.97 (2H,q), 1.32 (3H,t).
[ 0424]
A compound represented by the formula (M3) :
Figure imgf000443_0001
wherein R1, R2, R3, R4, R5, R6, A1, A2, A3 and n represent any one of the combinations as listed in the followinq [ Table 59] to [ Table 61] . The intermediate compound (M3) represented by the formula (M3) can be synthesized in the same manner as in Production process 2 or Production process 7. [ 0425]
[ Table 59]
Figure imgf000444_0001
[ 0426]
[ Table
Intermediate R R2 RJ R Rb Rb A1 A2 AJ n compound
M3-25 Et H H H CF2CF3 H NMe CH CH 0
M3-26 Et H H H CF2CF3 H NMe CH CH 2
M3-27 Et H CF3 H SCF3 H NMe CH N 0
M3-28 Et H CF3 H SCF3 H NMe CH N 1
M3-29 Et H H H CF3 H NMe CH CH 0
M3-30 Et H H H CF3 H NMe CH CH 1
M3-31 Et H H H CF3 H NMe CH CH 2
M3-32 Et H CF3 H CF3 H NMe CH CH 0
M3-33 Et H CF3 H CF3 H NMe CH CH 1
M3-34 Et H CF3 H CF.3 H NMe CH CH 2
M3-35 Et H CF3 H CF2CF3 H NMe CH CH 0 3-36 Et H CF3 H CF2CF3 H NMe CH CH 1
M3-37 Et H CF3 H CF2CF3 H NMe CH CH 2
M3-38 Et H H H CF3 H S CH N 0
M3-39 Et H CF3 H I H NMe CH N 0
M3-40 Et H CF3 H SCF3 H NMe CH N 2
M3-41 Et H CF3 H I H NMe. CH CH 0 3-42 Et H H H CF3 H NMe CH CBr 0
M3-43 Et H H H CF3 H N(CH2CF3) CH N 0 3-44 Et H CF3 H CF3 H N(CH2CF3) CH N 0 3-45 Et H CF2CF3 H CF3 H NMe CH N 0
M3-46 . Et H CF2CF3 H CF2CF3 H NMe CH N 0
M3-47 Et H H H CF3 H NH CH N 0
M3-48 Et H CF3 H CF3 H NH CH N 0
M3-49 Et H H H CF3 H OH CH N 0
M3-50 Et H CF3 H CF3 H OH CH N 0
[ 0427]
[ Table 61]
Figure imgf000445_0002
[ 0428]
A compound represented by the formula (M6):
Figure imgf000445_0001
wherein V2, R2, R3, R4, R5, R6, A1, A2 and A3 represent any one of the combinations as listed in the following [ Table 62] to [ Table 63] . The intermediate compound (M6) represented by the formula (M.6) can be synthesized in the same manner as in Production process 6.
[ 0429]
[ Table 62]
Figure imgf000446_0002
[ 0430]
[ Table 63]
Figure imgf000446_0001
M6-34 F H CF3 H CF2CF3 H N e CH CH
M6-35 CI H CF3 H I H NMe CH N
6-36 F H CF3 H I H NMe CH N
M6-37 CI H CF3 H SH H NMe CH N
M6-38 F H CF3 H SH H NMe CH N
M6-39 CI H CF3 H SCF3 H NMe CH N
M6-40 F H CF3 H SCF3 H NMe CH N
M6-41 CI H CF3 H I H NMe CH CH
M6-42 F H CF3 H I H NMe CH CH
M6-43 CI H H H CF3 H NMe CH CBr
M6-44 CI H H H CF3 OCH3 NMe CH CH
Μβ-45 CI H H H SCF3 H . NMe CH CH
Μβ-46 CI H H H CF3 H S CH CH
[ 0431]
A compound represented by the formula (M20):
Figure imgf000447_0001
5, R6, A1, A2 and A3 represent any one of the combinations as listed in the following [ Table 64] to [Table 65] . The intermediate compound (M20) represented by the formula (M20) can be synthesized in the same manner as in Production process 6.
[ 0432]
[ Table 64]
Intermediate V R R R4 R5 Rb A1 A2 AJ compound 2
M20-1 CI H H H CF3 H NMe CH N
M20-2 F H H H CF3 H NMe CH N
M20-3 CI H CF3 H CF3 H NMe CH N
M20-4 F H CF3 H CF3 H NMe CH N
M20-5 CI H H H CF2CF3 H NMe CH N
M20-6 F H H H CF2CF3 H NMe CH N
M20-7 CI H H H I H NMe CH N M20-8 F H H H I H NMe CH N
M20-9 CI H CF3 H CF3 H S CH N 20-10 F H CF3 H CF3 H S CH N
M20-11 CI H H H CF3 H S CH N 20-12 F H H H CF3 H S CH N
M20-13 CI H H H SCF3 H NMe CH N
M20-14 F H H H SCF3 H NMe CH N
M20-15 CI H H H S02CF3 H NMe CH N 20-16 F H H H S02CF3 H NMe CH N 20-17 CI H CF3 H CF2CF3 H NMe CH N
M20-18 F H CF3 H CF2CF3 H NMe CH N
M20-19 CI H H H SOCF3 H NMe CH N
M20-20 F H H H SOCF3 H NMe CH N
M20-21 CI H H H I H NMe CH CH
M20-22 F H H H I H NMe CH CH
M20-23 CI H H H SF5 H NMe CH CH
M20-24 F H H H SF5 H NMe CH CH
[ 0433]
[ Table 65]
Figure imgf000448_0001
[ 0434] A com ound represented by the formula (Ρ9') :
Figure imgf000449_0001
wherein R1, R2, R3, R4, R6, A1, A2, A3 and n represent any one of the combinations as listed in the following [ Table 66] . The intermediate compound (Ρ9') represented by the formula (P91) can be synthesized in the same manner as in
Production process
[ 0435]
[ Table 66]
Figure imgf000449_0003
[ 0436]
A compound represented by the formula (M2)
Figure imgf000449_0002
wherein R1, R2, R3, R4 and n represent any one of the combinations as listed in the following [ Table 67] . The intermediate compound (M2) represented by the formula (M2) can be synthesized in the same manner as in Production process 12 or Production process 14.
[ 0437]
[ Table 67]
Figure imgf000450_0002
[ 0438]
A compound represented by the formula (M18) :
Figure imgf000450_0001
wherein R1, R2, R3, R4 and n represent any one of the combinations as listed in the following [ Table 68] . The intermediate compound (M18) represented by the formula (M18) can be synthesized in the same manner as in Production process 13.
[ 0439]
[ Table 68]
Intermediate R RJ R4 n
compound
M18-1 Et H H H 0
M18-2 Et H H H 1
M18-3 Et H H H 2
Ml8-4 Et H CF3 H 0
M18-5 Et H CF3 H 1
M18-6 Et H CF3 H 2 [ 0440]
A compound represented by the formula (M37) :
Figure imgf000451_0001
wherein R1, R2, R3, R4 and n represent any one of. the combinations as listed in the following [ Table 69] . The intermediate compound (M37) represented by the formula (M37) can be synthesized in the same manner as in Production process 14.
[ 0441]
[ Table 69]
Figure imgf000451_0002
[ 0442]
NMR data of the intermediate compounds 3-33, M3-47, 3-48, 3-49, M3-50, M3-51, M3-52, M3-53, M3-54, M3-55, M3- 56, 6-1, M6-17, M6-44, M6-45, M6-46, M2-1, M2-4, M18-1, M20-44, 37-1 and M37-4 are shown in the following [ Table 70] to [ Table 71] .
[ 0443] [ Table 70]
Figure imgf000452_0001
[ 0444]
[ Table 71]
Intermediate
compound Material value
IH-NMR (CDC13) δ: 8.76 (lH,d), 8.71 (lH,dd), 8.39
M6-1 (lH,d), 7.97 (lH,dd), 7.48 (lH,dd), 3.97 (3H,s).
iH-NMR (CDCI3) δ: 8.97-8.95 (lH,m), 8.74-8.72 (lH,m) ,8.41-8.39 (lH,m), 8.23-8.21 (lH,m), 4.03
M6-17 (3H,s) 1H-NMR (CDC13) δ: 8.65 (lH,dd), 8.09 (lH,s), 7.91 (lH,dd), 7.40 (lH,dd), 6.94 (lH,s), 3.98 (3H,s),
Μβ-44 3.81 (3H, s) .
1H-NMR (CDC13) δ: 8.69 (lH,d), 8.21 (lH,s), 7.94 6-45 ; (lH,d), 7.65 (lH,d), 7.53-7.41 (2H,m), 3.85 (3H,s).
1H-NMR (CDC13 ) δ : 8.65 (lH,dd), 8.47 (lH,s), 8.08
M6-46 (lH,d), 7.93 (lH,dd), 7.68 (lH,d), 7.38 (lH,dd).
1H-N R (CDC13) δ :. 8.31 (lH,d), 7.75 (lH,d), 7.49 2-1 (lH,dd), 2.97 (2H,q), 1.44 (3H,t).
1H-NMR (CDC13) δ: 8.55 (lH,s), 7.92 (lH,s), 3.02
M2-4 (2H,q), 1.47 (3H,t).
1H-N R (CDC13) δ : 8.56 (lH,d), 7.74 (lH,d), 7.47
M18-1 (lH,dd), 2.99 (2H,q), 1.42 (3H,t).
1H-N R (CDC13). 5: 9.53 (lH,brs), 8.54 (lH,d), 7.90 (lH,d), 7.70-7.46 (3H,m), 6.76 (lH,d), 4.48
M20-44 (lH,brs) , 2.91 (3H,d) .
1H-NMR (CDC13) δ: 8.49 (lH,dd), 7.75 (lH,dd), 7.43
M37-1 (lH,dd), 3.06 (2H,q), 1.38 (3H,t).
1H-NMR (CDC13) δ: 8.68 (lH,s), 7.88 (1H,S), 3.13
M37-4 (2H,q), 1.44 (3H,t).
[ 0445]
Next, Formulation Examples will be described. Herein, the term "part(s)" means "part(s) by weight".
[ 0446]
Formulation Example 1
Any one of the present compounds 1 to 555 (10 parts) is dissolved in a mixture of xylene (35 parts) and N,N- dimethylformamide (35 parts), and to the mixture is added polyoxyethylene styryl phenyl ether (14 parts) and calcium dodecylbenzenesulfonate (6 parts), and stirred to give an emulsifiable concentrate of each compound.
[ 0447]
Formulation Example 2
Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), a fine powder (20 parts) of synthetic hydrated silicone oxide and diatomite (54 parts) are mixed, then to the mixture is added any one of the present compounds 1 to 555 (20 parts), and mixed to give a wettable powder of each compound.
[ 0448]
Formulation Example 3
To any one of the present compounds 1 to 555 (2 parts) is added a fine powder (1 part) of synthetic hydrated silicone oxide, calcium lignin sulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts), and mixed Then, to the mixture is added an appropriate amount of water, further stirred, granulated with a granulator, and draft-dried to give granules of each compound.
[ 0449]
Formulation Example 4
Any one of the present compounds 1 to 555 (1 part) is dissolved in an appropriate amount of acetone. To the mixture is added a fine powder (5 parts) of synthetic hydrated silicone oxide, PAP (0.3 parts), and Fubasami clay (93.7 parts), and well stirred. Then, acetone is removed by evaporation to give dusts of each compound.
[ 0450]
Formulation Example 5
A mixture " (weight ratio = 1:1) of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (35 parts), any one of the present compounds 1 to 555 (10 parts), and water (55 parts) are mixed, pulverized by a wet grinding method to give a suspension concentrate of each compound.
[ 0451]
Formulation Example 6
Any one of the present compounds 1 to 555 (0.1 parts) is dissolved in xylene (5 parts) and trichloroethane (5 parts), and mixed with deodorized kerosine (89.9 parts) to give an oil solutions of each compound.
[ 0452]
Formulation Example 7
Any one of the present compounds 1 to 555 (10 mg) is dissolved in acetone (0.5 ml). The mixture is added to animal powdered solid feed (powdered solid feed for breeding, CE-2, from CLEA Japan, Inc.) (5 g) and mixed uniformly. Then, acetone is removed by evaporation to give a poison bait of each compound.
[ 0453]
Formulation Example 8
Any one of the present compounds 1 to 555 (0.1 parts), and Neothiosol (Chuo Kasei Co. Ltd.) (49.9 parts) are charged into an aerosol container. After an aerosol valve is attached to the container, dimethyl ether (25 parts) and LPG (25 parts) are charged into the container. The container is vibrated, and attaching an actuator to give an oily aerosol of each compound.
[ 0454]
Formulation Example 9
Any one of the present compounds 1 to 555 (0.6 parts), BHT (2, 6-di-tert-butyl-4-methylphenol) (0.01 parts), xylene (5 parts), deodorized kerosine (3.39 parts), and an emulsifier (Atmos 300, registered trade name for Atmos Chemical Ltd.) (1 part) are mixed and dissolved. The mixture and distilled water (50 parts) are charged into an aerosol container, and attaching a valve. Then, propellant (LPG) (40 parts) is pressure-charged into the container through the valve to give an aqueous aerosol of each compound.
[ 0455]'
^Formulation Example 10
Any one of the present compounds 1 to 555 (0.1. g) is dissolved in propylene glycol (2 ml), and the solution is impregnated into a porous ceramic plate (4.0 x 4.0 cm, 1.2 cm thick) to give a heat-type smoking agent.
[ 0456]
Formulation Example 11
Any one of the present compounds 1 to 555 (5 parts) and ethylene-methyl methacrylate copolymer (proportion of methyl methacrylate in the copolymer: 10 wt %, Acryft WD301, manufactured by Sumitomo Chemical Co., Ltd) (95 parts) are melt-mixed by a sealed, pressurized kneader (manufactured by Moriyama Co., Ltd.). The resulting mixture is extruded from a molding machine via a molding die to give a rod- shaped molded article (15 cm long, 3 mm diameter) .
[ 0457]
Formulation Example 12
Any one of the present compounds 1 to 555 (5 parts) and soft vinyl chloride resin (95 parts) are melt-mixed by a sealed, pressurized kneader (manufactured by Moriyama Co., Ltd.) . The resulting mixture is extruded from a molding machine via a molding die to give a rod-shaped molded article (15 cm long, 3 mm diameter) .
[ 0458] '
Formulation Example 13
Any one of the present compounds 1 to 555 (100 mg) , lactose (68.75 mg) , corn starch (237.5 mg) , macrocrystalline cellulose (43.75 mg) , polyvinyl pyrrolidone (18.75 mg) , sodium carboxymethyl starch (28.75 mg) , and magnesium stearate (2.5 mg) are mixed, and the resulting mixture is compressed to a suitable size to give tablets.
[ 0459]
Formulation Example 14 Any one of the present compounds 1 to 555 (25 mg) , lactose (60 mg) , corn starch (25 mg) , carmellose calcium (6 mg) , and 5% hydroxypropylmethyl cellulose (appropriate amount) are mixed, and the resulting mixture is packed into hard shell gelatin capsules or hydroxypropyl methylcellulose capsules to give capsules.
[ 0460]
Formulation Example 15
To a mixture of any one of the present compounds 1 to 555 (1000 mg) , fumaric acid (500 mg) , sodium chloride (2000 mg) , methylparaben (150 mg) , ■ propylparaben (50 mg) , granulated sugar (25000 mg) , 70% solution of sorbitol (13000 mg) , VeegumK (VanderbiltCo ) (100 mg) , a perfume (35 mg) , and a colorant (500 mg) is added distillated water such that the final volume becomes 100 ml, and well mixed to give a suspension for oral administration.
[ 0461]
Formulation Example 16
Any one of the present compounds 1 to 555 (5 % by weight) is dissolved in Polysorbate 85 (5 % by weight), benzyl alcohol (3 % by weight), and propylene glycol (30 % by weight) , and a phosphate buffer is added thereto such that the pH becomes 6.0-6.5, and water is added thereto to be a final volume to give a liquid for oral administration.
[ 0462] Formulation Example 17
Aluminum distearate (5 % by weight) is dispersed into a fractionated coconut oil (57 % by weight) and Polysorbate 85 (3 % by weight) by heating. After cooling to room temperature, saccharine (25 % by weight) is dispersed into the oily vehicle. Then, the present compounds 1 to 555 (10 % by weight) is added to the mixture to give a paste for oral administration.
[ 0463]
Formulation Example 18
Any one of the present compounds 1' to 555 (5 % by weight) and a limestone powder (95 % by weight) are mixed, and then the mixture is subjected to a wet granulation method to give granuls for oral administration.
[ 0464]
Formulation Example 19
Any one of the present compounds 1 to 555 (5 parts) is dissolved in diethylene glycol monoethyl ether (80 parts), and then propylene carbonate (15 parts) is mixed therewith to give a spot-on liquid.
[ 0465]
Formulation Example 20
Any one of the present compounds 1 to 555 (10 parts) is dissolved in diethylene glycol monoethyl ether (70 parts), and then 2-octyldodecanol (20 parts) is mixed therewith to give a pour-on liquid.
[ 0466]
Formulation Example 21
To any one of the present compounds 1 to 555 (0.5 parts) are added Nikkol TEALS-42 (Nikko Chemicals Co., Ltd., 42% aqueous solution of triethanolamine lauryl sulfate) (60 parts) and propylene, glycol (20 parts). After stirring and mixing enough to form a homogeneous solution, water (19.5 parts) is added thereto and the mixture is stirred and mixed adequately to give a homogeneous shampoo formulation.
[ 0467]
Formulation Example 22
Any one of the present compounds 1 to 555 (0.15 % by weight), an animal feed (95 % by weight), and a mixture (4.85 % by weight) of dicalcium phosphate, diatomite, Aerosil, and carbonate (or chalk) are stirred and mixed adequately to give a premix for animal feed.
[ 0468]
Formulation Example 23
Any one of the present compounds 1 to 555 (7.2 g) and
Vosco S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) (92.8 g) are dissolved and mixed at 100°C. Then, the mixture is poured into a suppository mold, and cooled and solidified to give a suppository.
[ 0469] The controlling effect on pests by the present compound will be demonstrated below with reference to Test Examples .
[ 0470]
Test Example 1
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-9,12-16, 18-20, 22-28, 30-32, 36-37, 40, 44, 46-48, 50-51, 56, 60, 62-65, 69-70, 72, 74, 76, 79-81, 84-85, 89, 99, 138, 144, 190, 508, 511-515, 517-524, 526. and 528-529 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, on a cucumber seedling (the first true leaf stage) planted in a plastic cup was inoculated with about 30 Aphis gossypii (whole stage) , and leaving it for a day. Twenty (20) ml of each test solution was sprayed on the seedling.
Six (6) days after spraying, the number of the surviving Aphis gossypii parasitized on the leaves of the cucumber was examined, and a control value was calculated according to the following equation:
Controlling value (%)={ 1- (Cb x Tai)/(Cai x Tb)} x 100 wherein the symbols represent as follows:
Cb: the number of insects in a non-treated section before treatment Cai : the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai : the number of insects in a treated section on observation
wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound as in Formulation Example 5 with the same amount of water as in the treated- section was used.
As a result, in the treated-section using each test solution containing each of the present compounds 1-9, 12- 16, 18-20, 22-28, 30-32, 36-37, 40, 44, 46-48, 50-51, 56, 60, 62-65, 69-70, 72, 74, 76, 79-81, 84-85, 89, 99, 138, 144, 190, 508, 511-515, 517-524, 526 and 528-529, the control value was 90% or more. .
[ 0471]
Test Example 2
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-3, 5- 8, 13-16, 19-20, 25,. 27, 30, 32, 36-37, 44, 47-48, 50-51, 60, 62-64, 72, 81, 85,. 99, 138, 144, 511-512, 515, 518, 522-524 and 528 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, a cucumber seedling (the second true leaf stage) planted in a plastic cup was drenched at its foot with 5 ml of each of the diluted solutions, and kept in a greenhouse of 25°C for 7 days. On the cucumber leaf surface was inoculated with about 30 Aphis gossypii (whole stage) , and further kept in the greenhouse for 6 days, then the number of insect of living Aphis gossypii parasitized on the leaves of the cucumber was examined., and a control value was calculated according to the following eguation:
Controlling value (%)={ 1- ( Cb x Tai)/(Cai x Tb)} x 100 wherein the symbols represent as follows:
Cb : the number of insects in a non-treated section before treatment
Cai : the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai : the number of insects in a treated section on observation
wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound as in Formulation Example 5 with the same amount of water as in the. treated- section was used.
As a result, in the treated-section using each test solution containing each of the present compounds 1-3, 5-8, 13-16', 19-20, 25, 27, 30, 32, 36-37, 44, 47-48, 50-51, 60, 62-64, 72, 81, 85, 99, .138, 144, 511-512, 515, 518, 522-524 and 528, the control value was 90% or more.
[ 0472]
Test Example 3
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-3, 5- 9, 12-20, 22, 24-30, 32, 36-37, 44, 50, 60, 62-64, 72, 74, 81, 84-85, 89, 99, 138, 144, 511, 515, 518-519, 521, 523- 524. and 529 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, a rice seedling (the second leaf stage) planted in a polyethylene cup was sprayed with 10 ml of each test solution. After air-drying, 20 third-fourth instar larvae of Nilaparvata lugens were released, and kept in the greenhouse of 25°C. After 6 days, the number of insect of living Nilaparvata lugens parasitized on the rice was examined, and a control value was calculated according to the following eguation:
Controlling value (%)={ 1- (Cb x Tai)/(Cai x Tb)} x 100 wherein the symbols represent as follows: Cb: the number of insects in a non-treated section before treatment
Cai : the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai: the number of insects in a treated section on observation
wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound as in Formulation Example 5 with the same amount of water as in the treated- section was used.
As a result, in the treated-section using each test solution containing each of the present compounds 1-3, 5-9, 12-20, 22, 24-30, 32, 36-37, 44, 50, 60, 62-64, 72, 74, 81, 84-85, 89, 99, 138, 144, 511, 515, 518-519, 521, 523-524 and 529, the control value was 90% or more.
[ 0473]
Test Example 4
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-3, 5- 6, 8, 12-16, 18-19, 22, 24-27, 29, 32, 36-37, 44., 48, 50, 60, 62-64, 72, 74, 81, 85, 89, 99, 138, 144, 508, 512, 515, 518-519 and 521-524 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
Gn the other hand, a rice seedling (2 weeks after sowing, the second leaf stage) planted in a plastic cup was drenched at its foot with 5 ml of each test solution, and kept in a greenhouse of 25°C for 7 days. Twenty (20) third- fourth instar larvae of Nilaparvata lugens were released, and further kept in the greenhouse for 6 days, then the number of insect of living Nilaparvata lugens parasitized on the rice was examined, and a control value was calculated according to the following equation:
Controlling value (%)={ 1- ( Cb x Tai)/(Cai x Tb)} x 100 ■ wherein the symbols represent as follows:
Cb: the number of insects in a non-treated section before treatment
Cai : the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai : the number of insects in a treated section on observation
wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound as in Formulation Example 5 with the same amount of water as in the treated- section was used.
As a result, in the treated-section using each test solution containing each of the present compounds 1-3, 5-6, 8, 12-16, 18-19, 22, 24-27, 29., 32, 36-37, 44, 48, 50, 60, 62-64, 72, 74, 81, 85, 89, 99, 138, 144, 508, 512, 515, 518-519 and 521-524, the control value was 90% or more.
[ 0474]
Test Example 5
Each test solution was prepared by diluting a formulation containing any of the present compounds 3, 5-6, 8, 13-16, 18-20, 24-27, 29, 36-37, 44, 47, 60, 63-64, 72, 74, 89, 99, 511, 515, 518, 521, 523-524 and 528 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, Bemisia tabaci adult was released on a tomato seedling (the third true leaf stage) planted in a polyethylene cup, and made to lay eggs for about 72 hours The tomato seedling was kept in a greenhouse for 8 days. When instar larvae hatched from the eggs, the above test spray solution was sprayed in the amount of 20 ml/cup. The cup was kept in a greenhouse at 25°C. After the keeping for .7 days, the number of. surviving instar larvae on the tomato leaves was examined, and a control value was calculated according to the following equation:
Controlling value (%)={ 1- (Cb x Tai)/(Cai x Tb)} x 100 wherein the symbols represent as follows:
Cb: the number of insects in a non-treated section before treatment
Cai : the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai: the number of. insects in a treated section on observation
wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound as in Formulation Example 5 with the same amount of water as in the treated- section was used.
As a result, in the treated-section using each test solution containing each of the present compounds 3, 5-6, 8, 13-16, 18-20, 24-27, 29, 36-37, 44, 47, 60, 63-64, 72, 74, 89, 99, 511, 515, 518, 521, 523-524 and 528, the control value was 90% or more.
[ 0475]
Test Example 6
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-5, 8- 9, 11-12, 15-16, 19-20, 22-25, 27-33, 35-37, 40, 44, 46-51, 53„ 58-65, 69, 71-74, 76-78, 80-85, 87, 89, 99, 138, 144, 190, 505-506, 508, 511-515, 518, 520-523 and 527-530 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, Cabbage (the third leaf stage) planted in a polyethylene cup was sprayed with 20 mL/cup of each test solution. After the test solution was dried, the aerial part was cut off, and then placed in a 50 mL volume cup. Five (5) second instar larvae of Plutella xylostella were released into the cup, and the cup was sealed with a lid. After the cup was kept at 25°C for 5 days, the number of living' insects was counted. A death rate was calculated according to the following equation:
Death rate (%) = (Number of dead insects/Number of tested insects) x 100
As a result, in the treated-section using each test solution containing each of . the present compounds 1-5, 8-9, 11-12, 15-16, 19-20, 22-25, 27-33, 35-37, 40, 44, 46-51, 53, 58-65, 69, 71-74, 76-78, 80-85, 87, 89, 99, 138, 144, 190, 505-506, 508, 511-515, 518, 520-523 and 527-530, the death rate was 80% or more.
[ 0476]
Test Example 7
Each test solution was prepared by diluting a formulation containing any of the present compounds 1-9, 11-20, 22-35, 38-40, 44, 46-48, 50, 53, 58, 60, 62-64, 71- 72, 74, 77-85, 87, 89, 99, 138, 144, 505-506, 508, 511-512, 514-515, 518-520, 523-526 and 528-530 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
On the other hand, an apple tree was planted in a plastic cup, and grown until the seventh-eighth leaf was spread. The apple tree was sprayed with 20 mL/cup of each test solution. After the test solution was dried, 60 first-instar Adoxophyes orana fasciata were released, and the cup was covered with a plastic cup upside-down which the bottom was cut off and a filter paper was put thereon. After 7 days, the number of living insects was counted, and a death rate was calculated according to the following equation:
Death rate (%) = (Number of dead insects/Number of tested insects) x 100
As a result, in the treated-section using each test solution containing each of the present compounds 1-9, 11- 20, 22-35, 38-40, 44, 46-48, 50, 53, 58, 60, 62-64, 71-72, 74, 77-85, 87, 89,, 99, 138, 144, 505-506, 508, 511-512, 514-515, 518-520, 523-526 and 528-530, the death rate was 90% or more.
[ 0477]
Test Example 8
Each test solution was prepared by diluting a formulation containing any of the present compounds 1, 3-5, 8, 15-16, 19-20, 23, 27, 29, 37, 40, 44, 48, 60-61, 64, 72, 74, 518, 523 and 528 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.- A filter paper having a diameter of 5.5 cm was spread on the . bottom of a polyethylene cup having a . diameter of 5.5 cm and each test solution (0.7 ml) was added dropwise onto the filter paper. As a bait sucrose (30 mg) was uniformly placed on the filter paper. Into the polyethylene cup, 10 female imagoes of Musca do estica were released and the cup was sealed with a lid. After 24 hours, the number of surviving Musca domestica was examined and the death rate of the pest was calculated.
As a result, in the treatment .with each test solution containing each of the present compounds 1, 3-5, 8, 15-16, 19-20, 23, 27, 29, 37, 40, 44, 48, 60-61, 64, 72, 74, 518, 523 and 528, the death rate was 100%.
[ 0478]
Test Example 9 - Each test solution was prepared by diluting a formulation containing any of the present compounds 4-5, 19-20, 28-29, 40, 44, 48, 60, 71-74, 89, 523 and 528 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
A filter paper having a diameter of 5.5 cm was spread on the bottom of a polyethylene cup having a diameter of 5.5 cm and each test solution (0.7 ml) was added dropwise onto the filter paper. As a bait sucrose (30 mg) was uniformly placed on the filter paper. Into the polyethylene cup, 2 male imagoes of Blattalla germanica were released and the cup was sealed with a lid. After 6 days, the number of surviving Blattalla germanica was examined and the death rate of the pest was calculated.
As a result, in the treatment with each test solution containing each of the present compounds 4-5, 19-20, 28-29, 40, 44, 48, 60, 71-74, 89, 523 and 528, the death rate was 100%.
[ 0479]
Test Example 10
Each test solution was prepared by diluting a formulation containing any of the present compounds 1, 3-5, 8, 15-16, 19-20, 22-25, 27-28, 31-33, 35, 37, 40, 44, 48-49, 51, 59-64, 71-74, 80-81, 84-85, 89, 99, 138, 144, 505-506, 508, 514-515, 518, 520, 522-523 and 528 as obtained in Formulation Example 5, with water so as to give 500 ppm of the concentration of the active ingredient.
To ion-exchanged water (100 mL) , each test solution (0.7 ml) was added (active ingredient concentration: 3.5 ppm) . Into the solution, 20 last-instar larvae of Culex pipiens pallens were released. One day after, the number of surviving Culex pipiens pallens was examined and the death rate of the pest was calculated..
As a result, in the treatment with each test solution containing each of the present compounds 1, 3-5, 8, 15-16, 19-20, 22-25, 27-28, 31-33, 35, 37, 40, 44, 48-49, 51, 59- 64, 71-74, 80-81, 84-85, 89, 99, 138, 144, 505-506, 508, 514-515, 518, 520, 522-523 and 528, the death rate was 95% or more .
[ 0480]
Test Example 11
Each 2 mg of the present compounds 1, 5, 8, 15-16, 19, 23, 25-27, 30, 37, 40, 49, 61, 63, 99 and 516 was put into a screw tube (Maruemu No. 5; 27 x 55 mm) . Acetone (0.2 ml) was added thereto and sealed with a cap. After dissolving the compound in acetone, the screw tube was rotated and inverted to uniformity coat the solution onto the whole inner wall of the tube. After removing the cap, the solution was air-dried for about 2 hours. Then, non- blood-sucking nymphal ticks, Haemaphysalis longicornis (5 ticks/group) were released into the tube, and the tube was sealed with the cap. After 2 days, the number of dead tick was counted, and a death rate was calculated according to the following equation: Death rate (%) = (Number of dead tick /Number of tested tick) x 100
As a result, in the treatment with each test solution containing each of the present compounds 1, 5, 8, 15-16, 19, 23, 25-27, 30, 37, 40, 49, 61, 63, 99 and 516, the death rate was 100%.
Industrial Applicability
[ 0481]
The present compound has a controlling effect on pests and is useful as an active ingredient of a pest control agent .

Claims

1. A compound represented by the formula (1):
Figure imgf000475_0001
wherein
A1 represents -NR7-, an oxygen atom or a sulfur atom,
A2 represents a nitrogen atom or =CR8-,
A3, represents a nitrogen atom or =CR9-,
R1 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y,
R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -S (0 ) 2NR10R1:L, - NR10Rn, -NR^CC^R11, -NR10C (0 ) R11 , -C02R10, -C(0)R10, C (0 ) NR10R11, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 and R6 are the same or different and each represents a , C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -S (0 ) 2NR10RU, - NR^R11, -NR10CO2RU, -NR10C (0 ) R11, -C02R10, -C(0)R10, C(O)NR10R11, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom (wherein R5 and R6 do not represents a hydrogen atom at the same time) ,
R7 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z ) ,. -CO2R10, -C(0)R10, a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y or a hydrogen atom,
R8 and R9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, -NR^R11, -C02R10, - C(0)R10, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R10 and R11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom,
each m independently represents 0, 1 or 2, and
n represents 0, 1 or 2,
wherein the -S(0)mR10, R10 does not a hydrogen atom when m is 1 or 2,
Group X: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more Cl- C3 alkyl groups, a cyano group, a hydroxy group and a halogen atom,
Group Y: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms and a halogen atom,
Group Z: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group optionally substituted by one or more halogen atoms, a halogen atom, a cyano group and a nitro group,
Group : the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2- C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, hydroxy group, a halogen atom and a cyano group,
or an N-oxide thereof.
2. The compound according to claim 1, wherein
A1 is -NR7-, an oxygen atom. or a sulfur atom,
A2 is a nitrogen atom or =CR8-,
A3 is . a nitrogen atom or =CR9-,
R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, -OR10, -S(0)mR10, -SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, -OR10, S(0)mR10, -SF5, a halogen atom or a hydrogen atom,
R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), or a hydrogen atom,
R8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom, and R9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
3. The compound according to claim 1, wherein
A1 is -NR7-, an oxygen atom or a sulfur atom,
A2 is a nitrogen atom or =CR8-,
A3 is a nitrogen atom or =CR9-,
R1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl group) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2 and R4 are the same or different each other and each represents a halogen atom or a hydrogen atom,
R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C.1-C3 alkyl . group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted; by one or more halogen atoms), -OR10, -S(0)mR10, a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5 is a C1-C6 alkyl group, optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, -SF5 or a halogen atom, R6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom,
R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms,
R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms, R is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom, and
R9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR10, -S(0)mR10, a halogen atom or a hydrogen atom.
4. The compound according to any one of claims 1 to 3, wherein A1 is -NR7- .
5. The compound according to any one of claims 1 to 3, wherein A1 is an oxygen atom.
6. The compound according to any one of claims 1 to 3, wherein A1 is a sulfur atom.
7. The compound according to any one of claims 1 to 6, wherein A2 is =CR8- .
8. The compound according to any one of claims 1 to 6, wherein A2 is =CR8-, and A3 is a nitrogen atom.
9. The compound according to any one of claims 1 to 6, wherein A2 is =CR8-, A3 is =CR9- .
10. A compound represented by the formula (1-1) :
Figure imgf000484_0001
wherein
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A represents a nitrogen atom or =CR
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and Ra are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , -SF5 or a halogen atom,
R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms),
R9a represents a C1-C6 alkyl group optionally substituted ■ by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein. R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
11. The compound according to claim 10, wherein
Ala is -NR7a-,. an oxygen atom or a sulfur atom,
A is a nitrogen atom or =CR -,
Rla is a C2-C6 alkyl group, a C1-C6 haloalkyl group . or C4- C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups),
R2a and R4a both are a hydrogen atom,
R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom,
R5a is a C1-C6 haloalkyl group, -OR22a (wherein R22a is a Cl- C6 haloalkyl group), -S(0)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), -SF5 or a halogen atom, and
R7a is a CI-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1.-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) .
12. The compound according to claim 10 or 11, wherein Ala is -NR7a- .
13. The compound according to claim 10 or 11, wherein. Ala is an oxygen atom.
14. The compound according to claim 10 or 11, wherein Ala is a sulfur atom.
15. A compound represented by the formula (1-2)
Figure imgf000489_0001
wherein
A3b represents a nitrogen atom or =CR9b- (wherein R9 represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group,
R7b represents methyl group or a propargyl group,
R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one" or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom,
n represents 0, 1 or 2,
or an N-oxide thereof.
16. A compound represented by the formula (1-3)
Figure imgf000490_0001
wherein
A 3b represents a nitrogen atom or =CR - (wherein R 9b represents a hydrogen atom or a halogen atom) , .
Rlb represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21 (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
R5b represents a C1-C6 haloalkyl group, -OR22b (wherein R22b represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom,
n represents 0, 1 or 2,
or an N-oxide thereof.
17. A compound represented by the formula (1-4)
(1-4)
Figure imgf000490_0002
wherein
A3 represents a nitrogen atom or =CR3D- (wherein RSD represents a hydrogen atom or a halogen atom) ,
Rlb represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2) , a halogen . atom or a hydrogen atom,
R5b represents, a C1-C6 haloalkyl group, -OR22b (wherein R22 represents a C1-C6 haloalkyl group), -S(0)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), -SF5 or a halogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
18. A compound represented by the formula (1-5)
Figure imgf000491_0001
wherein
R70a represents hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms,
A3a represents a nitrogen atom or =CR9a-,
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms, or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the . cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or . more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents. 0, 1 or 2), -SF5 or a halogen atom, R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms ) , -S(0)mR2 a. (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
19. A pest control composition comprising a compound according to any one of claims 1 to 18 and an inert carrier
20. A method for controlling a pest, which comprises applying an effective amount of the compound according to any one of claims 1 to 18 to the pest or a habitat of the pest .
21. A compound represented by the formula (M3-1) :
Figure imgf000494_0001
wherein
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A represents a nitrogen atom or =CR -,
Rla represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups) , a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , -SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally. substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) ,
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S (0 ) mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and
n represents 0, 1 or 2,
or an N-oxide thereof.
22. A compound represented by the formula (M6.-1) :
Figure imgf000496_0001
wherein
V2 represents a halogen atom,
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or =CR9a-,
Ra and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , a cyano group, a nitro group, a halogen atom or a hydrogen atom,
R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2 ) , -SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR2 a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
or an N-oxide thereof.
23. A compound represented by the formula (M20-1):
Figure imgf000498_0001
wherein
V2 represents a halogen atom,
Ala represents -NR7a-, an oxygen atom or a sulfur atom, A represents a nitrogen atom or =CR a-,
R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom,
R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2- C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a Cl- C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), -OR20 (wherein R20 represents a C1-C.6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR (wherein R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), -SF5 or a halogen atom, R represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3- C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and
R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, -OR2 a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), -S(0)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom,
or an N-oxide thereof.
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Cited By (179)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013191113A1 (en) * 2012-06-18 2013-12-27 住友化学株式会社 Fused heterocyclic compound
WO2014104407A1 (en) * 2012-12-27 2014-07-03 Sumitomo Chemical Company, Limited Fused oxazole compounds and use thereof for pest control
WO2014119679A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest-control method
WO2014119494A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest control composition and method for controlling pest
WO2014119699A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest-control composition and pest-control method
WO2014125651A1 (en) * 2013-02-13 2014-08-21 Sumitomo Chemical Company, Limited Pest controlling composition and use thereof
WO2014132972A1 (en) * 2013-02-28 2014-09-04 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
WO2014132971A1 (en) * 2013-02-28 2014-09-04 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
WO2014142292A1 (en) 2013-03-15 2014-09-18 日本農薬株式会社 Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide
WO2014148451A1 (en) * 2013-03-19 2014-09-25 日本農薬株式会社 Fused heterocyclic compound or salt thereof, pesticide for agricultural and horticultural use containing said compound, and usage method therefor
WO2014157600A1 (en) * 2013-03-29 2014-10-02 日本農薬株式会社 Condensed heterocyclic compound or salts thereof, agricultural and horticultural pesticide containing said compound, and method for using same
WO2015000715A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
WO2015002211A1 (en) 2013-07-01 2015-01-08 住友化学株式会社 Fused heterocyclic compound and pest control use thereof
WO2014149207A3 (en) * 2013-03-15 2015-02-26 Dow Agrosciences Llc Benzimidazole-based insecticidal compositions and related methods
WO2015059039A1 (en) * 2013-10-24 2015-04-30 Syngenta Participations Ag Method of protecting a plant propagation material
EP2873668A1 (en) 2013-11-13 2015-05-20 Syngenta Participations AG. Pesticidally active bicyclic heterocycles with sulphur containing substituents
WO2015072463A1 (en) 2013-11-12 2015-05-21 日本農薬株式会社 Amide compound or salt thereof, agricultural/horticultural insecticide/bactericide containing said compound, and method for using same
WO2015091945A1 (en) 2013-12-20 2015-06-25 Syngenta Participations Ag Pesticidally active substituted 5,5-bicyclic heterocycles with sulphur containing substituents
WO2015121136A1 (en) * 2014-02-17 2015-08-20 Bayer Cropscience Ag 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
CN104968663A (en) * 2013-02-06 2015-10-07 住友化学株式会社 Condensed heterocyclic compound
CN104968659A (en) * 2013-02-06 2015-10-07 住友化学株式会社 Condensed heterocyclic compound
WO2015177063A1 (en) 2014-05-19 2015-11-26 Syngenta Participations Ag Insecticidally active amide derivatives with sulfur-substituted phenyl or pyridine groups
US20150366207A1 (en) * 2013-01-31 2015-12-24 Sumitomo Chemical Company, Limited Composition and method for controlling pests
WO2015198817A1 (en) * 2014-06-26 2015-12-30 Sumitomo Chemical Company, Limited Method for producing fused heterocyclic compound
WO2016005263A1 (en) * 2014-07-08 2016-01-14 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016012395A1 (en) * 2014-07-22 2016-01-28 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016020286A1 (en) * 2014-08-07 2016-02-11 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016023954A2 (en) 2014-08-12 2016-02-18 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016026848A1 (en) * 2014-08-21 2016-02-25 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016030229A1 (en) * 2014-08-25 2016-03-03 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
CN105431433A (en) * 2013-07-02 2016-03-23 先正达参股股份有限公司 Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
WO2016046071A1 (en) * 2014-09-25 2016-03-31 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016087257A1 (en) * 2014-12-01 2016-06-09 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016091731A1 (en) 2014-12-11 2016-06-16 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016096584A1 (en) * 2014-12-17 2016-06-23 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016107742A1 (en) * 2014-12-29 2016-07-07 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016116338A1 (en) * 2015-01-19 2016-07-28 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2016120182A1 (en) 2015-01-30 2016-08-04 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016121997A1 (en) * 2015-01-29 2016-08-04 日本農薬株式会社 Fused heterocyclic compound having cycloalkylpyridyl group or salt thereof, and agricultural or horticultural insecticide containing said compound and use method therefor
WO2016125622A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzoxazole compound, and use thereof for noxious arthropod control
WO2016124563A1 (en) 2015-02-05 2016-08-11 Bayer Cropscience Aktiengesellschsaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
WO2016125621A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzimidazole compound, and use thereof for noxious arthropod control
WO2016124557A1 (en) 2015-02-05 2016-08-11 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
WO2016142327A1 (en) * 2015-03-12 2016-09-15 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016162318A1 (en) 2015-04-08 2016-10-13 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents and intermediate product
KR20160120748A (en) 2014-03-07 2016-10-18 수미토모 케미칼 컴퍼니 리미티드 Fused heterocyclic compound and pest control application thereof
WO2016169882A1 (en) 2015-04-24 2016-10-27 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur substituted five membered ring heterocyles
WO2016169886A1 (en) 2015-04-24 2016-10-27 Syngenta Crop Protection Ag Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocyles
WO2017001311A1 (en) 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2017001314A1 (en) 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
US9549559B2 (en) 2013-01-31 2017-01-24 Sumitomo Chemical Company, Limited Composition and method for controlling pests
KR20170021886A (en) 2014-07-04 2017-02-28 스미또모 가가꾸 가부시끼가이샤 Pest control composition and use for same
KR20170023963A (en) * 2014-06-26 2017-03-06 스미또모 가가꾸 가부시끼가이샤 Method for manufacturing 3-(alkyl sulfonyl)pyridine-2-carboxylic acid
WO2017043342A1 (en) * 2015-09-08 2017-03-16 住友化学株式会社 Method for producing triazole compound
WO2017043341A1 (en) * 2015-09-08 2017-03-16 住友化学株式会社 Triazole compound
WO2017050685A1 (en) 2015-09-25 2017-03-30 Syngenta Participations Ag Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems
WO2017050751A1 (en) 2015-09-25 2017-03-30 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2017055147A1 (en) 2015-09-28 2017-04-06 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2017072039A1 (en) 2015-10-26 2017-05-04 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2017077968A1 (en) * 2015-11-05 2017-05-11 住友化学株式会社 Condensed heterocyclic compound
WO2017089190A1 (en) 2015-11-23 2017-06-01 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur and cyclopropyl containing substituents
WO2017093180A1 (en) 2015-12-01 2017-06-08 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2017094750A1 (en) 2015-12-01 2017-06-08 日本農薬株式会社 3h-pyrrolopyridine compound or n-oxide thereof, or salts thereof, agricultural and horticultural insecticide containing compound, and use thereof
US9708341B2 (en) 2014-06-09 2017-07-18 Sumitomo Chemical Company, Limited Method for producing pyridine compound
AU2014213387B2 (en) * 2013-01-31 2017-08-03 Sumitomo Chemical Company, Limited Pest-control composition and pest-control method
WO2017134066A1 (en) 2016-02-05 2017-08-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2017133994A1 (en) * 2016-02-04 2017-08-10 Syngenta Participations Ag Pesticidally active derivatives with sulfur and cyclopropyl containing substituents
WO2017146226A1 (en) 2016-02-26 2017-08-31 日本農薬株式会社 Benzoxazole compound or salt thereof, agricultural/horticultural insecticide containing said compound, and method for using same
WO2017146220A1 (en) * 2016-02-26 2017-08-31 日本農薬株式会社 Quinoline compound having fused heterocycle linked thereto, n-oxide or salts thereof, and agricultural and horticultural insecticide containing compound, and method of using same
WO2017144341A1 (en) 2016-02-23 2017-08-31 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2017146221A1 (en) 2016-02-26 2017-08-31 日本農薬株式会社 Condensed heterocyclic compound having bonded heterocycles and salts thereof, agricultural/horticultural insecticide containing said compound, and method for using said insecticide
WO2017174414A1 (en) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Naphthaline-derivatives as pest control agents
WO2017174449A1 (en) 2016-04-07 2017-10-12 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
KR20170117079A (en) 2015-02-12 2017-10-20 닛산 가가쿠 고교 가부시키 가이샤 Condensed heterocyclic compound and noxious organism control agent
EP3241830A1 (en) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pesticides
WO2018003976A1 (en) * 2016-07-01 2018-01-04 日本農薬株式会社 N-alkylsulfonyl-fused heterocyclic compound or salt thereof, pesticide containing said compound, and method for using said pesticide
WO2018015289A1 (en) 2016-07-19 2018-01-25 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2018033455A1 (en) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2018041729A2 (en) 2016-09-01 2018-03-08 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US9920004B2 (en) 2014-06-26 2018-03-20 Sumitomo Chemical Company, Limited Method for producing phenolic compound
WO2018050825A1 (en) 2016-09-19 2018-03-22 Bayer Cropscience Aktiengesellschaft Pyrazolo [1,5-a]pyridine derivatives and their use as pesticides
EP3305786A2 (en) 2018-01-22 2018-04-11 Bayer CropScience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pesticides
WO2018065292A1 (en) 2016-10-06 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
WO2018065288A1 (en) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-[2-phenyl-1-(sulfonyl-methyl)-vinyl]-imidazo-[4,5-b] pyridine derivatives and related compounds as pesticides in plant protection
WO2018070502A1 (en) 2016-10-13 2018-04-19 日本農薬株式会社 1h-pyrrolopyridine compound, n-oxide of same, salt of same, pesticide for agricultural and horticultural use containing said compound, and method for using same
WO2018070503A1 (en) 2016-10-13 2018-04-19 日本農薬株式会社 1h-pyrrolopyridine compound or n-oxide or salt thereof, agricultural and horticultural insecticide containing said compound, and method of using said insecticide
WO2018077565A1 (en) 2016-10-27 2018-05-03 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur and hydroxylamine substituents
WO2018084142A1 (en) 2016-11-01 2018-05-11 日本農薬株式会社 Quinoline compound having oxime group, n-oxide or salt thereof, agricultural and horticultural insecticide comprising same and method for use thereof
WO2018084141A1 (en) 2016-11-01 2018-05-11 日本農薬株式会社 N-alkylsulfonylindoline compound, agricultural and horticultural insecticide comprising same and method for use thereof
WO2018091389A1 (en) 2016-11-17 2018-05-24 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
KR20180056745A (en) 2015-10-13 2018-05-29 니혼노야쿠가부시키가이샤 Condensed heterocyclic compounds having oxime groups or salts thereof, and pesticides for agricultural use containing the compounds and methods of using the same
WO2018099812A1 (en) 2016-12-01 2018-06-07 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018108726A1 (en) 2016-12-15 2018-06-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018124128A1 (en) 2016-12-27 2018-07-05 日本農薬株式会社 4h-pyrrolopyridine compound or salts thereof, agricultural/horticultural insecticide containing said compound, and method for using same
CN108290886A (en) * 2015-09-28 2018-07-17 拜耳作物科学股份公司 The fused bicyclic heterocycle derivative that 2- (miscellaneous) aryl as pest control agent replaces
WO2018130443A1 (en) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2018130437A1 (en) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2018138050A1 (en) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Condensed bicyclic heterocyclene derivatives as pest control agents
WO2018139436A1 (en) 2017-01-24 2018-08-02 住友化学株式会社 Fused heterocyclic compound and composition containing same
WO2018141954A1 (en) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Aryl or heteroaryl-substituted imidazo pyridine derivatives and their use as pesticides
WO2018141955A1 (en) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Process for preparing halogenated imidazopyridine derivatives
WO2018153778A1 (en) 2017-02-21 2018-08-30 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018174170A1 (en) 2017-03-23 2018-09-27 住友化学株式会社 Fused heterocyclic compound and composition containing same
KR20180116303A (en) 2016-03-10 2018-10-24 닛산 가가쿠 가부시키가이샤 Condensed heterocyclic compounds and pesticides
WO2018197315A1 (en) 2017-04-25 2018-11-01 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018197257A1 (en) 2017-04-24 2018-11-01 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic-compound derivatives as pest control agents
WO2018202540A1 (en) 2017-05-02 2018-11-08 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018215304A1 (en) 2017-05-22 2018-11-29 Syngenta Participations Ag Tetracyclic pyridazine sulphur containing compounds and their use as pesticides
WO2018221720A1 (en) 2017-06-01 2018-12-06 住友化学株式会社 Heterocyclic compound and composition containing same
WO2019008115A1 (en) 2017-07-07 2019-01-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019008072A1 (en) 2017-07-05 2019-01-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019013273A1 (en) 2017-07-13 2019-01-17 住友化学株式会社 Heterocyclic compound and harmful-arthropod control agent containing same
WO2019053182A1 (en) 2017-09-18 2019-03-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019059244A1 (en) 2017-09-21 2019-03-28 日本農薬株式会社 Benzimidazole compound having cyclopropylpyridyl group or salt thereof, agricultural and horticultural pesticide containing said compound, and method of using said pesticide
WO2019068572A1 (en) 2017-10-04 2019-04-11 Bayer Aktiengesellschaft Derivatives of heterocyclic compounds as pest control agents
WO2019076778A1 (en) 2017-10-16 2019-04-25 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur and sulfonimidamides containing substituents
WO2019124529A1 (en) 2017-12-22 2019-06-27 住友化学株式会社 Heterocyclic compound and harmful arthropod-controlling agent containing same
US10375962B2 (en) 2016-01-11 2019-08-13 Bayer Cropscience Aktiengesellschaft Heterocycle derivatives as pesticides
US10385048B2 (en) 2014-12-31 2019-08-20 Syngenta Participation Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2019162174A1 (en) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2019168140A1 (en) 2018-03-02 2019-09-06 日本農薬株式会社 Amide compound or salt thereof, and agricultural and horticultural microbicide containing said compound, and method of using same
WO2019175045A1 (en) 2018-03-12 2019-09-19 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2019201921A1 (en) 2018-04-20 2019-10-24 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2019225663A1 (en) 2018-05-22 2019-11-28 日本農薬株式会社 Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent containing said compound, and method for using same
WO2019229088A1 (en) 2018-05-30 2019-12-05 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019229089A1 (en) 2018-05-31 2019-12-05 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019234160A1 (en) 2018-06-06 2019-12-12 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020053282A1 (en) 2018-09-13 2020-03-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2020084075A1 (en) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
WO2020141136A1 (en) 2018-12-31 2020-07-09 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020174096A1 (en) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020173860A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2020173861A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2020174094A1 (en) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020178789A1 (en) 2019-03-07 2020-09-10 Pi Industries Ltd. Fused heterocyclic compounds and their use as pest control agents
WO2020182577A1 (en) 2019-03-08 2020-09-17 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020188014A1 (en) 2019-03-20 2020-09-24 Syngenta Crop Protection Ag Pesticidally active azole amide compounds
WO2020250183A1 (en) 2019-06-13 2020-12-17 Pi Industries Ltd. Fused heterocyclic compounds and their use as pest control agents
WO2020254530A1 (en) 2019-06-18 2020-12-24 Syngenta Crop Protection Ag 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide derivatives and the respective -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoline-2-, and -naphthalene-2-carboxamide derivatives as pesticides
US10927106B2 (en) 2016-10-12 2021-02-23 Pharmasum Therapeutics As Benzothiazole derivatives as DYRK1 inhibitors
WO2021053110A1 (en) 2019-09-20 2021-03-25 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur and sulfoximine containing substituents
WO2021107110A1 (en) 2019-11-28 2021-06-03 日本農薬株式会社 Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent comprising said compound, and method for using said insecticidal and acaricidal agent
WO2021136722A1 (en) 2019-12-31 2021-07-08 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2021140122A1 (en) 2020-01-06 2021-07-15 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11124480B2 (en) 2016-04-06 2021-09-21 Sumitomo Chemical Company, Limited Heterocyclic compound
WO2021204589A1 (en) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
US11149027B2 (en) 2016-03-31 2021-10-19 Sumitomo Chemical Company, Limited Heterocyclic compound
WO2021213978A1 (en) 2020-04-21 2021-10-28 Bayer Aktiengesellschaft 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents
WO2021213929A1 (en) 2020-04-20 2021-10-28 Syngenta Crop Protection Ag Pesticidally active substituted 1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one derivatives with sulfur containing substituents
WO2021219810A1 (en) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2021224409A1 (en) 2020-05-06 2021-11-11 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022002818A1 (en) 2020-07-02 2022-01-06 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2022013417A1 (en) 2020-07-17 2022-01-20 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11229208B2 (en) 2013-07-02 2022-01-25 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
WO2022017975A1 (en) 2020-07-18 2022-01-27 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US20220061325A1 (en) * 2019-02-26 2022-03-03 Nippon Soda Co., Ltd. Pyridine n-oxide compound and pest control agent
WO2022043576A2 (en) 2020-08-31 2022-03-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049144A1 (en) 2020-09-02 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049146A1 (en) 2020-09-02 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049141A1 (en) 2020-09-01 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022053567A1 (en) 2020-09-09 2022-03-17 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022157334A1 (en) 2021-01-21 2022-07-28 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022238391A1 (en) 2021-05-12 2022-11-17 Bayer Aktiengesellschaft 2-(het)aryl-substituted condensed heterocycle derivatives as pest control agents
US11570992B2 (en) 2016-04-01 2023-02-07 Basf Se Bicyclic compounds
WO2023017094A1 (en) 2021-08-10 2023-02-16 Syngenta Crop Protection Ag 2,2-difluoro-5h-[1,3]dioxolo[4,5-f]isoindol-7-one derivatives as pesticides
WO2023036706A1 (en) 2021-09-07 2023-03-16 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
WO2023036707A1 (en) 2021-09-07 2023-03-16 Bayer Aktiengesellschaft Substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, salts thereof and their use as herbicidally active substances
EP3733672B1 (en) 2017-12-25 2023-03-22 Sumitomo Chemical Company, Limited Heterocyclic compounds and noxious arthropod control agent containing same
WO2023072945A1 (en) 2021-10-25 2023-05-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023148369A1 (en) 2022-02-07 2023-08-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023148368A1 (en) 2022-02-07 2023-08-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023187191A1 (en) 2022-04-01 2023-10-05 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11926623B2 (en) 2018-06-26 2024-03-12 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2024089023A1 (en) 2022-10-25 2024-05-02 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024094575A1 (en) 2022-10-31 2024-05-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024126388A1 (en) 2022-12-12 2024-06-20 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024156664A1 (en) 2023-01-23 2024-08-02 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024189139A1 (en) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Control of pests resistant to insecticides

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI589570B (en) 2011-08-04 2017-07-01 住友化學股份有限公司 Fused heterocyclic compound and use thereof for pest control
JP6217630B2 (en) 2012-05-30 2017-10-25 住友化学株式会社 Fused heterocyclic compounds
WO2013180193A1 (en) 2012-05-31 2013-12-05 住友化学株式会社 Fused heterocyclic compound
CN104395300A (en) 2012-06-22 2015-03-04 住友化学株式会社 Fused heterocyclic compound
US9185910B2 (en) * 2012-07-31 2015-11-17 Sumitomo Chemical Company, Limited Amide compound
US20150284341A1 (en) * 2014-04-07 2015-10-08 Catylix, Inc. Fluoroalkyl-substituted derivatives of pyridine, pyrimidine, and pyrazine
EP3135114B1 (en) 2014-04-24 2019-03-20 Sumitomo Chemical Company, Limited Diaryl-azole compound
WO2015198859A1 (en) * 2014-06-26 2015-12-30 住友化学株式会社 Condensed heterocyclic compound
JP2014208695A (en) * 2014-07-04 2014-11-06 住友化学株式会社 Pest control composition and use thereof
BR112017005122A2 (en) * 2014-09-16 2018-07-31 Syngenta Participations Ag pesticide-active tetracyclic derivatives with sulfur-containing substituents.
WO2016058928A1 (en) * 2014-10-14 2016-04-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
CN111646989A (en) * 2015-03-12 2020-09-11 先正达参股股份有限公司 Pesticidally active tetracyclic derivatives with sulfur-containing substituents
WO2017026384A1 (en) * 2015-08-07 2017-02-16 日本農薬株式会社 Imidazole compound or salts thereof, and agricultural and horticultural insecticide containing said compound and method for using same
TW201717761A (en) * 2015-09-07 2017-06-01 住友化學股份有限公司 Pest control composition
TW201715969A (en) * 2015-09-07 2017-05-16 住友化學股份有限公司 Pest control composition
US10730872B2 (en) * 2015-11-16 2020-08-04 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing sustitutents
EP3415513A4 (en) * 2016-02-12 2019-07-17 Sumitomo Chemical Company Limited Method for producing benzoxazole compound
JP2019206478A (en) * 2016-08-31 2019-12-05 日本農薬株式会社 3h-pyrrolopyridine compound and n-oxide, or salts thereof, and horticultural agent containing the compound and use method thereof
BR112019004085B1 (en) * 2016-09-01 2022-10-04 Nihon Nohyaku Co., Ltd. COMPOUND, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPOSITION, METHOD FOR USING AN AGRICULTURAL AND HORTICULTURAL INSECTICIDE, USE OF THE COMPOUND OR THE SALT THEREOF AND COMPOSITION FOR CONTROL OF ECTOPARASITES
CN109843066A (en) * 2016-09-27 2019-06-04 巴斯夫欧洲公司 Pesticide combination
WO2018105632A1 (en) * 2016-12-07 2018-06-14 日本農薬株式会社 Quinoline compound having carbamate group, salt of same, insecticide for agricultural and horticultural use containing said compound, and use of said insecticide
US10562885B2 (en) * 2017-03-06 2020-02-18 Sumitomo Chemical Company, Limited Method for producing triazole compound
WO2019065568A1 (en) * 2017-09-26 2019-04-04 住友化学株式会社 Heterocyclic compound and harmful arthropod-controlling agent containing same
WO2019176791A1 (en) * 2018-03-12 2019-09-19 日本曹達株式会社 Heteroaryl pyrimidine compound and pest control agent
TWI818061B (en) * 2018-08-20 2023-10-11 日商住友化學股份有限公司 Amide compound and use thereof
US20210347777A1 (en) * 2018-10-23 2021-11-11 Basf Se Tricyclic pesticidal compounds
WO2022224919A1 (en) 2021-04-21 2022-10-27 住友化学株式会社 Method for controlling disease-transmitting insects using condensed heterocyclic compound

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0508800A1 (en) * 1991-04-11 1992-10-14 Rhone Poulenc Agriculture Ltd. New Herbicides
EP1302466A1 (en) * 2000-07-04 2003-04-16 Ube Industries, Ltd. Benzoxazole compound, process for producing the same, and herbicide
JP2004034438A (en) 2002-07-02 2004-02-05 Mitsui Chemicals Inc Optical recording medium and oxazole compound
EP2274983A1 (en) * 2008-04-21 2011-01-19 Sumitomo Chemical Company, Limited Harmful arthropod control composition, and fused heterocyclic compound
WO2011040629A1 (en) * 2009-09-30 2011-04-07 Sumitomo Chemical Company, Limited Composition and method for controlling arthropod pests
WO2011049221A1 (en) * 2009-10-20 2011-04-28 Sumitomo Chemical Company, Limited Composition and method for controlling arthropod pests
JP2011170833A (en) 2010-02-17 2011-09-01 Hitachi Ltd Method and apparatus to manage object based tier
JP2012079323A (en) 2007-05-30 2012-04-19 Kyocera Corp Portable electronic device and character display method for portable electronic device
JP2012122837A (en) 2010-12-08 2012-06-28 Suzuki Motor Corp Device and method for measuring load displacement characteristics of rotary operation tool

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE949059C (en) * 1953-07-03 1956-09-13 Bayer Ag Process for the preparation of imidazole derivatives
GB8401508D0 (en) 1984-01-20 1984-02-22 Monsanto Europe Sa Compounds useful as rubber/metal bonding promoters
IL87709A (en) * 1987-09-16 1992-11-15 Pfizer Process for preparing haloalkyl thiazoles and some such novel haloalkyl thiazoles
EP2359930A1 (en) 2005-12-16 2011-08-24 Dow Global Technologies LLC A polymer prepared in the presence of metal complexes bearing a polydentate heteroatom ligand
US8273764B2 (en) 2009-04-28 2012-09-25 Sumitomo Chemical Company, Limited Fused heterocyclic compounds and use thereof
US8748618B2 (en) * 2009-05-13 2014-06-10 University Of Virginia Patent Foundation Inhibitors of inv(16) leukemia
JP5540640B2 (en) 2009-10-07 2014-07-02 住友化学株式会社 Heterocyclic compounds and their use for controlling harmful arthropods
WO2011162364A1 (en) 2010-06-23 2011-12-29 住友化学株式会社 Noxious arthropod control composition, and heterocyclic compound
JP5790440B2 (en) 2010-12-01 2015-10-07 住友化学株式会社 Pyrimidine compounds and their use for pest control
BR122019003178B1 (en) 2010-12-24 2020-04-28 Sumitomo Chemical Co pest control method
TWI589570B (en) 2011-08-04 2017-07-01 住友化學股份有限公司 Fused heterocyclic compound and use thereof for pest control
EP2938601B1 (en) 2012-12-27 2018-05-16 Sumitomo Chemical Company Limited Fused oxazole compounds and use thereof for pest control

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0508800A1 (en) * 1991-04-11 1992-10-14 Rhone Poulenc Agriculture Ltd. New Herbicides
EP1302466A1 (en) * 2000-07-04 2003-04-16 Ube Industries, Ltd. Benzoxazole compound, process for producing the same, and herbicide
JP2004034438A (en) 2002-07-02 2004-02-05 Mitsui Chemicals Inc Optical recording medium and oxazole compound
JP2012079323A (en) 2007-05-30 2012-04-19 Kyocera Corp Portable electronic device and character display method for portable electronic device
EP2274983A1 (en) * 2008-04-21 2011-01-19 Sumitomo Chemical Company, Limited Harmful arthropod control composition, and fused heterocyclic compound
WO2011040629A1 (en) * 2009-09-30 2011-04-07 Sumitomo Chemical Company, Limited Composition and method for controlling arthropod pests
WO2011049221A1 (en) * 2009-10-20 2011-04-28 Sumitomo Chemical Company, Limited Composition and method for controlling arthropod pests
JP2011170833A (en) 2010-02-17 2011-09-01 Hitachi Ltd Method and apparatus to manage object based tier
JP2012122837A (en) 2010-12-08 2012-06-28 Suzuki Motor Corp Device and method for measuring load displacement characteristics of rotary operation tool

Cited By (326)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013191113A1 (en) * 2012-06-18 2013-12-27 住友化学株式会社 Fused heterocyclic compound
WO2014104407A1 (en) * 2012-12-27 2014-07-03 Sumitomo Chemical Company, Limited Fused oxazole compounds and use thereof for pest control
US9615580B2 (en) 2012-12-27 2017-04-11 Sumitomo Chemical Company, Limited Fused heterocyclic compound and use thereof for pest control
CN104903303B (en) * 2012-12-27 2016-11-16 住友化学株式会社 Condensed ring azole compounds is used for the purposes of Pest control with it
CN104903303A (en) * 2012-12-27 2015-09-09 住友化学株式会社 Fused oxazole compounds and use thereof for pest control
WO2014119699A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest-control composition and pest-control method
US9883675B2 (en) 2013-01-31 2018-02-06 Sumitomo Chemical Company, Limited Method for controlling pests
US9723835B2 (en) 2013-01-31 2017-08-08 Sumitomo Chemical Company, Limited Pest control composition and method for controlling pest
AU2014213385B2 (en) * 2013-01-31 2017-08-03 Sumitomo Chemical Company, Limited Pest-control composition and pest-control method
AU2014213387B2 (en) * 2013-01-31 2017-08-03 Sumitomo Chemical Company, Limited Pest-control composition and pest-control method
US20150366207A1 (en) * 2013-01-31 2015-12-24 Sumitomo Chemical Company, Limited Composition and method for controlling pests
US9549559B2 (en) 2013-01-31 2017-01-24 Sumitomo Chemical Company, Limited Composition and method for controlling pests
EP2952099B1 (en) * 2013-01-31 2018-10-17 Sumitomo Chemical Company, Limited Pest-control composition and pest-control method
AU2014213394B2 (en) * 2013-01-31 2017-07-13 Sumitomo Chemical Company, Limited Pest-control method
WO2014119494A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest control composition and method for controlling pest
US9974307B2 (en) 2013-01-31 2018-05-22 Sumitomo Chemical Company, Limited Composition and method for controlling pests
US9854805B2 (en) * 2013-01-31 2018-01-02 Sumitomo Chemical Company, Limited Composition and method for controlling pests
WO2014119679A1 (en) * 2013-01-31 2014-08-07 住友化学株式会社 Pest-control method
EP2955178A4 (en) * 2013-02-06 2016-11-30 Sumitomo Chemical Co Condensed heterocyclic compound
CN104968663B (en) * 2013-02-06 2017-05-17 住友化学株式会社 Condensed heterocyclic compound
EP2955179A4 (en) * 2013-02-06 2016-09-28 Sumitomo Chemical Co Condensed heterocyclic compound
CN104968663A (en) * 2013-02-06 2015-10-07 住友化学株式会社 Condensed heterocyclic compound
CN104968659A (en) * 2013-02-06 2015-10-07 住友化学株式会社 Condensed heterocyclic compound
WO2014125651A1 (en) * 2013-02-13 2014-08-21 Sumitomo Chemical Company, Limited Pest controlling composition and use thereof
CN105246876B (en) * 2013-02-28 2017-06-16 住友化学株式会社 Condensed heterocyclic compouds and its Pesticidal purposes
JPWO2014132971A1 (en) * 2013-02-28 2017-02-02 住友化学株式会社 Fused heterocyclic compounds and their use for pest control
WO2014132972A1 (en) * 2013-02-28 2014-09-04 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
WO2014132971A1 (en) * 2013-02-28 2014-09-04 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
JPWO2014132972A1 (en) * 2013-02-28 2017-02-02 住友化学株式会社 Fused heterocyclic compounds and their use for pest control
CN105164109A (en) * 2013-02-28 2015-12-16 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
WO2014149207A3 (en) * 2013-03-15 2015-02-26 Dow Agrosciences Llc Benzimidazole-based insecticidal compositions and related methods
US9936703B2 (en) 2013-03-15 2018-04-10 Nihon Nohyaku Co., Ltd. Condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
CN105051045B (en) * 2013-03-15 2017-07-28 日本农药株式会社 Fused heterocyclic compound or its esters and salt, garderning pesticide and its application method containing the compound
WO2014142292A1 (en) 2013-03-15 2014-09-18 日本農薬株式会社 Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide
JPWO2014142292A1 (en) * 2013-03-15 2017-02-16 日本農薬株式会社 Fused heterocyclic compounds or salts thereof, agricultural and horticultural insecticides containing the compounds, and methods of use thereof
CN105051045A (en) * 2013-03-15 2015-11-11 日本农药株式会社 Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide
WO2014148451A1 (en) * 2013-03-19 2014-09-25 日本農薬株式会社 Fused heterocyclic compound or salt thereof, pesticide for agricultural and horticultural use containing said compound, and usage method therefor
WO2014157600A1 (en) * 2013-03-29 2014-10-02 日本農薬株式会社 Condensed heterocyclic compound or salts thereof, agricultural and horticultural pesticide containing said compound, and method for using same
US9920050B2 (en) 2013-07-01 2018-03-20 Sumitomo Chemical Company, Limited Fused heterocyclic compound and pest control use thereof
CN105358555A (en) * 2013-07-01 2016-02-24 住友化学株式会社 Fused heterocyclic compound and pest control use thereof
WO2015002211A1 (en) 2013-07-01 2015-01-08 住友化学株式会社 Fused heterocyclic compound and pest control use thereof
JPWO2015002211A1 (en) * 2013-07-01 2017-02-23 住友化学株式会社 Fused heterocyclic compounds and their use for pest control
EP3018130A4 (en) * 2013-07-01 2017-03-15 Sumitomo Chemical Company, Limited Fused heterocyclic compound and pest control use thereof
JP2018115176A (en) * 2013-07-01 2018-07-26 住友化学株式会社 Fused heterocyclic compound and pest control applications thereof
CN105431433A (en) * 2013-07-02 2016-03-23 先正达参股股份有限公司 Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
EP3778598A3 (en) * 2013-07-02 2021-08-04 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
EP3778598A2 (en) 2013-07-02 2021-02-17 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
CN105431433B (en) * 2013-07-02 2018-04-06 先正达参股股份有限公司 There are two rings or tricyclic heterocyclic with sulfur-bearing substituent for killing harmful organism activity
WO2015000715A1 (en) 2013-07-02 2015-01-08 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
US11229208B2 (en) 2013-07-02 2022-01-25 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
US10939682B2 (en) 2013-07-02 2021-03-09 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
EP3778599A3 (en) * 2013-07-02 2021-04-21 Syngenta Participations Ag Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents
CN107652292B (en) * 2013-07-02 2020-11-17 先正达参股股份有限公司 Pesticidally active bicyclic or tricyclic heterocycles with sulfur-containing substituents
WO2015059039A1 (en) * 2013-10-24 2015-04-30 Syngenta Participations Ag Method of protecting a plant propagation material
WO2015072463A1 (en) 2013-11-12 2015-05-21 日本農薬株式会社 Amide compound or salt thereof, agricultural/horticultural insecticide/bactericide containing said compound, and method for using same
US10123537B2 (en) 2013-11-12 2018-11-13 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide
US9888686B2 (en) 2013-11-12 2018-02-13 Nihon Nohyaku Co., Ltd. Amide compound or salt thereof, agricultural and horticultural insecticide and microbicide comprising the compound, and method for using the insecticide and microbicide
WO2015071180A1 (en) 2013-11-13 2015-05-21 Syngenta Participations Ag Pesticidally active bicyclic heterocycles with sulphur containing substituents
EP2873668A1 (en) 2013-11-13 2015-05-20 Syngenta Participations AG. Pesticidally active bicyclic heterocycles with sulphur containing substituents
JP2017502927A (en) * 2013-11-13 2017-01-26 シンジェンタ パーティシペーションズ アーゲー Bicyclic heterocycles with sulfur-containing substituents active in pest control
WO2015091945A1 (en) 2013-12-20 2015-06-25 Syngenta Participations Ag Pesticidally active substituted 5,5-bicyclic heterocycles with sulphur containing substituents
US11274097B2 (en) 2014-02-17 2022-03-15 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
KR20160122809A (en) * 2014-02-17 2016-10-24 바이엘 크롭사이언스 악티엔게젤샤프트 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
WO2015121136A1 (en) * 2014-02-17 2015-08-20 Bayer Cropscience Ag 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
US10364243B2 (en) 2014-02-17 2019-07-30 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
CN106414441A (en) * 2014-02-17 2017-02-15 拜耳作物科学股份公司 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
KR102362756B1 (en) 2014-02-17 2022-02-11 바이엘 크롭사이언스 악티엔게젤샤프트 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
CN106414441B (en) * 2014-02-17 2019-08-13 拜耳作物科学股份公司 The fused bicyclic heterocycle derivative substituted as 2- (miscellaneous) aryl-of pest control agent
CN106414441B9 (en) * 2014-02-17 2019-09-20 拜耳作物科学股份公司 2- (hetero) aryl-substituted fused bicyclic heterocyclic derivatives as pest control agents
EP3115363A4 (en) * 2014-03-07 2017-09-13 Sumitomo Chemical Company Limited Fused heterocyclic compound and pest control application thereof
AU2015224876B2 (en) * 2014-03-07 2018-09-13 Sumitomo Chemical Company, Limited Fused heterocyclic compound and pest control application thereof
KR20160120748A (en) 2014-03-07 2016-10-18 수미토모 케미칼 컴퍼니 리미티드 Fused heterocyclic compound and pest control application thereof
RU2672880C2 (en) * 2014-03-07 2018-11-20 Сумитомо Кемикал Компани, Лимитед Fused heterocyclic compound and use thereof for pest control
TWI649320B (en) * 2014-03-07 2019-02-01 日商住友化學股份有限公司 Condensed heterocyclic compound and its harmful biological control use
CN106103433A (en) * 2014-03-07 2016-11-09 住友化学株式会社 Fused heterocyclic compound and PCO application thereof
US9668482B1 (en) 2014-03-07 2017-06-06 Sumitomo Chemical Company, Limited Fused heterocyclic compound and pest control application thereof
WO2015177063A1 (en) 2014-05-19 2015-11-26 Syngenta Participations Ag Insecticidally active amide derivatives with sulfur-substituted phenyl or pyridine groups
EP3159339A4 (en) * 2014-06-09 2017-12-06 Sumitomo Chemical Company, Limited Method for producing pyridine compound
US9708341B2 (en) 2014-06-09 2017-07-18 Sumitomo Chemical Company, Limited Method for producing pyridine compound
US9920004B2 (en) 2014-06-26 2018-03-20 Sumitomo Chemical Company, Limited Method for producing phenolic compound
AU2015282127B2 (en) * 2014-06-26 2018-12-20 Sumitomo Chemical Company, Limited Method for producing fused heterocyclic compound
US10005766B2 (en) 2014-06-26 2018-06-26 Sumitomo Chemical Company, Limited Method for producing fused heterocyclic compound
WO2015198817A1 (en) * 2014-06-26 2015-12-30 Sumitomo Chemical Company, Limited Method for producing fused heterocyclic compound
US9850209B2 (en) 2014-06-26 2017-12-26 Sumitomo Chemical Company, Limited Method for manufacturing 3-(alkylsulfonyl)pyridine-2-carboxylic acid
KR102332262B1 (en) * 2014-06-26 2021-11-26 스미또모 가가꾸 가부시끼가이샤 Method for manufacturing 3-(alkyl sulfonyl)pyridine-2-carboxylic acid
US9815786B2 (en) 2014-06-26 2017-11-14 Sumitomo Chemical Company, Limited Method for manufacturing 3-(alkylsulfonyl)pyridine-2-carboxylic acid
KR102292928B1 (en) 2014-06-26 2021-08-25 수미토모 케미칼 컴퍼니 리미티드 Method for producing fused heterocyclic compound
AU2015281846B2 (en) * 2014-06-26 2019-08-01 Sumitomo Chemical Company, Limited Method for manufacturing 3-(alkyl sulfonyl)pyridine-2-carboxylic acid
EP3162795A4 (en) * 2014-06-26 2018-02-28 Sumitomo Chemical Company, Limited Method for manufacturing 3-(alkyl sulfonyl)pyridine-2-carboxylic acid
KR20170023963A (en) * 2014-06-26 2017-03-06 스미또모 가가꾸 가부시끼가이샤 Method for manufacturing 3-(alkyl sulfonyl)pyridine-2-carboxylic acid
TWI657088B (en) * 2014-06-26 2019-04-21 日商住友化學股份有限公司 Method for producing fused heterocyclic compound
KR20170021256A (en) * 2014-06-26 2017-02-27 수미토모 케미칼 컴퍼니 리미티드 Method for producing fused heterocyclic compound
KR20170021886A (en) 2014-07-04 2017-02-28 스미또모 가가꾸 가부시끼가이샤 Pest control composition and use for same
US9775353B2 (en) 2014-07-08 2017-10-03 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016005263A1 (en) * 2014-07-08 2016-01-14 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US20170156329A1 (en) * 2014-07-08 2017-06-08 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10051864B2 (en) 2014-07-08 2018-08-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016012395A1 (en) * 2014-07-22 2016-01-28 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016020286A1 (en) * 2014-08-07 2016-02-11 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US9949483B2 (en) 2014-08-07 2018-04-24 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10450311B2 (en) * 2014-08-12 2019-10-22 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016023954A2 (en) 2014-08-12 2016-02-18 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10005775B2 (en) 2014-08-12 2018-06-26 Syngenta Participations, Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016023954A3 (en) * 2014-08-12 2016-04-07 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016026848A1 (en) * 2014-08-21 2016-02-25 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10081641B2 (en) 2014-08-21 2018-09-25 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016030229A1 (en) * 2014-08-25 2016-03-03 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US9809587B2 (en) 2014-08-25 2017-11-07 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016046071A1 (en) * 2014-09-25 2016-03-31 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10494366B2 (en) 2014-12-01 2019-12-03 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016087257A1 (en) * 2014-12-01 2016-06-09 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016091731A1 (en) 2014-12-11 2016-06-16 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
RU2765282C2 (en) * 2014-12-17 2022-01-28 Зингента Партисипейшнс Аг Pesticide-active heterocyclic derivatives with sulphur-containing substituents
US10323030B2 (en) 2014-12-17 2019-06-18 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016096584A1 (en) * 2014-12-17 2016-06-23 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US11072608B2 (en) 2014-12-17 2021-07-27 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2016107742A1 (en) * 2014-12-29 2016-07-07 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
US10196398B2 (en) 2014-12-29 2019-02-05 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
US10385048B2 (en) 2014-12-31 2019-08-20 Syngenta Participation Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2016116338A1 (en) * 2015-01-19 2016-07-28 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
CN114524819A (en) * 2015-01-19 2022-05-24 先正达参股股份有限公司 Pesticidally active polycyclic derivatives with sulfur-containing substituents
US10981907B2 (en) 2015-01-19 2021-04-20 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
US10138238B2 (en) 2015-01-19 2018-11-27 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
CN107207460A (en) * 2015-01-29 2017-09-26 日本农药株式会社 Fused heterocyclic compound or its esters with cycloalkyl pyridine radicals and salt, garderning pesticide and its application method containing the compound
RU2676760C1 (en) * 2015-01-29 2019-01-11 Нихон Нохияку Ко., Лтд. Condensed heterocyclic compound with cycloalkyl pyridyl group, or its salt, agriculture and crop insecticide, including this compound, and method of application thereof
AU2016213001B2 (en) * 2015-01-29 2019-01-03 Nihon Nohyaku Co., Ltd. Fused heterocyclic compound having cycloalkylpyridyl group or salt thereof, and agricultural or horticultural insecticide containing said compound and use method therefor
US10266552B2 (en) 2015-01-29 2019-04-23 Nihon Nohyaku Co., Ltd. Condensed heterocyclic compound having cycloalkylpyridyl group or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
JPWO2016121997A1 (en) * 2015-01-29 2017-12-07 日本農薬株式会社 Fused heterocyclic compounds having a cycloalkylpyridyl group or salts thereof, agricultural and horticultural insecticides containing the compounds, and methods of use thereof
US20180002347A1 (en) * 2015-01-29 2018-01-04 Nihon Nohyaku Co., Ltd. Condensed heterocyclic compound having cycloalkylpyridyl group or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
WO2016121997A1 (en) * 2015-01-29 2016-08-04 日本農薬株式会社 Fused heterocyclic compound having cycloalkylpyridyl group or salt thereof, and agricultural or horticultural insecticide containing said compound and use method therefor
WO2016120182A1 (en) 2015-01-30 2016-08-04 Syngenta Participations Ag Pesticidally active amide heterocyclic derivatives with sulphur containing substituents
WO2016125622A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzoxazole compound, and use thereof for noxious arthropod control
WO2016125621A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzimidazole compound, and use thereof for noxious arthropod control
US10087192B2 (en) 2015-02-05 2018-10-02 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
US10654845B2 (en) 2015-02-05 2020-05-19 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
WO2016124557A1 (en) 2015-02-05 2016-08-11 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
WO2016124563A1 (en) 2015-02-05 2016-08-11 Bayer Cropscience Aktiengesellschsaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
US10464950B2 (en) 2015-02-12 2019-11-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10882869B2 (en) 2015-02-12 2021-01-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
KR20170117079A (en) 2015-02-12 2017-10-20 닛산 가가쿠 고교 가부시키 가이샤 Condensed heterocyclic compound and noxious organism control agent
WO2016142327A1 (en) * 2015-03-12 2016-09-15 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
US10494368B2 (en) 2015-03-12 2019-12-03 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
US10131662B2 (en) 2015-03-12 2018-11-20 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
WO2016162318A1 (en) 2015-04-08 2016-10-13 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents and intermediate product
US10188108B2 (en) 2015-04-08 2019-01-29 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2016169886A1 (en) 2015-04-24 2016-10-27 Syngenta Crop Protection Ag Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocyles
EP3656770A2 (en) 2015-04-24 2020-05-27 Syngenta Participations AG Pesticidally active polycyclic derivatives with sulfur substituted five-membered ring heterocycles
WO2016169882A1 (en) 2015-04-24 2016-10-27 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur substituted five membered ring heterocyles
WO2017001314A1 (en) 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active polycyclic derivatives with sulfur containing substituents
WO2017001311A1 (en) 2015-07-01 2017-01-05 Syngenta Participations Ag Pesticidally active tetracyclic derivatives with sulfur containing substituents
US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
US10986840B2 (en) 2015-08-07 2021-04-27 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
EP3896065A1 (en) 2015-08-07 2021-10-20 Bayer CropScience Aktiengesellschaft 2-(het)aryl-substituted condensed heterocycle derivatives as pesticides
EP3896066A2 (en) 2015-08-07 2021-10-20 Bayer CropScience Aktiengesellschaft 2-(het)aryl-substituted condensed heterocycle derivatives as pesticides
WO2017043341A1 (en) * 2015-09-08 2017-03-16 住友化学株式会社 Triazole compound
WO2017043342A1 (en) * 2015-09-08 2017-03-16 住友化学株式会社 Method for producing triazole compound
WO2017050751A1 (en) 2015-09-25 2017-03-30 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2017050685A1 (en) 2015-09-25 2017-03-30 Syngenta Participations Ag Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems
US10736320B2 (en) 2015-09-25 2020-08-11 Syngenta Participations Ag Pesticidally active polycyclic derivatives with 5-membered sulfur containing heterocyclic ring systems
CN108290886B (en) * 2015-09-28 2020-11-03 拜耳作物科学股份公司 2- (hetero) aryl-substituted fused bicyclic heterocyclic derivatives as pest control agents
TWI720023B (en) * 2015-09-28 2021-03-01 德商拜耳作物科學股份有限公司 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
US10745398B2 (en) 2015-09-28 2020-08-18 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
WO2017055147A1 (en) 2015-09-28 2017-04-06 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
CN108290886A (en) * 2015-09-28 2018-07-17 拜耳作物科学股份公司 The fused bicyclic heterocycle derivative that 2- (miscellaneous) aryl as pest control agent replaces
KR20180056745A (en) 2015-10-13 2018-05-29 니혼노야쿠가부시키가이샤 Condensed heterocyclic compounds having oxime groups or salts thereof, and pesticides for agricultural use containing the compounds and methods of using the same
US11787809B2 (en) 2015-10-13 2023-10-17 Nihon Nohyaku Co., Ltd. Oxime group-containing condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
RU2721119C2 (en) * 2015-10-13 2020-05-15 Нихон Нохияку Ко., Лтд. Containing an oxime group of a condensed heterocyclic compound or a salt thereof, an agricultural and garden insecticide containing said compound, and a method of using said insecticide
WO2017072039A1 (en) 2015-10-26 2017-05-04 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
US10550116B2 (en) 2015-10-26 2020-02-04 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
CN108349970B (en) * 2015-11-05 2021-03-05 住友化学株式会社 Fused heterocyclic compound
WO2017077968A1 (en) * 2015-11-05 2017-05-11 住友化学株式会社 Condensed heterocyclic compound
US10709133B2 (en) 2015-11-05 2020-07-14 Sumitomo Chemical Company, Limited Condensed heterocyclic compound
CN108349970A (en) * 2015-11-05 2018-07-31 住友化学株式会社 Condensed heterocyclic compouds
WO2017089190A1 (en) 2015-11-23 2017-06-01 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur and cyclopropyl containing substituents
WO2017093180A1 (en) 2015-12-01 2017-06-08 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2017094750A1 (en) 2015-12-01 2017-06-08 日本農薬株式会社 3h-pyrrolopyridine compound or n-oxide thereof, or salts thereof, agricultural and horticultural insecticide containing compound, and use thereof
KR20180080309A (en) 2015-12-01 2018-07-11 니혼노야쿠가부시키가이샤 3H-pyrrolopyridine compound or an N-oxide thereof, or a salt thereof, and an agricultural pesticide containing the compound and a method of using the same
US10375962B2 (en) 2016-01-11 2019-08-13 Bayer Cropscience Aktiengesellschaft Heterocycle derivatives as pesticides
WO2017133994A1 (en) * 2016-02-04 2017-08-10 Syngenta Participations Ag Pesticidally active derivatives with sulfur and cyclopropyl containing substituents
WO2017134066A1 (en) 2016-02-05 2017-08-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2017144341A1 (en) 2016-02-23 2017-08-31 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
US10575525B2 (en) 2016-02-26 2020-03-03 Nihon Nohyaku Co., Ltd. Benzoxazole compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
WO2017146220A1 (en) * 2016-02-26 2017-08-31 日本農薬株式会社 Quinoline compound having fused heterocycle linked thereto, n-oxide or salts thereof, and agricultural and horticultural insecticide containing compound, and method of using same
WO2017146226A1 (en) 2016-02-26 2017-08-31 日本農薬株式会社 Benzoxazole compound or salt thereof, agricultural/horticultural insecticide containing said compound, and method for using same
KR20180095024A (en) 2016-02-26 2018-08-24 니혼노야쿠가부시키가이샤 Benzoxazole compounds or salts thereof, and pesticides for agricultural use containing the compounds and methods of using the same
KR20180095023A (en) 2016-02-26 2018-08-24 니혼노야쿠가부시키가이샤 A condensed heterocyclic compound or a salt thereof conjugated with a heterocycle, an insecticide for agricultural use containing the compound and a method of using the same
RU2709615C1 (en) * 2016-02-26 2019-12-19 Нихон Нохияку Ко., Лтд. Benzoxazole compound or salt thereof, agricultural and garden insecticide containing compound, and method of using insecticide
WO2017146221A1 (en) 2016-02-26 2017-08-31 日本農薬株式会社 Condensed heterocyclic compound having bonded heterocycles and salts thereof, agricultural/horticultural insecticide containing said compound, and method for using said insecticide
US11208410B2 (en) 2016-02-26 2021-12-28 Nihon Nohyaku Co., Ltd. Heterocycle-bound condensed heterocyclic compound or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10640518B2 (en) 2016-03-10 2020-05-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
KR20180116303A (en) 2016-03-10 2018-10-24 닛산 가가쿠 가부시키가이샤 Condensed heterocyclic compounds and pesticides
US11149027B2 (en) 2016-03-31 2021-10-19 Sumitomo Chemical Company, Limited Heterocyclic compound
US11570992B2 (en) 2016-04-01 2023-02-07 Basf Se Bicyclic compounds
WO2017174414A1 (en) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Naphthaline-derivatives as pest control agents
US11124480B2 (en) 2016-04-06 2021-09-21 Sumitomo Chemical Company, Limited Heterocyclic compound
WO2017174449A1 (en) 2016-04-07 2017-10-12 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
EP3241830A1 (en) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pesticides
WO2018003976A1 (en) * 2016-07-01 2018-01-04 日本農薬株式会社 N-alkylsulfonyl-fused heterocyclic compound or salt thereof, pesticide containing said compound, and method for using said pesticide
CN109415370A (en) * 2016-07-01 2019-03-01 日本农药株式会社 N- alkyl sulphonyl fused heterocyclic compound or its esters and insecticide and its application method containing the compound
CN109415370B (en) * 2016-07-01 2021-06-08 日本农药株式会社 N-alkylsulfonyl fused heterocyclic compound or salt thereof, insecticide containing the compound, and method of using the same
US10561145B2 (en) 2016-07-19 2020-02-18 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2018015289A1 (en) 2016-07-19 2018-01-25 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
US10660334B2 (en) 2016-08-15 2020-05-26 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2018033455A1 (en) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2018041729A2 (en) 2016-09-01 2018-03-08 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
US10611779B2 (en) 2016-09-19 2020-04-07 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2018050825A1 (en) 2016-09-19 2018-03-22 Bayer Cropscience Aktiengesellschaft Pyrazolo [1,5-a]pyridine derivatives and their use as pesticides
WO2018065292A1 (en) 2016-10-06 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed bicyclic heterocycle derivatives as pest control agents
US11339155B2 (en) 2016-10-06 2022-05-24 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
WO2018065288A1 (en) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-[2-phenyl-1-(sulfonyl-methyl)-vinyl]-imidazo-[4,5-b] pyridine derivatives and related compounds as pesticides in plant protection
US10927106B2 (en) 2016-10-12 2021-02-23 Pharmasum Therapeutics As Benzothiazole derivatives as DYRK1 inhibitors
WO2018070502A1 (en) 2016-10-13 2018-04-19 日本農薬株式会社 1h-pyrrolopyridine compound, n-oxide of same, salt of same, pesticide for agricultural and horticultural use containing said compound, and method for using same
WO2018070503A1 (en) 2016-10-13 2018-04-19 日本農薬株式会社 1h-pyrrolopyridine compound or n-oxide or salt thereof, agricultural and horticultural insecticide containing said compound, and method of using said insecticide
KR20190047067A (en) 2016-10-13 2019-05-07 니혼노야쿠가부시키가이샤 1H-pyrrolopyridine compound, or an N-oxide thereof, or a salt thereof, and an agricultural pesticide containing the compound and a method of using the same
US10779537B2 (en) 2016-10-13 2020-09-22 Nihon Nohyaku Co., Ltd. 1H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
US11124507B2 (en) 2016-10-13 2021-09-21 Nihon Nohyaku Co., Ltd. 1H-pyrrolopyridine compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
WO2018077565A1 (en) 2016-10-27 2018-05-03 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur and hydroxylamine substituents
US10435411B2 (en) 2016-11-01 2019-10-08 Nihon Nohyaku Co., Ltd. Oxime group-containing quinoline compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
US10716306B2 (en) 2016-11-01 2020-07-21 Nihon Nohyaku Co., Ltd. N-alkylsulfonyl indoline compound, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
EP3536688A4 (en) * 2016-11-01 2020-07-01 Nihon Nohyaku Co., Ltd. Quinoline compound having oxime group, n-oxide or salt thereof, agricultural and horticultural insecticide comprising same and method for use thereof
WO2018084141A1 (en) 2016-11-01 2018-05-11 日本農薬株式会社 N-alkylsulfonylindoline compound, agricultural and horticultural insecticide comprising same and method for use thereof
WO2018084142A1 (en) 2016-11-01 2018-05-11 日本農薬株式会社 Quinoline compound having oxime group, n-oxide or salt thereof, agricultural and horticultural insecticide comprising same and method for use thereof
WO2018091389A1 (en) 2016-11-17 2018-05-24 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
WO2018099812A1 (en) 2016-12-01 2018-06-07 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018108726A1 (en) 2016-12-15 2018-06-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11083198B2 (en) 2016-12-27 2021-08-10 Nihon Nohyaku Co., Ltd. 4H-pyrrolopyridine compound or salt thereof, agricultural and horticultural insecticide comprising the compound or the salt, and method for using the insecticide
WO2018124128A1 (en) 2016-12-27 2018-07-05 日本農薬株式会社 4h-pyrrolopyridine compound or salts thereof, agricultural/horticultural insecticide containing said compound, and method for using same
KR20190090006A (en) 2016-12-27 2019-07-31 니혼노야쿠가부시키가이샤 4H-pyrrolopyridine compound, or a salt thereof, and an insecticide for agricultural use containing the compound and a method for using the same
EP3564241A4 (en) * 2016-12-27 2020-12-30 Nihon Nohyaku Co., Ltd. 4h-pyrrolopyridine compound or salts thereof, agricultural/horticultural insecticide containing said compound, and method for using same
WO2018130437A1 (en) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
US11058115B2 (en) 2017-01-10 2021-07-13 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
US11083199B2 (en) 2017-01-10 2021-08-10 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2018130443A1 (en) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2018139436A1 (en) 2017-01-24 2018-08-02 住友化学株式会社 Fused heterocyclic compound and composition containing same
WO2018138050A1 (en) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Condensed bicyclic heterocyclene derivatives as pest control agents
US10772332B2 (en) 2017-02-06 2020-09-15 Bayer Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
WO2018141954A1 (en) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Aryl or heteroaryl-substituted imidazo pyridine derivatives and their use as pesticides
US11072609B2 (en) 2017-02-06 2021-07-27 Bayer Aktiengesellschaft Method for preparing halogenated imidazopyridine derivatives
WO2018141955A1 (en) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Process for preparing halogenated imidazopyridine derivatives
WO2018153778A1 (en) 2017-02-21 2018-08-30 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
JPWO2018174170A1 (en) * 2017-03-23 2020-01-23 住友化学株式会社 Condensed heterocyclic compound and composition containing the same
US10934287B2 (en) 2017-03-23 2021-03-02 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
JP7050752B2 (en) 2017-03-23 2022-04-08 住友化学株式会社 Condensed heterocyclic compound and composition containing it
WO2018174170A1 (en) 2017-03-23 2018-09-27 住友化学株式会社 Fused heterocyclic compound and composition containing same
EP3604300A4 (en) * 2017-03-23 2020-12-16 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
WO2018197257A1 (en) 2017-04-24 2018-11-01 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic-compound derivatives as pest control agents
WO2018197315A1 (en) 2017-04-25 2018-11-01 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018202540A1 (en) 2017-05-02 2018-11-08 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2018215304A1 (en) 2017-05-22 2018-11-29 Syngenta Participations Ag Tetracyclic pyridazine sulphur containing compounds and their use as pesticides
KR20200011946A (en) 2017-06-01 2020-02-04 수미토모 케미칼 컴퍼니 리미티드 Heterocyclic Compounds and Compositions Containing the Same
WO2018221720A1 (en) 2017-06-01 2018-12-06 住友化学株式会社 Heterocyclic compound and composition containing same
US11344029B2 (en) 2017-06-01 2022-05-31 Sumitomo Chemical Company, Limited Heterocyclic compound and composition containing same
WO2019008072A1 (en) 2017-07-05 2019-01-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11399542B2 (en) 2017-07-05 2022-08-02 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019008115A1 (en) 2017-07-07 2019-01-10 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019013273A1 (en) 2017-07-13 2019-01-17 住友化学株式会社 Heterocyclic compound and harmful-arthropod control agent containing same
US11203590B2 (en) 2017-07-13 2021-12-21 Sumitomo Chemical Company, Limited Heterocyclic compound and harmful-arthropod control agent containing same
US11413291B2 (en) 2017-09-18 2022-08-16 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019053182A1 (en) 2017-09-18 2019-03-21 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019059244A1 (en) 2017-09-21 2019-03-28 日本農薬株式会社 Benzimidazole compound having cyclopropylpyridyl group or salt thereof, agricultural and horticultural pesticide containing said compound, and method of using said pesticide
WO2019068572A1 (en) 2017-10-04 2019-04-11 Bayer Aktiengesellschaft Derivatives of heterocyclic compounds as pest control agents
WO2019076778A1 (en) 2017-10-16 2019-04-25 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur and sulfonimidamides containing substituents
US11555035B2 (en) 2017-12-22 2023-01-17 Sumitomo Chemical Company, Limited Heterocyclic compound and harmful arthropod-controlling agent containing same
EP3730493A4 (en) * 2017-12-22 2021-08-04 Sumitomo Chemical Company Limited Heterocyclic compound and harmful arthropod-controlling agent containing same
WO2019124529A1 (en) 2017-12-22 2019-06-27 住友化学株式会社 Heterocyclic compound and harmful arthropod-controlling agent containing same
EP3733672B1 (en) 2017-12-25 2023-03-22 Sumitomo Chemical Company, Limited Heterocyclic compounds and noxious arthropod control agent containing same
EP3305786A2 (en) 2018-01-22 2018-04-11 Bayer CropScience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pesticides
US11019821B2 (en) 2018-02-21 2021-06-01 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2019162174A1 (en) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2019168140A1 (en) 2018-03-02 2019-09-06 日本農薬株式会社 Amide compound or salt thereof, and agricultural and horticultural microbicide containing said compound, and method of using same
WO2019175045A1 (en) 2018-03-12 2019-09-19 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2019175046A1 (en) 2018-03-12 2019-09-19 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2019201921A1 (en) 2018-04-20 2019-10-24 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
KR20210014651A (en) 2018-05-22 2021-02-09 니혼노야쿠가부시키가이샤 Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal mite containing the compound, and method of using the same
US11311013B2 (en) 2018-05-22 2022-04-26 Nihon Nohyaku Co., Ltd. Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent containing said compound, and method for using same
WO2019225663A1 (en) 2018-05-22 2019-11-28 日本農薬株式会社 Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent containing said compound, and method for using same
WO2019229088A1 (en) 2018-05-30 2019-12-05 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019229089A1 (en) 2018-05-31 2019-12-05 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2019234160A1 (en) 2018-06-06 2019-12-12 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
US11926623B2 (en) 2018-06-26 2024-03-12 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2020053282A1 (en) 2018-09-13 2020-03-19 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2020084075A1 (en) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
WO2020141136A1 (en) 2018-12-31 2020-07-09 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020173861A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
WO2020173860A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
US20220061325A1 (en) * 2019-02-26 2022-03-03 Nippon Soda Co., Ltd. Pyridine n-oxide compound and pest control agent
WO2020174094A1 (en) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020174096A1 (en) 2019-02-28 2020-09-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020178789A1 (en) 2019-03-07 2020-09-10 Pi Industries Ltd. Fused heterocyclic compounds and their use as pest control agents
WO2020182577A1 (en) 2019-03-08 2020-09-17 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2020188014A1 (en) 2019-03-20 2020-09-24 Syngenta Crop Protection Ag Pesticidally active azole amide compounds
WO2020250183A1 (en) 2019-06-13 2020-12-17 Pi Industries Ltd. Fused heterocyclic compounds and their use as pest control agents
WO2020254530A1 (en) 2019-06-18 2020-12-24 Syngenta Crop Protection Ag 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide derivatives and the respective -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoline-2-, and -naphthalene-2-carboxamide derivatives as pesticides
WO2021053110A1 (en) 2019-09-20 2021-03-25 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur and sulfoximine containing substituents
WO2021107110A1 (en) 2019-11-28 2021-06-03 日本農薬株式会社 Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent comprising said compound, and method for using said insecticidal and acaricidal agent
KR20220108788A (en) 2019-11-28 2022-08-03 니혼노야쿠가부시키가이샤 Benzimidazole compound or salts thereof, agricultural and horticultural insecticidal acaricides containing the compound, and methods of using the same
WO2021136722A1 (en) 2019-12-31 2021-07-08 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2021140122A1 (en) 2020-01-06 2021-07-15 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2021204589A1 (en) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
WO2021213929A1 (en) 2020-04-20 2021-10-28 Syngenta Crop Protection Ag Pesticidally active substituted 1,3-dihydro-2h-imidazo[4,5-c]pyridin-2-one derivatives with sulfur containing substituents
WO2021213978A1 (en) 2020-04-21 2021-10-28 Bayer Aktiengesellschaft 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents
WO2021219810A1 (en) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2021224409A1 (en) 2020-05-06 2021-11-11 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022002818A1 (en) 2020-07-02 2022-01-06 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
WO2022013417A1 (en) 2020-07-17 2022-01-20 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022017975A1 (en) 2020-07-18 2022-01-27 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022043576A2 (en) 2020-08-31 2022-03-03 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049141A1 (en) 2020-09-01 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049146A1 (en) 2020-09-02 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022049144A1 (en) 2020-09-02 2022-03-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022053567A1 (en) 2020-09-09 2022-03-17 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022157334A1 (en) 2021-01-21 2022-07-28 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2022238391A1 (en) 2021-05-12 2022-11-17 Bayer Aktiengesellschaft 2-(het)aryl-substituted condensed heterocycle derivatives as pest control agents
WO2023017094A1 (en) 2021-08-10 2023-02-16 Syngenta Crop Protection Ag 2,2-difluoro-5h-[1,3]dioxolo[4,5-f]isoindol-7-one derivatives as pesticides
WO2023036706A1 (en) 2021-09-07 2023-03-16 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
WO2023036707A1 (en) 2021-09-07 2023-03-16 Bayer Aktiengesellschaft Substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, salts thereof and their use as herbicidally active substances
WO2023072945A1 (en) 2021-10-25 2023-05-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023148369A1 (en) 2022-02-07 2023-08-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023148368A1 (en) 2022-02-07 2023-08-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2023187191A1 (en) 2022-04-01 2023-10-05 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024089023A1 (en) 2022-10-25 2024-05-02 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024094575A1 (en) 2022-10-31 2024-05-10 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024126388A1 (en) 2022-12-12 2024-06-20 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024156664A1 (en) 2023-01-23 2024-08-02 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents
WO2024189139A1 (en) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Control of pests resistant to insecticides

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