WO2014007395A1 - Pyrazole or thiazole derivative, salt thereof, and pest control agent - Google Patents

Pyrazole or thiazole derivative, salt thereof, and pest control agent Download PDF

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Publication number
WO2014007395A1
WO2014007395A1 PCT/JP2013/068656 JP2013068656W WO2014007395A1 WO 2014007395 A1 WO2014007395 A1 WO 2014007395A1 JP 2013068656 W JP2013068656 W JP 2013068656W WO 2014007395 A1 WO2014007395 A1 WO 2014007395A1
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alkyl
optionally substituted
phenyl
substituted
cycloalkyl
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PCT/JP2013/068656
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French (fr)
Japanese (ja)
Inventor
沼田　昭
裕二 岩脇
前田　兼成
裕貴 古川
史代 齊藤
佑介 南條
公則 安藤
Original Assignee
日産化学工業株式会社
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Priority claimed from JP2012285648A external-priority patent/JP2015164898A/en
Priority claimed from JP2013122681A external-priority patent/JP2015164899A/en
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2014007395A1 publication Critical patent/WO2014007395A1/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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • 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
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to a novel pyrazole or thiazole derivative or a salt thereof, and a pest control agent characterized by containing the compound as an active ingredient.
  • the pest control agent in the present invention refers to the field of agriculture and horticulture or the field of livestock and hygiene (endoparasites / external parasites for mammals or birds as domestic animals and pets, hygiene pests and unpleasant pests for household and commercial use) It means a pest control agent for harmful arthropods such as
  • the agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.
  • Patent Documents 1 to 9 and Patent Documents 13 to 14 disclose pyrazole and thiazole derivatives, but do not disclose any pyrazole and thiazole derivatives according to the present invention. Furthermore, its usefulness as a pest control agent, particularly an insecticide / acaricide, and an internal or ectoparasite control agent for mammals or birds is not known at all.
  • Patent Documents 10 to 12 disclose that pyrazole and thiazole derivatives are useful as insecticides, but do not disclose any pyrazole and thiazole compounds according to the present invention.
  • An object of the present invention is to provide a novel pesticide having high activity, low toxicity, and low persistence.
  • the present inventors have found that the novel pyrazole and thiazole derivatives represented by the following formula (1) according to the present invention have excellent pest control activity, particularly insecticide /
  • the present invention was completed by discovering that it is a very useful compound that exhibits acaricidal activity and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects. That is, the present invention relates to the following [1] to [104].
  • a 1 is, -N (-O) m2 or represents -CR 1
  • R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 3 -C 8 cycloalkyl , optionally substituted with R 28a (C 3 ⁇ C 8 ) cycloalkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 28a (C 2 ⁇ C 6 ) alkenyl, C 3 ⁇ C 8 cycloalkyl
  • R 2 represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S ( O) 2 NH 2, C 1 ⁇ C 6 alkyl, substituted optionally substituted with R 28a (C 1 ⁇ C 6 ) alkyl, C 3 ⁇ C 8 cycloalkyl, optionally with R 28a (C 3 ⁇ C 8) cycloalkyl, C 2 ⁇ C 6 alkenyl, which is optionally substituted with R 28a (C 2 ⁇ C 6 ) alkenyl, C 3 ⁇ C 8 cycloalkenyl, which is optionally substituted with R 28a (C 3 ⁇ C 8 ) cycloalkenyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 28a
  • B represents a ring represented by either B-1 or B-2.
  • “*” represents the bonding position with the substituent “—N (R a ) R b ”, and “**” represents the bonding position with the substituent shown below.
  • R a is a hydrogen atom, C 1 ⁇ C 6 alkyl, optionally substituted with R 5a (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 5a (C 2 ⁇ C 6) alkenyl, C 2 ⁇ C 6 alkynyl, optionally substituted with R 5a (C 2 ⁇ C 6 ) alkynyl, C 3 ⁇ C 8 cycloalkyl, optionally substituted with R 5a (C 3 ⁇ C 8 ) Cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 5a , —OR 6a , —S (O) r 2 R 6a , —C (O) OR 6a , -C (O) SR6a , -C (S) OR6a , -C (S) SR6a , -C
  • the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is a halogen atom, cyano, nitro, C 1 -C 6 alkyl, —OH, —OR 11a , -SH, S (O) r R 11a, which may be optionally substituted by oxo or thioxo group.
  • R 6a , R 8a and R 9a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 10a , C 2 -C 6 alkenyl, R 10a in optionally substituted (C 2 ⁇ C 6) alkenyl, C 2 ⁇ C 6 alkynyl, optionally substituted with R 10a (C 2 ⁇ C 6) alkynyl, C 3 ⁇ C 8 cycloalkyl, with R 10a Optionally substituted (C 3 -C 8 ) cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 10a , —S (O) r2 R 11a , -C (O) OR 11a , -C (O) SR 11a , -C (S) OR 11a , -C (S) SR 11a
  • R 10a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 11a , —SH, —S (O) r 2 R 11a
  • R 11a and R 12a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkenyl, optionally with R 15a substituted (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, optionally substituted with R 15a (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15a Substituted (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15a , —S (O) r 2 R 16a , —C ( O) OR 16a , -C (O) SR 16a , -C (S) OR 16a , -C (S) SR 16a
  • R 11b is substituted C 1 ⁇ C 10 alkyl, optionally with R 15b (C 1 ⁇ C 6 ) alkyl, optionally substituted with C 2 ⁇ C 6 alkenyl, R 15b (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ⁇ C 8 ) cycloalkenyl, optionally substituted with C 2 ⁇ C 6 alkynyl, R 15b (C 2 ⁇ C 6) Alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r 3 R 16b , —C (O) OR 16b , —C (O) SR 16b , -C (S) OR 16b , -C (S) SR 16b , -C (O) R 17b , -C (S
  • R 12b is a hydrogen atom, a halogen atom, substituted cyano, C 1 ⁇ C 6 alkyl, optionally substituted with R 15c (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, the R 15c optionally (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15c (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , -C (O) SR 16c , -C (S) OR 16c , -
  • R 13a and R 14a each independently represent a hydrogen atom or C 1 -C 6 alkyl, or R 13a together with R 14a is a C 2 -C 7 alkylene chain or C 2 -C 7. To form a 3- to 8-membered ring together with the nitrogen atom to which R 13a and R 14a are bonded.
  • the alkylene chain or alkenylene chain has an oxygen atom, a sulfur atom or a nitrogen atom.
  • One may be included, and optionally substituted by a (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 15a .
  • R 13b is a hydrogen atom, cyano, substituted nitro, C 1 ⁇ C 6 alkyl, optionally substituted with R 15b (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally with R 15b (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, substituted is optionally substituted with R 15b (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15b (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —OR 16b , —S (O) r3 R 16b , —C (O) OR 16b , -C (O) SR 16b , -C (S) OR 16b , -C (S)
  • the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with R 42 or R 15b (C 1 ⁇ C 6 Alkyl may be optionally substituted by oxo or thioxo group.
  • R 14b is a hydrogen atom, cyano, substituted nitro, C 1 ⁇ C 6 alkyl, optionally substituted with R 15d (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally with R 15d (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, substituted is optionally substituted with R 15d (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15d (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15d , —OR 16d , —S (O) r3 R 16d , —C (O) OR 16d , -C (O) SR 16d , -C (S) OR 16d , -C (S)
  • R 14e and R 14f are each independently a hydrogen atom, cyano, nitro, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, R optionally substituted with 15b (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, R optionally substituted with 15b (C 2 ⁇ C 6) alkynyl, C 3 ⁇ C 8 cycloalkyl, optionally substituted with R 15b (C 3 ⁇ C 8 ) cycloalkyl, -OR 16b, -S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (S) OR 16b, -C (S
  • a 3- to 8-membered ring may be formed together with the carbon atom, and this alkylene chain or alkenylene chain may contain 1, 2 or 3 oxygen atoms, sulfur atoms or nitrogen atoms, and R 42 , R 15b At Substituted in (C 1 ⁇ C 6) alkyl, it may be optionally substituted by oxo or thioxo group.
  • R 15a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16a , —SH, —S (O) r 2 R 16a , —S ( ⁇ NR 18a ) R 16a , —S (O) ( ⁇ NR 18a ) R 16a , —P (O) (OR 41 ) 2 , —P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15a is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylim
  • R 18a and R 19a each independently represents a hydrogen atom, cyano or C 1 -C 6 alkyl
  • R 18b , R 19b , R 18d and R 19d are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl , C 3 ⁇ C 8 cycloalkenyl, optionally substituted optionally substituted with R 20 (C 1 ⁇ C 6 ) alkyl, optionally substituted with R 20 (C 2 ⁇ C 6 ) alkenyl, optionally with R 20 and (C 2 ⁇ C 6) alkynyl, optionally substituted with R 20 (C 3 ⁇ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ⁇ C 8 ) cycloalkenyl, phenyl, (Z ) Phenyl substituted by q ,
  • the alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 20 May be.
  • R 18c and R 19c are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , —OR 21 , —S (O) r R 21 , —C (O) OR 21 , —C (O) R 22 , —C (S) R 22 , phenyl or phenyl substituted by (Z) q ;
  • R 20 is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, —C (O) OR 21 , phenyl or phenyl substituted by (Z) q , or when two R 20 are
  • X 1 and X 1b are each independently a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S ) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl C 3 -C 8 cycloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 ⁇ C 6 alkylthio, C 1 ⁇ C 6 haloalkylthio, C 1 ⁇ C 6
  • X 1a is a hydrogen atom, cyano, —OH, —NH 2 , —CHO, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl.
  • adjacent X 1a and X 1 are —CH 2 CH 2 CH 2 CH 2 —, —CH ⁇ CHCH ⁇ CH—, —N ⁇ CHCH ⁇ CH— , —CH ⁇ N—CH ⁇ CH—, —CH ⁇ CH—N ⁇ CH—, or —CH ⁇ CH—CH ⁇ N— to form a six-membered atom together with the atoms to which each of X 1a and X 1 is attached.
  • a hydrogen atom bonded to each carbon atom forming the ring may be a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 It may be optionally substituted with a 1 to C 6 alkoxy group, a C 1 to C 6 alkylthio group, a C 1 to C 6 alkylsulfinyl group or a C 1 to C 6 alkylsulfonyl group.
  • Z represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O ) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl optionally substituted with R 28 , C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfiny
  • each Z may be the same as or different from each other.
  • the hydrogen atom bonded to the carbon atom is a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group, C 1 it may be optionally substituted by ⁇ C 6 alkylsulfinyl group or a C 1 ⁇ C 6 alkylsulfonyl group.
  • R 28 , R 28a , R 31 and R 32 are each independently a halogen atom, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2, -S ( O) 2 NH 2, -Si (R 40a) (R 40b) R 40, C 1 ⁇ C 6 alkoxy, C 1 ⁇ C 6 haloalkoxy, C 1 ⁇ C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6
  • R 29 and R 29a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 31 (C 1 -C 6 ) alkyl optionally substituted with R 31 , (C 2 -C 6 ) alkenyl optionally substituted with R 31 , (C 2 -C 6 ) alkynyl optionally substituted with R 31 , R optionally substituted with 31 representing the (C 3 ⁇ C 8) optionally substituted cycloalkyl, or R 31 (C 3 ⁇ C 8 ) cycloalkenyl.
  • R 30 and R 30a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 32 (C 1 -C 6 ) alkyl optionally substituted with R 32 , (C 2 -C 6 ) alkenyl optionally substituted with R 32 , (C 2 -C 6 ) alkynyl optionally substituted with R 32 , R optionally substituted with 32 (C 3 ⁇ C 8) cycloalkyl, optionally substituted with R 32 (C 3 ⁇ C 8 ) cycloalkenyl, phenyl, phenyl optionally substituted with C 1 ⁇ C 6 alkyl Alternatively, it represents phenyl optionally substituted with a halogen atom.
  • R 40, R 40a and R 40b are each independently C 1 to ⁇ C 6 alkyl, C 1 ⁇ C 6 alkoxy or phenyl, R 41 represents C 1 -C 6 alkyl, R 42 represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C Represents 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, phenyl or phenyl substituted by (Z) q .
  • g1, f1 and n each independently represent an integer of 0, 1, 2 or 3; g2 and f2 each independently represent an integer of 0, 1 or 2; g3 represents an integer of 0 or 1, g4 and f4 each independently represent an integer of 0, 1, 2, 3 or 4; f5 represents an integer of 0, 1, 2, 3, 4 or 5, f6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, f8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8; f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, q represents an integer of 1, 2, 3, 4 or 5; m1, m2 and m3 each independently represent an integer of 0 or 1, r, r2 and r3 each independently represents an integer of 0, 1 or 2. ]
  • a 1 represents -CR 1 R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 2 -C 6 alkynyl , (C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl optionally substituted with R 28a , R 2 represents a halogen atom or C 1 -C 6 alkyl, B is a pyrazole derivative or a salt thereof according to the above [1], wherein B represents B-1.
  • a 1 represents -N (-O) m2
  • B represents B-1
  • R 3 and R 4 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl
  • R 2 represents a halogen atom or C 1 -C 6 alkyl
  • B is a pyrazole derivative or a salt thereof according to the above [1], wherein B represents B-1.
  • B represents B-2
  • R 12b is a hydrogen atom, cyano, C 1 ⁇ C 6 alkyl, optionally substituted with R 15c (C 1 ⁇ C 6 ) alkyl, substituted C 2 ⁇ C 6 alkenyl, the R 15c optionally (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15c (C 2 —C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , —C (O) SR 16c , —C (S) OR 16c , —C (
  • R 1 represents a hydrogen atom or a halogen atom
  • R 2 represents a halogen atom
  • R 3 represents a hydrogen atom, a halogen atom, substituted C 1 ⁇ C 6 alkyl, optionally substituted with R 28a (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkynyl, optionally with R 28a ( C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl
  • R 4 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl
  • R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl
  • —S (O) represents an r2 R 6a, -C (O) oR 6a, -C (O)
  • R 10a represents —OR 11a or —S (O) r2 R 11a ;
  • R 11a is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkynyl, -C (O) OR 16a , -C (O) R 17a , —C (O) N (R 18a ) R 19a or —Si (R 40a ) (R 40b ) R 40
  • R 11b is C 1 -C 7 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted with R 15b , -C (O) OR 16b or Represents -C (O) R 17b
  • R 12a represents (C 1 -C 6 ) alkyl optionally substituted with R 15a
  • R 12b is a hydrogen atom,
  • R 13a and R 14a each independently represents a hydrogen atom or C 1 -C 6 alkyl;
  • R 15a represents —OR 16a , —S (O) r2 R 16a , phenyl or —Si (R 40a ) (R 40b ) R 40 ,
  • R 15b is a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 16b , —S (O) r3 R 16b , —C (O) OH, —C (O) OR 16b , —C (O) represents N (R 18b ) R 19b , —C ( ⁇ NOR 16b ) R 17b , (Z) q , phenyl substituted by q , D1-33 or D1-84,
  • R 15c represents a halogen atom, cyano, —OH, —OR 16c , —S (O) r R 16
  • R 16c is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , -S (O) r R 21 , (Z) represents phenyl or D1-32 substituted by q ;
  • R 17a represents C 1 -C 6 alkyl or phenyl;
  • R 17b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
  • R 17c represents C 1 -C 6 alkyl;
  • R 18a and R 19a each independently represent C 1 -C 6 alkyl;
  • R 18b represents a hydrogen atom, or R 18b together with R 19b forms a C 5 alkylene chain to form a 6-membered ring with the nitrogen atom to which R 18b and R 19b are
  • the alkylene chain may contain one oxygen atom
  • R 18c represents C 1 -C 6 alkyl or —C (O) R 22
  • R 19b represents (C 1 -C 6 ) alkyl optionally substituted with R 20
  • R 19c represents a hydrogen atom
  • R 20 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio
  • R 21 represents phenyl substituted by (Z) q
  • R 22 represents C 1 -C 6 alkyl
  • R 23 and R 24 represent a hydrogen atom
  • X 1 represents a halogen atom or (C 1 -C 6 ) alkyl optionally substituted with R 28
  • R 28 represents a halogen atom
  • R 28a represents a halogen atom or —Si (R 40a ) (R 40b ) R 40
  • Z represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio
  • R 40 , R 40a and R 40b each independently represent C 1 -C 6 alkyl.
  • g1, g4, m1 and n each independently represent an integer of 0 or 1, f5, f7 and m3 represent 0; q represents an integer of 1; r and r3 each independently represents an integer of 0, 1 or 2; r2 represents 0 or an integer of 2; the pyrazole derivative or the salt thereof according to [2] above.
  • a 1 represents -CR 1 R 1 and R 3 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl;
  • R 2 represents a halogen atom or C 1 -C 6 alkyl,
  • R 12b is a hydrogen atom, cyano, C 1 ⁇ C 6 alkyl, optionally substituted with R 15c (C 1 ⁇ C 6 ) alkyl, substituted C 2 ⁇ C 6 alkenyl, the R 15c optionally (C 2 ⁇ C 6) alkenyl, C 3 ⁇ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ⁇ C 8 ) cycloalkenyl, C 2 ⁇ C 6 alkynyl, optionally with R 15c (C 2 The thiazole derivative or a salt thereof according to the above [4], which represents (C 3 -C 8 ) cycloalkyl optionally substituted with —C 6 ) alkyny
  • R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) OR 6a , —C (O) R 7a , —C (O) N (R 8a ) R 9a or —C (S) N (R 8a ) R 9a , or R a together with R 3 And forming a C 2 -C 4 alkylene chain to form a 5- to 7-membered ring together with the nitrogen atom to which R a is bonded and the carbon atom to which R 3 is bonded, R b represents —C (O) R 7b or —C (S) R 7b ; R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S
  • R 11b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted with R 15b
  • R 12b is a hydrogen atom, C 1 ⁇ C 6 alkyl, optionally substituted with R 15c (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 15c (C 2 ⁇ C 6 ) alkenyl, C 2 -C 6 alkynyl or (C 2 -C 6 ) alkynyl optionally substituted with R 15c
  • R 13b and R 14b are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 Cycloalkyl, —S (O) r3 R 16b ,
  • R 15b represents a halogen atom or cyano
  • R 15c represents —OH, —OR 16c , —SH, —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98
  • R 16a and R 17a each independently represent C 1 -C 6 alkyl
  • R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl or (C 1 -C 6 ) alkyl optionally substituted with R 20
  • R 16c is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, Phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38, each
  • R 20 represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or phenyl
  • X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28
  • R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio
  • Z represents a halogen atom, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio, the thiazole derivative according to the above [6] Or a salt thereof.
  • R 1 represents a hydrogen atom
  • R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl
  • R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 to C 6 alkynyl or —C (O) OR 6a , or R a together with R 3 forms a C 3 alkylene chain to form a nitrogen atom to which R a is attached and R 3 May form a 6-membered ring with the carbon atom to which R b represents —C (O) R 7b ;
  • R 5a represents C 3 -C 8 cycloalkyl or —OR 11a
  • R 6a represents C 1 -C 6 alkyl
  • R 11a represents C 1 -C 6 alkyl or —C (O) R 17a
  • R 11b represents C 1 -C 6 alkyl or (C 1 -C
  • R 15c represents —OR 16c , —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98;
  • R 16b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
  • R 16c is, C 1 ⁇ C 6 alkyl, optionally substituted with R 20 (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, C 3 ⁇ C 8 cycloalkyl, substituted by (Z) q Represents phenyl or D1-32.
  • R 17a represents C 1 -C 6 alkyl
  • R 17b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 3 -C 8 cycloalkyl or phenyl
  • R 18b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, phenyl or phenyl substituted by (Z) q
  • R 19b represents a hydrogen atom.
  • R 20 represents a halogen atom, cyano, C 1 -C 6 alkoxy or phenyl
  • X 1 represents (C 1 -C 6 ) alkyl optionally substituted with R 28
  • R 28 represents a halogen atom
  • Z represents a halogen atom, nitro or C 1 -C 6 alkoxy
  • g1 and g4 represent an integer of 1
  • f5, f7, m1, m3 and n represent 0
  • q represents an integer of 1 or 2
  • r is a thiazole derivative or a salt thereof according to the above [7], wherein r represents an integer of 0, 1 or 2.
  • R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) Represents OR 6a or —C (O) R 7a , R b represents —C (O) R 7b or —C (S) R 7b ; R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S (O) r2 R 11a , R 6a represents C 1 -C 6 alkyl; R 7a represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl, R 11a represents C 1 -C 6 alkyl, —C (O) OR 16a or —C (O) R 17a , R 12b is a hydrogen atom, C
  • R 13b is a hydrogen atom, C 1 ⁇ C 6 alkyl, optionally substituted with R 15b (C 1 ⁇ C 6 ) alkyl, C 2 ⁇ C 6 alkenyl, optionally substituted with R 15b (C 2 ⁇ C 6 ) alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r3 R 16b , —C ( O) OR 16b , —C (S) OR 16b , —C (O) SR 16b , —C (S) SR 16b , —C (O) R 17b , —C (S) R 17b , —C (O) N (R 18b ) R 19b , —C (S) N (R 18b ) R 19b , —C (S) N (R 18b
  • X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28
  • R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio
  • Z is a halogen atom, nitro, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C The pyrazole derivative or the salt thereof according to the above [9], which represents 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio or C 1 to C 6 haloalkylthio.
  • R 1 represents a hydrogen atom
  • R 2 represents a halogen atom
  • R 4 represents a hydrogen atom or C 1 -C 6 alkyl
  • R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl
  • R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a or —C (O) R 7a
  • R 5a represents -OR 11a
  • R 7a represents C 3 -C 8 cycloalkyl
  • R 11a represents C 1 -C 6 alkyl
  • R 12b represents a hydrogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 15c .
  • R 13b is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, —S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (O) R 17b, -C (O) N (R 18b) R 19b, -C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32 or D1-37, or R 13b together with R 14b forms a C 4 alkylene chain , R 13b and R 14b may form a 5-membered ring with the nitrogen atom to which they are bonded, R 14b represents a hydrogen atom or C 1 -C 6 alkyl, or R 14b together with R 13b may form
  • R 14e represents C 1 -C 6 alkyl or —OR 16b
  • R 14f represents a hydrogen atom or C 1 -C 6 alkyl
  • R 15b represents a halogen atom
  • R 15c represents -S (O) r R 16c
  • R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, (C 1 -C 6 ) alkyl or phenyl optionally substituted with R 20
  • R 16c represents C 1 -C 6 alkyl
  • R 17b is optionally substituted with a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 20 (C 1 -C 6 ) alkyl, —C (O) R 22 , —C ( ⁇ NOR 21 ) R 22 , pheny
  • R 19b represents a hydrogen atom
  • R 20 represents cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, -C (O) OR 21 or phenyl
  • R 21 represents C 1 -C 6 alkyl
  • R 22 represents a hydrogen atom or C 1 -C 6 alkyl
  • R 28 represents a halogen atom
  • Z represents a halogen atom, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio
  • g1, g4 and m3 represent 0
  • n represents an integer of 0 or 1
  • q represents an integer of 1 or 2
  • r3 is the pyrazole derivative or the salt
  • a 1 represents -CR 1 R 1 and R 4 represent a hydrogen atom, The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein n and m1 represent 0.
  • a 1 represents -CR 1 R 1 represents a halogen atom, The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein n and m1 represent 0.
  • a 1 represents -CR 1 R 1 represents a hydrogen atom, R 2 represents a halogen atom, n represents an integer of 1; The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein m1 represents 0.
  • R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl.
  • R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], in which R 3 represents a hydrogen atom.
  • R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents a halogen atom or C 1 -C 6 alkyl.
  • R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], which represents a halogen atom.
  • R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], in which R 3 represents a chlorine atom.
  • R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents C 1 -C 6 alkyl.
  • R 3 represents methyl.
  • R a represents (C 1 -C 6 ) alkyl, —C (O) N (R 8a ) R 9a or —C (S) N (R 8a ) R 9a optionally substituted with R 5a
  • R 5a represents —OR 11a or —C (O) OH
  • R 8a represents a hydrogen atom
  • R 9a represents C 1 -C 6 alkyl
  • R 11a represents —C (O) OR 16a , —C (O) R 17a or —C (O) N (R 18a ) R 19a
  • R 16a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20
  • R 17a represents C 1 -C 6 alkyl or phenyl
  • R 18a and R 19a each independently represent C 1 -C 6 alkyl
  • R 20 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1
  • R a represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [22] above.
  • R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 1 -C 6 alkyl.
  • R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 2 -C 6 alkenyl.
  • R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 2 -C 6 alkynyl.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a , R 5a represents cyano, C 3 -C 8 cycloalkyl, —OH or —OR 11a
  • R 11a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 11a represents C 1 -C 6 alkyl or C 2 -C 6 alkynyl.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a
  • R 5a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which R 5a represents cyano.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a , R 5a is, pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [22] representing the C 3 - C 8 cycloalkyl.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a , R 5a represents -OR 11a ;
  • R 11a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which R 11a represents C 1 -C 6 alkyl.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a
  • R 5a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which —OH represents —OH.
  • R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a
  • R 5a represents -OR 11a
  • R 11a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 11a represents C 2 -C 6 alkynyl.
  • R a represents —C (O) R 7a ;
  • R 7a is a pyrazole or thiazole derivative or a salt thereof according to the above [1] to [22], wherein R 7a represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl.
  • R a represents —C (O) R 7a ;
  • R 7a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 7a represents C 1 -C 6 alkyl.
  • R a represents —C (O) R 7a ;
  • R 7a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 7a represents C 3 -C 8 cycloalkyl.
  • R a represents —C (O) OR 6a
  • R 6a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 6a represents C 1 -C 6 alkyl.
  • R b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (O) R 7b or —C (S) R 7b .
  • R b represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (O) R 7b .
  • R b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (S) R 7b .
  • R 7b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C ( ⁇ NOH) R 12b .
  • R 7b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C ( ⁇ NOR 11b ) R 12b .
  • R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 1 -C 10 alkyl or C 2 -C 6 alkenyl.
  • R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 1 -C 10 alkyl.
  • R 11b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [45] representing the C 1 ⁇ C 6 alkyl.
  • R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 11b represents methyl.
  • R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 11b represents ethyl.
  • R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 2 -C 6 alkenyl.
  • R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b
  • R 15b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 15b represents cyano or C 3 -C 8 cycloalkyl.
  • R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b , R 15b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 15b represents cyano.
  • R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b , R 15b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [45] representing the C 3 - C 8 cycloalkyl.
  • R 12b represents cyano, —C (O) OR 16c , —C (O) N (R 18c ) R 19c or —C ⁇ NN (R 18c ) R 19c ⁇ R 17c
  • R 16c represents C 1 -C 6 alkyl
  • R 17c represents C 1 -C 6 alkyl
  • R 18c represents C 1 -C 6 alkyl or —C (O) R 22
  • R 19c represents a hydrogen atom
  • R 22 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein C 22 represents C 1 -C 6 alkyl.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 12b represents a hydrogen atom or C 1 -C 6 alkyl.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ;
  • R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ; R 16c is the pyrazole or thiazole derivative or salt thereof according to any one of the above [1] to [54], wherein C 16 represents C 3 -C 8 cycloalkyl.
  • R 12b is optionally substituted with R 15c (C 2 ⁇ C 6 ) alkenyl, optionally substituted with optionally substituted with R 15c (C 2 ⁇ C 6 ) alkynyl, or R 15c (C 3 ⁇ C 8 ) represents cycloalkyl, R 15c represents -S (O) r R 16c ; R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 2 -C 6 ) alkenyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ; R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 2 -C 6 ) alkynyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ; R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ; R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c , R 15c represents -S (O) r R 16c ; R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein C 16 represents C 2 -C 6 alkenyl.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c
  • R 15c represents -S (O) r R 16c
  • R 16c represents (C 1 -C 6 ) alkyl optionally substituted with R 20
  • R 20c is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], in which R 20c represents a halogen atom.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c
  • R 15c is the pyrazole or thiazole derivative or salt thereof according to any one of the above [1] to [54], wherein D 15 represents D 1-87 or D 1-98.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c
  • R 15c represents a halogen atom or —S (O) r R 16c
  • R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c , R 15c represents cyano or —S (O) r R 16c , R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c
  • R 15c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 15c represents —OR 16c or —S (O) r R 16c .
  • R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c , R 15c represents -OR 16c or -S (O) r R 16c ; R 16c represents C 1 -C 6 alkyl or —S (O) r R 21 , R 21 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 21 represents C 1 -C 6 alkyl.
  • R 12b is phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34, and the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [54] above .
  • R 12b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein -S (O) r R 16c is represented.
  • R 12b represents -S (O) r R 16c ;
  • R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
  • R 12b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein -C (O) R 17c is represented.
  • R 12b is phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34, and the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [54] above .
  • R 13b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [92], in which R 13b represents a hydrogen atom.
  • R 13b represents -S (O) r3 R 16b , R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ⁇ C 6 alkyl.
  • R 13b represents -C (O) OR 16b , R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ⁇ C 6 alkyl.
  • R 13b represents -C (O) R 17b , R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ⁇ C 6 alkyl.
  • R 14b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [96], in which R 14b represents a hydrogen atom.
  • R 14b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [96], which represents the C 1 ⁇ C 6 alkyl.
  • a pest control agent comprising one or more selected from the pyrazole or thiazole derivatives or salts thereof according to any one of [1] to [98] as an active ingredient.
  • a mammal or avian internal or ectoparasite control agent comprising, as an active ingredient, one or more selected from the pyrazole or thiazole derivative according to any one of [1] to [98] or a salt thereof.
  • the soil treatment agent according to [103], wherein the soil treatment method is soil irrigation treatment.
  • the compound of the present invention has excellent insecticidal / miticidal activity against internal or ectoparasites of many agricultural pests, spider mites, mammals or birds, and has acquired resistance to existing insecticides. Exhibits a sufficient control effect. Furthermore, it has little adverse effect on mammals, fish and beneficial insects, has low persistence, and has a light environmental impact. Therefore, the present invention can provide a useful novel pest control agent.
  • the compounds encompassed by the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, but the present invention is not limited to these E-form, Z-form, or E-form. And a mixture containing Z-isomer and Z-isomer in an arbitrary ratio.
  • the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
  • those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like.
  • Salts inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, sulfonic acid salts such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, etc.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, man
  • a salt of an amino acid such as glutamic acid or aspartic acid can be used.
  • those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or an aluminum salt.
  • n- means normal
  • i- means iso
  • s- means secondary and tert- means tertiary
  • Ph means phenyl.
  • halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, for example, a methyl group, an ethyl group, an n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group and the like. Each selected range of carbon atoms is selected.
  • C a -C b haloalkyl is a linear or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom.
  • fluoromethyl group chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group
  • C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 8 members. I can do it.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Selected in a range of numbers.
  • C a -C b halocycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And can form monocyclic or complex ring structures from 3 to 8 membered rings.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Specific examples include cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, etc., each selected within the range of the designated number of carbon atoms.
  • C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule.
  • Represents a saturated hydrocarbon group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1
  • Specific examples include 1,2-dimethyl-2-propenyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b haloalkenyl is represented by a linear or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms.
  • a monocyclic or complex ring structure from a member ring to a 6-member ring can be formed.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • Specific examples include 1-cyclopenten-1-yl group, 2-cyclopenten-1-yl group, 1-cyclohexen-1-yl group, 2-cyclohexen-1-yl group, and the like. Selected in a range of numbers.
  • C a -C b alkylidene represents a linear or branched hydrocarbon group having a carbon number of a to b and bonded by a double bond, for example, a methylidene group, an ethylidene group, Specific examples include a group, a propylidene group, a 1-methylethylidene group, etc., and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkynyl represents a linear or branched chain having a carbon number of a to b and an unsaturated group having one or more triple bonds in the molecule.
  • C a -C b haloalkynyl represents a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • Specific examples include 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the like. Each of which is selected for each specified number of carbon atoms.
  • C a -C b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, such as methoxy group, ethoxy group, n-propyloxy group, Specific examples include i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 Specific examples include 1,2,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning comprising a to b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b haloalkylthio in the present specification represents a haloalkyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylthio group, trifluoromethylthio group, chlorodifluoro Methylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethylthio group, Pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio group , Nonafluorobutylthio group and the like are given as specific examples,
  • C a -C b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, Specific examples include n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. The range is selected.
  • C a -C b haloalkylsulfinyl represents a haloalkyl-S (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethylsulfinyl group, trifluoromethyl Sulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl group, nona Specific examples include a fluorobutylsulfinyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylsulfonyl in the present specification represents an alkyl-SO 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group, n- Specific examples include propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group, etc. Selected.
  • C a -C b haloalkylsulfonyl in the present specification represents a haloalkyl-SO 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethylsulfonyl group or a trifluoromethylsulfonyl group.
  • Chlorodifluoromethylsulfonyl group bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1,1,2-trimethyl
  • Specific examples include a fluoroethylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylamino group , Ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group and the like. Selected by range.
  • di (C a -C b alkyl) amino in the present specification has the above-mentioned meaning that the number of carbon atoms, which may be the same or different from each other, is ab.
  • Specific examples include an amino group, a di (n-butyl) amino group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • Specific examples include an oxyimino group, an i-propyloxyimino group, an n-butyloxyimino group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning comprising a to b carbon atoms, for example, an acetyl group, a propionyl group, a butyryl group.
  • Specific examples thereof include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like, and each is selected in the range of the designated number of carbon atoms.
  • C a -C b haloalkylcarbonyl in the present specification represents a haloalkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropanoyl group Etc.
  • a fluoroacetyl group such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacety
  • C a -C b cycloalkylcarbonyl in the present specification represents a cycloalkyl-C (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as cyclopropylcarbonyl group, 2 Specific examples include -methylcyclopropylcarbonyl group, cyclobutylcarbonyl group and the like, each selected within the range of the designated number of carbon atoms.
  • C a -C b halocycloalkylcarbonyl represents a halocycloalkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, for example 2,2- Specific examples include a dichlorocyclopropylcarbonyl group, a 2,2-dichloro-1-methylcyclopropylcarbonyl group, etc., and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Specific examples include a group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like. Selected.
  • C a -C b haloalkoxycarbonyl represents a haloalkyl-O—C (O) — group having the above-mentioned meaning of a to b carbon atoms, such as a chloromethoxycarbonyl group, Specific examples include 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, and the like. Selected in the range of the number of carbon atoms.
  • C a -C b alkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example methylcarbamoyl
  • Specific examples include a group, ethylcarbamoyl group, n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group, i-butylcarbamoyl group, s-butylcarbamoyl group, tert-butylcarbamoyl group, etc.
  • C a -C b haloalkylaminocarbonyl in this specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with a haloalkyl group as defined above consisting of a to b carbon atoms, for example 2-fluoro Specific examples include an ethylcarbamoyl group, a 2-chloroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a 2,2,2-trifluoroethylcarbamoyl group, and the like, each selected within the specified number of carbon atoms. Is done.
  • the notation of di (C a -C b alkyl) aminocarbonyl means in the above meaning that the number of carbon atoms, which may be the same or different from each other, is ab.
  • Specific examples include a group, an N, N-di (n-butyl) carbamoyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylaminosulfonyl represents a sulfamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms.
  • Famoyl group ethylsulfamoyl group, n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group, i-butylsulfamoyl group, s-butylsulfamoyl group, Specific examples include a tert-butylsulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
  • di (C a -C b alkyl) aminosulfonyl means in the above meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b.
  • R 5a (C a ⁇ C b ) alkyl optionally substituted with R 10a (C a ⁇ C b ) alkyl, optionally substituted with R 15a (C a ⁇ C b) alkyl, optionally substituted with R 15b (C a ⁇ C b ) alkyl, optionally substituted with R 15c (C a ⁇ C b ) alkyl, optionally substituted with R 15d (C a ⁇ C b) alkyl, optionally substituted with R 20 (C a ⁇ C b ) alkyl, optionally substituted with R 28 (C a ⁇ C b ) alkyl, optionally substituted with R 28a (C a ⁇ C b) alkyl, optionally substituted with R 31 (C a ⁇ C b ) alkyl or optionally substituted with R 32 (C a ⁇ C b ) notation alkyl or the like, any of
  • R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
  • R 5a C a ⁇ C b cycloalkyl
  • R 10a C a ⁇ C b cycloalkyl
  • R 15a C a ⁇ C b
  • R 15b C a ⁇ C b
  • R 15c C a ⁇ C b
  • R 15d been (C a ⁇ C b) cycloalkyl
  • R 20 C a ⁇ C b
  • R 28 optionally substituted in (C a ⁇ C b) cycloalkyl
  • each R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28a , R 31 or R 32 may be the same or different from each other;
  • the substitution position may be a ring structure moiety, a side chain moiety, or both.
  • R 5a (C a ⁇ C b ) alkenyl optionally substituted with R 10a (C a ⁇ C b ) alkenyl, optionally substituted with R 15a (C a ⁇ C b) alkenyl, optionally substituted with R 15b (C a ⁇ C b ) alkenyl, optionally substituted with R 15c (C a ⁇ C b ) alkenyl, optionally substituted with R 15d (C a ⁇ C b) alkenyl, optionally substituted with R 20 (C a ⁇ C b ) alkenyl, optionally substituted with R 28 (C a ⁇ C b ) alkenyl, optionally substituted with R 28a (C a ⁇ C b) alkenyl, which is optionally substituted with R 31 (C a ⁇ C b ) alkenyl or optionally substituted with R 32 (C a ⁇ C b ) alkenyl, which
  • R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
  • R 5a (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 10a (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 15a (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 15b (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 15c (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 15d (C a ⁇ C b) cycloalkenyl, substituted optionally substituted with R 20 (C a ⁇ C b ) cycloalkenyl, optionally substituted with R 28 (C a ⁇ C b ) cycloalkenyl, optionally with R 28a been (C a ⁇ C b) cycloalkenyl, optionally substituted with R 31 (C a ⁇ C b) cycl
  • Is represented by any R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 , and a hydrogen atom bonded to a carbon atom is arbitrarily It represents a cycloalkenyl group having the above meaning consisting of a to b substituted carbon atoms, and is selected in the range of each designated number of carbon atoms.
  • each R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 may be the same or different from each other.
  • the substitution position may be a ring structure part, a side chain part, or both.
  • R 5a (C a ⁇ C b ) alkynyl optionally substituted with R 10a (C a ⁇ C b ) alkynyl, optionally substituted with R 15a (C a ⁇ C b) alkynyl, optionally substituted with R 15b (C a ⁇ C b ) alkynyl, optionally substituted with R 15c (C a ⁇ C b ) alkynyl, optionally substituted with R 15d (C a (C b ) alkynyl, optionally substituted with R 20 (C a -C b ) alkynyl, optionally substituted with R 28 (C a -C b ) alkynyl, optionally substituted with R 28a (C a ⁇ C b) alkynyl, which is optionally substituted with R 31 (C a ⁇ C b ) alkynyl or optionally substituted with R 32
  • R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
  • [R 8a is by forming alkenylene chain alkylene chain or C 2 ⁇ C 7 of C 2 ⁇ C 7 together with R 9a, 3 ⁇ 8-membered ring together with the nitrogen atom to which R 8a and R 9a are bonded
  • the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom
  • [R 13a is by forming alkenylene chain alkylene chain or C 2 ⁇ C 7 of C 2 ⁇ C 7 together with R 14a, 3 ⁇ 8-membered ring together with the nitrogen atom to which R 13a and R 14a are attached
  • the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom
  • [R 13b is by forming alkenylene chain alkylene chain or C 2 ⁇ C 7 of C 2 ⁇ C 7 together with R 14b, 3 ⁇ 8-membered ring together with the nitrogen atom to which R 13b and R 14b are bonded
  • R 14e herein by forming the alkenylene chain alkylene chain or C 2 ⁇ C 7 of C 2 ⁇ C 7 together with R 14f, 3 together with the carbon atom to which R 14e and R 14f are bonded May form an ⁇ 8-membered ring, and this alkylene chain or alkenylene chain may contain 1, 2 or 3 oxygen atoms, sulfur atoms or nitrogen atoms.
  • Specific examples of the notation include, for example, cyclopropylidene, cyclobutylidene, cyclopentylidene, cyclohexylidene, oxetane-3-ylidene, thietan-3-ylidene, dihydrofuran-3-ylidene, dihydrothiophene-3-ylidene, Dihydropyran-3-ylidene, dihydropyran-4-ylidene, dihydrothiopyran-3-ylidene, dihydrothiopyran-4-ylid
  • the compound of the present invention can be produced by the following method. Manufacturing method A Formula (6) [wherein A 1 , R 2 , R 3 , R 4 , R 6b , R a and n represent the same meaning as described above. And a compound represented by the formula (7) [wherein A 1 , R 2 , R 3 , R 4 , R a and n represent the same meaning as described above]. The compound represented by this can be obtained.
  • hydrochloric acid hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, trifluoroacetic acid and the like can be used.
  • base potassium carbonate, sodium hydroxide or the like can be used. This reaction may be carried out without solvent, but a solvent may be used.
  • polar solvents such as acetonitrile and water, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, and aromatic hydrocarbons such as benzene, toluene and xylene Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • the compound represented by the formula (7) thus obtained is represented by the formula (8-1) [wherein R 7b represents the same meaning as described above. And a compound represented by formula (9) [wherein A 1 , R 2 , R 3 , R 4 , R 7b , R a and n represent the same meaning as described above].
  • This invention compound represented by this can be synthesize
  • the compound represented by formula (8-1) is used in the range of 0.5 to 50 equivalents, preferably 0.8 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (7). be able to.
  • a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used.
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • the compounds represented by formula (8-1) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature. Further, the compound represented by the formula (7) is converted into the formula (8-2) using a condensing agent, wherein R 7b represents the same meaning as described above.
  • the compound of the present invention represented by formula (9) can also be synthesized by reacting with the compound represented by formula (9). In this reaction, 1 to 4 equivalents of WSC ⁇ 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride ⁇ , CDI (carbonyldiimidazole) per 1 equivalent of the compound represented by formula (8-2) ) And the like can be used.
  • the compound represented by the formula (8-2) is used in the range of 0.5 to 50 equivalents, preferably 0.8 to 2 equivalents with respect to 1 equivalent of the compound represented by the formula (7).
  • a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used.
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • Some of the compounds represented by formula (8-2) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
  • the amount of the compound represented by the formula (2-2) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the formula (2-12).
  • Some of the compounds represented by the formula (2-2) used here are known compounds, and some of them are commercially available. Others can be synthesized according to the methods described in the literature.
  • Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, and copper (I) acetate.
  • copper catalysts such as copper (II) acetate, copper (I) oxide, copper (II) oxide and copper iodide.
  • the amount of the catalyst to be used is 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 1 equivalent relative to 1 equivalent of the compound represented by formula (2-12). It can be used in the range of 0.2 equivalents.
  • the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. .
  • the amount of the base used can be 0.1 to 10.0 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound represented by formula (2-12).
  • This reaction can be carried out without solvent, but a solvent may be used.
  • a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • Manufacturing method C A compound represented by the formula (9), diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent; 2,4-bis (4-methoxyphenyl) -1 , 3,2,4-dithiadiphosphetane-2,4-disulfide) and the like to react with a compound represented by the formula (35) [wherein A 1 , R 2 , R 3 , R 4 , R 7b , R a and n represent the same meaning as described above. This invention compound represented by this can be obtained.
  • the sulfurizing agent used in this reaction can be used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (9). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used. This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • Manufacturing method D Formula (13) [wherein A 1 , R 2 , R 3 , R 4 and n represent the same meaning as described above.
  • the compound represented by the formula (8-1) or the compound represented by the formula (8-2) is reacted with the compound represented by the formula (8-1) using the same method as the production method A. 41) [wherein A 1 , R 2 , R 3 , R 4 , R 7b and n represent the same meaning as described above.
  • This invention compound represented by this can be obtained.
  • the compound represented by the formula (41) is represented by the formula (5) [wherein R a represents the same meaning as described above, J b represents a halogen atom, —OH, —OSO 2 CH 3 , —OSO 2 CF 3 Represents a leaving group.
  • the compound of the present invention represented by the formula (9) can also be obtained by reacting with the compound represented by formula (9).
  • the compound represented by formula (5) is used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (41). Can do.
  • bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or diethyl Mitsunobu reaction using azodicarboxylate and triphenylphosphine can be used.
  • This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • Some of the compounds represented by formula (5) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
  • Manufacturing method F Formula (9-4) [wherein A 1 , R 2 , R 3 , R 4 , R 12b , R a and n represent the same meaning as described above.
  • the compound represented by formula (9-5) which is a geometric isomer of the oxime moiety, is prepared in the same manner as in Production Method E, wherein A 1 , R 2 , R 3 , R 4 , R 12b , R a and n represent the same meaning as described above.
  • This invention compound represented by this can be obtained.
  • the compound of the present invention represented by the formula (9-4) can also be obtained from the compound represented by the formula (9-5).
  • J a is a hydrogen atom, a halogen atom, —OH, —OSO 2 CH 3 , —OSO 2 CF 3 , — It represents a leaving group such as C (O) OH, —C (O) OR 52 , and R 52 represents C 1 -C 6 alkyl, phenyl or the like.
  • the compound of the present invention represented by the formula (9-T) can be obtained by reacting the compound represented by formula (9-T) in the presence of a catalyst and a base.
  • the amount of the compound represented by the formula (2-2) is in the range of 0.8 to 5 equivalents, preferably 0.8 to 2 equivalents with respect to 1 equivalent of the compound represented by the formula (17-T). Can be used.
  • Some of the compounds represented by the formula (2-2) used here are known compounds, and some of them are commercially available. Others can be synthesized according to the methods described in the literature.
  • Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, and copper (I) acetate.
  • palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, and copper (I) acetate.
  • Copper catalysts such as copper acetate (II), copper oxide (I), copper oxide (II) and copper iodide
  • nickel catalysts such as bis (1,5-cyclooctadiene) nickel and nickel (II) acetylacetonate Is mentioned.
  • the amount of the catalyst used is 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 1 equivalent, relative to 1 equivalent of the compound represented by the formula (17-T). It can be used in the range of 0.2 equivalents.
  • the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. .
  • the amount of the base used can be 0.1 to 10.0 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound represented by the formula (17-T).
  • This reaction can be carried out without solvent, but a solvent may be used.
  • a solvent for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • the compound of the present invention represented by the formula (41-T) can be obtained by reacting the compound represented by the formula (2-2) with the compound represented by the formula (2-2) in the same manner as in Production Method J. .
  • the reaction from production method A to production method K may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
  • the reaction mixture after completion of the reaction is directly concentrated, or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent.
  • the objective compound of the present invention can be obtained.
  • it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
  • reaction formula 1 The compound represented by the formula (6) used in the production method A can be synthesized, for example, according to the following reaction formulas 1 and 2. Reaction formula 1
  • Formula (2-1) [wherein R 3 and R 4 represent the same meaning as described above, and R 50 represents a C 1 -C 6 alkyl group. ] Can be synthesized by a known method such as Sinlet 2004, Vol. 4, 703. The compound represented by the formula (2-1) is converted into a known formula (2-2) according to a known method known in the literature, for example, the method described in Journal of Organic Chemistry 2004, 69, 5578.
  • R 51 represents a hydrogen atom or C 1 to C 6 alkyl which may be the same or different, or two R 51 together represent —CH 2 CH 2 — or —C (CH 3 ) 2.
  • C (CH 3 ) 2 — may be formed).
  • the compound represented by the formula (2-3) is represented by the formula (2-4) [wherein R 3 , R 4 and R 50 represent the same meaning as described above, and R 51 represents a methoxy group, an ethoxy group, a dimethyl group, Represents a leaving group such as an amino group.
  • a compound represented by formula (2-5) [wherein A 1 , R 2 and n represent the same meaning as described above. Can be synthesized according to a method known in the literature, for example, the method described in Journal of Heterocyclic Chemistry 1987, Vol. 24, page 1669.
  • the compound represented by the formula (2-4) can be obtained by a known method such as Journal of Heterocyclic Chemistry 1987, 24, 693, etc., and the compound represented by the formula (2-5) can be obtained by using a journal of medicinal. Chemistry 2002, 45, 5397, etc. can be synthesized. Further, the compound represented by the formula (2-3) is hydrolyzed according to a known method known in the literature to obtain a compound represented by the formula (2) [wherein A 1 , R 2 , R 3 , R 4 and n Represents the same meaning as described above. The compound represented by this can be manufactured.
  • Reaction formula 2 The compound represented by formula (2) is diphenylphosphoryl azide (DPPA) and formula (3) [wherein R 6b represents the same meaning as described above.
  • DPPA diphenylphosphoryl azide
  • formula (3) [wherein R 6b represents the same meaning as described above.
  • a 1 , R 2 , R 3 , R 4 , R 6b and n have the same meaning as described above. The compound represented by this can be obtained.
  • DPPA can be used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (2).
  • the compound to be used can be used in the range of 1 equivalent to a solvent amount with respect to 1 equivalent of the compound represented by the formula (2).
  • a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used. This reaction can be carried out without solvent, but a solvent may be used.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
  • Formula (2-6) [wherein R 3 , R 4 and R 50 represent the same meaning as described above, and P 1 represents tertiary butyl, benzyl, 4-methoxybenzyl, acetyl, benzoyl, benzenesulfonyl, p-toluenesulfonyl. Represents a protecting group such as methanesulfonyl, methoxymethyl or methylthiomethyl. ] Can be synthesized by known methods such as Journal of Heterocyclic Chemistry 1987, 24, 693.
  • the compound represented by the formula (7) used in the production method A can be synthesized, for example, as follows.
  • Reaction formula 4 Formula (2-13) [wherein R 3, R 4 and R a are as defined above. ] Can be synthesized by a known method such as International Publication No. 2011/048082.
  • the compound represented by formula (7) is synthesized by reacting the compound represented by formula (2-13) with the compound represented by formula (2-2) in the same manner as in Production Method B. be able to.
  • the formula (2-14) [wherein A 1 , R 2 , R 3 , R 4 and n are the same as defined above] Represents meaning. ] Can be synthesized.
  • the compound represented by the formula (2-14) is obtained by converting the compound represented by the formula (2-15) into a method known in the literature, for example, Journal of Heterocyclic Chemistry 1981, Vol. 18, p. According to the method described, it can be synthesized by reacting.
  • the compound represented by the formula (2-15) can be synthesized by a known method such as European Journal of Organic Chemistry 2004, No. 4, page 695.
  • the compound represented by the formula (2-14) is obtained by reacting the compound represented by the formula (2-16) and the compound represented by the formula (2-2) in the same manner as in Production Method B. Can be synthesized. Some of the compounds represented by formula (2-16) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature. Subsequently, the compound represented by the formula (2-14) is converted into the formula (13) by the known nitro group reduction method, wherein A 1 , R 2 , R 3 , R 4 and n have the same meaning as described above. To express. ] Can be synthesized.
  • the compound represented by the formula (13) is obtained by converting the compound represented by the formula (2) into a diphenyl phosphate according to a method known in the literature, for example, the method described in Pharmaceutical Journal 1990, 110, 457, etc. It can be synthesized by reacting with azide (DPPA).
  • DPPA azide
  • the compound represented by the formula (2-14b) can be further synthesized by reacting according to a method known in the literature, for example, the method described in Tetrahedron 2013, 69, 395.
  • Reaction formula 6 The compound represented by the formula (2-7) is reacted according to a method known in the literature, for example, the method described in Tetrahedron Letters 2003, 44, 7629, etc. [Wherein R 3 , R 4 and P 1 represent the same meaning as described above. ] Can be synthesized. Subsequently, the compound represented by the formula (2-17) is converted into a method known in the literature, for example, according to the method described in Experimental Chemistry Course 5th Edition (Edited by The Chemical Society of Japan) 2005, Vol. 14, p. Formula (2-18) [wherein M represents an alkali metal such as sodium or potassium. Or a compound represented by formula (2-19) [wherein M represents the same meaning as described above.
  • Reaction formula 7 Formula (8-3) [wherein R 11b , R 50 and J b represent the same meaning as described above, and R 60 and R 61 each independently represent a hydrogen atom, a C 1 -C 6 alkyl group or R 15c. Represents a (C 1 -C 6 ) alkyl group optionally substituted with, R 15c represents the same meaning as described above, and t represents an integer of 0 to 6. ]
  • R 15c represents the same meaning as described above, and t represents an integer of 0 to 6.
  • Formula (8-4) [wherein R 16c represents the same meaning as described above. Some of the compounds represented by] are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
  • bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or diethyl Mitsunobu reaction using azodicarboxylate and triphenylphosphine can be used.
  • This reaction can be carried out without solvent, but a solvent may be used.
  • a solvent for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons.
  • the reaction temperature can be set to any temperature from ⁇ 60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
  • formula (8-8) [wherein R 16c , R 50 , R 60 , R 61 and t represent the same meaning as described above.
  • the compound represented by formula (8-9) [wherein R 11b represents the same meaning as described above] according to the method described in International Publication No. 2007/026221.
  • the compound represented by formula (8-5) can also be obtained by reacting with the compound represented by formula (8).
  • the compound represented by the formula (8-5) is subjected to a hydrolysis reaction according to a known method known in the literature to obtain a compound represented by the formula (8-6) [wherein R 11b , R 16c , R 60 , R 61 and t represent the same meaning as described above.
  • the compound represented by this can be obtained.
  • a compound represented by the formula (8-6) by reacting the compound represented by the formula (8-6) with a halogenating agent such as thionyl chloride or oxalyl chloride according to a known method known in the literature, a compound represented by the formula (8-7) [in the formula, 11b , R 16c , R 60 , R 61 and t have the same meaning as described above.
  • the compound represented by this can be obtained.
  • Reaction formula 8 Formula (8-8) [wherein R 16c , R 50 , R 60 , R 61 and t represent the same meaning as described above.
  • the compound represented by formula (8-10) [wherein R 13b and R 14b represent the same meaning as described above, according to the method described in International Publication No. 2009/102997 and the like.
  • R 13b , R 14b , R 16c , R 50 , R 60 , R 61 and t have the same meaning as described above.
  • the compound represented by this can be obtained.
  • Some of the compounds represented by formula (8-10) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
  • Formula (8-11) which can be synthesized by a known method described in Journal of the Chemical Society Parkin Transactions 1 1981, Vol. 18, p. 9, etc. [wherein R 13b , R 14b , R 50 , R 60 , R 61 , J b and t represent the same meaning as described above.
  • the compound represented by the formula (8-12) may be synthesized by reacting the compound represented by the formula (8-4) with the compound represented by the formula (8-4) by the same method as the reaction formula 7. I can do it.
  • Reaction formula 9 Formula (14-T) [wherein R 3 , R 6b and J a represent the same meaning as described above.
  • the compound represented by formula (5) is reacted with the compound represented by formula (5) using the same method as in Production Method B, thereby producing a compound represented by formula (15-T) [wherein R 3 , R a , R 6b and J a represent the same meaning as described above.
  • the compound represented by this can be obtained.
  • the compound represented by the formula (14-T) can be easily produced according to a known method known in the literature, for example, a method described in Bioorganic Medicinal Chemistry Letters 2010, 20th, 1559, etc.
  • the compound represented by the formula (15-T) is reacted with an acid or a base using the same method as in Production Method A to obtain a compound represented by the formula (16-T) [wherein R 3 , R a and J a Represents the same meaning as described above. The compound represented by this can be obtained. Further, the compound represented by the formula (16-T) is reacted with the compound represented by the formula (8-1) or the compound represented by the formula (8-2) by using the same method as in Production Method A. To obtain a compound represented by the formula (17-T).
  • the compound represented by the formula (14-T) is reacted with an acid or a base in the same manner as in the reaction formula 1, and the formula (18-T) [wherein R 3 and J a represent the same meaning as described above. .
  • the compound represented by this can be obtained.
  • the compound represented by the formula (18-T) is reacted with the compound represented by the formula (8-1) or the compound represented by the formula (8-2) by using the same method as in Production Method A. By doing so, a compound represented by the formula (19-T) can be obtained.
  • the compound represented by the formula (19-T) is represented.
  • the compound represented by the formula (17-T) is represented. Can be obtained.
  • the active compound included in the present invention include compounds shown in Tables 1 to 4.
  • the compounds in Tables 1 to 4 are for illustrative purposes, and the present invention is not limited thereto.
  • a substituent described as Me represents a methyl group, hereinafter, Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n are normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu--- i is an isobutyl group, t-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, c-Pen and Pen -C is a cyclopentyl
  • D1-7b D1-32a, D1-32b, D1-32c, D1-33a, D1-34a, D1-37a, D1-79a, D1-79b, D1-80a, D1-80b , D1-80c, D1-80d, D1-80e, D1-80f, D1-87a, D1-98a, D1-103m, D1-103o, D1-103p, D1-103q, D1-108a, D1-108b, D1 -108c, D1-104a, D1-104b, and structures represented by D1-104c represents the following structures, D1-7b, and structure number marked on the type D1-32b the substitution position of X 1 Represents the substitution position of X 1b , and the number written in the structural formula of D1-108b represents the substitution position of Z.
  • the compounds of the present invention are stored in warehouses, so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called sanitary pests that cause various adverse effects in the human living environment such as houses. It is possible to effectively control insects such as so-called stored grain pests that harm cereals and the like, and pests such as mites, crustaceans, molluscs, and nematodes that occur and harm in similar situations at low concentrations.
  • insects, mites, crustaceans, mollusks and nematodes that can be controlled using the compounds of the present invention include, for example, the wasp chestnut gall wasp (Dryocosmus kuriphilus), the Argentine ant Argentine ant (Linepithema humile), Gunmy ant Army ant (Eciton burchelli, E.
  • Desert locust (Schistocerca gregaria), Australian platypus locust Australian plague locust (Chortoicetes terminifera), locust grasshopper Migratory locust (Locusta migratoria), red-eye locust Lesser paddy grasshopper (Oxya japonica), red-eye grass oxen (Teleogryllus emma), Kela Oriental mole cricket (Gryllotalpa orientalis), etc., Orthoptera insects, German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta jafonica), Japanese cockroach (Periplaneta japonica), Daikokuus tomato (America) Termite Western dry-wood termite (Incisitermes minor), Common termite Formosan subterranean termite (Coptotermes formosanus), Japanese termite Japanese subterranean termit
  • Isopoda crustaceans such as Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber), Butterflyfish (Arguloida) crustaceans such as butterfly (Argulus coregoni), butterfly Japanese fishlouse (Argulus japonicus), sea butterfly (Argulus scutiformis) Sea louse (Caligus curtus, C.
  • Tick American cattle tick (Rhipicephalus annulatus), Brown dog tick (Rhipicephalus sanguineus) and other ticks (Metastigmata) ticks, Red mite (Dermanyssus gallinae), house dust mite Tropical rat mite (Ornithonyssus bacoti), northern fowl mite (Ornithonyssus sylviarum), honey bee mite Honeybee mite (Varroa destructor), honeybee mite Varroa mite Varroa mite (Mesostigmata) mites, Pancreas (Architaenioglossa) gastropod, such as Apple snail (Pomacea canaliculata) Giant African snail (Achatina fulica), terrestrial slug (Limax marginatus), slug slug (Meghimatium bilineatum), Korean round snail (Acusta despecta sieboldiana), Miss maimai Land snio (Euha
  • Rice white nematode (Aphelenchoides besseyi), Pine wood nematode (Bursaphelenchus xylophilus) nematode (Aphelenchida) nematode, Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode Cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Seterbean cyst nematode (Heterodera glycines)), arenaria root nematode (Peterut root-Menot nematode) -knot nematode (Meloidogyne hapla), Southern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Southern root-kion nematode Coffee root-lesion nem
  • lenchida nematode
  • Oxyurida nematodes such as human worm Pinworm (Enterobius vermicularis), horse worm Equine pinworm (Oxyuris equi), rabbit worm Rabbit pinworm (Passalurus ambiguus), Pig roundworm (Ascaris suum), Horse roundworm Horse roundworm (Parascaris equorum), Dog roundworm Dog roundworm (Toxascaris leonina), Dog roundworm Dog intestinal roundworm (Toxocara canis), Cat roundworm Feline roundworm (Toxocara cati), Cattle roundworm Large cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., chicken caecal caecal worm (Heterakis gallinarum), chicken roundworm (Ascaridia galli) and other roundworms (Ascaridida) Nematode, Medinaworm Guinea worm (Dracunculus medinens
  • Striated insects (Pharyngostomum cordatum), Schistosoma haematobium, Schistosoma haematobium, Schistosoma japonicum, Schistosoma japonicum, Schistosoma mansoni, etc.
  • Echinostoma cinetorchis Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Liver common liver fluke (Fasciola hepatica), Fasciolopsis buski, Flat belly twin Echinostomida, such as Homalogaster paloniae, Continental flukes (Dicrocoelium chinensis), moth-type flukes Lancet liver fluke (Dicrocoelium dendriticum), African moth-type flukes African lancet fluke (Dicrocoelium hospes), small pancreatic folds (Eurytrema coelomaticum), pancreatic folds Pancreatic fluke (Eurytrema pancreaticum) Paragonimus miyazakii, Paragonimus ohirai, Westermann Lung fluke (Paragonimus westermani), etc.
  • Platimorchiida Amphimerus spp., Liver fluke Chinese liver fluke (Clonorchis sinensis), Cat liver fluke Cat liver fluke (Opisthorchis felineus), Thai liver fluke Southeast Aasian liver fluke (Opisthorchis viverrini), Pseudamphistom spp .), Metrochis spp., Parametorchis spp., Malformed fluke (Heterophyes heterophyes), Metagonimus yokokawai, foregut fluke (Pygidiopsis summa), etc. Opisthorchiida) fluke, Amoeba such as Entamoeba histolytica, E.
  • cidiorida spores
  • Vestibuliferida ciliates such as large intestine barantidium coli, Histomanas meleagridis, Pentatrichomonas hominis, Trichomonas tenax and other Trichomonadida flagellates, Dipromonads (Vaccinonadida) flagellates such as Giardia intestinalis, Giardia muris, turkey hexamita (Hexamita meleagridis), Hexamita parva, Leishmania donovani, Leishmania infantum, Leishmania major, Leishmania tropica, Trypanosoma brucei gambiense, Trypanosoma brucei cruise, Trypanosoma brucei rhodesi Examples include Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi, and Kinetoplastida flagellates, which can be controlled using the compounds of the present invention
  • the compound of the present invention is also effective against pests having developed resistance against existing insecticides such as organophosphorus compounds, carbamate compounds or pyrethroid compounds. That is, the compound of the present invention is composed of the order of mucous (Coleoptera); Eyes), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flyes), etc.
  • pests belonging to gastropods and nematodes can be effectively controlled at low concentrations.
  • the compound of the present invention has extremely no adverse effect on mammals, fish, crustaceans and beneficial insects (beneficial insects such as honeybees, bumblebees, natural enemies such as honeybees, wasps, mistletoe, spider mites, burdock mites). Has useful features.
  • the compound of the present invention When using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent. , Disintegrating agents, antifoaming agents, antiseptics, anti-degradation agents, etc., adding liquid (soluble concentrate), emulsion (emulsifiable concentrate), wettable powder (wettable powder), water solvent (water soluble powder) Water dispersible granule, water soluble granule, suspension ⁇ concentrate, emulsion ⁇ concentrated ⁇ suspoemulsion, microemulsion, microemulsion, dustable powder ), Granules, tablets, emulsifiable gels, etc., can be put to practical use.
  • the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule or a water-soluble film bag.
  • solid carrier examples include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, nostirite, and allophane.
  • Sugars eg polysaccharides such as starch, powdered cellulose, dextrin, organic substances such as urea, urea derivatives, benzoic acid, benzoic acid salts, plants such as wood flour, cork flour, corn cob, walnut shell, tobacco stem , Fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.), fertilizer and the like.
  • liquid carrier examples include xylene, alkyl (C 9 or C 10 etc.) benzene, phenyl xylyl ethane, alkyl (C 1 or C 3 etc.) naphthalene and other aromatic hydrocarbons, machine oil, normal paraffin, isoparaffin, Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl Ethers, ethers such as propylene glycol monopropyl
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfates Succinate, naphthalene sulfonate, alkyl naphthalene
  • the content of these surfactants is not particularly limited, but is usually in the range of 0.05 to 20 parts by weight, preferably 0.5 to 10 parts by weight with respect to 100 parts by weight of the preparation of the present invention. . These surfactants may be used alone or in combination of two or more.
  • the application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally the active ingredient amount is about 0.005 to 50 kg per hectare (ha), preferably 0.01. ⁇ 5 kg is suitable.
  • an effective amount of the compound of the present invention is administered orally, and injected (muscles) together with pharmaceutical additives.
  • Parenteral administration such as internal, subcutaneous, intravenous, intraperitoneal
  • transdermal administration such as immersion, spraying, bathing, washing, pouring-on, spotting-on, dusting
  • Administration can be by nasal administration.
  • the compounds of the present invention can be administered by molded products using strips, plates, bands, collars, ear marks, limb bands, labeling devices and the like. In administration, the compound of the present invention can be in any dosage form suitable for the administration route.
  • Arbitrary dosage forms to be prepared include powders, granules, wettable powders, pellets, tablets, large pills, capsules, solid preparations such as molded products containing active compounds; injection solutions; oral solutions; skin Liquid preparations used above or in body cavities; Solution preparations such as Pour-on agents, Spot-on agents, flowable agents, and emulsions; Semi-solid preparations such as ointments and gels.
  • the solid preparation can be mainly used for oral administration or transdermal administration after dilution with water or environmental treatment.
  • Solid preparations can be prepared by adding the active compound, if necessary, with adjuncts and mixing with appropriate excipients to give the desired shape.
  • Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, celluloses, ground grains, and starches.
  • Injection solutions can be administered intravenously, intramuscularly and subcutaneously.
  • Injection solutions can be prepared by dissolving the active compound in a suitable solvent and adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, protective agents, etc., if necessary.
  • suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
  • the solubilizer include polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and the like.
  • Examples of the protective agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol and the like.
  • Oral solutions can be administered directly or diluted. It can be prepared in the same manner as an injectable solution. Flowables, emulsions and the like can be administered directly or diluted transdermally or by environmental treatment.
  • Solutions used on the skin can be administered by dripping, spreading, rubbing, spraying, spraying or applying by dipping (immersion, bathing or washing). These solutions can be prepared in the same manner as injection solutions. Pour-on and spot-on agents can be dripped or sprayed onto a limited area of the skin, so that the active compound is immersed in the skin and acts systemically. it can. Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers, and adhesives may be added.
  • auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers, and adhesives may be added.
  • Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1, 3-dioxolane is mentioned.
  • Absorption promoting substances include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, fatty alcohols and the like.
  • Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol and the like.
  • the emulsion can be administered orally, transdermally or as an injection.
  • the active ingredient is dissolved in a hydrophobic phase or a hydrophilic phase, and this is further added with a suitable emulsifier, and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
  • a suitable emulsifier and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
  • hydrophobic phase paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain Of a short fatty acid having a chain length and a saturated fatty acid having a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, capryl / caprate of a saturated fatty alcohol having a chain length of C12 to C18, isopropyl stearate, oleyl oleate Decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearate,
  • hydrophilic phase examples include water, propylene glycol, glycerin, sorbitol and the like.
  • nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc.
  • amphoteric surfactants such as disodium N-lauryl- ⁇ -iminodipropionate and lecithin
  • anions such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate
  • Surfactants cationic surfactants such as cetyltrimethylammonium chloride.
  • Other adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymer, polyethylene glycol, wax, colloidal silica and the like.
  • Semi-solid preparations can be administered by application on the skin or spreading or introduction into body cavities. Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.
  • [Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agent, decomposition inhibitor and the like.
  • ⁇ emulsion ⁇ Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.
  • Liquid Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.
  • wettable powder Compound No. 1-001 of the present invention 20 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Co., Ltd., Product name) Carplex # 80D 2 parts (Synthetic hydrous silicic acid: manufactured by Shionogi & Co., Ltd., trade name) The above is uniformly mixed and ground to obtain a wettable powder.
  • Suspension Agent Compound No.1-001 25 parts Agrisol S-710 10 parts (Nonionic Surfactant: Kao Corporation, trade name) LUNOX 1000C 0.5 part (anionic surfactant: Toho Chemical Industries, trade name) Xanthan gum 0.2 parts water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.
  • Granule wettable powder Compound No. 1-1001 of the present invention 75 parts Hytenol NE-15 5 parts (anionic surfactant: trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name) Carplex # 80D 10 parts (Synthetic hydrous silicic acid: manufactured by Shionogi & Co., Ltd., trade name) After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.
  • anionic surfactant trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.
  • Vanillex N 10 parts anionic surfactant: Nippon Paper Industries Co., Ltd. trade name
  • Carplex # 80D 10 parts Synthetic hydrous silicic acid: manufactured by Shion
  • composition Example 6 Powder Compound of the present invention No.1-001 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi & Co., trade name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and ground to obtain a powder. In use, the formulation is diluted 1 to 10,000 times with water or sprayed directly without dilution.
  • wettable powder preparation Compound No. 1-001 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts
  • the compound of the present invention when used as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, if necessary, at the time of formulation or spraying Alternatively, it may be mixed with a synergist, a fertilizer, a soil conditioner and the like. In particular, by applying it in combination with other agricultural chemicals or plant hormones, it can be expected to reduce costs by reducing the amount of applied medicine, expand the insecticidal spectrum due to the synergistic action of the mixed drugs, and achieve higher pest control effects. At this time, a combination with a plurality of known agricultural chemicals is also possible. Examples of the type of agricultural chemical used in combination with the compound of the present invention include compounds described in The Pesticide Manual 15th edition, 2009, and the like. Specific examples of common names are as follows, but the general names are not necessarily limited to these.
  • Bactericides acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, ametoctradin, amisulbrom, amobam, ampropyl Phos (ampropyfos), anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (Benodanil), benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzamacril, benzamorf, bethoxazine, Binapacryl ), Biphenyl, bitertanol, blasticidin-S, bixafen, bordeaux mixture, boscalid, bromoconazole, bupirimate , Buthiobate, calcium polysulfide, calcium polysulfide, captafol, captan,
  • Bactericides (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole-, diniconazole-M M), dinobuton, dinocap, dinocap-4, dinocap-6, dinoton, dinosulfon, dinoterbon, diphenylamine ), Dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, ethaconazole, etaconazole Boxaam, etem, etirimol, ethoxyquin, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, sulfaminosulfen ), Fenapanil, fendazo
  • Fungicide (continued): kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid , Mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, metoxafloxam ), Methylisothiocyanate, metiram, metinominostrobin, metrafenone, metsulfovax, milneb, microbutanil, microzoline (myc) lozolin, nabam, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OH (OCH), octhilinone, offurace, orysastrobin, oxadixyl, organic copper (oxi
  • Bactericides (continued): sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salicylanilide, silthiofam (Silthiofam), simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, thiadinyl, tioxymid, tolcrofos -Tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin,
  • Bactericides benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline , Streptomycin and tecloftalam.
  • Nematicides aldoxycarb, cadusafos, DCP, DBCH, dichlofenthion, DSP (DSP), etoprophos, fenamiphos, fensulfothion, fluene Sulfone (fluensulfone), fosthiazate (fosthiazate), fosthietan (fosthietan), imisiafos (imicyafos), isamidofos (isamidofos), isazofos (isazofos), oxamyl (oxamyl) and thionazin (thionazin) and the like.
  • Acaricides acequinocyl, acrinathrin, amitraz, BCI-033 (test name), bifenazate, bromopropylate, chinomethionat, chlorobezilate , Clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, denochlor (DNOC), etoxazole, quinazaquin (fenaza) Fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox (halfenpro) x), hexythiazox, milbemectin, propargite, pyflubumide, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen , Spyromesifen, CL900167 (test name), tebuf
  • Insecticides abamectin, acephate, acetamipirid afidopyropen, alanidocarb, aldicarb, allethrin, azaphos-methyl, azine-methyl- ), Bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin, violesmethrin, bioresmethrin (bistrifluron), buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chloranthra Chlorantraniliprole, chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos-methyl ), Chromafenozide, clothianidin, cyantraniliprole,
  • Insecticides (continued): halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion ), Lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalaldehyde, methamidophos, methidathion, methidathion, methacrifos (methacrifos) ), Metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromi de), monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeproton Phos (oxydeprofos), parathion, parathion-methyl
  • the medium pressure preparative liquid chromatography described in the synthesis example used an intermediate pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 ⁇ m column).
  • the high performance preparative liquid chromatography used Shimadzu Corporation 10AVP system on the following conditions. Oven temperature: 40 ° C
  • Mobile phase acetonitrile 7 ml / min., Water 4 ml / min.
  • Step 2 Preparation of tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl (ethyl) carbamate 60 wt% sodium hydride (dispersed in mineral oil) 0.15 g N , N-dimethylformamide (10 ml) was mixed with 0.95 g of tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-ylcarbamate under ice-cooling. After completion of the addition, the temperature was raised to room temperature and stirred at the same temperature for 30 minutes.
  • Step 3 Preparation of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine dihydrochloride tert-butyl 3-chloro-1- (pyridin-3-yl)-
  • a 20 ml 1,4-dioxane solution of 1.0 g of 1H-pyrazol-4-yl (ethyl) carbamate was added 8.1 ml of a 1,4-dioxane solution of about 4M hydrogen chloride. After completion of the addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solid precipitated in the reaction solution was removed by filtration under reduced pressure.
  • Step 4 Preparation of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine To 7.4 ml of 1N aqueous sodium hydroxide solution, 3-chloro-N-ethyl-1- 1 g of (pyridin-3-yl) -1H-pyrazol-4-amine dihydrochloride was added. After completion of the addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was extracted with 20 ml (x3) of dichloromethane.
  • Step 5 Preparation of N- ⁇ 3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl ⁇ -N-ethyl-2-oxopropanamide 3-Chloro-N-ethyl-1-
  • To a solution of 1 g of (pyridin-3-yl) -1H-pyrazol-4-amine in 10 ml of dichloromethane at room temperature is 0.59 g of pyruvic acid and 1.7 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. And 3 mg of 4-dimethylaminopyridine was added sequentially.
  • Step 6 Preparation of N- ⁇ 3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl ⁇ -N-ethyl-2- (hydroxyimino) propanamide N- ⁇ 3-Chloro- To a solution of 400 mg of 1- (pyridin-3-yl) -1H-pyrazol-4-yl ⁇ -N-ethyl-2-oxopropanamide in 5 ml of ethanol was added 179 mg of triethylamine and 123 mg of hydroxylammonium chloride. After completion of the addition, the mixture was stirred for 1 hour while refluxing ethanol.
  • the obtained residue was added to a separately prepared solution of 0.46 g of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine and 0.41 g of pyridine in 5 ml of dichloromethane. . After completion of the addition, stirring was continued at room temperature for 30 minutes. After completion of the reaction, the reaction solution was washed with 10 ml of water. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 3 Preparation of 2- (ethylthio) -2- (methoxyimino) acetic acid 4.1 ml of 1N aqueous sodium hydroxide solution was added to a solution of 0.66 g of ethyl 2- (ethylthio) -2- (methoxyimino) acetate in 5 ml of ethanol. Added. After completion of the addition, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure. The resulting residue was adjusted to pH 2 by adding a 1N aqueous hydrochloric acid solution.
  • Step 2 Preparation of 3-chloro-N- (prop-2-yn-1-yl) -1- (pyridin-3-yl) -1H-pyrazol-4-amine tert-butyl 3-chloro-1- ( Pyridine-3-yl) -1H-pyrazol-4-yl (prop-2-yn-1-yl) carbamate 9.4 g in 1,4-dioxane 15 ml solution and about 4 M hydrogen chloride in 1,4-dioxane solution 50 ml was added and stir
  • Step 3 N- ⁇ 3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl ⁇ -2- (methoxyimino) -3- (methylthio) -N- (prop-2-yne
  • 1-yl) propanamide 2- (methoxyimino) -3- (methylthio) propanoic acid 0.84 g in dichloromethane 10 ml solution at room temperature 0.65 g oxalyl chloride, then N, N-dimethylformamide 0. Added in order of 1 ml. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure.
  • the obtained residue was separated from 1.0 g of 3-chloro-N- (prop-2-yn-1-yl) -1- (pyridin-3-yl) -1H-pyrazol-4-amine prepared separately and pyridine. 0.51 g of dichloromethane in 10 ml solution was added. After the addition was complete, stirring was continued overnight at room temperature. After completion of the reaction, the reaction solution was added to 20 ml of water and extracted with 20 ml of chloroform ( ⁇ 2). The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 1: 1) to obtain 1.67 g of the desired product as a yellow oil. Obtained.
  • the obtained target product was a mixture of two geometric isomers, and the isomer ratio was 7: 1.
  • the reaction solution was added to water and extracted with 4 ml (x3) of ethyl acetate, and then the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 4: 1 to 1: 3) to obtain 65 mg of the desired product as a colorless oil.
  • the obtained target product was a mixture of two geometric isomers, and the isomer ratio was 5: 1.
  • reaction solution was stirred overnight at room temperature.
  • solvent was distilled off from the reaction solution under reduced pressure, and the resulting solid was added to 30 ml of 2N aqueous sodium hydroxide solution.
  • insoluble matter precipitated in the solution was removed by filtration.
  • the obtained filtrate was adjusted to pH 3 with concentrated hydrochloric acid, and the precipitated solid was removed by filtration.
  • the obtained solid was washed with water and dried under reduced pressure to obtain 2.5 g of the desired product as a white solid.
  • Step 2 2- [2-[ ⁇ 3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl ⁇ amino] -2-oxoethylidene] -N- (2,6-dichlorophenyl)
  • 2- [2- ⁇ (2,6-dichlorophenyl) carbamoyl ⁇ hydrazono] acetic acid in a solution of 235 mg of dichloromethane in 4 ml of dichloromethane was mixed with 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine 150 mg and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 223 mg were sequentially added.
  • reaction solution was stirred at room temperature for 2 hours. After completion of the reaction, 4 ml of water was added to the reaction solution. After completion of the addition, the solid precipitated in the solution was taken out by filtration. The obtained solid was washed with water and then with isopropyl ether, and then dried under reduced pressure to obtain 280 mg of the desired product as a white solid. Melting point: 211-214 ° C
  • reaction mixture was heated to 80 ° C. and stirring was continued for 1 hour at the same temperature.
  • 30 ml of water was added to the reaction mixture and extracted with 50 ml of ethyl acetate.
  • the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, washed with saturated brine, and then dried over anhydrous sodium sulfate in that order.
  • the solvent was distilled off under reduced pressure to obtain 2 g of the desired product as a pale yellow oil.
  • Step 3 Production of N- ⁇ 4-methyl-2- (pyridin-3-yl) thiazol-5-yl ⁇ -2- (methoxyimino) -3- (methylthio) propanamide 2- (methoxyimino) -3 -360 mg of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added to a solution of 370 mg of (methylthio) propanoic acid in 3 ml of dichloromethane. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours.
  • reaction mixture was added dropwise to a separately prepared solution of 4-methyl-2- (pyridin-3-yl) thiazol-5-amine dihydrochloride (500 mg) and pyridine (747 mg) in ethylene dichloride (5 ml). After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed with 10 ml of water and then with 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and then the organic layer was separated by a liquid separation operation. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the reaction mixture was added dropwise to a separately prepared solution of 150 mg of 4-chloro-N-ethyl-2- (pyridin-3-yl) thiazol-5-amine and 198 mg of pyridine in 5 ml of ethylene dichloride at room temperature. . After completion of dropping, the mixture was stirred overnight at the same temperature. After completion of the reaction, the reaction mixture was washed with 10 ml of water and then with 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and then the organic layer was separated by a liquid separation operation. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 2 Preparation of N- (2-bromo-4-methylthiazol-5-yl) -2- (methoxyimino) -3- (methylthio) butanamide 2- (methoxyimino) -3- (methylthio) butanoic acid 0
  • dichloromethane 0.65 g of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added in this order. After completion of the addition, the mixture was stirred at room temperature for 1 hour.
  • Step 3 Preparation of 2- (methoxyimino) -N- ⁇ 4-methyl-2- (pyridin-3-yl) thiazol-5-yl ⁇ -3- (methylthio) butanamide N- (2-Bromo-4-
  • a solution of 0.1 g of methylthiazol-5-yl) -2- (methoxyimino) -3- (methylthio) butanamide and 0.05 g of 3-pyridylboronic acid in 5 ml of 1,4-dioxane and 3 ml of water 0. 2 g and bis (triphenylphosphine) palladium (II) dichloride 0.06 g were added and stirred at 90 ° C. for 1 hour.
  • the solvent was distilled off from the reaction solution under reduced pressure, the resulting solid was added to 30 ml of 2N aqueous sodium hydroxide solution, and insoluble matters were removed by filtration.
  • the obtained filtrate was adjusted to pH 3 with concentrated hydrochloric acid, and the precipitated solid was removed by filtration.
  • the obtained solid was washed with water and dried under reduced pressure to obtain 2.5 g of the desired product as a white solid.
  • Step 2 N- (2,6-Dichlorophenyl) -2- [2-[ ⁇ 4-methyl-2- (pyridin-3-yl) thiazol-5-yl ⁇ amino] -2-oxoethylidene] hydrazinecarboxamide
  • Preparation of Preparation 2- [2- ⁇ (2,6-dichlorophenyl) carbamoyl ⁇ hydrazono] acetic acid in 160 mg of dichloromethane in 4 ml solution was added 4-methyl-2- (pyridin-3-yl) thiazol-5-amine 100 mg, 1- Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 131 mg was sequentially added, and the mixture was stirred at room temperature for 1 hour.
  • reaction mixture was cooled to 0 ° C., neutralized with an aqueous sodium hydroxide solution, and extracted with 100 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained solid was washed with n-hexane to obtain 6.28 g of the desired product as a white solid.
  • Step 2 Preparation of ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 10.3-g N, N-dimethyl ethyl 3-chloro-1H-pyrazole-4-carboxylate To a 150 ml formamide solution, 15.6 g of 3-iodopyridine, 2.23 g of copper iodide (monovalent) and 33.0 g of cesium carbonate were sequentially added.
  • reaction vessel was replaced with nitrogen gas, followed by stirring at 130 ° C. for 5 hours.
  • reaction mixture was allowed to cool to room temperature and 100 ml of 1N aqueous sodium hydroxide solution was added. Impurities in the reaction mixture were removed by Celite filtration under reduced pressure, and the obtained filtrate was extracted with 100 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • Step 3 Preparation of 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid
  • Ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 5.6 g of potassium hydroxide and 130 ml of water were sequentially added to a solution of 16.75 g of ethanol in 130 ml. After the addition was complete, the mixture was stirred overnight at room temperature. After completion of the reaction, 2N hydrochloric acid aqueous solution was added to adjust the pH of the reaction mixture to 4. Then, the precipitated solid was removed by filtration, and the removed solid was washed with water.
  • Step 4 Preparation of 3- (3-chloro-4-nitro-1H-pyrazol-1-yl) pyridine 1.72 ml of acetic anhydride was added dropwise to a solution of concentrated hydrochloric acid 9 ml and fuming nitric acid 3.1 ml at a temperature of 40 ° C or lower. did.
  • reaction mixture was stirred at room temperature for 30 minutes. After stirring, the reaction mixture was heated to 60 ° C. After completion of heating, 5 g of 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid was added to the reaction mixture in 5 portions while maintaining 60 ° C. After completion of the addition, stirring was continued at 65 ° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with 1N aqueous sodium hydroxide solution. The precipitated solid was filtered, washed with water, and dried to obtain 4.2 g of the desired product as a pale yellow solid.
  • Step 5 Preparation of 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3- (3-Chloro-4-nitro-1H-pyrazol-1-yl) pyridine 4 g of ethyl acetate A solution of 20 ml, 10 ml of acetic acid and 10 ml of water was heated to 65 ° C., and 2.5 g of reduced iron was added little by little. After completion of the addition, the mixture was stirred at 70 ° C. for 2 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature, 50 ml of water was added, and the pH of the reaction solution was adjusted to 10 with sodium bicarbonate.
  • Step 2 Preparation of 2- (methoxyimino) -3- (methylthio) propanoic acid To a mixed solution of 1.84 g of ethyl 2- (methoxyimino) -3- (methylthio) propanoate in 10 ml of water and 10 ml of ethanol, sodium hydroxide 430 mg was added. After completion of the addition, the mixture was stirred at room temperature for 2 days.
  • reaction mixture was stirred overnight at room temperature.
  • 20 ml of saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was extracted with 30 ml of ethyl acetate.
  • the obtained organic layer was washed with water, then washed and dried with saturated brine and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (5: 1) to obtain 0.8 g of the desired product as a yellow oil.
  • Step 2 Preparation of ethyl 2- (methoxyimino) -3- (methylthio) butanoate (Compound E-001) To a solution of 0.8 g of ethyl 2- (methoxyimino) -3- (tosyloxy) butanoate in 5 ml of N, N-dimethylformamide was added 0.2 g of sodium methyl mercaptan at 0 ° C. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction solution and extracted with 10 ml of ethyl acetate.
  • reaction solution was cooled to 0 ° C., 10 ml of acetone, 5.2 g of potassium carbonate, and 2.5 g of sodium ethyl mercaptan were sequentially added, followed by stirring at room temperature for 1 hour. After completion of the reaction, 30 ml of hexane and 30 ml of water were added to the reaction solution, and the aqueous layer was taken out by a liquid separation operation. To the obtained aqueous layer, 10 ml of concentrated hydrochloric acid was added, followed by extraction with 50 ml of ethyl acetate.
  • Step 2 Production of 3- (ethylthio) -2- (methoxyimino) butanoic acid (Compound F-004) To a solution of 1 g of 3- (ethylthio) -2-oxobutanoic acid in 10 ml of methanol and 5 ml of water, 1 g of O-methylhydroxylamine hydrochloride was added and stirred at room temperature for 15 hours. After completion of the reaction, 2 g of sodium hydroxide, 10 ml of water and 10 ml of hexane were sequentially added to the reaction solution, and the aqueous layer was taken out by a liquid separation operation.
  • the solvent of the reaction solution was distilled off under reduced pressure, 50 ml of water was added to the residue, and the mixture was washed with 50 ml of ethyl acetate.
  • Concentrated hydrochloric acid was added to the obtained aqueous layer to adjust the pH to 1, and the solid deposited in the aqueous layer was taken out by filtration and washed with water.
  • the obtained solid was dried under reduced pressure to obtain 9.0 g of the objective product as a white solid.
  • Step 2 Preparation of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxamide 1 g of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxylic acid was added to a 10 ml solution of dichloromethane. At room temperature, 0.84 g of oxalyl chloride and then 0.1 ml of N, N-dimethylformamide were added in this order. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. Tetrahydrofuran (15 ml) was added to the obtained residue, and added at 0 ° C.
  • Step 3 Preparation of 1- (tert-butyl) -5-methyl-1H-pyrazol-4-amine 5.2 g of 8 wt% aqueous sodium hypochlorite solution in 0.5 ml of water of 0.64 g of sodium hydroxide And 2 ml of water were added and cooled to 0 ° C. To the reaction solution, 0.48 g of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxamide was added and stirred at 70 ° C. for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with 10 ml of ethyl acetate.
  • Step 5 Preparation of 2- (methoxyimino) -N- (3-methyl-1H-pyrazol-4-yl) -3- (methylthio) butanamide N- ⁇ 1- (tert-butyl) -5-methyl-1H
  • a solution of 0.34 g of -pyrazol-4-yl ⁇ -2- (methoxyimino) -3- (methylthio) butanamide in 5 ml of formic acid was stirred at the reflux temperature of formic acid for 5 hours. After completion of the reaction, 5 ml of water was added to the reaction solution and extracted with 5 ml of ethyl acetate.
  • the obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with ethyl acetate to obtain 86 mg of the desired product as a pale yellow oil.
  • the obtained residue was added at room temperature to a separately prepared solution of 0.9 g of 3-chloro-1H-pyrazol-4-amine and 1.4 g of pyridine in 20 ml of dichloromethane. After the addition was complete, stirring was continued overnight. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure. To the obtained residue was added 20 ml of 1N aqueous hydrochloric acid, and the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.2 g of the desired product as a yellow oil.
  • the obtained target product was a mixture of two geometric isomers, and the isomer ratio was 2: 1.
  • Isomer ratio 2 1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) ⁇ 9.52 (brs, 1H), 8.26 (s, 1H), 4.37-4.31 (m, 1H) 4.07 (s, 3H ), 2.14 (s, 3H), 1.62 (d, J 7.5 Hz, 3H)
  • Isomer ratio 1 1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) ⁇ 9.52 (brs, 1H), 8.50 (s, 1H), 4.37-4.31 (m, 1H) 4.07 (s, 3H ), 2.17 (s, 3H), 1.58 (d, J 7.5 Hz, 3H)
  • Step 2 Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carbonyl azide 120 mg
  • the toluene 2.5 ml solution was stirred at 100 ° C. for 30 minutes. After completion of the stirring, the reaction solution was cooled to room temperature, and 1 ml of concentrated hydrochloric acid was added.
  • reaction solution was continuously stirred at room temperature for 10 minutes.
  • 10% by weight aqueous sodium hydroxide solution was added to the reaction solution to adjust the pH of the reaction solution to 11, and then extracted twice with 10 ml of ethyl acetate.
  • the obtained organic layer was washed and dried in the order of saturated brine and anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 85 mg of the desired product as a white solid. Melting point: 133-135 ° C
  • the solvent of the reaction solution was distilled off under reduced pressure, and then 40 ml of tetrahydrofuran was added to the obtained residue to dissolve it.
  • the obtained solution was added at 0 ° C. to 300 ml of a 1.5 M aqueous potassium hydroxide solution prepared separately. After completion of the addition, the reaction solution was stirred at room temperature for 3 hours. After completion of the stirring, the reaction solution was washed with 200 ml of diethyl ether, adjusted to pH 1 with concentrated hydrochloric acid, and extracted with 300 ml of ethyl acetate.
  • Step 2 Preparation of (+)-2- (methoxyimino) -3- (methylthio) pentanoic acid To a solution of 96 g of 2- (methoxyimino) -3- (methylthio) pentanoic acid synthesized in Step 1 in 288 ml of acetonitrile, quinidine 155 g and 768 ml of diisopropyl ether were added sequentially.
  • reaction solution was stirred at 65 ° C. for 5 minutes. After completion of the stirring, the reaction solution was continuously stirred at room temperature for 3 hours. After completion of the stirring, the solid precipitated in the reaction solution was filtered, and 405 ml of acetonitrile and 576 ml of diisopropyl ether were added to the obtained solid. After stirring at 65 ° C. for 5 minutes, stirring was continued at room temperature for 15 hours. The precipitated solid was filtered, 300 ml of 1M aqueous hydrochloric acid solution was added to the obtained solid, and the mixture was extracted with 300 ml of ethyl acetate.
  • Step 2 Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3-methyl-1H-pyrazol-4-amine 0.61 g of dimethyl sulfoxide in 10 ml of solution 1 g of bromopyridine, 0.24 g of copper iodide (monovalent), 3.1 g of cesium carbonate, and 0.36 g of trans-N, N′-dimethylcyclohexane-1,2-diamine were sequentially added.
  • the inside of the reaction vessel was replaced with nitrogen gas and then stirred at 140 ° C. for 14 hours.
  • the solid precipitated in the reaction mixture was filtered off.
  • 50 ml of water was added to the obtained filtrate and extracted with 100 ml of chloroform.
  • the obtained organic layer was washed with 50 ml of a 7 wt% aqueous ammonia solution and then with saturated saline, and then dehydrated and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 3: 1 to 0: 1) to obtain the desired product and its isomer 5- 276 mg of a mixture of methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine was obtained. This mixture was washed with diisopropyl ether to obtain the desired product (134 mg) as a brown solid. Melting point: 125-127 ° C
  • the obtained organic layer was washed with water and then dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 3: 1 to 0: 1) to obtain 114 mg of the desired product as a yellow solid. Melting point: 131-133 ° C
  • the obtained organic layer was dehydrated and dried in the order of saturated saline and anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure to obtain 0.8 g of the objective product as a brown oil.
  • the obtained target product was a mixture of two kinds of geometric isomers, and the isomer ratio was 3: 2.
  • Step 2 Preparation of ethyl 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoate
  • Ethyl 3- (1,3-dithian-2-yl) -2-oxopropanoate To a 20 ml solution of ethanol, 0.86 g of O-methylhydroxylamine hydrochloride was added and stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, and 30 ml of water was added to the residue, followed by extraction with 50 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 20: 1 to 4: 1) to give 2.1 g of the desired product as a pale yellow oil.
  • Gradient 20: 1 to 4: 1 grade 20: 1 to 4: 1
  • Step 3 Preparation of 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoic acid 2 g of ethyl 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoate 25 ml of water and 0.36 g of sodium hydroxide were added to a 20 ml ethanol solution and stirred at room temperature for 2 hours. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure.
  • This invention compound can be manufactured according to the said manufacturing method and an Example.
  • Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 22 are shown in Tables 5 to 11 and their physical properties are shown in Table 12.
  • the present invention is not limited to these. .
  • c-Pr and Pr-c represent cyclopropyl groups
  • c-Pen and Pen-c represent cyclopentyl groups
  • c-Hex and Hex-c represent cyclohexyl groups
  • the structures represented by ⁇ 103n, D1 ⁇ 103o, D1 ⁇ 103p, D1 ⁇ 103q, D1 ⁇ 108a, and D1 ⁇ 108b represent the following structures, and are described in the structural formulas of D1-7b, D1 ⁇ 32b, and D1 ⁇ 33b.
  • the proton nuclear magnetic resonance chemical shift values in Table 12 were measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference substance.
  • a part of the optically active form of the compound of the present invention was separated into the optically active form using high performance liquid chromatography having an optically active column. The method will be described in detail, but the present invention is not limited to these.
  • (A) Separation of optically active substance High performance liquid chromatography was manufactured by Shimadzu Corporation; 10AVP system was used. The optically active substance was separated according to the conditions described below. Flow rate: 7.0 ml / min.
  • Test Example 1 Insecticidal test against brown planthopper A 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. Rice leaf sheaths are immersed in this chemical solution for about 10 seconds, air-dried and placed in a test tube, and 5 second-instar larvae of the green planthopper (Nilaparvata lugens) are released per test tube and covered with a sponge. Housed in a constant temperature room.
  • the number of dead insects after 6 days was investigated, and the death rate (%) (number of dead insects ⁇ number of test insects ⁇ 100) was calculated.
  • the test was performed by 2 continuous systems. As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
  • Test Example 2 Insecticidal test against silver leaf whitefly A moist filter paper was laid on a 7 cm inner diameter styrol cup, and a green leaf cut into 3 cm was placed thereon. A 10% emulsion of a compound of the present invention (depending on the compound, 10% wettable powder) is diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm, and the chemical solution is prepared using a rotary spray tower. 2.5 ml was sprayed per styrene cup (2.5 mg / cm 2 ). After the leaves were air-dried, adults of silver leaf whiteflies (Bemisia argentifolii) were released, covered, and housed in a thermostatic chamber at 25 ° C. The number of dead insects after 5 days was investigated, and the dead insect rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems. As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
  • Test Example 3 Insecticidal test against peach aphid A moist absorbent cotton was laid on a glass petri dish with an inner diameter of 3 cm, and kanran leaves cut out to the same diameter were placed on it. did. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed (2.5 mg / cm 2 ), covered, and stored in a constant temperature room at 25 ° C. The number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems. As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
  • Test Example 4 Insecticidal test against cotton aphids Wet cotton wool with a 3 cm inner diameter petri dish, and a cucumber leaf cut to the same diameter was placed on it, and four cotton aphids (Aphis gossypii) adults were released.
  • a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm.
  • the chemical solution was sprayed (2.5 mg / cm 2 ), covered, and stored in a constant temperature room at 25 ° C.
  • the number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1.
  • the test was performed by 2 continuous systems. As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
  • Test Example 5 Soil irrigation treatment test for peach aphid A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm. 10 ml of the chemical solution was irrigated to the stock soil portion of the plastic cup planted cabbage seedling (2.5 true leaf stage) and left in the greenhouse. One day after the irrigation treatment, 20 mosquitoes / strain of adult peach aphid (Myzus persicae) were released and then left in the greenhouse. The number of surviving insects 6 days after the release was examined, and a control value was calculated from the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the characters in the formula represent the following: Cb: Number of insects before treatment in the untreated group Cai: Number of live insects at the time of final survey in the untreated group Tb: Number of insects before treatment in the treated group Tai: Number of live insects at the time of final survey in the treated group Results Among the compounds tested, the following compounds showed a control value of 90% or more.
  • Test Example 6 Effect test on cat fleas 3.5 mg of the compound of the present invention was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 ⁇ l of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm 2 , acetone was volatilized to form a pyrazole and thiazole derivative thin film on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm 2 , the treatment dose is 10 ⁇ g / cm 2 .
  • Test Example 7 Effect test on tick (American dog tick) 3.5 mg of the compound of the present invention was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 ⁇ l of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm 2 , acetone was volatilized to form a pyrazole and thiazole derivative thin film on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm 2 , the treatment dose is 10 ⁇ g / cm 2 .
  • novel pyrazole and thiazole derivatives in the present invention exhibit excellent pest control activity, particularly insecticidal / miticidal activity, and have almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects. It is a useful compound.

Abstract

Provided is a novel pest control agent, in particular, an insecticide or a miticide. A pyrazole or thiazole derivative represented by formula (1) or a salt thereof. (In the formula, A1 represents -N(O)m2 or -CR1; R1 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or the like; Ra represents a hydrogen atom, a C1-C6 alkyl group or the like; Rb represents -C(O)R7b or the like; R7b represents -C(=NOR11b)R12b or the like; each of R11b and R12b independently represents a C1-C6 alkyl group or the like; each of m1 and m2 independently represents an integer of 0 or 1; and n represents an integer of 0, 1, 2 or 3.)

Description

ピラゾール若しくはチアゾール誘導体又はその塩及び有害生物防除剤Pyrazole or thiazole derivatives or salts thereof and pest control agents
　本発明は、新規なピラゾール若しくはチアゾール誘導体又はその塩、及び該化合物を有効成分として含有することを特徴とする有害生物防除剤に関するものである。
　本発明における有害生物防除剤とは、農園芸分野又は畜産・衛生分野（家畜や愛玩動物としての哺乳動物又は鳥類に対する内部寄生虫・外部寄生虫や家庭用及び業務用の衛生害虫・不快害虫）等における有害な節足動物を対象とした害虫防除剤を意味する。また、本発明における農薬とは、農園芸分野における殺虫・殺ダニ剤、殺線虫剤、除草剤及び殺菌剤等を意味する。 The present invention relates to a novel pyrazole or thiazole derivative or a salt thereof, and a pest control agent characterized by containing the compound as an active ingredient.
The pest control agent in the present invention refers to the field of agriculture and horticulture or the field of livestock and hygiene (endoparasites / external parasites for mammals or birds as domestic animals and pets, hygiene pests and unpleasant pests for household and commercial use) It means a pest control agent for harmful arthropods such as The agrochemical in the present invention means an insecticide / acaricide, nematicide, herbicide, fungicide, etc. in the field of agriculture and horticulture.
　例えば、特許文献１～９及び特許文献１３～１４には、ピラゾール及びチアゾール誘導体が開示されているが、本発明に係るピラゾール及びチアゾール誘導体に関しては何ら開示されていない。さらに、その有害生物防除剤、特に殺虫・殺ダニ剤及び哺乳動物又は鳥類の内部若しくは外部寄生虫防除剤としての有用性も全く知られていない。
　また特許文献１０～１２には、ピラゾール及びチアゾール誘導体が殺虫剤として有用であることが開示されているが、本発明に係るピラゾール及びチアゾール化合物については何ら開示されていない。 For example, Patent Documents 1 to 9 and Patent Documents 13 to 14 disclose pyrazole and thiazole derivatives, but do not disclose any pyrazole and thiazole derivatives according to the present invention. Furthermore, its usefulness as a pest control agent, particularly an insecticide / acaricide, and an internal or ectoparasite control agent for mammals or birds is not known at all.
Patent Documents 10 to 12 disclose that pyrazole and thiazole derivatives are useful as insecticides, but do not disclose any pyrazole and thiazole compounds according to the present invention.
国際公開第２００７／００７８８６号International Publication No. 2007/007886 国際公開第２００９／０７６４５４号International Publication No. 2009/076454 国際公開第２００８／０４４７６７号International Publication No. 2008/044767 米国特許出願公開第２００４／２１４８３８号明細書US Patent Application Publication No. 2004/214838 日本国特許出願公開第２００３／３１３１０３号Japanese Patent Application Publication No. 2003/313103 国際公開第９９／０１０３５０号International Publication No. 99/010350 国際公開第９７／０３４８９３号International Publication No. 97/034893 日本国特許出願公開第６３／１７４９０５号Japanese Patent Application Publication No. 63/174905 日本国特許出願公開第６２／１５３２７３号Japanese Patent Application Publication No. 62/153273 国際公開第２０１２／０６１２９０号International Publication No. 2012/061290 国際公開第２０１１／１２８３０４号International Publication No. 2011/128304 国際公開第２０１０／１２９４９７号International Publication No. 2010/129497 国際公開第２００８／０９０３８２号International Publication No. 2008/090382 日本国特許出願公開第２００３／２１２８６４号Japanese Patent Application Publication No. 2003/212864
　農園芸病害虫、森林病害虫、或いは衛生病害虫等、各種病害虫の防除を目的とする有害生物防除剤の開発が進み、多種多様な薬剤が今日まで実用に供されてきた。
　しかしながら、こうした薬剤の長年にわたる使用により、近年、病害虫が薬剤抵抗性を獲得し、従来用いられてきた既存の殺虫剤や殺菌剤による防除が困難となる場面が増えてきている。また、既存の有害生物防除剤の一部のものは毒性が高く、或いはあるものは環境中に長期間残留することにより、生態系を攪乱するという問題も顕在化しつつある。このような状況下、高度な有害生物防除活性を有するのみならず、低毒性且つ低残留性の新規な有害生物防除剤の開発が常に期待されている。
　本発明の目的は、高活性で、低毒性であり、且つ低残留性の新規な有害生物防除剤を提供することである。 The development of pest control agents for the purpose of controlling various pests such as agricultural and horticultural pests, forest pests, and hygiene pests has progressed, and a wide variety of drugs have been put to practical use to date.
However, due to the long-term use of such drugs, in recent years, pests have acquired drug resistance, making it difficult to control with existing insecticides and fungicides that have been used. In addition, some existing pest control agents are highly toxic, or some of them remain in the environment for a long time, and the problem of disturbing the ecosystem is becoming apparent. Under such circumstances, development of a novel pest control agent having not only high pest control activity but also low toxicity and low persistence is always expected.
An object of the present invention is to provide a novel pesticide having high activity, low toxicity, and low persistence.
　本発明者らは、上記の課題解決を目標に鋭意研究を重ねた結果、本発明に係る下記式（１）で表される新規なピラゾール及びチアゾール誘導体が優れた有害生物防除活性、特に殺虫・殺ダニ活性を示し、且つ、哺乳動物、魚類及び益虫等の非標的生物に対してほとんど悪影響の無い、極めて有用な化合物であることを見い出し、本発明を完成した。
　すなわち、本発明は下記〔１〕～〔１０４〕に関するものである。 As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel pyrazole and thiazole derivatives represented by the following formula (1) according to the present invention have excellent pest control activity, particularly insecticide / The present invention was completed by discovering that it is a very useful compound that exhibits acaricidal activity and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.
That is, the present invention relates to the following [1] to [104].
　　〔１〕
　式（１）で表されるピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000007
 ［式中、Ａ１は、－Ｎ（－Ｏ）ｍ２又は－ＣＲ１を表し、
　Ｒ１、Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９ａ）Ｒ３０ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。 [1]
A pyrazole or thiazole derivative represented by the formula (1) or a salt thereof.
Figure JPOXMLDOC01-appb-C000007
 Wherein, A 1 is, -N (-O) m2 or represents -CR 1,
R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 3 -C 8 cycloalkyl , optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 28a (C 2 ~ C 6 ) alkenyl, C 3 ~ C 8 cycloalkenyl , optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 28a (C 2 ~ C 6 ) alkynyl, C 1 ~ C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 Alkylthio, C 1 ~ C 6 alkylsulfinyl, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkyl Aminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, -C (= NOR 29a) R 30a, Fe Represents Le, the (Z) phenyl substituted by q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q.
　Ｒ２は、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９ａ）Ｒ３０ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表し、ｎが２以上の整数を表すとき、各々のＲ２は互いに同一であっても又は互いに相異なってもよい。 R 2 represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S ( O) 2 NH 2, C 1 ~ C 6 alkyl, substituted optionally substituted with R 28a (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, optionally with R 28a (C 3 ~ C 8) cycloalkyl, C 2 ~ C 6 alkenyl, which is optionally substituted with R 28a (C 2 ~ C 6 ) alkenyl, C 3 ~ C 8 cycloalkenyl, which is optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkenyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 28a , C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 Alkylthio, C 1 -C 6 alkylsulfur Finiru, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1- C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C ( = NOR 29a ) R 30a , phenyl, (Z) pheny substituted by q , Naphthyl, naphthyl substituted by q , or any group of D1-1 to D1-99, and when n represents an integer of 2 or more, each R 2 may be the same as each other Or they may be different from each other.
　Ｂは、Ｂ－１又はＢ－２のいずれかで示される環を表す。
Figure JPOXMLDOC01-appb-C000008
 （式中、「＊」は置換基「－Ｎ（Ｒａ）Ｒｂ」との結合位置を表し、「＊＊」は下記に示した置換基との結合位置を表す。）
Figure JPOXMLDOC01-appb-C000009
 B represents a ring represented by either B-1 or B-2.
Figure JPOXMLDOC01-appb-C000008
 (In the formula, “*” represents the bonding position with the substituent “—N (R a ) R b ”, and “**” represents the bonding position with the substituent shown below.)
Figure JPOXMLDOC01-appb-C000009
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－ＯＲ６ａ、－Ｓ（Ｏ）ｒ２Ｒ６ａ、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）ＳＲ６ａ、－Ｃ（Ｓ）ＯＲ６ａ、－Ｃ（Ｓ）ＳＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｓ）Ｒ７ａ、－Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、ＲａはＲ３と一緒になってＣ２～Ｃ５のアルキレン鎖又はＣ２～Ｃ５アルケニレン鎖を形成することにより、Ｒａが結合する炭素原子及びＲ３が結合する炭素原子と共に５～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、－ＯＨ，－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１１ａ、オキソ基又はチオキソ基によって任意に置換されてもよい。 R a is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 5a (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 5a (C 2 ~ C 6) alkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 5a (C 2 ~ C 6 ) alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 5a (C 3 ~ C 8 ) Cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 5a , —OR 6a , —S (O) r 2 R 6a , —C (O) OR 6a , -C (O) SR6a , -C (S) OR6a , -C (S) SR6a , -C (O) R7a , -C (S) R7a , -N ( R8a ) R9a , —C (O) N (R 8a ) R 9a , —C (S) N (R 8a ) R 9a, -S (O) r2 N (R 8a) R 9a, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (OR 41) 2 , Phenyl, phenyl substituted by (Z) q , naphthyl, naphthyl substituted by (Z) q , or any group of D1-1 to D1-99, or R a together with R 3 To form a C 2 -C 5 alkylene chain or a C 2 -C 5 alkenylene chain to form a 5- to 8-membered ring together with the carbon atom to which R a is bonded and the carbon atom to which R 3 is bonded. In this case, the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is a halogen atom, cyano, nitro, C 1 -C 6 alkyl, —OH, —OR 11a , -SH, S (O) r R 11a, which may be optionally substituted by oxo or thioxo group.
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表すか、或いは、ＲｂはＲａと一緒になって＝Ｃ（Ｒｂ２）Ｒｂ３を形成してもよく、
　Ｒｂ２は、－ＯＲ６ａ又は－Ｓ（Ｏ）ｒ２Ｒ６ａを表し、
　Ｒｂ３は、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂ又は－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表し、
　Ｒ５ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＨ、－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）ＳＲ１１ａ、－Ｃ（Ｓ）ＯＲ１１ａ、－Ｃ（Ｓ）ＳＲ１１ａ、－Ｃ（Ｏ）Ｒ１２ａ、－Ｃ（Ｓ）Ｒ１２ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｓ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、２つのＲ５ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。 R b represents —C (O) R 7b or —C (S) R 7b , or R b together with R a may form ═C (R b2 ) R b3 ,
R b2 represents —OR 6a or —S (O) r2 R 6a ;
R b3 represents —C (= NOH) R 12b , —C (= NOR 11b ) R 12b or —C {= NN (R 13b ) R 14b } R 12b ,
R 5a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 10a , —OH, —OR 11a , —SH, —S ( O) r2 R 11a , —N (R 13a ) R 14a , —C (O) OH, —C (O) OR 11a , —C (O) SR 11a , —C (S) OR 11a , —C (S ) SR 11a , —C (O) R 12a , —C (S) R 12a , —C (O) N (R 13a ) R 14a , —C (S) N (R 13a ) R 14a , —S (O ) r2 N (R 13a) R 14a, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (OR 41) 2, phenyl, (Z) phenyl substituted by q , naphthyl, (Z) n substituted by q When R 5a is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino , C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene may be formed.
　Ｒ６ａ、Ｒ８ａ及びＲ９ａは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１０ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１０ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）ＳＲ１１ａ、－Ｃ（Ｓ）ＯＲ１１ａ、－Ｃ（Ｓ）ＳＲ１１ａ、－Ｃ（Ｏ）Ｒ１２ａ、－Ｃ（Ｓ）Ｒ１２ａ、－Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｓ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１３ａ）Ｒ１４ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ８ａはＲ９ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ８ａ及びＲ９ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つ、Ｒ４２、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
　Ｒ７ａは、Ｒ６ａ、－Ｃ（＝ＮＲ１３ａ）Ｒ１２ａ、－Ｃ（＝ＮＯＨ）Ｒ１２ａ、－Ｃ（＝ＮＯＲ１１ａ）Ｒ１２ａ又は－Ｃ｛＝ＮＮ（Ｒ１３ａ）Ｒ１４ａ｝Ｒ１２ａを表し、
　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂ又は－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表し、
　Ｒ１０ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１０ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。 R 6a , R 8a and R 9a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 10a , C 2 -C 6 alkenyl, R 10a in optionally substituted (C 2 ~ C 6) alkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 10a (C 2 ~ C 6) alkynyl, C 3 ~ C 8 cycloalkyl, with R 10a Optionally substituted (C 3 -C 8 ) cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 10a , —S (O) r2 R 11a , -C (O) OR 11a , -C (O) SR 11a , -C (S) OR 11a , -C (S) SR 11a , -C (O) R 12a , -C (S) R 12a , -N (R 13a ) R 14a , —C (O) N (R 13a ) R 14a , —C (S) N (R 13a ) R 14a , —S (O) r 2 N (R 13a ) R 14a , phenyl, phenyl substituted by (Z) q , naphthyl, ( Z) represents naphthyl substituted by q or any group of D1-1 to D1-99, or R 8a together with R 9a represents a C 2 -C 7 alkylene chain or C 2 -C 7 to form a 3- to 8-membered ring together with the nitrogen atom to which R 8a and R 9a are bonded, and this alkylene chain or alkenylene chain is an oxygen atom, sulfur atom or nitrogen atom. And may be optionally substituted with a (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 10a .
R 7a is R 6a , -C (= NR 13a ) R 12a , -C (= NOH) R 12a , -C (= NOR 11a ) R 12a or -C {= NN (R 13a ) R 14a } R 12a Represents
R 7b represents -C (= NOH) R 12b , -C (= NOR 11b ) R 12b or -C {= NN (R 13b ) R 14b } R 12b
R 10a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 11a , —SH, —S (O) r 2 R 11a , —P ( Represents O) (OR 41 ) 2 , —P (S) (OR 41 ) 2 or —Si (R 40a ) (R 40b ) R 40 , or two R 10a are substituted on the same carbon If present, the two R 5a may be taken together to form an oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
　Ｒ１１ａ及びＲ１２ａは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ２Ｒ１６ａ、－Ｃ（Ｏ）ＯＲ１６ａ、－Ｃ（Ｏ）ＳＲ１６ａ、－Ｃ（Ｓ）ＯＲ１６ａ、－Ｃ（Ｓ）ＳＲ１６ａ、－Ｃ（Ｏ）Ｒ１７ａ、－Ｃ（Ｓ）Ｒ１７ａ、－Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｃ（Ｏ）Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｃ（Ｓ）Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
　Ｒ１１ｂは、Ｃ１～Ｃ１０アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。 R 11a and R 12a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkenyl, optionally with R 15a substituted (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15a (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15a Substituted (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15a , —S (O) r 2 R 16a , —C ( O) OR 16a , -C (O) SR 16a , -C (S) OR 16a , -C (S) SR 16a , -C (O) R 17a , -C (S) R 17a , -N (R 18a ) R 19a, -C (O) N ( 18a) R 19a, -C (S ) N (R 18a) R 19a, -S (O) r2 N (R 18a) R 19a, -Si (R 40a) (R 40b) R 40, phenyl, (Z) Phenyl substituted by q , naphthyl, (Z) naphthyl substituted by q , or any group of D1-1 to D1-99.
R 11b is substituted C 1 ~ C 10 alkyl, optionally with R 15b (C 1 ~ C 6 ) alkyl, optionally substituted with C 2 ~ C 6 alkenyl, R 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, optionally substituted with C 2 ~ C 6 alkynyl, R 15b (C 2 ~ C 6) Alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r 3 R 16b , —C (O) OR 16b , —C (O) SR 16b , -C (S) OR 16b , -C (S) SR 16b , -C (O) R 17b , -C (S) R 17b , -C (O) N (R 18b ) R 19b , -C (S) N (R 18b) R 19b, - (O) represents the r3 N (R 18b) R 19b , phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q .
　Ｒ１２ｂは、水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）ＳＲ１６ｃ、－Ｃ（Ｓ）ＯＲ１６ｃ、－Ｃ（Ｓ）ＳＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｓ）Ｒ１７ｃ、－Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｓ（Ｏ）ｒＮ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（＝ＮＯＨ）Ｒ１７ｃ、－Ｃ（＝ＮＯＲ１６ｃ）Ｒ１７ｃ、－Ｃ｛＝ＮＮ（Ｒ１８ｃ）Ｒ１９ｃ｝Ｒ１７ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
　Ｒ１３ａ及びＲ１４ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表すか、或いは、Ｒ１３ａはＲ１４ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ａ及びＲ１４ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＲ４２、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。 R 12b is a hydrogen atom, a halogen atom, substituted cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , -C (O) SR 16c , -C (S) OR 16c , -C (S) SR 16c , -C (O) R 17c , -C (S) R 17c , -N (R 18c) R 19c, -C ( ) N (R 18c) R 19c , -C (S) N (R 18c) R 19c, -S (O) r N (R 18c) R 19c, -C (= NOH) R 17c, -C (= NOR 16c) R 17c, -C {= NN (R 18c) R 19c} R 17c, phenyl, (Z) phenyl substituted by q, naphthyl, (Z) naphthyl or substituted by q D1-1 ~ D1- Any one of 99 groups is represented.
R 13a and R 14a each independently represent a hydrogen atom or C 1 -C 6 alkyl, or R 13a together with R 14a is a C 2 -C 7 alkylene chain or C 2 -C 7. To form a 3- to 8-membered ring together with the nitrogen atom to which R 13a and R 14a are bonded. In this case, the alkylene chain or alkenylene chain has an oxygen atom, a sulfur atom or a nitrogen atom. One may be included, and optionally substituted by a (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 15a .
　Ｒ１３ｂは、水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つＲ４２、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。 R 13b is a hydrogen atom, cyano, substituted nitro, C 1 ~ C 6 alkyl, optionally substituted with R 15b (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally with R 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15b (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —OR 16b , —S (O) r3 R 16b , —C (O) OR 16b , -C (O) SR 16b , -C (S) OR 16b , -C (S) SR 16b , -C (O) R 17b , -C (S) R 17b , -C (O ) N (R 18b) R 19b , C (S) N (R 18b ) R 19b, -S (O) r3 N (R 18b) R 19b, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (oR 41) 2, or represents phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any group of naphthyl or D1-1 ~ D1-99 replaced by q Alternatively, R 13b together with R 14b forms a C 2 to C 7 alkylene chain or a C 2 to C 7 alkenylene chain to form a 3 to 8 together with the nitrogen atom to which R 13b and R 14b are attached. In this case, the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with R 42 or R 15b (C 1 ~ C 6 Alkyl may be optionally substituted by oxo or thioxo group.
　Ｒ１４ｂは、水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｄで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｄで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｄで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｄで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｄで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｄ、－Ｓ（Ｏ）ｒ３Ｒ１６ｄ、－Ｃ（Ｏ）ＯＲ１６ｄ、－Ｃ（Ｏ）ＳＲ１６ｄ、－Ｃ（Ｓ）ＯＲ１６ｄ、－Ｃ（Ｓ）ＳＲ１６ｄ、－Ｃ（Ｏ）Ｒ１７ｄ、－Ｃ（Ｓ）Ｒ１７ｄ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよい。
　Ｒ１４ｅ及びＲ１４ｆは、各々独立して水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１４ｅはＲ１４ｆと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１４ｅ及びＲ１４ｆが結合する炭素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１、２又は３個含んでもよく、且つＲ４２、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。 R 14b is a hydrogen atom, cyano, substituted nitro, C 1 ~ C 6 alkyl, optionally substituted with R 15d (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally with R 15d (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15d (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15d (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15d , —OR 16d , —S (O) r3 R 16d , —C (O) OR 16d , -C (O) SR 16d , -C (S) OR 16d , -C (S) SR 16d , -C (O) R 17d , -C (S) R 17d , -C (O ) N (R 18d) R 19d , C (S) N (R 18d ) R 19d, -S (O) r3 N (R 18d) R 19d, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (oR 41) 2, or represents phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any group of naphthyl or D1-1 ~ D1-99 replaced by q Alternatively, R 14b may be combined with R 13b to form ═C (R 14e ) R 14f .
R 14e and R 14f are each independently a hydrogen atom, cyano, nitro, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, R optionally substituted with 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, R optionally substituted with 15b (C 2 ~ C 6) alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkyl, -OR 16b, -S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (S) OR 16b, -C (S) SR 16b, -C (O) R 17b, -C (S) R 17b, -C (O) N R 18b) R 19b, -C ( S) N (R 18b) R 19b, -S (O) r3 N (R 18b) R 19b, -Si (R 40a) (R 40b) R 40, -P (O ) (oR 41) 2, -P (S) (oR 41) 2, phenyl, (Z) phenyl substituted by q, naphthyl, naphthyl or D1-1 ~ D1-99 substituted by (Z) q R 14e and R 14f are bonded by representing any group or R 14e together with R 14f to form a C 2 to C 7 alkylene chain or a C 2 to C 7 alkenylene chain. A 3- to 8-membered ring may be formed together with the carbon atom, and this alkylene chain or alkenylene chain may contain 1, 2 or 3 oxygen atoms, sulfur atoms or nitrogen atoms, and R 42 , R 15b At Substituted in (C 1 ~ C 6) alkyl, it may be optionally substituted by oxo or thioxo group.
　Ｒ１５ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ａ、－ＳＨ、－Ｓ（Ｏ）ｒ2Ｒ１６ａ、－Ｓ（＝ＮＲ１８ａ）Ｒ１６ａ、－Ｓ（Ｏ）（＝ＮＲ１８ａ）Ｒ１６ａ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
　Ｒ１５ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｂ、－ＳＨ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｓ（＝ＮＲ１８ｂ）Ｒ１６ｂ、－Ｓ（Ｏ）（＝ＮＲ１８ｂ）Ｒ１６ｂ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（＝ＮＯＲ１６ｂ）Ｒ１７ｂ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｂが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。 R 15a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16a , —SH, —S (O) r 2 R 16a , —S ( ═NR 18a ) R 16a , —S (O) (═NR 18a ) R 16a , —P (O) (OR 41 ) 2 , —P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15a is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene Shape It may be.
R 15b is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16b , —SH, —S (O) r 3 R 16b , —S ( = NR 18b ) R 16b , -S (O) (= NR 18b ) R 16b , -C (O) OH, -C (O) OR 16b , -C (O) R 17b , -C (O) N ( R 18b ) R 19b , -C (= NOR 16b ) R 17b , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, phenyl substituted by (Z) q , Naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R 15b are the same When substituted on carbon, two R 5a together may form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
　Ｒ１５ｃは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｓ（＝ＮＲ１８ｃ）Ｒ１６ｃ、－Ｓ（Ｏ）（＝ＮＲ１８ｃ）Ｒ１６ｃ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｃが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
　Ｒ１５ｄは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｄ、－ＳＨ、－Ｓ（Ｏ）ｒ３Ｒ１６ｄ、－Ｓ（＝ＮＲ１８ｄ）Ｒ１６ｄ、－Ｓ（Ｏ）（＝ＮＲ１８ｄ）Ｒ１６ｄ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｄが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよく、
　Ｒ１６ａ、Ｒ１６ｂ、Ｒ１６ｃ及びＲ１６ｄは、各々独立してシアノ、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｓ（Ｏ）ｒＲ２１、－Ｃ（Ｏ）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。 R 15c is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16c , —SH, —S (O) r R 16c , —S ( = NR 18c ) R 16c , -S (O) (= NR 18c ) R 16c , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15c is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene Shape It may be.
R 15d is a halogen atom, cyano, nitro, C 3 to C 8 cycloalkyl, C 3 to C 8 halocycloalkyl, —OH, —OR 16d , —SH, —S (O) r 3 R 16d , —S ( = NR 18d ) R 16d , -S (O) (= NR 18d ) R 16d , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15d is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene The It may form,
R 16a , R 16b , R 16c and R 16d are each independently cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -S (O) r R 21 represents -C (O) R 22, phenyl, phenyl substituted by (Z) q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q.
　Ｒ１７ａ、Ｒ１７ｂ、Ｒ１７ｃ及びＲ１７ｄは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
　Ｒ１８ａ及びＲ１９ａは、各々独立して水素原子，シアノ又はＣ１～Ｃ６アルキルを表し、
　Ｒ１８ｂ、Ｒ１９ｂ、Ｒ１８ｄ及びＲ１９ｄは、各々独立して水素原子，シアノ、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１８ｂはＲ１９ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１８ｂ及びＲ１９ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つＲ４２、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。 R 17a , R 17b , R 17c and R 17d are each independently a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 ( C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -C (O) R 22, -C (= NOR 21) R 22, phenyl, (Z) phenyl substituted by q, naphthyl, (Z) naphthyl substituted by q, or any group of D1-1 ~ D1-99 To express.
R 18a and R 19a each independently represents a hydrogen atom, cyano or C 1 -C 6 alkyl;
R 18b , R 19b , R 18d and R 19d are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl , C 3 ~ C 8 cycloalkenyl, optionally substituted optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally with R 20 and (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, phenyl, (Z ) Phenyl substituted by q , naphthyl, (Z) naphthyl substituted by q or any group of D1-1 to D1-99, or R 18b together with R 19b represents C 2 By forming a C 7 alkylene chain or a C 2 -C 7 alkenylene chain, a 3- to 8-membered ring may be formed together with the nitrogen atom to which R 18b and R 19b are bonded. The alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 20 May be.
　Ｒ１８ｃ及びＲ１９ｃは、各々独立して水素原子，シアノ、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－ＯＲ２１、－Ｓ（Ｏ）ｒＲ２１、－Ｃ（Ｏ）ＯＲ２１、－Ｃ（Ｏ）Ｒ２２、－Ｃ（Ｓ）Ｒ２２、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
　Ｒ２０は、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＲ２１、フェニル又は（Ｚ）ｑによって置換されたフェニルを表すか、或いは、２つのＲ２０が同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよく、
　Ｒ２１及びＲ２２は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６ハロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
　Ｄ１－1～Ｄ１－９９は、それぞれ以下の構造で表される環を表す。 R 18c and R 19c are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , —OR 21 , —S (O) r R 21 , —C (O) OR 21 , —C (O) R 22 , —C (S) R 22 , phenyl or phenyl substituted by (Z) q ;
R 20 is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, —C (O) OR 21 , phenyl or phenyl substituted by (Z) q , or when two R 20 are substituted on the same carbon, R 5a together may form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene;
R 21 and R 22 each independently represent a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, phenyl or phenyl substituted by (Z) q .
D1-1 to D1-99 each represent a ring represented by the following structure.
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
　Ｘ１及びＸ１ｂは、各々独立してハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６ハロアルケニル、Ｃ２～Ｃ６ハロアルキニル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
　ｇ１、ｇ２又はｇ４が２以上の整数を表すとき、各々のＸ１は互いに同一であっても又は互いに相異なってもよく、更に２つのＸ１が隣接する場合には、隣接する２つのＸ１は、－ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＯＣＨ２－，－ＯＣＨ２Ｏ－，－ＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＳＣＨ２－，－ＣＨ２ＣＨ２Ｎ（Ｘ１ａ）－，－ＣＨ２Ｎ（Ｘ１ａ）ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＣＨ２ＯＣＨ２－，－ＣＨ２ＯＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＣＨ＝ＣＨ－，－ＯＣＨ＝ＣＨ－，－ＳＣＨ＝ＣＨ－，－Ｎ（Ｘ１ａ）ＣＨ＝ＣＨ－，－ＯＣＨ＝Ｎ－，－ＳＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）ＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）Ｎ＝ＣＨ－，－ＯＣＨ２ＣＨ＝ＣＨ－，－ＣＨ＝ＣＨＣＨ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＸ１が結合する炭素原子と共に５員環又は６員環を形成してもよく、このとき環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよく、或いは、ｆ１、ｆ２、ｆ４、ｆ５、ｆ６、ｆ７、ｆ８又はｆ９が２以上の整数を表すとき、各々のＸ１ｂは互いに同一であっても又は互いに相異なってもよく、さらに、２つのＸ１ｂが同一の炭素上に置換している場合、２つのＸ１ｂは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。 X 1 and X 1b are each independently a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S ) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl C 3 -C 8 cycloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 ~ C 6 alkylthio, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 alkylsulfinyl, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl, C 1 ~ C 6 haloalkylcarbonyl, C 3 ~ C 8 halocycloalkyl carbonyl, C 1 ~ C 6 alkoxycarbonyl, C 1 ~ C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with a halogen atom.
When g1, g2, or g4 represents an integer of 2 or more, each X 1 may be the same as or different from each other, and when two X 1 are adjacent, two adjacent X 1 represents —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —CH 2 CH 2 N (X 1a ) —, —CH 2 N (X 1a ) CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 -, -CH 2 OCH 2 O-, -OCH 2 CH 2 O-, -OCH 2 CH 2 S-, -CH 2 CH = CH-, -OCH = CH-, -SCH = CH-, -N (X 1a ) CH═CH—, —OCH═N—, —SCH═N—, —N (X 1 a ) CH = N-, -N (X 1a ) N = CH-, -OCH 2 CH = CH-, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, Forming —N═NCH═CH—, —CH═NN═CH—, —N═CHCH═N—, or —N═CHN═CH—, together with the carbon atom to which each X 1 is attached is a 5-membered ring Or a hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group , C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group or C 1 -C 6 alkylsulfonyl group, or f1, f2, f4 , F5, f6, f7, f Or when f9 represents an integer of 2 or more, each X 1b or different are or phase from each other be identical to each other, further, when two which X 1b are substituted on the same carbon, the two X 1b may be taken together to form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
　Ｘ１ａは、水素原子、シアノ、－ＯＨ、－ＮＨ２、－ＣＨＯ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２８で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２８で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２８で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２８で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
　Ｘ１ａの隣接位にＸ１が存在する場合には、隣接するＸ１ａとＸ１は、－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－、－ＣＨ＝ＣＨＣＨ＝ＣＨ－、－Ｎ＝ＣＨＣＨ＝ＣＨ－、－ＣＨ＝Ｎ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－Ｎ＝ＣＨ－又は－ＣＨ＝ＣＨ－ＣＨ＝Ｎ－を形成することにより、Ｘ１ａ及びＸ１のそれぞれが結合する原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合する水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよい。 X 1a is a hydrogen atom, cyano, —OH, —NH 2 , —CHO, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl. , C 2 ~ C 6 alkenyl, C 2 ~ C 6 alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 28 (C 1 ~ C 6 ) alkyl, optionally substituted with R 28 (C 2 ~ C 6) alkenyl, optionally substituted with R 28 (C 2 ~ C 6 ) alkynyl, optionally substituted with R 28 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 28 (C 3 -C 8 ) cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl, C 1 ~ C 6 haloalkylcarbonyl, C 3 ~ C 8 halocycloalkyl carbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, optionally substituted with C 1 -C 6 alkyl Represents a substituted phenyl or a phenyl optionally substituted with a halogen atom.
When X 1 is present at the adjacent position of X 1a , adjacent X 1a and X 1 are —CH 2 CH 2 CH 2 CH 2 —, —CH═CHCH═CH—, —N═CHCH═CH— , —CH═N—CH═CH—, —CH═CH—N═CH—, or —CH═CH—CH═N— to form a six-membered atom together with the atoms to which each of X 1a and X 1 is attached. A hydrogen atom bonded to each carbon atom forming the ring may be a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 It may be optionally substituted with a 1 to C 6 alkoxy group, a C 1 to C 6 alkylthio group, a C 1 to C 6 alkylsulfinyl group or a C 1 to C 6 alkylsulfonyl group.
　Ｚは、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６ハロアルケニル、Ｃ２～Ｃ６ハロアルキニル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
　ｑが２以上の整数を表すとき、各々のＺは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺが隣接する場合には、隣接する２つのＺは－ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＯＣＨ２－，－ＯＣＨ２Ｏ－，－ＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＳＣＨ２－，－ＣＨ２ＣＨ２Ｎ（Ｘ１ａ）－，－ＣＨ２Ｎ（Ｘ１ａ）ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＣＨ２ＯＣＨ２－，－ＣＨ２ＯＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＣＨ＝ＣＨ－，－ＯＣＨ＝ＣＨ－，－ＳＣＨ＝ＣＨ－，－Ｎ（Ｘ１ａ）ＣＨ＝ＣＨ－，－ＯＣＨ＝Ｎ－，－ＳＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）ＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）Ｎ＝ＣＨ－，－ＯＣＨ２ＣＨ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺが結合する炭素原子と共に５員環又は６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよい。 Z represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O ) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl optionally substituted with R 28 , C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkyl Aminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with a halogen atom.
When q represents an integer of 2 or more, each Z may be the same as or different from each other. Furthermore, when two Zs are adjacent to each other, the two adjacent Zs are —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —CH 2 CH 2 N (X 1a ) —, —CH 2 N (X 1a ) CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —CH 2 CH═CH—, —OCH═CH—, —SCH═CH—, —N (X 1a ) CH═CH—, -OCH = N -, - SCH = N -, - N (X 1a) CH = N -, - N ( 1a) N = CH -, - OCH 2 CH = CH -, - N = CHCH = CH -, - CH = NCH = CH -, - N = NCH = CH -, - CH = NN = CH -, - N = By forming CHCH═N— or —N═CHN═CH—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. The hydrogen atom bonded to the carbon atom is a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group, C 1 it may be optionally substituted by ~ C 6 alkylsulfinyl group or a C 1 ~ C 6 alkylsulfonyl group.
　Ｒ２８、Ｒ２８ａ、Ｒ３１及びＲ３２は、各々独立してハロゲン原子、－ＯＨ、－ＳＨ、－ＮＨ２、－ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
　Ｒ２９及びＲ２９ａは、各々独立してＣ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ３１で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ３１で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ３１で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ３１で任意に置換された（Ｃ３～Ｃ８）シクロアルキル又はＲ３１で任意に置換された（Ｃ３～Ｃ８）シクロアルケニルを表す。
　Ｒ３０及びＲ３０ａは、各々独立してＣ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ３２で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ３２で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ３２で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ３２で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ３２で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。 R 28 , R 28a , R 31 and R 32 are each independently a halogen atom, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2, -S ( O) 2 NH 2, -Si (R 40a) (R 40b) R 40, C 1 ~ C 6 alkoxy, C 1 ~ C 6 haloalkoxy, C 1 ~ C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 Haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C Represents 6 alkylamino, di (C 1 -C 6 alkyl) amino, phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with halogen atoms.
R 29 and R 29a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 31 (C 1 -C 6 ) alkyl optionally substituted with R 31 , (C 2 -C 6 ) alkenyl optionally substituted with R 31 , (C 2 -C 6 ) alkynyl optionally substituted with R 31 , R optionally substituted with 31 representing the (C 3 ~ C 8) optionally substituted cycloalkyl, or R 31 (C 3 ~ C 8 ) cycloalkenyl.
R 30 and R 30a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 32 (C 1 -C 6 ) alkyl optionally substituted with R 32 , (C 2 -C 6 ) alkenyl optionally substituted with R 32 , (C 2 -C 6 ) alkynyl optionally substituted with R 32 , R optionally substituted with 32 (C 3 ~ C 8) cycloalkyl, optionally substituted with R 32 (C 3 ~ C 8 ) cycloalkenyl, phenyl, phenyl optionally substituted with C 1 ~ C 6 alkyl Alternatively, it represents phenyl optionally substituted with a halogen atom.
　Ｒ４０、Ｒ４０ａ及びＲ４０ｂは、各々独立してＣ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
　Ｒ４１は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ４２は、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
　ｇ１、ｆ１及びｎは、各々独立して０、１、２又は３の整数を表し、
　ｇ２及びｆ２は、各々独立して０、１又は２の整数を表し、
　ｇ３は、０又は１の整数を表し、
　ｇ４及びｆ４は、各々独立して０、１、２、３又は４の整数を表し、
　ｆ５は、０、１、２、３、４又は５の整数を表し、
　ｆ６は、０、１、２、３、４、５又は６の整数を表し、
　ｆ７は、０、１、２、３、４、５、６又は７の整数を表し、
　ｆ８は、０、１、２、３、４、５、６、７又は８の整数を表し、
　ｆ９は、０、１、２、３、４、５、６、７、８又は９の整数を表し、
　ｑは、１、２、３、４又は５の整数を表し、
　ｍ１、ｍ２及びｍ３は、各々独立して０又は１の整数を表し、
　ｒ、ｒ２及びｒ３は、各々独立して０、１又は２の整数を表す。］ R 40, R 40a and R 40b are each independently C 1 to ~ C 6 alkyl, C 1 ~ C 6 alkoxy or phenyl,
R 41 represents C 1 -C 6 alkyl,
R 42 represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C Represents 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, phenyl or phenyl substituted by (Z) q .
g1, f1 and n each independently represent an integer of 0, 1, 2 or 3;
g2 and f2 each independently represent an integer of 0, 1 or 2;
g3 represents an integer of 0 or 1,
g4 and f4 each independently represent an integer of 0, 1, 2, 3 or 4;
f5 represents an integer of 0, 1, 2, 3, 4 or 5,
f6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
f8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
q represents an integer of 1, 2, 3, 4 or 5;
m1, m2 and m3 each independently represent an integer of 0 or 1,
r, r2 and r3 each independently represents an integer of 0, 1 or 2. ]
　　〔２〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１、Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル又はＣ１～Ｃ６アルキルカルボニルを表し、
　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｂは、Ｂ－１を表す上記〔１〕に記載のピラゾール誘導体又はその塩。
　　〔３〕
　Ａ１は、－Ｎ（－Ｏ）ｍ２を表し、
　Ｂは、Ｂ－１を表し、
　Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｂは、Ｂ－１を表す上記〔１〕に記載のピラゾール誘導体又はその塩。
　　〔４〕
　Ｂは、Ｂ－２を表し、
　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）ＳＲ１６ｃ、－Ｃ（Ｓ）ＯＲ１６ｃ、－Ｃ（Ｓ）ＳＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｓ）Ｒ１７ｃ、－Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ又は－Ｃ（Ｓ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃを表す上記〔１〕に記載のチアゾール誘導体又はその塩。 [2]
A 1 represents -CR 1
R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 2 -C 6 alkynyl , (C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl optionally substituted with R 28a ,
R 2 represents a halogen atom or C 1 -C 6 alkyl,
B is a pyrazole derivative or a salt thereof according to the above [1], wherein B represents B-1.
[3]
A 1 represents -N (-O) m2 ,
B represents B-1,
R 3 and R 4 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl;
R 2 represents a halogen atom or C 1 -C 6 alkyl,
B is a pyrazole derivative or a salt thereof according to the above [1], wherein B represents B-1.
[4]
B represents B-2,
R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, substituted C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 —C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , —C (O) SR 16c , —C (S) OR 16c , —C (S) SR 16c , —C (O) R 17c , —C (S) R 17c , —N (R 18c ) R 19c , —C (O) N (R 18 c ) The thiazole derivative or a salt thereof according to the above [1], which represents R 19c or —C (S) N (R 18c ) R 19c .
　　〔５〕
　Ｒ１は、水素原子又はハロゲン原子を表し、
　Ｒ２は、ハロゲン原子を表し、
　Ｒ３は、水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル又はＣ１～Ｃ６アルキルカルボニルを表し、
　Ｒ４は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ６ａ、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ又は－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａを表す。
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表すか、或いは、ＲｂはＲａと一緒になって＝Ｃ（Ｒｂ２）Ｒｂ３を形成してもよく、
　Ｒｂ２は、－ＯＲ６ａを表し、
　Ｒｂ３は、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表し、
　Ｒ５ａは、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３又はＤ１－３４を表し、
　Ｒ６ａは、Ｃ１～Ｃ６アルキル又はＲ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ７ａは、Ｃ１～Ｃ６アルキル、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル又は－Ｃ（＝ＮＯＲ１１ａ）Ｒ１２ａを表し、
　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ又は－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表し、
　Ｒ８ａは、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ９ａは、水素原子又はＣ１～Ｃ６アルキルを表す。 [5]
R 1 represents a hydrogen atom or a halogen atom,
R 2 represents a halogen atom,
R 3 represents a hydrogen atom, a halogen atom, substituted C 1 ~ C 6 alkyl, optionally substituted with R 28a (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkynyl, optionally with R 28a ( C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl,
R 4 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) represents an r2 R 6a, -C (O) oR 6a, -C (O) R 7a, -C (O) N (R 8a) R 9a or -C (S) N (R 8a ) R 9a.
R b represents —C (O) R 7b or —C (S) R 7b , or R b together with R a may form ═C (R b2 ) R b3 ,
R b2 represents —OR 6a ;
R b3 represents -C (= NOR 11b ) R 12b ,
R 5a is cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a , —S (O) r 2 R 11a , —C (O) OH, —C (O) OR 11a , —C (O) N (R 13a ) R 14a , phenyl, phenyl substituted by (Z) q , D1-32, D1-33 or D1-34;
R 6a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 10a ,
R 7a represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 10a or —C (═NOR 11a ) R 12a ,
R 7b represents -C (= NOH) R 12b or -C (= NOR 11b ) R 12b ;
R 8a represents a hydrogen atom or C 1 -C 6 alkyl;
R 9a represents a hydrogen atom or C 1 -C 6 alkyl.
　Ｒ１０ａは、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ１６ａ、－Ｃ（Ｏ）Ｒ１７ａ、－Ｃ（Ｏ）Ｎ（Ｒ１８ａ）Ｒ１９ａ又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
　Ｒ１１ｂは、Ｃ１～Ｃ７アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ１６ｂ又は－Ｃ（Ｏ）Ｒ１７ｂを表し、
　Ｒ１２ａは、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（＝ＮＯＲ１６ｃ）Ｒ１７ｃ、－Ｃ｛＝ＮＮ（Ｒ１８ｃ）Ｒ１９ｃ｝Ｒ１７ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－２、Ｄ１－３２又はＤ１－３４を表す。
　Ｒ１３ａ及びＲ１４ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ１５ａは、－ＯＲ１６ａ、－Ｓ（Ｏ）ｒ２Ｒ１６ａ、フェニル又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
　Ｒ１５ｂは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＨ、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（＝ＮＯＲ１６ｂ）Ｒ１７ｂ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３３又はＤ１－８４を表し、
　Ｒ１５ｃは、ハロゲン原子、シアノ、－ＯＨ、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
　Ｒ１６ａは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル又は－Ｎ（Ｒ２３）Ｒ２４を表す。 R 10a represents —OR 11a or —S (O) r2 R 11a ;
R 11a is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkynyl, -C (O) OR 16a , -C (O) R 17a , —C (O) N (R 18a ) R 19a or —Si (R 40a ) (R 40b ) R 40 ,
R 11b is C 1 -C 7 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted with R 15b , -C (O) OR 16b or Represents -C (O) R 17b ,
R 12a represents (C 1 -C 6 ) alkyl optionally substituted with R 15a ,
R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, optionally substituted with C 2 ~ C 6 alkenyl, R 15c (C 2 ~ C 6) alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkynyl, optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkyl, -S (O) r R 16c , -C (O) OR 16c , -C (O) R 17c , -C (O) N (R 18c ) R 19c , -C (= NOR 16c ) R 17c , -C {= NN (R 18c ) R 19c } R 17c , phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34.
R 13a and R 14a each independently represents a hydrogen atom or C 1 -C 6 alkyl;
R 15a represents —OR 16a , —S (O) r2 R 16a , phenyl or —Si (R 40a ) (R 40b ) R 40 ,
R 15b is a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 16b , —S (O) r3 R 16b , —C (O) OH, —C (O) OR 16b , —C (O) represents N (R 18b ) R 19b , —C (═NOR 16b ) R 17b , (Z) q , phenyl substituted by q , D1-33 or D1-84,
R 15c represents a halogen atom, cyano, —OH, —OR 16c , —S (O) r R 16c , phenyl, phenyl substituted by (Z) q , D1-7, D1-87 or D1-98. ,
R 16a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 16b represents C 1 -C 6 alkyl or —N (R 23 ) R 24 .
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｓ（Ｏ）ｒＲ２１、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
　Ｒ１７ａは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
　Ｒ１７ｂは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１７ｃは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１８ａ及びＲ１９ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ１８ｂは、水素原子を表すか、或いは、Ｒ１８ｂはＲ１９ｂと一緒になってＣ５のアルキレン鎖を形成することにより、Ｒ１８ｂ及びＲ１９ｂが結合する窒素原子と共に６員環を形成してもよく、このときこのアルキレン鎖は酸素原子を１個含んでもよく、
　Ｒ１８ｃは、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ２２を表し、
　Ｒ１９ｂは、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１９ｃは、水素原子を表す。
　Ｒ２０は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
　Ｒ２１は、（Ｚ）ｑによって置換されたフェニルを表し、
　Ｒ２２は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ２３及びＲ２４は、水素原子を表し、
　Ｘ１は、ハロゲン原子又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ２８は、ハロゲン原子を表し、
　Ｒ２８ａは、ハロゲン原子又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
　Ｚは、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
　Ｒ４０、Ｒ４０ａ及びＲ４０ｂは、各々独立してＣ１～Ｃ６アルキルを表す。
　ｇ１、ｇ４、ｍ１及びｎは、各々独立して０又は1の整数を表し、
　ｆ５、ｆ７及びｍ３は、０を表し、
　ｑは、１の整数を表し、
　ｒ及びｒ３は、各々独立して０、１又は２の整数を表し、
　ｒ２は、０又は２の整数を表す上記〔２〕に記載のピラゾール誘導体又はその塩。 R 16c is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , -S (O) r R 21 , (Z) represents phenyl or D1-32 substituted by q ;
R 17a represents C 1 -C 6 alkyl or phenyl;
R 17b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 17c represents C 1 -C 6 alkyl;
R 18a and R 19a each independently represent C 1 -C 6 alkyl;
R 18b represents a hydrogen atom, or R 18b together with R 19b forms a C 5 alkylene chain to form a 6-membered ring with the nitrogen atom to which R 18b and R 19b are bonded. In this case, the alkylene chain may contain one oxygen atom,
R 18c represents C 1 -C 6 alkyl or —C (O) R 22 ,
R 19b represents (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 19c represents a hydrogen atom.
R 20 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
R 21 represents phenyl substituted by (Z) q ;
R 22 represents C 1 -C 6 alkyl;
R 23 and R 24 represent a hydrogen atom,
X 1 represents a halogen atom or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
R 28 represents a halogen atom,
R 28a represents a halogen atom or —Si (R 40a ) (R 40b ) R 40 ;
Z represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
R 40 , R 40a and R 40b each independently represent C 1 -C 6 alkyl.
g1, g4, m1 and n each independently represent an integer of 0 or 1,
f5, f7 and m3 represent 0;
q represents an integer of 1;
r and r3 each independently represents an integer of 0, 1 or 2;
r2 represents 0 or an integer of 2; the pyrazole derivative or the salt thereof according to [2] above.
　　〔６〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１及びＲ３は、各々独立して水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル又はＲ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキルを表す上記〔４〕に記載のチアゾール誘導体又はその塩。 [6]
A 1 represents -CR 1
R 1 and R 3 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl;
R 2 represents a halogen atom or C 1 -C 6 alkyl,
R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, substituted C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 The thiazole derivative or a salt thereof according to the above [4], which represents (C 3 -C 8 ) cycloalkyl optionally substituted with —C 6 ) alkynyl, C 3 -C 8 cycloalkyl or R 15c .
　　〔７〕
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ又は－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａを表すか、或いは、ＲａはＲ３と一緒になってＣ２～Ｃ４のアルキレン鎖を形成することにより、Ｒａが結合する窒素原子及びＲ３が結合する炭素原子と共に５～７員環を形成してもよく、
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表し、
　Ｒ５ａは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
　Ｒ６ａ及びＲ７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ８ａ及びＲ９ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、－Ｃ（Ｏ）ＯＲ１６ａ又は－Ｃ（Ｏ）Ｒ１７ａを表す。
　Ｒ１１ｂは、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル又はＣ２～Ｃ６アルキニルを表し、
　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表し、
　Ｒ１３ｂ及びＲ１４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４～Ｃ６のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５～７員環を形成してもよい。 [7]
R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) OR 6a , —C (O) R 7a , —C (O) N (R 8a ) R 9a or —C (S) N (R 8a ) R 9a , or R a together with R 3 And forming a C 2 -C 4 alkylene chain to form a 5- to 7-membered ring together with the nitrogen atom to which R a is bonded and the carbon atom to which R 3 is bonded,
R b represents —C (O) R 7b or —C (S) R 7b ;
R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S (O) r2 R 11a ,
R 6a and R 7a each independently represent C 1 -C 6 alkyl;
R 8a and R 9a each independently represents a hydrogen atom or C 1 -C 6 alkyl;
R 11a represents C 1 -C 6 alkyl, —C (O) OR 16a or —C (O) R 17a .
R 11b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted with R 15b ,
R 12b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl or (C 2 -C 6 ) alkynyl optionally substituted with R 15c ,
R 13b and R 14b are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 Cycloalkyl, —S (O) r3 R 16b , —C (O) OR 16b , —C (O) SR 16b , —C (O) R 17b , —C (O) N (R 18b ) R 19b , — C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38 Alternatively, R 13b may form a C 4 to C 6 alkylene chain together with R 14b to form a 5- to 7-membered ring together with the nitrogen atom to which R 13b and R 14b are bonded.
　Ｒ１５ｂは、ハロゲン原子又はシアノを表し、
　Ｒ１５ｃは、-ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
　Ｒ１６ａ及びＲ１７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表し
　Ｒ１７ｂ及びＲ１８ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
　Ｒ１９ｂは、水素原子又はＣ１～Ｃ６アルキルを表す。
　Ｒ２０は、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ又はフェニルを表し、
　Ｘ１は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ２８は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
　Ｚは、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルコキシ又はＣ１～Ｃ６ハロアルキルチオを表す上記〔６〕に記載のチアゾール誘導体又はその塩。 R 15b represents a halogen atom or cyano,
R 15c represents —OH, —OR 16c , —SH, —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98;
R 16a and R 17a each independently represent C 1 -C 6 alkyl;
R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 16c is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, Phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38, each of R 17b and R 18b independently represents a hydrogen atom , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, phenyl or ( Z) represents phenyl substituted by q ;
R 19b represents a hydrogen atom or C 1 -C 6 alkyl.
R 20 represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or phenyl,
X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
Z represents a halogen atom, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio, the thiazole derivative according to the above [6] Or a salt thereof.
　　〔８〕
　Ｒ１は、水素原子を表し、
　Ｒ３は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル又は－Ｃ（Ｏ）ＯＲ６ａを表すか、或いは、ＲａはＲ３と一緒になってＣ３のアルキレン鎖を形成することにより、Ｒａが結合する窒素原子及びＲ３が結合する炭素原子と共に６員環を形成してもよく、
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂを表し、
　Ｒ５ａは、Ｃ３～Ｃ８シクロアルキル又は－ＯＲ１１ａを表し、
　Ｒ６ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ１７ａを表し、
　Ｒ１１ｂは、Ｃ１～Ｃ６アルキル又はＲ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表し、
　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
　Ｒ１４ｂは、水素原子を表し、
　Ｒ１５ｂは、ハロゲン原子を表す。 [8]
R 1 represents a hydrogen atom,
R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl, R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 to C 6 alkynyl or —C (O) OR 6a , or R a together with R 3 forms a C 3 alkylene chain to form a nitrogen atom to which R a is attached and R 3 May form a 6-membered ring with the carbon atom to which
R b represents —C (O) R 7b ;
R 5a represents C 3 -C 8 cycloalkyl or —OR 11a ;
R 6a represents C 1 -C 6 alkyl;
R 11a represents C 1 -C 6 alkyl or —C (O) R 17a ,
R 11b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 15b ,
R 12b represents hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R optionally substituted with 15c (C 1 ~ C 6) alkyl or R 15c and (C 2 ~ C 6) alkynyl,
R 13b is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl optionally substituted with R 15b , —C (O) OR 16b , —C (O ) R 17b , —C (O) N (R 18b ) R 19b , —C (S) N (R 18b ) R 19b , phenyl or phenyl substituted by (Z) q ,
R 14b represents a hydrogen atom,
R 15b represents a halogen atom.
　Ｒ１５ｃは、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
　Ｒ１７ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１７ｂは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル又はフェニルを表し、
　Ｒ１８ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
　Ｒ１９ｂは、水素原子を表す。
　Ｒ２０は、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
　Ｘ１は、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ２８は、ハロゲン原子を表し、
　Ｚは、ハロゲン原子、ニトロ又は、Ｃ１～Ｃ６アルコキシを表し、
　ｇ１及びｇ４は、１の整数を表し、
　ｆ５、ｆ７、ｍ１、ｍ３及びｎは、０を表し、
　ｑは、１又は２の整数を表し、
　ｒは、０、１又は２の整数を表す上記〔７〕に記載のチアゾール誘導体又はその塩。
　　〔９〕
　Ｒ７ｂは、－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表す上記〔２〕に記載のピラゾール誘導体又はその塩。 R 15c represents —OR 16c , —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98;
R 16b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 16c is, C 1 ~ C 6 alkyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, C 3 ~ C 8 cycloalkyl, substituted by (Z) q Represents phenyl or D1-32.
R 17a represents C 1 -C 6 alkyl;
R 17b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 3 -C 8 cycloalkyl or phenyl;
R 18b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, phenyl or phenyl substituted by (Z) q ;
R 19b represents a hydrogen atom.
R 20 represents a halogen atom, cyano, C 1 -C 6 alkoxy or phenyl,
X 1 represents (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
R 28 represents a halogen atom,
Z represents a halogen atom, nitro or C 1 -C 6 alkoxy;
g1 and g4 represent an integer of 1;
f5, f7, m1, m3 and n represent 0;
q represents an integer of 1 or 2,
r is a thiazole derivative or a salt thereof according to the above [7], wherein r represents an integer of 0, 1 or 2.
[9]
R 7b is a pyrazole derivative or a salt thereof according to the above [2], wherein R 7b represents —C {= NN (R 13b ) R 14b } R 12b .
　　〔１０〕
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ６ａ又は－Ｃ（Ｏ）Ｒ７ａを表し、
　Ｒｂは、、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表し、
　Ｒ５ａは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
　Ｒ６ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ７ａは、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、－Ｃ（Ｏ）ＯＲ１６ａ又は－Ｃ（Ｏ）Ｒ１７ａを表し、
　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表す。
　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４～Ｃ６のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５～７員環を形成してもよい。 [10]
R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) Represents OR 6a or —C (O) R 7a ,
R b represents —C (O) R 7b or —C (S) R 7b ;
R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S (O) r2 R 11a ,
R 6a represents C 1 -C 6 alkyl;
R 7a represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl,
R 11a represents C 1 -C 6 alkyl, —C (O) OR 16a or —C (O) R 17a ,
R 12b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl or (C 2 -C 6 ) alkynyl optionally substituted with R 15c .
R 13b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15b (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15b (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r3 R 16b , —C ( O) OR 16b , —C (S) OR 16b , —C (O) SR 16b , —C (S) SR 16b , —C (O) R 17b , —C (S) R 17b , —C (O) N (R 18b ) R 19b , —C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1 represent a -37 or D1-38, or, R 1 b is by forming an alkylene chain of C 4 ~ C 6 taken together with R 14b, may form a 5- to 7-membered ring together with the nitrogen atom to which R 13b and R 14b are bonded.
　Ｒ１４ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル又はＣ２～Ｃ６アルケニルを表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよく、
　Ｒ１４ｅ及びＲ１４ｆは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、－ＯＲ１６ｂ又は－Ｓ（Ｏ）ｒ３Ｒ１６ｂを表し、
　Ｒ１５ｂは、ハロゲン原子又はシアノを表し、
　Ｒ１５ｃは、-ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、Ｄ１－８７又はＤ１－９８を表し、
　Ｒ１６ａ及びＲ１７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、フェニル又は（Ｚ）ｑによって置換されたフェニル表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表す。 R 14b represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl or C 2 -C 6 alkenyl optionally substituted with R 15b , or R 14b together with R 13b = C (R 14e ) R 14f may be formed,
R 14e and R 14f each independently represent a hydrogen atom, C 1 -C 6 alkyl, —OR 16b or —S (O) r3 R 16b ,
R 15b represents a halogen atom or cyano,
R 15c represents -OH, -OR 16c , -SH, -S (O) r R 16c , D1-87 or D1-98,
R 16a and R 17a each independently represent C 1 -C 6 alkyl;
R 16b is, C 1 ~ C 6 -alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) Represents phenyl substituted by alkenyl, phenyl or (Z) q ;
R 16c is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, Phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38.
　Ｒ１７ｂ、Ｒ１８ｂ及びＲ１９ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表し、
　Ｒ２０は、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＲ２１、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
　Ｘ１は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ２８は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
　Ｚは、ハロゲン原子、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ又はＣ１～Ｃ６ハロアルキルチオを表す上記〔９〕に記載のピラゾール誘導体又はその塩。 R 17b , R 18b and R 19b are each independently a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -C (O) R 22, - C (= NOR 21 ) R 22 , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38,
R 20 represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1- C 6 alkylsulfonyl, —C (O) OR 21 , phenyl or phenyl substituted by (Z) q .
X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
Z is a halogen atom, nitro, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C The pyrazole derivative or the salt thereof according to the above [9], which represents 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio or C 1 to C 6 haloalkylthio.
　　〔１１〕
　Ｒ１は、水素原子を表し、
　Ｒ２は、ハロゲン原子を表し、
　Ｒ４は、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ３は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル又は－Ｃ（Ｏ）Ｒ７ａを表し、
　Ｒ５ａは、－ＯＲ１１ａを表し、
　Ｒ７ａは、Ｃ３～Ｃ８シクロアルキルを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル又はＲ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表す。
　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２又はＤ１－３７を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５員環を形成してもよく、
　Ｒ１４ｂは、水素原子又はＣ１～Ｃ６アルキルを表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよい。 [11]
R 1 represents a hydrogen atom,
R 2 represents a halogen atom,
R 4 represents a hydrogen atom or C 1 -C 6 alkyl,
R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a or —C (O) R 7a ,
R 5a represents -OR 11a ;
R 7a represents C 3 -C 8 cycloalkyl,
R 11a represents C 1 -C 6 alkyl,
R 12b represents a hydrogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 15c .
R 13b is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, —S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (O) R 17b, -C (O) N (R 18b) R 19b, -C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32 or D1-37, or R 13b together with R 14b forms a C 4 alkylene chain , R 13b and R 14b may form a 5-membered ring with the nitrogen atom to which they are bonded,
R 14b represents a hydrogen atom or C 1 -C 6 alkyl, or R 14b together with R 13b may form ═C (R 14e ) R 14f .
　Ｒ１４ｅは、Ｃ１～Ｃ６アルキル又は－ＯＲ１６ｂを表し、
　Ｒ１４ｆは、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ１５ｂは、ハロゲン原子を表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル又はフェニルを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１７ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
　Ｒ１８ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
　Ｒ１９ｂは、水素原子を表し、
　Ｒ２０は、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、-Ｃ（Ｏ）ＯＲ２１又はフェニルを表し、
　Ｒ２１は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ２２は、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ２８は、ハロゲン原子を表し、
　Ｚは、ハロゲン原子、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６ハロアルコキシ又はＣ１～Ｃ６ハロアルキルチオを表し、
　ｇ１、ｇ４及びｍ３は、０を表し、
　ｎは、０又は１の整数を表し、
　ｑは、１又は２の整数を表し、
　ｒは、０、１又は２の整数を表し、
　ｒ３は、２の整数を表す上記〔１０〕に記載のピラゾール誘導体又はその塩。 R 14e represents C 1 -C 6 alkyl or —OR 16b ,
R 14f represents a hydrogen atom or C 1 -C 6 alkyl,
R 15b represents a halogen atom,
R 15c represents -S (O) r R 16c ;
R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, (C 1 -C 6 ) alkyl or phenyl optionally substituted with R 20 ,
R 16c represents C 1 -C 6 alkyl;
R 17b is optionally substituted with a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 20 (C 1 -C 6 ) alkyl, —C (O) R 22 , —C (═NOR 21 ) R 22 , phenyl, phenyl substituted by (Z) q or D1-32,
R 18b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by (Z) q .
R 19b represents a hydrogen atom,
R 20 represents cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, -C (O) OR 21 or phenyl,
R 21 represents C 1 -C 6 alkyl;
R 22 represents a hydrogen atom or C 1 -C 6 alkyl,
R 28 represents a halogen atom,
Z represents a halogen atom, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio;
g1, g4 and m3 represent 0;
n represents an integer of 0 or 1,
q represents an integer of 1 or 2,
r represents an integer of 0, 1 or 2;
r3 is the pyrazole derivative or the salt thereof according to [10], wherein R3 represents an integer of 2.
　　〔１２〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１及びＲ４は、水素原子を表し、
　ｎ及びｍ１は、０を表す上記〔１〕～〔１１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１３〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１は、ハロゲン原子を表し、
　ｎ及びｍ１は、０を表す上記〔１〕～〔１１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１４〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１は、水素原子を表し、
　Ｒ２は、ハロゲン原子を表し、
　ｎは、１の整数を表し、
　ｍ１は、０を表す上記〔１〕～〔１１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１５〕
　Ａ１は、－ＣＲ１を表し、
　Ｒ１は、水素原子を表し、
　ｎは、０を表し、
　ｍ１は、１の整数を表す上記〔１〕～〔１１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１６〕
　Ｒ３は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１７〕
　Ｒ３は、水素原子を表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１８〕
　Ｒ３は、ハロゲン原子又はＣ１～Ｃ６アルキルを表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔１９〕
　Ｒ３は、ハロゲン原子を表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２０〕
　Ｒ３は、塩素原子を表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２１〕
　Ｒ３は、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２２〕
　Ｒ３は、メチルを表す上記〔１〕～〔１５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [12]
A 1 represents -CR 1
R 1 and R 4 represent a hydrogen atom,
The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein n and m1 represent 0.
[13]
A 1 represents -CR 1
R 1 represents a halogen atom,
The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein n and m1 represent 0.
[14]
A 1 represents -CR 1
R 1 represents a hydrogen atom,
R 2 represents a halogen atom,
n represents an integer of 1;
The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [11], wherein m1 represents 0.
[15]
A 1 represents -CR 1
R 1 represents a hydrogen atom,
n represents 0;
m1 is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [11], wherein m1 represents an integer of 1.
[16]
R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl.
[17]
R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], in which R 3 represents a hydrogen atom.
[18]
R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents a halogen atom or C 1 -C 6 alkyl.
[19]
R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], which represents a halogen atom.
[20]
R 3 is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], in which R 3 represents a chlorine atom.
[21]
R 3 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [15], wherein R 3 represents C 1 -C 6 alkyl.
[22]
The pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [15], wherein R 3 represents methyl.
　　〔２３〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ又は－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａを表し、
　Ｒ５ａは、－ＯＲ１１ａ又は－Ｃ（Ｏ）ＯＨを表し、
　Ｒ８ａは、水素原子を表し、
　Ｒ９ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１１ａは、－Ｃ（Ｏ）ＯＲ１６ａ、－Ｃ（Ｏ）Ｒ１７ａ又は－Ｃ（Ｏ）Ｎ（Ｒ１８ａ）Ｒ１９ａを表し、
　Ｒ１６ａは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１７ａは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
　Ｒ１８ａ及びＲ１９ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ２０は、Ｃ１～Ｃ６アルコキシを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２４〕
　Ｒａは、水素原子を表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [23]
R a represents (C 1 -C 6 ) alkyl, —C (O) N (R 8a ) R 9a or —C (S) N (R 8a ) R 9a optionally substituted with R 5a ,
R 5a represents —OR 11a or —C (O) OH;
R 8a represents a hydrogen atom,
R 9a represents C 1 -C 6 alkyl;
R 11a represents —C (O) OR 16a , —C (O) R 17a or —C (O) N (R 18a ) R 19a ,
R 16a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 17a represents C 1 -C 6 alkyl or phenyl;
R 18a and R 19a each independently represent C 1 -C 6 alkyl;
R 20 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 20 represents C 1 -C 6 alkoxy.
[24]
R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which R a represents a hydrogen atom.
　　〔２５〕
　Ｒａは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２６〕
　Ｒａは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２７〕
　Ｒａは、Ｃ２～Ｃ６アルケニルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２８〕
　Ｒａは、Ｃ２～Ｃ６アルキニルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔２９〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＨ又は－ＯＲ１１ａを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキル又はＣ２～Ｃ６アルキニルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３０〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、シアノを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [25]
R a represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [22] above.
[26]
R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 1 -C 6 alkyl.
[27]
R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 2 -C 6 alkenyl.
[28]
R a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R a represents C 2 -C 6 alkynyl.
[29]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a represents cyano, C 3 -C 8 cycloalkyl, —OH or —OR 11a ,
R 11a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 11a represents C 1 -C 6 alkyl or C 2 -C 6 alkynyl.
[30]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which R 5a represents cyano.
　　〔３１〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、Ｃ３～Ｃ８シクロアルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３２〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、－ＯＲ１１ａを表し、
　Ｒ１１ａは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３３〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、－ＯＨを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３４〕
　Ｒａは、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ５ａは、－ＯＲ１１ａを表し、
　Ｒ１１ａは、Ｃ２～Ｃ６アルキニルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３５〕
　Ｒａは、－Ｃ（Ｏ）Ｒ７ａを表し、
　Ｒ７ａは、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表す上記〔１〕～〔２２〕記載のピラゾール若しくはチアゾール誘導体又はその塩。 [31]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a is, pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [22] representing the C 3 - C 8 cycloalkyl.
[32]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a represents -OR 11a ;
R 11a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which R 11a represents C 1 -C 6 alkyl.
[33]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], in which —OH represents —OH.
[34]
R a represents (C 1 -C 6 ) alkyl optionally substituted with R 5a ,
R 5a represents -OR 11a ;
R 11a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 11a represents C 2 -C 6 alkynyl.
[35]
R a represents —C (O) R 7a ;
R 7a is a pyrazole or thiazole derivative or a salt thereof according to the above [1] to [22], wherein R 7a represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl.
　　〔３６〕
　Ｒａは、－Ｃ（Ｏ）Ｒ７ａを表し、
　Ｒ７ａは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３７〕
　Ｒａは、－Ｃ（Ｏ）Ｒ７ａを表し、
　Ｒ７ａは、Ｃ３～Ｃ８シクロアルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３８〕
　Ｒａは、－Ｃ（Ｏ）ＯＲ６ａを表し、
　Ｒ６ａは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔２２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔３９〕
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表す上記〔１〕～〔３８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４０〕
　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂを表す上記〔１〕～〔３８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [36]
R a represents —C (O) R 7a ;
R 7a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 7a represents C 1 -C 6 alkyl.
[37]
R a represents —C (O) R 7a ;
R 7a is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 7a represents C 3 -C 8 cycloalkyl.
[38]
R a represents —C (O) OR 6a ,
R 6a represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [22], wherein R 6a represents C 1 -C 6 alkyl.
[39]
R b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (O) R 7b or —C (S) R 7b .
[40]
R b represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (O) R 7b .
　　〔４１〕
　Ｒｂは、－Ｃ（Ｓ）Ｒ７ｂを表す上記〔１〕～〔３８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４２〕
　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ又は－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表す上記〔１〕～〔４１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４３〕
　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂを表す上記〔１〕～〔４１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４４〕
　Ｒ７ｂは、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表す上記〔１〕～〔４１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４５〕
　Ｒ７ｂは、－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表す上記〔１〕～〔４１〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４６〕
　Ｒ１１ｂは、Ｃ１～Ｃ１０アルキル又はＣ２～Ｃ６アルケニルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [41]
R b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [38], wherein R b represents —C (S) R 7b .
[42]
R 7b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C (═NOH) R 12b or —C (= NOR 11b ) R 12b .
[43]
R 7b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C (═NOH) R 12b .
[44]
R 7b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C (═NOR 11b ) R 12b .
[45]
R 7b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [41], wherein R 7b represents —C {= NN (R 13b ) R 14b } R 12b .
[46]
R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 1 -C 10 alkyl or C 2 -C 6 alkenyl.
　　〔４７〕
　Ｒ１１ｂは、Ｃ１～Ｃ１０アルキルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４８〕
　Ｒ１１ｂは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔４９〕
　Ｒ１１ｂは、メチルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はそれらの塩。
　　〔５０〕
　Ｒ１１ｂは、エチルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５１〕
　Ｒ１１ｂは、Ｃ２～Ｃ６アルケニルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５２〕
　Ｒ１１ｂは、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｂは、シアノ又はＣ３～Ｃ８シクロアルキルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [47]
R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 1 -C 10 alkyl.
[48]
R 11b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [45] representing the C 1 ~ C 6 alkyl.
[49]
R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 11b represents methyl.
[50]
R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 11b represents ethyl.
[51]
R 11b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 11b represents C 2 -C 6 alkenyl.
[52]
R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b ,
R 15b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], wherein R 15b represents cyano or C 3 -C 8 cycloalkyl.
　　〔５３〕
　Ｒ１１ｂは、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｂは、シアノを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５４〕
　Ｒ１１ｂは、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｂは、Ｃ３～Ｃ８シクロアルキルを表す上記〔１〕～〔４５〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５５〕
　Ｒ１２ｂは、シアノ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ又は－Ｃ｛＝ＮＮ（Ｒ１８ｃ）Ｒ１９ｃ｝Ｒ１７ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１７ｃは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１８ｃは、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ２２を表し、
　Ｒ１９ｃは、水素原子を表し、
　Ｒ２２は、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５６〕
　Ｒ１２ｂは、水素原子又はＣ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔５７〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [53]
R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b ,
R 15b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [45], in which R 15b represents cyano.
[54]
R 11b represents (C 1 -C 6 ) alkyl optionally substituted with R 15b ,
R 15b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [45] representing the C 3 - C 8 cycloalkyl.
[55]
R 12b represents cyano, —C (O) OR 16c , —C (O) N (R 18c ) R 19c or —C {═NN (R 18c ) R 19c } R 17c ,
R 16c represents C 1 -C 6 alkyl;
R 17c represents C 1 -C 6 alkyl;
R 18c represents C 1 -C 6 alkyl or —C (O) R 22 ,
R 19c represents a hydrogen atom,
R 22 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein C 22 represents C 1 -C 6 alkyl.
[56]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 12b represents a hydrogen atom or C 1 -C 6 alkyl.
[57]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
　　〔５８〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000013
 　　〔５９〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000014
 　　〔６０〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000015
 [58]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000013
 [59]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000014
 [60]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000015
　　〔６１〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000016
 　　〔６２〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000017
 　　〔６３〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000018
 [61]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000016
 [62]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000017
 [63]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000018
　　〔６４〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000019
 　　〔６５〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000020
 　　〔６６〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000021
 　　〔６７〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000022
 [64]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000019
 [65]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000020
 [66]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000021
 [67]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000022
　　〔６８〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000023
 　　〔６９〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000024
 　　〔７０〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000025
 [68]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000023
 [69]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000024
 [70]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000025
　　〔７１〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000026
 　　〔７２〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000027
 　　〔７３〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000028
 [71]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000026
 [72]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000027
 [73]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000028
　　〔７４〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000029
 　　〔７５〕
　Ｒ１２ｂは、以下の構造式で表される置換基を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
Figure JPOXMLDOC01-appb-C000030
 　　〔７６〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ３～Ｃ８シクロアルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [74]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000029
 [75]
R 12b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], which represents a substituent represented by the following structural formula.
Figure JPOXMLDOC01-appb-C000030
 [76]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is the pyrazole or thiazole derivative or salt thereof according to any one of the above [1] to [54], wherein C 16 represents C 3 -C 8 cycloalkyl.
　　〔７７〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル又はＲ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔７８〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔７９〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [77]
R 12b is optionally substituted with R 15c (C 2 ~ C 6 ) alkenyl, optionally substituted with optionally substituted with R 15c (C 2 ~ C 6 ) alkynyl, or R 15c (C 3 ~ C 8 ) represents cycloalkyl,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[78]
R 12b represents (C 2 -C 6 ) alkenyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[79]
R 12b represents (C 2 -C 6 ) alkynyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
　　〔８０〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８１〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ２～Ｃ６アルケニルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８２〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ２０ｃは、ハロゲン原子を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８３〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、Ｄ１－８７又はＤ１－９８を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [80]
R 12b represents (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[81]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein C 16 represents C 2 -C 6 alkenyl.
[82]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents -S (O) r R 16c ;
R 16c represents (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
R 20c is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], in which R 20c represents a halogen atom.
[83]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c is the pyrazole or thiazole derivative or salt thereof according to any one of the above [1] to [54], wherein D 15 represents D 1-87 or D 1-98.
　　〔８４〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、ハロゲン原子又は－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８５〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、シアノ又は－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８６〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－ＯＲ１６ｃ又は－Ｓ（Ｏ）ｒＲ１６ｃを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８７〕
　Ｒ１２ｂは、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
　Ｒ１５ｃは、－ＯＲ１６ｃ又は－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル又は－Ｓ（Ｏ）ｒＲ２１を表し、
Ｒ２１は、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔８８〕
　Ｒ１２ｂは、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－２、Ｄ１－３２又はＤ１－３４を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [84]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents a halogen atom or —S (O) r R 16c ,
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[85]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents cyano or —S (O) r R 16c ,
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[86]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 15c represents —OR 16c or —S (O) r R 16c .
[87]
R 12b represents (C 1 -C 6 ) alkyl optionally substituted with R 15c ,
R 15c represents -OR 16c or -S (O) r R 16c ;
R 16c represents C 1 -C 6 alkyl or —S (O) r R 21 ,
R 21 represents a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 21 represents C 1 -C 6 alkyl.
[88]
R 12b is phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34, and the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [54] above .
　　〔８９〕
　Ｒ１２ｂは、－Ｓ（Ｏ）ｒＲ１６ｃを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９０〕
　Ｒ１２ｂは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９１〕
　Ｒ１２ｂは、－Ｃ（Ｏ）Ｒ１７ｃを表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９２〕
　Ｒ１２ｂは、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－２、Ｄ１－３２又はＤ１－３４を表す上記〔１〕～〔５４〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９３〕
　Ｒ１３ｂは、水素原子を表す上記〔１〕～〔９２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [89]
R 12b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein -S (O) r R 16c is represented.
[90]
R 12b represents -S (O) r R 16c ;
R 16c is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein R 16c represents C 1 -C 6 alkyl.
[91]
R 12b is the pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [54], wherein -C (O) R 17c is represented.
[92]
R 12b is phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34, and the pyrazole or thiazole derivative or salt thereof according to any one of [1] to [54] above .
[93]
R 13b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [92], in which R 13b represents a hydrogen atom.
　　〔９４〕
　Ｒ１３ｂは、－Ｓ（Ｏ）ｒ３Ｒ１６ｂを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔９２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９５〕
　Ｒ１３ｂは、－Ｃ（Ｏ）ＯＲ１６ｂを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔９２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９６〕
　Ｒ１３ｂは、－Ｃ（Ｏ）Ｒ１７ｂを表し、
　Ｒ１６ｂは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔９２〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９７〕
　Ｒ１４ｂは、水素原子を表す上記〔１〕～〔９６〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。
　　〔９８〕
　Ｒ１４ｂは、Ｃ１～Ｃ６アルキルを表す上記〔１〕～〔９６〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩。 [94]
R 13b represents -S (O) r3 R 16b ,
R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ~ C 6 alkyl.
[95]
R 13b represents -C (O) OR 16b ,
R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ~ C 6 alkyl.
[96]
R 13b represents -C (O) R 17b ,
R 16b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [92], which represents the C 1 ~ C 6 alkyl.
[97]
R 14b is a pyrazole or thiazole derivative or a salt thereof according to any one of the above [1] to [96], in which R 14b represents a hydrogen atom.
[98]
R 14b is pyrazole or thiazole derivative or a salt thereof according to any one of [1] to [96], which represents the C 1 ~ C 6 alkyl.
　　〔９９〕
　上記〔１〕～〔９８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する有害生物防除剤。
　　〔１００〕
　上記〔１〕～〔９８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する農薬。
　　〔１０１〕
　上記〔１〕～〔９８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する、哺乳動物又は鳥類の内部若しくは外部寄生虫防除剤。
　　〔１０２〕
　上記〔１〕～〔９８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する殺虫剤又は殺ダニ剤。
　　〔１０３〕
　上記〔１〕～〔９８〕のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する土壌処理剤。
　　〔１０４〕
　土壌処理方法が土壌潅注処理である上記〔１０３〕に記載の土壌処理剤。 [99]
A pest control agent comprising one or more selected from the pyrazole or thiazole derivatives or salts thereof according to any one of [1] to [98] as an active ingredient.
[100]
An agrochemical containing one or more selected from the pyrazole or thiazole derivatives according to any one of [1] to [98] above or a salt thereof as an active ingredient.
[101]
A mammal or avian internal or ectoparasite control agent comprising, as an active ingredient, one or more selected from the pyrazole or thiazole derivative according to any one of [1] to [98] or a salt thereof.
[102]
An insecticide or acaricide containing, as an active ingredient, one or more selected from the pyrazole or thiazole derivatives or salts thereof according to any one of [1] to [98] above.
[103]
A soil treatment agent containing one or more selected from the pyrazole or thiazole derivatives according to any one of [1] to [98] above or a salt thereof as an active ingredient.
[104]
The soil treatment agent according to [103], wherein the soil treatment method is soil irrigation treatment.
　本発明化合物は多くの農業害虫、ハダニ類、哺乳動物又は鳥類の、内部若しくは外部寄生虫に対して優れた殺虫・殺ダニ活性を有し、既存の殺虫剤に対して抵抗性を獲得した害虫に対しても十分な防除効果を発揮する。さらに、ホ乳類、魚類及び益虫に対してほとんど悪影響を及ぼさず、低残留性で環境に対する負荷も軽い。
　従って、本発明は有用な新規有害生物防除剤を提供することができる。 The compound of the present invention has excellent insecticidal / miticidal activity against internal or ectoparasites of many agricultural pests, spider mites, mammals or birds, and has acquired resistance to existing insecticides. Exhibits a sufficient control effect. Furthermore, it has little adverse effect on mammals, fish and beneficial insects, has low persistence, and has a light environmental impact.
Therefore, the present invention can provide a useful novel pest control agent.
　本発明に包含される化合物には、置換基の種類によってはＥ－体及びＺ－体の幾何異性体が存在する場合があるが、本発明はこれらＥ－体、Ｚ－体、又はＥ－体及びＺ－体を任意の割合で含む混合物を包含するものである。また、本発明に包含される化合物は、１個又は２個以上の不斉炭素原子の存在に起因する光学活性体が存在するが、本発明は全ての光学活性体又はラセミ体を包含する。 The compounds encompassed by the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, but the present invention is not limited to these E-form, Z-form, or E-form. And a mixture containing Z-isomer and Z-isomer in an arbitrary ratio. In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
　本発明に包含される化合物のうちで、常法に従って酸付加塩にすることができるものは、例えば、フッ化水素酸、塩酸、臭化水素酸、ヨウ化水素酸等のハロゲン化水素酸の塩、硝酸、硫酸、燐酸、塩素酸、過塩素酸等の無機酸の塩、メタンスルホン酸、エタンスルホン酸、トリフルオロメタンスルホン酸、ベンゼンスルホン酸、ｐ－トルエンスルホン酸等のスルホン酸の塩、ギ酸、酢酸、プロピオン酸、トリフルオロ酢酸、フマール酸、酒石酸、蓚酸、マレイン酸、リンゴ酸、コハク酸、安息香酸、マンデル酸、アスコルビン酸、乳酸、グルコン酸、クエン酸等のカルボン酸の塩又はグルタミン酸、アスパラギン酸等のアミノ酸の塩とすることができる。
　或いは、本発明に包含される化合物のうちで、常法に従って金属塩にすることができるものは、例えば、リチウム、ナトリウム、カリウムといったアルカリ金属の塩、カルシウム、バリウム、マグネシウムといったアルカリ土類金属の塩、又はアルミニウムの塩とすることができる。 Among the compounds included in the present invention, those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like. Salts, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, sulfonic acid salts such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, etc. A salt of an amino acid such as glutamic acid or aspartic acid can be used.
Alternatively, among the compounds included in the present invention, those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or an aluminum salt.
　次に、本明細書において示した各置換基の具体例を以下に示す。ここで、ｎ－はノルマル、ｉ－はイソ、ｓ－はセカンダリー及びｔｅｒｔ－はターシャリーを各々意味し、Ｐｈはフェニルを意味する。
　本明細書におけるハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。尚、本明細書中「ハロ」の表記もこれらのハロゲン原子を表す。 Next, specific examples of each substituent shown in the present specification are shown below. Here, n- means normal, i- means iso, s- means secondary and tert- means tertiary, and Ph means phenyl.
Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.
　本明細書におけるＣａ～Ｃｂアルキルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、例えばメチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｉ－ブチル基、ｓ－ブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、１，１－ジメチルプロピル基、ｎ－ヘキシル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えばフルオロメチル基、クロロメチル基、ブロモメチル基、ヨードメチル基、ジフルオロメチル基、ジクロロメチル基、トリフルオロメチル基、クロロジフルオロメチル基、トリクロロメチル基、ブロモジフルオロメチル基、２－フルオロエチル基、２－クロロエチル基、２－ブロモエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、２－クロロ－２，２－ジフルオロエチル基、２，２，２－トリクロロエチル基、１，１，２，２－テトラフルオロエチル基、２－クロロ－１，１，２－トリフルオロエチル基、ペンタフルオロエチル基、３，３，３－トリフルオロプロピル基、２，２，３，３，３－ペンタフルオロプロピル基、１，１，２，３，３，３－ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチル基、２，２，３，３，４，４，４－ヘプタフルオロブチル基、ノナフルオロブチル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, for example, a methyl group, an ethyl group, an n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group and the like. Each selected range of carbon atoms is selected.
In the present specification, C a -C b haloalkyl is a linear or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. Represents a hydrocarbon group, and when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂシクロアルキルの表記は、炭素原子数がａ～ｂ個よりなる環状の炭化水素基を表し、３員環から８員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよい。例えばシクロプロピル基、１－メチルシクロプロピル基、２－メチルシクロプロピル基、２，２－ジメチルシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロシクロアルキルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる環状の炭化水素基を表し、３員環から８員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよく、ハロゲン原子による置換は環構造部分であっても、側鎖部分であっても、或いはそれらの両方であってもよく、さらに、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えば２，２－ジフルオロシクロプロピル基、２，２－ジクロロシクロプロピル基、２，２－ジブロモシクロプロピル基、２，２－ジフルオロ－１－メチルシクロプロピル基、２，２－ジクロロ－１－メチルシクロプロピル基、２，２－ジブロモ－１－メチルシクロプロピル基、２，２，３，３－テトラフルオロシクロブチル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 8 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc. Selected in a range of numbers.
In the present specification, C a -C b halocycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And can form monocyclic or complex ring structures from 3 to 8 membered rings. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Specific examples include cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, etc., each selected within the range of the designated number of carbon atoms. The
　本明細書におけるＣａ～Ｃｂアルケニルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の二重結合を有する不飽和炭化水素基を表し、例えばビニル基、１－プロペニル基、２－プロペニル基、１－メチルエテニル基、２－ブテニル基、２－メチル－２－プロペニル基、３－メチル－２－ブテニル基、１，１－ジメチル－２－プロペニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルケニルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の二重結合を有する不飽和炭化水素基を表す。このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えば２，２－ジクロロビニル基、２－フルオロ－２－プロペニル基、２－クロロ－２－プロペニル基、３－クロロ－２－プロペニル基、２－ブロモ－２－プロペニル基、３，３－ジフルオロ－２－プロペニル基、２，３－ジクロロ－２－プロペニル基、３，３－ジクロロ－２－プロペニル基、２，３，３－トリフルオロ－２－プロペニル基、２，３，３－トリクロロ－２－プロペニル基、１－（トリフルオロメチル）エテニル基、４，４－ジフルオロ－３－ブテニル基、３，４，４－トリフルオロ－３－ブテニル基、３－クロロ－４，４，４－トリフルオロ－２－ブテニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 Specific examples include 1,2-dimethyl-2-propenyl group and the like, and each is selected within the range of the designated number of carbon atoms.
In the present specification, C a -C b haloalkenyl is represented by a linear or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2,2-dichlorovinyl group, 2-fluoro-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2-bromo-2-propenyl group, 3,3-difluoro -2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-dichloro-2-propenyl group, 2,3,3-trifluoro-2-propenyl group, 2,3,3-trichloro- 2-propenyl group, 1- (trifluoromethyl) ethenyl group, 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, 3-chloro-4,4,4- Specific examples include a trifluoro-2-butenyl group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂシクロアルケニルの表記は、炭素原子数がａ～ｂ個よりなる環状の、且つ１個又は２個以上の二重結合を有する不飽和炭化水素基を表し、３員環から６員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよく、さらに、二重結合はｅｎｄｏ－又はｅｘｏ－のどちらの形式であってもよい。例えば１－シクロペンテン－１－イル基、２－シクロペンテン－１－イル基、１－シクロヘキセン－１－イル基、２－シクロヘキセン－１－イル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂアルキリデンの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、二重結合によって結合した炭化水素基を表し、例えばメチリデン基、エチリデン基、プロピリデン基、１－メチルエチリデン基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms. A monocyclic or complex ring structure from a member ring to a 6-member ring can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form. Specific examples include 1-cyclopenten-1-yl group, 2-cyclopenten-1-yl group, 1-cyclohexen-1-yl group, 2-cyclohexen-1-yl group, and the like. Selected in a range of numbers.
In the present specification, C a -C b alkylidene represents a linear or branched hydrocarbon group having a carbon number of a to b and bonded by a double bond, for example, a methylidene group, an ethylidene group, Specific examples include a group, a propylidene group, a 1-methylethylidene group, etc., and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキニルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の三重結合を有する不飽和炭化水素基を表し、例えばエチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１，１－ジメチル－２－プロピニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキニルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の三重結合を有する不飽和炭化水素基を表す。このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えば２－クロロエチニル基、２－ブロモエチニル基、２－ヨードエチニル基、３－クロロ－２－プロピニル基、３－ブロモ－２－プロピニル基、３－ヨード－２－プロピニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkynyl represents a linear or branched chain having a carbon number of a to b and an unsaturated group having one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1,1-dimethyl-2-propynyl group, etc. Each of which is selected for each specified number of carbon atoms.
In the present specification, C a -C b haloalkynyl represents a linear or branched chain having a carbon number of a to b in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. And an unsaturated hydrocarbon group having one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples include 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group and the like. Each of which is selected for each specified number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルコキシの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｏ－基を表し、例えばメトキシ基、エトキシ基、ｎ－プロピルオキシ基、ｉ－プロピルオキシ基、ｎ－ブチルオキシ基、ｉ－ブチルオキシ基、ｓ－ブチルオキシ基、ｔｅｒｔ－ブチルオキシ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルコキシの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｏ－基を表し、例えばジフルオロメトキシ基、トリフルオロメトキシ基、クロロジフルオロメトキシ基、ブロモジフルオロメトキシ基、２－フルオロエトキシ基、２－クロロエトキシ基、２，２，２－トリフルオロエトキシ基、１，１，２，２，－テトラフルオロエトキシ基、２－クロロ－１，１，２－トリフルオロエトキシ基、１，１，２，３，３，３－ヘキサフルオロプロピルオキシ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, such as methoxy group, ethoxy group, n-propyloxy group, Specific examples include i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
The notation of C a -C b haloalkoxy in the present specification represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2, -tetrafluoroethoxy group, 2-chloro-1 Specific examples include 1,2,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルチオの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｓ－基を表し、例えばメチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔｅｒｔ－ブチルチオ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルチオの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｓ－基を表し、例えばジフルオロメチルチオ基、トリフルオロメチルチオ基、クロロジフルオロメチルチオ基、ブロモジフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基、１，１，２，２－テトラフルオロエチルチオ基、２－クロロ－１，１，２－トリフルオロエチルチオ基、ペンタフルオロエチルチオ基、１，１，２，３，３，３－ヘキサフルオロプロピルチオ基、ヘプタフルオロプロピルチオ基、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチルチオ基、ノナフルオロブチルチオ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning comprising a to b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, and each is selected within the range of the designated number of carbon atoms.
The notation of C a -C b haloalkylthio in the present specification represents a haloalkyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylthio group, trifluoromethylthio group, chlorodifluoro Methylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-trifluoroethylthio group, Pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio group , Nonafluorobutylthio group and the like are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルスルフィニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｓ（Ｏ）－基を表し、例えばメチルスルフィニル基、エチルスルフィニル基、ｎ－プロピルスルフィニル基、ｉ－プロピルスルフィニル基、ｎ－ブチルスルフィニル基、ｉ－ブチルスルフィニル基、ｓ－ブチルスルフィニル基、ｔｅｒｔ－ブチルスルフィニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルスルフィニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｓ（Ｏ）－基を表し、例えばジフルオロメチルスルフィニル基、トリフルオロメチルスルフィニル基、クロロジフルオロメチルスルフィニル基、ブロモジフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチルスルフィニル基、ノナフルオロブチルスルフィニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, Specific examples include n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. The range is selected.
In the present specification, the expression C a -C b haloalkylsulfinyl represents a haloalkyl-S (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethylsulfinyl group, trifluoromethyl Sulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl group, nona Specific examples include a fluorobutylsulfinyl group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルスルホニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－ＳＯ２－基を表し、例えばメチルスルホニル基、エチルスルホニル基、ｎ－プロピルスルホニル基、ｉ－プロピルスルホニル基、ｎ－ブチルスルホニル基、ｉ－ブチルスルホニル基、ｓ－ブチルスルホニル基、ｔｅｒｔ－ブチルスルホニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルスルホニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－ＳＯ２－基を表し、例えばジフルオロメチルスルホニル基、トリフルオロメチルスルホニル基、クロロジフルオロメチルスルホニル基、ブロモジフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基、１，１，２，２－テトラフルオロエチルスルホニル基、２－クロロ－１，１，２－トリフルオロエチルスルホニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylsulfonyl in the present specification represents an alkyl-SO 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group, n- Specific examples include propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group, etc. Selected.
The notation of C a -C b haloalkylsulfonyl in the present specification represents a haloalkyl-SO 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, such as a difluoromethylsulfonyl group or a trifluoromethylsulfonyl group. Chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1,1,2-trimethyl Specific examples include a fluoroethylsulfonyl group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルアミノの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたアミノ基を表し、例えばメチルアミノ基、エチルアミノ基、ｎ－プロピルアミノ基、ｉ－プロピルアミノ基、ｎ－ブチルアミノ基、ｉ－ブチルアミノ基、ｔｅｒｔ－ブチルアミノ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるジ（Ｃａ～Ｃｂアルキル）アミノの表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたアミノ基を表し、例えばジメチルアミノ基、エチル（メチル）アミノ基、ジエチルアミノ基、ｎ－プロピル（メチル）アミノ基、ｉ－プロピル（メチル）アミノ基、ジ（ｎ－プロピル）アミノ基、ジ（ｎ－ブチル）アミノ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example, a methylamino group , Ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i-butylamino group, tert-butylamino group and the like. Selected by range.
The notation of di (C a -C b alkyl) amino in the present specification has the above-mentioned meaning that the number of carbon atoms, which may be the same or different from each other, is ab. Represents an amino group substituted by an alkyl group, such as dimethylamino group, ethyl (methyl) amino group, diethylamino group, n-propyl (methyl) amino group, i-propyl (methyl) amino group, di (n-propyl) Specific examples include an amino group, a di (n-butyl) amino group, and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルイミノの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｎ＝基を表し、例えばメチルイミノ基、エチルイミノ基、ｎ－プロピルイミノ基、ｉ－プロピルイミノ基、ｎ－ブチルイミノ基、ｉ－ブチルイミノ基、ｓ－ブチルイミノ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂアルコキシイミノの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルコキシ－Ｎ＝基を表し、例えばメトキシイミノ基、エトキシイミノ基、ｎ－プロピルオキシイミノ基、ｉ－プロピルオキシイミノ基、ｎ－ブチルオキシイミノ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylimino in the present specification represents an alkyl-N = group having the above-mentioned meaning consisting of a to b carbon atoms, for example, methylimino group, ethylimino group, n-propylimino group. Specific examples thereof include i-propylimino group, n-butylimino group, i-butylimino group, s-butylimino group and the like, and each is selected within the range of the designated number of carbon atoms.
In the present specification, C a -C b alkoxyimino represents an alkoxy-N = group having the above-mentioned meanings having a carbon number of a to b, for example, methoxyimino group, ethoxyimino group, n-propyl group. Specific examples include an oxyimino group, an i-propyloxyimino group, an n-butyloxyimino group, and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｃ（Ｏ）－基を表し、例えばアセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基、２－メチルブタノイル基、ピバロイル基、ヘキサノイル基、ヘプタノイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｃ（Ｏ）－基を表し、例えばフルオロアセチル基、クロロアセチル基、ジフルオロアセチル基、ジクロロアセチル基、トリフルオロアセチル基、クロロジフルオロアセチル基、ブロモジフルオロアセチル基、トリクロロアセチル基、ペンタフルオロプロピオニル基、ヘプタフルオロブタノイル基、３－クロロ－２，２－ジメチルプロパノイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂシクロアルキルカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルキル－Ｃ（Ｏ）－基を表し、例えばシクロプロピルカルボニル基、２－メチルシクロプロピルカルボニル基、シクロブチルカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロシクロアルキルカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロシクロアルキル－Ｃ（Ｏ）－基を表し、例えば２，２－ジクロロシクロプロピルカルボニル基、２，２－ジクロロ－１－メチルシクロプロピルカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning comprising a to b carbon atoms, for example, an acetyl group, a propionyl group, a butyryl group. Specific examples thereof include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group and the like, and each is selected in the range of the designated number of carbon atoms.
The notation of C a -C b haloalkylcarbonyl in the present specification represents a haloalkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as a fluoroacetyl group, a chloroacetyl group, Difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropanoyl group Etc. are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
The notation of C a -C b cycloalkylcarbonyl in the present specification represents a cycloalkyl-C (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as cyclopropylcarbonyl group, 2 Specific examples include -methylcyclopropylcarbonyl group, cyclobutylcarbonyl group and the like, each selected within the range of the designated number of carbon atoms.
In the present specification, the expression C a -C b halocycloalkylcarbonyl represents a halocycloalkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, for example 2,2- Specific examples include a dichlorocyclopropylcarbonyl group, a 2,2-dichloro-1-methylcyclopropylcarbonyl group, etc., and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルコキシカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｏ－Ｃ（Ｏ）－基を表し、例えばメトキシカルボニル基、エトキシカルボニル基、ｎ－プロピルオキシカルボニル基、ｉ－プロピルオキシカルボニル基、ｎ－ブトキシカルボニル基、ｉ－ブトキシカルボニル基、ｔｅｒｔ－ブトキシカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルコキシカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｏ－Ｃ（Ｏ）－基を表し、例えばクロロメトキシカルボニル基、２－クロロエトキシカルボニル基、２，２－ジフルオロエトキシカルボニル基、２，２，２－トリフルオロエトキシカルボニル基、２，２，２－トリクロロエトキシカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meanings consisting of a to b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Specific examples include a group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like. Selected.
In the present specification, the expression C a -C b haloalkoxycarbonyl represents a haloalkyl-O—C (O) — group having the above-mentioned meaning of a to b carbon atoms, such as a chloromethoxycarbonyl group, Specific examples include 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, and the like. Selected in the range of the number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルアミノカルボニルの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたカルバモイル基を表し、例えばメチルカルバモイル基、エチルカルバモイル基、ｎ－プロピルカルバモイル基、ｉ－プロピルカルバモイル基、ｎ－ブチルカルバモイル基、ｉ－ブチルカルバモイル基、ｓ－ブチルカルバモイル基、ｔｅｒｔ－ブチルカルバモイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂハロアルキルアミノカルボニルの表記は、水素原子の一方が炭素原子数ａ～ｂ個よりなる前記の意味であるハロアルキル基によって置換されたカルバモイル基を表し、例えば２－フルオロエチルカルバモイル基、２－クロロエチルカルバモイル基、２，２－ジフルオロエチルカルバモイル基、２，２，２－トリフルオロエチルカルバモイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるジ（Ｃａ～Ｃｂアルキル）アミノカルボニルの表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたカルバモイル基を表し、例えばＮ，Ｎ－ジメチルカルバモイル基、Ｎ－エチル－Ｎ－メチルカルバモイル基、Ｎ，Ｎ－ジエチルカルバモイル基、Ｎ，Ｎ－ジ（ｎ－プロピル）カルバモイル基、Ｎ，Ｎ－ジ（ｎ－ブチル）カルバモイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example methylcarbamoyl Specific examples include a group, ethylcarbamoyl group, n-propylcarbamoyl group, i-propylcarbamoyl group, n-butylcarbamoyl group, i-butylcarbamoyl group, s-butylcarbamoyl group, tert-butylcarbamoyl group, etc. Is selected within the range of the specified number of carbon atoms.
The notation of C a -C b haloalkylaminocarbonyl in this specification represents a carbamoyl group in which one of the hydrogen atoms is substituted with a haloalkyl group as defined above consisting of a to b carbon atoms, for example 2-fluoro Specific examples include an ethylcarbamoyl group, a 2-chloroethylcarbamoyl group, a 2,2-difluoroethylcarbamoyl group, a 2,2,2-trifluoroethylcarbamoyl group, and the like, each selected within the specified number of carbon atoms. Is done.
In the present specification, the notation of di (C a -C b alkyl) aminocarbonyl means in the above meaning that the number of carbon atoms, which may be the same or different from each other, is ab. Represents a carbamoyl group substituted by an alkyl group, such as N, N-dimethylcarbamoyl group, N-ethyl-N-methylcarbamoyl group, N, N-diethylcarbamoyl group, N, N-di (n-propyl) carbamoyl Specific examples include a group, an N, N-di (n-butyl) carbamoyl group, and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルアミノスルホニルの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたスルファモイル基を表し、例えばメチルスルファモイル基、エチルスルファモイル基、ｎ－プロピルスルファモイル基、ｉ－プロピルスルファモイル基、ｎ－ブチルスルファモイル基、ｉ－ブチルスルファモイル基、ｓ－ブチルスルファモイル基、ｔｅｒｔ－ブチルスルファモイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるジ（Ｃａ～Ｃｂアルキル）アミノスルホニルの表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたスルファモイル基を表し、例えばＮ，Ｎ－ジメチルスルファモイル基、Ｎ－エチル－Ｎ－メチルスルファモイル基、Ｎ，Ｎ－ジエチルスルファモイル基、Ｎ，Ｎ－ジ（ｎ－プロピル）スルファモイル基、Ｎ，Ｎ－ジ（ｎ－ブチル）スルファモイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkylaminosulfonyl represents a sulfamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms. Famoyl group, ethylsulfamoyl group, n-propylsulfamoyl group, i-propylsulfamoyl group, n-butylsulfamoyl group, i-butylsulfamoyl group, s-butylsulfamoyl group, Specific examples include a tert-butylsulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
In the present specification, the notation of di (C a -C b alkyl) aminosulfonyl means in the above meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b. Represents a sulfamoyl group substituted by an alkyl group, such as N, N-dimethylsulfamoyl group, N-ethyl-N-methylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-di- Specific examples include (n-propyl) sulfamoyl group, N, N-di (n-butyl) sulfamoyl group and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＲ５ａで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ１０ａで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ１５ａで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ１５ｂで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ１５ｃで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ１５ｄで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ２８で任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ２８ａで任意に置換された（Ｃａ～Ｃｂ）アルキル、Ｒ３１で任意に置換された（Ｃａ～Ｃｂ）アルキル又はＲ３２で任意に置換された（Ｃａ～Ｃｂ）アルキル等の表記は、任意のＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２によって、炭素原子に結合した水素原子が任意に置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの（Ｃａ～Ｃｂ）アルキル基上の置換基Ｒ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２が２個以上存在するとき、それぞれのＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２は互いに同一でも異なってもよい。 Herein optionally substituted with R 5a (C a ~ C b ) alkyl, optionally substituted with R 10a (C a ~ C b ) alkyl, optionally substituted with R 15a (C a ~ C b) alkyl, optionally substituted with R 15b (C a ~ C b ) alkyl, optionally substituted with R 15c (C a ~ C b ) alkyl, optionally substituted with R 15d (C a ~ C b) alkyl, optionally substituted with R 20 (C a ~ C b ) alkyl, optionally substituted with R 28 (C a ~ C b ) alkyl, optionally substituted with R 28a (C a ~ C b) alkyl, optionally substituted with R 31 (C a ~ C b ) alkyl or optionally substituted with R 32 (C a ~ C b ) notation alkyl or the like, any of R 5a, R 10a, R 15a, R 15b , R 15c, 15d, R 20, R 28, R 28a, by R 31 or R 32, an alkyl group which is defined above the number of carbon atoms bonded hydrogen atom is optionally substituted carbon atoms is formed of a ~ b Pieces , Selected for each specified number of carbon atoms. At this time, the substituents R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 on each (C a -C b ) alkyl group Each of R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
　本明細書におけるＲ５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ１０ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ１５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ１５ｃで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ１５ｄで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ２８で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ２８ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル、Ｒ３１で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル又はＲ３２で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル等の表記は、任意のＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２によって、炭素原子に結合した水素原子が任意に置換された炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの（Ｃａ～Ｃｂ）シクロアルキル基上の置換基Ｒ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２が２個以上存在するとき、それぞれのＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８ａ、Ｒ３１又はＲ３２は互いに同一でも異なってもよく、さらに置換位置は環構造部分であっても、側鎖部分であっても、或いはそれらの両方にあってもよい。 Herein optionally substituted with R 5a (C a ~ C b ) cycloalkyl, optionally substituted with R 10a (C a ~ C b ) cycloalkyl, optionally substituted with R 15a (C a ~ C b) cycloalkyl, optionally substituted with R 15b (C a ~ C b ) cycloalkyl, optionally substituted with R 15c (C a ~ C b ) cycloalkyl, optionally substituted with R 15d been (C a ~ C b) cycloalkyl, optionally substituted with R 20 (C a ~ C b ) cycloalkyl, optionally substituted with R 28 (C a ~ C b ) cycloalkyl, R 28a optionally substituted in (C a ~ C b) cycloalkyl, optionally substituted with optionally substituted with R 31 (C a ~ C b ) cycloalkyl or R 32 (C a ~ C b ) cycloalkyl Notation such as alkyl Is optionally substituted with a hydrogen atom bonded to a carbon atom by any R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 . And the cycloalkyl group having the above-mentioned meaning consisting of a to b carbon atoms, each selected in the range of the designated number of carbon atoms. At this time, the substituents R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R on each (C a -C b ) cycloalkyl group When two or more 32 are present, each R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28a , R 31 or R 32 may be the same or different from each other; The substitution position may be a ring structure moiety, a side chain moiety, or both.
　本明細書におけるＲ５ａで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ１０ａで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ１５ａで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ１５ｂで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ１５ｃで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ１５ｄで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ２８で任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ２８ａで任意に置換された（Ｃａ～Ｃｂ）アルケニル、Ｒ３１で任意に置換された（Ｃａ～Ｃｂ）アルケニル又はＲ３２で任意に置換された（Ｃａ～Ｃｂ）アルケニル等の表記は、任意のＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２によって、炭素原子に結合した水素原子が任意に置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルケニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの（Ｃａ～Ｃｂ）アルケニル基上の置換基Ｒ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２が２個以上存在するとき、それぞれのＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２は互いに同一でも異なってもよい。 Herein optionally substituted with R 5a (C a ~ C b ) alkenyl, optionally substituted with R 10a (C a ~ C b ) alkenyl, optionally substituted with R 15a (C a ~ C b) alkenyl, optionally substituted with R 15b (C a ~ C b ) alkenyl, optionally substituted with R 15c (C a ~ C b ) alkenyl, optionally substituted with R 15d (C a ~ C b) alkenyl, optionally substituted with R 20 (C a ~ C b ) alkenyl, optionally substituted with R 28 (C a ~ C b ) alkenyl, optionally substituted with R 28a (C a ~ C b) alkenyl, which is optionally substituted with R 31 (C a ~ C b ) alkenyl or optionally substituted with R 32 (C a ~ C b ) notation alkenyl or the like, any of R 5a, R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 , wherein the hydrogen atom bonded to the carbon atom is arbitrarily substituted, and the above-mentioned meaning is composed of a to b carbon atoms Are selected within the range of each specified number of carbon atoms. At this time, the substituents R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 on each (C a -C b ) alkenyl group. Each of R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
　Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ１０ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ１５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ１５ｄで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ２８で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ２８ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル、Ｒ３１で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル又はＲ３２で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル等の表記は、任意のＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２によって、炭素原子に結合した水素原子が任意に置換された炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルケニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの（Ｃａ～Ｃｂ）シクロアルケニル基上の置換基Ｒ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２が２個以上存在するとき、それぞれのＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２は互いに同一でも異なってもよく、さらに置換位置は環構造部分であっても、側鎖部分であっても、或いはそれらの両方にあってもよい。 Optionally substituted with R 5a (C a ~ C b ) cycloalkenyl, optionally substituted with R 10a (C a ~ C b ) cycloalkenyl, optionally substituted with R 15a (C a ~ C b ) cycloalkenyl, optionally substituted with R 15b (C a ~ C b ) cycloalkenyl, optionally substituted with R 15c (C a ~ C b ) cycloalkenyl, optionally substituted with R 15d (C a ~ C b) cycloalkenyl, substituted optionally substituted with R 20 (C a ~ C b ) cycloalkenyl, optionally substituted with R 28 (C a ~ C b ) cycloalkenyl, optionally with R 28a been (C a ~ C b) cycloalkenyl, optionally substituted with R 31 (C a ~ C b ) optionally substituted cycloalkenyl, or R 32 (C a ~ C b ) cycloalkenyl, etc. Is represented by any R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 , and a hydrogen atom bonded to a carbon atom is arbitrarily It represents a cycloalkenyl group having the above meaning consisting of a to b substituted carbon atoms, and is selected in the range of each designated number of carbon atoms. At this time, the substituents R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R on each (C a -C b ) cycloalkenyl group When two or more 32 are present, each R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 may be the same or different from each other. Furthermore, the substitution position may be a ring structure part, a side chain part, or both.
　本明細書におけるＲ５ａで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ１０ａで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ１５ａで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ１５ｂで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ１５ｃで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ１５ｄで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ２８で任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ２８ａで任意に置換された（Ｃａ～Ｃｂ）アルキニル、Ｒ３１で任意に置換された（Ｃａ～Ｃｂ）アルキニル又はＲ３２で任意に置換された（Ｃａ～Ｃｂ）アルキニル等の表記は、任意のＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２によって、炭素原子に結合した水素原子が任意に置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルキニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの（Ｃａ～Ｃｂ）アルキニル基上の置換基Ｒ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２が２個以上存在するとき、それぞれのＲ５ａ、Ｒ１０ａ、Ｒ１５ａ、Ｒ１５ｂ、Ｒ１５ｃ、Ｒ１５ｄ、Ｒ２０、Ｒ２８、Ｒ２８ａ、Ｒ３１又はＲ３２は互いに同一でも異なってもよい。 Herein optionally substituted with R 5a (C a ~ C b ) alkynyl, optionally substituted with R 10a (C a ~ C b ) alkynyl, optionally substituted with R 15a (C a ~ C b) alkynyl, optionally substituted with R 15b (C a ~ C b ) alkynyl, optionally substituted with R 15c (C a ~ C b ) alkynyl, optionally substituted with R 15d (C a (C b ) alkynyl, optionally substituted with R 20 (C a -C b ) alkynyl, optionally substituted with R 28 (C a -C b ) alkynyl, optionally substituted with R 28a (C a ~ C b) alkynyl, which is optionally substituted with R 31 (C a ~ C b ) alkynyl or optionally substituted with R 32 (C a ~ C b ) notation alkynyl or the like, any of R 5a, R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 , wherein the hydrogen atom bonded to the carbon atom is arbitrarily substituted, and the above-mentioned meaning is composed of a to b carbon atoms Are selected within the range of each specified number of carbon atoms. At this time, the substituents R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31 or R 32 on each (C a -C b ) alkynyl group Each of R 5a , R 10a , R 15a , R 15b , R 15c , R 15d , R 20 , R 28 , R 28a , R 31, or R 32 may be the same or different. .
　本明細書における、
　〔Ｒ８ａはＲ９ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ８ａ及びＲ９ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、〕
　〔Ｒ１３ａはＲ１４ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ａ及びＲ１４ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、〕
　〔Ｒ１３ｂはＲ１４ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、〕
　〔Ｒ１８ｂはＲ１９ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１８ｂ及びＲ１９ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、〕
　〔Ｒ１８ｄはＲ１９ｄと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１８ｄ及びＲ１９ｄが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、〕
等の表記の具体例として、例えばアジリジン、アゼチジン、アゼチジン－２－オン、ピロリジン、ピロリジン－２－オン、オキサゾリジン、オキサゾリジン－２－オン、オキサゾリジン－２－チオン、チアゾリジン、チアゾリジン－２－オン、チアゾリジン－２－チオン、イミダゾリジン、イミダゾリジン－２－オン、イミダゾリジン－２－チオン、ピペリジン、ピペリジン－２－オン、ピペリジン－２－チオン、２Ｈ－３，４，５，６－テトラヒドロ－１，３－オキサジン－２－オン、２Ｈ－３，４，５，６－テトラヒドロ－１，３－オキサジン－２－チオン、モルホリン、２Ｈ－３，４，５，６－テトラヒドロ－１，３－チアジン－２－オン、２Ｈ－３，４，５，６－テトラヒドロ－１，３－チアジン－２－チオン、チオモルホリン、ペルヒドロピリミジン－２－オン、ピペラジン、ホモピペリジン、ホモピペリジン－２－オン、ヘプタメチレンイミン等が挙げられ、各々の指定の原子数の範囲で選択される。 In this specification,
[R 8a is by forming alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 9a, 3 ~ 8-membered ring together with the nitrogen atom to which R 8a and R 9a are bonded Wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
[R 13a is by forming alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 14a, 3 ~ 8-membered ring together with the nitrogen atom to which R 13a and R 14a are attached Wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
[R 13b is by forming alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 14b, 3 ~ 8-membered ring together with the nitrogen atom to which R 13b and R 14b are bonded Wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
[R 18b is by forming alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 19b, 3 ~ 8-membered ring together with the nitrogen atom to which R 18b and R 19b are bonded Wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
[R 18 d is by forming alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 19d, 3 ~ 8-membered ring together with the nitrogen atom to which R 18 d and R 19d are attached Wherein the alkylene chain or alkenylene chain may contain one oxygen atom, sulfur atom or nitrogen atom,
Specific examples of the notation include, for example, aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidine-2-one, oxazolidine-2-thione, thiazolidine, thiazolidine-2-one, thiazolidine -2-thione, imidazolidine, imidazolidine-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1, 3-Oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazine- 2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine, pe Tetrahydropyrimidine-2-one, piperazine, homopiperidine, homopiperidine-2-one, heptamethyleneimine, and the like, may be selected from the range of the number of each of the specified atoms.
　本明細書における
　〔Ｒ１４ｅはＲ１４ｆと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１４ｅ及びＲ１４ｆが結合する炭素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１、２又は３個含んでもよく、〕
の表記の具体例として、例えばシクロプロピリデン、シクロブチリデン、シクロペンチリデン、シクロヘキシリデン、オキセタン－３－イリデン、チエタン－３－イリデン、ジヒドロフラン－３－イリデン、ジヒドロチオフェン－３－イリデン、ジヒドロピラン－３－イリデン、ジヒドロピラン－４－イリデン、ジヒドロチオピラン－３－イリデン、ジヒドロチオピラン－４－イリデン、チアゾリジン－２－イリデン、２，３－ジヒドロチアゾール－２－イリデン、イミダゾリジン－２－イリデン、２，３－ジヒドロイミダゾール－２－イリデン、２，３－ジヒドロ－１，３，４－チアジアゾール－２－イリデン、１，２－ジヒドロピリジン－２－イリデン、２，３－ジヒドロピリダジン－３－イリデン、１，２－ジヒドロピラジン－２－イリデン、１，２－ジヒドロピリミジン－２－イリデン、６Ｈ－２，３－ジヒドロ－１，３，４－チアジアジン－２－イリデン等が挙げられ、各々の指定の原子数の範囲で選択される。 [R 14e herein by forming the alkenylene chain alkylene chain or C 2 ~ C 7 of C 2 ~ C 7 together with R 14f, 3 together with the carbon atom to which R 14e and R 14f are bonded May form an ˜8-membered ring, and this alkylene chain or alkenylene chain may contain 1, 2 or 3 oxygen atoms, sulfur atoms or nitrogen atoms.]
Specific examples of the notation include, for example, cyclopropylidene, cyclobutylidene, cyclopentylidene, cyclohexylidene, oxetane-3-ylidene, thietan-3-ylidene, dihydrofuran-3-ylidene, dihydrothiophene-3-ylidene, Dihydropyran-3-ylidene, dihydropyran-4-ylidene, dihydrothiopyran-3-ylidene, dihydrothiopyran-4-ylidene, thiazolidine-2-ylidene, 2,3-dihydrothiazol-2-ylidene, imidazolidine- 2-ylidene, 2,3-dihydroimidazol-2-ylidene, 2,3-dihydro-1,3,4-thiadiazole-2-ylidene, 1,2-dihydropyridine-2-ylidene, 2,3-dihydropyridazine 3-Ilidene, 1,2-dihydropyrazin-2-y Den, 1,2-dihydro-2-ylidene, 6H-2,3-dihydro-1,3,4-thiadiazine-2-ylidene and the like, may be selected from the range of the number of each of the specified atoms.
　本発明化合物は、以下の方法で製造することができる。
　製造法Ａ
Figure JPOXMLDOC01-appb-C000031
　式（６）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ６ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される化合物を、酸又は塩基と反応させて、式（７）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒａ及びｎは前記と同じ意味を表す。］で表される化合物を得ることができる。 The compound of the present invention can be produced by the following method.
Manufacturing method A
Figure JPOXMLDOC01-appb-C000031
Formula (6) [wherein A 1 , R 2 , R 3 , R 4 , R 6b , R a and n represent the same meaning as described above. And a compound represented by the formula (7) [wherein A 1 , R 2 , R 3 , R 4 , R a and n represent the same meaning as described above]. The compound represented by this can be obtained.
　酸としては、塩酸、硫酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等を用いることができる。塩基としては、炭酸カリウム、水酸化ナトリウム等を用いることができる。
　本反応は、無溶媒で実施してもよいが、溶媒を用いてもよい。例えば、アセトニトリル、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 As the acid, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, trifluoroacetic acid and the like can be used. As the base, potassium carbonate, sodium hydroxide or the like can be used.
This reaction may be carried out without solvent, but a solvent may be used. For example, polar solvents such as acetonitrile and water, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, and aromatic hydrocarbons such as benzene, toluene and xylene Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
　この様にして得られた式（７）で表される化合物を、式（８－１）［式中Ｒ７ｂは前記と同じ意味を表す。］で表される化合物と反応させて、式（９）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ７ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を合成することができる。本反応では式（７）で表される化合物１当量に対して、式（８－１）で表される化合物は、０．５～５０当量、好ましくは０．８～２当量の範囲で用いることができる。必要ならば、炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン等の塩基を使用することができる。本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 The compound represented by the formula (7) thus obtained is represented by the formula (8-1) [wherein R 7b represents the same meaning as described above. And a compound represented by formula (9) [wherein A 1 , R 2 , R 3 , R 4 , R 7b , R a and n represent the same meaning as described above]. This invention compound represented by this can be synthesize | combined. In this reaction, the compound represented by formula (8-1) is used in the range of 0.5 to 50 equivalents, preferably 0.8 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (7). be able to. If necessary, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used. This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
　式（８－１）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。
　また、式（７）で表される化合物を、縮合剤を用いて、式（８－２）［式中Ｒ７ｂは前記と同じ意味を表す。］で表される化合物と反応させて、式（９）で表される本発明化合物を合成することもできる。本反応では、式（８－２）で表される化合物１当量に対して１～４当量のＷＳＣ｛１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩｝、ＣＤＩ（カルボニルジイミダゾール）等の縮合剤を用いることができる。また、式（７）で表される化合物１当量に対して、式（８－２）で表される化合物を、０．５～５０当量、好ましくは０．８～２当量の範囲で用いることができる。必要ならば、炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン等の塩基を使用することができる。 Some of the compounds represented by formula (8-1) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
Further, the compound represented by the formula (7) is converted into the formula (8-2) using a condensing agent, wherein R 7b represents the same meaning as described above. The compound of the present invention represented by formula (9) can also be synthesized by reacting with the compound represented by formula (9). In this reaction, 1 to 4 equivalents of WSC {1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride}, CDI (carbonyldiimidazole) per 1 equivalent of the compound represented by formula (8-2) ) And the like can be used. Further, the compound represented by the formula (8-2) is used in the range of 0.5 to 50 equivalents, preferably 0.8 to 2 equivalents with respect to 1 equivalent of the compound represented by the formula (7). Can do. If necessary, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used.
　本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　式（８－２）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。 This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
Some of the compounds represented by formula (8-2) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
　製造法Ｂ
Figure JPOXMLDOC01-appb-C000032
 　式（２－１２）［式中Ｒ３、Ｒ４、Ｒ７ｂ及びＲａは前記と同じ意味を表す。］で表される化合物と式（２－２）［式中Ａ１、Ｒ２及びｎは前記と同じ意味を表し、Ｌ１はフッ素原子、塩素原子、臭素原子、ヨウ素原子、－Ｂ（ＯＨ）２基又は－Ｂ（ＯＲ５１）２基（式中Ｒ５１は、水素原子又は、同一又は異なってもよいＣ１～Ｃ６アルキルを表し、或いは、２つのＲ５１が一緒になって－ＣＨ２ＣＨ２－又は－Ｃ（ＣＨ３）２Ｃ（ＣＨ３）２－を形成してもよい）を表す。］で表される化合物を、触媒及び塩基の存在下で反応させることにより、式（９）で表される本発明化合物を得ることができる。 Manufacturing method B
Figure JPOXMLDOC01-appb-C000032
 Formula (2-12) [wherein R 3 , R 4 , R 7b and R a represent the same meaning as described above. And a compound represented by formula (2-2) [wherein A 1 , R 2 and n represent the same meaning as described above, L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, —B (OH ) 2 groups or —B (OR 51 ) 2 groups (wherein R 51 represents a hydrogen atom or C 1 to C 6 alkyl which may be the same or different, or two R 51 together represent — CH 2 CH 2 — or —C (CH 3 ) 2 C (CH 3 ) 2 — may be formed). The compound of the present invention represented by the formula (9) can be obtained by reacting the compound represented by formula (9) in the presence of a catalyst and a base.
　式（２－２）で表される化合物の量は、式（２－１２）で表される化合物１当量に対して０．８～５当量の範囲で、用いることができる。
　ここで用いられる式（２－２）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて合成することができる。
　本反応で使用できる触媒としては、例えば、パラジウム－炭素、塩化パラジウム、酢酸パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド、テトラキス（トリフェニルホスフィン）パラジウム等のパラジウム触媒又は金属銅、酢酸銅（Ｉ）、酢酸銅（ＩＩ）、酸化銅（Ｉ）、酸化銅（ＩＩ）、ヨウ化銅等の銅触媒が挙げられる。触媒の使用量は、式（２－１２）で表される化合物１当量に対して０．００１～１．０当量、好ましくは、０．０１～０．５当量、さらに好ましくは０．０５～０．２当量の範囲で、用いることができる。
　使用する塩基としては、例えば、ピリジン、ジイソプロピルエチルアミン、トリエチルアミン等の三級アミン化合物、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の無機塩基等が挙げられる。塩基の使用量は、式（２－１２）で表される化合物１当量に対して０．１～１０．０当量、好ましくは０．５～３当量の範囲で用いることができる。
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 The amount of the compound represented by the formula (2-2) can be used in the range of 0.8 to 5 equivalents relative to 1 equivalent of the compound represented by the formula (2-12).
Some of the compounds represented by the formula (2-2) used here are known compounds, and some of them are commercially available. Others can be synthesized according to the methods described in the literature.
Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, and copper (I) acetate. And copper catalysts such as copper (II) acetate, copper (I) oxide, copper (II) oxide and copper iodide. The amount of the catalyst to be used is 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 1 equivalent relative to 1 equivalent of the compound represented by formula (2-12). It can be used in the range of 0.2 equivalents.
Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. . The amount of the base used can be 0.1 to 10.0 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound represented by formula (2-12).
This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
　製造法Ｃ
Figure JPOXMLDOC01-appb-C000033
 　式（９）で表される化合物と、五硫化二燐、五硫化二燐－ＨＭＤＯ(ヘキサメチルジシロキサン)、ローソン試薬(Ｌａｗｅｓｓｏｎ’ｓ　Ｒｅａｇｅｎｔ；２,４－ビス(４－メトキシフェニル)－１,３,２,４－ジチアジホスフェタン－２,４－ジスルフィド)等の硫化剤を反応させることにより、式（３５）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ７ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。 Manufacturing method C
Figure JPOXMLDOC01-appb-C000033
 A compound represented by the formula (9), diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawesson's Reagent; 2,4-bis (4-methoxyphenyl) -1 , 3,2,4-dithiadiphosphetane-2,4-disulfide) and the like to react with a compound represented by the formula (35) [wherein A 1 , R 2 , R 3 , R 4 , R 7b , R a and n represent the same meaning as described above. This invention compound represented by this can be obtained.
　本反応で用いる硫化剤は、式（９）で表される化合物１当量に対して０．５～５０当量、好ましくは０．５～２当量の範囲で用いることができる。
　必要ならば、炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン等の塩基を使用することができる。
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 The sulfurizing agent used in this reaction can be used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (9).
If necessary, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used.
This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
　製造法Ｄ
Figure JPOXMLDOC01-appb-C000034
 　式（１３）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４及びｎは前記と同じ意味を表す。］で表される化合物を、製造法Ａと同様の方法を用いて、式（８－１）で表される化合物又は式（８－２）で表される化合物と反応させることにより、式（４１）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ７ｂ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。
　次いで、式（４１）で表される化合物を、式（５）［式中Ｒａは前記と同じ意味を表し、Jｂはハロゲン原子、－ＯＨ、－ＯＳＯ２ＣＨ３、－ＯＳＯ２ＣＦ３等の脱離基を表す。］で表される化合物と反応させることにより、式（９）で表される本発明化合物を得ることもできる。 Manufacturing method D
Figure JPOXMLDOC01-appb-C000034
 Formula (13) [wherein A 1 , R 2 , R 3 , R 4 and n represent the same meaning as described above. The compound represented by the formula (8-1) or the compound represented by the formula (8-2) is reacted with the compound represented by the formula (8-1) using the same method as the production method A. 41) [wherein A 1 , R 2 , R 3 , R 4 , R 7b and n represent the same meaning as described above. This invention compound represented by this can be obtained.
Next, the compound represented by the formula (41) is represented by the formula (5) [wherein R a represents the same meaning as described above, J b represents a halogen atom, —OH, —OSO 2 CH 3 , —OSO 2 CF 3 Represents a leaving group. The compound of the present invention represented by the formula (9) can also be obtained by reacting with the compound represented by formula (9).
　本反応は、式（４１）で表される化合物１当量に対して、式（５）で表される化合物を、０．５～５０当量、好ましくは０．５～２当量の範囲で用いることができる。必要ならば塩酸、硫酸、ｐ－トルエンスルホン酸等の酸、炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム等の塩基を、又は、ジエチルアゾジカルボキシレート及びトリフェニルホスフィン等を使用する光延反応を使用することができる。
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　式（５）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。 In this reaction, the compound represented by formula (5) is used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (41). Can do. If necessary, bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or diethyl Mitsunobu reaction using azodicarboxylate and triphenylphosphine can be used.
This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
Some of the compounds represented by formula (5) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
　製造法Ｅ
Figure JPOXMLDOC01-appb-C000035
 　式（９－２）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒａ、Ｒ１１ｂ、Ｒ１２ｂ及びｎは前記と同じ意味を表す。］で表される化合物を、実験化学講座（第５版）２００５年（日本化学会編　丸善株式会社）４１５頁等に記載の方法に準じて、オキシム部の幾何異性体である式（９－３）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒａ、Ｒ１１ｂ、Ｒ１２ｂ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることが出来る。又、同様にして式（９－３）で表される化合物から、式（９－２）で表される本発明化合物を得ることも出来る。 Manufacturing method E
Figure JPOXMLDOC01-appb-C000035
 Formula (9-2) [wherein A 1 , R 2 , R 3 , R 4 , R a , R 11b , R 12b and n represent the same meaning as described above. In accordance with the method described in Experimental Chemistry Course (5th edition) 2005 (Chemical Society of Japan, Maruzen Co., Ltd.), page 415, etc., the compound represented by the formula (9- 3) [wherein A 1 , R 2 , R 3 , R 4 , R a , R 11b , R 12b and n represent the same meaning as described above. This invention compound represented by this can be obtained. Similarly, the compound of the present invention represented by the formula (9-2) can also be obtained from the compound represented by the formula (9-3).
　製造法Ｆ
Figure JPOXMLDOC01-appb-C000036
 　式（９－４）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ１２ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される化合物を、製造法Ｅ同様の方法を用いて、オキシム部の幾何異性体である式（９－５）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ１２ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることが出来る。又、同様にして式（９－５）で表される化合物から、式（９－４）で表される本発明化合物を得ることも出来る。 Manufacturing method F
Figure JPOXMLDOC01-appb-C000036
 Formula (9-4) [wherein A 1 , R 2 , R 3 , R 4 , R 12b , R a and n represent the same meaning as described above. The compound represented by formula (9-5), which is a geometric isomer of the oxime moiety, is prepared in the same manner as in Production Method E, wherein A 1 , R 2 , R 3 , R 4 , R 12b , R a and n represent the same meaning as described above. This invention compound represented by this can be obtained. Similarly, the compound of the present invention represented by the formula (9-4) can also be obtained from the compound represented by the formula (9-5).
　製造法Ｇ
Figure JPOXMLDOC01-appb-C000037
 　式（７-Ｔ）［式中Ａ１、Ｒ２、Ｒ３、Ｒａ及びｎは前記と同じ意味を表す。］で表される化合物を、製造法Ａと同様の方法を用いて、式（８－１）又は式（８－２）で表される化合物と反応させることにより、式（９-Ｔ）［式中Ａ１、Ｒ２、Ｒ３、Ｒ７ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を合成することができる。
　式（７－Ｔ）で表される化合物は、国際公開第２０１０／１２９４９７号等の公知の方法により合成することができる。 Manufacturing method G
Figure JPOXMLDOC01-appb-C000037
 Formula (7-T) [wherein A 1 , R 2 , R 3 , R a and n represent the same meaning as described above. The compound represented by formula (9-T) is reacted with the compound represented by formula (8-1) or formula (8-2) using the same method as in Production Method A. In the formula, A 1 , R 2 , R 3 , R 7b , R a and n represent the same meaning as described above. This invention compound represented by this can be synthesize | combined.
The compound represented by the formula (7-T) can be synthesized by a known method such as International Publication No. 2010/129497.
　製造法Ｈ
Figure JPOXMLDOC01-appb-C000038
 　式（１３-Ｔ）［式中Ａ１、Ｒ２、Ｒ３及びｎは前記と同じ意味を表す。］で表される化合物を、製造法Ａと同様の方法を用いて式（８－１）で表される化合物又は式（８－２）で表される化合物と反応させることにより、式（４１-Ｔ）［式中Ａ１、Ｒ２、Ｒ３、Ｒ７ｂ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。
　式（１３－Ｔ）で表される化合物は、国際公開第２０１０／１２９４９７号等の公知の方法により合成することができる。
　次いで、式（４１-Ｔ）で表される化合物を、製造法Ｄと同様の方法を用いて式（５）で表される化合物と反応させることにより、式（９-Ｔ）［式中Ａ１、Ｒ２、Ｒ３、Ｒ７ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。 Manufacturing method H
Figure JPOXMLDOC01-appb-C000038
 Formula (13-T) [wherein A 1 , R 2 , R 3 and n represent the same meaning as described above. The compound represented by formula (41) is reacted with the compound represented by formula (8-1) or the compound represented by formula (8-2) by the same method as in Production Method A. -T) [wherein A 1 , R 2 , R 3 , R 7b and n represent the same meaning as described above. This invention compound represented by this can be obtained.
The compound represented by the formula (13-T) can be synthesized by a known method such as International Publication No. 2010/129497.
Next, the compound represented by the formula (41-T) is reacted with the compound represented by the formula (5) by using the same method as the production method D, thereby obtaining a compound represented by the formula (9-T) [in the formula A 1 , R 2 , R 3 , R 7b , R a and n represent the same meaning as described above. This invention compound represented by this can be obtained.
　製造法Ｉ
Figure JPOXMLDOC01-appb-C000039
 　式（９-Ｔ）で表される化合物と、製造法Ｃと同様の方法を用いて、五硫化二燐、五硫化二燐－ＨＭＤＯ(ヘキサメチルジシロキサン)、ローソン試薬(Ｌａｗｅｓｓｏｎ’ｓ　Ｒｅａｇｅｎｔ；２,４－ビス(４－メトキシフェニル)－１,３,２,４－ジチアジホスフェタン－２,４－ジスルフィド)等の硫化剤を反応させることにより、式（３５-Ｔ）［式中Ａ１、Ｒ２、Ｒ３、Ｒ７、Ｒａ及びｎは前記と同じ意味を表す。］で表される本発明化合物を得ることができる。 Manufacturing method I
Figure JPOXMLDOC01-appb-C000039
 Using a compound represented by the formula (9-T) and a method similar to Production Method C, diphosphorus pentasulfide, diphosphorus pentasulfide-HMDO (hexamethyldisiloxane), Lawson's Reagent; By reacting a sulfurizing agent such as 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-disulfide), the compound of the formula (35-T) [formula A 1 , R 2 , R 3 , R 7 , R a and n in the middle represent the same meaning as described above. This invention compound represented by this can be obtained.
　製造法Ｊ
Figure JPOXMLDOC01-appb-C000040
 　式（１７-Ｔ）［式中Ｒ３、Ｒ７ｂ及びＲａは前記と同じ意味を表し、Ｊａは水素原子、ハロゲン原子、－ＯＨ、－ＯＳＯ２ＣＨ３、－ＯＳＯ２ＣＦ３、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ５２等の脱離基を表し、Ｒ５２はＣ１～Ｃ６アルキル、フェニル等を表す。］と式（２－２）［式中Ａ１、Ｒ２及びｎは前記と同じ意味を表し、Ｌ１はフッ素原子、塩素原子、臭素原子、ヨウ素原子、－ＯＨ、－ＯＳＯ２ＣＨ３、－ＯＳＯ２ＣＦ３、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ５２（式中Ｒ５２は前記と同じ意味を表す。）、－Ｂ（ＯＨ）２基又は－Ｂ（ＯＲ５３）２基（式中Ｒ５３は、水素原子又は、同一又は異なってもよいＣ１～Ｃ６アルキルを表し、或いは、２つのＲ５３が一緒になって－ＣＨ２ＣＨ２－又は－Ｃ（ＣＨ３）２Ｃ（ＣＨ３）２－を形成してもよい）を表す。］で表される化合物を、触媒及び塩基の存在下で反応させることにより、式（９-Ｔ）で表される本発明化合物を得ることができる。
　式（２－２）で表される化合物の量は、式（１７-Ｔ）で表される化合物１当量に対して０．８～５当量、好ましくは０．８～２当量の範囲で、用いることができる。
　ここで用いられる式（２－２）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の方法に準じて合成することができる。 Manufacturing method J
Figure JPOXMLDOC01-appb-C000040
 Formula (17-T) [wherein R 3 , R 7b and R a are as defined above, J a is a hydrogen atom, a halogen atom, —OH, —OSO 2 CH 3 , —OSO 2 CF 3 , — It represents a leaving group such as C (O) OH, —C (O) OR 52 , and R 52 represents C 1 -C 6 alkyl, phenyl or the like. ] And formula (2-2) [wherein A 1 , R 2 and n represent the same meaning as described above, and L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, —OH, —OSO 2 CH 3 , —OSO 2 CF 3 , —C (O) OH, —C (O) OR 52 (wherein R 52 represents the same meaning as described above), —B (OH) 2 group or —B (OR 53 ) 2 A group (wherein R 53 represents a hydrogen atom or C 1 to C 6 alkyl which may be the same or different, or two R 53 together represent —CH 2 CH 2 — or —C (CH 3 ) 2 C (CH 3 ) 2 — may be formed). The compound of the present invention represented by the formula (9-T) can be obtained by reacting the compound represented by formula (9-T) in the presence of a catalyst and a base.
The amount of the compound represented by the formula (2-2) is in the range of 0.8 to 5 equivalents, preferably 0.8 to 2 equivalents with respect to 1 equivalent of the compound represented by the formula (17-T). Can be used.
Some of the compounds represented by the formula (2-2) used here are known compounds, and some of them are commercially available. Others can be synthesized according to the methods described in the literature.
　本反応で使用できる触媒としては、例えば、パラジウム－炭素、塩化パラジウム、酢酸パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド、テトラキス（トリフェニルホスフィン）パラジウム等のパラジウム触媒又は金属銅、酢酸銅（Ｉ）、酢酸銅（ＩＩ）、酸化銅（Ｉ）、酸化銅（ＩＩ）、ヨウ化銅等の銅触媒、ビス（１，５－シクロオクタジエン）ニッケル、ニッケル（ＩＩ）アセチルアセトナート等のニッケル触媒が挙げられる。触媒の使用量は、式（１７-Ｔ）で表される化合物１当量に対して０．００１～１．０当量、好ましくは、０．０１～０．５当量、さらに好ましくは０．０５～０．２当量の範囲で、用いることができる。
　使用する塩基としては、例えば、ピリジン、ジイソプロピルエチルアミン、トリエチルアミン等の三級アミン化合物、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム等の無機塩基等が挙げられる。塩基の使用量は、式（１７-Ｔ）で表される化合物１当量に対して０．１～１０．０当量、好ましくは０．５～３当量の範囲で用いることができる。 Examples of the catalyst that can be used in this reaction include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis (triphenylphosphine) palladium dichloride, tetrakis (triphenylphosphine) palladium, copper metal, and copper (I) acetate. Copper catalysts such as copper acetate (II), copper oxide (I), copper oxide (II) and copper iodide, nickel catalysts such as bis (1,5-cyclooctadiene) nickel and nickel (II) acetylacetonate Is mentioned. The amount of the catalyst used is 0.001 to 1.0 equivalent, preferably 0.01 to 0.5 equivalent, more preferably 0.05 to 1 equivalent, relative to 1 equivalent of the compound represented by the formula (17-T). It can be used in the range of 0.2 equivalents.
Examples of the base used include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium bicarbonate. . The amount of the base used can be 0.1 to 10.0 equivalents, preferably 0.5 to 3 equivalents, relative to 1 equivalent of the compound represented by the formula (17-T).
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。 This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
　製造法Ｋ
Figure JPOXMLDOC01-appb-C000041
 　式（１９-Ｔ）［式中Ｒ３、Ｒ７ｂ、Ｒａ及びＪａは前記と同じ意味を表す。］表される化合物と式（２－２）で表される化合物を、製造法Ｊと同様の方法で反応させることにより、式（４１-Ｔ）で表される本発明化合物を得ることができる。
　製造法Ａから製造法Ｋの反応は、必要であれば窒素、アルゴン等の不活性ガス雰囲気下で実施しても良い。
　製造法Ａから製造法Ｋの反応において、反応終了後の反応混合物は、直接濃縮、又は有機溶媒に溶解し、水洗後濃縮、又は氷水に投入、有機溶媒抽出後濃縮といった通常の後処理を行ない、目的の本発明化合物を得ることができる。また、精製の必要が生じたときには、再結晶、カラムクロマトグラフ、薄層クロマトグラフ、液体クロマトグラフ分取等の任意の精製方法によって分離、精製することができる。 Manufacturing method K
Figure JPOXMLDOC01-appb-C000041
 Formula (19-T) [wherein R 3 , R 7b , R a and J a represent the same meaning as described above. The compound of the present invention represented by the formula (41-T) can be obtained by reacting the compound represented by the formula (2-2) with the compound represented by the formula (2-2) in the same manner as in Production Method J. .
The reaction from production method A to production method K may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
In the reaction from production method A to production method K, the reaction mixture after completion of the reaction is directly concentrated, or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent. The objective compound of the present invention can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
　製造法Ａで用いられる式（６）で表される化合物は、例えば以下の反応式１～２のようにして合成することが出来る。
　反応式１
Figure JPOXMLDOC01-appb-C000042
 The compound represented by the formula (6) used in the production method A can be synthesized, for example, according to the following reaction formulas 1 and 2.
Reaction formula 1
Figure JPOXMLDOC01-appb-C000042
　式（２－１）［式中Ｒ３及びＲ４は前記と同じ意味を表し、Ｒ５０はＣ１～Ｃ６のアルキル基を表す。］で表される化合物は、シンレット　２００４年，４巻，７０３頁等の公知の方法により合成することができる。
　式（２－１）で表される化合物を、文献既知の公知の方法、例えばジャーナル　オブ　オーガニック　ケミストリー　２００４年，６９巻，５５７８頁等に記載の方法に準じて、公知の式（２－２）［式中Ａ１、Ｒ２及びｎは前記と同じ意味を表し、Ｌ１はフッ素原子、塩素原子、臭素原子、ヨウ素原子、－Ｂ（ＯＨ）２基又は－Ｂ（ＯＲ５１）２基（式中Ｒ５１は、水素原子又は、同一又は異なってもよいＣ１～Ｃ６アルキルを表し、或いは、２つのＲ５１が一緒になって－ＣＨ２ＣＨ２－又は－Ｃ（ＣＨ３）２Ｃ（ＣＨ３）２－を形成してもよい）を表す。］で表される化合物と、銅等の金属触媒及び塩基の存在下又はパラジウム等の遷移金属触媒及び塩基の存在下で反応させることにより、式（２－３）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４及びｎは前記と同じ意味を表し、Ｒ５０はＣ１～Ｃ６のアルキル基を表す。］の化合物を得ることができる。 Formula (2-1) [wherein R 3 and R 4 represent the same meaning as described above, and R 50 represents a C 1 -C 6 alkyl group. ] Can be synthesized by a known method such as Sinlet 2004, Vol. 4, 703.
The compound represented by the formula (2-1) is converted into a known formula (2-2) according to a known method known in the literature, for example, the method described in Journal of Organic Chemistry 2004, 69, 5578. [Wherein A 1 , R 2 and n represent the same meaning as described above, and L 1 represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, —B (OH) 2 group or —B (OR 51 ) 2 group ( In the formula, R 51 represents a hydrogen atom or C 1 to C 6 alkyl which may be the same or different, or two R 51 together represent —CH 2 CH 2 — or —C (CH 3 ) 2. C (CH 3 ) 2 — may be formed). ] In the presence of a metal catalyst such as copper and a base, or in the presence of a transition metal catalyst such as palladium and a base, a compound represented by formula (2-3) [wherein A 1 , R 2 , R 3 , R 4 and n represent the same meaning as described above, and R 50 represents a C 1 -C 6 alkyl group. Can be obtained.
　また、式（２－３）で表される化合物は、式（２－４）［式中Ｒ３、Ｒ４及びＲ５０は前記と同じ意味を表し、Ｒ５１はメトキシ基、エトキシ基、ジメチルアミノ基等の脱離基を表す。］で表される化合物と、式（２－５)［式中Ａ１、Ｒ２及びｎは前記と同じ意味を表す。］で表される化合物とを文献既知の方法、例えば、ジャーナル　オブ　ヘテロサイクリック　ケミストリー　１９８７年，２４巻，１６６９頁等に記載の方法に準じて、反応させることにより合成することができる。式（２－４）で表される化合物は、ジャーナル　オブ　ヘテロサイクリック　ケミストリー　１９８７年，２４巻，６９３頁等の公知の方法により、式（２－５)で表される化合物は、ジャーナル　オブ　メディシナル　ケミストリー　２００２年，４５巻，５３９７頁等の公知の方法により合成することができる。
　さらに式（２－３）で表される化合物を、文献既知の公知の方法に準じて加水分解反応させることにより、式（２）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４及びｎは前記と同じ意味を表す。］で表される化合物を製造することができる。 The compound represented by the formula (2-3) is represented by the formula (2-4) [wherein R 3 , R 4 and R 50 represent the same meaning as described above, and R 51 represents a methoxy group, an ethoxy group, a dimethyl group, Represents a leaving group such as an amino group. And a compound represented by formula (2-5) [wherein A 1 , R 2 and n represent the same meaning as described above. Can be synthesized according to a method known in the literature, for example, the method described in Journal of Heterocyclic Chemistry 1987, Vol. 24, page 1669. The compound represented by the formula (2-4) can be obtained by a known method such as Journal of Heterocyclic Chemistry 1987, 24, 693, etc., and the compound represented by the formula (2-5) can be obtained by using a journal of medicinal. Chemistry 2002, 45, 5397, etc. can be synthesized.
Further, the compound represented by the formula (2-3) is hydrolyzed according to a known method known in the literature to obtain a compound represented by the formula (2) [wherein A 1 , R 2 , R 3 , R 4 and n Represents the same meaning as described above. The compound represented by this can be manufactured.
　反応式２
Figure JPOXMLDOC01-appb-C000043
 　式（２）で表される化合物を、ジフェニルホスホリルアジド（ＤＰＰＡ）及び式（３）［式中Ｒ６ｂは前記と同じ意味を表す。］で表される化合物と反応させることにより、式（４）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ６ｂ及びｎは前記と同じ意味を表す。］で表される化合物を得ることができる。 Reaction formula 2
Figure JPOXMLDOC01-appb-C000043
 The compound represented by formula (2) is diphenylphosphoryl azide (DPPA) and formula (3) [wherein R 6b represents the same meaning as described above. In the formula (4), A 1 , R 2 , R 3 , R 4 , R 6b and n have the same meaning as described above. The compound represented by this can be obtained.
　本反応では、式（２）で表される化合物１当量に対して、ＤＰＰＡは０．５～５０当量、好ましくは０．５～２当量の範囲で用いることができ、式（３）で表される化合物は、式（２）で表される化合物１当量に対して、1当量から溶媒量の範囲で用いることができる。必要ならば炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン等の塩基を使用することができる。
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　式（３）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。 In this reaction, DPPA can be used in the range of 0.5 to 50 equivalents, preferably 0.5 to 2 equivalents, relative to 1 equivalent of the compound represented by formula (2). The compound to be used can be used in the range of 1 equivalent to a solvent amount with respect to 1 equivalent of the compound represented by the formula (2). If necessary, a base such as potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine can be used.
This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
　引き続き式（４）で表される化合物を、製造法Ｄと同様の方法を用いて、式（５）［式中Ｒａは前記と同じ意味を表し、Ｊｂはハロゲン原子、－ＯＨ、－ＯＳＯ２ＣＨ３、－ＯＳＯ２ＣＦ３等の脱離基を表す。］で表される化合物と反応させることにより、式（６）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４、Ｒ６ｂ、Ｒａ及びｎは前記と同じ意味を表す。］で表される化合物を得ることができる。 Subsequently, the compound represented by formula (4) was prepared by using the same method as in Production Method D, using formula (5) [wherein R a represents the same meaning as described above, J b represents a halogen atom, —OH, — It represents a leaving group such as OSO 2 CH 3 or —OSO 2 CF 3 . In the formula (6), A 1 , R 2 , R 3 , R 4 , R 6b , R a and n have the same meaning as described above. The compound represented by this can be obtained.
　製造法Ｂで用いられる式（２－１２）で表される化合物は、例えば以下のようにして合成することが出来る。
　反応式３
Figure JPOXMLDOC01-appb-C000044
 The compound represented by formula (2-12) used in production method B can be synthesized, for example, as follows.
Reaction formula 3
Figure JPOXMLDOC01-appb-C000044
　式（２－６）［式中Ｒ３、Ｒ４及びＲ５０は前記と同じ意味を表し、Ｐ１はターシャリーブチル、ベンジル、４-メトキシベンジル、アセチル、ベンゾイル、ベンゼンスルホニル、ｐ－トルエンスルホニル、メタンスルホニル、メトキシメチル又はメチルチオメチル等の保護基を表す。］で表される化合物は、ジャーナル　オブ　ヘテロサイクリック　ケミストリー　１９８７年，２４巻，６９３頁等の公知の方法により合成することができる。
　式（２－６）で表される化合物を、文献既知の公知の方法に準じて加水分解反応させることにより、式（２－７）［式中Ｒ３、Ｒ４及びＰ１は前記と同じ意味を表す。］で表される化合物を製造することができる。
　引き続き、式（２－７）で表される化合物から上記反応式２と同様の方法を用いて、式（２－８）［式中Ｒ３、Ｒ４、Ｒ６ｂ及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することができる。
　次いで、式（２－８）で表される化合物と式（５）で表される化合物とを、反応式２と同様の方法で反応させることにより、式（２－９）［式中Ｒ３、Ｒ４、Ｒａ、Ｒ６ｂ及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することができる。
　更に、式（２－９）で表される化合物から、製造法Ａに従って式（２－１０）［式中Ｒ３、Ｒ４、Ｒａ及びＰ１は前記と同じ意味を表す。］で表される化合物を経由し、式（２－１１）［式中Ｒ３、Ｒ４、Ｒ７ｂ、Ｒａ及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することができる。
　このようにして合成した式（２－１１）で表される化合物を酸で、脱保護することにより、式（２－１２）［式中Ｒ３、Ｒ４、Ｒ７ｂ及びＲａは前記と同じ意味を表す。］で表される化合物を合成することができる。 Formula (2-6) [wherein R 3 , R 4 and R 50 represent the same meaning as described above, and P 1 represents tertiary butyl, benzyl, 4-methoxybenzyl, acetyl, benzoyl, benzenesulfonyl, p-toluenesulfonyl. Represents a protecting group such as methanesulfonyl, methoxymethyl or methylthiomethyl. ] Can be synthesized by known methods such as Journal of Heterocyclic Chemistry 1987, 24, 693.
By hydrolyzing the compound represented by the formula (2-6) according to a known method known in the literature, the compound represented by the formula (2-7) [wherein R 3 , R 4 and P 1 are the same as those described above] Represents meaning. The compound represented by this can be manufactured.
Subsequently, the compound represented by the formula (2-7) is used in the same manner as in the above reaction formula 2, and then the formula (2-8) [wherein R 3 , R 4 , R 6b and P 1 are the same as described above] Represents meaning. ] Can be synthesized.
Next, the compound represented by the formula (2-8) and the compound represented by the formula (5) are reacted in the same manner as in the reaction formula 2, thereby obtaining the formula (2-9) [wherein R 3 , R 4 , R a , R 6b and P 1 represent the same meaning as described above. ] Can be synthesized.
Further, from the compound represented by formula (2-9), according to production method A, formula (2-10) [wherein R 3 , R 4 , R a and P 1 represent the same meaning as described above. The compound represented by formula (2-11) [wherein R 3 , R 4 , R 7b , R a and P 1 represent the same meaning as described above. ] Can be synthesized.
The compound represented by the formula (2-11) synthesized in this manner is deprotected with an acid to give the formula (2-12) [wherein R 3 , R 4 , R 7b and R a are as defined above. Represents the same meaning. ] Can be synthesized.
　製造法Ａで用いられる式（７）で表される化合物は、例えば以下のようにして合成することが出来る。
　反応式４
Figure JPOXMLDOC01-appb-C000045
 　式（２－１３）［式中Ｒ３、Ｒ４及びＲａは前記と同じ意味を表す。］で表される化合物は、国際公開第２０１１／０４８０８２号明細書等の公知の方法により合成することができる。
　式（２－１３）で表される化合物と式（２－２）で表される化合物を、製造法Ｂと同様の方法で反応させることにより、式（７）で表される化合物を合成することができる。 The compound represented by the formula (7) used in the production method A can be synthesized, for example, as follows.
Reaction formula 4
Figure JPOXMLDOC01-appb-C000045
 Formula (2-13) [wherein R 3, R 4 and R a are as defined above. ] Can be synthesized by a known method such as International Publication No. 2011/048082.
The compound represented by formula (7) is synthesized by reacting the compound represented by formula (2-13) with the compound represented by formula (2-2) in the same manner as in Production Method B. be able to.
　製造法Ｄで用いられる式（１３）で表される化合物は、例えば以下のようにして合成することが出来る。
　反応式５
Figure JPOXMLDOC01-appb-C000046
 The compound represented by Formula (13) used in Production Method D can be synthesized, for example, as follows.
Reaction formula 5
Figure JPOXMLDOC01-appb-C000046
　式（２）で表される化合物を酸無水物存在下、ニトロ化剤と反応させることにより式（２－１４）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４及びｎは前記と同じ意味を表す。］で表される化合物を合成することが出来る。
　また、式（２－１４）で表される化合物は、式（２－１５）で表される化合物を文献既知の方法、例えば、ジャーナル　オブ　ヘテロサイクリック　ケミストリー　１９８１年，１８巻，９頁等に記載の方法に準じて、反応させることにより合成することができる。式（２－１５）で表される化合物は、ヨーロピアン　ジャーナル　オブ　オーガニック　ケミストリー　２００４年，４号，６９５頁等の公知の方法により合成することができる。
　更に、式（２－１４）で表される化合物は、式（２－１６）で表される化合物と式（２－２）で表される化合物とを、製造法Ｂと同様の方法で反応させることにより合成することが出来る。
　式（２－１６）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。
　続いて、式（２－１４）で表される化合物を、公知のニトロ基の還元法により式（１３）［式中Ａ１、Ｒ２、Ｒ３、Ｒ４及びｎは前記と同じ意味を表す。］で表される化合物を合成することが出来る。
　式（１３）で表される化合物は、式（２）で表される化合物を文献既知の方法、例えば、薬学雑誌　１９９０年，１１０巻，４５７頁等に記載の方法に準じて、ジフェニルリン酸アジド（ＤＰＰＡ）と反応させることにより合成することができる。式（２－１４ｂ）で表される化合物を更に、文献既知の方法、例えば、テトラへドロン　２０１３年，６９巻，３９５頁等に記載の方法に準じて反応させることにより合成することができる。 By reacting the compound represented by the formula (2) with a nitrating agent in the presence of an acid anhydride, the formula (2-14) [wherein A 1 , R 2 , R 3 , R 4 and n are the same as defined above] Represents meaning. ] Can be synthesized.
In addition, the compound represented by the formula (2-14) is obtained by converting the compound represented by the formula (2-15) into a method known in the literature, for example, Journal of Heterocyclic Chemistry 1981, Vol. 18, p. According to the method described, it can be synthesized by reacting. The compound represented by the formula (2-15) can be synthesized by a known method such as European Journal of Organic Chemistry 2004, No. 4, page 695.
Further, the compound represented by the formula (2-14) is obtained by reacting the compound represented by the formula (2-16) and the compound represented by the formula (2-2) in the same manner as in Production Method B. Can be synthesized.
Some of the compounds represented by formula (2-16) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
Subsequently, the compound represented by the formula (2-14) is converted into the formula (13) by the known nitro group reduction method, wherein A 1 , R 2 , R 3 , R 4 and n have the same meaning as described above. To express. ] Can be synthesized.
The compound represented by the formula (13) is obtained by converting the compound represented by the formula (2) into a diphenyl phosphate according to a method known in the literature, for example, the method described in Pharmaceutical Journal 1990, 110, 457, etc. It can be synthesized by reacting with azide (DPPA). The compound represented by the formula (2-14b) can be further synthesized by reacting according to a method known in the literature, for example, the method described in Tetrahedron 2013, 69, 395.
　反応式６
Figure JPOXMLDOC01-appb-C000047
 　式（２－７）で表される化合物を文献既知の方法、例えば、テトラへドロン　レタース　２００３年，４４巻，７６２９頁等に記載の方法に準じて、反応させることにより式（２－１７）［式中Ｒ３、Ｒ４及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することができる。
　続いて、式（２－１７）で表される化合物を文献既知の方法、例えば、実験化学講座　第５版（日本化学会編）　２００５年，１４巻，３７４頁等に記載の方法に準じて式（２－１８）［式中Ｍはナトリウム、カリウム等のアルカリ金属を表す。］で表される化合物又は式（２－１９）［式中Ｍは前記と同じ意味を表す。］で表される化合物と反応させることにより式（２－２０）［式中Ｒ３、Ｒ４及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することができる。
　更に、式（２－２０）で表される化合物を、製造法Ａと同様の方法を用いて反応させることにより式（２－２１）［式中Ｒ３、Ｒ４、Ｒ７ｂ及びＰ１は前記と同じ意味を表す。］で表される化合物を合成することが出来る。
　このようにして合成した式（２－２１）で表される化合物を酸又は塩基で、脱保護することにより、式（２－２２）［式中Ｒ３、Ｒ４及びＲ７ｂは前記と同じ意味を表す。］で表される化合物を合成することができる。 Reaction formula 6
Figure JPOXMLDOC01-appb-C000047
 The compound represented by the formula (2-7) is reacted according to a method known in the literature, for example, the method described in Tetrahedron Letters 2003, 44, 7629, etc. [Wherein R 3 , R 4 and P 1 represent the same meaning as described above. ] Can be synthesized.
Subsequently, the compound represented by the formula (2-17) is converted into a method known in the literature, for example, according to the method described in Experimental Chemistry Course 5th Edition (Edited by The Chemical Society of Japan) 2005, Vol. 14, p. Formula (2-18) [wherein M represents an alkali metal such as sodium or potassium. Or a compound represented by formula (2-19) [wherein M represents the same meaning as described above. And a compound represented by formula (2-20) [wherein R 3 , R 4 and P 1 represent the same meaning as described above. ] Can be synthesized.
Further, the compound represented by the formula (2-20) is reacted by using the same method as in the production method A to thereby convert the compound represented by the formula (2-21) [wherein R 3 , R 4 , R 7b and P 1 are Represents the same meaning as above. ] Can be synthesized.
The compound represented by the formula (2-21) synthesized in this manner is deprotected with an acid or a base, whereby the formula (2-22) [wherein R 3 , R 4 and R 7b are the same as those described above] Represents meaning. ] Can be synthesized.
　反応式７
Figure JPOXMLDOC01-appb-C000048
 　式（８－３）［式中Ｒ１１ｂ、Ｒ５０、Ｊｂは前記と同じ意味を表し、Ｒ６０及びＲ６１は、各々独立して水素原子、Ｃ１～Ｃ６のアルキル基又はＲ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル基を表し、Ｒ１５ｃは前記と同じ意味を表し、ｔは０～６の整数を表す。］で表される化合物は、例えば、独国特許出願公開第３２２０５２４号明細書等の公知の方法に準じて合成することができる。
　式（８－４）［式中Ｒ１６ｃは前記と同じ意味を表す。］で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。
　式（８－３）で表される化合物を、式（８－４）で表される化合物と反応させることにより、式（８－５）［式中Ｒ１１ｂ、Ｒ１６ｃ、Ｒ５０、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を得ることができる。
　本反応は、式（８－３）で表される化合物１当量に対して、式（８－４）で表される化合物を、０．５～５０当量、好ましくは０．８～３当量の範囲で用いることができる。必要ならば塩酸、硫酸、ｐ－トルエンスルホン酸等の酸、炭酸カリウム、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン、水素化ナトリウム、水酸化ナトリウム、水酸化カリウム等の塩基を、又は、ジエチルアゾジカルボキシレート及びトリフェニルホスフィン等を使用する光延反応を使用することができる。 Reaction formula 7
Figure JPOXMLDOC01-appb-C000048
 Formula (8-3) [wherein R 11b , R 50 and J b represent the same meaning as described above, and R 60 and R 61 each independently represent a hydrogen atom, a C 1 -C 6 alkyl group or R 15c. Represents a (C 1 -C 6 ) alkyl group optionally substituted with, R 15c represents the same meaning as described above, and t represents an integer of 0 to 6. ] Can be synthesized according to a known method such as German Patent Application Publication No. 3220524.
Formula (8-4) [wherein R 16c represents the same meaning as described above. Some of the compounds represented by] are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
By reacting the compound represented by the formula (8-3) with the compound represented by the formula (8-4), the compound represented by the formula (8-5) [wherein R 11b , R 16c , R 50 , R 60 , R 61 and t have the same meaning as described above. The compound represented by this can be obtained.
In this reaction, 0.5 to 50 equivalents, preferably 0.8 to 3 equivalents, of the compound represented by formula (8-4) is used per 1 equivalent of the compound represented by formula (8-3). Can be used in a range. If necessary, bases such as hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, etc., potassium carbonate, triethylamine, pyridine, 4- (dimethylamino) pyridine, sodium hydride, sodium hydroxide, potassium hydroxide, or diethyl Mitsunobu reaction using azodicarboxylate and triphenylphosphine can be used.
　本反応は、無溶媒でも実施することができるが、溶媒を用いてもよい。例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン、水等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－６０℃から反応混合物の還流温度までの任意の温度を設定することができ、反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　また、式（８－８）［式中Ｒ１６ｃ、Ｒ５０、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を、国際公開第２００７／０２６２２１号等に記載の方法等に準じて、式（８－９）［式中Ｒ１１ｂは前記と同じ意味を表す。］で表される化合物と反応させることにより、式（８－５）で表される化合物を得ることもできる。
　次に、式（８－５）で表される化合物を、文献既知の公知の方法に準じて加水分解反応させることにより、式（８－６）［式中Ｒ１１ｂ、Ｒ１６ｃ、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を得ることができる。
　引き続き、式（８－６）で表される化合物を、文献既知の公知の方法に準じて塩化チオニル又はオキサリルクロリド等のハロゲン化剤と反応させることにより、式（８－７）［式中Ｒ１１ｂ、Ｒ１６ｃ、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を得ることができる。 This reaction can be carried out without solvent, but a solvent may be used. For example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, water and other polar solvents, methanol, ethanol, propanol, 2-propanol, ethylene glycol Alcohols such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, pentane and n-hexane And aliphatic hydrocarbons. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −60 ° C. to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but is usually arbitrary within the range of 5 minutes to 100 hours. Can be set.
In addition, formula (8-8) [wherein R 16c , R 50 , R 60 , R 61 and t represent the same meaning as described above. The compound represented by formula (8-9) [wherein R 11b represents the same meaning as described above] according to the method described in International Publication No. 2007/026221. The compound represented by formula (8-5) can also be obtained by reacting with the compound represented by formula (8).
Next, the compound represented by the formula (8-5) is subjected to a hydrolysis reaction according to a known method known in the literature to obtain a compound represented by the formula (8-6) [wherein R 11b , R 16c , R 60 , R 61 and t represent the same meaning as described above. The compound represented by this can be obtained.
Subsequently, by reacting the compound represented by the formula (8-6) with a halogenating agent such as thionyl chloride or oxalyl chloride according to a known method known in the literature, a compound represented by the formula (8-7) [in the formula, 11b , R 16c , R 60 , R 61 and t have the same meaning as described above. The compound represented by this can be obtained.
　反応式８
Figure JPOXMLDOC01-appb-C000049
 　式（８－８）［式中Ｒ１６ｃ、Ｒ５０、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を、国際公開第２００９／１０２９９７号等に記載の方法等に準じて、式（８－１０）［式中Ｒ１３ｂ及びＲ１４ｂは前記と同じ意味を表す。］で表される化合物と反応させることにより、式（８－１２）［式中Ｒ１３ｂ、Ｒ１４ｂ、Ｒ１６ｃ、Ｒ５０、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を得ることができる。
　式（８－１０）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて合成することができる。
　また、ジャーナル　オブ　ザ　ケミカル　ソサエティー　パーキン　トランスアクションズ　１　１９８１年，１８巻，９頁等に記載の公知の方法により合成することができる式（８－１１）［式中Ｒ１３ｂ、Ｒ１４ｂ、Ｒ５０、Ｒ６０、Ｒ６１、Ｊｂ及びｔは前記と同じ意味を表す。］で表される化合物を、式（８－４）で表される化合物と反応式７と同様の方法を用いて反応させることにより式（８－１２）で表される化合物を合成することも出来る。
　続いて、式（８－１２）で表される化合物を、反応式７と同様の方法を用いて反応させることにより、式（８－１３）［式中Ｒ１３ｂ、Ｒ１４ｂ、Ｒ１６ｃ、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物及び式（８－１４）［式中Ｒ１３ｂ、Ｒ１４ｂ、Ｒ１６ｃ、Ｒ６０、Ｒ６１及びｔは前記と同じ意味を表す。］で表される化合物を得ることができる。 Reaction formula 8
Figure JPOXMLDOC01-appb-C000049
 Formula (8-8) [wherein R 16c , R 50 , R 60 , R 61 and t represent the same meaning as described above. The compound represented by formula (8-10) [wherein R 13b and R 14b represent the same meaning as described above, according to the method described in International Publication No. 2009/102997 and the like. In the formula (8-12), R 13b , R 14b , R 16c , R 50 , R 60 , R 61 and t have the same meaning as described above. The compound represented by this can be obtained.
Some of the compounds represented by formula (8-10) are known compounds, and some of them are commercially available. Others can be synthesized according to known methods described in the literature.
In addition, Formula (8-11) which can be synthesized by a known method described in Journal of the Chemical Society Parkin Transactions 1 1981, Vol. 18, p. 9, etc. [wherein R 13b , R 14b , R 50 , R 60 , R 61 , J b and t represent the same meaning as described above. The compound represented by the formula (8-12) may be synthesized by reacting the compound represented by the formula (8-4) with the compound represented by the formula (8-4) by the same method as the reaction formula 7. I can do it.
Subsequently, the compound represented by the formula (8-12) is reacted using the same method as in the reaction formula 7, thereby obtaining the formula (8-13) [wherein R 13b , R 14b , R 16c , R 60 , R 61, and t represent the same meaning as described above. And a compound represented by formula (8-14): wherein R 13b , R 14b , R 16c , R 60 , R 61 and t have the same meanings as described above. The compound represented by this can be obtained.
　反応式９
Figure JPOXMLDOC01-appb-C000050
 　式（１４-Ｔ）［式中Ｒ３、Ｒ６ｂ及びＪａは前記と同じ意味を表す。］で表される化合物と、式（５）で表される化合物とを製造法Ｂと同様の方法を用いて反応させることにより、式（１５-Ｔ）［式中Ｒ３、Ｒａ、Ｒ６ｂ及びＪａは前記と同じ意味を表す。］で表される化合物を得ることができる。式（１４-Ｔ）で表される化合物は、文献既知の公知の方法、例えばバイオオーガニック　メディシナル　ケミストリー　レタース２０１０年，２０巻，１５５９頁等に記載の方法に準じて容易に製造することができる。
　引き続き、式（１５-Ｔ）で表される化合物を、製造法Ａと同様の方法を用いて酸又は塩基と反応させて、式（１６-Ｔ）［式中Ｒ３、Ｒａ及びＪａは前記と同じ意味を表す。］で表される化合物を得ることができる。
　更に、式（１６-Ｔ）で表される化合物を、製造法Ａと同様の方法を用いて式（８－１）で表される化合物又は式（８－２）で表される化合物と反応させることにより式（１７-Ｔ）で表される化合物を得ることができる。
　また、式（１４-Ｔ）で表される化合物を、反応式１と同様に酸又は塩基と反応させて、式（１８-Ｔ）［式中Ｒ３及びＪａは前記と同じ意味を表す。］で表される化合物を得ることができる。
　引き続き、式（１８-Ｔ）で表される化合物を、製造法Ａと同様の方法を用いて式（８－１）で表される化合物又は式（８－２）で表される化合物と反応させることにより、式（１９-Ｔ）で表される化合物を得ることができる。
　更に、式（１９-Ｔ）で表される化合物と、式（５）で表される化合物とを製造法Ｂと同様の方法を用いて反応させることにより、式（１７-Ｔ）で表される化合物を得ることができる。 Reaction formula 9
Figure JPOXMLDOC01-appb-C000050
 Formula (14-T) [wherein R 3 , R 6b and J a represent the same meaning as described above. The compound represented by formula (5) is reacted with the compound represented by formula (5) using the same method as in Production Method B, thereby producing a compound represented by formula (15-T) [wherein R 3 , R a , R 6b and J a represent the same meaning as described above. The compound represented by this can be obtained. The compound represented by the formula (14-T) can be easily produced according to a known method known in the literature, for example, a method described in Bioorganic Medicinal Chemistry Letters 2010, 20th, 1559, etc.
Subsequently, the compound represented by the formula (15-T) is reacted with an acid or a base using the same method as in Production Method A to obtain a compound represented by the formula (16-T) [wherein R 3 , R a and J a Represents the same meaning as described above. The compound represented by this can be obtained.
Further, the compound represented by the formula (16-T) is reacted with the compound represented by the formula (8-1) or the compound represented by the formula (8-2) by using the same method as in Production Method A. To obtain a compound represented by the formula (17-T).
Further, the compound represented by the formula (14-T) is reacted with an acid or a base in the same manner as in the reaction formula 1, and the formula (18-T) [wherein R 3 and J a represent the same meaning as described above. . The compound represented by this can be obtained.
Subsequently, the compound represented by the formula (18-T) is reacted with the compound represented by the formula (8-1) or the compound represented by the formula (8-2) by using the same method as in Production Method A. By doing so, a compound represented by the formula (19-T) can be obtained.
Furthermore, by reacting the compound represented by the formula (19-T) with the compound represented by the formula (5) using the same method as in Production Method B, the compound represented by the formula (17-T) is represented. Can be obtained.
　本発明に包含される活性化合物としては、具体的に例えば第１表乃至第４表に示す化合物が挙げられる。但し、第１表乃至第４表の化合物は例示のためのものであって、本発明はこれらのみに限定されるものではない。尚、表中、Ｍｅと記載される置換基はメチル基を表し、以下、Ｅｔとの記載はエチル基を表し、ｎ－Ｐｒ及びＰｒ－ｎはノルマルプロピル基を、ｉ－Ｐｒ及びＰｒ－ｉはイソプロピル基を、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピル基を、ｎ－Ｂｕ及びＢｕ－ｎはノルマルブチル基を、ｓ－Ｂｕ及びＢｕ－ｓはセカンダリーブチル基を、ｉ－Ｂｕ及びＢｕ－ｉはイソブチル基を、ｔ－Ｂｕ及びＢｕ－ｔはターシャリーブチル基を、ｃ－Ｂｕ及びＢｕ－ｃはシクロブチル基を、ｎ－Ｐｅｎ及びＰｅｎ－ｎはノルマルペンチル基を、ｃ－Ｐｅｎ及びＰｅｎ－ｃはシクロペンチル基を、ｎ－Ｈｅｘ及びＨｅｘ－ｎはノルマルヘキシル基を、ｃ－Ｈｅｘ及びＨｅｘ－ｃはシクロヘキシル基を、Ｈｅｐｔはヘプチル基を、Ｏｃｔはオクチル基を、Ｐｈはフェニル基をそれぞれ表す。
　表中、Ｄ１－２ａ、Ｄ１－７ｂ、Ｄ１－３２ａ、Ｄ１－３２ｂ、Ｄ１－３２ｃ、Ｄ１－３３ａ、Ｄ１－３４ａ、Ｄ１－３７ａ、Ｄ１－７９ａ、Ｄ１－７９ｂ、Ｄ１－８０ａ、Ｄ１－８０ｂ、Ｄ１－８０ｃ、Ｄ１－８０ｄ、Ｄ１－８０ｅ、Ｄ１－８０ｆ、Ｄ１－８７ａ、Ｄ１－９８ａ、Ｄ１－１０３ｍ、Ｄ１－１０３ｏ、Ｄ１－１０３ｐ、Ｄ１－１０３ｑ、Ｄ１－１０８ａ、Ｄ１－１０８ｂ、Ｄ１－１０８ｃ、Ｄ１－１０４ａ、Ｄ１－１０４ｂ、及びＤ１－１０４ｃで表される構造は下記の構造を表し、Ｄ１－７ｂ、及びＤ１－３２ｂの構造式に記された番号は、Ｘ１の置換位置を表し、Ｘ１ｂの置換位置を表し、Ｄ１－１０８ｂの構造式に記された番号は、Ｚの置換位置を表す。 Specific examples of the active compound included in the present invention include compounds shown in Tables 1 to 4. However, the compounds in Tables 1 to 4 are for illustrative purposes, and the present invention is not limited thereto. In the table, a substituent described as Me represents a methyl group, hereinafter, Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, i-Pr and Pr-i Is an isopropyl group, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n are normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i-Bu and Bu-- i is an isobutyl group, t-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, c-Pen and Pen -C is a cyclopentyl group, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, Hept is a heptyl group, Oct is an octyl group, and Ph is a hexyl group. It represents a sulfonyl group, respectively.
In the table, D1-2a, D1-7b, D1-32a, D1-32b, D1-32c, D1-33a, D1-34a, D1-37a, D1-79a, D1-79b, D1-80a, D1-80b , D1-80c, D1-80d, D1-80e, D1-80f, D1-87a, D1-98a, D1-103m, D1-103o, D1-103p, D1-103q, D1-108a, D1-108b, D1 -108c, D1-104a, D1-104b, and structures represented by D1-104c represents the following structures, D1-7b, and structure number marked on the type D1-32b the substitution position of X 1 Represents the substitution position of X 1b , and the number written in the structural formula of D1-108b represents the substitution position of Z.
Figure JPOXMLDOC01-appb-C000051
Figure JPOXMLDOC01-appb-C000051
第１表
Figure JPOXMLDOC01-appb-C000052
 Table 1
Figure JPOXMLDOC01-appb-C000052
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000053
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000054
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000055
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000056
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000057
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000058
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000059
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000060
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000061
Figure JPOXMLDOC01-appb-C000062
Figure JPOXMLDOC01-appb-C000062
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000063
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000064
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000065
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000066
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000067
Figure JPOXMLDOC01-appb-C000068
Figure JPOXMLDOC01-appb-C000068
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-I000076
Figure JPOXMLDOC01-appb-I000076
Figure JPOXMLDOC01-appb-I000077
Figure JPOXMLDOC01-appb-I000077
Figure JPOXMLDOC01-appb-I000078
Figure JPOXMLDOC01-appb-I000078
Figure JPOXMLDOC01-appb-I000079
Figure JPOXMLDOC01-appb-I000079
Figure JPOXMLDOC01-appb-I000080
Figure JPOXMLDOC01-appb-I000080
Figure JPOXMLDOC01-appb-I000081
Figure JPOXMLDOC01-appb-I000081
Figure JPOXMLDOC01-appb-I000082
Figure JPOXMLDOC01-appb-I000082
Figure JPOXMLDOC01-appb-I000083
Figure JPOXMLDOC01-appb-I000083
Figure JPOXMLDOC01-appb-I000084
Figure JPOXMLDOC01-appb-I000084
Figure JPOXMLDOC01-appb-I000085
Figure JPOXMLDOC01-appb-I000085
Figure JPOXMLDOC01-appb-I000086
Figure JPOXMLDOC01-appb-I000086
Figure JPOXMLDOC01-appb-I000087
Figure JPOXMLDOC01-appb-I000087
Figure JPOXMLDOC01-appb-I000088
Figure JPOXMLDOC01-appb-I000088
Figure JPOXMLDOC01-appb-I000089
Figure JPOXMLDOC01-appb-I000089
Figure JPOXMLDOC01-appb-I000090
Figure JPOXMLDOC01-appb-I000090
Figure JPOXMLDOC01-appb-I000091
Figure JPOXMLDOC01-appb-I000091
Figure JPOXMLDOC01-appb-I000092
Figure JPOXMLDOC01-appb-I000092
Figure JPOXMLDOC01-appb-I000093
Figure JPOXMLDOC01-appb-I000093
Figure JPOXMLDOC01-appb-I000094
Figure JPOXMLDOC01-appb-I000094
Figure JPOXMLDOC01-appb-I000095
Figure JPOXMLDOC01-appb-I000095
Figure JPOXMLDOC01-appb-I000096
Figure JPOXMLDOC01-appb-I000096
Figure JPOXMLDOC01-appb-I000097
Figure JPOXMLDOC01-appb-I000097
Figure JPOXMLDOC01-appb-I000098
Figure JPOXMLDOC01-appb-I000098
Figure JPOXMLDOC01-appb-I000099
Figure JPOXMLDOC01-appb-I000099
Figure JPOXMLDOC01-appb-I000100
Figure JPOXMLDOC01-appb-I000100
Figure JPOXMLDOC01-appb-I000101
Figure JPOXMLDOC01-appb-I000101
Figure JPOXMLDOC01-appb-I000102
Figure JPOXMLDOC01-appb-I000102
Figure JPOXMLDOC01-appb-I000103
Figure JPOXMLDOC01-appb-I000103
Figure JPOXMLDOC01-appb-I000104
Figure JPOXMLDOC01-appb-I000104
Figure JPOXMLDOC01-appb-I000105
Figure JPOXMLDOC01-appb-I000105
Figure JPOXMLDOC01-appb-I000106
Figure JPOXMLDOC01-appb-I000106
Figure JPOXMLDOC01-appb-I000107
Figure JPOXMLDOC01-appb-I000107
Figure JPOXMLDOC01-appb-I000108
Figure JPOXMLDOC01-appb-I000108
Figure JPOXMLDOC01-appb-I000109
Figure JPOXMLDOC01-appb-I000109
Figure JPOXMLDOC01-appb-I000110
Figure JPOXMLDOC01-appb-I000110
Figure JPOXMLDOC01-appb-I000111
Figure JPOXMLDOC01-appb-I000111
Figure JPOXMLDOC01-appb-I000112
Figure JPOXMLDOC01-appb-I000112
Figure JPOXMLDOC01-appb-I000113
Figure JPOXMLDOC01-appb-I000113
Figure JPOXMLDOC01-appb-I000114
Figure JPOXMLDOC01-appb-I000114
Figure JPOXMLDOC01-appb-I000115
Figure JPOXMLDOC01-appb-I000115
Figure JPOXMLDOC01-appb-I000116
Figure JPOXMLDOC01-appb-I000116
Figure JPOXMLDOC01-appb-I000117
Figure JPOXMLDOC01-appb-I000117
Figure JPOXMLDOC01-appb-I000118
Figure JPOXMLDOC01-appb-I000118
Figure JPOXMLDOC01-appb-I000119
Figure JPOXMLDOC01-appb-I000119
Figure JPOXMLDOC01-appb-I000120
Figure JPOXMLDOC01-appb-I000120
Figure JPOXMLDOC01-appb-I000121
Figure JPOXMLDOC01-appb-I000121
Figure JPOXMLDOC01-appb-I000122
Figure JPOXMLDOC01-appb-I000122
Figure JPOXMLDOC01-appb-I000123
Figure JPOXMLDOC01-appb-I000123
第２表
Figure JPOXMLDOC01-appb-C000124
 Table 2
Figure JPOXMLDOC01-appb-C000124
Figure JPOXMLDOC01-appb-C000125
Figure JPOXMLDOC01-appb-C000125
Figure JPOXMLDOC01-appb-C000126
Figure JPOXMLDOC01-appb-C000126
Figure JPOXMLDOC01-appb-C000127
Figure JPOXMLDOC01-appb-C000127
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-C000129
Figure JPOXMLDOC01-appb-C000129
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-C000131
Figure JPOXMLDOC01-appb-C000131
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-C000133
Figure JPOXMLDOC01-appb-C000133
Figure JPOXMLDOC01-appb-C000134
Figure JPOXMLDOC01-appb-C000134
Figure JPOXMLDOC01-appb-C000135
Figure JPOXMLDOC01-appb-C000135
Figure JPOXMLDOC01-appb-C000136
Figure JPOXMLDOC01-appb-C000136
Figure JPOXMLDOC01-appb-C000137
Figure JPOXMLDOC01-appb-C000137
Figure JPOXMLDOC01-appb-C000138
Figure JPOXMLDOC01-appb-C000138
Figure JPOXMLDOC01-appb-C000139
Figure JPOXMLDOC01-appb-C000139
Figure JPOXMLDOC01-appb-C000140
Figure JPOXMLDOC01-appb-C000140
Figure JPOXMLDOC01-appb-I000141
Figure JPOXMLDOC01-appb-I000141
Figure JPOXMLDOC01-appb-I000142
Figure JPOXMLDOC01-appb-I000142
Figure JPOXMLDOC01-appb-I000143
Figure JPOXMLDOC01-appb-I000143
Figure JPOXMLDOC01-appb-I000144
Figure JPOXMLDOC01-appb-I000144
Figure JPOXMLDOC01-appb-I000145
Figure JPOXMLDOC01-appb-I000145
Figure JPOXMLDOC01-appb-I000146
Figure JPOXMLDOC01-appb-I000146
Figure JPOXMLDOC01-appb-I000147
Figure JPOXMLDOC01-appb-I000147
Figure JPOXMLDOC01-appb-I000148
Figure JPOXMLDOC01-appb-I000148
Figure JPOXMLDOC01-appb-I000149
Figure JPOXMLDOC01-appb-I000149
Figure JPOXMLDOC01-appb-I000150
Figure JPOXMLDOC01-appb-I000150
Figure JPOXMLDOC01-appb-I000151
Figure JPOXMLDOC01-appb-I000151
Figure JPOXMLDOC01-appb-I000152
Figure JPOXMLDOC01-appb-I000152
Figure JPOXMLDOC01-appb-I000153
Figure JPOXMLDOC01-appb-I000153
Figure JPOXMLDOC01-appb-I000154
Figure JPOXMLDOC01-appb-I000154
Figure JPOXMLDOC01-appb-I000155
Figure JPOXMLDOC01-appb-I000155
Figure JPOXMLDOC01-appb-I000156
Figure JPOXMLDOC01-appb-I000156
Figure JPOXMLDOC01-appb-I000157
Figure JPOXMLDOC01-appb-I000157
第３表
Figure JPOXMLDOC01-appb-C000158
 Table 3
Figure JPOXMLDOC01-appb-C000158
Figure JPOXMLDOC01-appb-C000159
Figure JPOXMLDOC01-appb-C000159
Figure JPOXMLDOC01-appb-C000160
Figure JPOXMLDOC01-appb-C000160
Figure JPOXMLDOC01-appb-C000161
Figure JPOXMLDOC01-appb-C000161
Figure JPOXMLDOC01-appb-C000162
Figure JPOXMLDOC01-appb-C000162
Figure JPOXMLDOC01-appb-C000163
Figure JPOXMLDOC01-appb-C000163
Figure JPOXMLDOC01-appb-C000164
Figure JPOXMLDOC01-appb-C000164
Figure JPOXMLDOC01-appb-C000165
Figure JPOXMLDOC01-appb-C000165
Figure JPOXMLDOC01-appb-C000166
Figure JPOXMLDOC01-appb-C000166
Figure JPOXMLDOC01-appb-C000167
Figure JPOXMLDOC01-appb-C000167
Figure JPOXMLDOC01-appb-C000168
Figure JPOXMLDOC01-appb-C000168
Figure JPOXMLDOC01-appb-I000169
Figure JPOXMLDOC01-appb-I000169
Figure JPOXMLDOC01-appb-I000170
Figure JPOXMLDOC01-appb-I000170
Figure JPOXMLDOC01-appb-I000171
Figure JPOXMLDOC01-appb-I000171
Figure JPOXMLDOC01-appb-I000172
Figure JPOXMLDOC01-appb-I000172
Figure JPOXMLDOC01-appb-I000173
Figure JPOXMLDOC01-appb-I000173
Figure JPOXMLDOC01-appb-I000174
Figure JPOXMLDOC01-appb-I000174
Figure JPOXMLDOC01-appb-I000175
Figure JPOXMLDOC01-appb-I000175
Figure JPOXMLDOC01-appb-I000176
Figure JPOXMLDOC01-appb-I000176
Figure JPOXMLDOC01-appb-I000177
Figure JPOXMLDOC01-appb-I000177
Figure JPOXMLDOC01-appb-I000178
Figure JPOXMLDOC01-appb-I000178
Figure JPOXMLDOC01-appb-I000179
Figure JPOXMLDOC01-appb-I000179
Figure JPOXMLDOC01-appb-I000180
Figure JPOXMLDOC01-appb-I000180
Figure JPOXMLDOC01-appb-I000181
Figure JPOXMLDOC01-appb-I000181
Figure JPOXMLDOC01-appb-I000182
Figure JPOXMLDOC01-appb-I000182
Figure JPOXMLDOC01-appb-I000183
Figure JPOXMLDOC01-appb-I000183
Figure JPOXMLDOC01-appb-I000184
Figure JPOXMLDOC01-appb-I000184
第４表
Figure JPOXMLDOC01-appb-C000185
 Table 4
Figure JPOXMLDOC01-appb-C000185
Figure JPOXMLDOC01-appb-C000186
Figure JPOXMLDOC01-appb-C000186
Figure JPOXMLDOC01-appb-C000187
Figure JPOXMLDOC01-appb-C000187
Figure JPOXMLDOC01-appb-C000188
Figure JPOXMLDOC01-appb-C000188
Figure JPOXMLDOC01-appb-C000189
Figure JPOXMLDOC01-appb-C000189
Figure JPOXMLDOC01-appb-I000190
Figure JPOXMLDOC01-appb-I000190
Figure JPOXMLDOC01-appb-I000191
Figure JPOXMLDOC01-appb-I000191
Figure JPOXMLDOC01-appb-I000192
Figure JPOXMLDOC01-appb-I000192
Figure JPOXMLDOC01-appb-I000193
Figure JPOXMLDOC01-appb-I000193
Figure JPOXMLDOC01-appb-I000194
Figure JPOXMLDOC01-appb-I000194
Figure JPOXMLDOC01-appb-I000195
Figure JPOXMLDOC01-appb-I000195
Figure JPOXMLDOC01-appb-I000196
Figure JPOXMLDOC01-appb-I000196
Figure JPOXMLDOC01-appb-I000197
Figure JPOXMLDOC01-appb-I000197
Figure JPOXMLDOC01-appb-I000198
Figure JPOXMLDOC01-appb-I000198
Figure JPOXMLDOC01-appb-I000199
Figure JPOXMLDOC01-appb-I000199
　本発明化合物は、農園芸作物及び樹木等を加害する所謂農業害虫、家畜・家禽類に寄生する所謂家畜害虫、家屋等の人間の生活環境で様々な悪影響を与える所謂衛生害虫、倉庫に貯蔵された穀物等を加害する所謂貯穀害虫等としての昆虫類、及び同様の場面で発生、加害するダニ類、甲殻類、軟体動物、線虫類の何れの有害生物も低濃度で有効に防除できる。 The compounds of the present invention are stored in warehouses, so-called agricultural pests that harm agricultural and horticultural crops and trees, so-called livestock pests that parasitize livestock and poultry, so-called sanitary pests that cause various adverse effects in the human living environment such as houses. It is possible to effectively control insects such as so-called stored grain pests that harm cereals and the like, and pests such as mites, crustaceans, molluscs, and nematodes that occur and harm in similar situations at low concentrations.
　本発明化合物を用いて防除しうる昆虫類、ダニ類、甲殻類、軟体動物及び線虫類には具体的に、例えば、クリタマバチChestnut gall wasp（Dryocosmus kuriphilus）、アルゼンチンアリArgentine ant（Linepithema humile）、グンタイアリArmy ant（Eciton burchelli, E. schmitti）、クロオオアリJapanese carpenter ant（Camponotus japonicus）、イエヒメアリPharaoh ant（Monomorium pharaonis）、ブルドックアント類Bulldog ant（Myrmecia spp.）、ファイヤーアント類Fire ant（Solenopsis spp.）、オオスズメバチAsian giant hornet（Vespa mandarina）、キイロスズメバチJapanese yellow hornet（Vespa simillima）、チュウレンジハバチLarge rose sawfly（Arge pagana）、マツノキハバチEuropean pine sawfly（Neodiprion sertifer）、クリハバチChestnut sawfly（Apethymus kuri）、セグロカブラハバチCabbage sawfly（Athalia infumata）、カブラハバチTurnip sawfly（Athalia rosae）等の膜翅目（Hymenoptera）昆虫、
　ナシチビガPear leaf miner（Bucculatrix pyrivorella）、チャノホソガTea leafroller（Caloptilia theivora）、キンモンホソガApple leafminer（Phyllonorycter ringoniella）、ミカンハモグリガCitrus leafminer（Phyllocnistis citrella）、イモキバガSweetpotato leaffolder（Helcystogramma triannulella）、ワタアカミムシPink bollworm（Pectinophora gossypiella）、カキノヘタムシガPersimmon fruit moth（Stathmopoda masinissa）、モモシンクイガPeach fruit moth（Carposina sasakii）、ネギコガAllium leafminer（Acrolepiopsis sapporensis）、ヤマノイモコガYam leafminer（Acrolepiopsis suzukiella）、モモハモグリガPeach leafminer（Lyonetia clerkella）、ギンモンハモグリガ（Lyonetia prunifoliella malinella）、コナガDiamondback moth（Plutella xylostella）、ニカメイガRice stem borer（Chilo suppressalis）、シバツトガBluegrass webworm（Parapediasia teterrella）、ハイマダラノメイガCabbage webworm（Hellula undalis）、コブノメイガRice leafroller（Cnaphalocrocis medinalis）、モモノゴマダラノメイガYellow peach moth（Conogethes punctiferalis）、ワタヘリクロノメイガCucumber moth（Diaphania indica）、クワノメイガMulberry pyralid（Glyphodes pyloalis）、アワノメイガAsian corn borer（Ostrinia furnacalis）、ヨーロッパアワノメイガEuropean corn borer（Ostrinia nubilalis）、アズキノメイガAdzuki bean borer（Ostrinia scapulalis）、モロコシマダラメイガLesser corn stalk borer（Elasmopalpus lignosellus）、シロイチモジマダラメイガLimabean pod borer（Etiella zinckenella）、ピーチツリーボーラーPeach tree borer（Synanthedon exitiosa）、コスカシバCherry tree borer（Synanthedon hector）、クビアカスカシバ（Toleria romanovi）、イラガOriental moth（Monema flavescens）、アオイラガ（Parasa consocia）、ヒロヘリアオイラガ（Parasa lepida）、クロシタアオイラガ（Parasa siniea）、タケノホソクロバ（Artona martini）、リンゴハマキクロバ（Illiberis pruni）、ウメスカシクロバ（Illiberis rotundata）、ヒメボクトウCarpenter moth（Cossus insularis）、コドリンガCodling moth（Cydia pomonella）、スモモヒメシンクイPlum fruit moth（Grapholita dimorpha）、ナシヒメシンクイOriental fruit moth（Grapholita molesta）、マメシンクイガSoybean pod borer（Leguminivora glycinivorella）、マメヒメサヤムシガSoybean podworm（Matsumuraeses phaseoli）、グレープベリーモスGrape berry moth（Endopiza viteana）、チャノコカクモンハマキSmaller tea tortrix（Adoxophyes honmai）、リンゴコカクモンハマキSummer fruit tortrix（Adoxophyes orana fasciata）、リンゴモンハマキAsiatic leafroller（Archips breviplicanus）、ミダレカクモンハマキApple tortrix（Archips fuscocupreanus）、チャハマキOriental tea tortrix（Homona magnanima）、トビハマキDark fruit-tree tortrix（Pandemis heparana）、マツカレハPine moth（Dendrolimus spectabilis）、ツガカレハJananese hemlock caterpillar（Dendrolimus superans）、タケカレハJapanese bamboo lappet moth（Euthrix albomaculata）、ヨシカレハDrinker moth（Euthrix potatoria）、カレハガOriental lappet（Gastropacha orientalis）、クヌギカレハ（Kunugia undans）、ヤマダカレハ（Kunugia yamadai）、トマトホーンワームTomato hornworm（Manduca quinquemaculata）、タバコスズメガTobacco hornworm（Manduca sexta）、アメリカシロヒトリFall webworm moth（Hyphantria cunea）、クワゴマダラヒトリMulberry tiger moth（Lemyra imparilis）、ヤネホソバ（Eilema fuscodorsalis）、ツマキホソバ（Eilema laevis）、ドクガOriental tussock moth（Artaxa subflava）、キドクガ（Euproctis piperita）、チャドクガTea tussock moth（Euproctis pseudoconspersa）、モンシロドクガSwan moth（Sphrageidus similis）、マイマイガGypsy moth（Lymantria dispar）、ヒメシロモンドクガWhite-spotted tussock moth（Orgyia thyellina）、フタオビコヤガRice green caterpillar（Naranga aenescens）、アケビコノハ（Adris tyrannus）、ナカジロシタバSweet potato leaf worm（Aedia leucomelas）、ヨトウガCabbage armyworm（Mamestra brassicae）、アワヨトウOriental armyworm（Pseudaletia separata）、スジキリヨトウLawn grass cutworm（Spodoptera depravata）、サザンアーミーワームSouthern armyworm（Spodoptera eridania）、シロイチモジヨトウBeet armyworm（Spodoptera exigua）、フォールアーミーワームFall armyworm（Spodoptera frugiperda）、コットンリーフワームCotton leafworm（Spodoptera littoralis）、ハスモンヨトウCommon cutworm（Spodoptera litura）、オオタバコガCotton bollworm（Helicoverpa armigera）、タバコガOriental tobacco budworm（Helicoverpa assulta）、タバコバッドワームTobacco budworm（Heliothis virescens）、アメリカタバコガCorn earworm（Helicoverpa zea）、タマナヤガBlack cutworm（Agrotis ipsilon）、カブラヤガTurnip moth（Agrotis segetum）、タマナギンウワバAsiatic common looper（Autographa nigrisigna）、ミツモンキンウワバThreespotted plusia（Ctenoplusia agnata）、ソイビーンルーパーSoybean looper（Pseudoplusia includens）、イラクサギンウワバCabbage looper（Trichoplusia ni）、ヨモギエダシャクJapanese giant looper（Ascotis selenaria）、オオモンシロチョウLarge white（Pieris brassicae）、モンシロチョウCabbage white butterfly（Pieris rapae crucivora）、イチモンジセセリStraight swift（Parnara guttata）、コットンリーフワームcotton leafworm (Alabama argillacea)、サトウキビメイガsugarcane borer（Diatraea sacharalis）等の鱗翅目（Lepidoptera）昆虫、
　ウリミバエMelon fly（Bactrocera cucurbitae）、ミカンコミバエOriental fruit fly（Bactrocera dorsalis）、クイーンズランドミバエQueensland fruit fly（Bactrocera tryoni）、ミカンバエJapanese orange fly（Bactrocera tsuneonis）、チチュウカイミバエMediterranean fruit fly（Ceratitis capitata）、メキシコミバエMexican fruit fly（Anastrepha ludens）、リンゴミバエApple maggot（Rhagoletis pomonella）、イネハモグリバエRice leaf miner（Agromyza oryzae）、ナモグリバエPea leaf miner（Chromatomyia horticola）、アブラナハモグリバエCabbage leafminer（Liriomyza brassicae）、ナスハモグリバエTomato leaf miner（Liriomyza bryoniae）、ネギハモグリバエStone leek leafminer（Liriomyza chinensis）、アシグロハモグリバエPea leafminer（Liriomyza huidobrensis）、トマトハモグリバエTomato leafminer（Liriomyza sativae）、マメハモグリバエSerpentine leafminer（Liriomyza trifolii）、オウトウショウジョウバエJapanese fruit fly（Drosophila suzukii）、イネヒメハモグリバエSmaller rice leaf miner（Hydrellia griseola）、ツェツェバエTsetse fly（Glossina morsitans, G. palpalis）、ウマシラミバエForest fly（Hippobosca equina）、ヒツジシラミバエSheep ked（Melophagus ovinus）、タマネギバエOnion fly（Delia antiqua）、タネバエSeed corn maggot（Delia platura）、テンサイモグリハナバエBeet leaf miner（Pegomya cunicularia）、ヒメイエバエLesser house fly（Fannia canicularis）、シープヘッドフライSheep headfly（Hydrotaea irritans）、スウィートフライSweat fly（Morellia simplex）、フェイスフライFace fly（Musca autumnalis）、イエバエHousefly（Musca domestica）、オーストラリアブッシュフライAustralian bush fly（Musca vetustissima）、ノサシバエHorn fly（Haematobia irritans）、サシバエStable fly（Stomoxys calcitrans）、オオクロバエ（Calliphora lata）、ホホアカクロバエBottle fly（Calliphora vicina）、旧世界ラセンウジバエOld World screw-worm fly（Chrysomya bezziana）、ブロウフライBlow fly（Chrysomya chloropyga）、オビキンバエOriental latrine fly（Chrysomya megacephala）、アメリカオビキンバエNew World screw-worm fly（Cochliomyia hominivorax）、クロキンバエBlack blow fly（Phormia regina）、ルリキンバエNorthern blowfly（Protophormia terraenovae）、ヒツジキンバエAustralian sheep blowfly（Lucilia cuprina）、ミドリキンバエGreen bottle fly（Lucilia illustris）、ヒロズキンバエCommon green bottle fly（Lucilia sericata）、ボットフライBot flies（Cuterebra spp.）、ヒトヒフバエHuman botfly（Dermatobia hominis）、アトアカウマバエHorse nose bot fly（Gasterophilus haemorrhoidalis）、ウマバエHorse bot fly（Gasterophilus intestinalis）、アカウマバエThroat bot fly（Gasterophilus nasalis）、ウシヒフバエWarble fly（Hypoderma bovis）、キスジウシバエCommon cattle grub（Hypoderma lineatum）、ヒツジバエSheep nasal bot fly（Oestrus ovis）、フレッシュフライFlesh fly（Sarcophaga carnaria）、センチニクバエFlesh fly（Sarcophaga peregrina）、スプレイドディアーフライSplayed deerfly（Chrysops caecutiens）、メクラアブDeer fly（Chrysops suavis）、コモンホースフライCommon horse fly（Haematopota pluvialis）、グリーンヘッドホースフライGreenhead horse fly（Tabanus nigrovittatus）、ウシアブHorse fly（Tabanus trigonus）、ダイズサヤタマバエSoybean pod gall midge（Asphondylia yushimai）、ヘシアンバエHessian fly（Mayetiola destructor）、ムギアカタマバエOrange wheat blossom midge（Sitodiplosis mosellana）、ニワトリヌカカBiting midge（Culicoides arakawae）、トクナガクロヌカカBlack gnat（Leptoconops nipponensis）、キアシオオブユ（Prosimulium yezoensis）、ブラックフライBlack fly（Simulium ochraceum）、ガンビエハマダラカAfrican malaria mosquito（Anopheles gambiae）、シナハマダラカ（Anopheles hyrcanus sinesis）、オオツルハマダラカ（Anopheles lesteri）、ネッタイシマカYellow fever mosquito（Aedes aegypti）、ヒトスジシマカAsian tiger mosquito（Aedes albopictus）、チカイエカHouse mosquito（Culex pipiens molestus）、アカイエカHouse mosquito（Culex pipiens pallens）、コガタアカイエカ（Culex tritaeniorhynchus）、サシチョウバエSandfly（Phlebotomus spp.）、オオチョウバエMoth fly（Telmatoscopus albipunctatus）等の双翅目（Diptera）昆虫、
　ニワトリノミHen flea（Ceratophyllus gallinae)、スナノミChigoe flea（Tunga penetrans)、イヌノミDog flea（Ctenocephalides canis)、ネコノミCat flea（Ctenocephalides felis）、ニワトリフトノミSticktight flea（Echidnophaga gallinacea)、ヒトノミHuman flea（Pulex irritans）、ケオプスネズミノミOriental rat flea（Xenopsylla cheopis）等の隠翅目（Siphonaptera）昆虫、
　タバコシバンムシTobacco beetle（Lasioderma serricorne）、インゲンマメゾウムシCommon bean weevil（Acanthoscelides obtectus）、アズキゾウムシAdzuki bean beetle（Callosobruchus chinensis）、ブドウトラカミキリGrape borer（Xylotrechus pyrrhoderus）、ツヤハダゴマダラカミキリAsian long-horn beetle（Anoplophora glabripennis）、ゴマダラカミキリWhite-spotted longicorn beetle（Anoplophora malasiaca）、マツノマダラカミキリJapanese pine sawyer（Monochamus alternatus）、キボシカミキリYellow-spotted longicorn beetle（Psacothea hilaris）、コロラドハムシColorado potato beetle（Leptinotarsa decemlineata）、マスタードリーフビートルMustard leaf beetle（Phaedon cochleariae）、イネドロオイムシRice leaf beetle（Oulema oryzae）、マダラカサハラハムシReaf beetle（Demotina fasciculata）、ウリハムシCucurbit leaf beetle（Aulacophora femoralis）、テンサイトビハムシBeet flea beetle（Chaetocnema concinna）、ノーザンコーンルートワームNorthern corn rootworm（Diabrotica barberi）、ジュウイチホシウリハムシSouthern corn rootworm（Diabrotica undecimpunctata）、ウエスタンコーンルートワームWestern corn rootworm（Diabrotica virgifera）、キスジノミハムシStriped flea beetle（Phyllotreta striolata）、ナスナガスネトビハムシSolanum flea beetle（Psylliodes angusticollis）、インゲンテントウMexican been beetle（Epilachna varivestis）、オオニジュウヤホシテントウLarge twenty-eight-spotted ladybird（Epilachna vigintioctomaculata）、ニジュウヤホシテントウTwentyeight-spotted ladybird（Epilachna vigintioctopunctata）、ヒメヒラタケシキスイ（Epuraea domina）、ポーレンビートルPollen beetle（Meligethes aeneus）、モモチョッキリゾウムシPeach curculio（Rhynchites heros）、アリモドキゾウムシSweetpotato weevil（Cylas formicarius）、イモゾウムシWest Indian sweet potato weevil（Euscepes postfasciatus）、ワタミゾウムシBoll weevil（Anthonomus grandis）、シロヘリクチブトゾウムシWhite-fringed beetle（Graphognatus leucoloma）、キンケクチブトゾウムシBlack vine weevil（Otiorhynchus sulcatus）、アルファルファタコゾウムシAlfalfa weevil（Hypera postica）、グラナリアコクゾウGranary weevil（Sitophilus granarius）、コクゾウムシMaize weevil（Sitophilus zeamais）、シバオサゾウムシHunting billbug（Sphenophorus venatus vestitus）、イネゾウムシRice plant weevil（Echinocnemus squameus）、イネミズゾウムシRice water weevil（Lissohoptrus oryzophilus）、チャイロコメノゴミムシダマシYellow mealworm（Tenebrio molitor）、コクヌストモドキRed flour beetle（Tribolium castaneum）、マルクビクシコメツキSweetpotato wireworm（Melanotus fortnumi）、カンシャクシコメツキSugarcane wireworm（Melanotus tamsuyensis）、コアオハナムグリCitrus flower chafer（Gametis jucunda）、ナガチャコガネYellowish elongate chafer（Heptophylla picea）、ドウガネブイブイCupreous chafer（Anomala cuprea）、ヒメコガネSoybean beetle（Anomala rufocuprea）、マメコガネJapanese beetle（Popillia japonica）、アオバアリガタハネカクシRove beetle（Paederus fuscipes）等の鞘翅目（Coleoptera）昆虫、
　ミカンキジラミAsian citrus psyllid（Diaphorina citri）、ナシキジラミPear sucker（Psylla pyrisuga）、チャトゲコナジラミCamellia spiny whitefly（Aleurocanthus camelliae）、ミカントゲコナジラミOrange spiny whitefly（Aleurocanthus spiniferus）、シルバーリーフコナジラミSilverleaf whitefly（Bemisia argentifolii）、タバココナジラミSweetpotato whitefly（Bemisia tabaci）、ミカンコナジラミCitrus whitefly（Dialeurodes citri）、オンシツコナジラミGreenhouse whitefly（Trialeurodes vaporariorum）、エンドウヒゲナガアブラムシPea aphid（Acyrthosiphon pisum）、マメアブラムシCowpea aphid（Aphis craccivora）、マメクロアブラムシBlack bean aphid（Aphis fabae）、ダイズアブラムシSoybean aphid（Aphis glycines）、ワタアブラムシCotton aphid（Aphis gossypii）、リンゴアブラムシGreen apple aphid（Aphis pomi）、ユキヤナギアブラムシSpiraea aphid（Aphis spiraecola）、ジャガイモヒゲナガアブラムシFoxglove aphid（Aulacorthum solani）、ムギワラギクオマルアブラムシLeafcurl plum aphid（Brachycaudus helichrysi）、ダイコンアブラムシCabbage aphid（Brevicoryne brassicae）、ウォールナットアフィッドWalnut aphid（Chromaphis juglandicola）、ロシアンウィートアフィッドRussian wheat aphid（Diuraphis noxia）、オオバコアブラムシRosy apple aphid（Dysaphis plantaginea）、モモコフキアブラムシMealy plum aphid（Hyalopterus pruni）、ニセダイコンアブラムシTurnip aphid（Lipaphis erysimi）、チューリップヒゲナガアブラムシPotato aphid（Macrosiphum euphorbiae）、ブラックマージンドアフィッドBlackmargined aphid（Monellia caryella）、モモアカアブラムシGreen peach aphid（Myzus persicae）、レタスヒゲナガアブラムシLettuce aphid（Nasonovia ribisnigri）、ネギアブラムシOnion aphid（Neotoxoptera formosana）、ムギクビレアブラムシBird cherry-oat aphid（Rhopalosiphum padi）、オカボノアカアブラムシRice root aphid（Rhopalosiphum rufiabdominalis）、ムギヒゲナガアブラムシCorn leaf aphid（Sitobion akebiae）、イングリッシュグレインアフィッドEnglish grain aphid（Sitobion avenae）、ムギミドリアブラムシGreenbug（Schizaphis graminum）、コミカンアブラムシBlack citrus aphid（Toxoptera aurantii）、ミカンクロアブラムシBrown citrus aphid（Toxoptera citricida）、リンゴワタムシWooly apple aphid（Eriosoma lanigerum）、ブドウネアブラムシGrape phylloxera（Viteus vitifolii）、ツノロウムシIndian wax scale（Ceroplastes ceriferus）、ルビーロウムシRed wax scale（Ceroplastes rubens）、カンキツカタカイガラムシCitricola scale（Coccus pseudomagnoliarum）、アカマルカイガラムシCalifornia red scale（Aonidiella aurantii）、ナシマルカイガラムシSan jose scale（Comstockaspis perniciosa）、チャコノハカイガラムシTea scale（Fiorinia theae）、チャノマルカイガラムシPeony scale（Pseudaonidia paeoniae）、クワシロカイガラムシMulberry scale（Pseudaulacaspis pentagona）、ウメシロカイガラムシWhite peach scale（Pseudaulacaspis prunicola）、ニセヤノネカイガラムシCitrus snow scale（Unaspis citri）、マサキナガカイガラムシEuonymus scale（Unaspis euonymi）、ヤノネカイガラムシArrowhead scale（Unaspis yanonensis）、オオワラジカイガラムシGiant margarodid scale（Drosicha corpulenta）、イセリアカイガラムシCottony cushion scale（Icerya purchasi）、ナスコナカイガラムシCotton mealy bug（Phenacoccus solani）、ミカンコナカイガラムシCitrus mealybug（Planococcus citri）、フジコナカイガラムシJapanese mealybug（Planococcus kuraunhiae）、クワコナカイガラムシComstock mealybug（Pseudococcus comstocki）、グレープミールバグGrape mealybug（Pseudococcus maritimus）、ヒメトビウンカSmall brown planthopper（Laodelphax striatella）、トビイロウンカBrown rice planthopper（Nilaparvata lugens）、セジロウンカWhite-backed rice planthopper（Sogatella furcifera）、フタテンオオヨコバイGrape Leafhopper（Epiacanthus stramineus）、インディアンコットンリーフホッパーIndian cotton leafhopper（Amrasca devastans）、ミドリナガヨコバイBeardsley leafhopper（Balclutha saltuella）、フタテンヨコバイAster leafhopper（Macrosteles fascifrons）、ヒメフタテンヨコバイ（Macrosteles striifrons）、ツマグロヨコバイGreen rice leafhopper（Nephotettix cincticeps）、フタテンヒメヨコバイGrape Leafhopper（Arboridia apicalis）、ポテトリーフホッパーPotato Leafhopper（Empoasca fabae）、カキノヒメヨコバイ（Empoasca nipponica）、チャノミドリヒメヨコバイTea green leafhopper（Empoasca onukii）、マメノミドリヒメヨコバイBean's smaller green leafhopper（Empoasca sakaii）、ブチヒゲカメムシSloe bug（Dolycoris baccarum）、ナガメCabbage bug（Eurydema rugosa）、トゲシラホシカメムシWhitespotted spined bug（Eysarcoris aeneus）、オオトゲシラホシカメムシ（Eysarcoris lewisi）、シラホシカメムシWhite-spotted stink bug（Eysarcoris ventralis）、ツヤアオカメムシSheild bug（Glaucias subpunctatus）、クサギカメムシBrown marmorated stink bug（Halyomorpha halys）、アオクサカメムシEastern green stink bug（Nezara antennata）、ミナミアオカメムシSouthern green stink bug（Nezara viridula）、レッドバンディドスティンクバグRedbanded stink bug（Piezodorus guildinii）、イチモンジカメムシRedbanded shield bug（Piezodorus hybneri）、チャバネアオカメムシBrown-winged green bug（Plautia crossota）、イネクロカメムシJapanese black rice bug（Scotinophora lurida）、ホソヘリカメムシBean bug（Riptortus clavatus）、クモヘリカメムシRice bug（Leptocorisa chinensis）、ホソハリカメムシRice stink bug（Cletus punctiger）、ミナミトゲヘリカメムシSquash bug（Paradasynus spinosus）、アカヒメヘリカメムシRhopalid bug（Rhopalus maculatus）、アメリカコバネナガカメムシTrue chinch bug（Blissus leucopterus）、カンシャコバネナガカメムシOriental chinch bug（Cavelerius saccharivorus）、コバネヒョウタンナガカメムシSeed bug（Togo hemipterus）、アカホシカメムシRed cotton bug（Dysdercus cingulatus）、ベネズエラサシガメBlood-sucking bug（Rhodnius prolixus）、メキシコサシガメKissing bug（Triatoma dimidiata）、ブラジルサシガメKissing bug（Triatoma infestans）、グリーンスティンクバッグgreen stink bug (Acrosternum hilare)、ブロウンスティンクバッグbrown stink bug (Euschistus servus)、サウザングリーンスティンクバッグsouthern green stink bug (Nezara viridula)、ターニッシュプラントバッグTarnished plant bug (Lygus lineolaris)、スティンクバッグ（Dichelops furcatus）、シュガーカンスピットルバッグsugarcane spittlebug (Mahanarva fimbriolata)、ツツジグンバイAzalea lace bug（Stephanitis pyrioides）、トコジラミBed bug（Cimex lectularius）、ツマグロアオカスミカメPale greenplant bug（Apolygus spinolae）、ウェスタンターニッシュドプラントバグWestern tarnished plant bug（Lygus hesperus）、サビイロカスミカメTarnished plant bug（Lygus lineolaris）、ナガムギカスミカメRice stink bug（Stenodema sibiricum）、アカスジカスミカメSorghum plant bug（Stenotus rubrovittatus）、イネホソミドリカスミカメRice leaf bug（Trigonotylus caelestialium）、クロトビカスミカメIsland fleahopper（Halticus insularis）、ワタノミハムシCotton fleahopper（Pseudatomoscelis seriatus）等の半翅目（Hemiptera）昆虫
　ヒラズハナアザミウマFlower thrips（Frankliniella intonsa）、ミカンキイロアザミウマWestern flower thrips（Frankliniella occidentalis）、クロトンアザミウマGreenhouse thrips（Heliothrips haemorrhoidalis）、チャノキイロアザミウマYellow tea thrips（Scirtothrips dorsalis）、ミナミキイロアザミウマMelon thrips（Thrips palmi）、ネギアザミウマOnion thrips（Thrips tabaci）、カキクダアザミウマJapanese gall-forming thrips（Ponticulothrips diospyrosi）等の総翅目（Thysanoptera）昆虫、
　ニワトリツノハジラミBody louse（Menacanthus cornutus）、ウスイロニワトリハジラミSmall body louse（Menacanthus pallidulus）、ニワトリオオハジラミChicken body louse（Menacanthus stramineus）、ニワトリハジラミChicken shaft louse（Menopon gallinae）、ハバビロナガハジラミChicken head louse（Cuclotogaster heterographa）、カクアゴハジラミBrown chicken louse（Goniodes dissmilis）、ヒメニワトリハジラミFluff louse（Goniodes gallinae）、マルハジラミLarge hen louse（Goniodes gigas）、ニワトリナガハジラミWing louse（Lipeurus caponis）、ウシハジラミCattle chewing louse（Damalinia bovis）、ネコハジラミCat louse（Felicola subrostrata）、イヌハジラミDog biting louse（Trichodectes canis）、ウシジラミShort-nosed cattle louse（Haematopinus eurysternus）、ウシジラミTail switch louse（Haematopinus quadripertusus）、ブタジラミLarge pig louse（Haematopinus suis）、スイギュウジラミBuffalo louse（Haematopinus tuberculatus）、イヌジラミDog sucking louse（Linognathus setosus）、ウシホソジラミLong-nosed cattle louse（Linognathus vituri）、ラビットロウズRabbit louse（Haemodipsus ventricosus）、ケブカウシジラミLittle blue cattle louse（Solenopotes capillatus）、ヒトジラミHead louse（Pediculus humanus）、ハツカネズミジラミMouse louse（Polyplax serratus）、ケジラミCrab louse（Pthirus pubis）等の咀顎目（Psocodea）昆虫、
　サバクトビバッタDesert locust（Schistocerca gregaria）、オーストラリアトビバッタAustralian plague locust（Chortoicetes terminifera）、トノサマバッタMigratory locust（Locusta migratoria）、ハネナガイナゴLesser paddy grasshopper（Oxya japonica）、コバネイナゴRice grasshopper（Oxya yezoensis）、エンマコオロギEmma field cricket（Teleogryllus emma）、ケラOriental mole cricket（Gryllotalpa orientalis）等の直翅目（Orthoptera）昆虫、
　チャバネゴキブリGerman cockroach（Blattella germanica）、ワモンゴキブリAmerican cockroach（Periplaneta americana）、クロゴキブリSmoky-brown cockroach（Periplaneta fuliginosa）、ヤマトゴキブリJapanese cockroach（Periplaneta japonica）、ダイコクシロアリDaikoku dry-wood termite（Cryptotermes domesticus）、アメリカカンザイシロアリWestern dry-wood termite（Incisitermes minor）、イエシロアリFormosan subterranean termite（Coptotermes formosanus）、ヤマトシロアリJapanese subterranean termite（Reticulitermes speratus）、タイワンシロアリBlack-winged subterranean termite（Odontotermes formosanus）等の網翅目（Dictyoptera）昆虫、
　トゲナシシロトビムシRootfeeding springtail（Onychiurus folsomi）、シベリアシロトビムシ（Onychiurus sibiricus）、キボシマルトビムシGarden springtail（Bourletiella hortensis）等の粘管目（Collembola）六脚類、
　オカダンゴムシPill bug（Armadillidium vulgare）、ワラジムシCommon rough woodlouse（Porcellio scaber）等の等脚目（Isopoda）甲殻類、
　チョウモドキ（Argulus coregoni）、チョウJapanese fishlouse（Argulus japonicus）、ウミチョウ（Argulus scutiformis）等のチョウ目（Arguloida）甲殻類、
　ウオジラミSea louse（Caligus curtus, C. elongatus）、サーモンローズSalmon louse（Lepeophtheirus salmonis）等のシフォノストム目（Siphonostomatoida）甲殻類、
　サヤアシニクダニStorage mite（Glycyphagus destructor）、イエニクダニHouse itch mite（Glycyphagus domesticus）、ムギコナダニBrown-legged grain mite（Aleuroglyphus ovatus）、ケナガコナダニCheese mite（Tyrophagus putrescentiae）、ホウレンソウケナガコナダニ（Tyrophagus similis）、ロビンネダニBulb mite（Rhizoglyphus robini）、ヒシガタウモウダニFeather mite（Pterolichus obtusus）、ニワトリウモウダニFeather mite（Megninia cubitalis）、コナヒョウヒダニAmerican house dust mite（Dermatophagoides farinae）、ヤケヒョウヒダニHouse dust mite（Dermatophagoides pteronyssinus）、ウシショクヒヒゼンダニChorioptic mange mite（Chorioptes bovis）、イヌミミヒゼンダニDog ear mite（Otodectes cynotis）、ウシキュウセンヒゼンダニPsoroptic mite（Psoroptes communis）、ウサギキュウセンヒゼンダニRabbit ear mite（Psoroptes cuniculi）、ヒツジキュウセンヒゼンダニSheep scab mite（Psoroptes ovis）、センコウヒゼンダニItch mite（Sarcoptes scabiei）、ネコショウセンコウヒゼンダニCat mange mite（Notoedres cati）等のコナダニ亜目（Astigmata）ダニ類、
　イエササラダニ（Haplochthonius simplex）等のササラダニ亜目（Oribatida）ダニ類、
　ミナミツメダニ（Chelacaropsis moorei）、ネコツメダニ（Cheyletiella blakei）、ウサギツメダニRabbit fur mite（Cheyletiella parasitovorax）、イヌツメダニ（Cheyletiella yasguri）、ホソツメダニ（Cheyletus eruditus）、クワガタツメダニ（Cheyletus malaccensis）、イヌニキビダニDog follicle mite（Demodex canis）、ネコニキビダニCat follicle mite（Demodex cati）、ニキビダニFace mite（Demodex folliculorum）、チューリップサビダニWheat curl mite（Aceria tulipae）、ニセナシサビダニPear rust mite（Eriophyes chibaensis）、ピーチバドマイトPeach bud mite（Eriophyes insidiosus）、ペアリーフブリスターマイトPearleaf blister mite（Eriophyes pyri）、チャノナガサビダニTea rust mite（Acaphylla theavagrans）、トマトサビダニTomato russet mite（Aculops lycopersici）、ミカンサビダニPink citrus rust mite（Aculops pelekassi）、リンゴサビダニApple rust mite（Aculus schlechtendali）、シトラスラストマイトCitrus rust mite（Phyllocoptruta oleivora）、チャノホコリダニBroad mite（Polyphagotarsonemus latus）、シクラメンホコリダニCyclamen mite（Phytonemus pallidus）、スジブトホコリダニTarsonemid mite（Tarsonemus bilobatus）、イネハダニ（Oligonychus shinkajii）、ミカンハダニCitrus red mite（Panonychus citri）、クワオオハダニSpider mite（Panonychus mori）、リンゴハダニEuropean red mite（Panonychus ulmi）、カンザワハダニKanzawa spider mite（Tetranychus kanzawai）、ナミハダニTwo-spotted spider mite（Tetranychus urticae）、ハクサイダニ（Penthaleus erythrocephalus）、ムギダニWinter grain mite（Penthaleus major）、ナンヨウツツガムシ（Eutrombicula wichmanni）、ミヤガワタマツツガムシTrombiculid mite（Helenicula miyagawai）、アカツツガムシ（Leptotrombidium akamushi）、フトゲツツガムシ（Leptotrombidium pallida）、タテツツガムシTsutsugamushi mite（Leptotrombidium scutellare）等のケダニ亜目（Prostigmata）ダニ類、
　イングリッシュファウルティックEnglish fowl tick（Argas persicus）、カズキダニSoft tick（Ornithodoros moubata）、回帰熱ティックRelapsing fever tick（Ornithodoros turicata）、スピノウズイヤーティックSpinose ear tick（Otobius megnini）、ローン・スターマダニLone star tick（Amblyomma americanum）、メキシコ湾岸マダニGulf coast tick（Amblyomma maculatum）、ツリガネチマダニ（Haemaphysalis campanulata）、キチマダニ（Haemaphysalis flava）、フタトゲチマダニBush tick（Haemaphysalis longicornis）、オオトゲチマダニ（Haemaphysalis megaspinosa）、トルトイスティックTortoise tick（Hyalomma aegyptium）、メディトレニアンティックMediterranean tick（Hyalomma marginatum）、オウシマダニTropical cattle tick（Boophilus microplus）、タネガタマダニ（Ixodes nipponensis）、ヤマトマダニ（Ixodes ovatus）、西部クロアシダニWestern black-legged tick（Ixodes pacifcus）、シュルツェマダニTaiga tick（Ixodes persulcatus）、ヒツジダニCastor bean tick（Ixodes ricinus）、クロアシダニBlack-legged tick（Ixodes scapularis）、トロピカルホースティックTropical horse tick（Anocentor nitens）、ロッキー山脈森林マダニRocky Mountain wood tick（Dermacentor andersoni）、西海岸マダニPacific Coast tick（Dermacentor occidentalis）、アミメカクマダニOrnate cow tick（Dermacentor reticulatus）、アメリカンドッグティックAmerican dog tick（Dermacentor variabilis）、リピセントール属（Rhipicentor spp.）、アメリカンキャトルティックAmerican cattle tick（Rhipicephalus annulatus）、クリイロコイタマダニBrown dog tick（Rhipicephalus sanguineus）等のマダニ亜目（Metastigmata）ダニ類、
　ワクモRed mite（Dermanyssus gallinae）、イエダニTropical rat mite（Ornithonyssus bacoti）、トリサシダニNorthern fowl mite（Ornithonyssus sylviarum）、ハニービーマイトHoneybee mite（Varroa destructor）、ミツバチヘギイタダニVarroa mite（Varroa jacobsoni）等のトゲダニ亜目（Mesostigmata）ダニ類、
　スクミリンゴガイApple snail（Pomacea canaliculata）等の盤足目（Architaenioglossa）腹足類、
　アフリカマイマイGiant African snail（Achatina fulica）、チャコウラナメクジTerrestrial slug（Limax marginatus）、ナメクジSlug（Meghimatium bilineatum）、ウスカワマイマイKorean round snail（Acusta despecta sieboldiana）、ミスジマイマイLand snail（Euhadra peliomphala）等のマイマイ目（Stylommatophora）腹足類、
　腎虫Giant kidney worm（Dioctophyma renale）、有環毛細線虫Thread worms（Capillaria annulata）、捻転毛細線虫Cropworm（Capillaria contorta）、肝毛細線虫Capillary liver worm（Capillaria hepatica）、穿通毛細線虫（Capillaria perforans）、フィリピン毛細線虫（Capillaria philippinensis）、豚毛細線虫（Capillaria suis）、牛鞭虫Whipworm（Trichuris discolor）、羊鞭虫Whipworm（Trichuris ovis）、豚鞭虫Pig whipworm（Trichuris suis）、ヒト鞭虫Human whipworm（Trichuris trichiura）、犬鞭虫Dog whipworm（Trichuris vulpis）、旋毛虫Pork worm（Trichinella spiralis）等のエノプルス目（Enoplida）線虫、
　乳頭糞線虫Intestinal threadworm（Strongyloides papillosus）、猫糞線虫（Strongyloides planiceps）、豚糞線虫Pig threadworm（Strongyloides ransomi）、ヒト糞線虫Threadworm（Strongyloides stercoralis）、ミクロネマ属（Micronema spp.）等の桿線虫目（Rhabditida）線虫、
　ブラジル鉤虫Hookworm（Ancylostoma braziliense）、犬鉤虫Dog hookworm（Ancylostoma caninum）、ズビニ鉤虫Old World hookworm（Ancylostoma duodenale）、猫鉤虫Cat hookworm（Ancylostoma tubaeforme）、狭頭鉤虫The Northern hookworm of dogs（Uncinaria stenocephala）、牛鉤虫Cattle hookworm（Bunostomum phlebotomum）、羊鉤虫Small ruminant hookworm（Bunostomum trigonocephalum）、アメリカ鉤虫New World hookworm（Necator americanus）、シアトストーマム属（Cyathostomum spp.）、シリコシクラス属（Cylicocyclus spp.）、シリコドントフォラス属（Cylicodontophorus spp.）、シリコステファナス属（Cylicostephanus spp.）、ロバ円虫（Strongylus asini）、無歯円虫（Strongylus edentatus）、馬円虫Blood worm（Strongylus equinus）、普通円虫Blood worm（Strongylus vulgaris）、羊縮小線虫Large-mouthed bowel worm（Chabertia ovina）、インド腸結節虫Nodular worm（Oesophagostomum brevicaudatum）、コロンビア腸結節虫Nodule worm（Oesophagostomum columbianum）、豚腸結節虫Nodule worm（Oesophagostomum dentatum）、アメリカ腸結節虫Nodular worm（Oesophagostomum georgianum）、腸結節虫Nodular worm（Oesophagostomum maplestonei）、豚盲結虫Nodular worm（Oesophagostomum quadrispinulatum）、牛腸結節虫Nodular worm（Oesophagostomum radiatum）、山羊腸結節虫Nodular worm（Oesophagostomum venulosum）、スクリジャビン開嘴虫（Syngamus skrjabinomorpha）、鶏開嘴虫Gapeworm（Syngamus trachea）、豚腎虫Swine kidney worm（Stephanurus dentatus）、クーペリアCattle bankrupt worm（Cooperia oncophora）、紅色毛様線虫Red stomach worm（Hyostrongylus rubidus）、皺胃毛様線虫Stomach hair worm（Trichostrongylus axei）、蛇状毛様線虫（Trichostrongylus colubriformis）、東洋毛様線虫Oriental trichostrongylus（Trichostrongylus orientalis）、捻転胃虫Red stomach worm（Haemonchus contortus）、牛捻転胃虫Cattle stomach worm（Mecistocirrus digitatus）、オステルターグ胃虫Brown stomach worm（Ostertagia ostertagi）、糸状肺虫Common lungworm（Dictyocaulus filaria）、牛肺虫Bovine lungworm（Dictyocaulus viviparus）、細頸毛円虫Thin-necked intestinal worm（Nematodirus filicollis）、豚肺虫Swine lungworm（Metastrongylus elongatus）、犬肺虫Lungworm（Filaroides hirthi）、肺毛細線虫Lungworm（Crenosoma aerophila）、キツネ肺虫Fox lungworm（Crenosoma vulpis）、広東住血線虫Rat lung worm（Angiostrongylus cantonensis）、住血線虫French heartworm（Angiostrongylus vasorum）、プロトストロンギラス属（Protostrongylus spp.）等の円虫目（Strongylida）線虫、
　イネシンガレセンチュウRice white tip nematode（Aphelenchoides besseyi）、マツノザイセンチュウPine wood nematode（Bursaphelenchus xylophilus）等の葉線虫目（Aphelenchida）線虫、
　ジャガイモシストセンチュウPotato cyst nematode（Globodera rostochiensis）、ムギシストセンチュウCereal cyst nematode（Heterodera avenae）、ダイズシストセンチュウSoybean cyst nematode（Heterodera glycines）、アレナリアネコブセンチュウPeanut root-knot nematode（Meloidogyne arenaria）、キタネコブセンチュウNorthern root-knot nematode（Meloidogyne hapla）、サツマイモネコブセンチュウSouthern root-knot nematode（Meloidogyne incognita）、ジャワネコブセンチュウJavanese root-knot nematode（Meloidogyne javanica）、ミナミネグサレセンチュウCoffee root-lesion nematode（Pratylenchus coffeae）、チャネグサレセンチュウTea root-lesion nematode（Pratylenchus loosi）、キタネグサレセンチュウCobb's root-lesion nematode（Pratylenchus penetrans）、クルミネグサレセンチュウWalnut root-lesion nematode（Pratylenchus vulnus）等のハリセンチュウ目（Tylenchida）線虫、
　ヒト蟯虫Pinworm（Enterobius vermicularis）、馬蟯虫Equine pinworm（Oxyuris equi）、ウサギ蟯虫Rabbit pinworm（Passalurus ambiguus）等の蟯虫目（Oxyurida）線虫、
　豚回虫Pig roundworm（Ascaris suum）、馬回虫Horse roundworm（Parascaris equorum）、犬小回虫Dog roundworm（Toxascaris leonina）、犬回虫Dog intestinal roundworm（Toxocara canis）、猫回虫Feline roundworm（Toxocara cati）、牛回虫Large cattle roundworm（Toxocara vitulorum）、アニサキス属（Anisakis spp.）、シュードテラノーバ属（Pseudoterranova spp.）、鶏盲腸虫Caecal worm（Heterakis gallinarum）、鶏回虫Chicken roundworm（Ascaridia galli）等の回虫目（Ascaridida）線虫、
　メジナ虫Guinea worm（Dracunculus medinensis）、ドロレス顎口虫（Gnathostoma doloresi）、剛棘顎口虫（Gnathostoma hispidum）、日本顎口虫（Gnathostoma nipponicum）、有棘顎口虫Reddish‐coloured worm（Gnathostoma spinigerum）、犬胃虫Dog stomach worm（Physaloptera canis）、猫胃虫Cat stomach worm（Physaloptera felidis, P. praeputialis）、ラーラ胃虫Feline/canine stomach worm（Physaloptera rara）、東洋眼虫Eye worm（Thelazia callipaeda）、ロデシア眼虫Bovine eyeworm（Thelazia rhodesi）、大口馬胃虫Large mouth stomach worm（Draschia megastoma）、小口胃虫Equine stomach worm（Habronema microstoma）、ハエ胃虫Stomach worm（Habronema muscae）、美麗食道虫Gullet worm（Gongylonema pulchrum）、類円豚胃虫Thick stomach worm（Ascarops strongylina）、牛パラフィラリアParafilaria（Parafilaria bovicola）、多乳頭糸状虫（Parafilaria multipapillosa）、沖縄糸状虫（Stephanofilaria okinawaensis）、バンクロフト糸状虫Bancroft filaria（Wuchereria bancrofti）、マレー糸状虫（Brugia malayi）、頸部糸状虫Neck threadworm（Onchocerca cervicalis）、ギブソン糸状虫（Onchocerca gibsoni）、咽頭糸状虫Cattle filarial worm（Onchocerca gutturosa）、回旋糸状虫（Onchocerca volvulus）、指状糸状虫Bovine filarial worm（Setaria digitata）、馬糸状虫Peritoneal worm（Setaria equina）、唇乳頭糸状虫（Setaria labiatopapillosa）、マーシャル糸状虫（Setaria marshalli）、犬糸状虫Dog heartworm（Dirofilaria immitis）、ロア糸状虫African eye worm（Loa loa）等の旋尾線虫目（Spirurida）線虫、
　鎖状鉤頭虫（Moniliformis moniliformis）、大鉤頭虫Giant thorny-headed worm（Macracanthorhynchus hirudinaceus）等の鉤頭虫類、
　広節裂頭条虫Fish tapeworm（Diphyllobothrium latum）、日本海裂頭条虫（Diphyllobothrium nihonkaiense）、マンソン裂頭条虫Manson tapeworm（Spirometra erinaceieuropaei）、大複殖門条虫（Diplogonoporus grandis）等の擬葉目（Pseudophyllidea）条虫、
　有線条虫（Mesocestoides lineatus）、有輪条虫Chicken tapeworm（Raillietina cesticillus）、棘溝条虫Fowl tapeworm（Raillietina echinobothrida）、方形条虫Chicken tapeworm（Raillietina tetragona）、胞状条虫Canine tapeworm（Taenia hydatigena）、多頭条虫Canine tapeworm（Taenia multiceps）、羊条虫Sheep measles（Taenia ovis）、豆状条虫Dog tapeworm（Taenia pisiformis）、無鉤条虫Beef tapeworm（Taenia saginata）、連節条虫Tapeworm（Taenia serialis）、有鉤条虫Pork tapeworm（Taenia solium）、猫条虫Feline tapeworm（Taenia taeniaeformis）、単包条虫Hydatid tapeworm（Echinococcus granulosus）、多包条虫Small fox tapeworm（Echinococcus multilocularis）、ヤマネコ包条虫（Echinococcus oligarthrus）、フォーゲル包条虫（Echinococcus vogeli）、縮小条虫Rat tapeworm（Hymenolepis diminuta）、小型条虫Dwarf tapeworm（Hymenolepis nana）、瓜実条虫Double-pored dog tapeworm（Dipylidium caninum）、楔状条虫（Amoebotaenia sphenoides）、漏斗状条虫（Choanotaenia infundibulum）、ウズラ条虫（Metroliasthes coturnix）、大条虫Equine tapeworm（Anoplocephala magna）、葉状条虫Cecal tapeworm（Anoplocephala perfoliata）、乳頭条虫Dwarf equine tapeworm（Paranoplocephala mamillana）、ベネデン条虫Common tapeworm（Moniezia benedeni）、拡張条虫Sheep tapeworm（Moniezia expansa）、スティレシア属（Stilesia spp.）等の円葉目（Cyclophyllidea）条虫、
　壷型吸虫（Pharyngostomum cordatum）、ビルハルツ住血吸虫Blood fluke（Schistosoma haematobium）、日本住血吸虫Blood fluke（Schistosoma japonicum）、マンソン住血吸虫Blood fluke（Schistosoma mansoni）等の有壁吸虫目（Strigeidida）吸虫、
　移睾棘口吸虫（Echinostoma cinetorchis）、浅田棘口吸虫（Echinostoma hortense）、巨大肝蛭Giant liver fluke（Fasciola gigantica）、肝蛭Common liver fluke（Fasciola hepatica）、肥大吸虫（Fasciolopsis buski）、平腹双口吸虫（Homalogaster paloniae）等の棘口吸虫目（Echinostomida）吸虫、
　大陸槍型吸虫（Dicrocoelium chinensis）、槍型吸虫Lancet liver fluke（Dicrocoelium dendriticum）、アフリカ槍型吸虫African lancet fluke（Dicrocoelium hospes）、小型膵蛭（Eurytrema coelomaticum）、膵蛭Pancreatic fluke（Eurytrema pancreaticum）、宮崎肺吸虫（Paragonimus miyazakii）、大平肺吸虫（Paragonimus ohirai）、ウエステルマン肺吸虫Lung fluke（Paragonimus westermani）等の斜睾吸虫目（Plagiorchiida）吸虫、
　アンフィメルス属（Amphimerus spp.）、肝吸虫Chinese liver fluke（Clonorchis sinensis）、猫肝吸虫Cat liver fluke（Opisthorchis felineus）、タイ肝吸虫Southeast Aasian liver fluke（Opisthorchis viverrini）、シュードアンフィストーマム属（Pseudamphistomum spp.）、メトロキス属（Metorchis spp.）、パラメトロキス属（Parametorchis spp.）、異形吸虫Intestinal fluke（Heterophyes heterophyes）、横川吸虫（Metagonimus yokokawai）、前腸異形吸虫（Pygidiopsis summa）等の後睾吸虫目（Opisthorchiida）吸虫、
　赤痢アメーバ（Entamoeba histolytica, E. invadens）等のアメーバ類、
　フタゴバベシア（Babesia bigemina）、牛バベシア（Babesia bovis）、大形馬バベシア（Babesia caballi）、犬バベシア（Babesia canis）、猫バベシア（Babesia felis）、ギブソン犬バベシア（Babesia gibsoni）、大型ピロプラズマ（Babesia ovata）、サイタウクスゾーン・フェリス（Cytauxzoon felis）、熱帯ピロプラズマ病タイレリア（Theileria annulata）、仮性沿岸熱タイレリア（Theileria mutans）、小型ピロプラズマ（Theileria orientalis）、東沿岸熱タイレリア（Theileria parva）等のピロプラズマ目（Piroplasmida）胞子虫類、
　ヘモプロテウス・マンソニ（Haemoproteus mansoni）、鶏ロイコチトゾーン（Leucocytozoon caulleryi）、熱帯熱マラリア原虫（Plasmodium falciparum）、四日熱マラリア原虫（Plasmodium malariae）、卵形マラリア原虫（Plasmodium ovale）、三日熱マラリア原虫（Plasmodium vivax）等の住血胞子虫目（Haemosporida）胞子虫類、
　カリオスポラ属（Caryospora spp.）、エイメリア・アセルブリナ（Eimeria acervulina）、エイメリア・ボビス（Eimeria bovis）、エイメリア・ブルネッチ（Eimeria brunetti）、エイメリア・マクシマ（Eimeria maxima）、エイメリア・ネカトリクス（Eimeria necatrix）、エイメリア・オビノイダリス（Eimeria ovinoidalis）、ウサギ肝コクシジウム（Eimeria stiedae）、鶏盲腸コクシジウム（Eimeria tenella）、犬イソスポーラ（Isospora canis）、猫イソスポーラ（Isospora felis）、豚イソスポーラ（Isospora suis）、ティゼリア・アレニ（Tyzzeria alleni）、ティゼリア・アンセリス（Tyzzeria anseris）、ティゼリア・パーニシオサ（Tyzzeria perniciosa）、ウェニョネラ・アナティス（Wenyonella anatis）、ウェニョネラ・ガガリ（Wenyonella gagari）、犬クリプトスポリジウム（Cryptosporidium canis）、猫クリプトスポリジウム（Cryptosporidium felis）、ヒトクリプトスポリジウム（Cryptosporidium hominis）、シチメンチョウクリプトスポリジウム（Cryptosporidium meleagridis）、ネズミクリプトスポリジウム（Cryptosporidium muris）、小形クリプトスポリジウム（Cryptosporidium parvum）、サルコシスチス・カニス（Sarcocystis canis）、クルーズ肉胞子虫（Sarcocystis cruzi）、サルコシスチス・フェリス（Sarcocystis felis）、ヒト肉胞子虫（Sarcocystis hominis）、サルコシスチス・ミーシェリアナ（Sarcocystis miescheriana）、サルコシスチス・ニューロナ（Sarcocystis neurona）、サルコシスチス・テネラ（Sarcocystis tenella）、サルコシスチス・オバリス（Sarcocystis ovalis）、トキソプラズマ（Toxoplasma gondii）、犬ヘパトゾーン（Hepatozoon canis）、猫ヘパトゾーン（Hepatozoon felis）等の真コクシジウム目（Eucoccidiorida）胞子虫類、
　大腸バランチジウム（Balantidium coli）等の前庭目（Vestibuliferida）繊毛虫類、
　ヒストモナス（Histomanas meleagridis）、腸トリコモナス（Pentatrichomonas hominis）、口腔トリコモナス（Trichomonas tenax）等のトリコモナス目（Trichomonadida）鞭毛虫類、
　ランブル鞭毛虫（Giardia intestinalis）、ジアルディア・ムリス（Giardia muris）、シチメンチョウヘキサミタ（Hexamita meleagridis）、ヘキサミタ・パルバ（Hexamita parva）等のディプロモナス目（Diplomonadida）鞭毛虫類、
　ドノバンリーシュマニア（Leishmania donovani）、幼児リーシュマニア（Leishmania infantum）、大形リーシュマニア（Leishmania major）、熱帯リーシュマニア（Leishmania tropica）、ガンビアトリパノソーマ（Trypanosoma brucei gambiense）、ローデシアトリパノソーマ（Trypanosoma brucei rhodesiense）、クルーズトリパノソーマ（Trypanosoma cruzi）、媾疫トリパノソーマ（Trypanosoma equiperdum）、エバンストリパノソーマ（Trypanosoma evansi）等のキネトプラスト目（Kinetoplastida）鞭毛虫類等が挙げられるが、本発明化合物を用いて防除しうる農園芸分野の有害生物、及び家畜、家禽、愛玩動物等の外部又は内部寄生虫はこれらのみに限定されるものではない。 Specific examples of insects, mites, crustaceans, mollusks and nematodes that can be controlled using the compounds of the present invention include, for example, the wasp chestnut gall wasp (Dryocosmus kuriphilus), the Argentine ant Argentine ant (Linepithema humile), Gunmy ant Army ant (Eciton burchelli, E. schmitti), Japanese carpenter ant (Camponotus japonicus), Green ant Pharaoh ant (Monomorium pharaonis), Bulldog ant class Bulldog ant (Myrmecia spp.), Fire ant class fire spant (Soop) , Asian giant hornet (Vespa mandarina), Japanese yellow hornet (Vespa simillima), large bee Large rose sawfly (Arge pagana), pine bee European pine sawfly (Neodiprion sertifer), bb sawfly (Athalia infumata), turnip sawnip (Turnip sawfly) Hymenoptera insects such as Athalia rosae)
Pear leaf miner (Bucculatrix pyrivorella), tea leaf roller (Caloptilia theivora), golden leaf soy Apple leafminer (Phyllonorycter ringoniella), citrus leafminer (Phyllocnistis citrella), immobilized leaflet Persimmon fruit moth (Stathmopoda masinissa), Peach fruit moth (Carposina sasakii), Allium leafminer (Acrolepiopsis sapporensis), Yami leafminer (Acrolepiopsis suzukiella), Peach fruit moth (Pel fruit) ), Diamondback moth (Plutella xylostella), red stem borer (Chilo suppressalis), Shibatatsuga Bluegrass webworm (Parapediasia teterrella) Cabbage webworm (Hellula undalis), Rice leaf roller (Cnaphalocrocis medinalis), Yellow moth moth (Conogethes punctiferalis), Cotton moth (Diaphania indica), Mulberry pyras (Mulberry pyras) Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Azuki bean borer (Ostrinia scapulalis), Sorghum moth Lesser corn stalk borer (Elasmopalpus lignosellus), ella borer L Tree borer Peach tree borer (Synanthedon exitiosa), Cosca Shiba Cherry tree borer (Synanthedon hector), Kubiakasukashiba (Toleria romanovi), Iraga Oriental moth (Monema flavescens), Aura Iga (Parasa consocia), Hiloheira Oiraga (Parasa) lepida), Parasa siniea, Parana siniea, Artona martini, Illiberis pruni, Illiberis rotundata, Carpenter moth (Cossus insularis), Codlingmon lum, Cydia Fruit moth (Grapholita dimorpha), Oriental fruit moth (Grapholita molesta), Bean pod borer (Leguminivora glycinivorella), Bean podworm (Matsumuraeses phaseoli), Grapeberry moss (Grape berryite moth) Smaller tea tortrix (Adoxophyes honmai), Apple coconut oyster Summer fruit tortrix (Adoxophyes orana fasciata), Apple peach oyster Asiatic leafroller (Archips breviplicanus), Midareka kumamaki Apple tortrix (Archips fuscocupreanus) Oriental tea tortrix (Homona magnanima), Tobihamaki Dark fruit-tree tortrix (Pandemis heparana), Matsukareha Pine moth (Dendrolimus spectabilis), Tsukakareha Jananese hemlock caterpillar (Dendrolimus superans), Takekareha, Japanese bamboo thrix ha Euthrix potatoria, Oriental lappet (Gastropacha orientalis), Kunugia undans, Kunugia yamadai, Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Alliga moth) cunea), Mulberry tiger moth (Lemyra imparilis), white flies (Eilema fuscodorsalis), black buckwheat (Eilema laevis), white moths udoconspersa), Swan moth (Sphrageidus similis), Gypsy moth (Lymantria dispar), White-spotted tussock moth (Orgyia thyellina), Rice green caterpillar (Naranga aenescens), Naranga aenescens leaf worm (Aedia leucomelas), mushroom Cabbage armyworm (Mamestra brassicae), Ayayoto Oriental armyworm (Pseudaletia separata), Japanese swordfish Lawn grass cutworm (Spodoptera depravata), Southern army worm Southern armyworm (ex armed worm) Fall army worm Fall armyworm (Spodoptera frugiperda), cotton leaf worm Cotton leafworm (Spodoptera littoralis), common cutworm (Spodoptera litura), giant bollworm (Helicoverpa armigera), tobacco moth Orienta l tobacco budworm (Helicoverpa assulta), tobacco bad worm Tobacco budworm (Heliothis virescens), American tobacco moth Corn earworm (Helicoverpa zea), Japanese red moth Black cutworm (Agrotis ipsilon), Kaburaya moth Turnip moth (Agrotis segetum) ), Honey beetle Threespotted plusia (Ctenoplusia agnata), soy bean looper, soybean looper (Pseudoplusia includens), nettle cabbage cabbage looper (Trichoplusia ni), mugwort Japanese giant looper (Ascotis selenaria), brass white white butterfly Lis , Lepidoptera (Lepidoptera) such as Cabbage white butterfly (Pieris rapae crucivora), Ichimongiseri Straight swift (Parnara guttata), cotton leaf worm cotton leafworm (Alabama argillacea), sugarcane borer (Diatraea sacharalis) Insect,
The fruit fly Melon fly (Bactrocera cucurbitae), the fruit fly Oriental fruit fly (Bactrocera dorsalis), the Queensland fruit fly Queensland fruit fly (Bactrocera tryoni), the fruit fly Japanese orange fly (Bactrocera tsuneonis), the Mediterranean fruit fly Mediterraneitis fly (Anastrepha ludens), ring-fly fly Apple maggot (Rhagoletis pomonella), rice leaf fly Rice leaf miner (Agromyza oryzae), leaf flyer Pea leaf miner (Chromatomyia horticola), oil leaf fly Cabbage leafminer (Liriomyza brassicae) ), Green leaf fly Stone leek leafminer (Liriomyza chinensis), green leaf fly Pea leafminer (Liriomyza huidobrensis), tomato leaf fly Tomato leafminer (Liriomyza sativae), bean leaf fly Serpentine leafminer (Liriom yza trifolii), Japanese fruit fly (Drosophila suzukii), Small leaf rice leaf miner (Hydrellia griseola), Tsetse fly (Glossina morsitans, G. palpalis), White fly, Forest fly (Hippobca) Melophagus ovinus), Onion fly (Delia antiqua), Seed corn maggot (Delia platura), sugar beet fly, Beet leaf miner (Pegomya cunicularia), Lesser house fly (Fannia canicularis), Sheep head fly (Hritae flyfly) ), Sweet fly (Morellia simplex), Face fly (Musca autumnalis), Housefly (Musca domestica), Australian bush fly (Musca vetustissima), Horn flies Horn fly (Haematobia irritans), Stable fly (Stable fly) Stomoxys calci trans, Calliphora lata, Bottle fly (Calliphora vicina), Old world screw-worm fly (Chrysomya bezziana), Blow fly (Chrysomya chloropyga), Oriental latrine fly (Chrysomya, Chrysomya America) New World screw-worm fly (Cochliomyia hominivorax), Black blow fly (Phormia regina), Northern blowfly (Protophormia terraenovae), sheep fly, Australian sheep blowfly (Lucilia cuprina), Green bottle fly (Lucilia illustris) Common green bottle fly (Lucilia sericata), Bot flies (Cuterebra spp.), Human fly botfly (Dermatobia hominis), Horse-nosed bot fly (Gasterophilus haemorrhoidalis), Horse-fly Horis bottest t fly (Gasterophilus nasalis), Bullflies Warble fly (Hypoderma bovis), Common cattle grub (Hypoderma lineatum), Sheep nasal bot fly (Oestrus ovis), Fresh fly Flesh fly (Sarcophaga carnaria), perch Srina ), Splayed deerfly (Chrysops caecutiens), Mekurabu Deer fly (Chrysops suavis), Common horse fly (Haematopota pluvialis), Greenhead horsefly (Greenhead horse fly (Tabanus nigrovittatus)) ), Soybean pod gall midge (Asphondylia yushimai), Hessian fly Hessian fly (Mayetiola destructor), mud wings Orange wheat blossom midge (Sitodiplosis mosellana), chick nuka Biting midge (Culicoides arakawae), L nipponens is), Black-tailed Blackfish (Prosimulium yezoensis), Black fly (Simulium ochraceum), African Malaria mosquito (Anopheles gambiae), Red-backed Shrimp (Anopheles hyrcanus sinesis), Anophelestosi aegypti), Asian tiger mosquito (Aedes albopictus), Chikaeka House mosquito (Culex pipiens molestus), Akaieka House mosquito (Culex pipiens pallens), Culex tritaeniorhynchus, moth P Diptera insects such as Telmatoscopus albipunctatus)
Chicken flea Hen flea (Ceratophyllus gallinae), Japanese flea Chigoe flea (Tunga penetrans), Dog flea Dog flea (Ctenocephalides canis), Cat flea Cat flea (Ctenocephalides felis), Chicken flea Sticktight flea (Echidnopha human ritual) , Siphonaptera insects such as Oriental rat flea (Xenopsylla cheopis),
Tobacco beetle (Lasioderma serricorne), Common bean weevil (Acanthoscelides obtectus), Adzuki bean beetle (Callosobruchus chinensis), Grape borer (Xylotrechus pyrrhoder beetle beetle) White-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine sawyer (Monochamus alternatus), Yellow-spotted longicorn beetle (Psacothea hilaris), Colorado potato beetle Colorado beetle beetle (Phaedon cochleariae), rice leaf beetle Rice leaf beetle (Oulema oryzae), spotted leaf beetle (Demotina fasciculata), leaf beetle Cucurbit leaf beetle (Aulacophora femoralis) Beet flea beetle (Chaetocnema concinna), Northern corn rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm Western corn rootworm (Diabrotica virgifera), Triped P flea beetle striolata), Solanum flea beetle (Psylliodes angusticollis), green beetle Mexican been beetle (Epilachna varivestis), large twenty-eight-spotted ladybird (Epilachna vigintioctomawata bird), (Epilachna vigintioctopunctata), Epuraea domina, Pollen beetle (Meligethes aeneus), Peach curculio (Rhynchites heros), Sweetpotato weevil (Cylas formicarius), potato weevil West Indian sweet potato weevil (Euscepes postfasciatus), cotton weevil Boll weevil (Anthonomus grandis), white-flying beetle White-fringed beetle (Graphognatus leucoloma), horned weevil weevil Octopus weevil Alfalfa weevil (Hypera postica), Granary weevil (Sitophilus granarius), Chinese weevil Maize weevil (Sitophilus zeamais), Shibao weevil Hunting billbug (Sphenophorus venatus vestitus), Ezo weevil weevil (Lissohoptrus oryzophilus), yellow mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum), sweet potato wireworm (Melanotus fortnumi), citrus fruit Tsuruga Sugarcane wireworm (Melanotus tamsuyensis), Coreus crested citrus flower chafer (Gametis jucunda), Nagachakogane, Yellowish elongate chafer (Heptophylla picea), Douganebuibu Cupreous chafer (Anomala cuprea), Japanese beetle ), Coleoptera insects such as Rove beetle (Paederus fuscipes),
Asian citrus psyllid (Diaphorina citri), pear sucker Pear sucker (Psylla pyrisuga), Chatel spiny whitefly (Aleurocanthus camelliae), orange spiny whitefly (Aleurocanthus spiniferus), white leaffly (Aleurocanthus spiniferus) Whitefly Sweetpotato whitefly (Bemisia tabaci), Citrus whitefly (Dialeurodes citri), Greenhouse whitefly (Trialeurodes vaporariorum), Pea aphid (Acyrthosiphon pisum), Bean accura bee crab aphid (Aphis fabae), Soybean Aphid (Aphis glycines), Cotton Aphid (Aphis gossypii), Apple Aphid (Aphis pomi), Spiraea aphid (Aphis pomi) Aphis spiraecola), Foxglove aphid (Aulacorthum solani), Leaf curl plum aphid (Brachycaudus helichrysi), Japanese aphid Cabbage aphid (Brevicoryne brassiae), Walnut aphid Wola Russian wheat aphid (Diuraphis noxia), plantain beetle Rosy apple aphid (Dysaphis plantaginea), peach beetle Mealy plum aphid (Hyalopterus pruni), black pea aphid Turnip aphid (Lipaphis erysimi), tulip beetle aphid Margin door aphid (Monellia caryella), peach aphid Green peach aphid (Myzus persicae), Lettuce aphid (Nasonovia ribisnigri), Nephia Onion aphid (N eotoxoptera formosana), wheat cherry-oat aphid (Rhopalosiphum padi), rice aphid Rice root aphid (Rhopalosiphum rufiabdominalis), wheat leaf aphid (Sitobion akebiae), English grain aito avenae), Greenbug (Schizaphis graminum), Black citrus aphid (Toxoptera aurantii), Brown citrus aphid (Toxoptera citricida), Apple weevil Wooly apple aphid (Eriosoma lanigerum), Grape aphid Viteus vitifolii), hornet beetle Indian wax scale (Ceroplastes ceriferus), ruby weevil Red wax scale (Ceroplastes rubens), citrus scale insect (Coccus pseudomagnoliarum), red beetle California red scale (Aonidiella aurantii), pear Scale scale San jose scale (Comstockaspis perniciosa), scale scale tea scale (Teori scale), scale scale scale Peony scale (Pseudaonidia paeoniae), scale beetle scale Mulberry scale (Pseudaulacaspis pentagona), white scale scale Pula scale pi Citrus snow scale (Unaspis citri), Euonymus scale (Unaspis euonymi), Agarhead scale (Unaspis yanonensis), Giant margarodid scale (Drosicha corottenta scale) purchasi), worm beetle Cotton mealy bug (Phenacoccus solani), citrus mealybug (Citrus mealybug (Planococcus citri)), Japanese mealybug (Planococcus kuraunhiae), stag beetle Comstock me alybug (Pseudococcus comstocki), grape mealybug (Pseudococcus maritimus), brown brown planthopper (Laodelphax striatella), brown rice planthopper (Nilaparvata lugens), white-backedella planta (Gifer) Leafhopper (Epiacanthus stramineus), Indian cotton leafhopper (Amrasca devastans), Greens leafhopper (Bardsley leafhopper (Balclutha saltuella)), Aster leafhopper (Macrosteles fascifrons), Green leafy leafhopper (Macrosteles striifrons) leafhopper (Nephotettix cincticeps), Grape Leafhopper (Arboridia apicalis), Potato Leafhopper (Empoasca fabae), Emporasca nipponica, Chanomi Green leafhopper (Empoasca onukii), Bean's smaller green leafhopper (Empoasca sakaii), Sleek bug (Dolycoris baccarum), Sea turtle Cabbage bug (Eurydema rugosa), Spined whitespot ), White-spotted stink bug (Eysarcoris lewisi), white-spotted stink bug (Eysarcoris ventralis), blue-headed stink bug Sheild bug (Glaucias subpunctatus), brown marmorink stink bug (Halyomorpha haly) Nezara antennata), Southern green stink bug (Nezara viridula), Redbanded stink bug (Piezodorus guildinii), Redbanded shield bug (Piezodorus hybneri), Brown-winged crossota (Brown-winged cross bug) Japanese black rice bug (Scotinophora lurida), Bean bug (Riptortus clavatus), Spider helicopter Rice bug (Leptocorisa chinensis), Japanese stink bug Rice stink bug (Cletus punctiger), Southern bug shrimp bug (Paradasynus spinosus), Red-backed Helicopod Bug Rhopalid bug (Rhopalus maculatus), American Red-footed Beetle True chinch bug (Blissus leucopterus), Japanese Red-headed Bug, Oriental chinch bug (Cavelerius saccharivorus) Red cotton bug (Dysdercus cingulatus), Venezuelan sand turtle Blood-sucking bug (Rhodnius prolixus), Mexican sand turtle Kissing bug (Triatoma dimidiata), Brazilian sand turtle Kissing bug (Triatoma infestans), green stink bug sternumhil Aster ), Blown Stink bag brown stink bug (Euschistus servus), Southern green stink bag (Nezara viridula), Tarnished plant bug (Lygus lineolaris), Stink bag (Dichelops furcatus), Sugarcans pitle bag sugarcane spittlebug (Mahanarva fimbriolata), azalea lace bug (Stephanitis pyrioides), bed bug Bed bug (Cimex lectularius), bluefin turtle Pale greenplant bug (Apolygus spinolae), western tarnished plant bug (Lygus hesperus) Tarnished plant bug (Lygus lineolaris), Nagamushikasikameka Rice stink bug (Stenodema sibiricum), Akasujikasikameka Sorghum plant bug (Stenotus rubrovittatus), Rice fossil turtle Rice leaf bug (Trigonotylus caelestlium) Hemiptera insects such as and fleahopper (Halticus insularis), Cotton flea hopper Cotton fleahopper (Pseudatomoscelis seriatus)
Yellow thrips (Frankliniella intonsa), Western flower thrips (Frankliniella occidentalis), Greenhouse thrips (Heliothrips haemorrhoidalis), Yellow thrips Thysanoptera insects such as Thrips onion thrips (Thrips tabaci), Japanese gall-forming thrips (Ponticulothrips diospyrosi),
Chick shaft louse (Menopon hallid) (Cuclotogaster heterographa), brown fin louse (Goniodes dissmilis), bluefin louse Fluff louse (Goniodes gallinae), large bald larvae Large hen louse (Goniodes gigas), chicken swallow louse (Duru) ), Cat louse Cat louse (Felicola subrostrata), dog lice Dog biting louse (Trichodectes canis), cattle lice Short-nosed cattle louse (Haematopinus eurysternus), cattle lice Tail switch louse (Haematopinus quadripertusus), pig louse L inus suis), buffalo louse (Haematopinus tuberculatus), dog lice Dog sucking louse (Linognathus setosus), bovine white lice Long-nosed cattle louse (Linognathus cattle louse (Haemodipsus ventricosus ), Human louse Head louse (Pediculus humanus), mouse louse Mouse louse (Polyplax serratus), pheasant Crab louse (Pthirus pubis), etc.
Desert locust (Schistocerca gregaria), Australian platypus locust Australian plague locust (Chortoicetes terminifera), locust grasshopper Migratory locust (Locusta migratoria), red-eye locust Lesser paddy grasshopper (Oxya japonica), red-eye grass oxen (Teleogryllus emma), Kela Oriental mole cricket (Gryllotalpa orientalis), etc., Orthoptera insects,
German cockroach (Blattella germanica), American cockroach (Periplaneta americana), Black cockroach Smoky-brown cockroach (Periplaneta jafonica), Japanese cockroach (Periplaneta japonica), Daikokuus tomato (America) Termite Western dry-wood termite (Incisitermes minor), Common termite Formosan subterranean termite (Coptotermes formosanus), Japanese termite Japanese subterranean termite (Reticulitermes speratus), Thai termite Black-winged subterranean termite (Odontotermes formosanus) ,
Rootfeeding springtail (Onychiurus folsomi), Siberian white beetle (Onychiurus sibiricus), Garb spring spring (Bourletiella hortensis), etc.
Isopoda crustaceans such as Pill bug (Armadillidium vulgare), common rough woodlouse (Porcellio scaber),
Butterflyfish (Arguloida) crustaceans such as butterfly (Argulus coregoni), butterfly Japanese fishlouse (Argulus japonicus), sea butterfly (Argulus scutiformis)
Sea louse (Caligus curtus, C. elongatus), Salmon rose Salmon louse (Lepeophtheirus salmonis) and other crustaceans (Siphonostomatoida) crustaceans,
Sayaashi mite Storage mite (Glycyphagus destructor), house ticks mite (Glycyphagus domesticus), wheat mite Brown-legged grain mite (Aleuroglyphus ovatus), black mite Cheese mite (Tyrophagus putrescentiae), spiny mite Tyrophas , Hyugata mite Feather mite (Pterolichus obtusus), chick mite Feather mite (Megninia cubitalis), white house mite American house dust mite (Dermatophagoides farinae), yellow leopard mite bovis), Dog ear mite (Otodectes cynotis), Cattle cypress mite Psoroptic mite (Psoroptes communis), Rabbit ear mite Rabbit ear mite (Psoroptes cuniculi), Sheep cucumber Nhizendani Sheep scab mite (Psoroptes ovis), SENKOU mites Itch mite (Sarcoptes scabiei), cat foraminous mites Cat mange mite (Notoedres cati) mites suborder such as (Astigmata) mites,
Orabatida mites, such as the house salad ni (Haplochthonius simplex)
Sperm tick (Chelacaropsis moorei), cat tick (Cheyletiella blakei), rabbit tick Rabbit fur mite (Cheyletiella parasitovorax), crested tick (Cheyletiella yasguri), crested tick (Cheyletus eruditus), tick mite (Cheyletus eruditus) ), Caterpillar mites Cat follicle mite (Demodex cati), Acne mites Face mite (Demodex folliculorum), Tulip rust mites Wheat curl mite (Aceria tulipae), Black rust mites Pear rust mite (Eriophyes chibaensis), Peach bud insi ), Pearleaf blister mite (Eriophyes pyri), tea rust mite Tea rust mite (Acaphylla theavagrans), tomato rust mite Tomato russet mite (Aculops lycopersici), citrus mite Pink citrus rust mite (Aculops pelekassi) e rust mite (Aculus schlechtendali), Citrus rust mite Citrus rust mite (Phyllocoptruta oleivora), mite broad mite (Polyphagotarsonemus latus), cyclamen mite Cyclamen mite (Phytonemus pallidus), chuone mus mite Mite spider mite Citrus red mite (Panonychus citri), Mite spider mite Spider mite (Panonychus mori), Apple spider mite European red mite (Panonychus ulmi), Kanzawa spider mite Kanzawa spider mite (Tetranychus kanzawai), Nami spider mite Two mite Two-spot mite erythrocephalus), wheat mite Winter grain mite (Penthaleus major), Etsurombicula wichmanni, Miyagata pine tsutsumugi Trombiculid mite (Helenicula miyagawai), red tsutsugamushi (Leptotrombidium akamushi), yellow tsutsugamushi Prostigmata mites, such as Leptotrombidium pallida, Tsutsutsugamushi mite (Leptotrombidium scutellare),
English fowl tick (Argas persicus), tick soft tick (Ornithodoros moubata), relapsing fever tick (Ornithodoros turicata), spinose ear tick (Otobius megnini), Lone star tick (Lone star tick) Amblyomma americanum, Gulf coast tick (Amblyomma maculatum), Tick tick (Haemaphysalis campanulata), Tick tick (Haemaphysalis flava), Bite tick (Haemaphysalis longicornis), Mega physic tick (Haemaphysalis longicornis) aegyptium), Mediterranean tick (Hyalomma marginatum), Tropical cattle tick (Boophilus microplus), Ixodes nipponensis, Yamato tick (Ixodes ovatus), Western black-legge d tick (Ixodes pacifcus), Schulze tick Taiga tick (Ixodes persulcatus), Sheep tick Castor bean tick (Ixodes ricinus), Black-legged tick (Ixodes scapularis), Tropical horse tick (Anocentor nitens), Rocky Mountains Rocky Mountain wood tick (Dermacentor andersoni), Pacific Coast tick (Dermacentor occidentalis), Amikemeka tick Ornate cow tick (Dermacentor reticulatus), American dog tick American dog tick (Dermacentor variabilis), Ripicentor spp. Tick American cattle tick (Rhipicephalus annulatus), Brown dog tick (Rhipicephalus sanguineus) and other ticks (Metastigmata) ticks,
Red mite (Dermanyssus gallinae), house dust mite Tropical rat mite (Ornithonyssus bacoti), northern fowl mite (Ornithonyssus sylviarum), honey bee mite Honeybee mite (Varroa destructor), honeybee mite Varroa mite Varroa mite (Mesostigmata) mites,
Pancreas (Architaenioglossa) gastropod, such as Apple snail (Pomacea canaliculata)
Giant African snail (Achatina fulica), terrestrial slug (Limax marginatus), slug slug (Meghimatium bilineatum), Korean round snail (Acusta despecta sieboldiana), Miss maimai Land snio (Euhadra mai) Eyes (Stylommatophora) gastropods,
Giant kidney worm (Dioctophyma renale), ringed capillary worm Thread worms (Capillaria annulata), torsion capillary nematode Cropworm (Capillaria contorta), liver capillary nematode Capillary liver worm (Capillaria hepatica), penetrating capillary nematode (Capillaria) perforans), Philippine Capillaria philippinensis, Capillaria suis, Caterpillar Whipworm (Trichuris discolor), Whipworm Whipworm (Trichuris ovis), Pig whipworm Pig Whipworm (Trichuris suis), human Enoplida nematodes such as the whipworm Human whipworm (Trichuris trichiura), dog whipworm Dog whipworm (Trichuris vulpis), Trichinella pork worm (Trichinella spiralis),
桿 such as Nipple faecal nematode Intestinal threadworm (Strongyloides papillosus), cat fecal nematode (Strongyloides planiceps), pig fecal nematode Pig threadworm (Strongyloides ransomi), human fecal nematode Threadworm (Strongyloides stercoralis), Micronema spp. Rhabditida nematode,
Brazilian Hookworm (Ancylostoma braziliense), Dog Hookworm Dog hookworm (Ancylostoma caninum), Zubini Hookworm Old World hookworm (Ancylostoma duodenale), Cat Hookworm Cat hookworm (Ancylostoma tubaeforme), Narrowhead Hookworm The Northern hookworm of dogs (Uncinaria stenocephala) Caterpillar Cattle hookworm (Bunostomum phlebotomum), Sheep worm, Small ruminant hookworm (Bunostomum trigonocephalum), American worm New World hookworm (Necator americanus), Cyathostomum spp., Cylicocyclus spyl. spp.), Cylicostephanus spp., Donkeys (Strongylus asini), edentulous (Strongylus edentatus), Horse worms Blood worm (Strongylus equinus), Common worms Blood worm (Strongylus vulgaris) Large-mouthed bowel worm (Chabertia ovina), Indian nodular worm (Oesophagostomum brevic) audatum), Colombian nodule worm (Oesophagostomum columbianum), Nodule worm (Oesophagostomum dentatum), Nodular worm (Oesophagostomum georgianum), Nodular worm (Oesophagostomum columbianum) Nodular worm (Oesophagostomum quadrispinulatum), cattle intestinal nodular worm (Oesophagostomum radiatum), goat intestinal nodular worm (Oesophagostomum venulosum), scrijabin worm (Syngamus skrjabinomorpha), chicken worm moth trachea (Syngamus skrjabinomorpha) Swine kidney worm (Stephanurus dentatus), Couperia cattle bankrupt worm (Cooperia oncophora), red stomach worm (Hyostrongylus rubidus), stomach hair worm (Trichostrongylus axei), serpentine ciliate nematode (Trichostrongylus colubriformis), Oriental ciliate nematode Oriental trichostrongylus (Trichostrongylus orientalis), torsion stomachworm Red stomach worm (Haemonchus co ntortus), cattle stomach worm (Mecistocirrus digitatus), Ostertag stomach worm (Ostertagia ostertagi), filamentous lungworm Common lungworm (Dictyocaulus filaria), bovine lungworm Bovine lungworm (Dictyocaulus viviparus) Insect worms (Nematodirus filicollis), Swine lungworm (Metastrongylus elongatus), Lungworm (Filaroides hirthi), Lungworm (Crenosoma aerophila), Fox lungworm (Crenosoma vulpis) Strong lungida nematodes such as Rat lung worm (Angiostrongylus cantonensis), Schistosoma nematode French heartworm (Angiostrongylus vasorum), Protostrongylus spp.
Rice white nematode (Aphelenchoides besseyi), Pine wood nematode (Bursaphelenchus xylophilus) nematode (Aphelenchida) nematode,
Potato cyst nematode (Globodera rostochiensis), wheat cyst nematode Cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Seterbean cyst nematode (Heterodera glycines)), arenaria root nematode (Peterut root-Menot nematode) -knot nematode (Meloidogyne hapla), Southern root-knot nematode (Meloidogyne incognita), Java root-knot nematode (Meloidogyne javanica), Southern root-kion nematode Coffee root-lesion nematode (Pratylus nechade) Root-lesion nematode (Pratylenchus loosi), Cobb's root-lesion nematode (Pratylenchus penetrans), Crested nematode Walnut root-lesion nematode (Pratylenchus vulnus), etc. lenchida) nematode,
Oxyurida nematodes such as human worm Pinworm (Enterobius vermicularis), horse worm Equine pinworm (Oxyuris equi), rabbit worm Rabbit pinworm (Passalurus ambiguus),
Pig roundworm (Ascaris suum), Horse roundworm Horse roundworm (Parascaris equorum), Dog roundworm Dog roundworm (Toxascaris leonina), Dog roundworm Dog intestinal roundworm (Toxocara canis), Cat roundworm Feline roundworm (Toxocara cati), Cattle roundworm Large cattle roundworm (Toxocara vitulorum), Anisakis spp., Pseudoterranova spp., chicken caecal caecal worm (Heterakis gallinarum), chicken roundworm (Ascaridia galli) and other roundworms (Ascaridida) Nematode,
Medinaworm Guinea worm (Dracunculus medinensis), Dolores jaw-and-mouth beetle (Gnathostoma doloresi), Ganthostoma hispidum, Japanese jaw-and-mouth beetle (Gnathostoma nipponicum), Reddish-coloured worm (Gnathostoma spinigerum) Dog stomach worm (Physaloptera canis), cat stomach worm (Physaloptera felidis, P. praeputialis), lala gastroworm Feline / canine stomach worm (Physaloptera rara), oriental eyeworm Eye worm (Thelazia callipaeda), Bovine eyeworm (Thelazia rhodesi), Large mouth stomach worm (Draschia megastoma), Equine stomach worm (Habronema microstoma), Stomach worm (Habronema muscae), Beautiful esophagus Gullet worm ( Gongylonema pulchrum), Thick stomach worm (Ascarops strongylina), Parafilaria (Parafilaria bovicola), Parafilaria multipapillosa, Stephanofilaria okinawaensis), Bancroft filaria (Wuchereria bancrofti), Malay filamentous worm (Brugia malayi), Neck threadworm (Onchocerca cervicalis), Gibson filamentous worm (Onchocerca gibsoni), Cattle filarial worm (Onchocercer gautum) ), Convolvulus (Onchocerca volvulus), finger filamentous worm Bovine filarial worm (Setaria digitata), equine filamentous peritoneal worm (Setaria equina), papillary larva (Setaria labiatopapillosa), marshall filariae (Setaria marshalli), dog Spirurida nematodes, such as the dog heartworm (Dirofilaria immitis) and the African eye worm (Loa loa),
Bald worms such as Moniliformis moniliformis, Giant thorny-headed worm (Macracanthorhynchus hirudinaceus),
Artificial leaves such as Fish tapeworm (Diphyllobothrium latum), Diphyllobothrium nihonkaiense, Manson tapeworm (Spirometra erinaceieuropaei), Diplogonoporus grandis Eye (Pseudophyllidea) tapeworm,
Wire worms (Mesocestoides lineatus), striped worms Chicken tapeworm (Raillietina cesticillus), spiny cleft worm Fowl tapeworm (Raillietina echinobothrida), square tapeworm Chicken tapeworm (Raillietina tetragona), canine tapeworm (Taenia hydatigena), Canine tapeworm (Taenia multiceps), sheep worm Sheep measles (Taenia ovis), beetle tapeworm Dog tapeworm (Taenia pisiformis), striped beetle Beef tapeworm (Taenia saginata), striped worm Tapeworm (Taenia serialis) ), Rodentworm Pork tapeworm (Taenia solium), caterpillar Feline tapeworm (Taenia taeniaeformis), single tapeworm Hydatid tapeworm (Echinococcus granulosus), multi-budworm, small fox tapeworm (Echinococcus multilocularis), cat (Echinococcus oligarthrus), Vogel's crustacean (Echinococcus vogeli), reduced tapeworm Rat tapeworm (Hymenolepis diminuta), small tapeworm Dwarf tapeworm (Hymenolepis nana), crustacea double-pored dog tapeworm (Dipylidium ca ninum), cuneate tapeworms (Amoebotaenia sphenoides), funnel-like crustaceans (Choanotaenia infundibulum), quail crustaceans (Metroliasthes coturnix), crustacea Equine tapeworm (Anoplocephala magna), phytophyte crustacean Cecal tapeworm (Anoplocephala perfoliata), papillae Insects Dwarf equine tapeworm (Paranoplocephala mamillana), Benedenta worm Common tapeworm (Moniezia benedeni), expanded tapeworm Sheep tapeworm (Moniezia expansa), Stysia spp.
Striated insects (Pharyngostomum cordatum), Schistosoma haematobium, Schistosoma haematobium, Schistosoma japonicum, Schistosoma japonicum, Schistosoma mansoni, etc.
Echinostoma cinetorchis, Echinostoma hortense, Giant liver fluke (Fasciola gigantica), Liver common liver fluke (Fasciola hepatica), Fasciolopsis buski, Flat belly twin Echinostomida, such as Homalogaster paloniae,
Continental flukes (Dicrocoelium chinensis), moth-type flukes Lancet liver fluke (Dicrocoelium dendriticum), African moth-type flukes African lancet fluke (Dicrocoelium hospes), small pancreatic folds (Eurytrema coelomaticum), pancreatic folds Pancreatic fluke (Eurytrema pancreaticum) Paragonimus miyazakii, Paragonimus ohirai, Westermann Lung fluke (Paragonimus westermani), etc. Platimorchiida
Amphimerus spp., Liver fluke Chinese liver fluke (Clonorchis sinensis), Cat liver fluke Cat liver fluke (Opisthorchis felineus), Thai liver fluke Southeast Aasian liver fluke (Opisthorchis viverrini), Pseudamphistom spp .), Metrochis spp., Parametorchis spp., Malformed fluke (Heterophyes heterophyes), Metagonimus yokokawai, foregut fluke (Pygidiopsis summa), etc. Opisthorchiida) fluke,
Amoeba such as Entamoeba histolytica, E. invadens,
Futago Babesia (Babesia bigemina), Cattle Babesia bovis, Big Horse Babesia caballi, Dog Babesia canis, Cat Babesia felis, Gibson dog Babesia gibsoni, Large Piroplasma (Babesia ovata) ), Cytauxzoon felis, tropical piroplasmosis Tyleria (Theileria annulata), pseudocoastal fever Tyreria (Theileria mutans), small piroplasma (Theileria orientalis), east coast fever Tyrelia (Theileria parva), etc. Piroplasmida sporophytes,
Haemoproteus mansoni, chicken leucocytozone (Leucocytozoon caulleryi), Plasmodium falciparum, Plasmodium malariae, Plasmodium ovale, Plasmodium ovale Haemosporida spores such as Plasmodium vivax,
Caryospora spp., Eimeria acervulina, Eimeria bovis, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria necatrix Eimeria ovinoidalis, rabbit liver coccidium (Eimeria stiedae), chicken cecal coccidium (Eimeria tenella), dog isospora canis, feline isospora (Isospora felis), porcine isospora suis (Isospora suis), Tizeria aleni , Tyzzeria anseris, Tyzzeria perniciosa, Wenyonella anatis, Wenyonella gagari, Cryptosporidium canis, cat crypt Cryptosporidium felis, Cryptosporidium hominis, turkey Cryptosporidium meleagridis, Cryptosporidium muris, small Cryptosporidium parvco, sarcosis (Sarcocystis cruzi), Sarcocystis felis, Sarcocystis hominis, Sarcocystis miescheriana, Sarcocystis neurona, Sarcocystis colostis tenis S tenis Sarcocystis ovalis), Toxoplasma gondii, dog hepatozoon (Hepatozoon canis), cat hepatozoon (Hepatozoon felis), etc. cidiorida) spores,
Vestibuliferida ciliates, such as large intestine barantidium coli,
Histomanas meleagridis, Pentatrichomonas hominis, Trichomonas tenax and other Trichomonadida flagellates,
Dipromonads (Diplomonadida) flagellates such as Giardia intestinalis, Giardia muris, turkey hexamita (Hexamita meleagridis), Hexamita parva,
Leishmania donovani, Leishmania infantum, Leishmania major, Leishmania tropica, Trypanosoma brucei gambiense, Trypanosoma brucei cruise, Trypanosoma brucei rhodesi Examples include Trypanosoma cruzi, Trypanosoma equiperdum, Trypanosoma evansi, and Kinetoplastida flagellates, which can be controlled using the compounds of the present invention. Pests and ectoparasites such as livestock, poultry, and pets are not limited to these.
　さらに、本発明化合物は、有機燐系化合物、カーバメート系化合物又はピレスロイド系化合物等の既存の殺虫剤に対して抵抗性の発達した有害生物に対しても有効である。
　すなわち、本発明化合物は、粘管目(トビムシ目)、網翅目(ゴキブリ目)、直翅目(バッタ目)、シロアリ目、総翅目(アザミウマ目)、半翅目(カメムシ目及びヨコバイ目)、鱗翅目(チョウ目)、鞘翅目(コウチュウ目)、膜翅目(ハチ目)、双翅目(ハエ目)等の翅目(ノミ目)及びシラミ目等の昆虫類、ダニ類、腹足類並びに線虫類等に属する有害生物を低濃度で有効に防除することが出来る。一方、本発明化合物はホ乳類、魚類、甲殻類及び益虫(ミツバチ、マルハナバチ等の有用昆虫や、ツヤコバチ、アブラバチ、ヤドリバエ、ヒメハナカメムシ、カブリダニ等の天敵)に対して、ほとんど悪影響の無い極めて有用な特長を有している。 Furthermore, the compound of the present invention is also effective against pests having developed resistance against existing insecticides such as organophosphorus compounds, carbamate compounds or pyrethroid compounds.
That is, the compound of the present invention is composed of the order of mucous (Coleoptera); Eyes), Lepidoptera (Lepidoptera), Coleoptera (Coleoptera), Hymenoptera (Hymenoptera), Diptera (Flyes), etc. In addition, pests belonging to gastropods and nematodes can be effectively controlled at low concentrations. On the other hand, the compound of the present invention has extremely no adverse effect on mammals, fish, crustaceans and beneficial insects (beneficial insects such as honeybees, bumblebees, natural enemies such as honeybees, wasps, mistletoe, spider mites, burdock mites). Has useful features.
　本発明化合物を使用するにあたっては、通常適当な固体担体又は液体担体と混合し、更に所望により界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤、消泡剤、防腐剤、分解防止剤等を添加して、液剤（soluble concentrate）、乳剤（emulsifiable concentrate）、水和剤（wettable powder）、水溶剤（water soluble powder）、顆粒水和剤（water dispersible granule）、顆粒水溶剤（water soluble granule）、懸濁剤（suspension concentrate）、乳濁剤（concentrated emulsion）、サスポエマルジョン（suspoemulsion）、マイクロエマルジョン（microemulsion）、粉剤（dustable powder）、粒剤（granule）、錠剤（tablet）、乳化性ゲル剤（emulsifiable gel）等の任意の剤型の製剤にて実用に供することができる。また、省力化及び安全性向上の観点から、上記任意の剤型の製剤を、水溶性カプセル、水溶性フィルムの袋等の水溶性包装体に封入して供することもできる。 When using the compound of the present invention, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreezing agent, binder, anti-caking agent. , Disintegrating agents, antifoaming agents, antiseptics, anti-degradation agents, etc., adding liquid (soluble concentrate), emulsion (emulsifiable concentrate), wettable powder (wettable powder), water solvent (water soluble powder) Water dispersible granule, water soluble granule, suspension 剤 concentrate, emulsion 濁 concentrated 、 suspoemulsion, microemulsion, microemulsion, dustable powder ), Granules, tablets, emulsifiable gels, etc., can be put to practical use. In addition, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule or a water-soluble film bag.
　固体担体としては、例えば石英、方解石、海泡石、ドロマイト、チョーク、カオリナイト、パイロフィライト、セリサイト、ハロサイト、メタハロサイト、木節粘土、蛙目粘土、陶石、ジークライト、アロフェン、シラス、きら、タルク、ベントナイト、活性白土、酸性白土、軽石、アタパルジャイト、ゼオライト、珪藻土等の天然鉱物質、例えば焼成クレー、パーライト、シラスバルーン、バーミキュライト、アタパルガスクレー、焼成珪藻土等の天然鉱物質の焼成品、例えば炭酸マグネシウム、炭酸カルシウム、炭酸ナトリウム、炭酸水素ナトリウム、硫酸アンモニウム、硫酸ナトリウム、硫酸マグネシウム、リン酸水素二アンモニウム、リン酸二水素アンモニウム、塩化カリウム等の無機塩類、例えばブドウ糖、果糖、しょ糖、乳糖等の糖類、例えば澱粉、粉末セルロース、デキストリン等の多糖類、例えば尿素、尿素誘導体、安息香酸、安息香酸の塩等の有機物、例えば木粉、コルク粉、トウモロコシ穂軸、クルミ殻、タバコ茎等の植物類、フライアッシュ、ホワイトカーボン（例えば、含水合成シリカ、無水合成シリカ、含水合成シリケート等）、肥料等が挙げられる。
　液体担体としては、例えばキシレン、アルキル（Ｃ9又はＣ10等）ベンゼン、フェニルキシリルエタン、アルキル（Ｃ1又はＣ3等）ナフタレン等の芳香族炭化水素類、マシン油、ノルマルパラフィン、イソパラフィン、ナフテン等の脂肪族炭化水素類、ケロシン等の芳香族炭化水素と脂肪族炭化水素の混合物、エタノール、イソプロパノール、シクロヘキサノール、フェノキシエタノール、ベンジルアルコール等のアルコール、エチレングリコール、プロピレングリコール、ジエチレングリコール、ヘキシレングリコール、ポリエチレングリコール、ポリプロピレングリコール等の多価アルコール、プロピルセロソルブ、ブチルセロソルブ、フェニルセロソルブ、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、プロピレングリコールモノフェニルエーテル等のエーテル、アセトフェノン、シクロヘキサノン、γ－ブチロラクトン等のケトン、脂肪酸メチルエステル、コハク酸ジアルキルエステル、グルタミン酸ジアルキルエステル、アジピン酸ジアルキルエステル、フタル酸ジアルキルエステル等のエステル、Ｎ－アルキル（Ｃ1、Ｃ8又はＣ12等）ピロリドン等の酸アミド、大豆油、アマニ油、ナタネ油、ヤシ油、綿実油、ヒマシ油等の油脂、ジメチルスルホキシド、水等が挙げられる。
　これら固体及び液体担体は、単独で用いても２種以上を併用してもよい。 Examples of the solid carrier include quartz, calcite, gypsum, dolomite, chalk, kaolinite, pyrophyllite, sericite, halosite, metahalosite, kibushi clay, glazed clay, porcelain stone, siegrite, and allophane. , Shirasu, Kira, Talc, Bentonite, activated clay, acid clay, pumice, attapulgite, zeolite, diatomaceous earth and other natural minerals such as calcined clay, perlite, shirasu balloon, vermiculite, attapulgus clay, calcined diatomaceous earth and other natural minerals Baked products such as magnesium carbonate, calcium carbonate, sodium carbonate, sodium bicarbonate, ammonium sulfate, sodium sulfate, magnesium sulfate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium chloride and the like, such as glucose, fructose , Sucrose, lactose, etc. Sugars, eg polysaccharides such as starch, powdered cellulose, dextrin, organic substances such as urea, urea derivatives, benzoic acid, benzoic acid salts, plants such as wood flour, cork flour, corn cob, walnut shell, tobacco stem , Fly ash, white carbon (for example, hydrous synthetic silica, anhydrous synthetic silica, hydrous synthetic silicate, etc.), fertilizer and the like.
Examples of the liquid carrier include xylene, alkyl (C 9 or C 10 etc.) benzene, phenyl xylyl ethane, alkyl (C 1 or C 3 etc.) naphthalene and other aromatic hydrocarbons, machine oil, normal paraffin, isoparaffin, Aliphatic hydrocarbons such as naphthene, mixtures of aromatic and aliphatic hydrocarbons such as kerosene, alcohols such as ethanol, isopropanol, cyclohexanol, phenoxyethanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, hexylene glycol , Polyhydric alcohols such as polyethylene glycol and polypropylene glycol, propyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol monomethyl ether, propylene glycol monoethyl Ethers, ethers such as propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monophenyl ether, ketones such as acetophenone, cyclohexanone, γ-butyrolactone, fatty acid methyl esters, dialkyl esters of succinic acid, dialkyl esters of glutamic acid, dialkyl esters of adipic acid , Esters such as dialkyl phthalates, acid amides such as N-alkyl (C 1 , C 8 or C 12 ) pyrrolidone, oils such as soybean oil, linseed oil, rapeseed oil, coconut oil, cottonseed oil, castor oil, dimethyl Examples thereof include sulfoxide and water.
These solid and liquid carriers may be used alone or in combination of two or more.
　界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキル（モノ又はジ）フェニルエーテル、ポリオキシエチレン（モノ、ジ又はトリ）スチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸（モノ又はジ）エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ヒマシ油エチレンオキサイド付加物、アセチレングリコール、アセチレンアルコール、アセチレングリコールのエチレンオキサイド付加物、アセチレンアルコールのエチレンオキサイド付加物、アルキルグリコシド等のノニオン性界面活性剤、アルキル硫酸エステル塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルエーテル硫酸又は燐酸エステル塩、ポリオキシエチレン（モノ又はジ）アルキルフェニルエーテル硫酸又は燐酸エステル塩、ポリオキシエチレン（モノ、ジ又はトリ）スチリルフェニルエーテル硫酸又は燐酸エステル塩、ポリカルボン酸塩（例えば、ポリアクリル酸塩、ポリマレイン酸塩及びマレイン酸とオレフィンとの共重合物等）、ポリスチレンスルホン酸塩等のアニオン性界面活性剤、アルキルアミン塩、アルキル４級アンモニウム塩等のカチオン性界面活性剤、アミノ酸型、ベタイン型等の両性界面活性剤、シリコーン系界面活性剤、フッ素系界面活性剤等が挙げられる。
　これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤１００重量部に対し、通常０．０５～２０重量部、好ましくは０．５～１０重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても２種以上を併用してもよい。 Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene Ethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, alkyl Nonionic surfactants such as glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfates Succinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester salt, polyoxyethylene (Mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg, polyacrylate, polymaleate and maleate) Copolymers of acid and olefins), anionic surfactants such as polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, and amphoteric surfactants such as amino acid types and betaine types Agent, silicone Surfactants, fluorochemical surfactants, and the like.
The content of these surfactants is not particularly limited, but is usually in the range of 0.05 to 20 parts by weight, preferably 0.5 to 10 parts by weight with respect to 100 parts by weight of the preparation of the present invention. . These surfactants may be used alone or in combination of two or more.
　本発明化合物の施用薬量は、適用場面、施用時期、施用方法、栽培作物等により差異は有るが、一般には有効成分量としてヘクタール（ha）当たり０.００５～５０kg程度、好ましくは０．０１～５ｋｇが適当である。
　一方、家畜及び愛玩動物としての哺乳動物、並びに鳥類の外部又は内部寄生虫の防除に本発明化合物を使用するにあたっては、本発明化合物の有効量を、製剤用添加物とともに経口投与、注射（筋肉内、皮下、静脈内、腹腔内）等の非経口投与；浸漬、スプレー、入浴、洗浄、滴下（pouring-on)、スポッティング(spotting-on)、ダスティング(dusting)等の経皮投与；経鼻投与により投与することができる。
　本発明化合物は、細片、プレート、バンド、カラー、イヤー・マーク(ear mark)、リム(limb)・バンド、標識装置等を用いた成形製品により投与することができる。投与にあたっては、本発明化合物を投与経路に適した任意の剤型とすることができる。 The application amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally the active ingredient amount is about 0.005 to 50 kg per hectare (ha), preferably 0.01. ~ 5 kg is suitable.
On the other hand, when using the compound of the present invention for the control of mammals as domestic animals and pets, and the control of ectoparasites or endoparasites in birds, an effective amount of the compound of the present invention is administered orally, and injected (muscles) together with pharmaceutical additives. Parenteral administration such as internal, subcutaneous, intravenous, intraperitoneal); transdermal administration such as immersion, spraying, bathing, washing, pouring-on, spotting-on, dusting; Administration can be by nasal administration.
The compounds of the present invention can be administered by molded products using strips, plates, bands, collars, ear marks, limb bands, labeling devices and the like. In administration, the compound of the present invention can be in any dosage form suitable for the administration route.
　調製される任意の剤型としては、粉剤、粒剤、水和剤、ペレット、錠剤、大丸薬、カプセル剤、活性化合物を含む成形製品等の固体調製物；注射用液剤；経口用液剤；皮膚上又は体腔中に用いる液剤；滴下（Pour-on)剤、点下(Spot-on)剤、フロアブル剤、乳剤等の溶液調製物；軟膏剤、ゲル等の半固体調製物等が挙げられる。 Arbitrary dosage forms to be prepared include powders, granules, wettable powders, pellets, tablets, large pills, capsules, solid preparations such as molded products containing active compounds; injection solutions; oral solutions; skin Liquid preparations used above or in body cavities; Solution preparations such as Pour-on agents, Spot-on agents, flowable agents, and emulsions; Semi-solid preparations such as ointments and gels.
　固体調製物は、主に経口投与若しくは水等で希釈して経皮投与、又は環境処理にて用いることができる。固体調製物は、活性化合物を必要ならば補助剤を加えて適当な賦形剤と共に混合し、所望の形状に変えることにより調製できる。適当な賦形剤としては、例えば炭酸塩、炭酸水素塩、リン酸塩、酸化アルミニウム、シリカ、粘土等の無機物質、糖、セルロース、粉砕された穀物、澱粉等の有機物質が挙げられる。 The solid preparation can be mainly used for oral administration or transdermal administration after dilution with water or environmental treatment. Solid preparations can be prepared by adding the active compound, if necessary, with adjuncts and mixing with appropriate excipients to give the desired shape. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, celluloses, ground grains, and starches.
　注射用液剤は、静脈内、筋肉内及び皮下に投与できる。注射用液剤は、活性化合物を適当な溶媒に溶解させ、必要ならば可溶化剤、酸、塩基、緩衝用塩、酸化防止剤、保護剤等の添加剤を加えることにより調製できる。
　適当な溶媒としては、水、エタノール、ブタノール、ベンジルアルコール、グリセリン、プロピレングリコール、ポリエチレングリコール、Ｎ－メチルピロリドン及びこれらの混合物、生理学的に許容しうる植物油、注射に適する合成油等が挙げられる。
　可溶化剤としては、ポリビニルピロリドン、ポリオキシエチル化されたヒマシ油、ポリオキシエチル化されたソルビタンエステル等が挙げられる。
　保護剤には、ベンジルアルコール、トリクロロブタノール、ｐ－ヒドロキシ安息香酸エステル、ｎ－ブタノール等が挙げられる。
　経口用液剤は直接又は希釈して投与することができる。注射用液剤と同様に調製することができる。
　フロアブル剤、乳剤等は直接又は希釈して経皮的に、あるいは環境処理にて投与できる。 Injection solutions can be administered intravenously, intramuscularly and subcutaneously. Injection solutions can be prepared by dissolving the active compound in a suitable solvent and adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, protective agents, etc., if necessary.
Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
Examples of the solubilizer include polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan ester, and the like.
Examples of the protective agent include benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol and the like.
Oral solutions can be administered directly or diluted. It can be prepared in the same manner as an injectable solution.
Flowables, emulsions and the like can be administered directly or diluted transdermally or by environmental treatment.
　皮膚上で用いる液剤は、滴下し、広げ、すり込み、噴霧し、散布するか、又は浸漬（浸漬、入浴又は洗浄）により塗布することにより投与できる。これらの液剤は注射用液剤と同様に調製できる。
　滴下(Pour-on)剤及び点下(Spot-on)剤は、皮膚の限定された場所に滴下するか、又は噴霧し、これにより活性化合物を皮膚に浸漬させ、全身的に作用させることができる。
　滴下剤及び点下剤は、有効成分を適当な皮膚適合性溶媒又は溶媒混合物に溶解するか、懸濁させるか又は乳化することにより調製できる。必要ならば、界面活性剤、着色剤、吸収促進物質、酸化防止剤、光安定剤、接着剤等の補助剤を加えてもよい。
　適当な溶媒としては、水、アルカノール、グリコール、ポリエチレングリコール、ポリプロピレングリコール、グリセリン、ベンジルアルコール、フェニルエタノール、フェノキシエタノール、酢酸エチル、酢酸ブチル、安息香酸ベンジル、ジプロピレングリコールモノメチルエーテル、ジエチレングリコールモノブチルエーテル、アセトン、メチルエチルケトン、芳香族及び／又は脂肪族炭化水素、植物又は合成油、ＤＭＦ、流動パラフィン、軽質流動パラフィン、シリコーン、ジメチルアセトアミド、Ｎ－メチルピロリドン又は２，２－ジメチル－４－オキシ－メチレン－１，３－ジオキソランが挙げられる。
　吸収促進物質には、ＤＭＳＯ、ミリスチン酸イソプロピル、ペラルゴン酸ジプロピレングリコール、シリコーン油、脂肪族エステル、トリグリセリド、脂肪アルコール等が挙げられる。
　酸化防止剤には、亜硫酸塩、メタ重亜硫酸塩、アスコルビン酸、ブチルヒドロキシトルエン、ブチルヒドロキシアニソール、トコフェロール等が挙げられる。 Solutions used on the skin can be administered by dripping, spreading, rubbing, spraying, spraying or applying by dipping (immersion, bathing or washing). These solutions can be prepared in the same manner as injection solutions.
Pour-on and spot-on agents can be dripped or sprayed onto a limited area of the skin, so that the active compound is immersed in the skin and acts systemically. it can.
Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliary agents such as surfactants, colorants, absorption promoting substances, antioxidants, light stabilizers, and adhesives may be added.
Suitable solvents include water, alkanol, glycol, polyethylene glycol, polypropylene glycol, glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, Methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oil, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1, 3-dioxolane is mentioned.
Absorption promoting substances include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides, fatty alcohols and the like.
Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol and the like.
　乳剤は、経口投与、経皮投与又は注射として投与できる。
　乳剤は、有効成分を疎水性相又は親水性相に溶解させ、このものを適当な乳化剤により、必要ならばさらに着色剤、吸収促進物質、保護剤、酸化防止剤、遮光剤、増粘物質等の補助剤と共に他の相の溶媒と均質化することにより調製できる。
　疎水性相（油）としては、パラフィン油、シリコーン油、ゴマ油、アーモンド油、ヒマシ油、合成トリグリセリド、ステアリン酸エチル、アジピン酸ジーｎ－ブチリル、ラウリル酸ヘキシル、ペラルゴン酸ジプロピレングリコール、分枝鎖状の短鎖長脂肪酸と鎖長Ｃ１６～Ｃ１８の飽和脂肪酸とのエステル、ミリスチン酸イソプロピル、パルミチン酸イソプロピル、鎖長Ｃ１２～Ｃ１８の飽和脂肪アルコールのカプリル／カプリン酸エステル、ステアリン酸イソプロピル、オレイン酸オレイル、オレイン酸デシル、オレイン酸エチル、乳酸エチル、ワックス状脂肪酸エステル、フタル酸ジブチル、アジピン酸ジイソプロピル、イソトリデシルアルコール、２－オクチルドデカノール、セチルステアリルアルコール、オレイルアルコール等が挙げられる。
　親水性相としては、水、プロピレングリコール、グリセリン、ソルビトール等が挙げられる。
　乳化剤としては、ポリオキシエチル化されたヒマシ油、ポリオキシエチル化されたモノオレフィン酸ソルビタン、モノステアリン酸ソルビタン、モノステアリン酸グリセリン、ステアリン酸ポリオキシエチル、アルキルフェノールポリグリコールエーテル等の非イオン性界面活性剤；Ｎ－ラウリル－β－イミノジプロピオン酸二ナトリウム、レシチン等の両性界面活性剤；ラウリル硫酸ナトリウム、脂肪アルコール硫酸エーテル、モノ／ジアルキルポリグリコールオルトリン酸エステルのモノエタノールアミン塩等の陰イオン性界面活性剤；塩化セチルトリメチルアンモニウム等の陽イオン性界面活性剤等が挙げられる。
　他の補助剤として、カルボキシメチルセルロース、メチルセルロース、ポリアクリレート、アルギネート、ゼラチン、アラビアゴム、ポリビニルピロリドン、ポリビニルアルコール、メチルビニルエーテル、無水マレイン酸の共重合体、ポリエチレングリコール、ワックス、コロイド状シリカ等が挙げられる。
　半固体調製物は皮膚上に塗布するか、若しくは広げるか、又は体腔中に導入することにより投与できる。
　ゲルは注射用液剤について上記したように調製した溶液に、軟膏状の粘稠性を有する透明な物質を生じさせるに十分なシックナーを加えることにより調製できる。 The emulsion can be administered orally, transdermally or as an injection.
In the emulsion, the active ingredient is dissolved in a hydrophobic phase or a hydrophilic phase, and this is further added with a suitable emulsifier, and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc. Can be prepared by homogenizing with other phase solvents together with other auxiliary agents.
As hydrophobic phase (oil), paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, branched chain Of a short fatty acid having a chain length and a saturated fatty acid having a chain length of C16 to C18, isopropyl myristate, isopropyl palmitate, capryl / caprate of a saturated fatty alcohol having a chain length of C12 to C18, isopropyl stearate, oleyl oleate Decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetyl stearyl alcohol, oleyl alcohol, etc. It is.
Examples of the hydrophilic phase include water, propylene glycol, glycerin, sorbitol and the like.
As an emulsifier, nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc. Activators; amphoteric surfactants such as disodium N-lauryl-β-iminodipropionate and lecithin; anions such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate Surfactants; cationic surfactants such as cetyltrimethylammonium chloride.
Other adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymer, polyethylene glycol, wax, colloidal silica and the like. .
Semi-solid preparations can be administered by application on the skin or spreading or introduction into body cavities.
Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.
　次に本発明化合物を用いる場合の製剤の配合例を示す。但し本発明の配合例は、これらのみに限定されるものではない。なお、以下の配合例において「部」は重量部を意味する。 Next, formulation examples of the preparation when the compound of the present invention is used are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.
　〔水和剤〕
本発明化合物　　　　　　　　０.１～８０部
固体担体　　　　　　　　　　５～９８.９部
界面活性剤　　　　　　　　　　１～１０部
その他　　　　　　　　　　　　　０～５部
　その他として、例えば固結防止剤、分解防止剤等が挙げられる。 [Wettable powder]
Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agent, decomposition inhibitor and the like.
　〔乳剤〕
本発明化合物　　　　　　　　０.１～３０部
液体担体　　　　　　　　　　４５～９５部
界面活性剤　　　　　　　　　４.９～１５部
その他　　　　　　　　　　　　０～１０部
　その他として、例えば展着剤、分解防止剤等が挙げられる。 〔emulsion〕
Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.
　〔懸濁剤〕
本発明化合物　　　　　　　　０.１～７０部
液体担体　　　　　　　　１５～９８.８９部
界面活性剤　　　　　　　　　　１～１２部
その他　　　　　　　　　　０.０１～３０部
　その他として、例えば凍結防止剤、増粘剤等が挙げられる。 [Suspension]
Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners.
　〔顆粒水和剤〕
本発明化合物　　　　　　　　０.１～９０部
固体担体　　　　　　　　　　０～９８.９部
界面活性剤　　　　　　　　　　１～２０部
その他　　　　　　　　　　　　０～１０部
　その他として、例えば結合剤、分解防止剤等が挙げられる。 (Granule wettable powder)
Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors and the like.
　〔液剤〕
本発明化合物　　　　　　　０.０１～７０部
液体担体　　　　　　　　２０～９９.９９部
その他　　　　　　　　　　　　０～１０部
　その他として、例えば凍結防止剤、展着剤等が挙げられる。 [Liquid]
Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, antifreezing agents and spreading agents.
　〔粒剤〕
本発明化合物　　　　　　　０.０１～８０部
固体担体　　　　　　　　１０～９９.９９部
その他　　　　　　　　　　　　０～１０部
　その他として、例えば結合剤、分解防止剤等が挙げられる。 [Granule]
Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors and the like.
　〔粉剤〕
本発明化合物　　　　　　　０.０１～３０部
固体担体　　　　　　　　６５～９９.９９部
その他　　　　　　　　　　　　　０～５部
　その他として、例えばドリフト防止剤、分解防止剤等が挙げられる。 [Dust]
Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, drift inhibitors and decomposition inhibitors.
　次に、本発明化合物を有効成分とする製剤例をより具体的に示すが、本発明はこれらに限定されるものではない。
　尚、以下の配合例において、「部」は重量部を意味する。
　〔配合例１〕水和剤
本発明化合物No.１-００１　　　　　２０部
パイロフィライト　　　　　　　　　７４部
ソルポール５０３９　　　　　　　　　４部
（非イオン性界面活性剤とアニオン性界面活性剤との混合物：東邦化学工業社製、商品名）
カープレックス＃８０Ｄ　　　　　　　２部
（合成含水珪酸：塩野義製薬社製、商品名）
  以上を均一に混合粉砕して水和剤とする。 Next, although the formulation example which uses this invention compound as an active ingredient is shown more concretely, this invention is not limited to these.
In the following formulation examples, “parts” means parts by weight.
[Formulation Example 1] wettable powder Compound No. 1-001 of the present invention 20 parts Pyrophyllite 74 parts Solpol 5039 4 parts (mixture of nonionic surfactant and anionic surfactant: manufactured by Toho Chemical Co., Ltd., Product name)
Carplex # 80D 2 parts (Synthetic hydrous silicic acid: manufactured by Shionogi & Co., Ltd., trade name)
The above is uniformly mixed and ground to obtain a wettable powder.
　〔配合例２〕乳  剤
本発明化合物No.１-００１　　　　　　５部
キシレン　　　　　　　　　　　　　７５部
Ｎ－メチルピロリドン　　　　　　　１５部
ソルポール２６８０　　　　　　　　　５部
（非イオン性界面活性剤とアニオン性界面活性剤との混合物：東邦化学工業社製、商品名）
  以上を均一に混合して乳剤とする。 [Formulation Example 2] Milk Compound of the present invention No.1-001 5 parts xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry (Product name)
The above is uniformly mixed to obtain an emulsion.
　〔配合例３〕懸濁剤
本発明化合物No.１-００１　　　　　　２５部
アグリゾールＳ－７１０　　　　　　　１０部
（非イオン性界面活性剤：花王社製、商品名）
ルノックス１０００Ｃ　　　　　　　　０.５部
（アニオン性界面活性剤：東邦化学工業社製、商品名）
キサンタンガム　　　　　　　　　　　０.２部
水　　　　　　　　　　　　　　　　６４.３部
  以上を均一に混合した後、湿式粉砕して懸濁剤とする。 [Formulation Example 3] Suspension Agent Compound No.1-001 25 parts Agrisol S-710 10 parts (Nonionic Surfactant: Kao Corporation, trade name)
LUNOX 1000C 0.5 part (anionic surfactant: Toho Chemical Industries, trade name)
Xanthan gum 0.2 parts water 64.3 parts After uniformly mixing the above, wet pulverize to make a suspension.
　〔配合例４〕顆粒水和剤
本発明化合物No.１-００１　　　　　　７５部
ハイテノールNE-15　　　　　　　　　　５部
（アニオン性界面活性剤：第一工業製薬社製、商品名）
バニレックスＮ　　　　　　　　　　　１０部
（アニオン性界面活性剤：日本製紙（株）商品名）
カープレックス＃８０Ｄ　　　　　　　１０部
（合成含水珪酸：塩野義製薬社製、商品名）
  以上を均一に混合粉砕した後、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥して顆粒水和剤とする。 [Formulation Example 4] Granule wettable powder Compound No. 1-1001 of the present invention 75 parts Hytenol NE-15 5 parts (anionic surfactant: trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (Synthetic hydrous silicic acid: manufactured by Shionogi & Co., Ltd., trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to obtain a granulated wettable powder.
　〔配合例５〕粒剤
本発明化合物No.１-００１　　　　　　　５部
ベントナイト　　　　　　　　　　　　５０部
タルク　　　　　　　　　　　　　　　４５部
　以上を均一に混合粉砕した後、少量の水を加えて撹拌混合し、押出式造粒機で造粒し、乾燥して粒剤とする。 [Formulation Example 5] Granules Compound No. 1-001 of the present invention 5 parts Bentonite 50 parts Talc 45 parts And dried into granules.
　〔配合例６〕粉剤
本発明化合物No.１-００１　　　　　　　３部
カープレックス＃８０Ｄ　　　　　　　０.５部
（合成含水珪酸：塩野義製薬社製、商品名）
カオリナイト　　　　　　　　　　　　９５部
リン酸ジイソプロピル　　　　　　　　１.５部
  以上を均一に混合粉砕して粉剤とする。
　使用に際しては、上記製剤を水で１～１００００倍に希釈して、又は希釈せずに直接散布する。 [Composition Example 6] Powder Compound of the present invention No.1-001 3 parts Carplex # 80D 0.5 part (Synthetic hydrous silicic acid: Shionogi & Co., trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above is uniformly mixed and ground to obtain a powder.
In use, the formulation is diluted 1 to 10,000 times with water or sprayed directly without dilution.
　〔配合例７〕水和剤調製物
本発明化合物No.１-００１　　　　　　　　　　　　　　２５部
ジイソブチルナフタレンスルホン酸ナトリウム　　　　　　１部
ｎ－ドデシルベンゼンスルホン酸カルシウム　　　　　　１０部
アルキルアリール　ポリグリコールエーテル　　　　　　１２部
ナフタレンスルホン酸ホルマリン縮合物のナトリウム塩　　３部
エマルジョン型シリコーン　　　　　　　　　　　　　　　１部
二酸化ケイ素　　　　　　　　　　　　　　　　　　　　　３部
カオリン　　　　　　　　　　　　　　　　　　　　　　４５部 [Formulation Example 7] wettable powder preparation Compound No. 1-001 of the present invention 25 parts sodium diisobutylnaphthalenesulfonate 1 part calcium n-dodecylbenzenesulfonate 10 parts alkylaryl polyglycol ether 12 parts naphthalenesulfonic acid formalin condensate Sodium salt 3 parts Emulsion type silicone 1 part Silicon dioxide 3 parts Kaolin 45 parts
　〔配合例８〕水溶性濃厚剤調製物
本発明化合物No.１-００１　　　　　　　　　　　　　　２０部
ポリオキシエチレンラウリルエーテル　　　　　　　　　　３部
ジオクチルスルホコハク酸ナトリウム　　　　　　　　　３.５部
ジメチルスルホキシド　　　　　　　　　　　　　　　　３７部
２－プロパノール　　　　　　　　　　　　　　　　　３６.５部 [Formulation Example 8] Preparation of water-soluble thickener Compound No. 1-001 of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctyl sulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-propanol 36.5 parts
　〔配合例９〕噴霧用液剤
本発明化合物No.１-００１　　　　　　　　　　　　　　　２部
ジメチルスルホキシド　　　　　　　　　　　　　　　　　１０部
２－プロパノール　　　　　　　　　　　　　　　　　　　３５部
アセトン　　　　　　　　　　　　　　　　　　　　　　　５３部 [Formulation example 9] Liquid agent for spraying This invention compound No.1-001 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts
　〔配合例１０〕経皮投与用液剤
本発明化合物No.１-００１　　　　　　　　　　　　　　　　５部
ヘキシレングリコール　　　　　　　　　　　　　　　　　５０部
イソプロパノール　　　　　　　　　　　　　　　　　　　４５部 [Formulation Example 10] Solution for transdermal administration Compound No. 1-001 of the present invention 5 parts Hexylene glycol 50 parts Isopropanol 45 parts
　〔配合例１１〕経皮投与用液剤
本発明化合物No.１-００１　　　　　　　　　　　　　　　　５部
プロピレングリコールモノメチルエーテル　　　　　　　　５０部
ジプロピレングリコール　　　　　　　　　　　　　　　　４５部 [Formulation Example 11] Solution for transdermal administration Compound No. 1-001 of the present invention 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts
　〔配合例１２〕経皮投与(滴下)用液剤
本発明化合物No.１-００１　　　　　　　　　　　　　　　　２部
軽質流動パラフィン　　　　　　　　　　　　　　　　　　９８部 [Formulation Example 12] Solution for transdermal administration (drip) The present compound No.1-001 2 parts Light liquid paraffin 98 parts
　〔配合例１３〕経皮投与(滴下)用液剤
本発明化合物No.１-００１　　　　　　　　　　　　　　　　２部
軽質流動パラフィン　　　　　　　　　　　　　　　　　　５８部
オリーブ油　　　　　　　　　　　　　　　　　　　　　　３０部
ＯＤＯ－Ｈ　　　　　　　　　　　　　　　　　　　　　　　９部
信越シリコーン　　　　　　　　　　　　　　　　　　　　　１部 [Formulation Example 13] Solution for transdermal administration (dropping) The present compound No.1-001 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part
　また、本発明化合物を農薬として使用する場合には、必要に応じて製剤時又は散布時に、他種の除草剤、各種殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土壌改良剤等と混合施用しても良い。
　特に他の農薬あるいは植物ホルモンと混合施用することにより、施用薬量の低減による低コスト化、混合薬剤の相乗作用による殺虫スペクトラムの拡大や、より高い有害生物防除効果が期待できる。この際、同時に複数の公知農薬との組み合わせも可能である。
本発明化合物と混合使用する農薬の種類としては、例えばザ・ペスティサイド・マニュアル（The Pesticide Manual）１５版、２００９年に記載されている化合物等が挙げられる。具体的にその一般名を例示すれば次の通りであるが、必ずしもこれらのみに限定されるものではない。 In addition, when the compound of the present invention is used as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, if necessary, at the time of formulation or spraying Alternatively, it may be mixed with a synergist, a fertilizer, a soil conditioner and the like.
In particular, by applying it in combination with other agricultural chemicals or plant hormones, it can be expected to reduce costs by reducing the amount of applied medicine, expand the insecticidal spectrum due to the synergistic action of the mixed drugs, and achieve higher pest control effects. At this time, a combination with a plurality of known agricultural chemicals is also possible.
Examples of the type of agricultural chemical used in combination with the compound of the present invention include compounds described in The Pesticide Manual 15th edition, 2009, and the like. Specific examples of common names are as follows, but the general names are not necessarily limited to these.
　殺菌剤：アシベンゾラルーＳ－メチル（acibenzolar-S-methyl）、アシルアミノベンザミド(acylaminobenzamide)、アシペタックス(acypetacs)、アルジモルフ(aldimorph) 、アメトクトラジン(ametoctradin)、アミスルブロム(amisulbrom)、アンバム(amobam)、アムプロピルホス（ampropyfos）、アニラジン（anilazine）、アザコナゾール（azaconazole）、アジチラム(azithiram)、アゾキシストロビン（azoxystrobin）、バリウムポリサルファイド(barium polysulfide)、ベナラキシル（benalaxyl）、ベナラキシル－Ｍ（benalaxyl-M）、ベノダニル（benodanil）、ベノミル（benomyl）、ベンキノックス(benquinox)、ベンタルロン(bentaluron)、ベンチアバリカルブ(benthiavalicarb)、ベンチアゾール(benthiazole)、ベンザマクリル（benzamacril）、ベンズアモルフ(benzamorf)、ベトキサジン（bethoxazine）、ビナパクリル（binapacryl）、ビフェニル（biphenyl）、ビテルタノール（bitertanol）、ブラストサイジン－Ｓ（blasticidin-S）、ビキサフェン（bixafen）、ボルドー液（bordeaux mixture）、ボスカリド(boscalid)、ブロモコナゾール（bromoconazole）、ブピリメート（bupirimate）、ブチオベート（buthiobate）、石灰硫黄合剤（calcium polysulfide）、カルシウムポリスルフィド（calcium polysulfide）、キャプタフォール（captafol）、キャプタン（captan）、カルプロパミド（carpropamid）、カルバモルフ(carbamorph)、カルベンダジン（carbendazim）、カルボキシン（carboxin）、カルボン(carvone)、チェシュントミクスチャ(cheshunt mixture)、キノメチオネート（chinomethionat）、クロベンチアゾン（chlobenthiazone）、クロラニフォルメタン(chloraniformethane)、クロラニル(chloranil)、クロルフェナゾール（chlorfenazol）、クロロネブ（chloroneb）、クロロピクリン(chloropicrin)、クロロタロニル（chlorothalonil）、クロロキノックス(chlorquinox)、クロゾリネート（chlozolinate）、クリムバゾール(climbazole)、クロトリマゾール(clotrimazole)、カッパーアセテイト(copper acetate)、塩基性炭酸銅(copper carbonate, basic)、水酸化第二銅(copper hydroxide)、カッパーナフタレン(copper naphthenate)、カッパーオルアイト(copper oleate)、カッパーオキシクロリド（copper oxychloride）、硫酸銅(copper sulfate)、塩基性硫酸銅(copper sulfate, basic)、カッパージンククロメイト(copper zinc chromate)、クフラネブ（cufraneb）、クプロバム(cuprobam)、シアゾファミド(cyazofamid)、シクラフルアミド(cyclafuramid)、シクロヘキシミド(cycloheximide)、シフルフェナミド(cyflufenamid)、シモキサニル（cymoxanil）、サイペンダゾール(cypendazole)、シプロコナゾール（cyproconazol）、シプロジニル（cyprodinil）、シプロフラム（cyprofuram）、ダゾメット(dazomet)、デバカルブ（debacarb）、デカフェンチン(decafentin)、デハイドロアセテイト(dehydroacetic acid)、ジクロフルアニド（dichlofluanid）、ジクロン(dichlone)、ジクロロフェン（dichlorophen）、ジクロゾリン(dichlozoline)、ジクロブトラゾール（diclobutrazol）、ジクロシメット（diclocymet）、ジクロメジン（diclomedine）、ジクロラン（dicloran）等。 Bactericides: acibenzolar-S-methyl, acylaminobenzamide, acypetacs, aldimorph, ametoctradin, amisulbrom, amobam, ampropyl Phos (ampropyfos), anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M (Benodanil), benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzamacril, benzamorf, bethoxazine, Binapacryl ), Biphenyl, bitertanol, blasticidin-S, bixafen, bordeaux mixture, boscalid, bromoconazole, bupirimate , Buthiobate, calcium polysulfide, calcium polysulfide, captafol, captan, carpropamid, carbamorph, carbendazim, Carboxin (carboxin), carvone, cheshunt mixture, chinomethionat, clobenthiazone, chloraniformethane, chloranil, chlorfenazol ), Chloro Chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, clotrimazole, copper acetoate, basic Copper carbonate, copper basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, base Copper sulfate, copper basic, copper zincate, cupraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamide, cyflufenamid ), Simoxanil, Cypendazole, Cypro Cyproconazol, cyprodinil, cyprofuram, dazomet, debacarb, decaentin, dehydroacetic acid, diclofluanid, dilone ), Dichlorophen, dichlorocloline, diclobutrazol, diclocymet, diclomedine, dicloran and the like.
　殺菌剤（続き）：ジエトフェンカルブ（diethofencarb）、ジフェノコナゾール（difenoconazole）、ジフルメトリン（diflumetorim）、ジメチリモール（dimethirimol）、ジメトモルフ（dimethomorph）、ジモキシストロビン(dimoxystrobin)、ジニコナゾール（diniconazole）、ジニコナゾール－Ｍ（diniconazole-M）、ジノブトン(dinobuton)、ジノカップ（dinocap）、ジノカップ－４(dinocap-4)、ジノカップ－６(dinocap-6)、ジノクトン(dinocton)、ジノスルフォン(dinosulfon)、ジノテルボン(dinoterbon)、ジフェニルアミン（diphenylamine）、ジピリチオン（dipyrithione）、ジタリムホス（ditalimfos）、ジチアノン（dithianon）、ドデモルフ（dodemorph）、ドジン（dodine）、ドラゾクソロン（drazoxolon）、エデフェノホス（edifenphos）、エポキシコナゾール（epoxiconazole）、エタコナゾール（etaconazole）、エタボキサム（ethaboxam）、エテム(etem)、エチリモル（ethirimol）、エトキシキン(ethoxyquin)、エトリジアノール（etridiazole）、ファモキサゾン（famoxadone）、フェナリモル（fenarimol）、フェブコナゾール（febuconazole）、フェナミドン（fenamidone）、フェナミノスルフ(fenaminosulf)、フェナパニル(fenapanil)、フェンダゾスラム(fendazosulam)、フェンフラム（fenfuram）、フェンヘキサミド（fenhexamid）、フェニトロパン(fenitropan)、フェノキサニル(fenoxanil)、フェンピクロニル（fenpiclonil）、フェンプロピジン（fenpropidin）、フェンピラザミン(fenpyrazamine)、フェンプロピモルフ（fenpropimorph）、フェンチン（fentin）、フェルバン（ferbam）、フェリムゾン（ferimzone）、フルアジナム（fluazinam）、フルジオキソニル（fludioxonil）、フルメトベル(flumetover)、フルモルフ(flumorph)、フルオピコリド（fluopicolide）、フルオピラム（fluopyram）、フルオロイミド（fluoroimide）、フルオトリマゾール(fluotrimazole)、フルオキサストロビン(fluoxastrobin)、フルキンコナゾール（fluquinconazole）、フルシラゾール（flusilazole）、フルスルファミド（flusulfamide）、フルチアニル（flutianil）、フルトラニル（flutolanil）、フルトリアフォール（flutriafol）、フルキサピロキサド（fluxapyroxad）、フォルペット（folpet）、フォセチル－アルミニウム（fosetyl-aluminium）、フベリダゾール（fuberidazole）、フララキシル（furalaxyl）、フラメトピル(furametpyr)、フルカルバニル(furcarbanil)、フルコナゾール(furconazole)、フルコナゾール－シス(furconazole-cis)、フルメシクロックス(furmecyclox)、フルファネート(furphanate)、グリオジン(glyodin)、グリセオフルビン(griseofulvin)、グアザチン（guazatine）、ハラクリネイト(halacrinate)、ヘキサクロロベンゼン（hexachlorobenzene）、ヘキサコナゾール（hexaconazole）、ヘキシルチオフォス(hexylthiofos)、ハイドロキシキノリン　サルフェイト(8-hydroxyquinoline sulfate)、ヒメキサゾール（hymexazol）、イマザリル（imazalil）、イミベンコナゾール（imibenconazole）、イミノクタジン（iminoctadine）、イプコナゾール（ipconazole）、イプロベンホス（iprobenfos）、イプロジオン（iprodione）、イプロバリカルブ（iprovalicarb）、イソプロチオラン（isoprothiolane）、イソバレジオン(isovaledione)等。 Bactericides (continued): diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole-, diniconazole-M M), dinobuton, dinocap, dinocap-4, dinocap-6, dinoton, dinosulfon, dinoterbon, diphenylamine ), Dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos, epoxiconazole, ethaconazole, etaconazole Boxaam, etem, etirimol, ethoxyquin, etridiazole, famoxadone, fenarimol, febuconazole, fenamidone, sulfaminosulfen ), Fenapanil, fendazosulam, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpyrazamine (fenpyrazamine), fenpropimorph, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, flumorph Opicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, fluthianyl (fluthanil) flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fuberidazole, fluralaxyl, flametopir ( furametpyr), furcarbanil, furconazole, fluconazole-cis, furmecyclox, furphanate, glyodin, griseofulvin, guaza Guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, hydroxyquinoline sulfate (hymexazol), imazalil Imibenconazole, iminoctadine, ipconazole, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isovaledione, etc.
　殺菌剤（続き）：カスガマイシン（kasugamycin）、クレソキシム－メチル（kresoxim-methyl）、マンカッパー（mancopper）、マンコゼブ（mancozeb）、マンジプロパミド（mandipropamid）、マンネブ（maneb）、メベニル（mebenil）、メカルビンジド（mecarbinzid）、メパニピリム（mepanipyrim）、メプロニル（mepronil）、メタラキシル（metalaxyl）、メタラキシル－Ｍ（metalaxyl-M）、メタム（metam）、メタゾキソロン（metazoxolon）、メトコナゾール（metconazole）、メタスルホカルブ(methasulfocarb)、メトフロキサム（methfuroxam）、メチルイソチオシアネイト（methyl isothiocyanate）、メチラム（metiram）、メトミノストロビン（metominostrobin）、メトラフェノン（metrafenone）、メトスルフォバックス（metsulfovax）、ミルネブ（milneb）、ミクロブタニル（myclobutanil）、ミクロゾリン（myclozolin）、ナバム（nabam）、ナタマイシン（natamycin）、ニッケルビス（ジメチルジチオカーバメート）（nickel bis(dimethyldithiocarbamate)）、ニトロスチレン（nitrostyrene）、ニトロタール－イソプロピル（nitrothal-isopropyl）、ヌアリモル（nuarimol）、オーシーエイチ（OCH）、オクチリノン（octhilinone）、オフレース（ofurace）、オリサストロビン（orysastrobin）、オキサジキシル（oxadixyl）、有機銅（oxine copper）、オキシカルボキシン（oxycarboxin）、オキスポコナゾールフマール酸塩（oxpoconazole fumarate）、ペフラゾエート（pefurzoate）、ペンコナゾール（penconazole）、ペンフルフェン（penflufen）、ペンシクロン（pencycuron）、ペンチオピラド（penthiopyrad）、オルソフェニルフェノール（o-phenylphenol）、フォスジフェン（phosdiphen）、フタライド（phthalide）、ピコキシストロビン（picoxystrobin）、ピペラリン（piperalin）、ポリカーバメート（polycarbamate）、ポリオキシン（polyoxins）、ポリオクソリム（polyoxorim）、ポタシウムアザイド（potassium azide）、炭酸水素カリウム(potassium hydrogen carbonate)、プロキナジド（proquinazid）、プロベナゾール（probenazole）、プロクロラズ（prochloraz）、プロシミドン（procymidone）、プロパモカルブ塩酸塩（propamocarb hydrochloride）、プロピコナゾール（propiconazole）、プロピネブ（propineb）、プロチオカルブ（prothiocarb）、プロチオコナゾール（prothioconazole）、ピラカルボリド（pyracarbolid）、ピラクロストロビン（pyraclostrobin）、ピラゾホス（pyrazophos）、ピリジニトリル（pyridinitril）、ピリフェノックス（pyrifenox）、ピリメタニル（pyrimethanil）、ピリオフェノン（pyriofenone）、ピロキュロン（pyroquilon）、ピロキシクロル（pyroxychlor）、ピロキシフル（pyroxyfur）、キノメチオネート(quinomethionate)、キノキシフェン（quinoxyfen）、キントゼン（quintozene）、キナセトール・スルフェート（quinacetol-sulfate）、キナザミド（quinazamid）、キンコナゾール（quinconazole）、ラベンザゾール（rabenzazole）等。 Fungicide (continued): kasugamycin, kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid , Mepanipyrim, mepronil, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, metoxafloxam ), Methylisothiocyanate, metiram, metinominostrobin, metrafenone, metsulfovax, milneb, microbutanil, microzoline (myc) lozolin, nabam, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, OH (OCH), octhilinone, offurace, orysastrobin, oxadixyl, organic copper (oxine copper), oxycarboxin, oxpoconazole fumarate , Pefurzoate, penconazole, penflufen, penencycuron, penthiopyrad, o-phenylphenol, phosdiphen, phthalide, picoki Cistrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, proquinazid, proquinazid probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb, prothiocarb, prothioconazole, pyracarbolid, Pyraclostrobin, pyrazophos, pyridinitril, pyrifenox, pyrimethanil, pyriofenone, piroculo Pyroquilon, pyroxychlor, pyroxyfur, quinomethionate, quinoxyfen, quintozene, quinacetol-sulfate, quinazamid, quinazamid, quinconazole, quinconazole Rabenzazole and the like.
　殺菌剤（続き）：アジ化ナトリウム（sodium azide）、炭酸水素ナトリウム(sodium hydrogen carbonate)、次亜塩素酸ナトリウム(sodium hypochlorite)、硫黄（sulfur）、スピロキサミン（spiroxamine）、サリチルアニリド（salycylanilide）、シルチオファム（silthiofam）、シメコナゾール（simeconazole）、テブコナゾール（tebuconazole）、テクナゼン（tecnazene）、テコラム（tecoram）、テトラコナゾール（tetraconazole）、チアベンダゾール（thiabendazole）、チアジフルオール（thiadifluor）、チシオフェン（thicyofen）、チフルザミド（thifluzamide）、チオクロルフェンフィム（thiochlorfenphim）、チオファネート（thiophanate）、チオファネート－メチル（thiophanate-methyl）、チオキノックス（thioquinox）、チラム（thiram）、チアジニル（tiadinil）、チオキシミド（tioxymid）、トルクロホス－メチル（tolclofos-methyl）、トリルフラニド（tolylfluanid）、トリアジメホン（triadimefon）、トリアジメノール（toriadimenol）、トリアミフォス（triamiphos）、トリアリモル（triarimol）、トリアゾキシド（triazoxide）、トリアズブチル（triazbutil）、トリブチルチンオキサイド（tributyltin oxide）、トリクラミド（trichlamide）、トリシクラゾール（tricyclazole）、トリデモルフ（tridemorph）、トリフロキシストロビン(trifloxystrobin)、トリフルミゾール（triflumizole）、トリホリン（triforine）、トリチコナゾール（triticonazole）、バリダマイシン（validamycin）、バリフェナレート（valifenalate）、ビンクロゾリン（vinclozolin）、ザリルアミド（zarilamide）、硫酸亜鉛(zinc sulfate)、ジネブ（zineb）、ジラム（ziram）、ゾキサミド（zoxamide）及びシイタケ菌糸体抽出物等。 Bactericides (continued): sodium azide, sodium hydrogen carbonate, sodium hypochlorite, sulfur, spiroxamine, salicylanilide, silthiofam (Silthiofam), simeconazole, tebuconazole, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thioquinox, thiram, thiadinyl, tioxymid, tolcrofos -Tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazoxide, triazbutil, tributyltin oxide oxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, Varifenalate, vinclozolin, zarilamide, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract and the like.
　殺バクテリア剤：ベンザルコニウムクロライド(benzalkonium chloride)、ビチオノール(bithionol)、ブロノポール（bronopol）、クレゾール(cresol)、ホルムアルデヒド（formaldehyde）、ニトラピリン（nitrapyrin）、オキソリニックアシド（oxolinic acid）、オキシテトラサイクリン（oxyterracycline）、ストレプトマイシン（streptomycin）及びテクロフタラム(tecloftalam)等。
　殺線虫剤：アルドキシカルブ（aldoxycarb）、カズサホス（cadusafos）、デービーシーピー(DBCP)、ジクロフェンチオン（dichlofenthion）、デーエスピー（DSP）、エトプロホス（ethoprophos）、フェナミホス（fenamiphos）、フェンスルホチオン（fensulfothion）、フルエンスルホン(fluensulfone)、フォスチアゼート（fosthiazate）、フォスチエタン（fosthietan）、イミシアホス（imicyafos）、イサミドホス（isamidofos）、イサゾホス（isazofos）、オキサミル（oxamyl）及びチオナジン（thionazin）等。
　殺ダニ剤：アセキノシル（acequinocyl）、アクリナトリン（acrinathrin）、アミトラズ（amitraz）、ＢＣＩ－０３３（試験名）、ビフェナゼート（bifenazate）、ブロモプロピレート（bromopropylate）、チノメチオネート（chinomethionat）、クロロベンジラート（chlorobezilate）、クロフェンテジン（clofentezine）、シエノピラフェン（cyenopyrafen）、シフルメトフェン（cyflumetofen）、サイヘキサチン（cyhexatine）、ジコフォール（dicofol）、ジエノクロール（dienochlor）、デーエヌオーシー(DNOC)、エトキサゾール（etoxazole）、フェナザキン（fenazaquin）、フェンブタチンオキシド（fenbutatin oxide）、フェノチオカルブ（fenothiocarb）、フェンプロパトリン（fenpropathrin）、フェンピロキシメート（fenpyroximate）、フルアクリピリム（fluacrypyrim）、ハルフェンプロックス（halfenprox）、ヘキシチアゾックス（hexythiazox）、ミルベメクチン（milbemectin）、プロパルギット（propargite）、ピフルブミド（pyflubumide）、ピリダベン（pyridaben）、ピリミジフェン（pyrimidifen）、Ｓ－１８７０（試験名）、スピロジクロフェン（spirodiclofen）、スピロメシフェン（spyromesifen）、ＣＬ９００１６７（試験名）及びテブフェンピラド（tebufenpyrad）等。 Bactericides: benzalkonium chloride, bithionol, bronopol, cresol, formaldehyde, nitrapyrin, oxolinic acid, oxyterracycline , Streptomycin and tecloftalam.
Nematicides: aldoxycarb, cadusafos, DCP, DBCH, dichlofenthion, DSP (DSP), etoprophos, fenamiphos, fensulfothion, fluene Sulfone (fluensulfone), fosthiazate (fosthiazate), fosthietan (fosthietan), imisiafos (imicyafos), isamidofos (isamidofos), isazofos (isazofos), oxamyl (oxamyl) and thionazin (thionazin) and the like.
Acaricides: acequinocyl, acrinathrin, amitraz, BCI-033 (test name), bifenazate, bromopropylate, chinomethionat, chlorobezilate , Clofentezine, cyenopyrafen, cyflumetofen, cyhexatine, dicofol, dienochlor, denochlor (DNOC), etoxazole, quinazaquin (fenaza) Fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fluacrypyrim, halfenprox (halfenpro) x), hexythiazox, milbemectin, propargite, pyflubumide, pyridaben, pyrimidifen, S-1870 (test name), spirodiclofen , Spyromesifen, CL900167 (test name), tebufenpyrad and the like.
　殺虫剤：アバメクチン（abamectin）、アセフェート（acephate）、アセタミピリド（acetamipirid）アフィドピロペン（afidopyropen）、アラニカルブ（alanycarb）、アルディカルブ（aldicarb）、アレスリン（allethrin）、アザメチホス(azamethiphos)、アジンホス－メチル（azinphos-methyl）、バチルスチューリンゲシス（bacillus thuringiensis）、ベンジオカルブ（bendiocarb）、ベンフルトリン(benfluthrin)、ベンフラカルブ（benfuracarb）、ベンスルタップ（bensultap）、ビフェントリン（bifenthrin）、ビオアレスリン(bioallethrin)、ビオレスメトリン(bioresmethrin)、ビストリフルロン(bistrifluron)、ブプロフェジン（buprofezin）、ブトカルボキシン（butocarboxim）、カルバリル（carbaryl）、カルボフラン（carbofuran）、カルボスルファン（carbosulfan）、カルタップ（cartap）、クロルアントラニリプロール（chlorantraniliprole）、クロルエトキシホス(chlorethxyfos)、クロルフェナピル（chlorfenapyr）、クロルフェンビンホス（chlorfenvinphos）、クロルフルアズロン（chlorfluazuron）、クロルメホス(chlormephos)、クロルピリホス（chlorpyrifos）、クロピリホス－メチル（chlorpyrifos-methyl）、クロマフェノジド（chromafenozide）、クロチアニジン（clothianidin）、シアントラニリプロール(cyantraniliprole)、シクロプロトリン（cycloprothrin）、シフルメトフェン（cyflumetofen）、シフルトリン（cyfluthrin）、ベータ－シフルトリン（beta-cyfluthrin）、シハロトリン（cyhalothrin）、ラムダ－シハロトリン（lambda-cyhalothrin）、シペルメトリン（cypermethrin）、アルファ－シペルメトリン（alpha-cypermethrin）、ベータ－シペルメトリン（beta-cypermethrin）、ゼタ－シペルメトリン（zeta-cypermethrin）、シロマジン（cyromazine）、デルタメトリン（deltamethrin）、ジアクロデン（diacloden）、ジアフェンチウロン（diafenthiuron）、ダイアジノン（diazinon）、ジクロルボス（dichlorvos）、ジフルベンズロン（diflubenzuron）、ジメチルビンホス（dimethylvinphos）、ジノテフラン（dinotefuran）、ジオフェノラン（diofenolan）、ジスルフォトン（disulfoton）、ジメトエート（dimethoate）、エマメクチンベンゾエート（emamectin-benzoate）、エンペントリン（empenthrin）、エンドスルファン（endosulfan）、アルファ－エンドスルファン（alpha-endosulfan）、イーピーエヌ（EPN）、エスフェンバレレート（esfenvalerate）、エチオフェンカルブ（ethiofencarb）、エチプロール（ethiprole）、エトフェンプロックス（etofenprox）、エトリムホス（etrimfos）、フェニトロチオン（fenitrothion）、フェノブカルブ（fenobucarb）、フェノキシカーブ（fenoxycarb）、フェンプロパトリン（fenpropathrin）、フェンチオン（fenthion）、フェンバレレート（fenvalerate）、フィプロニル（fipronil）、フロニカミド（flonicamid）、フルベンジアミド（flubendiamide）、フルシトリネート（flucythrinate）、フルフェネリム（flufenerim）、フルフェノクスウロン（flufenoxuron）、フルフェンプロックス（flufenprox）、フルメトリン（flumethrin）、フルバリネート（fluvalinate）、タウ－フルバリネート（tau-fluvalinate）、ホノホス（fonophos）、フォルメタネート（formetanate）、フォルモチオン（formothion）、フラチオカルブ（furathiocarb）、フルフィプロール(flufiprole)、フルピラジフロン(flupyradifurone)、フロメトキン(flometoquin)等。 Insecticides: abamectin, acephate, acetamipirid afidopyropen, alanidocarb, aldicarb, allethrin, azaphos-methyl, azine-methyl- ), Bacillus thuringiensis, bendiocarb, benfluthrin, benfuracarb, bensultap, bifenthrin, bioallethrin, violesmethrin, bioresmethrin (bistrifluron), buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chloranthra Chlorantraniliprole, chlorethxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos-methyl ), Chromafenozide, clothianidin, cyantraniliprole, cycloprothrin, cyflumetofen, cyfluthrin, beta-cyfluthrin, halothrin , Lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cyperm ethrin, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethylvinphos, dinotefuran ( dinotefuran, diofenolan, disulfoton, dimethoate, emamectin-benzoate, empenthrin, endosulfan, alpha-endosulfan, alpha-endosulfan, EPN, Esfenvalerate, ethiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, Fenobucarb, fenoxycarb, fenpropathrin, fenthion, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate ), Flufenerim, flufenoxuron, flufenprox, flumethrin, fluvalinate, tau-fluvalinate, fonophos, formethanate (Formetanate), formothion, furathiocarb, flufiprole, flupyradifurone, flometoquin and the like.
　殺虫剤（続き）：ハロフェノジド（halofenozide）、ヘキサフルムロン（hexaflumuron）、ヒドラメチルノン（hydramethylnon）、イミダクロプリド（imidacloprid）、イソフェンホス（isofenphos）、インドキサカルブ（indoxacarb）、イソプロカルブ（isoprocarb）、イソキサチオン（isoxathion）、レピメクチン（lepimectin）、ルフェヌウロン（lufenuron）、マラチオン（malathion）、メペルフルスリン（meperfluthrin）、メタフルミゾン（metaflumizone）、メタルデヒド（metaldehyde）、メタミドホス（methamidophos）、メチダチオン（methidathion）、メタクリホス（methacrifos）、メタフルミゾン（metaflumizone）、メタルカルブ（metalcarb）、メソミル（methomyl）、メソプレン（methoprene）、メトキシクロール（methoxychlor）、メトキシフェノジド（methoxyfenozide）、メチルブロマイド（methyl bromide）、モノクロトホス（monocrotophos）、ムスカルーレ（muscalure）、ニテンピラム（nitenpyram）、ノバルロン（novaluron）、ノビフルムロン（noviflumuron）、オメトエート（omethoate）、オキサミル（oxamyl）、オキシデメトン－メチル（oxydemeton-methyl）、オキシデプロホス（oxydeprofos）、パラチオン（parathion）、パラチオン－メチル（parathion-methyl）、ペンタクロロフェノール（pentachlorophenol(PCP)）、ペルメトリン（permethrin）、フェノトリン（phenothrin）、フェントエート（phenthoate）、フォキシム（phoxim）、ホレート（phorate）、ホサロン（phosalone）、ホスメット（phosmet）、ホスファミドン（phosphamidon）、ピリミカルブ（pirimicarb）、ピリミホス－メチル（pirimiphos-methyl）、プロフェノホス（profenofos）、プロチオホス（prothiofos）、プロパホス（propaphos）、プロトリフェンブト（protrifenbute）、ピメトロジン（pymetrozine）、ピラクロホス（pyraclofos）、ピレトリン（pyrethrins）、ピリダリル（pyridalyl）、ピリフルキナゾン（pyrifluquinazon）、ピリプロール（pyriprole）、ピラフルプロール(pyrafluprole)、ピリプロキシフェン（pyriproxyfen）、レスメトリン（resmethrin）、ロテノン（rotenone）、ＳＩ－０４０５（試験名）、スルプロホス（sulprofos）、シラフルオフェン（silafluofen）、スピネトラム（spinetoram）、スピノサド（spinosad）、スピロテトラマート（spirotetramat）、スルホキサフロール(sulfoxaflor)、スルホテップ（sulfotep）、ＳＹＪ－１５９（試験名）、テブフェノジド（tebfenozide）、テフルベンズロン（teflubenzuron）、テフルトリン（tefluthorin）、テルブホス（terbufos）、テトラクロロビンホス（tetrachlorvinphos）、テトラメトリン（tetramethrin）、ｄ－Ｔ－８０－フタルスリン（d-tetramethrin）、テトラメチルフルスリン（tetramethylfluthrin）、チアクロプリド（thiacloprid）、チオシクラム（thiocyclam）、チオジカルブ（thiodicarb）、チアメトキサム（thiamethoxam）、チオファノックス（thiofanox）、チオメトン（thiometon）、トルフェンピラド（tolfenpyrad）、トラロメスリン（tralomethrin）、トリクロルホン（trichlorfon）、トリアズロン（triazuron）、トリフルムロン（triflumuron）、バミドチオン（vamidothion）、ＭＥ－５３８２（試験名）、ＺＤＩ２５０１又はＮＡ－８９等。 Insecticides (continued): halofenozide, hexaflumuron, hydramethylnon, imidacloprid, isofenphos, indoxacarb, isoprocarb, isoxathion ), Lepimectin, lufenuron, malathion, meperfluthrin, metaflumizone, metalaldehyde, methamidophos, methidathion, methidathion, methacrifos (methacrifos) ), Metalcarb, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromi de), monocrotophos, muscalure, nitenpyram, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeproton Phos (oxydeprofos), parathion, parathion-methyl, pentachlorophenol (PCP), permethrin, phenothrin, phenthoate, phoxim, folate (Phorate), phosalone, phosmet, phosphamidon, pirimicarb, pirimiphos-methyl, profenofos, prothiofos, propaphos, pro Protrifenbute, Pymetrozine, Pyraclofos, Pyrethrins, Pyridalyl, Pyrifluquinazon, Pyriprole, Pirafluprole, Pyriprofen, Pyriprox (Resmethrin), rotenone, SI-0405 (study name), sulprofos, silafluofen, spinetoram, spinosad, spirotetramat, sulfoxaflor , Sulfotep, SYJ-159 (test name), tebfenozide, teflubenzuron, tefluthorin, terbufos, tetrachlorvinphos, tetra Trimethrin, dT-80-phthalthrin (d-tetramethrin), tetramethylfluthrin, thiacloprid, thiocyclam, thiodicarb, thiamethoxam, thiophanox ( thiofanox, thiometon, tolfenpyrad, tralomethrin, trichlorfon, triazuron, triflumuron, vamidomion, ME-5382 (test name), ZDI2501 or NA- 89 mag.
　以下に本発明化合物の合成例、試験例を実施例として具体的に記載し、本発明をさらに詳しく説明するが、本発明はこれらによって限定して解釈されるものではない。
　合成例に記載した中圧分取液体クロマトグラフィーは、山善社製、中圧分取装置；ＹＦＬＣ－Ｗｐｒｅｐ（流速１８ｍｌ／ｍｉｎ、シリカゲル４０μｍのカラム）を使用した。また、高速分取液体クロマトグラフィーは、以下の条件で、島津製作所社製；１０ＡＶＰシステムを使用した。
　オーブン温度：４０℃
　移動相：アセトニトリル７ｍｌ/ｍｉｎ.，水４ｍｌ/ｍｉｎ.
　カラム：ＧＬサイエンス　Ｉｎｅｒｔｓｉｌ－ＯＤＳ３（内径２０ｍｍ、長さ２５０ｍｍ、粒子径５μｍ）、
　測定波長：２５４ｎｍ
　また、旋光度の測定には、日本分光社製（ＪＡＳＣＯ）のＰ－１０２０を使用した。
　１Ｈ　ＮＭＲの測定は、日本電子社製のＪＮＭ－ＥＣＸ３００を用いて行った。 Synthesis examples and test examples of the compounds of the present invention will be specifically described below as examples, and the present invention will be described in more detail. However, the present invention is not construed as being limited thereto.
The medium pressure preparative liquid chromatography described in the synthesis example used an intermediate pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column). Moreover, the high performance preparative liquid chromatography used Shimadzu Corporation 10AVP system on the following conditions.
Oven temperature: 40 ° C
Mobile phase: acetonitrile 7 ml / min., Water 4 ml / min.
Column: GL Science Inertsil-ODS3 (inner diameter 20 mm, length 250 mm, particle diameter 5 μm),
Measurement wavelength: 254 nm
For measurement of optical rotation, P-1020 manufactured by JASCO (JASCO) was used.
1 H NMR measurement was performed using JNM-ECX300 manufactured by JEOL.
　　合成例１
　Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－（ヒドロキシイミノ）プロパンアミド（本発明化合物１－００３）の製造
　工程１：ｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イルカーバメートの製造
　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸２．４０ｇの２－メチル－２－プロパノール２０ｍｌ溶液に、室温にてトリエチルアミン２．４５ｇ及びジフェニルホスホリルアジド２．００ｇを順次添加した。添加終了後、２－メチル－２－プロパノールを還流させながら４時間撹拌した。反応終了後、該反応混合物を室温まで放冷した後、氷水に注ぎ、酢酸エチル５０ｍｌにて抽出した。得られた有機層を、無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル［１：１（体積比、以下同じである）］にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．８６ｇを白色固体として得た。
融点；１２５－１２８℃。
　工程２：ｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル（エチル）カーバメートの製造
　６０重量％水素化ナトリウム（鉱油中に分散）０．１５ｇのＮ，Ｎ－ジメチルホルムアミド１０ｍｌ溶液に、氷冷下にてｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イルカーバメート０．９５ｇを添加した。添加終了後、室温まで昇温し、同温度にて３０分間撹拌した。攪拌終了後、該反応混合物にヨウ化エチル０．５５ｇを添加し、室温にて１時間撹拌を継続した。反応終了後、該反応混合物を氷水に注ぎ、酢酸エチル１００ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムにて脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（２：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１．０６ｇを黄色固体として得た。
融点；５５－５８℃ Synthesis example 1
Production of N- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (hydroxyimino) propanamide (present compound 1-003) Step 1 Preparation of tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-ylcarbamate 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid To a 40 ml solution of 2.40 g of 2-methyl-2-propanol, 2.45 g of triethylamine and 2.00 g of diphenylphosphoryl azide were sequentially added at room temperature. After completion of the addition, the mixture was stirred for 4 hours while refluxing 2-methyl-2-propanol. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into ice water, and extracted with 50 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate [1: 1 (volume ratio, the same shall apply hereinafter)], and 0.86 g of the desired product was obtained as a white solid. Got as.
Melting point: 125-128 ° C.
Step 2: Preparation of tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl (ethyl) carbamate 60 wt% sodium hydride (dispersed in mineral oil) 0.15 g N , N-dimethylformamide (10 ml) was mixed with 0.95 g of tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-ylcarbamate under ice-cooling. After completion of the addition, the temperature was raised to room temperature and stirred at the same temperature for 30 minutes. After the completion of stirring, 0.55 g of ethyl iodide was added to the reaction mixture, and stirring was continued at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water and extracted with 100 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (2: 1) to obtain 1.06 g of the desired product as a yellow solid.
Melting point: 55-58 ° C
　工程３：３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン　２塩酸塩の製造
　ｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル（エチル）カーバメート１．０ｇの１，４－ジオキサン２０ｍｌ溶液に、約４Ｍ塩化水素の１，４－ジオキサン溶液８．１ｍｌを添加した。添加終了後、室温にて１２時間撹拌した。反応終了後、該反応溶液中に析出した固体を減圧下濾過にて取り出した。減圧下乾燥した後、目的物０．８５ｇを白色固体として得た。
融点；１３２－１３３℃
　工程４：３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造
　１Ｎ水酸化ナトリウム水溶液７．４ｍｌに、３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン　２塩酸塩１ｇを添加した。添加終了後、室温にて３時間撹拌した。反応終了後、該反応混合物をジクロロメタン２０ｍｌ（ｘ３）にて抽出した。得られた有機層を無水硫酸ナトリウムで乾燥後、減圧下にて溶媒を留去し、目的物６６０ｍｇを白色固体として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，内部標準はＭｅ４Ｓｉ，３００ＭＨｚ）δ８．８６（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．４６（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．００－７．９０（ｍ，１Ｈ），７．４５（ｄｄｄ，Ｊ＝８．１，４．８，１．２Ｈｚ，１Ｈ），７．３３（ｓ，１Ｈ），３．０１（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），３．００（ｂｒｓ，１Ｈ），１．３１（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
融点；８９－９０℃ Step 3: Preparation of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine dihydrochloride tert-butyl 3-chloro-1- (pyridin-3-yl)- To a 20 ml 1,4-dioxane solution of 1.0 g of 1H-pyrazol-4-yl (ethyl) carbamate was added 8.1 ml of a 1,4-dioxane solution of about 4M hydrogen chloride. After completion of the addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solid precipitated in the reaction solution was removed by filtration under reduced pressure. After drying under reduced pressure, 0.85 g of the desired product was obtained as a white solid.
Melting point: 132-133 ° C
Step 4: Preparation of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine To 7.4 ml of 1N aqueous sodium hydroxide solution, 3-chloro-N-ethyl-1- 1 g of (pyridin-3-yl) -1H-pyrazol-4-amine dihydrochloride was added. After completion of the addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was extracted with 20 ml (x3) of dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 660 mg of the desired product as a white solid.
1 H NMR (CDCl 3 , internal standard is Me 4 Si, 300 MHz) δ 8.86 (d, J = 2.7 Hz, 1H), 8.46 (dd, J = 4.8, 1.2 Hz, 1H), 8.00-7.90 (m, 1H), 7.45 (ddd, J = 8.1, 4.8, 1.2 Hz, 1H), 7.33 (s, 1H), 3.01 (q , J = 7.2 Hz, 2H), 3.00 (brs, 1H), 1.31 (t, J = 7.2 Hz, 3H)
Melting point: 89-90 ° C
　工程５：Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－オキソプロパンアミドの製造
　３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン１ｇのジクロロメタン１０ｍｌ溶液に、室温にてピルビン酸０．５９ｇ、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩１．７ｇ及び４－ジメチルアミノピリジン３ｍｇを順次添加した。添加終了後、同温度にて１０分間撹拌した。反応終了後、該反応混合物に水１０ｍｌを添加し、ジクロロメタン２０ｍｌで抽出した。得られた有機層を、無水硫酸ナトリウムで乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１．４ｇを白色結晶として得た。
融点；７３－７７℃
　工程６：Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－（ヒドロキシイミノ）プロパンアミドの製造
　Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－オキソプロパンアミド４００ｍｇのエタノール５ｍｌ溶液に、トリエチルアミン１７９ｍｇ及び塩化ヒドロキシルアンモニウム１２３ｍｇを添加した。添加終了後、エタノールを還流させながら１時間撹拌した。反応終了後、該反応混合物より減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物２８７ｍｇを白色固体として得た。
融点；１４４-１４６℃ Step 5: Preparation of N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2-oxopropanamide 3-Chloro-N-ethyl-1- To a solution of 1 g of (pyridin-3-yl) -1H-pyrazol-4-amine in 10 ml of dichloromethane at room temperature is 0.59 g of pyruvic acid and 1.7 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. And 3 mg of 4-dimethylaminopyridine was added sequentially. After completion of the addition, the mixture was stirred at the same temperature for 10 minutes. After completion of the reaction, 10 ml of water was added to the reaction mixture and extracted with 20 ml of dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1) to obtain 1.4 g of the objective product as white crystals.
Melting point: 73-77 ° C
Step 6: Preparation of N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (hydroxyimino) propanamide N- {3-Chloro- To a solution of 400 mg of 1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2-oxopropanamide in 5 ml of ethanol was added 179 mg of triethylamine and 123 mg of hydroxylammonium chloride. After completion of the addition, the mixture was stirred for 1 hour while refluxing ethanol. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1) to obtain 287 mg of the desired product as a white solid.
Melting point: 144-146 ° C
　合成例２
Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－（メチルチオメトキシイミノ）プロパンアミド（本発明化合物１－００１）の製造
　Ｎ-｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－イル｝－Ｎ－エチル－２－（ヒドロキシイミノ）プロパンアミド１３８ｍｇのＮ，Ｎ－ジメチルホルムアミド１．５ｍｌ溶液に、氷冷下にて６０重量％水素化ナトリウム（鉱油中に分散）２１．５ｍｇを添加した。添加終了後、同温度にて３０分間撹拌した。攪拌終了後、該反応混合物に、クロロメチルメチルスルフィド５２ｍｇを添加した。添加終了後、室温にて５時間撹拌を継続した。反応終了後、該反応混合物に飽和塩化アンモニウム水溶液５ｍｌを添加し、酢酸エチル３０ｍｌにて抽出した。得られた有機層を、１Ｎ水酸化ナトリウム水溶液１０ｍｌ、水１０ｍｌの順で洗浄した後、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（４：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物７７ｍｇを白色固体として得た。
融点；９２－９５℃ Synthesis example 2
Production of N- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methylthiomethoxyimino) propanamide (present compound 1-001) N -{3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (hydroxyimino) propanamide in 138 mg of N, N-dimethylformamide in 1.5 ml solution Under ice cooling, 21.5 mg of 60 wt% sodium hydride (dispersed in mineral oil) was added. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the stirring, 52 mg of chloromethyl methyl sulfide was added to the reaction mixture. After completion of the addition, stirring was continued for 5 hours at room temperature. After completion of the reaction, 5 ml of a saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with 30 ml of ethyl acetate. The obtained organic layer was washed with 10 ml of a 1N aqueous sodium hydroxide solution and 10 ml of water in that order, then dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (4: 1 to 1: 1 gradient) to obtain 77 mg of the desired product as a white solid.
Melting point: 92-95 ° C
　合成例３
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド（本発明化合物１－０５７）の製造
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸１．４２ｇのジクロロメタン１０ｍｌ溶液に、室温にてオキサリルクロリド１．３８ｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、同温度にて２時間撹拌した。反応終了後、減圧下にて溶媒を留去し、得られた残留物を、別途調製した３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン１．４２ｇ及びピリジン１．４４ｇのジクロロメタン２０ｍｌ溶液に添加した。添加終了後、室温にて３０分間撹拌した。反応終了後、該反応溶液を水１０ｍｌで洗浄した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．６ｇを白色固体として得た。
融点；８０－８２℃ Synthesis example 3
Production of N- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide (present compound 1-057) 2 To a solution of 1.42 g of-(methoxyimino) -3- (methylthio) butanoic acid in 10 ml of dichloromethane was added 1.38 g of oxalyl chloride and then 10 mg of N, N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was separately prepared 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine 1 To a solution of .42 g and 1.44 g of pyridine in 20 ml of dichloromethane. After completion of the addition, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was washed with 10 ml of water. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 0.6 g of the desired product as a white solid.
Melting point: 80-82 ° C
　合成例４
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－（シアノメチル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド（本発明化合物１－０５６）の製造
　６０重量％水素化ナトリウム（鉱油中に分散）５４ｍｇのＮ，Ｎ－ジメチルホルムアミド５ｍｌ溶液に、氷冷下にてＮ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド４００ｍｇを添加した。添加終了後、室温まで昇温し、同温度にて１時間撹拌した。攪拌終了後、該反応混合物にクロロアセトニトリル１０３ｍｇを添加し、更に室温にて一晩撹拌を継続した。反応終了後、該反応混合物を氷水に注ぎ、酢酸エチル１０ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムにて脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（３：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１２０ｍｇを黄色アモルファスとして得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９３（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６３（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．２０（ｓ，１Ｈ），８．０１（ｄｄｄ，Ｊ＝８．１，２．７，１．２Ｈｚ，１Ｈ），７．４６（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），４．７５（ｄ，Ｊ＝１７．４Ｈｚ，１Ｈ），４．５２（ｄ，Ｊ＝１７．４Ｈｚ，１Ｈ），４．１２（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），３．７６（ｓ，３Ｈ），１．９２（ｓ，３Ｈ）, １．５２（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ） Synthesis example 4
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N- (cyanomethyl) -2- (methoxyimino) -3- (methylthio) butanamide (Compound 1 of the present invention) -056) 60% by weight sodium hydride (dispersed in mineral oil) 54 mg of N, N-dimethylformamide solution in 5 ml of N- {3-chloro-1- (pyridin-3-yl) under ice-cooling 400 mg of -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide was added. After completion of the addition, the temperature was raised to room temperature and stirred at the same temperature for 1 hour. After stirring, 103 mg of chloroacetonitrile was added to the reaction mixture, and stirring was continued overnight at room temperature. After completion of the reaction, the reaction mixture was poured into ice water and extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1 to 1: 1 gradient) to obtain 120 mg of the objective product as yellow amorphous.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.93 (d, J = 2.7 Hz, 1H), 8.63 (dd, J = 4.8, 1.2 Hz, 1H), 8.20 (S, 1H), 8.01 (ddd, J = 8.1, 2.7, 1.2 Hz, 1H), 7.46 (dd, J = 8.1, 4.8 Hz, 1H), 4. 75 (d, J = 17.4 Hz, 1H), 4.52 (d, J = 17.4 Hz, 1H), 4.12 (q, J = 7.2 Hz, 1H), 3.76 (s, 3H) ), 1.92 (s, 3H), 1.52 (d, J = 7.2 Hz, 3H)
　合成例５
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド（本発明化合物１－０４１）の製造
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸０．４ｇのジクロロメタン５ｍｌ溶液に、室温にてオキサリルクロリド０．３９ｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、同温度にて２時間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物を、別途調製した３－クロロ－Ｎ－エチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン０．４６ｇ及びピリジン０．４１ｇのジクロロメタン５ｍｌ溶液に添加した。添加終了後、室温にて３０分間撹拌を継続した。反応終了後、該反応溶液を水１０ｍｌで洗浄した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．３５ｇを白色固体として得た。
融点；７２－７４℃ Synthesis example 5
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methoxyimino) -3- (methylthio) butanamide (Compound 1-041 of the present invention) ) To a solution of 0.4 g of 2- (methoxyimino) -3- (methylthio) butanoic acid in 5 ml of dichloromethane was added 0.39 g of oxalyl chloride and then 10 mg of N, N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was added to a separately prepared solution of 0.46 g of 3-chloro-N-ethyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine and 0.41 g of pyridine in 5 ml of dichloromethane. . After completion of the addition, stirring was continued at room temperature for 30 minutes. After completion of the reaction, the reaction solution was washed with 10 ml of water. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 0.35 g of the desired product as a white solid.
Melting point: 72-74 ° C
　合成例６
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルスルフィニル）ブタンアミド（本発明化合物１－０４２）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド１５３ｍｇの酢酸３ｍｌ溶液に、室温にて３０重量％過酸化水素水５６ｍｇを添加した。添加終了後、同温度にて１２時間撹拌した。反応終了後、該反応混合物に飽和亜硫酸水素ナトリウム水溶液１ｍｌを添加した後、減圧下にて溶媒を留去した。得られた残留物を酢酸エチル－メタノール（５：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１４５ｍｇを無色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は３：２であった。
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９３（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６３－８．５７（ｍ，１Ｈ），８．０７－７．９３（ｍ，１Ｈ），７．９６（ｓ，１Ｈ），７．４４（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），４．１９－４．０３（ｍ，１Ｈ），３．９３－３．６１（ｍ，２Ｈ）, ３．７５（ｓ，３Ｈ）, ２．５７（ｓ，３Ｈ）, １．５１（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）, １．３０－１．１５（ｍ，３Ｈ）
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９７（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．５８－８．５３（ｍ，１Ｈ），８．１５（ｓ，１Ｈ），８．０７－７．９３（ｍ，１Ｈ），７．４０（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），４．１９－４．０３（ｍ，１Ｈ），３．９３－３．６１（ｍ，２Ｈ）, ３．７２（ｓ，３Ｈ）, ２．５８（ｓ，３Ｈ）, １．４９（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）, １．３０－１．１５（ｍ，３Ｈ） Synthesis Example 6
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methoxyimino) -3- (methylsulfinyl) butanamide (present compound 1- 042) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methoxyimino) -3- (methylthio) butanamide 153 mg of acetic acid To 3 ml solution, 56 mg of 30 wt% hydrogen peroxide solution was added at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 12 hours. After completion of the reaction, 1 ml of a saturated aqueous sodium hydrogen sulfite solution was added to the reaction mixture, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with ethyl acetate-methanol (5: 1) to obtain 145 mg of the desired product as a colorless oil. The obtained target product was a mixture of two kinds of geometric isomers, and the isomer ratio was 3: 2.
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.93 (d, J = 2.7 Hz, 1H), 8.63-8.57 (m, 1H), 8.07-7.93 (m , 1H), 7.96 (s, 1H), 7.44 (dd, J = 8.1, 4.8 Hz, 1H), 4.19-4.03 (m, 1H), 3.93-3 .61 (m, 2H), 3.75 (s, 3H), 2.57 (s, 3H), 1.51 (d, J = 7.2 Hz, 3H), 1.30-1.15 (m , 3H)
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.97 (d, J = 2.7 Hz, 1H), 8.58-8.53 (m, 1H), 8.15 (s, 1H), 8.07-7.93 (m, 1H), 7.40 (dd, J = 8.1, 4.8 Hz, 1H), 4.19-4.03 (m, 1H), 3.93-3 .61 (m, 2H), 3.72 (s, 3H), 2.58 (s, 3H), 1.49 (d, J = 7.2 Hz, 3H), 1.30-1.15 (m , 3H)
　合成例７
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルスルホニル）ブタンアミド（本発明化合物１－００２）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド１５８ｍｇの酢酸３ｍｌ溶液に、室温にて３０重量％過酸化水素水５６ｍｇ及びタングステン酸ナトリウム二水和物８ｍｇを順次添加した。添加終了後、同温度にて１２時間撹拌した。反応終了後、該反応混合物に飽和亜硫酸水素ナトリウム水溶液１ｍｌを添加した後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１：１～０：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１６０ｍｇを白色固体として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は９２：８であった。
異性体比９２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．０２－８．９２（ｍ，１Ｈ），８．６３－８．５６（ｍ，１Ｈ），８．０９（ｓ，１Ｈ），８．０５－７．９４（ｍ，１Ｈ），７．４７－７．３８（ｍ，１Ｈ），４．６２（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），３．９５（ｄｑ，Ｊ＝１３．８，６．９Ｈｚ，１Ｈ）, ３．７７（ｓ，３Ｈ）, ３．５６（ｄｑ，Ｊ＝１３．８，６．６Ｈｚ，１Ｈ），２．９４（ｓ，３Ｈ）, １．７６（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）, １．３０－１．１９（ｍ，３Ｈ）
異性体比８
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．０２－８．９２（ｍ，１Ｈ），８．６３－８．５６（ｍ，１Ｈ），８．０９（ｓ，１Ｈ），８．０５－７．９４（ｍ，１Ｈ），７．４７－７．３８（ｍ，１Ｈ），４．９０－４．７８（ｍ，１Ｈ），３．９５（ｄｑ，Ｊ＝１３．８，６．９Ｈｚ，１Ｈ）, ３．７７（ｓ，３Ｈ）, ３．５６（ｄｑ，Ｊ＝１３．８，６．６Ｈｚ，１Ｈ），３．０２（ｓ，３Ｈ）, １．７６（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）, １．３０－１．１９（ｍ，３Ｈ） Synthesis example 7
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methoxyimino) -3- (methylsulfonyl) butanamide (the present compound 1- 002) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-ethyl-2- (methoxyimino) -3- (methylthio) butanamide 158 mg of acetic acid To a 3 ml solution, 56 mg of 30 wt% aqueous hydrogen peroxide and 8 mg of sodium tungstate dihydrate were sequentially added at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 12 hours. After completion of the reaction, 1 ml of a saturated aqueous sodium hydrogen sulfite solution was added to the reaction mixture, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1 to 0: 1 gradient) to obtain 160 mg of the desired product as a white solid. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 92: 8.
Isomer ratio 92
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.02-8.92 (m, 1H), 8.63-8.56 (m, 1H), 8.09 (s, 1H), 8. 05-7.94 (m, 1H), 7.47-7.38 (m, 1H), 4.62 (q, J = 7.2 Hz, 1H), 3.95 (dq, J = 13.8) , 6.9 Hz, 1 H), 3.77 (s, 3 H), 3.56 (dq, J = 13.8, 6.6 Hz, 1 H), 2.94 (s, 3 H), 1.76 (d , J = 7.2 Hz, 3H), 1.30-1.19 (m, 3H)
Isomeric ratio 8
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.02-8.92 (m, 1H), 8.63-8.56 (m, 1H), 8.09 (s, 1H), 8. 05-7.94 (m, 1H), 7.47-7.38 (m, 1H), 4.90-4.78 (m, 1H), 3.95 (dq, J = 13.8, 6 .9 Hz, 1 H), 3.77 (s, 3 H), 3.56 (dq, J = 13.8, 6.6 Hz, 1 H), 3.02 (s, 3 H), 1.76 (d, J = 7.2 Hz, 3H), 1.30-1.19 (m, 3H)
　合成例８
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド［本発明化合物１－０５７（＊３）］の製造
　合成例３で製造したＮ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド３．０ｇの酢酸１０ｍｌ溶液を、酢酸の還流温度で２時間撹拌した。反応終了後、減圧下溶媒を留去した。溶媒を留去した後に得られた残留物を、溶離液がｎ－へキサン：酢酸エチル＝７：３のシリカゲルカラムクロマトグラフィーで精製し、目的物０．３ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．４４（ｂｒｓ，１Ｈ），８．９８（ｄ，Ｊ＝２．４Ｈｚ，１Ｈ），８．７１（ｓ，１Ｈ），８．５５（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），７．９９（ｄｄｄ，Ｊ＝８．１，２．４，１．２Ｈｚ，１Ｈ），７．３９（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），４．１７－４．０１（ｍ，１Ｈ），４．０９（ｓ，３Ｈ），２．１０（ｓ，３Ｈ）, １．５２（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ） Synthesis example 8
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide [present compound 1-057 (* 3) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide prepared in Synthesis Example 3 A solution of 0 g of acetic acid in 10 ml was stirred at the reflux temperature of acetic acid for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue obtained after evaporation of the solvent was purified by silica gel column chromatography with an eluent of n-hexane: ethyl acetate = 7: 3 to obtain 0.3 g of the desired product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.44 (brs, 1H), 8.98 (d, J = 2.4 Hz, 1H), 8.71 (s, 1H), 8.55 ( dd, J = 4.8, 1.2 Hz, 1H), 7.9 (dddd, J = 8.1, 2.4, 1.2 Hz, 1H), 7.39 (dd, J = 8.1) 4.8 Hz, 1H), 4.17-4.01 (m, 1H), 4.09 (s, 3H), 2.10 (s, 3H), 1.52 (d, J = 7.2 Hz, 3H)
　合成例９
　エチル　２－｛（３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）（メチル）アミノ｝－Ｎ－メトキシ－２－オキソエタンイミドチオエート（本発明化合物１－０７８）の製造
　工程１：２－（エチルチオ）－２－（ヒドロキシイミノ）酢酸エチルの製造
　２－クロロ－２－（ヒドロキシイミノ)酢酸エチル１．０ｇのＮ，Ｎ－ジメチルホルムアミド１０ｍｌ溶液を０℃に冷却し、エチルメルカプタンナトリウム１．２２ｇを添加した。添加終了後、同温度で1時間撹拌した。反応終了後、該反応溶液に水２０ｍｌを添加し、酢酸エチル２０ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．９５ｇを無色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．８６（ｂｒｓ，１Ｈ），４．３４（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），３．０８（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ），１．３６（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ），１．２９（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　工程２：２－（エチルチオ）－２－（メトキシイミノ）酢酸エチルの製造
　２－（エチルチオ）－２－（ヒドロキシイミノ）酢酸エチル０．９５ｇのＮ，Ｎ－ジメチルホルムアミド１０ｍｌ溶液に、炭酸カリウム１．８５ｇ、ヨウ化メチル０．９３ｇを順次添加した。添加終了後、室温にて１時間撹拌した。反応終了後、該反応溶液に水１０ｍｌを添加した後、酢酸エチル１０ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（１０：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．６６ｇを無色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．３５（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．０７（ｓ，３Ｈ），３．００（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ），１．３６（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ），１．２７（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ） Synthesis Example 9
Ethyl 2-{(3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl) (methyl) amino} -N-methoxy-2-oxoethaneimidothioate (present compound 1- Step 1: Preparation of ethyl 2- (ethylthio) -2- (hydroxyimino) acetate A solution of 1.0 g of ethyl 2-chloro-2- (hydroxyimino) acetate in 10 ml of N, N-dimethylformamide at 0 ° C. The solution was cooled to 1.22 g of ethyl mercaptan sodium. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction solution and extracted with 20 ml of ethyl acetate. The obtained organic layer was washed with water, then washed and dried with saturated brine and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 0.95 g of the desired product as a colorless oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.86 (brs, 1H), 4.34 (q, J = 7.2 Hz, 2H), 3.08 (q, J = 7.5 Hz, 2H) ), 1.36 (t, J = 7.2 Hz, 3H), 1.29 (t, J = 7.5 Hz, 3H)
Step 2: Preparation of ethyl 2- (ethylthio) -2- (methoxyimino) acetate A solution of 0.95 g of ethyl 2- (ethylthio) -2- (hydroxyimino) acetate in 10 ml of N, N-dimethylformamide was added potassium carbonate 1 .85 g and methyl iodide 0.93 g were sequentially added. After completion of the addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction solution, followed by extraction with 10 ml of ethyl acetate. The obtained organic layer was washed with water, then washed and dried with saturated brine and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (10: 1) to obtain 0.66 g of the desired product as a colorless oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.35 (q, J = 7.2 Hz, 2H), 4.07 (s, 3H), 3.00 (q, J = 7.5 Hz, 2H ), 1.36 (t, J = 7.2 Hz, 3H), 1.27 (t, J = 7.5 Hz, 3H)
　工程３：２－（エチルチオ）－２－（メトキシイミノ）酢酸の製造
　２－（エチルチオ）－２－（メトキシイミノ）酢酸エチル０．６６ｇのエタノール５ｍｌ溶液に、１Ｎ　水酸化ナトリウム水溶液４．１ｍｌを添加した。添加終了後、室温にて３０分撹拌した。反応終了後、該反応溶液から減圧下にてエタノールを留去した。得られた残留物に１Ｎ　塩酸水溶液を添加してｐＨ２とした。酢酸エチル５ｍｌ（×２）にて抽出した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去して、目的物０．１２ｇを無色油状物として得た（異性対比～３：２）。
異性対比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．９５（ｓ，３Ｈ），２．８０（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ），１．３５（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
異性対比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．４８（ｓ，３Ｈ），２．９７（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），１．５２（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　工程４：エチル　２－｛（３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）（メチル）アミノ｝－Ｎ－メトキシ－２－オキソエタンイミドチオエートの製造
　２－（エチルチオ）－２－（メトキシイミノ）酢酸０．１２ｇのジクロロメタン５ｍｌ溶液に、室温にてオキサリルクロリド０．１３ｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、同温度にて１時間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物を、別途調製した３－クロロ－Ｎ－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン０．１４ｇ及びピリジン０．１３ｇのジクロロメタン１０ｍｌ溶液に添加した。添加終了後、室温にて一晩撹拌を継続した。反応終了後、該反応溶液を水１０ｍｌで洗浄した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（１：１）にて溶出する中圧分取液体クロマトグラフィーにて精製した後、更に高速分取液体クロマトグラフィーを用いて精製し、目的物１２ｍｇを白色固体として得た。
融点；１３５－１３８℃ Step 3: Preparation of 2- (ethylthio) -2- (methoxyimino) acetic acid 4.1 ml of 1N aqueous sodium hydroxide solution was added to a solution of 0.66 g of ethyl 2- (ethylthio) -2- (methoxyimino) acetate in 5 ml of ethanol. Added. After completion of the addition, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure. The resulting residue was adjusted to pH 2 by adding a 1N aqueous hydrochloric acid solution. After extraction with 5 ml (x2) of ethyl acetate, washing and drying were carried out in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.12 g of the desired product as a colorless oil. (Contrast to isomerism ~ 3: 2).
Contrast with sex 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.95 (s, 3H), 2.80 (q, J = 7.5 Hz, 2H), 1.35 (t, J = 7.5 Hz, 3H) )
Contrast 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.48 (s, 3H), 2.97 (q, J = 7.2 Hz, 2H), 1.52 (t, J = 7.2 Hz, 3H) )
Step 4: Preparation of ethyl 2-{(3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl) (methyl) amino} -N-methoxy-2-oxoethaneimidothioate 2 To a solution of 0.12 g of-(ethylthio) -2- (methoxyimino) acetic acid in 5 ml of dichloromethane was added 0.13 g of oxalyl chloride and then 10 mg of N, N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was added to a separately prepared solution of 0.14 g of 3-chloro-N-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine and 0.13 g of pyridine in 10 ml of dichloromethane. . After the addition was complete, stirring was continued overnight at room temperature. After completion of the reaction, the reaction solution was washed with 10 ml of water. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1), and further purified using high performance preparative liquid chromatography to obtain the desired product. 12 mg was obtained as a white solid.
Melting point: 135-138 ° C
　合成例１０
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミド（本発明化合物１－０３２）の製造
　合成例８と同様の方法を用いて製造した。
融点；１０８－１１２℃ Synthesis Example 10
Production of N- {3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) propanamide (the present compound 1-032) It was produced using the same method as in Synthesis Example 8.
Melting point: 108-112 ° C
　合成例１１
　［Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミド］メチル　アセテート（本発明化合物１－０７３）及び〈１－［｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝イミノ］－２－（メトキシイミノ）－３－(メチルチオ)プロポキシ〉メチル　アセテート（本発明化合物４－００１）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミド５００ｍｇのＮ，Ｎ－ジメチルホルムアミド２ｍｌ溶液に、０℃にて６０重量％水素化ナトリウム（鉱油中に分散）８８．４ｍｇを添加し、２０分間撹拌した。攪拌終了後、該反応溶液に、酢酸ブロモメチル３３８ｍｇを添加し、室温にて２時間撹拌を継続した。反応終了後、該反応溶液を氷水に注ぎ、酢酸エチル５０ｍｌにて抽出した。得られた有機層を水洗（５０ｍｌ×２）した後、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（５：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、〈１－［｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝イミノ］－２－（メトキシイミノ）－３－(メチルチオ)プロポキシ〉メチル　アセテート７４．２ｍｇを白色結晶として、［Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミド］メチル　アセテート３０２ｍｇを黄色油状物として得た。
　［Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミド］メチル　アセテート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９０（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６１（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．１０－７．９０（ｍ，２Ｈ）,７．４４（ｄｄ，Ｊ＝８．４，４．８Ｈｚ，１Ｈ），５．８０－５．６０（ｂｒｓ，２Ｈ），３．９０－３．６０（ｂｒｓ，３Ｈ），３．５７（ｓ，２Ｈ），２．１１（ｓ，３Ｈ），２．０５－１．８５（ｂｒｓ，３Ｈ）
　〈１－［｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝イミノ］－２－（メトキシイミノ）－３－(メチルチオ)プロポキシ〉メチル　アセテート
融点；５３－５５℃ Synthesis Example 11
[N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) propanamido] methyl acetate (present compound 1- 073) and <1-[{3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} imino] -2- (methoxyimino) -3- (methylthio) propoxy> methyl acetate ( Preparation of the present compound 4-001) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) propanamide 500 mg Into a 2 ml solution of N, N-dimethylformamide was added 88.4 mg of 60 wt% sodium hydride (dispersed in mineral oil) at 0 ° C. and stirred for 20 minutes. After stirring, 338 mg of bromomethyl acetate was added to the reaction solution, and stirring was continued at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into ice water and extracted with 50 ml of ethyl acetate. The obtained organic layer was washed with water (50 ml × 2), dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 5: 1 to 1: 1) to give <1-[{3-chloro-1- (Pyridin-3-yl) -1H-pyrazol-4-yl} imino] -2- (methoxyimino) -3- (methylthio) propoxy> methyl acetate 74.2 mg as white crystals, [N- {3-chloro 302 mg of -1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) propanamido] methyl acetate was obtained as a yellow oil.
[N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) propanamido] methyl acetate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.90 (d, J = 2.7 Hz, 1H), 8.61 (dd, J = 4.8, 1.2 Hz, 1H), 8.10 -7.90 (m, 2H), 7.44 (dd, J = 8.4, 4.8 Hz, 1H), 5.80-5.60 (brs, 2H), 3.90-3.60 ( brs, 3H), 3.57 (s, 2H), 2.11 (s, 3H), 2.05-1.85 (brs, 3H)
<1-[{3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} imino] -2- (methoxyimino) -3- (methylthio) propoxy> methyl acetate melting point; 53- 55 ° C
　合成例１２
Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）－Ｎ－（プロプ－２－イン－１－イル）プロパンアミド（本発明化合物１－０１０）の製造
　工程１：ｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル（プロプ－２－イン－１－イル）カーバメートの製造
　６０重量％水素化ナトリウム（鉱油中に分散）１．４３ｇのＮ，Ｎ－ジメチルホルムアミド２０ｍｌ溶液に、氷冷下にてｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イルカーバメート９．２ｇを添加した。添加終了後、室温まで昇温し、同温度にて３０分間撹拌した。攪拌終了後、該反応混合物にプロパルギルブロミド４．０８ｇを添加し、更に室温で１５分間撹拌を継続した。反応終了後、該反応混合物を氷水に注ぎ、酢酸エチル１００ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムにて脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（９：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物９．４ｇを薄茶色アモルファスとして得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９２（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．５７（ｄ，Ｊ＝４．８Ｈｚ，１Ｈ），８．２０-７．８０（ｍ，２Ｈ），７．４１(ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ)，４．００－３．００（ｍ，２Ｈ），２．２９(ｔ，Ｊ＝２．４Ｈｚ，１Ｈ)，１．４７（ｓ，９Ｈ）
　工程２：３－クロロ－Ｎ－（プロプ－２－イン－１－イル）－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－アミンの製造
　ｔｅｒｔ－ブチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル（プロプ－２－イン－１－イル）カーバメート９．４ｇの１，４－ジオキサン１５ｍｌ溶液に、約４Ｍ塩化水素の１，４－ジオキサン溶液５０ｍｌを添加し、室温にて一晩撹拌した。反応終了後、該反応溶液中に析出した固体をろ過にて取り出した。得られた固体をジクロロメタン５０ｍｌに懸濁させた。該懸濁溶液を０℃に冷却し、水酸化ナトリウム２．５ｇの水１０mｌ溶液を添加して、同温度にて１時間撹拌した。反応終了後、ジクロロメタン３０ｍｌ（×３）で抽出した。得られた有機層を飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥した。減圧下にて溶媒を留去した後、得られた固体をジイソプロピルエーテルで洗浄し、目的物５．９ｇを黄白色固体として得た。
融点；１３１－１３３℃ Synthesis Example 12
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) -N- (prop-2-yne-1- Yl) Propanamide (present compound 1-010) Step 1: tert-butyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl (prop-2-yne-1-) Yl) Preparation of carbamate 60% by weight sodium hydride (dispersed in mineral oil) 1.43 g of N, N-dimethylformamide in 20 ml solution under ice-cooling tert-butyl 3-chloro-1- (pyridine-3- Yl) -1H-pyrazol-4-ylcarbamate 9.2 g was added. After completion of the addition, the temperature was raised to room temperature and stirred at the same temperature for 30 minutes. After the completion of stirring, 4.08 g of propargyl bromide was added to the reaction mixture, and stirring was further continued at room temperature for 15 minutes. After completion of the reaction, the reaction mixture was poured into ice water and extracted with 100 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 1: 1) to obtain 9.4 g of the desired product as a light brown amorphous. It was.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.92 (d, J = 2.7 Hz, 1H), 8.57 (d, J = 4.8 Hz, 1H), 8.20-7.80 (M, 2H), 7.41 (dd, J = 8.1, 4.8 Hz, 1H), 4.00-3.00 (m, 2H), 2.29 (t, J = 2.4 Hz, 1H), 1.47 (s, 9H)
Step 2: Preparation of 3-chloro-N- (prop-2-yn-1-yl) -1- (pyridin-3-yl) -1H-pyrazol-4-amine tert-butyl 3-chloro-1- ( Pyridine-3-yl) -1H-pyrazol-4-yl (prop-2-yn-1-yl) carbamate 9.4 g in 1,4-dioxane 15 ml solution and about 4 M hydrogen chloride in 1,4-dioxane solution 50 ml was added and stirred overnight at room temperature. After completion of the reaction, the solid precipitated in the reaction solution was taken out by filtration. The obtained solid was suspended in 50 ml of dichloromethane. The suspension was cooled to 0 ° C., a solution of 2.5 g of sodium hydroxide in 10 ml of water was added, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, extraction was performed with 30 ml (× 3) of dichloromethane. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with diisopropyl ether to obtain 5.9 g of the desired product as a yellowish white solid.
Melting point: 131-133 ° C
　工程３：Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）－Ｎ－（プロプ－２－イン－１－イル）プロパンアミドの製造
　２－（メトキシイミノ）－３－（メチルチオ）プロパン酸０．８４ｇのジクロロメタン１０ｍｌ溶液に、室温にてオキサリルクロリド０．６５ｇ、次いでＮ，Ｎ－ジメチルホルムアミド０．１ｍｌの順に添加した。添加終了後、同温度にて１時間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物を、別途調製した３－クロロ－Ｎ－（プロプ－２－イン－１－イル）－１－（ピリジン－３－イル）－１Ｈ-ピラゾール－４－アミン１．０ｇ及びピリジン０．５１ｇのジクロロメタン１０ｍｌ溶液に添加した。添加終了後、室温にて一晩撹拌を継続した。反応終了後、該反応溶液を水２０ｍｌに添加し、クロロホルム２０ｍｌ（×２）にて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（９：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１．６７ｇを黄色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は７：１であった。
異性体比７
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９２（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６０（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ)，８．０９（ｓ，１Ｈ），８．０２（ｄｄｄ，Ｊ＝８．７，２．７，１．２Ｈｚ，１Ｈ），７．４４（ｄｄ，Ｊ＝８．７，４．８Ｈｚ，１Ｈ），４．６０－４．４０（ｍ，２Ｈ），３．７０（ｓ，３Ｈ），３．５５（ｓ，２Ｈ），２．２８（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ），１，９３（ｓ，３Ｈ）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９２（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６０（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ)，８．０９（ｓ，１Ｈ），８．０２（ｄｄｄ，Ｊ＝８．７，２．７，１．２Ｈｚ，１Ｈ），７．４４（ｄｄ，Ｊ＝８．７，４．８Ｈｚ，１Ｈ），４．８０－４．６０（ｍ，２Ｈ），４．０８（ｓ，３Ｈ），３．５６（ｓ，２Ｈ），２．２８（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ），２．１５（ｓ，３Ｈ） Step 3: N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) -N- (prop-2-yne Preparation of 1-yl) propanamide 2- (methoxyimino) -3- (methylthio) propanoic acid 0.84 g in dichloromethane 10 ml solution at room temperature 0.65 g oxalyl chloride, then N, N-dimethylformamide 0. Added in order of 1 ml. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was separated from 1.0 g of 3-chloro-N- (prop-2-yn-1-yl) -1- (pyridin-3-yl) -1H-pyrazol-4-amine prepared separately and pyridine. 0.51 g of dichloromethane in 10 ml solution was added. After the addition was complete, stirring was continued overnight at room temperature. After completion of the reaction, the reaction solution was added to 20 ml of water and extracted with 20 ml of chloroform (× 2). The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 1: 1) to obtain 1.67 g of the desired product as a yellow oil. Obtained. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 7: 1.
Isomeric ratio 7
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.92 (d, J = 2.7 Hz, 1H), 8.60 (dd, J = 4.8, 1.2 Hz, 1H), 8.09 (S, 1H), 8.02 (ddd, J = 8.7, 2.7, 1.2 Hz, 1H), 7.44 (dd, J = 8.7, 4.8 Hz, 1H), 4. 60-4.40 (m, 2H), 3.70 (s, 3H), 3.55 (s, 2H), 2.28 (t, J = 2.4 Hz, 1H), 1, 93 (s, 3H)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.92 (d, J = 2.7 Hz, 1H), 8.60 (dd, J = 4.8, 1.2 Hz, 1H), 8.09 (S, 1H), 8.02 (ddd, J = 8.7, 2.7, 1.2 Hz, 1H), 7.44 (dd, J = 8.7, 4.8 Hz, 1H), 4. 80-4.60 (m, 2H), 4.08 (s, 3H), 3.56 (s, 2H), 2.28 (t, J = 2.4 Hz, 1H), 2.15 (s, 3H)
　合成例１３
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルスルホニル）－Ｎ－（プロプ－２－イン－１－イル）プロパンアミド（本発明化合物１－０１２）の製造
　合成例７と同様の方法を用いて製造した。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９７（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．５９（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ)，８．１６（ｓ，１Ｈ），７．９８（ｄｄｄ，Ｊ＝８．１，２．７，１．２Ｈｚ，１Ｈ），７．４１（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），４．６０－４．４０（ｍ，４Ｈ），３．８２（ｓ，３Ｈ），２．８８（ｓ，３Ｈ），２．２９（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ） Synthesis Example 13
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylsulfonyl) -N- (prop-2-yne-1 -Ill) Preparation of Propanamide (Compound 1-012 of the Present Invention) The compound was prepared in the same manner as in Synthesis Example 7.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.97 (d, J = 2.7 Hz, 1H), 8.59 (dd, J = 4.8, 1.2 Hz, 1H), 8.16 (S, 1H), 7.98 (ddd, J = 8.1, 2.7, 1.2 Hz, 1H), 7.41 (dd, J = 8.1, 4.8 Hz, 1H), 4. 60-4.40 (m, 4H), 3.82 (s, 3H), 2.88 (s, 3H), 2.29 (t, J = 2.4 Hz, 1H)
　合成例１４
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルスルホニル）－Ｎ－（プロプ－２－イン－１－イル）ブト－３－エナミド（本発明化合物１－０６４）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルスルホニル）－Ｎ－（プロプ－２－イン－１－イル）プロパンアミド２００ｍｇのＮ，Ｎ－ジメチルホルムアミド２．５ｍｌ溶液に、Ｎ，Ｎ，Ｎ’，Ｎ’－テトラメチルジアミノメタン７５ｍｇ及び無水酢酸７５ｍｇを順次添加し、６０℃にて２時間した。攪拌終了後、室温にて一晩撹拌を継続した。反応終了後、該反応溶液を水に添加し、酢酸エチル２０ｍｌにて抽出した後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（４：１～１：９のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１２０ｍｇを白色固体として得た。
融点；１３３－１３４℃ Synthesis Example 14
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylsulfonyl) -N- (prop-2-yne-1 -Il) But-3-enamide (Preparation Compound 1-064) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (Methylsulfonyl) -N- (prop-2-yn-1-yl) propanamide in a solution of 200 mg of N, N-dimethylformamide in 2.5 ml of N, N, N ′, N′-tetramethyldiamino Methane (75 mg) and acetic anhydride (75 mg) were sequentially added, and the mixture was stirred at 60 ° C. for 2 hours. After stirring, stirring was continued overnight at room temperature. After completion of the reaction, the reaction solution was added to water and extracted with 20 ml of ethyl acetate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 4: 1 to 1: 9) to obtain 120 mg of the desired product as a white solid.
Melting point: 133-134 ° C
　合成例１５
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－２－｛１－（メチルスルホニル）シクロプロピル｝－Ｎ－（プロプ－２－イン－１－イル）アセトアミド（本発明化合物１－０３３）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルスルホニル）－Ｎ－（プロプ－２－イン－１－イル）プロパンアミド２００ｍｇのアセトン４ｍｌ溶液に、炭酸カリウム１５０ｍｇ、１，２－ジブロモエタン１１０ｍｇ、１８－クラウン６－エーテル６５ｍｇを順次添加し、６５℃にて７時間撹拌した。反応終了後、該反応溶液を水に添加し、酢酸エチル４ｍｌ（ｘ３）にて抽出した後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（４：１～１：３のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物６５ｍｇを無色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は５：１であった。
異性体比５
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９７（ｄ，Ｊ＝２．４Ｈｚ，１Ｈ），８．６０（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．２４（ｓ，１Ｈ），８．００（ｄｄｄ，Ｊ＝８．４，２．４，１．２Ｈｚ，１Ｈ），７．４３（ｄｄ，Ｊ＝８．４，４．８Ｈｚ，１Ｈ），４．６０－４．４０（ｍ，２Ｈ），３．８３（ｓ，３Ｈ），２．７１（ｓ，３Ｈ），２．２９（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ），１．７５－１．６０（ｍ，４Ｈ）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．００（ｄ，Ｊ＝２．１Ｈｚ，１Ｈ），８．６０（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．２５（ｓ，１Ｈ），８．０６－８．００（ｍ，１Ｈ），７．４３（ｄｄ，Ｊ＝８．４，４．８Ｈｚ，１Ｈ），４．６０－４．４０（ｍ，２Ｈ），３．８３（ｓ，３Ｈ），３．１１（ｓ，３Ｈ），２．２６（ｔ，Ｊ＝２．１Ｈｚ，１Ｈ），１．７５－１．６０（ｍ，４Ｈ） Synthesis Example 15
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -2- {1- (methylsulfonyl) cyclopropyl} -N- (prop -2-In-1-yl) acetamide (Compound 1-033 of the Present Invention) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxy Imino) -3- (methylsulfonyl) -N- (prop-2-yn-1-yl) propanamide 200 mg in acetone 4 ml solution, potassium carbonate 150 mg, 1,2-dibromoethane 110 mg, 18-crown 6-ether 65 mg was sequentially added, and the mixture was stirred at 65 ° C. for 7 hours. After completion of the reaction, the reaction solution was added to water and extracted with 4 ml (x3) of ethyl acetate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 4: 1 to 1: 3) to obtain 65 mg of the desired product as a colorless oil. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 5: 1.
Isomer ratio 5
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.97 (d, J = 2.4 Hz, 1H), 8.60 (dd, J = 4.8, 1.2 Hz, 1H), 8.24 (S, 1H), 8.00 (ddd, J = 8.4, 2.4, 1.2 Hz, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 4. 60-4.40 (m, 2H), 3.83 (s, 3H), 2.71 (s, 3H), 2.29 (t, J = 2.4 Hz, 1H), 1.75-1. 60 (m, 4H)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.00 (d, J = 2.1 Hz, 1H), 8.60 (dd, J = 4.8, 1.2 Hz, 1H), 8.25 (S, 1H), 8.06-8.00 (m, 1H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 4.60-4.40 (m, 2H) 3.83 (s, 3H), 3.11 (s, 3H), 2.26 (t, J = 2.1 Hz, 1H), 1.75-1.60 (m, 4H)
　合成例１６
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－（１－メトキシエチル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド（本発明化合物１－１１３）の製造
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド５００ｍｇのジクロロメタン５ｍｌ溶液に、０℃にてジメチルアセタール２５６ｍｇ、Ｎ，Ｎ－ジイソプロピルエチルアミン３６６ｍｇ、トリフルオロメタンスルホン酸トリメチルシラン６３１ｍｇを順次添加した。添加終了後、室温にて一晩撹拌した。反応終了後、該反応溶液にジクロロメタン５０ｍｌを添加し、飽和炭酸水素ナトリウム水溶液で洗浄した後、無水硫酸ナトリウムで乾燥した。減圧下にて溶媒を留去した後、得られた残留物をｎ－ヘキサン－酢酸エチル（９：１～３：２のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物８５．７ｍｇを無色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は８３：１０であった。
異性体比８３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９４（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．６５－８．５５（ｍ，１Ｈ），８．１０－８．００（ｍ，１Ｈ），７．９１（ｓ，１Ｈ），７．５０－７．４０（ｍ，１Ｈ），６．１５－５．９５（ｍ，１Ｈ），４．１０－３．９０（ｍ，１Ｈ），３．７５（ｓ，３Ｈ），３．５３（ｓ，３Ｈ），１．８６（ｂｒｓ，３Ｈ），１．５５－１．２０（ｍ，６Ｈ）
異性体比１０
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．００－８．９０（ｍ，１Ｈ），８．６５－８．５５（ｍ，１Ｈ），８．１０－８．００（ｍ，１Ｈ），７．８９（ｓ，１Ｈ），７．５０－７．４０（ｍ，１Ｈ），５．５５－５．３５（ｍ，１Ｈ），４．１０－３．９０（ｍ，１Ｈ），３．５５（ｓ，３Ｈ），３．５３（ｓ，３Ｈ），２．０８（ｂｒｓ，３Ｈ），１．５５－１．２０（ｍ，６Ｈ） Synthesis Example 16
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N- (1-methoxyethyl) -2- (methoxyimino) -3- (methylthio) butanamide (present) Preparation of Inventive Compound 1-113) N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide 500 mg dichloromethane To a 5 ml solution, 256 mg of dimethyl acetal, 366 mg of N, N-diisopropylethylamine, and 631 mg of trimethylsilane trifluoromethanesulfonate were sequentially added at 0 ° C. After the addition was complete, the mixture was stirred overnight at room temperature. After completion of the reaction, 50 ml of dichloromethane was added to the reaction solution, washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 9: 1 to 3: 2), 85.7 mg of the desired product was obtained as a colorless oil. The obtained target product was a mixture of two kinds of geometric isomers, and the isomer ratio was 83:10.
Isomeric ratio 83
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.94 (d, J = 2.7 Hz, 1H), 8.65-8.55 (m, 1H), 8.10-8.00 (m , 1H), 7.91 (s, 1H), 7.50-7.40 (m, 1H), 6.15-5.95 (m, 1H), 4.10-3.90 (m, 1H) ), 3.75 (s, 3H), 3.53 (s, 3H), 1.86 (brs, 3H), 1.55-1.20 (m, 6H)
Isomeric ratio 10
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.00-8.90 (m, 1H), 8.65-8.55 (m, 1H), 8.10-8.00 (m, 1H ), 7.89 (s, 1H), 7.50-7.40 (m, 1H), 5.55-5.35 (m, 1H), 4.10-3.90 (m, 1H), 3.55 (s, 3H), 3.53 (s, 3H), 2.08 (brs, 3H), 1.55-1.20 (m, 6H)
　合成例１７
　２－〔２－［｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝アミノ］－２－オキソエチリデン〕－Ｎ－（２，６－ジクロロフェニル）ヒドラジンカルボキサミド（本発明化合物１－２２７）の製造
　工程１：２－［２－｛（２，６－ジクロロフェニル）カルバモイル｝ヒドラゾノ］酢酸の製造
　Ｎ－（２，６－ジクロロフェニル）ヒドラジンカルボキサミド３ｇのエタノール３０ｍｌ溶液に、約９ｍｏｌ／Ｌグリオキシル酸水溶液２．５ｇを添加した。添加終了後、該反応溶液を室温にて一晩撹拌した。反応終了後、該反応溶液から減圧下にて溶媒を留去し、得られた固体を２Ｎ水酸化ナトリウム水溶液３０ｍｌに添加した。添加終了後、該溶液中に析出した不溶物をろ過にて除去した。得られたろ液を、濃塩酸にてｐＨ３とし、析出した固体をろ過にて取り出した。得られた固体を水洗後、減圧下にて乾燥し、目的物２．５ｇを白色固体として得た。
融点；２３８－２４２℃
　工程２：２－〔２－［｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝アミノ］－２－オキソエチリデン〕－Ｎ－（２，６－ジクロロフェニル）ヒドラジンカルボキサミドの製造
　２－［２－｛（２，６－ジクロロフェニル）カルバモイル｝ヒドラゾノ］酢酸２３５ｍｇのジクロロメタン４ｍｌ溶液に、３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン１５０ｍｇ、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩２２３ｍｇを順次添加した。添加終了後、該反応溶液を室温にて２時間撹拌した。反応終了後、該反応溶液に水４ｍｌを添加した。添加終了後、該溶液中に析出した固体をろ過にて取り出した。得られた固体を、水洗後、イソプロピルエーテルにて洗浄した後、減圧下にて乾燥し、目的物２８０ｍｇを白色固体として得た。
融点；２１１－２１４℃ Synthesis Example 17
2- [2-[{3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} amino] -2-oxoethylidene] -N- (2,6-dichlorophenyl) hydrazinecarboxamide ( Step 1: Preparation of 2- [2-{(2,6-dichlorophenyl) carbamoyl} hydrazono] acetic acid In a 30 ml ethanol solution of 3 g N- (2,6-dichlorophenyl) hydrazine carboxamide, About 9 mol / L glyoxylic acid aqueous solution 2.5 g was added. After completion of the addition, the reaction solution was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, and the resulting solid was added to 30 ml of 2N aqueous sodium hydroxide solution. After completion of the addition, insoluble matter precipitated in the solution was removed by filtration. The obtained filtrate was adjusted to pH 3 with concentrated hydrochloric acid, and the precipitated solid was removed by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 2.5 g of the desired product as a white solid.
Melting point: 238-242 ° C
Step 2: 2- [2-[{3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} amino] -2-oxoethylidene] -N- (2,6-dichlorophenyl) Preparation of hydrazinecarboxamide 2- [2-{(2,6-dichlorophenyl) carbamoyl} hydrazono] acetic acid in a solution of 235 mg of dichloromethane in 4 ml of dichloromethane was mixed with 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine 150 mg and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 223 mg were sequentially added. After completion of the addition, the reaction solution was stirred at room temperature for 2 hours. After completion of the reaction, 4 ml of water was added to the reaction solution. After completion of the addition, the solid precipitated in the solution was taken out by filtration. The obtained solid was washed with water and then with isopropyl ether, and then dried under reduced pressure to obtain 280 mg of the desired product as a white solid.
Melting point: 211-214 ° C
　合成例１８
　２－（ヒドロキシイミノ）－Ｎ－｛３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－３－（メチルチオ）ブタンアミド（本発明化合物１－２２６）の製造
　２－（ヒドロキシイミノ）－３－（メチルチオ）ブタン酸２８０ｍｇ及び３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミン３００ｍｇのジクロロメタン６ｍｌ溶液に、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩３９６ｍｇを添加し、室温にて１時間撹拌した。反応終了後、該反応溶液を水１０ｍｌで洗浄した後、減圧下にて溶媒を留去した。溶媒を留去した後、得られた固体をジイソプロピルエーテルで洗浄し、目的物１６０ｍｇを白色固体として得た。
融点；２０７－２０９℃ Synthesis Example 18
Preparation of 2- (hydroxyimino) -N- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3- (methylthio) butanamide (present compound 1-226) 2 To a solution of 280 mg of-(hydroxyimino) -3- (methylthio) butanoic acid and 300 mg of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine in 6 ml of dichloromethane was added 1-ethyl-3- ( 396 mg of 3-dimethylaminopropyl) carbodiimide hydrochloride was added and stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was washed with 10 ml of water, and then the solvent was distilled off under reduced pressure. After the solvent was distilled off, the obtained solid was washed with diisopropyl ether to obtain 160 mg of the desired product as a white solid.
Melting point: 207-209 ° C
　合成例１９
　Ｎ－｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミドの製造（本発明化合物３－００１）
　工程１：エチル　２－（メトキシイミノ）－３－（メチルチオ）プロパノエートの製造
　エチル　３－ブロモ－２－（メトキシイミノ）プロパノエート２．０ｇのＮ，Ｎ－ジメチルホルムアミド３０ｍｌの溶液に、メチルメルカプタンナトリウム７５０ｍｇを添加した。添加終了後、該反応混合物を室温にて２時間攪拌した。攪拌終了後、該反応混合物を８０℃に昇温し、同温度にて１時間撹拌を継続した。反応終了後、該反応混合物に水３０ｍｌを添加し、酢酸エチル５０ｍｌにて抽出した。得られた有機層を飽和炭酸水素ナトリウム水溶液で洗浄した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥した。減圧下にて溶媒を留去し、目的物２ｇを薄黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．３４（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．０４（ｓ，３Ｈ），３．５５（ｓ，２Ｈ），２．１０（ｓ，３Ｈ），１．３５（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　工程２：２－（メトキシイミノ）－３－（メチルチオ）プロパン酸の製造
　エチル　２－（メトキシイミノ）－３－（メチルチオ）プロパノエート１．８４ｇの水１０ｍｌ及びエタノール１０ｍｌの溶液に、水酸化ナトリウム４３０ｍｇを添加した。添加終了後、該反応混合物を室温にて２日間撹拌した。反応終了後、該反応混合物を１Ｎ塩酸水溶液にてｐＨを２とした後、酢酸エチル２０ｍｌ（×２）にて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた固体を、ヘキサン：イソプロピルエーテル［５：１（体積比、以下同じである。）］の混合溶液６ｍｌで洗浄し、目的物０．４ｇを黄白色固体として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０８（ｓ，３Ｈ），３．５３（ｓ，２Ｈ），２．１４（ｓ，３Ｈ） Synthesis Example 19
Production of N- {4-methyl-2- (pyridin-3-yl) thiazol-5-yl} -2- (methoxyimino) -3- (methylthio) propanamide (present compound 3-001)
Step 1: Preparation of ethyl 2- (methoxyimino) -3- (methylthio) propanoate In a solution of 2.0 g of ethyl 3-bromo-2- (methoxyimino) propanoate in 30 ml of N, N-dimethylformamide, 750 mg of sodium methyl mercaptan Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the stirring, the reaction mixture was heated to 80 ° C. and stirring was continued for 1 hour at the same temperature. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with 50 ml of ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, washed with saturated brine, and then dried over anhydrous sodium sulfate in that order. The solvent was distilled off under reduced pressure to obtain 2 g of the desired product as a pale yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.34 (q, J = 7.2 Hz, 2H), 4.04 (s, 3H), 3.55 (s, 2H), 2.10 ( s, 3H), 1.35 (t, J = 7.2 Hz, 3H)
Step 2: Preparation of 2- (methoxyimino) -3- (methylthio) propanoic acid 430 mg of sodium hydroxide in a solution of 1.84 g of ethyl 2- (methoxyimino) -3- (methylthio) propanoate in 10 ml of water and 10 ml of ethanol Was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 days. After completion of the reaction, the reaction mixture was adjusted to pH 2 with 1N aqueous hydrochloric acid solution and extracted with 20 ml (× 2) of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 6 ml of a mixed solution of hexane: isopropyl ether [5: 1 (volume ratio, the same applies hereinafter)] to obtain 0.4 g of the desired product as a pale yellow solid.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.08 (s, 3H), 3.53 (s, 2H), 2.14 (s, 3H)
　工程３：Ｎ－｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミドの製造
　２－（メトキシイミノ）－３－（メチルチオ）プロパン酸３７０ｍｇのジクロロメタン３ｍｌ溶液に、オキサリルクロリド３６０ｍｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、該反応混合物を室温にて２時間撹拌した。攪拌終了後、該反応混合物を、別途調製した４－メチル－２－（ピリジン－３－イル）チアゾール－５－アミン　２塩酸塩５００ｍｇ及びピリジン７４７ｍｇの二塩化エチレン５ｍｌ溶液に滴下した。滴下終了後、該反応混合物を室温にて３０分撹拌した。反応終了後、該反応混合物を水１０ｍｌ、次いで飽和炭酸水素ナトリウム水溶液１０ｍｌで洗浄した後、分液操作にて有機層を分取した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ｎ－ヘキサン－酢酸エチル（１：２）にて溶出する中圧分取液体クロマトグラフィーにて精製した。精製後に得られた個体を、ジイソプロピルエーテル１５ｍｌで洗浄し、目的物５４０ｍｇを黄色固体として得た。
融点１０１－１０４℃ Step 3: Production of N- {4-methyl-2- (pyridin-3-yl) thiazol-5-yl} -2- (methoxyimino) -3- (methylthio) propanamide 2- (methoxyimino) -3 -360 mg of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added to a solution of 370 mg of (methylthio) propanoic acid in 3 ml of dichloromethane. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the stirring, the reaction mixture was added dropwise to a separately prepared solution of 4-methyl-2- (pyridin-3-yl) thiazol-5-amine dihydrochloride (500 mg) and pyridine (747 mg) in ethylene dichloride (5 ml). After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed with 10 ml of water and then with 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and then the organic layer was separated by a liquid separation operation. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 2). The solid obtained after purification was washed with 15 ml of diisopropyl ether to obtain 540 mg of the desired product as a yellow solid.
Melting point 101-104 ° C
　合成例２０
　Ｎ－｛４－クロロ－２－（ピリジン－３－イル）チアゾール－５－イル｝－Ｎ－エチル－２－（メトキシイミノ）－３－（メチルチオ）プロパンアミドの製造（本発明化合物３－００２）
　２－（メトキシイミノ）－３－（メチルチオ）プロパン酸１５３ｍｇのジクロロメタン３ｍｌ溶液に、オキサリルクロリド１５９ｍｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、室温にて２時間撹拌した。攪拌終了後、該反応混合物を、別途調製した４－クロロ―Ｎ－エチル－２－（ピリジン－３－イル）チアゾール－５－アミン１５０ｍｇ及びピリジン１９８ｍｇの二塩化エチレン５ｍｌ溶液に室温にて滴下した。滴下終了後、同温度にて終夜撹拌した。反応終了後、該反応混合物を水１０ｍｌ、次いで飽和炭酸水素ナトリウム水溶液１０ｍｌで洗浄した後、分液操作にて有機層を分取した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残渣を、ｎ－ヘキサン－酢酸エチル（３：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１００ｍｇを薄黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．０９（ｄ，Ｊ＝１．８Ｈｚ，１Ｈ），８．７０（ｄｄ，Ｊ＝４．８，１．２Ｈｚ，１Ｈ），８．２０（ｄｄｄ，Ｊ＝８．１，１．８，１．２Ｈｚ，１Ｈ），７．４０（ｄｄ，Ｊ＝８．１，４．８Ｈｚ，１Ｈ），３．９２－３．８１（ｍ，２Ｈ），３．３６（ｂｒｓ，３Ｈ），３．５４（ｓ，２Ｈ），２．０８（ｓ，３Ｈ），１．２８（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ） Synthesis Example 20
Preparation of N- {4-chloro-2- (pyridin-3-yl) thiazol-5-yl} -N-ethyl-2- (methoxyimino) -3- (methylthio) propanamide (present compound 3-002 )
To a solution of 153 mg of 2- (methoxyimino) -3- (methylthio) propanoic acid in 3 ml of dichloromethane, 159 mg of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added in this order. After completion of the addition, the mixture was stirred at room temperature for 2 hours. After completion of the stirring, the reaction mixture was added dropwise to a separately prepared solution of 150 mg of 4-chloro-N-ethyl-2- (pyridin-3-yl) thiazol-5-amine and 198 mg of pyridine in 5 ml of ethylene dichloride at room temperature. . After completion of dropping, the mixture was stirred overnight at the same temperature. After completion of the reaction, the reaction mixture was washed with 10 ml of water and then with 10 ml of a saturated aqueous sodium hydrogen carbonate solution, and then the organic layer was separated by a liquid separation operation. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 100 mg of the desired product as a pale yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.09 (d, J = 1.8 Hz, 1H), 8.70 (dd, J = 4.8, 1.2 Hz, 1H), 8.20 (Ddd, J = 8.1, 1.8, 1.2 Hz, 1H), 7.40 (dd, J = 8.1, 4.8 Hz, 1H), 3.92-3.81 (m, 2H ), 3.36 (brs, 3H), 3.54 (s, 2H), 2.08 (s, 3H), 1.28 (t, J = 7.2 Hz, 3H)
　合成例２１
　２－（メトキシイミノ）－Ｎ－｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝－３－（メチルチオ）ブタンアミドの製造（本発明化合物３－００５）
　工程１：２－ブロモ－４－メチルチアゾール－５－アミン　塩酸塩の製造
　国際公開第２０１０／１２９４９７号記載の方法により合成したｔｅｒｔ－ブチル　(２－ブロモ－４－メチルチアゾール－５－イル)カーバメート１．０ｇの１，４－ジオキサン１０ｍｌ溶液に、約４Ｍ塩化水素の１，４－ジオキサン溶液２０ｍｌを添加した。添加終了後、室温にて一晩撹拌した。反応終了後、該反応溶液からデカンテーションにて上澄みを取り除き、１，４－ジオキサン２０ｍｌを添加した後、再度デカンテーションにより上澄みを取り除いた。更に、残留した懸濁溶液にジクロロメタン２０ｍｌを添加した。この、２－ブロモ－４－メチルチアゾール－５－アミン　塩酸塩のジクロロメタン溶液はそのまま次の工程に用いた。
　工程２：Ｎ－（２－ブロモ－４－メチルチアゾール－５－イル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミドの製造
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸０．６ｇのジクロロメタン５ｍｌ溶液に、オキサリルクロリド０．６５ｇ、次いでＮ，Ｎ－ジメチルホルムアミド１０ｍｇの順に添加した。添加終了後、室温にて１時間撹拌した。反応終了後、該反応溶液から減圧下にて溶媒を留去し、得られた残留物を上記工程１で得られた２－ブロモ－４－メチルチアゾール－５－アミン　塩酸塩のジクロロメタン溶液に添加し、氷浴にて冷却した後、ピリジン１．５ｇを添加し、室温にて１時間撹拌した。反応終了後、該反応溶液に２Ｎ塩酸水溶液３０ｍｌ及び酢酸エチル３０ｍｌを添加した後、有機層を分液にて取り出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１）にて溶出するシリカゲルクロマトグラフィーにて精製し、目的物２７０ｍｇを薄黄色固体として得た。
融点；１０３－１０４℃ Synthesis Example 21
Preparation of 2- (methoxyimino) -N- {4-methyl-2- (pyridin-3-yl) thiazol-5-yl} -3- (methylthio) butanamide (present compound 3-005)
Step 1: Preparation of 2-bromo-4-methylthiazol-5-amine hydrochloride Tert-butyl (2-bromo-4-methylthiazol-5-yl) carbamate synthesized by the method described in WO2010 / 129497 To 1.0 g of 1,4-dioxane in 10 ml, 20 ml of about 4 M hydrogen chloride in 1,4-dioxane was added. After the addition was complete, the mixture was stirred overnight at room temperature. After completion of the reaction, the supernatant was removed from the reaction solution by decantation, 20 ml of 1,4-dioxane was added, and the supernatant was removed again by decantation. Furthermore, 20 ml of dichloromethane was added to the remaining suspension solution. This dichloromethane solution of 2-bromo-4-methylthiazol-5-amine hydrochloride was directly used in the next step.
Step 2: Preparation of N- (2-bromo-4-methylthiazol-5-yl) -2- (methoxyimino) -3- (methylthio) butanamide 2- (methoxyimino) -3- (methylthio) butanoic acid 0 To a solution of .6 g of dichloromethane in 5 ml, 0.65 g of oxalyl chloride and then 10 mg of N, N-dimethylformamide were added in this order. After completion of the addition, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, and the resulting residue was added to the dichloromethane solution of 2-bromo-4-methylthiazol-5-amine hydrochloride obtained in Step 1 above. After cooling in an ice bath, 1.5 g of pyridine was added and stirred at room temperature for 1 hour. After completion of the reaction, 30 ml of 2N hydrochloric acid solution and 30 ml of ethyl acetate were added to the reaction solution, and then the organic layer was taken out by liquid separation. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with n-hexane-ethyl acetate (3: 1) to obtain 270 mg of the desired product as a pale yellow solid.
Melting point: 103-104 ° C
　工程３：２－（メトキシイミノ）－Ｎ－｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝－３－（メチルチオ）ブタンアミドの製造
　Ｎ－（２－ブロモ－４－メチルチアゾール－５－イル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド０．１ｇ及び３－ピリジルボロン酸０．０５ｇの１，４－ジオキサン５ｍｌ及び水３ｍｌ溶液に、炭酸カリウム０．２ｇ及びビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド０．０６ｇを添加し、９０℃にて１時間撹拌した。反応終了後、該反応溶液に水２０ｍｌを添加し、酢酸エチル２０ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン：酢酸エチル（１：１）にて溶出するシリカゲルクロマトグラフィーにて精製し、目的物３５ｍｇを黄色固体として得た。
融点；９６－９８℃ Step 3: Preparation of 2- (methoxyimino) -N- {4-methyl-2- (pyridin-3-yl) thiazol-5-yl} -3- (methylthio) butanamide N- (2-Bromo-4- To a solution of 0.1 g of methylthiazol-5-yl) -2- (methoxyimino) -3- (methylthio) butanamide and 0.05 g of 3-pyridylboronic acid in 5 ml of 1,4-dioxane and 3 ml of water, 0. 2 g and bis (triphenylphosphine) palladium (II) dichloride 0.06 g were added and stirred at 90 ° C. for 1 hour. After completion of the reaction, 20 ml of water was added to the reaction solution and extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with n-hexane: ethyl acetate (1: 1) to obtain 35 mg of the desired product as a yellow solid.
Melting point: 96-98 ° C
　合成例２２
　Ｎ－（２，６－ジクロロフェニル）－２－〔２－［｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝アミノ］－２－オキソエチリデン〕ヒドラジンカルボキサミドの製造（本発明化合物３－０３０）
　工程１：２－［２－｛（２，６－ジクロロフェニル）カルバモイル｝ヒドラゾノ］酢酸の製造
　Ｎ－（２，６－ジクロロフェニル）ヒドラジンカルボキサミド３ｇのエタノール３０ｍｌ溶液に、約９ｍｏｌ／Ｌグリオキシル酸水溶液２．５ｇを添加し、室温にて一晩撹拌した。反応終了後、該反応溶液から減圧下にて溶媒を留去し、得られた固体を２Ｎ水酸化ナトリウム水溶液３０ｍｌに添加し、不溶物をろ過にて除去した。得られたろ液を、濃塩酸にてｐＨ３とし、析出した固体をろ過にて取り出した。得られた固体を水洗後、減圧下にて乾燥し、目的物２．５ｇを白色固体として得た。
融点；２３８－２４２℃
　工程２：Ｎ－（２，６－ジクロロフェニル）－２－〔２－［｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝アミノ］－２－オキソエチリデン〕ヒドラジンカルボキサミドの製造の製造
　２－［２－｛（２，６－ジクロロフェニル）カルバモイル｝ヒドラゾノ］酢酸１６０ｍｇのジクロロメタン４ｍｌ溶液に、４－メチル－２－（ピリジン－３－イル）チアゾール－５－アミン１００ｍｇ、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩１３１ｍｇを順次添加し、室温にて１時間撹拌した。反応終了後、該反応溶液に水２ｍｌを添加し、析出した固体をろ過にて取り出した。得られた固体を、水洗後、イソプロピルエーテルにて洗浄した後、減圧下にて乾燥し、目的物２１０ｍｇを黄色固体として得た。
融点；２３２－２３４℃ Synthesis Example 22
Preparation of N- (2,6-dichlorophenyl) -2- [2-[{4-methyl-2- (pyridin-3-yl) thiazol-5-yl} amino] -2-oxoethylidene] hydrazinecarboxamide Invention Compound 3-030)
Step 1: Preparation of 2- [2-{(2,6-dichlorophenyl) carbamoyl} hydrazono] acetic acid 3 g of N- (2,6-dichlorophenyl) hydrazinecarboxamide in 30 ml of ethanol, about 9 mol / L aqueous glyoxylic acid solution. 5 g was added and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, the resulting solid was added to 30 ml of 2N aqueous sodium hydroxide solution, and insoluble matters were removed by filtration. The obtained filtrate was adjusted to pH 3 with concentrated hydrochloric acid, and the precipitated solid was removed by filtration. The obtained solid was washed with water and dried under reduced pressure to obtain 2.5 g of the desired product as a white solid.
Melting point: 238-242 ° C
Step 2: N- (2,6-Dichlorophenyl) -2- [2-[{4-methyl-2- (pyridin-3-yl) thiazol-5-yl} amino] -2-oxoethylidene] hydrazinecarboxamide Preparation of Preparation 2- [2-{(2,6-dichlorophenyl) carbamoyl} hydrazono] acetic acid in 160 mg of dichloromethane in 4 ml solution was added 4-methyl-2- (pyridin-3-yl) thiazol-5-amine 100 mg, 1- Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 131 mg was sequentially added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 2 ml of water was added to the reaction solution, and the precipitated solid was removed by filtration. The obtained solid was washed with water and then with isopropyl ether and then dried under reduced pressure to obtain 210 mg of the desired product as a yellow solid.
Melting point: 232-234 ° C
　参考例１
　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造（その１）
　３－クロロ－１Ｈ－ピラゾール－４－アミン１０．７ｇのトルエン７０ｍｌの溶液に、３－ブロモピリジン１２．７ｇ、ヨウ化銅（１価）２．６５ｇ、炭酸カリウム２８．９ｇ、ｔｒａｎｓ－Ｎ，Ｎ’－ジメチルシクロヘキサン－１，２－ジアミン３．９６ｇ及びジメチルスルホキシド２０ｍｌを順次添加した。添加終了後、反応容器内を窒素ガスで置換した後、１００℃にて２時間撹拌した。反応終了後、該反応混合物中に析出した固体をろ別した。得られたろ液に酢酸エチル１００ｍｌを添加し、７重量％アンモニア水溶液５０ｍｌ次いで飽和食塩水で洗浄した後、無水硫酸ナトリウムで脱水・乾燥した。減圧下にて溶媒を留去した。得られた固体をジイソプロピルエーテルで洗浄し、目的物８．５２ｇを茶褐色固体として得た。
融点；１３９－１４３℃ Reference example 1
Production of 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine (Part 1)
To a solution of 10.7 g of 3-chloro-1H-pyrazol-4-amine in 70 ml of toluene, 12.7 g of 3-bromopyridine, 2.65 g of copper iodide (monovalent), 28.9 g of potassium carbonate, trans-N, N'-dimethylcyclohexane-1,2-diamine (3.96 g) and dimethyl sulfoxide (20 ml) were successively added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 100 ° C. for 2 hours. After completion of the reaction, the solid precipitated in the reaction mixture was filtered off. To the obtained filtrate, 100 ml of ethyl acetate was added, washed with 50 ml of a 7% by weight aqueous ammonia solution and then with saturated brine, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained solid was washed with diisopropyl ether to obtain 8.52 g of the desired product as a brown solid.
Melting point: 139-143 ° C
　参考例２
　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造（その２）
　工程１：エチル　３－クロロ－１Ｈ－ピラゾール－４－カルボキシレートの製造
　エチル　１－ｔｅｒｔ－ブチル－５－クロロ－１Ｈ－ピラゾール－４－カルボキシレート９．７１ｇに、氷冷下にて濃塩酸３０ｍｌを添加した。添加終了後、室温にて一晩撹拌した。攪拌終了後、該反応混合物に濃塩酸１０ｍｌを添加し、一昼夜撹拌を継続した。反応終了後、該反応混合物を０℃に冷却し、水酸化ナトリウム水溶液で中和した後、酢酸エチル１００ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた固体を、ｎ－ヘキサンで洗浄し、目的物６．２８ｇを白色固体として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ１１．２（ｂｒｓ，１Ｈ），８．１０（ｓ，１Ｈ），４．３３（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），１．３６（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　工程２：エチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシレートの製造
　エチル　３－クロロ－１Ｈ－ピラゾール－４－カルボキシレート１０．２ｇのＮ，Ｎ－ジメチルホルムアミド１５０ｍｌ溶液に、３－ヨードピリジン１５．６ｇ、ヨウ化銅（１価）２．２３ｇ及び炭酸セシウム３３．０ｇを順次添加した。添加終了後、反応容器内部を窒素ガスで置換した後、１３０℃にて５時間撹拌した。反応終了後、該反応混合物を室温まで放冷し、１Ｎ水酸化ナトリウム水溶液１００ｍｌを添加した。該反応混合物中の不純物を、減圧下セライトろ過により除去した後、得られたろ液を酢酸エチル１００ｍｌにて抽出した。得られた有機層を飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物７．５６ｇを白色固体として得た。
融点；９０－９３℃。 Reference example 2
Production of 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine (Part 2)
Step 1: Preparation of ethyl 3-chloro-1H-pyrazole-4-carboxylate To 9.71 g of ethyl 1-tert-butyl-5-chloro-1H-pyrazole-4-carboxylate, 30 ml of concentrated hydrochloric acid under ice-cooling Was added. After the addition was complete, the mixture was stirred overnight at room temperature. After completion of the stirring, 10 ml of concentrated hydrochloric acid was added to the reaction mixture, and stirring was continued for a whole day and night. After completion of the reaction, the reaction mixture was cooled to 0 ° C., neutralized with an aqueous sodium hydroxide solution, and extracted with 100 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with n-hexane to obtain 6.28 g of the desired product as a white solid.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 11.2 (brs, 1H), 8.10 (s, 1H), 4.33 (q, J = 7.2 Hz, 2H), 1.36 ( t, J = 7.2 Hz, 3H)
Step 2: Preparation of ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 10.3-g N, N-dimethyl ethyl 3-chloro-1H-pyrazole-4-carboxylate To a 150 ml formamide solution, 15.6 g of 3-iodopyridine, 2.23 g of copper iodide (monovalent) and 33.0 g of cesium carbonate were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 130 ° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and 100 ml of 1N aqueous sodium hydroxide solution was added. Impurities in the reaction mixture were removed by Celite filtration under reduced pressure, and the obtained filtrate was extracted with 100 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1) to obtain 7.56 g of the desired product as a white solid.
Melting point: 90-93 ° C.
　工程３：３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸の製造
　エチル　３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシレート１６．７５ｇのエタノール１３０ｍｌ溶液に、水酸化カリウム５．６ｇ及び水１３０ｍｌを順次添加した。添加終了後、室温にて一晩撹拌した。反応終了後、２Ｎ塩酸水溶液を添加し、該反応混合物のｐＨを４とした後、析出した固体をろ過にて取り出し、取り出した固体を水で洗浄した。得られた固体をトルエン２００ｍｌに添加し、トルエンを還流させながらディーン・スターク管を用いて脱水した。脱水終了後、トルエン中の固体をろ過にて取り出し、目的物１４．５ｇを薄桃色固体として得た。
融点；２７５－２８２℃。
　工程４：３－（３－クロロ－４－ニトロ－１Ｈ－ピラゾール－１－イル）ピリジンの製造
　濃塩酸９ｍｌ及び発煙硝酸３．１ｍｌ溶液に、無水酢酸１．７２ｍｌを４０℃以下の温度で滴下した。滴下終了後、該反応混合物を室温にて３０分撹拌した。攪拌終了後、該反応混合物を６０℃に加熱した。加熱終了後、該反応混合物に、３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸５ｇを、５回に分けて６０℃を保ちながら添加した。添加終了後、６５℃にて２時間撹拌を継続した。反応終了後、該反応混合物を氷水に注いだ後、１Ｎ水酸化ナトリウム水溶液にて中和した。析出した固体をろ過した後、水洗、乾燥して目的物４．２ｇを薄黄色固体として得た。
融点；１３９－１４０℃
　工程５：３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造
　３－（３－クロロ－４－ニトロ－１Ｈ－ピラゾール－１－イル）ピリジン４ｇの酢酸エチル２０ｍｌ、酢酸１０ｍｌ及び水１０ｍｌ溶液を６５℃に加熱し、還元鉄２．５ｇを少しずつ添加した。添加終了後、７０℃にて２時間撹拌した。反応終了後、該反応溶液を室温まで放冷し、水５０ｍｌを添加した後、炭酸水素ナトリウムにて該反応溶液のｐＨを１０とした。該反応溶液中の不溶物をろ過にて取り除き、ろ液の有機層を分液にて取り出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去した。得られた固体をジイソプロピルエーテルにて洗浄し、目的物２．６ｇを薄紫色固体として得た。
融点；１４２－１４４℃
　また、参考例２と同様の合成法にて、以下の中間体を合成した。
　３－（３－メチル－４－ニトロ－１Ｈ－ピラゾール－１－イル）ピリジン
融点；１２１－１２２℃ Step 3: Preparation of 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid Ethyl 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate 5.6 g of potassium hydroxide and 130 ml of water were sequentially added to a solution of 16.75 g of ethanol in 130 ml. After the addition was complete, the mixture was stirred overnight at room temperature. After completion of the reaction, 2N hydrochloric acid aqueous solution was added to adjust the pH of the reaction mixture to 4. Then, the precipitated solid was removed by filtration, and the removed solid was washed with water. The obtained solid was added to 200 ml of toluene and dehydrated using a Dean-Stark tube while the toluene was refluxed. After completion of dehydration, the solid in toluene was removed by filtration to obtain 14.5 g of the desired product as a light pink solid.
Melting point: 275-282 ° C.
Step 4: Preparation of 3- (3-chloro-4-nitro-1H-pyrazol-1-yl) pyridine 1.72 ml of acetic anhydride was added dropwise to a solution of concentrated hydrochloric acid 9 ml and fuming nitric acid 3.1 ml at a temperature of 40 ° C or lower. did. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After stirring, the reaction mixture was heated to 60 ° C. After completion of heating, 5 g of 3-chloro-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid was added to the reaction mixture in 5 portions while maintaining 60 ° C. After completion of the addition, stirring was continued at 65 ° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into ice water and neutralized with 1N aqueous sodium hydroxide solution. The precipitated solid was filtered, washed with water, and dried to obtain 4.2 g of the desired product as a pale yellow solid.
Melting point: 139-140 ° C
Step 5: Preparation of 3-chloro-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3- (3-Chloro-4-nitro-1H-pyrazol-1-yl) pyridine 4 g of ethyl acetate A solution of 20 ml, 10 ml of acetic acid and 10 ml of water was heated to 65 ° C., and 2.5 g of reduced iron was added little by little. After completion of the addition, the mixture was stirred at 70 ° C. for 2 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature, 50 ml of water was added, and the pH of the reaction solution was adjusted to 10 with sodium bicarbonate. The insoluble matter in the reaction solution was removed by filtration, and the organic layer of the filtrate was taken out by liquid separation. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with diisopropyl ether to obtain 2.6 g of the desired product as a light purple solid.
Melting point: 142-144 ° C
In addition, the following intermediate was synthesized by the same synthesis method as in Reference Example 2.
3- (3-Methyl-4-nitro-1H-pyrazol-1-yl) pyridine melting point; 121-122 ° C.
　参考例３
　エチル　３－クロロ－１Ｈ－ピラゾール－４－カルボキシレートの製造
　濃塩酸２．２ｍｌ、酢酸２．２ｍｌ及びリン酸１．３ｍｌの溶液に、エチル　３－アミノ－１H－ピラゾール－４－カルボキシレート１ｇを添加し、－５℃に冷却した。冷却終了後、該反応混合物に亜硝酸ナトリウム０．４９ｇの水１ｍｌ溶液を、－５℃を保ちなが滴下し、ジアゾニウム塩溶液を調製した。別途濃塩酸６．４ｍｌを０℃に冷却し、亜硫酸水素ナトリウム０．７３ｇの水１．５ｍｌ溶液を０℃を保ちながら滴下した。滴下終了後、硫酸銅５水和物０．１６ｇを添加した。添加終了後、該反応混合物に、先に調製したジアゾニウム塩溶液と、亜硫酸水素ナトリウム０．７３ｇの水１．５ｍｌ溶液を、０℃を保ちながら同時に滴下した。滴下終了後、１０分間撹拌し、該反応溶液を氷水に注いだ後、水酸化カリウム水溶液で中和した。クロロホルム２０ｍｌ（ｘ３）にて抽出し、得られた有機層を飽和食塩水次いで無水硫酸ナトリウムで脱水し、乾燥した。得られた残渣をｎ－ヘキサン－酢酸エチル（５：１～１：２のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物４２６ｍｇを白色固体として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ１１．２（ｂｒｓ，１Ｈ），８．１０（ｓ，１Ｈ），４．３３（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），１．３６（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ） Reference example 3
Preparation of ethyl 3-chloro-1H-pyrazole-4-carboxylate To a solution of 2.2 ml of concentrated hydrochloric acid, 2.2 ml of acetic acid and 1.3 ml of phosphoric acid, 1 g of ethyl 3-amino-1H-pyrazole-4-carboxylate was added. Added and cooled to -5 ° C. After completion of cooling, a solution of 0.49 g of sodium nitrite in 1 ml of water was added dropwise to the reaction mixture while maintaining at −5 ° C. to prepare a diazonium salt solution. Separately, 6.4 ml of concentrated hydrochloric acid was cooled to 0 ° C., and a solution of 0.73 g of sodium bisulfite in 1.5 ml of water was added dropwise while maintaining 0 ° C. After the completion of dropping, 0.16 g of copper sulfate pentahydrate was added. After completion of the addition, the previously prepared diazonium salt solution and a solution of 0.73 g of sodium hydrogen sulfite in 1.5 ml of water were simultaneously added dropwise to the reaction mixture while maintaining 0 ° C. After completion of the dropwise addition, the mixture was stirred for 10 minutes, poured into ice water, and neutralized with an aqueous potassium hydroxide solution. Extraction was performed with 20 ml (x3) of chloroform, and the obtained organic layer was dehydrated with saturated brine and then anhydrous sodium sulfate and dried. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 5: 1 to 1: 2) to obtain 426 mg of the desired product as a white solid.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 11.2 (brs, 1H), 8.10 (s, 1H), 4.33 (q, J = 7.2 Hz, 2H), 1.36 ( t, J = 7.2 Hz, 3H)
　参考例４
　２－（メトキシイミノ）－３－（メチルチオ）プロパン酸の製造
　工程１：エチル　２－（メトキシイミノ）－３－（メチルチオ）プロパノエートの製造
　エチル　３－ブロモ－２－（メトキシイミノ）プロパノエート２．０ｇのＮ，Ｎ－ジメチルホルムアミド３０ｍｌの溶液に、メチルメルカプタンナトリウム７５０ｍｇを添加した。添加終了後、室温にて２時間攪拌した。攪拌終了後、該反応混合物を８０℃に昇温した後、同温度で１時間撹拌を継続した。反応終了後、該反応混合物に水３０ｍｌを添加し、酢酸エチル５０ｍｌで抽出した。得られた有機層を、飽和炭酸水素ナトリウム水溶液で洗浄した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥した。減圧下にて溶媒を留去し、目的物２ｇを薄黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．３４（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．０４（ｓ，３Ｈ），３．５５（ｓ，２Ｈ），２．１０（ｓ，３Ｈ），１．３５（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　工程２：２－（メトキシイミノ）－３－（メチルチオ）プロパン酸の製造
　エチル　２－（メトキシイミノ）－３－（メチルチオ）プロパノエート１．８４ｇの水１０ｍｌ及びエタノール１０ｍｌの混合溶液に、水酸化ナトリウム４３０ｍｇを添加した。添加終了後、室温にて２日間撹拌した。反応終了後、該反応溶液に１Ｎ塩酸水溶液を添加し、該反応溶液のｐＨを２とした後、酢酸エチル２０ｍｌ（×２）にて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた固体を、ヘキサン：イソプロピルエーテル（５：１）の混合溶液６ｍｌで洗浄し、目的物０．４ｇを黄白色固体として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０８（ｓ，３Ｈ），３．５３（ｓ，２Ｈ），２．１４（ｓ，３Ｈ） Reference example 4
Preparation of 2- (methoxyimino) -3- (methylthio) propanoic acid Step 1: Preparation of ethyl 2- (methoxyimino) -3- (methylthio) propanoate Ethyl 3-bromo-2- (methoxyimino) propanoate 2.0 g 750 mg of sodium methyl mercaptan was added to a solution of 30 ml of N, N-dimethylformamide. After completion of the addition, the mixture was stirred at room temperature for 2 hours. After completion of the stirring, the reaction mixture was heated to 80 ° C. and then stirred at the same temperature for 1 hour. After completion of the reaction, 30 ml of water was added to the reaction mixture and extracted with 50 ml of ethyl acetate. The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, washed with saturated brine and then dried over anhydrous sodium sulfate in that order. The solvent was distilled off under reduced pressure to obtain 2 g of the desired product as a pale yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.34 (q, J = 7.2 Hz, 2H), 4.04 (s, 3H), 3.55 (s, 2H), 2.10 ( s, 3H), 1.35 (t, J = 7.2 Hz, 3H)
Step 2: Preparation of 2- (methoxyimino) -3- (methylthio) propanoic acid To a mixed solution of 1.84 g of ethyl 2- (methoxyimino) -3- (methylthio) propanoate in 10 ml of water and 10 ml of ethanol, sodium hydroxide 430 mg was added. After completion of the addition, the mixture was stirred at room temperature for 2 days. After completion of the reaction, 1N aqueous hydrochloric acid solution was added to the reaction solution to adjust the pH of the reaction solution to 2, and the mixture was extracted with 20 ml (× 2) of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 6 ml of a mixed solution of hexane: isopropyl ether (5: 1) to obtain 0.4 g of the objective product as a yellowish white solid.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.08 (s, 3H), 3.53 (s, 2H), 2.14 (s, 3H)
　参考例５
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸の製造
　工程１：エチル　２－（メトキシイミノ）－３－（トシルオキシ）ブタノエートの製造（化合物Ｄ－００１）
　独国特許出願公開第３２２０５２４号明細書に記載の方法に従って合成したエチル　３－ヒドロキシ－２－（メトキシイミノ）ブタノエート１．６３ｇのジクロロメタン１０ｍｌ溶液に、トリエチルアミン２．３６ｇ、ｐ－トルエンスルホニルクロリド２．１４ｇ及び４－ジメチルアミノピリジン０．３４ｇを順次添加した。添加終了後、該反応混合物を室温にて一晩撹拌した。反応終了後、該反応溶液に飽和炭酸水素ナトリウム水溶液２０ｍｌを添加し、酢酸エチル３０ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残渣をｎ－ヘキサン－酢酸エチル（５：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．８ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ７．７８（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ），７．３２（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ），５．３１（ｑ，Ｊ＝６．９Ｈｚ，１Ｈ），４．２８－４．１６（ｍ，２Ｈ），３．８２（ｓ，３Ｈ），２．４４（ｓ，３Ｈ），１．５３（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）, １．２７（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ） Reference Example 5
Preparation of 2- (methoxyimino) -3- (methylthio) butanoic acid Step 1: Preparation of ethyl 2- (methoxyimino) -3- (tosyloxy) butanoate (Compound D-001)
To a solution of 1.63 g of ethyl 3-hydroxy-2- (methoxyimino) butanoate synthesized in accordance with the method described in German Patent Application No. 3220524 in 10 ml of dichloromethane, 2.36 g of triethylamine and p-toluenesulfonyl chloride. 14 g and 4-dimethylaminopyridine 0.34 g were added sequentially. After the addition was complete, the reaction mixture was stirred overnight at room temperature. After completion of the reaction, 20 ml of saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was extracted with 30 ml of ethyl acetate. The obtained organic layer was washed with water, then washed and dried with saturated brine and then anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (5: 1) to obtain 0.8 g of the desired product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 7.78 (d, J = 8.1 Hz, 2H), 7.32 (d, J = 8.1 Hz, 2H), 5.31 (q, J = 6.9 Hz, 1 H), 4.28-4.16 (m, 2 H), 3.82 (s, 3 H), 2.44 (s, 3 H), 1.53 (d, J = 6.9 Hz) , 3H), 1.27 (t, J = 7.2 Hz, 3H)
　工程２：エチル　２－（メトキシイミノ）－３－（メチルチオ）ブタノエートの製造（化合物Ｅ－００１）
　エチル　２－（メトキシイミノ）－３－（トシルオキシ）ブタノエート０．８ｇのＮ，Ｎ－ジメチルホルムアミド５ｍｌ溶液に、０℃にてメチルメルカプタンナトリウム０．２ｇを添加した。添加終了後、同温度にて３０分撹拌した。反応終了後、該反応溶液に水１０ｍｌを添加し、酢酸エチル１０ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥した後、減圧下にて溶媒を留去し、目的物０．４５ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．３２（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），３．８７（ｓ，３Ｈ），３．６０（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），２．０５（ｓ，３Ｈ），１．４６（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）, １．３３（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　工程３：２－（メトキシイミノ）－３－（メチルチオ）ブタン酸の製造（化合物Ｆ－００１）
　エチル　２－（メトキシイミノ）－３－（メチルチオ）ブタノエート０．４５ｇのエタノール５ｍｌ溶液に、１Ｎ水酸化ナトリウム水溶液３．３ｍｌを添加した。。添加終了後、室温にて２時間撹拌した。反応終了後、該反応溶液から減圧下にてエタノールを留去した。得られた残留物を酢酸エチルで洗浄した。洗浄終了後、１Ｎ塩酸水溶液でｐＨ３とした後、酢酸エチル５ｍｌ（ｘ２）にて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥した後、減圧下にて溶媒を留去し、目的物０．４ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０６（ｓ，３Ｈ），３．８８－３．７７（ｍ，１Ｈ），２．０６（ｓ，３Ｈ），１．４９（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） Step 2: Preparation of ethyl 2- (methoxyimino) -3- (methylthio) butanoate (Compound E-001)
To a solution of 0.8 g of ethyl 2- (methoxyimino) -3- (tosyloxy) butanoate in 5 ml of N, N-dimethylformamide was added 0.2 g of sodium methyl mercaptan at 0 ° C. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction solution and extracted with 10 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.45 g of the desired product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.32 (q, J = 7.2 Hz, 2H), 3.87 (s, 3H), 3.60 (q, J = 7.2 Hz, 1H) ), 2.05 (s, 3H), 1.46 (d, J = 7.2 Hz, 3H), 1.33 (t, J = 7.2 Hz, 3H)
Step 3: Production of 2- (methoxyimino) -3- (methylthio) butanoic acid (Compound F-001)
To a solution of ethyl 5- (methoxyimino) -3- (methylthio) butanoate (0.45 g) in ethanol (5 ml) was added 1N aqueous sodium hydroxide solution (3.3 ml). . After completion of the addition, the mixture was stirred at room temperature for 2 hours. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure. The resulting residue was washed with ethyl acetate. After the completion of washing, the pH was adjusted to 3 with a 1N aqueous hydrochloric acid solution, followed by extraction with 5 ml (x2) of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.4 g of the objective product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.06 (s, 3H), 3.88-3.77 (m, 1H), 2.06 (s, 3H), 1.49 (d, J = 6.9 Hz, 3H) (The proton peak of CO 2 H was not observed.)
　また、参考例５と同様の合成法にて、以下の中間体を合成した。
　Ａ－００２；メチル　２－（ヒドロキシイミノ）－３－オキソペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．５１（ｂｒｓ，１Ｈ），３．９１（ｓ，３Ｈ），２．８１（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ），１．１３（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ａ－００３；メチル　２－（ヒドロキシイミノ）－４－メチル－３－オキソペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．２０（ｂｒｓ，１Ｈ），３．９１（ｓ，３Ｈ），３．４４－３．３０（ｍ，１Ｈ），１．２２－１．０８（ｍ，６Ｈ）
　Ｂ－００２；メチル　２－（メトキシイミノ）－３－オキソペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０９（ｓ，３Ｈ），３．８７（ｓ，３Ｈ），２．８１（ｑ，Ｊ＝７．５Ｈｚ，２Ｈ），１．１３（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｂ－００３；メチル　２－（メトキシイミノ）－４－メチル－３－オキソペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０９（ｓ，３Ｈ），３．８７（ｓ，３Ｈ），３．４３（ｓｅｐ，Ｊ＝７．２Ｈｚ，１Ｈ），１．１６（ｄ，Ｊ＝７．２Ｈｚ，６Ｈ） Further, the following intermediate was synthesized by the same synthesis method as in Reference Example 5.
A-002; methyl 2- (hydroxyimino) -3-oxopentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ9.51 (brs, 1H), 3.91 (s, 3H), 2.81 (q, J = 7.5 Hz, 2H), 1.13 ( t, J = 7.5Hz, 3H)
A-003; methyl 2- (hydroxyimino) -4-methyl-3-oxopentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.20 (brs, 1H), 3.91 (s, 3H), 3.44-3.30 (m, 1H), 1.22-1. 08 (m, 6H)
B-002; Methyl 2- (methoxyimino) -3-oxopentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.09 (s, 3H), 3.87 (s, 3H), 2.81 (q, J = 7.5 Hz, 2H), 1.13 ( t, J = 7.5Hz, 3H)
B-003; Methyl 2- (methoxyimino) -4-methyl-3-oxopentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.09 (s, 3H), 3.87 (s, 3H), 3.43 (sep, J = 7.2 Hz, 1H), 1.16 ( d, J = 7.2 Hz, 6H)
　Ｃ－００２；メチル　３－ヒドロキシ－２－（メトキシイミノ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．４２－４．３２（ｍ，１Ｈ），３．９１（ｓ，３Ｈ），３．８６（ｓ，３Ｈ），２．４４－２．３２（ｍ，１Ｈ），１．８７－１．５２（ｍ，２Ｈ），０．９９（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｃ－００３；メチル　３－ヒドロキシ－２－（メトキシイミノ）－４－メチルペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．１７（ｄｄ，Ｊ＝５．７，５．４Ｈｚ，１Ｈ），３．９２（ｓ，３Ｈ），３．８５（ｓ，３Ｈ），２．４５（ｄ，Ｊ＝５．７Ｈｚ，１Ｈ），１．９０（ｔｔｄ，Ｊ＝６．９，６．９，５．４Ｈｚ，１Ｈ），１．０１（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ），０．９７（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）
　Ｄ－００２；メチル　２－（メトキシイミノ）－３－（トシルオキシ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ７．８０（ｄ，Ｊ＝８．７Ｈｚ，２Ｈ），７．３３（ｄ，Ｊ＝８．７Ｈｚ，２Ｈ），５．０２（ｔ，Ｊ＝７．２Ｈｚ，１Ｈ），３．８０（ｓ，３Ｈ），３．７６（ｓ，３Ｈ），２．４５（ｓ，３Ｈ），２．００－１．８８（ｍ，２Ｈ），０．９２（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｄ－００３；メチル　２－（メトキシイミノ）－４－メチル－３－（トシルオキシ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ７．７９（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），７．３２（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），４．７１（ｄ，Ｊ＝９．６Ｈｚ，１Ｈ），３．７６（ｓ，３Ｈ），３．７５（ｓ，３Ｈ），２．４４（ｓ，３Ｈ），２．２０－２．０６（ｍ，１Ｈ），１．００（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ），０．９２（ｄ，Ｊ＝６．６Ｈｚ，３Ｈ） C-002; methyl 3-hydroxy-2- (methoxyimino) pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.42-4.32 (m, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 2.44-2. 32 (m, 1H), 1.87-1.52 (m, 2H), 0.99 (t, J = 7.5 Hz, 3H)
C-003; methyl 3-hydroxy-2- (methoxyimino) -4-methylpentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.17 (dd, J = 5.7, 5.4 Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.45 (d, J = 5.7 Hz, 1H), 1.90 (ttd, J = 6.9, 6.9, 5.4 Hz, 1H), 1.01 (d, J = 6.9 Hz, 3H), 0.97 (d, J = 6.9 Hz, 3H)
D-002; methyl 2- (methoxyimino) -3- (tosyloxy) pentanoate
1 H NMR (CDCl 3, Me 4 Si, 300MHz) δ7.80 (d, J = 8.7Hz, 2H), 7.33 (d, J = 8.7Hz, 2H), 5.02 (t, J = 7.2 Hz, 1H), 3.80 (s, 3H), 3.76 (s, 3H), 2.45 (s, 3H), 2.00-1.88 (m, 2H),. 92 (t, J = 7.5Hz, 3H)
D-003; methyl 2- (methoxyimino) -4-methyl-3- (tosyloxy) pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 7.79 (d, J = 7.8 Hz, 2H), 7.32 (d, J = 7.8 Hz, 2H), 4.71 (d, J = 9.6 Hz, 1 H), 3.76 (s, 3 H), 3.75 (s, 3 H), 2.44 (s, 3 H), 2.20-2.06 (m, 1 H), 1. 00 (d, J = 6.9 Hz, 3H), 0.92 (d, J = 6.6 Hz, 3H)
　Ｅ－００２；メチル　２－（メトキシイミノ）－３－（メチルチオ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．８９（ｓ，３Ｈ），３．８４（ｓ，３Ｈ），３．３３（ｔ，Ｊ＝７．５Ｈｚ，１Ｈ），２．０４（ｓ，３Ｈ），１．９３－１．６０（ｍ，２Ｈ），１．０５（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｅ－００３；メチル　２－（メトキシイミノ）－４－メチル－３－（メチルチオ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．８９（ｓ，３Ｈ），３．８４（ｓ，３Ｈ），３．０８（ｄ，Ｊ＝１０．５Ｈｚ，１Ｈ），２．０８－１．９２（ｍ，１Ｈ），２．０６（ｓ，３Ｈ），１．１５－１．０４（ｍ，６Ｈ）
　Ｆ－００２；２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０３（ｓ，３Ｈ），３．５３（ｔ，Ｊ＝７．８Ｈｚ，１Ｈ），２．０４（ｓ，３Ｈ），１．９６－１．７０（ｍ，２Ｈ），１．０４（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
　Ｅ－００６；メチル　３－メトキシ－２－（メトキシイミノ）ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．９１（ｓ，３Ｈ），３．８４（ｓ，３Ｈ），３．７５（ｔ，Ｊ＝７．２Ｈｚ，１Ｈ），３．３７（ｓ，３Ｈ），１．８８－１．６２（ｍ，２Ｈ），０．９７（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ） E-002; methyl 2- (methoxyimino) -3- (methylthio) pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.89 (s, 3H), 3.84 (s, 3H), 3.33 (t, J = 7.5 Hz, 1H), 2.04 ( s, 3H), 1.93-1.60 (m, 2H), 1.05 (t, J = 7.5 Hz, 3H)
E-003; methyl 2- (methoxyimino) -4-methyl-3- (methylthio) pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.89 (s, 3H), 3.84 (s, 3H), 3.08 (d, J = 10.5 Hz, 1H), 2.08- 1.92 (m, 1H), 2.06 (s, 3H), 1.15-1.04 (m, 6H)
F-002; 2- (methoxyimino) -3- (methylthio) pentanoic acid
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.03 (s, 3H), 3.53 (t, J = 7.8 Hz, 1H), 2.04 (s, 3H), 1.96- 1.70 (m, 2H), 1.04 (t, J = 7.2 Hz, 3H) (The proton peak of CO 2 H was not observed.)
E-006; Methyl 3-methoxy-2- (methoxyimino) pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.91 (s, 3H), 3.84 (s, 3H), 3.75 (t, J = 7.2 Hz, 1H), 3.37 ( s, 3H), 1.88-1.62 (m, 2H), 0.97 (t, J = 7.5 Hz, 3H)
　Ｅ－００８；メチル　２－（メトキシイミノ）－３－［｛５－（トリフルオロメチル）ピリジン－２－イル｝チオ］ペンタノエート（２種の異性体混合物　異性体比７：３）
異性体比７
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．６７－８．６２（ｍ，１Ｈ），７．６８（ｄｄ，Ｊ＝８．４，２．４Ｈｚ，１Ｈ），７．３１－７．１９（ｍ，１Ｈ），４．８６（ｔ，Ｊ＝７．５Ｈｚ，１Ｈ），３．９０（ｓ，３Ｈ），３．７８（ｓ，３Ｈ），２．１４－１．８０（ｍ，２Ｈ），１．１０（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．６７－８．６２（ｍ，１Ｈ），７．６８（ｄｄ，Ｊ＝８．４，２．４Ｈｚ，１Ｈ），７．３１－７．１９（ｍ，１Ｈ），５．５３（ｔ，Ｊ＝８．１Ｈｚ，１Ｈ），４．１０（ｓ，３Ｈ），３．８８（ｓ，３Ｈ），２．１４－１．８０（ｍ，２Ｈ），１．０１（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｅ－００９；メチル　２－（メトキシイミノ）－３－｛（２，２，２－トリフルオロエチル）チオ｝ペンタノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．９１（ｓ，３Ｈ），３．８５（ｓ，３Ｈ），３．６５－３．５５（ｍ，１Ｈ），３．２５－２．９３（ｍ，２Ｈ），１．９０－１．６０（ｍ，２Ｈ），１．０７（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）
　Ｅ－０１０；エチル　２－（メトキシイミノ）－３－（メチルスルホニル）－５－ヘキセノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．７４－５．５８（ｍ，１Ｈ），５．２０－５．０７（ｍ，２Ｈ），４．９２（ｄｄ，Ｊ＝１０．８，５．４Ｈｚ，１Ｈ），４．３４（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．１４（ｓ，３Ｈ），３．１６－２．８７（ｍ，２Ｈ），２．９９（ｓ，３Ｈ），１．３６（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ） E-008; methyl 2- (methoxyimino) -3-[{5- (trifluoromethyl) pyridin-2-yl} thio] pentanoate (mixture of two isomers, isomer ratio 7: 3)
Isomeric ratio 7
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.67-8.62 (m, 1H), 7.68 (dd, J = 8.4, 2.4 Hz, 1H), 7.31-7 .19 (m, 1H), 4.86 (t, J = 7.5 Hz, 1H), 3.90 (s, 3H), 3.78 (s, 3H), 2.14-1.80 (m , 2H), 1.10 (t, J = 7.2 Hz, 3H)
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.67-8.62 (m, 1H), 7.68 (dd, J = 8.4, 2.4 Hz, 1H), 7.31-7 .19 (m, 1H), 5.53 (t, J = 8.1 Hz, 1H), 4.10 (s, 3H), 3.88 (s, 3H), 2.14-1.80 (m , 2H), 1.01 (t, J = 7.5 Hz, 3H)
E-009; methyl 2- (methoxyimino) -3-{(2,2,2-trifluoroethyl) thio} pentanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.91 (s, 3H), 3.85 (s, 3H), 3.65-3.55 (m, 1H), 3.25-2. 93 (m, 2H), 1.90-1.60 (m, 2H), 1.07 (t, J = 7.2 Hz, 3H)
E-010; ethyl 2- (methoxyimino) -3- (methylsulfonyl) -5-hexenoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.74-5.58 (m, 1H), 5.20-5.07 (m, 2H), 4.92 (dd, J = 10.8 , 5.4 Hz, 1H), 4.34 (q, J = 7.2 Hz, 2H), 4.14 (s, 3H), 3.16-2.87 (m, 2H), 2.99 (s) , 3H), 1.36 (t, J = 7.2 Hz, 3H)
　Ｅ－０１１；エチル　２－（メトキシイミノ）－３－（メチルスルホニル）－５－ヘキシノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．０４（ｄｄ，Ｊ＝９．６，６．６Ｈｚ，１Ｈ），４．４６－４．３２（ｍ，２Ｈ），４．１７（ｓ，３Ｈ），３．３３－３．０７（ｍ，２Ｈ），３．００（ｓ，３Ｈ），２．０８（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ），１．４４－１．３０（ｍ，３Ｈ）
　Ｅ－０１２；メチル　３－（アリルチオ）－２－（メトキシイミノ）ペンタノエート（２種の異性体混合物　異性体比７：３）
異性体比７
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．８５－５．６６（ｍ，１Ｈ），５．１８－５．０２（ｍ，２Ｈ），３．８７（ｓ，３Ｈ），３．８３（ｓ，３Ｈ），３．４３－３．０２（ｍ，２Ｈ），２．６５－２．４５（ｍ，１Ｈ），２．０５－１．６０（ｍ，２Ｈ），１．３０－０．８７（ｍ，３Ｈ）
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．８５－５．６６（ｍ，１Ｈ），５．１８－５．０２（ｍ，２Ｈ），４．００（ｓ，３Ｈ），３．８３（ｓ，３Ｈ），３．４３－３．０２（ｍ，２Ｈ），２．６５－２．４５（ｍ，１Ｈ），２．０５－１．６０（ｍ，２Ｈ），１．３０－０．８７（ｍ，３Ｈ）
　Ｆ－００２；２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０３（ｓ，３Ｈ），３．５３（ｔ，Ｊ＝７．８Ｈｚ，１Ｈ），２．０４（ｓ，３Ｈ），１．９６－１．７０（ｍ，２Ｈ），１．０４（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） E-011; ethyl 2- (methoxyimino) -3- (methylsulfonyl) -5-hexinoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.04 (dd, J = 9.6, 6.6 Hz, 1H), 4.46-4.32 (m, 2H), 4.17 (s , 3H), 3.33-3.07 (m, 2H), 3.00 (s, 3H), 2.08 (t, J = 2.4 Hz, 1H), 1.44-1.30 (m , 3H)
E-012; methyl 3- (allylthio) -2- (methoxyimino) pentanoate (mixture of two isomers, isomer ratio 7: 3)
Isomeric ratio 7
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.85-5.66 (m, 1H), 5.18-5.02 (m, 2H), 3.87 (s, 3H), 3. 83 (s, 3H), 3.43-3.02 (m, 2H), 2.65-2.45 (m, 1H), 2.05-1.60 (m, 2H), 1.30- 0.87 (m, 3H)
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.85-5.66 (m, 1H), 5.18-5.02 (m, 2H), 4.00 (s, 3H), 3. 83 (s, 3H), 3.43-3.02 (m, 2H), 2.65-2.45 (m, 1H), 2.05-1.60 (m, 2H), 1.30- 0.87 (m, 3H)
F-002; 2- (methoxyimino) -3- (methylthio) pentanoic acid
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.03 (s, 3H), 3.53 (t, J = 7.8 Hz, 1H), 2.04 (s, 3H), 1.96- 1.70 (m, 2H), 1.04 (t, J = 7.2 Hz, 3H) (The proton peak of CO 2 H was not observed.)
　Ｆ－００３；２－（メトキシイミノ）－４－メチル－３－（メチルチオ）ペンタン酸（２種の異性体混合物　異性体比５５：４５）
異性体比５５
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．１５（ｄ，Ｊ＝６．９Ｈｚ，１Ｈ），４．１０（ｓ，３Ｈ），２．２０－２．０１（ｍ，１Ｈ），２．０５（ｓ，３Ｈ），１．０１（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ），０．９５（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
異性体比４５
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０３（ｓ，３Ｈ），３．２３（ｄ，Ｊ＝１０．５Ｈｚ，１Ｈ），２．２０－２．０１（ｍ，１Ｈ），２．０５（ｓ，３Ｈ），１．１５（ｄ，Ｊ＝６．６Ｈｚ，３Ｈ），１．０２（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
　Ｆ－００６；３－メトキシ－２－（メトキシイミノ）ペンタン酸
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０２（ｓ，３Ｈ），３．８９（ｔ，Ｊ＝７．２Ｈｚ，１Ｈ），３．４０（ｓ，３Ｈ），１．９２－１．７０（ｍ，２Ｈ），０．９４（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
　Ｆ－００８；２－（メトキシイミノ）－３－［｛５－（トリフルオロメチル）ピリジン－２－イル｝チオ］ペンタン酸
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．７０－８．６０（ｍ，１Ｈ），７．７５－７．６３（ｍ，１Ｈ），７．３０－７．２０（ｍ，１Ｈ），５．４４（ｔ，Ｊ＝７．８Ｈｚ，１Ｈ），４．１２（ｓ，３Ｈ），２．２０－１．９５（ｍ，２Ｈ），１．００（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｆ－００９；２－（メトキシイミノ）－３－｛（２，２，２－トリフルオロエチル）チオ｝ペンタン酸
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０７（ｓ，３Ｈ），３．７８－３．７０（ｍ，１Ｈ），３．３０－２．９７（ｍ，２Ｈ），２．０３－１．７０（ｍ，２Ｈ），１．０５（ｔ，Ｊ＝７．２Ｈｚ，３Ｈ） F-003; 2- (methoxyimino) -4-methyl-3- (methylthio) pentanoic acid (mixture of two isomers, isomer ratio 55:45)
Isomeric ratio 55
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.15 (d, J = 6.9 Hz, 1H), 4.10 (s, 3H), 2.20-2.01 (m, 1H), 2.05 (s, 3H), 1.01 (d, J = 6.9 Hz, 3H), 0.95 (d, J = 6.9 Hz, 3H) (CO 2 H proton peak was not observed .)
Isomeric ratio 45
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.03 (s, 3H), 3.23 (d, J = 10.5 Hz, 1H), 2.20-2.01 (m, 1H), 2.05 (s, 3H), 1.15 (d, J = 6.6 Hz, 3H), 1.02 (d, J = 6.9 Hz, 3H) (CO 2 H proton peak was not observed .)
F-006; 3-methoxy-2- (methoxyimino) pentanoic acid
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.02 (s, 3H), 3.89 (t, J = 7.2 Hz, 1H), 3.40 (s, 3H), 1.92− 1.70 (m, 2H), 0.94 (t, J = 7.2 Hz, 3H) (The proton peak of CO 2 H was not observed.)
F-008; 2- (methoxyimino) -3-[{5- (trifluoromethyl) pyridin-2-yl} thio] pentanoic acid
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.70-8.60 (m, 1H), 7.75-7.63 (m, 1H), 7.30-7.20 (m, 1H) ), 5.44 (t, J = 7.8 Hz, 1H), 4.12 (s, 3H), 2.20-1.95 (m, 2H), 1.00 (t, J = 7.5 Hz) , 3H)
F-009; 2- (methoxyimino) -3-{(2,2,2-trifluoroethyl) thio} pentanoic acid
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.07 (s, 3H), 3.78-3.70 (m, 1H), 3.30-2.97 (m, 2H), 2. 03-1.70 (m, 2H), 1.05 (t, J = 7.2 Hz, 3H)
　Ｆ－０１０；２－（メトキシイミノ）－３－（メチルスルホニル）－５－ヘキセン酸（２種の異性体混合物　異性体比３：２）
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．８２－５．５６（ｍ，１Ｈ），５．２５－５．１０（ｍ，２Ｈ），４．８５（ｄｄ，Ｊ＝１１．１，４．８Ｈｚ，１Ｈ），４．１８（ｓ，３Ｈ），３．２９－２．７８（ｍ，２Ｈ），３．０４（ｓ，３Ｈ）
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．８２－５．５６（ｍ，１Ｈ），５．２５－５．１０（ｍ，２Ｈ），４．４５（ｄｄ，Ｊ＝１０．８，４．８Ｈｚ，１Ｈ），４．１８（ｓ，３Ｈ），３．２９－２．７８（ｍ，２Ｈ），２．９５（ｓ，３Ｈ）
Ｆ－０１１；２－（メトキシイミノ）－３－（メチルスルホニル）－５－ヘキシン酸（２種の異性体混合物　異性体比３：２）
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．９８（ｄｄ，Ｊ＝１０．２，６．６Ｈｚ，１Ｈ），４．２１（ｓ，３Ｈ），３．３８－３．２５（ｍ，１Ｈ），３．２０－２．９６（ｍ，１Ｈ），３．０４（ｓ，３Ｈ），２．１４－２．０６（ｍ，１Ｈ）
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．７３－４．６７（ｍ，１Ｈ），４．２３（ｓ，３Ｈ），３．６５－３．４８（ｍ，１Ｈ），３．２０－２．９６（ｍ，１Ｈ），３．０６（ｓ，３Ｈ），２．１８（ｔ，Ｊ＝２．４Ｈｚ，１Ｈ）。
　Ｆ－０１２；３－（アリルチオ）－２－（メトキシイミノ）ペンタン酸（２種の異性体混合物　異性体比７：３）
異性体比７
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．９０－５．７０（ｍ，１Ｈ），５．２２－５．０６（ｍ，２Ｈ），４．０２（ｓ，３Ｈ），３．６０－３．０４（ｍ，２Ｈ），２．７０－２．４８（ｍ，１Ｈ），２．１０－１．７２（ｍ，２Ｈ），１．０８－０．８５（ｍ，３Ｈ）
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ５．９０－５．７０（ｍ，１Ｈ），５．２２－５．０６（ｍ，２Ｈ），４．０５（ｓ，３Ｈ），３．６０－３．０４（ｍ，２Ｈ），２．７０－２．４８（ｍ，１Ｈ），２．１０－１．７２（ｍ，２Ｈ），１．０８－０．８５（ｍ，３Ｈ） F-010; 2- (methoxyimino) -3- (methylsulfonyl) -5-hexenoic acid (mixture of two isomers, isomer ratio 3: 2)
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.82-5.56 (m, 1H), 5.25-5.10 (m, 2H), 4.85 (dd, J = 11.1 , 4.8 Hz, 1H), 4.18 (s, 3H), 3.29-2.78 (m, 2H), 3.04 (s, 3H)
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.82-5.56 (m, 1H), 5.25-5.10 (m, 2H), 4.45 (dd, J = 10.8 , 4.8 Hz, 1H), 4.18 (s, 3H), 3.29-2.78 (m, 2H), 2.95 (s, 3H)
F-011; 2- (methoxyimino) -3- (methylsulfonyl) -5-hexynoic acid (mixture of two isomers, isomer ratio 3: 2)
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.98 (dd, J = 10.2, 6.6 Hz, 1H), 4.21 (s, 3H), 3.38-3.25 (m , 1H), 3.20-2.96 (m, 1H), 3.04 (s, 3H), 2.14-2.06 (m, 1H)
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.73-4.67 (m, 1H), 4.23 (s, 3H), 3.65-3.48 (m, 1H), 3. 20-2.96 (m, 1H), 3.06 (s, 3H), 2.18 (t, J = 2.4 Hz, 1H).
F-012; 3- (allylthio) -2- (methoxyimino) pentanoic acid (mixture of two isomers, isomer ratio 7: 3)
Isomeric ratio 7
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.90-5.70 (m, 1H), 5.22-5.06 (m, 2H), 4.02 (s, 3H), 3. 60-3.04 (m, 2H), 2.70-2.48 (m, 1H), 2.10-1.72 (m, 2H), 1.08-0.85 (m, 3H)
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 5.90-5.70 (m, 1H), 5.22-5.06 (m, 2H), 4.05 (s, 3H), 3. 60-3.04 (m, 2H), 2.70-2.48 (m, 1H), 2.10-1.72 (m, 2H), 1.08-0.85 (m, 3H)
　参考例６
　３－（エチルチオ）－２－（メトキシイミノ）ブタン酸の製造
　工程１：３－（エチルチオ）－２－オキソブタン酸の製造
　２－オキソ酪酸３ｇの１，２－ジクロロエタン２０ｍｌ溶液に、Ｎ－ブロモスクシンイミド６．８ｇ、及び２，２’－アゾビス（イソブチロニトリル）２４１ｍｇを順次添加し、反応容器中を窒素ガスで置換した後に、８０℃にて１時間撹拌した。反応終了後、該反応溶液を０℃に冷却し、アセトン１０ｍｌ、炭酸カリウム５．２ｇ、及びエチルメルカプタン　ナトリウム２．５ｇを順次添加し、室温にて１時間撹拌した。反応終了後、該反応溶液にヘキサン３０ｍｌ及び水３０ｍｌを添加し、分液操作にて水層を取り出した。得られた水層に、濃塩酸１０ｍｌを添加した後、酢酸エチル５０ｍｌにて抽出した。得られた有機層を、無水硫酸ナトリウムで脱水乾燥した後、減圧下にて溶媒を留去して目的物５ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．２５－４．１０（ｍ，１Ｈ），２．６０－２．３０（ｍ，２Ｈ），１．５０（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ），１．２２（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） Reference Example 6
Production of 3- (ethylthio) -2- (methoxyimino) butanoic acid Step 1: Production of 3- (ethylthio) -2-oxobutanoic acid N-bromosuccinimide in 20 ml of 1,2-dichloroethane in 3 g of 2-oxobutyric acid 6.8 g and 241 mg of 2,2′-azobis (isobutyronitrile) were sequentially added, and the reaction vessel was purged with nitrogen gas, followed by stirring at 80 ° C. for 1 hour. After completion of the reaction, the reaction solution was cooled to 0 ° C., 10 ml of acetone, 5.2 g of potassium carbonate, and 2.5 g of sodium ethyl mercaptan were sequentially added, followed by stirring at room temperature for 1 hour. After completion of the reaction, 30 ml of hexane and 30 ml of water were added to the reaction solution, and the aqueous layer was taken out by a liquid separation operation. To the obtained aqueous layer, 10 ml of concentrated hydrochloric acid was added, followed by extraction with 50 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 5 g of the desired product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.25-4.10 (m, 1H), 2.60-2.30 (m, 2H), 1.50 (d, J = 7.2 Hz) , 3H), 1.22 (t, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
　工程２：３－（エチルチオ）－２－（メトキシイミノ）ブタン酸の製造（化合物Ｆ－００４）
　３－（エチルチオ）－２－オキソブタン酸１ｇのメタノール１０ｍｌ及び水５ｍｌの溶液に、Ｏ－メチルヒドロキシルアミン　塩酸塩１ｇを添加し、室温にて１５時間撹拌した。反応終了後、該反応溶液に水酸化ナトリウム２ｇ、水１０ｍｌ、及びヘキサン１０ｍｌを順次添加し、分液操作にて水層を取り出した。得られた水層に濃塩酸を添加して、水層のｐＨを２とした後、塩化ナトリウム３ｇを添加し、酢酸エチル３０ｍｌにて抽出した。得られた有機層を、無水硫酸ナトリウムで脱水乾燥した後、減圧下にて溶媒を留去して目的物２５０ｍｇを黄色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は２：１であった。
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０６（ｓ，３Ｈ），４．２０－４．０５（ｍ，１Ｈ），２．６５－２．４５（ｍ，２Ｈ），１．５６（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ），１．２４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０１（ｓ，３Ｈ），３．９０－３．８０（ｍ，１Ｈ），２．６５－２．４５（ｍ，２Ｈ），１．５１（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ），１．２５（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） Step 2: Production of 3- (ethylthio) -2- (methoxyimino) butanoic acid (Compound F-004)
To a solution of 1 g of 3- (ethylthio) -2-oxobutanoic acid in 10 ml of methanol and 5 ml of water, 1 g of O-methylhydroxylamine hydrochloride was added and stirred at room temperature for 15 hours. After completion of the reaction, 2 g of sodium hydroxide, 10 ml of water and 10 ml of hexane were sequentially added to the reaction solution, and the aqueous layer was taken out by a liquid separation operation. Concentrated hydrochloric acid was added to the obtained aqueous layer to adjust the pH of the aqueous layer to 2, and then 3 g of sodium chloride was added and extracted with 30 ml of ethyl acetate. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 250 mg of the desired product as a yellow oil. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 2: 1.
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.06 (s, 3H), 4.20-4.05 (m, 1H), 2.65-2.45 (m, 2H), 1. 56 (d, J = 7.5 Hz, 3H), 1.24 (t, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.01 (s, 3H), 3.90-3.80 (m, 1H), 2.65-2.45 (m, 2H), 1. 51 (d, J = 7.5 Hz, 3H), 1.25 (t, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
　また、参考例６と同様の合成法にて、以下の中間体を合成した。
　Ｆ－００５；２－（エトキシイミノ）－３－（エチルチオ）ブタン酸（２種の異性体混合物　異性体比１：１）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．４０－４．２５（ｍ，２Ｈ），３．９０（ｑ，Ｊ＝７．５Ｈｚ，１Ｈ），２．６５－２．４５（ｍ，２Ｈ），１．５７（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ），１．３４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ），１．２４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．４５－４．３５（ｍ，１Ｈ），４．４０－４．２５（ｍ，２Ｈ），２．６５－２．４５（ｍ，２Ｈ），１．５２（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ），１．３４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ），１．２４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
　Ｆ－００１；２－（メトキシイミノ）－３－（メチルチオ）ブタン酸（２種の異性体混合物　異性体比１：１）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．２８（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），４．０６（ｓ，３Ｈ），２．１０（ｓ，３Ｈ），１．５６（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ３．９８（ｓ，３Ｈ），３．７５（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），２．０９（ｓ，３Ｈ），１．４９（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） Further, the following intermediate was synthesized by the same synthesis method as in Reference Example 6.
F-005; 2- (ethoxyimino) -3- (ethylthio) butanoic acid (mixture of two isomers, isomer ratio 1: 1)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.40-4.25 (m, 2H), 3.90 (q, J = 7.5 Hz, 1H), 2.65-2.45 (m , 2H), 1.57 (d, J = 7.5 Hz, 3H), 1.34 (t, J = 7.5 Hz, 3H), 1.24 (t, J = 7.5 Hz, 3H) (CO No 2 H proton peak was observed.)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.45-4.35 (m, 1H), 4.40-4.25 (m, 2H), 2.65-2.45 (m, 2H) ), 1.52 (d, J = 7.5 Hz, 3H), 1.34 (t, J = 7.5 Hz, 3H), 1.24 (t, J = 7.5 Hz, 3H) (CO 2 H No proton peak was observed.)
F-001; 2- (methoxyimino) -3- (methylthio) butanoic acid (mixture of two isomers, isomer ratio 1: 1)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.28 (q, J = 7.2 Hz, 1H), 4.06 (s, 3H), 2.10 (s, 3H), 1.56 ( d, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 3.98 (s, 3H), 3.75 (q, J = 7.2 Hz, 1H), 2.09 (s, 3H), 1.49 ( d, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
　参考例７
　２－（メトキシイミノ）－Ｎ－（３－メチル－１Ｈ－ピラゾール－４－イル）－３－（メチルチオ）ブタンアミドの製造
　工程１：１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－カルボン酸の製造
　ジャーナル　オブ　ヘテロサイクリック　ケミストリー　１９８７年，２４巻，６９３頁に記載の方法に従って合成したエチル　１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－カルボキシレート１６．７ｇのエタノール５０ｍｌ及び水５０ｍｌの溶液に、水酸化ナトリウム３．５ｇを添加し、室温にて一晩撹拌した後、６０℃にて３時間撹拌した。反応終了後、減圧下にて該反応溶液の溶媒を留去した後、残留物に水５０ｍｌを添加し、酢酸エチル５０ｍｌで洗浄した。得られた水層に濃塩酸を添加してｐＨを１とし、水層中に析出した固体を濾過にて取り出し、水洗した。得られた固体を減圧下にて乾燥し、目的物９．０ｇを白色固体として得た。
融点；１０８～１０９℃
　工程２：１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－カルボキサミドの製造
　１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－カルボン酸１ｇのジクロロメタン１０ｍｌ溶液に、室温にてオキサリルクロリド０．８４ｇ、次いでＮ，Ｎ－ジメチルホルムアミド０．１ｍｌの順に添加した。添加終了後、同温度にて３０分間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物にテトラヒドロフラン１５ｍｌを添加し、０℃にて２８重量％アンモニア水溶液１５ｍｌに添加した。添加終了後、０℃にて３０分間撹拌を継続した。反応終了後、該反応溶液を酢酸エチル３０ｍｌにて抽出した後、減圧下にて溶媒を留去し、目的物０．４８ｇを白色固体として得た。
融点；１３７～１４０℃ Reference Example 7
Preparation of 2- (methoxyimino) -N- (3-methyl-1H-pyrazol-4-yl) -3- (methylthio) butanamide Step 1: 1- (tert-Butyl) -5-methyl-1H-pyrazole- Preparation of 4-carboxylic acid Ethyl 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxylate synthesized according to the method described in Journal of Heterocyclic Chemistry 1987, 24, 693. Sodium hydroxide (3.5 g) was added to a solution of 7 g of ethanol (50 ml) and water (50 ml), stirred at room temperature overnight, and then stirred at 60 ° C. for 3 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure, 50 ml of water was added to the residue, and the mixture was washed with 50 ml of ethyl acetate. Concentrated hydrochloric acid was added to the obtained aqueous layer to adjust the pH to 1, and the solid deposited in the aqueous layer was taken out by filtration and washed with water. The obtained solid was dried under reduced pressure to obtain 9.0 g of the objective product as a white solid.
Melting point: 108-109 ° C
Step 2: Preparation of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxamide 1 g of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxylic acid was added to a 10 ml solution of dichloromethane. At room temperature, 0.84 g of oxalyl chloride and then 0.1 ml of N, N-dimethylformamide were added in this order. After completion of the addition, the mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. Tetrahydrofuran (15 ml) was added to the obtained residue, and added at 0 ° C. to a 28 wt% aqueous ammonia solution (15 ml). After completion of the addition, stirring was continued at 0 ° C. for 30 minutes. After completion of the reaction, the reaction solution was extracted with 30 ml of ethyl acetate, and then the solvent was distilled off under reduced pressure to obtain 0.48 g of the desired product as a white solid.
Melting point: 137-140 ° C
　工程３：１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－アミンの製造
　水酸化ナトリウム０．６４ｇの水０．５ｍｌ溶液に、８重量％次亜塩素酸ナトリウム水溶液５．２ｇ及び水２ｍｌを添加し、０℃に冷却した。該反応溶液に１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－カルボキサミド０．４８ｇを添加し、７０℃にて３時間撹拌した。反応終了後、該反応溶液を室温まで冷却した後、酢酸エチル１０ｍｌで抽出した。得られた有機層を、無水硫酸ナトリウムで乾燥し、減圧下にて溶媒を留去した後、目的物０．２３ｇを茶褐色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ７．１１（ｓ，１Ｈ），２．６３（ｂｒｓ，２Ｈ），２．３３（ｓ，３Ｈ），１．５８（ｓ，９Ｈ）
　工程４：Ｎ－｛１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミドの製造
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸０．４ｇのジクロロメタン５ｍｌ溶液に、室温にてオキサリルクロリド０．３８ｇ、次いでＮ，Ｎ－ジメチルホルムアミド０．１ｍｌの順に添加した。添加終了後、同温度にて１時間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物を、別途調製した１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－アミン０．２３ｇ及びピリジン０．３６ｇのジクロロメタン５ｍｌ溶液に０℃にて添加した。添加終了後、０℃にて１時間撹拌を継続した。反応終了後、該反応溶液を水１０ｍｌにて洗浄した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（１：１）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．３４ｇを茶褐色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ７．９７（ｂｒｓ，１Ｈ），７．６１（ｓ，１Ｈ），４．３４（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），４．０２（ｓ，３Ｈ），２．３４（ｓ，３Ｈ），２．１５（ｓ，３Ｈ），１．６３（ｓ，９Ｈ），１．６２（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ） Step 3: Preparation of 1- (tert-butyl) -5-methyl-1H-pyrazol-4-amine 5.2 g of 8 wt% aqueous sodium hypochlorite solution in 0.5 ml of water of 0.64 g of sodium hydroxide And 2 ml of water were added and cooled to 0 ° C. To the reaction solution, 0.48 g of 1- (tert-butyl) -5-methyl-1H-pyrazole-4-carboxamide was added and stirred at 70 ° C. for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with 10 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 0.23 g of the desired product was obtained as a brown oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 7.11 (s, 1H), 2.63 (brs, 2H), 2.33 (s, 3H), 1.58 (s, 9H)
Step 4: Preparation of N- {1- (tert-butyl) -5-methyl-1H-pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide 2- (methoxyimino) -3 To a solution of 0.4 g of (methylthio) butanoic acid in 5 ml of dichloromethane was added 0.38 g of oxalyl chloride and then 0.1 ml of N, N-dimethylformamide at room temperature. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was added at 0 ° C. to a separately prepared solution of 0.23 g of 1- (tert-butyl) -5-methyl-1H-pyrazol-4-amine and 0.36 g of pyridine in 5 ml of dichloromethane. After completion of the addition, stirring was continued for 1 hour at 0 ° C. After completion of the reaction, the reaction solution was washed with 10 ml of water. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (1: 1) to obtain 0.34 g of the desired product as a brown oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 7.97 (brs, 1H), 7.61 (s, 1H), 4.34 (q, J = 7.2 Hz, 1H), 4.02 ( s, 3H), 2.34 (s, 3H), 2.15 (s, 3H), 1.63 (s, 9H), 1.62 (d, J = 7.2 Hz, 3H)
　工程５：２－（メトキシイミノ）－Ｎ－（３－メチル－１Ｈ－ピラゾール－４－イル）－３－（メチルチオ）ブタンアミドの製造
　Ｎ－｛１－（ｔｅｒｔ－ブチル）－５－メチル－１Ｈ－ピラゾール－４－イル｝－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド０．３４ｇのギ酸５ｍｌ溶液を、ギ酸の還流温度にて５時間撹拌した。反応終了後、該反応溶液に水５ｍｌを添加し、酢酸エチル５ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた残留物を、酢酸エチルにて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物８６ｍｇを薄黄色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は３：１であった。
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．２１（ｂｒｓ，１Ｈ），８．０２（ｓ，１Ｈ），５．７５（ｂｒｓ，１Ｈ），４．３６（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），４．０４（ｓ，３Ｈ），２．２９（ｓ，３Ｈ），２．１５（ｓ，３Ｈ），１．６２（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．８０（ｂｒｓ，１Ｈ），８．０６（ｓ，１Ｈ），５．７５（ｂｒｓ，１Ｈ），４．３６（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），４．０４（ｓ，３Ｈ），２．２７（ｓ，３Ｈ），２．１０（ｓ，３Ｈ），１．５１（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ） Step 5: Preparation of 2- (methoxyimino) -N- (3-methyl-1H-pyrazol-4-yl) -3- (methylthio) butanamide N- {1- (tert-butyl) -5-methyl-1H A solution of 0.34 g of -pyrazol-4-yl} -2- (methoxyimino) -3- (methylthio) butanamide in 5 ml of formic acid was stirred at the reflux temperature of formic acid for 5 hours. After completion of the reaction, 5 ml of water was added to the reaction solution and extracted with 5 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with ethyl acetate to obtain 86 mg of the desired product as a pale yellow oil. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 3: 1.
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.21 (brs, 1H), 8.02 (s, 1H), 5.75 (brs, 1H), 4.36 (q, J = 7. 2 Hz, 1 H), 4.04 (s, 3 H), 2.29 (s, 3 H), 2.15 (s, 3 H), 1.62 (d, J = 7.2 Hz, 3 H)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.80 (brs, 1H), 8.06 (s, 1H), 5.75 (brs, 1H), 4.36 (q, J = 7. 2 Hz, 1 H), 4.04 (s, 3 H), 2.27 (s, 3 H), 2.10 (s, 3 H), 1.51 (d, J = 7.2 Hz, 3 H)
　参考例８
　Ｎ－（３－クロロ－１Ｈ－ピラゾール－４－イル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミドの製造
　２－（メトキシイミノ）－３－（メチルチオ）ブタン酸１ｇのジクロロメタン１５ｍｌ溶液に、室温にてオキサリルクロリド１．４ｇ、次いでＮ，Ｎ－ジメチルホルムアミド０．２ｍｌの順に添加した。添加終了後、同温度にて１時間撹拌した。反応終了後、減圧下にて溶媒を留去した。得られた残留物を、別途調製した３－クロロ－１Ｈ－ピラゾール－４－アミン０．９ｇ及びピリジン１．４ｇのジクロロメタン２０ｍｌ溶液に室温にて添加した。添加終了後、１晩撹拌を継続した。反応終了後、該反応溶液から減圧下にて溶媒を留去した。得られた残留物に１Ｎ　塩酸水溶液２０ｍｌを添加し、酢酸エチル２０ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した後、目的物１．２ｇを黄色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は２：１であった。
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．５２（ｂｒｓ，１Ｈ），８．２６（ｓ，１Ｈ），４．３７－４．３１（ｍ，１Ｈ）４．０７（ｓ，３Ｈ），２．１４（ｓ，３Ｈ），１．６２（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ）
異性体比１
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．５２（ｂｒｓ，１Ｈ），８．５０（ｓ，１Ｈ），４．３７－４．３１（ｍ，１Ｈ）４．０７（ｓ，３Ｈ），２．１７（ｓ，３Ｈ），１．５８（ｄ，Ｊ＝７．５Ｈｚ，３Ｈ） Reference Example 8
Preparation of N- (3-chloro-1H-pyrazol-4-yl) -2- (methoxyimino) -3- (methylthio) butanamide 2- (methoxyimino) -3- (methylthio) butanoic acid 1 g in dichloromethane 15 ml solution At room temperature was added 1.4 g of oxalyl chloride and then 0.2 ml of N, N-dimethylformamide. After completion of the addition, the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was added at room temperature to a separately prepared solution of 0.9 g of 3-chloro-1H-pyrazol-4-amine and 1.4 g of pyridine in 20 ml of dichloromethane. After the addition was complete, stirring was continued overnight. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure. To the obtained residue was added 20 ml of 1N aqueous hydrochloric acid, and the mixture was extracted with 20 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.2 g of the desired product as a yellow oil. The obtained target product was a mixture of two geometric isomers, and the isomer ratio was 2: 1.
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.52 (brs, 1H), 8.26 (s, 1H), 4.37-4.31 (m, 1H) 4.07 (s, 3H ), 2.14 (s, 3H), 1.62 (d, J = 7.5 Hz, 3H)
Isomer ratio 1
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.52 (brs, 1H), 8.50 (s, 1H), 4.37-4.31 (m, 1H) 4.07 (s, 3H ), 2.17 (s, 3H), 1.58 (d, J = 7.5 Hz, 3H)
　参考例９
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造
　工程１：３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボニル　アジドの製造
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸５００ｍｇのトルエン１０ｍｌ溶液に、室温にてトルエチルアミン０．２６ｇ、及びジフェニルホスホリルアジド７１０ｍｇを順次添加した。添加終了後、該反応溶液を室温にて５．５時間攪拌した。攪拌終了後、該反応溶液にトリエチルアミン６２ｍｇ、及びジフェニルホスホリルアジド１７０ｍｇを順次再度添加した。添加終了後、該反応溶液を室温にて３．５時間攪拌を継続した。反応終了後、該反応溶液に酢酸エチル２０ｍｌを添加した。添加終了後、有機層を２８重量％アンモニア水２ｍｌ、水１０ｍｌ、飽和食塩水、次いで無水硫酸マグネシウムの順で洗浄・乾燥し、減圧下にて溶媒を留去した。得られた固体を、ｎ－ヘキサン：ジイソプロピルエーテル（２：１）の混合溶液５ｍｌで洗浄し、目的物４１９ｍｇを白色固体として得た。
融点；９９－１０３℃（分解）
　工程２：３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボニル　アジド１２０ｍｇのトルエン２．５ｍｌ溶液を、１００℃にて３０分間攪拌した。攪拌終了後、該反応溶液を室温まで冷却した後、濃塩酸１ｍｌを添加した。添加終了後、該反応溶液を室温にて１０分間攪拌を継続した。反応終了後、該反応溶液に１０重量％水酸化ナトリウム水溶液を添加し、該反応溶液のｐＨを１１とした後、酢酸エチル１０ｍｌで２回抽出した。得られた有機層を飽和食塩水、無水硫酸マグネシウムの順で洗浄・乾燥し、減圧下にて溶媒を留去し、目的物８５ｍｇを白色固体として得た。
融点；１３３－１３５℃ Reference Example 9
Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine Step 1: Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carbonyl azide To a solution of 500 mg of 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid in 10 ml of toluene, 0.26 g of toluethylamine and 710 mg of diphenylphosphoryl azide were sequentially added at room temperature. After completion of the addition, the reaction solution was stirred at room temperature for 5.5 hours. After completion of stirring, 62 mg of triethylamine and 170 mg of diphenylphosphoryl azide were sequentially added again to the reaction solution. After completion of the addition, the reaction solution was continuously stirred at room temperature for 3.5 hours. After completion of the reaction, 20 ml of ethyl acetate was added to the reaction solution. After completion of the addition, the organic layer was washed and dried in the order of 28% by weight of aqueous ammonia 2 ml, water 10 ml, saturated brine, and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 5 ml of a mixed solution of n-hexane: diisopropyl ether (2: 1) to obtain 419 mg of the desired product as a white solid.
Melting point: 99-103 ° C (decomposition)
Step 2: Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carbonyl azide 120 mg The toluene 2.5 ml solution was stirred at 100 ° C. for 30 minutes. After completion of the stirring, the reaction solution was cooled to room temperature, and 1 ml of concentrated hydrochloric acid was added. After completion of the addition, the reaction solution was continuously stirred at room temperature for 10 minutes. After completion of the reaction, 10% by weight aqueous sodium hydroxide solution was added to the reaction solution to adjust the pH of the reaction solution to 11, and then extracted twice with 10 ml of ethyl acetate. The obtained organic layer was washed and dried in the order of saturated brine and anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 85 mg of the desired product as a white solid.
Melting point: 133-135 ° C
　参考例１０
　（＋）－２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸の製造
　工程１：２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸（Ｆ－００２のオキシム構造に由来する幾何異性体）の製造
　２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸３５ｇのジクロロメタン１６０ｍｌ溶液に、オキサリルクロリド２８ｇ及びＮ，Ｎ－ジメチルホルムアミド０．５ｍｌを添加した。添加終了後、該反応溶液を室温下にて２時間攪拌した。反応終了後、該反応溶液の溶媒を減圧下にて留去した後、得られた残留物にテトラヒドロフラン４０ｍｌを添加し、溶解させた。得られた溶液を、別途調製した１．５Ｍ水酸化カリウム水溶液３００ｍｌに０℃にて添加した。添加終了後、該反応溶液を室温にて３時間撹拌した。攪拌終了後、該反応溶液をジエチルエーテル２００ｍｌで洗浄し、次いで濃塩酸でｐＨ１とした後、酢酸エチル３００ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下にて溶媒を留去し、目的物３３ｇを薄黄油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０５（ｓ，３Ｈ），４．０３（ｔ，Ｊ＝９．０Ｈｚ，１Ｈ），２．１０（ｓ，３Ｈ），２．１０－１．９０（ｍ，２Ｈ），０．９６（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
　工程２：（＋）－２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸の製造
　工程１で合成した２－（メトキシイミノ）－３－（メチルチオ）ペンタン酸９６ｇのアセトニトリル２８８ｍｌ溶液に、キニジン１５５ｇ及びジイソプロピルエーテル７６８ｍｌを順次添加した。添加終了後、該反応溶液を６５℃にて５分間攪拌した。攪拌終了後、該反応溶液を室温にて３時間撹拌を継続した。攪拌終了後、該反応溶液中に析出した固体をろ過し、得られた固体にアセトニトリル４０５ｍｌ及びジイソプロピルエーテル５７６ｍｌを加え、６５℃で５分間攪拌した後、室温下にて１５時間攪拌を継続した。析出した固体をろ過し、得られた固体に１Ｍ塩酸水溶液を３００ｍｌ加え、酢酸エチル３００ｍｌにて抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下にて溶媒を留去し、目的物２３ｇを薄黄油状物として得た。
　比旋光度；[α]D 22.0+35.2゜(CHCl3,c=0.461) Reference Example 10
Preparation of (+)-2- (methoxyimino) -3- (methylthio) pentanoic acid Step 1: Geometric isomer derived from 2- (methoxyimino) -3- (methylthio) pentanoic acid (F-002 oxime structure) ) 28 g of oxalyl chloride and 0.5 ml of N, N-dimethylformamide were added to a solution of 35 g of 2- (methoxyimino) -3- (methylthio) pentanoic acid in 160 ml of dichloromethane. After completion of the addition, the reaction solution was stirred at room temperature for 2 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure, and then 40 ml of tetrahydrofuran was added to the obtained residue to dissolve it. The obtained solution was added at 0 ° C. to 300 ml of a 1.5 M aqueous potassium hydroxide solution prepared separately. After completion of the addition, the reaction solution was stirred at room temperature for 3 hours. After completion of the stirring, the reaction solution was washed with 200 ml of diethyl ether, adjusted to pH 1 with concentrated hydrochloric acid, and extracted with 300 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 33 g of the objective product as a pale yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.05 (s, 3H), 4.03 (t, J = 9.0 Hz, 1H), 2.10 (s, 3H), 2.10 − 1.90 (m, 2H), 0.96 (t, J = 7.5 Hz, 3H) (The proton peak of CO 2 H was not observed.)
Step 2: Preparation of (+)-2- (methoxyimino) -3- (methylthio) pentanoic acid To a solution of 96 g of 2- (methoxyimino) -3- (methylthio) pentanoic acid synthesized in Step 1 in 288 ml of acetonitrile, quinidine 155 g and 768 ml of diisopropyl ether were added sequentially. After completion of the addition, the reaction solution was stirred at 65 ° C. for 5 minutes. After completion of the stirring, the reaction solution was continuously stirred at room temperature for 3 hours. After completion of the stirring, the solid precipitated in the reaction solution was filtered, and 405 ml of acetonitrile and 576 ml of diisopropyl ether were added to the obtained solid. After stirring at 65 ° C. for 5 minutes, stirring was continued at room temperature for 15 hours. The precipitated solid was filtered, 300 ml of 1M aqueous hydrochloric acid solution was added to the obtained solid, and the mixture was extracted with 300 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 23 g of the desired product as a pale yellow oil.
Specific rotation: [α] D 22.0 + 35.2 ° (CHCl 3 , c = 0.461)
　参考例１１
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造（その２）
　工程１：３－メチル－１Ｈ－ピラゾール－４－アミンの製造
　オーガニック　プロセス　リサーチ　アンド　ディベロップメント　２００９年，１３巻，６９８頁記載の方法に準じて合成した３－メチル－４－ニトロ－１Ｈ－ピラゾール１．０ｇのテトラヒドロフラン６ｍｌ溶液に、５重量％パラジウム－活性炭０．１ｇを添加した。添加終了後、反応容器中を水素ガスに置換した後、室温にて一晩撹拌した。反応終了後、該反応混合物からパラジウム－活性炭をセライト濾過により除去した。得られたろ液を減圧下にて溶媒を留去し、目的物０．７１ｇを茶色固体として得た。
融点；８８－８９℃
　工程２：３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造
　３－メチル－１Ｈ－ピラゾール－４－アミン０．６１ｇのジメチルスルホキシド１０ｍｌの溶液に、３－ブロモピリジン１ｇ、ヨウ化銅（１価）０．２４ｇ、炭酸セシウム３．１ｇ及びｔｒａｎｓ－Ｎ，Ｎ’－ジメチルシクロヘキサン－１，２－ジアミン０．３６ｇを順次添加した。添加終了後、反応容器内を窒素ガスで置換した後、１４０℃にて１４時間撹拌した。反応終了後、該反応混合物中に析出した固体をろ別した。得られたろ液に水５０ｍｌを添加し、クロロホルム１００ｍｌにて抽出した。得られた有機層を、７重量％アンモニア水溶液５０ｍｌ次いで飽和食塩水で洗浄した後、無水硫酸ナトリウムで脱水・乾燥した。減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１～０：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物及びその異性体である５－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの混合物２７６ｍｇを得た。この混合物をジイソプロピルエーテルで洗浄して、目的物１３４ｍｇを茶色固体として得た。
融点；１２５－１２７℃ Reference Example 11
Production of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine (Part 2)
Step 1: Production of 3-methyl-1H-pyrazol-4-amine 3-methyl-4-nitro-1H-pyrazole 1 synthesized according to the method described in Organic Process Research and Development 2009, Vol. 13, p. 698 0.1 g of 5 wt% palladium-activated carbon was added to 0.0 g of 6 ml tetrahydrofuran solution. After completion of the addition, the reaction vessel was replaced with hydrogen gas, and then stirred overnight at room temperature. After completion of the reaction, palladium-activated carbon was removed from the reaction mixture by Celite filtration. The solvent was distilled off from the obtained filtrate under reduced pressure to obtain 0.71 g of the desired product as a brown solid.
Melting point: 88-89 ° C
Step 2: Preparation of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine 3-methyl-1H-pyrazol-4-amine 0.61 g of dimethyl sulfoxide in 10 ml of solution 1 g of bromopyridine, 0.24 g of copper iodide (monovalent), 3.1 g of cesium carbonate, and 0.36 g of trans-N, N′-dimethylcyclohexane-1,2-diamine were sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas and then stirred at 140 ° C. for 14 hours. After completion of the reaction, the solid precipitated in the reaction mixture was filtered off. 50 ml of water was added to the obtained filtrate and extracted with 100 ml of chloroform. The obtained organic layer was washed with 50 ml of a 7 wt% aqueous ammonia solution and then with saturated saline, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 3: 1 to 0: 1) to obtain the desired product and its isomer 5- 276 mg of a mixture of methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine was obtained. This mixture was washed with diisopropyl ether to obtain the desired product (134 mg) as a brown solid.
Melting point: 125-127 ° C
　参考例１２
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造（その３）
　３－メチル－１Ｈ－ピラゾール－４－アミン０．６１ｇのジメチルスルホキシド３ｍｌの溶液に、３－ブロモピリジン１ｇ、ヨウ化銅（１価）０．２４ｇ、炭酸セシウム３．３ｇ及び２－ヒドロキシベンズアルデヒド　オキシム０．３５ｇを順次添加した。添加終了後、反応容器内を窒素ガスで置換した後、１４０℃にて２時間撹拌した。反応終了後、該反応混合物中に析出した固体をろ別した。得られたろ液に水２０ｍｌを添加し、クロロホルム３０ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した。減圧下にて溶媒を留去した。得られた残留物を、酢酸エチルにて溶出するシリカゲルクロマトグラフィーにて精製し、目的物２３６ｍｇを薄黄色固体として得た。
融点；１３１－１３５℃ Reference Example 12
Production of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine (Part 3)
To a solution of 0.61 g of 3-methyl-1H-pyrazol-4-amine in 3 ml of dimethyl sulfoxide, 1 g of 3-bromopyridine, 0.24 g of copper iodide (monovalent), 3.3 g of cesium carbonate and 2-hydroxybenzaldehyde oxime 0.35 g was added sequentially. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 140 ° C. for 2 hours. After completion of the reaction, the solid precipitated in the reaction mixture was filtered off. 20 ml of water was added to the obtained filtrate and extracted with 30 ml of chloroform. The obtained organic layer was washed with water and then dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with ethyl acetate to obtain 236 mg of the desired product as a pale yellow solid.
Melting point: 131-135 ° C
　参考例１３
　３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－アミンの製造（その４）
　３－メチル－１Ｈ－ピラゾール－４－アミン０．９３ｇのジメチルスルホキシド５ｍｌの溶液に、３－ブロモピリジン０．５ｇ、ヨウ化銅（１価）０．１２ｇ及び炭酸セシウム１．６ｇを順次添加した。添加終了後、反応容器内を窒素ガスで置換した後、１４０℃にて７時間撹拌した。反応終了後、該反応混合物中に析出した固体をろ別した。得られたろ液に水５０ｍｌを添加し、クロロホルム１００ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した。減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（３：１～０：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１１４ｍｇを黄色固体として得た。
融点；１３１－１３３℃ Reference Example 13
Production of 3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-amine (Part 4)
To a solution of 0.93 g of 3-methyl-1H-pyrazol-4-amine in 5 ml of dimethyl sulfoxide, 0.5 g of 3-bromopyridine, 0.12 g of copper iodide (monovalent) and 1.6 g of cesium carbonate were sequentially added. . After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 140 ° C. for 7 hours. After completion of the reaction, the solid precipitated in the reaction mixture was filtered off. 50 ml of water was added to the obtained filtrate and extracted with 100 ml of chloroform. The obtained organic layer was washed with water and then dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 3: 1 to 0: 1) to obtain 114 mg of the desired product as a yellow solid.
Melting point: 131-133 ° C
　参考例１４
　合成例１の工程５と同様の方法を用いて、以下の中間体を合成した。
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－３－（エチルチオ）－２－オキソブタンアミド
融点；１０８－１１０℃
　３－（エチルチオ）－Ｎ－｛３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－２－オキソブタンアミド
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．８８（ｄ，Ｊ＝２．７Ｈｚ，１Ｈ），８．５９（ｄｄ，Ｊ＝４．５，１．５Ｈｚ，１Ｈ），８．０７（ｓ，１Ｈ），８．００－７．９５（ｍ，１Ｈ），７．４２（ｄｄ，Ｊ＝８．１，４．５Ｈｚ，１Ｈ），４．１０（ｑ，Ｊ＝６．９Ｈｚ，１Ｈ），３．３４（ｓ，３Ｈ），１．５６（ｓ，３Ｈ），１．３０（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－メチル－３－（メチルチオ）－２－オキソブタンアミド
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ８．９８（ｄ，Ｊ＝２．４Ｈｚ，１Ｈ），８．８３（ｂｒｓ，１Ｈ），８．７２（ｓ，１Ｈ），８．６０－８．５５（ｍ，１Ｈ），８．０５－７．９５（ｍ，１Ｈ），７．４５－７．３５（ｍ，１Ｈ），４．４３（ｑ，Ｊ＝６．９Ｈｚ，１Ｈ），２．６５－２．４０（ｍ，２Ｈ），１．５２（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ），１．２４（ｔ，Ｊ＝７．５Ｈｚ，３Ｈ）
　Ｎ－｛３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－３－（メチルチオ）－２－オキソブタンアミド
融点；１０２－１０４℃
　Ｎ－｛３－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－３－（メチルチオ）－２－オキソペンタンアミド
融点；９４－９６℃
　Ｎ－｛４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル｝－３－（メチルチオ）－２－オキソブタンアミド
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ９．１７（ｂｒｓ，１Ｈ），９．１３（ｄ，Ｊ＝２．４Ｈｚ，１Ｈ），８．７０－８．５５（ｍ，１Ｈ），８．２５－８．１０（ｍ，１Ｈ），７．３６（ｄｄ，Ｊ＝８．４，４．８Ｈｚ，１Ｈ），４．５０（ｑ，Ｊ＝７．２Ｈｚ，１Ｈ），２．５２（ｓ，３Ｈ），１．９７（ｓ，３Ｈ），１．５０（ｄ，Ｊ＝７．２Ｈｚ，３Ｈ）
　Ｎ－｛４－クロロ－２－（ピリジン－３－イル）チアゾール－５－イル｝－３－（メチルチオ）－２－オキソブタンアミド
融点；１１７－１２１℃ Reference Example 14
The following intermediates were synthesized using the same method as in Step 5 of Synthesis Example 1.
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3- (ethylthio) -2-oxobutanamide melting point; 108-110 ° C.
3- (Ethylthio) -N- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -2-oxobutanamide
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.88 (d, J = 2.7 Hz, 1H), 8.59 (dd, J = 4.5, 1.5 Hz, 1H), 8.07 (S, 1H), 8.00-7.95 (m, 1H), 7.42 (dd, J = 8.1, 4.5 Hz, 1H), 4.10 (q, J = 6.9 Hz, 1H), 3.34 (s, 3H), 1.56 (s, 3H), 1.30 (d, J = 6.9 Hz, 3H)
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N-methyl-3- (methylthio) -2-oxobutanamide
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 8.98 (d, J = 2.4 Hz, 1H), 8.83 (brs, 1H), 8.72 (s, 1H), 8.60− 8.55 (m, 1H), 8.05-7.95 (m, 1H), 7.45-7.35 (m, 1H), 4.43 (q, J = 6.9 Hz, 1H), 2.65-2.40 (m, 2H), 1.52 (d, J = 7.2 Hz, 3H), 1.24 (t, J = 7.5 Hz, 3H)
N- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3- (methylthio) -2-oxobutanamide melting point; 102-104 ° C.
N- {3-methyl-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -3- (methylthio) -2-oxopentanamide melting point; 94-96 ° C.
N- {4-Methyl-2- (pyridin-3-yl) thiazol-5-yl} -3- (methylthio) -2-oxobutanamide
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 9.17 (brs, 1H), 9.13 (d, J = 2.4 Hz, 1H), 8.70-8.55 (m, 1H), 8.25-8.10 (m, 1H), 7.36 (dd, J = 8.4, 4.8 Hz, 1H), 4.50 (q, J = 7.2 Hz, 1H), 2.52 (S, 3H), 1.97 (s, 3H), 1.50 (d, J = 7.2 Hz, 3H)
N- {4-chloro-2- (pyridin-3-yl) thiazol-5-yl} -3- (methylthio) -2-oxobutanamide melting point; 117-121 ° C.
　参考例１５
　２－（メトキシイミノ）－３－メチル－４－（メチルチオ）ブタン酸の製造
　ジャーナル　オブ　ザ　ケミカル　ソサエティー　パーキン　トランスアクションズ　１　１９９５年，１４８３頁記載の方法に準じて合成した２－（メトキシイミノ）－３－メチル－３－ブテン酸１．１ｇの３０重量％水酸化カリウム水溶液２０ｍｌの溶液に、ジチオ炭酸　Ｓ，Ｓ‘－ジメチル１．９ｇを添加し９０℃にて一晩撹拌した。反応終了後、該反応溶液を１Ｎ塩酸水溶液にてｐＨ１とし、酢酸エチル２０ｍｌ（×３）にて抽出した。得られた有機層を、飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した。減圧下にて溶媒を留去し、目的物０．８ｇを茶色油状物として得た。得られた目的物は２種の幾何異性体混合物であり、異性体比は３：２であった。
異性体比３
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０８（ｓ，３Ｈ），３．１７－３．０７（ｍ，１Ｈ），２．８４（ｄｄ，Ｊ＝１３．５，７．５Ｈｚ，１Ｈ），２．５９（ｄｄ，Ｊ＝１３．５，７．５Ｈｚ，１Ｈ），２．１１（ｓ，３Ｈ），１．２８（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。）
異性体比２
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．０６（ｓ，３Ｈ），３．６４－３．５６（ｍ，１Ｈ），３．０１（ｄｄ，Ｊ＝１３．５，９．３Ｈｚ，１Ｈ），２．７０（ｄｄ，Ｊ＝１３．５，６．６Ｈｚ，１Ｈ），２．０８（ｓ，３Ｈ），１．２８（ｄ，Ｊ＝６．９Ｈｚ，３Ｈ）（ＣＯ２Ｈのプロトンピークは観測されなかった。） Reference Example 15
Preparation of 2- (methoxyimino) -3-methyl-4- (methylthio) butanoic acid 2- (methoxyimino) -3 synthesized according to the method described in Journal of the Chemical Society Parkin Transactions 1 1995, page 1483 -To a solution of 1.1 g of methyl-3-butenoic acid in 20 ml of 30 wt% potassium hydroxide aqueous solution, 1.9 g of S, S′-dimethyl dithiocarbonate was added and stirred overnight at 90 ° C. After completion of the reaction, the reaction solution was adjusted to pH 1 with 1N aqueous hydrochloric acid and extracted with 20 ml (x3) of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated saline and anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.8 g of the objective product as a brown oil. The obtained target product was a mixture of two kinds of geometric isomers, and the isomer ratio was 3: 2.
Isomer ratio 3
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.08 (s, 3H), 3.17-3.07 (m, 1H), 2.84 (dd, J = 13.5, 7.5 Hz) , 1H), 2.59 (dd, J = 13.5, 7.5 Hz, 1H), 2.11 (s, 3H), 1.28 (d, J = 6.9 Hz, 3H) (CO 2 H No proton peak was observed.)
Isomer ratio 2
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.06 (s, 3H), 3.64-3.56 (m, 1H), 3.01 (dd, J = 13.5, 9.3 Hz) , 1H), 2.70 (dd, J = 13.5, 6.6 Hz, 1H), 2.08 (s, 3H), 1.28 (d, J = 6.9 Hz, 3H) (CO 2 H No proton peak was observed.)
　参考例１６
　３－（１，３－ジチアン－２－イル）－２－（メトキシイミノ）プロパン酸の製造
　工程１：エチル　３－（１，３－ジチアン－２－イル）－２－オキソプロパノエートの製造
　シンセシス　１９８８年　２７４頁記載の方法に準じて合成したエチル　４－エトキシ－２－オキソブト－３－エノエート３．２ｇのトルエン１８ｍｌ溶液に、１，３－プロパンジチオール１．８ｍｌ、及びｐ－トルエンスルホン酸一水和物０．１７ｇを順次添加した後、４０℃にて１０時間撹拌した。反応終了後、該反応溶液にトルエン２５ｍｌを添加した後、飽和炭酸水素ナトリウム水溶液で洗浄した。得られた有機層を飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した後、減圧下にて溶媒を留去し、目的物４ｇを黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．５１（ｔ，Ｊ＝７．２Ｈｚ，１Ｈ），４．３５（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），３．３５（ｄ，Ｊ＝７．２Ｈｚ，２Ｈ），２．９４－２．８６（ｍ，４Ｈ），２．２０－２．０５（ｍ，１Ｈ），２．０５－１．８５（ｍ，１Ｈ），１．３９（ｔ，Ｊ＝７．２Ｈ，３Ｈ） Reference Example 16
Preparation of 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoic acid Step 1: Preparation of ethyl 3- (1,3-dithian-2-yl) -2-oxopropanoate Synthesis 1988, synthesized in accordance with the method described on page 274, ethyl 4-ethoxy-2-oxobut-3-enoate in a solution of 3.2 g of toluene, 1.8 ml of 1,3-propanedithiol, and p-toluenesulfonic acid After sequentially adding 0.17 g of monohydrate, the mixture was stirred at 40 ° C. for 10 hours. After completion of the reaction, 25 ml of toluene was added to the reaction solution, followed by washing with a saturated aqueous sodium hydrogen carbonate solution. The obtained organic layer was dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4 g of the desired product as a yellow oil.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.51 (t, J = 7.2 Hz, 1H), 4.35 (q, J = 7.2 Hz, 2H), 3.35 (d, J = 7.2 Hz, 2H), 2.94-2.86 (m, 4H), 2.20-2.05 (m, 1H), 2.05-1.85 (m, 1H), 1.39 (T, J = 7.2H, 3H)
　工程２：エチル　３－（１，３－ジチアン－２－イル）－２－（メトキシイミノ）プロパノエートの製造
　エチル　３－（１，３－ジチアン－２－イル）－２－オキソプロパノエート２ｇのエタノール２０ｍｌ溶液にＯ－メチルヒドロキシルアミン　塩酸塩０．８６ｇを添加し室温にて２時間撹拌した。反応終了後、該反応溶液から減圧下にて溶媒を留去し、残留物に水３０ｍｌを添加した後、酢酸エチル５０ｍｌにて抽出した。得られた有機層を飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した後、減圧下にて溶媒を留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（２０：１～４：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物２．１ｇを薄黄色油状物として得た。
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．３５（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．３０（ｔ，Ｊ＝８．１Ｈｚ，１Ｈ），４．０９（ｓ，３Ｈ），３．２１（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ），２．９５（ｄｄｄ，Ｊ＝１４．４，７．２，３．０Ｈｚ，２Ｈ），２．７７（ｄｄｄ，Ｊ＝１４．４，９．６，３．０Ｈｚ，２Ｈ），２．１５－１．８５（ｍ，２Ｈ），１．３７（ｔ，Ｊ＝７．２Ｈ，３Ｈ）
　工程３：３－（１，３－ジチアン－２－イル）－２－（メトキシイミノ）プロパン酸の製造
　エチル　３－（１，３－ジチアン－２－イル）－２－（メトキシイミノ）プロパノエート２ｇのエタノール２０ｍｌ溶液に、水２５ｍｌ及び水酸化ナトリウム０．３６ｇを添加し、室温にて２時間撹拌した。反応終了後、該反応溶液から減圧下にてエタノールを留去した。残留した水層に濃塩酸を加えてｐＨ２とした後、酢酸エチル３０ｍｌ（ｘ２）で抽出した。得られた有機層を飽和食塩水、無水硫酸ナトリウムの順で脱水・乾燥した後、減圧下にて溶媒を留去して、目的物１．４ｇを白色固体として得た。
融点；１２９－１３１℃ Step 2: Preparation of ethyl 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoate Ethyl 3- (1,3-dithian-2-yl) -2-oxopropanoate To a 20 ml solution of ethanol, 0.86 g of O-methylhydroxylamine hydrochloride was added and stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, and 30 ml of water was added to the residue, followed by extraction with 50 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 20: 1 to 4: 1) to give 2.1 g of the desired product as a pale yellow oil. Got as.
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.35 (q, J = 7.2 Hz, 2H), 4.30 (t, J = 8.1 Hz, 1H), 4.09 (s, 3H ), 3.21 (d, J = 8.1 Hz, 2H), 2.95 (ddd, J = 14.4, 7.2, 3.0 Hz, 2H), 2.77 (ddd, J = 14. 4, 9.6, 3.0 Hz, 2H), 2.15 to 1.85 (m, 2H), 1.37 (t, J = 7.2H, 3H)
Step 3: Preparation of 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoic acid 2 g of ethyl 3- (1,3-dithian-2-yl) -2- (methoxyimino) propanoate 25 ml of water and 0.36 g of sodium hydroxide were added to a 20 ml ethanol solution and stirred at room temperature for 2 hours. After completion of the reaction, ethanol was distilled off from the reaction solution under reduced pressure. Concentrated hydrochloric acid was added to the remaining aqueous layer to adjust the pH to 2, followed by extraction with 30 ml (x2) of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 1.4 g of the objective product as a white solid.
Melting point: 129-131 ° C
　参考例１７
　参考例１６と同様の方法を用いて、以下の中間体を合成した。
　エチル　３－（１，３－ジチオラン－２－イル）－２－（メトキシイミノ）プロパノエート
１Ｈ　ＮＭＲ（ＣＤＣｌ３，Ｍｅ４Ｓｉ，３００ＭＨｚ）δ４．９１（ｔ，Ｊ＝７．８Ｈｚ，１Ｈ），４．３５（ｑ，Ｊ＝７．２Ｈｚ，２Ｈ），４．０８（ｓ，３Ｈ），３．３６－３．１８（ｍ，４Ｈ），３．１０（ｄ，Ｊ＝７．８Ｈｚ，２Ｈ），１．３７（ｔ，Ｊ＝７．２Ｈ，３Ｈ）
　３－（１，３－ジチオラン－２－イル）－２－（メトキシイミノ）プロパン酸
融点；７８－８０℃ Reference Example 17
The following intermediates were synthesized using the same method as in Reference Example 16.
Ethyl 3- (1,3-dithiolan-2-yl) -2- (methoxyimino) propanoate
1 H NMR (CDCl 3 , Me 4 Si, 300 MHz) δ 4.91 (t, J = 7.8 Hz, 1H), 4.35 (q, J = 7.2 Hz, 2H), 4.08 (s, 3H ), 3.36-3.18 (m, 4H), 3.10 (d, J = 7.8 Hz, 2H), 1.37 (t, J = 7.2H, 3H)
3- (1,3-dithiolan-2-yl) -2- (methoxyimino) propanoic acid melting point; 78-80 ° C.
　本発明化合物は、前記製造法及び実施例に準じて製造することができる。合成例１～２２と同様に製造した本発明化合物の例を第５表～第１１表に示し、それらの物性値を第１２表に示すが、本発明はこれらのみに限定されるものではない。
　なお、表中、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピル基を、ｃ－Ｐｅｎ及びＰｅｎ－ｃはシクロペンチル基を、ｃ－Ｈｅｘ及びＨｅｘ－ｃはシクロへキシル基を表し、表し、Ｄ１－２ａ、Ｄ１－７ｂ、Ｄ１－３２ａ、Ｄ１－３２ｂ、Ｄ１－３３ａ、Ｄ１－３３ｂ、Ｄ１－３４ａ、Ｄ１－３７ａ、Ｄ１－８４ａ、Ｄ１－８７ａ、Ｄ１－９８ａ、Ｄ１－１０３ｋ、Ｄ１－１０３ｍ、Ｄ１－１０３ｎ、Ｄ１－１０３ｏ、Ｄ１－１０３ｐ、Ｄ１－１０３ｑ、Ｄ１－１０８ａ及びＤ１－１０８ｂで表される構造は下記の構造を表し、Ｄ１－７ｂ、Ｄ１－３２ｂ及びＤ１－３３ｂの構造式に記された番号は、Ｘ１の置換位置を表し、Ｄ１－１０８ｂの構造式に記された番号は、Ｚの置換位置を表す。
　また表中、「＊１」は「樹脂状」を表す。また「＊２」は樹脂状で、同一構造であるが２種類の異性体混合物の場合を表す。異性体比が判明した場合は、第１２表にその比を記載する。「＊３」はオキシム構造又はヒドラゾン構造に由来する幾何異性体を表す。「＊４」は樹脂状で、同一構造であるが３種類の異性体混合物の場合を表す。異性体比が判明した場合は、第１２表にその比を記載する。ｄｅｃｏｍｐ．は分解を表す。
　また、第１２表の記号は下記の意味を表す。
ｓ：シングレット、ｄ：ダブレット、ｔ：トリプレット、ｑ：カルテット、ｑｕｉ：クインテット、ｓｘｔ：シックステット、ｓｅｐ：セプテット、ｍ：マルチプレット、ｂｒｓ：ブロードピーク。 This invention compound can be manufactured according to the said manufacturing method and an Example. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 22 are shown in Tables 5 to 11 and their physical properties are shown in Table 12. However, the present invention is not limited to these. .
In the table, c-Pr and Pr-c represent cyclopropyl groups, c-Pen and Pen-c represent cyclopentyl groups, c-Hex and Hex-c represent cyclohexyl groups, and D1-2a D1-7b, D1-32a, D1-32b, D1-33a, D1-33b, D1-34a, D1-37a, D1-84a, D1-87a, D1-98a, D1-103k, D1-103m, D1 The structures represented by −103n, D1−103o, D1−103p, D1−103q, D1−108a, and D1−108b represent the following structures, and are described in the structural formulas of D1-7b, D1−32b, and D1−33b. the number that is, represents the substitution position of X 1, numbers written in the structural formula of D1-108b represents the substitution position of Z.
In the table, “* 1” represents “resin”. Further, “* 2” represents a resin-like structure having the same structure but a mixture of two isomers. If the isomer ratio is known, the ratio is listed in Table 12. “* 3” represents a geometric isomer derived from an oxime structure or a hydrazone structure. “* 4” represents a resinous structure having the same structure but a mixture of three isomers. If the isomer ratio is known, the ratio is listed in Table 12. decomp. Represents decomposition.
The symbols in Table 12 have the following meanings.
s: singlet, d: doublet, t: triplet, q: quartet, qui: quintet, sxt: sickted, sep: septette, m: multiplet, brs: broad peak.
Figure JPOXMLDOC01-appb-C000200
Figure JPOXMLDOC01-appb-C000200
〔第５表〕
Figure JPOXMLDOC01-appb-C000201
 [Table 5]
Figure JPOXMLDOC01-appb-C000201
――――――――――――――――――――――――――――――――――
No.     R3    Y      Ra             Rb-1                   m.p.(℃)
――――――――――――――――――――――――――――――――――
1-001   Cl    O    CH2CH3         C(=NOCH2SCH3)CH3          92-95
1-002   Cl    O    H2CH3    C(=NOCH3)CH(CH3)S(O)2CH3    *2(～92:8)
1-003   Cl    O    CH2CH3        C(=NOH)CH3               144-146
1-004   Cl    O    CH2CH3        CH(=NOH)                 152-155
1-005   Cl    O    CH2CH3       C(=NOH)CH2CH3             111-113
1-006   Cl    O    CH2CH3        C(=NOCH2SCH3)CH2CH3        45-50
1-007   Cl    O    CH2CH3      C(=NOCH2CH2OCH3)CH2CH3    *2(～5:2)
1-008   Cl    O    CH2CH3      C{=NOCH2CH(OCH3)2}CH2CH3  *2(～4:1)
1-009   Cl    O    CH2CH3         C(=NOCH3)(D1-34a)          *1
1-010   Cl    O    CH2C≡CH       C(=NOCH3)CH2SCH3      *2(～7:1)
1-011   Cl    O    CH2C≡CH       C(=NOCH3)CH2S(O)CH3        *1
1-012   Cl    O    CH2C≡CH       C(=NOCH3)CH2S(O)2CH3       *1
1-013   Cl    O    CH2CH3         C{=NOCH2S(O)2CH3}CH3      72-75
1-014   Cl    O    CH2CH3         C(=NOCH2CH2OCH3)CH3       60-63
1-014(*3)                                                      *1
1-015   Cl    O    H            C(=NOCH3)CH(CH3)S(O)CH3   115-119
1-016   Cl    O    CH2CH3       C{=NOCH2CH(OCH3)2}CH3    *2(～3:2)
1-017   Cl    O    CH2CH3       C(=NOCH2CN)CH3           *2(～3:2)
1-018   Cl    O    CH2CH3         C(=NOCH3)(D1-32a)       114-116
1-018(*3)                                                131-133
1-019   Cl    O    H            C(=NOCH3)CH(CH3)S(O)2CH3  111-113
1-020   Cl    O    CH2CH3         C{=NOCH2S(O)CH3}CH3     130-132
1-020(*3)                                                    *1
1-021   Cl    O    H              C(=NOCH3)CH2S(O)CH3     154-156
1-022   Cl    O   CH2CH3         C{=NOC(O)CH3}CH3           58-60
1-023   Cl    O   CH2CH3    C{=NOC(O)CH(CH3)SCH2CH3}CH3  *2(～3:2)
1-024   Cl    O   CH2CH3    C{=NOC(O)CH2CH2SCH3}CH3    *2(～27:25)
1-025   Cl    O    CH2CH3      C{=NOCH2C(O)NHCH2CF3}CH3     42-46
1-026   Cl    O    CH3        C(=NOCH2CH2OCH3)CH2S(O)CH3    72-73
1-027   Cl    O    CH3           C(=NOCH3)CH2S(O)CH3        90-94
1-028   Cl    O    CH3         C(=NOCH3)CH2S(O)2CH3       149-152
1-029   Cl    O    CH3        C(=NOCH3)CH(CH3)SCH3    *2(～85:15)
1-030   Cl    O    CH3        C(=NOCH3)CH(CH3)S(O)CH3 *4(～5:4:1)
1-031   Cl    O    CH3        C(=NOCH3)CH(CH3)S(O)2CH3  *2(～9:1)
1-032   Cl    O    H             C(=NOCH3)CH2SCH3        108-112
1-033   Cl    O    CH2C≡CH     C(=NOCH3)(D1-103k)     *2(～5:1)
1-034   Cl    O    CH3            C(=NOCH2CH3)CH2SCH3        *1
1-035   Cl    O    CH2CH3       C(=NOCH2CH2SCH3)CH3         40-45
1-036   Cl    O    CH2CH3       C{=NOCH2C(O)OCH2CH3}CH3     52-57
1-037   Cl    O    CH3         C(=NOCH2CH3)CH2S(O)CH3   *2(～4:1)
1-038   Cl    O    CH3           C(=NOCH2CH3)CH2S(O)2CH3    87-91
1-039   Cl    O    CH3         C(=NOCH2Pr-c)CH2S(O)CH3    128-130
1-040   Cl    O    CH3         C(=NOCH2Pr-c)CH2S(O)2CH3   155-157
1-041   Cl    O    CH2CH3        C(=NOCH3)CH(CH3)SCH3       72-74
1-042   Cl    O   CH2CH3       C(=NOCH3)CH(CH3)S(O)CH3  *2(～3:2)
1-043   Cl    O    CH2OCH3        C(=NOCH3)CH2SCH3             *1
1-044   Cl    O   CH2OCH3      C(=NOCH3)CH2S(O)2CH3   *2(～85:15)
1-045   Cl    O    CH2OCH2CH3     C(=NOCH3)CH2SCH3           *1
1-046   Cl    O    CH2CN        C(=NOCH3)CH2SCH3       *2(～92:8)
1-047   Cl    O    CH3            C(=NOCH2Pr-c)CH2SCH3       *1
1-048   Cl    O    CH3            C(=NOCH2CH2OCH3)CH2SCH3     *1
1-049   Cl    O    CH3        C(=NOCH2CH2OCH3)CH2S(O)2CH3  106-107
1-050   Cl    O    CH3            C(=NOCH2SCH3)CH2SCH3        *1
1-051   Cl    O    CH3            C(=NOCH2CH2SCH3)CH2SCH3     *1
1-052   Cl    O    CH3            C(=NOCH2OCH3)CH2SCH3       85-89
1-053   Cl    O    CH3            C(=NOCH2OCH3)CH2S(O)CH3     *1
1-054   Cl    O    CH3            C(=NOCH3)C(O)CH3        *2(～3:2)
1-055   Cl    O    CH3          C(=NOCH2OCH3)CH2S(O)2CH3 *2(～50:7)
1-056   Cl    O    CH2CN          C(=NOCH3)CH(CH3)SCH3        *1
1-056(*3)                                               *2(～81:19)
1-056-(+)        97.1 %e.e.       [α]D 23.6+34.88゜(CHCl3,c=0.734)
1-056-(-)        99 %e.e.         [α]D 23.5-41.23゜(CHCl3,c=0.624)
1-057   Cl    O    H              C(=NOCH3)CH(CH3)SCH3       80-82
1-057(*3)                                                      *1
1-057-(+)        90.2 %e.e.       [α]D 23.3+36.92゜(CHCl3,c=0.104)
1-057-(-)        99 %e.e.         [α]D 23.2-42.84゜(CHCl3,c=0.116)
1-058   Cl    O    CH2SCH3        C(=NOCH3)CH2SCH3             *1
1-059   Cl    O    CH2CH=CH2      C(=NOCH3)CH2SCH3             *1
1-060   Cl    O    CH3            C(=NOPr-i)CN                *1
1-061   Cl    O    H              C(=NOCH2CH2OCH3)CH2SCH3     75-78
1-062   Cl    O    H              C(=NOCH3)CH2S(O)2CH3       169-171
1-063   Cl    O    CH2CN          C(=NOCH3)CH2S(O)2CH3       122-124
1-064   Cl    O    CH2C≡CH       C(=NOCH3)C{S(O)2CH3}=CH2   133-134
1-065   Cl    O    CH2Pr-c        C(=NOCH3)CH2SCH3              *1
1-066   Cl    O    CH(CH3)OCH3     C(=NOCH3)CH2SCH3      *2(～87:13)
1-067   Cl    O    CH2(D1-108a)    C(=NOCH3)CH2SCH3             *1
1-068   Cl    O    C(O)OCH3        C(=NOCH3)CH2SCH3        *2(～5:1)
1-069   Cl    O   CH2(D1-108b,2-Cl)  C(=NOCH3)CH2SCH3           *1
1-070   Cl    O   CH2(D1-108b,3-Cl)  C(=NOCH3)CH2SCH3           *1
1-071   Cl    O   CH2(D1-108b,4-Cl)  C(=NOCH3)CH2SCH3           *1
1-072   Cl    O    CH2C(O)OCH3     C(=NOCH3)CH2SCH3            83-86
1-073   Cl    O    CH2OC(O)CH3     C(=NOCH3)CH2SCH3               *1
1-074   Cl    O    CH(CH3)CN       C(=NOCH3)CH2SCH3        *2(～5:1)
1-075   Cl    O    CH(CH3)OCH3     C(=NOCH3)CH2S(O)CH3     *2(～1:1)
1-076   Cl    O    CH(CH3)OCH3     C(=NOCH3)CH2S(O)2CH3      125-127
1-077   Cl    O    CH2OCH3         C(=NOCH3)CH(CH3)SCH3         *1
1-077(*3)                                                *2(～5:1)
1-078   Cl    O    CH3             C(=NOCH3)SCH2CH3         135-138
1-079   Cl    O    CH(CH3)CN       C(=NOCH3)CH(CH3)SCH3         *1
1-080   Cl    O    CH3             C(=NOCH3)CH2CH2SCH3     *2(～1:1)
1-081   Cl    O  CH2OCH2(D1-108a)   C(=NOCH3)CH(CH3)SCH3        *1
1-082   Cl    O    CH2CN          C(=NOCH3)CH(CH3)S(O)CH3  *2(～3:2)
1-083   Cl    O    CH2CN          C(=NOCH3)CH(CH3)S(O)2CH3   144-147
1-084   Cl    O    CH2OC(O)CH3     C(=NOCH3)CH2S(O)2CH3         *1
1-085   Cl   O  CH(CH3)OC(O)OCH2CH3  C(=NOCH3)CH(CH3)SCH3  *2(～4:1)
1-086   Cl    O  CH2OC(O)C(CH3)3    C(=NOCH3)CH(CH3)SCH3        *1
1-087   Cl    O    CH2OC(O)CH3     C(=NOCH3)CH(CH3)SCH3         *1
1-088   Cl   O   CH2OC(O)CH3    C(=NOCH3)CH(CH3)S(O)2CH3 *2(～20:13)
1-089   Cl    O    CH2OCH2CH2OCH3  C(=NOCH3)CH(CH3)SCH3         *1
1-090   Cl    O    CH2OCH3       C(=NOCH3)CH(CH3)S(O)CH3   *2(～4:1)
1-090(*3)                                                 *2(～6:1)
1-091   Cl    O    CH2OCH3         C(=NOCH3)CH(CH3)S(O)2CH3     *1
1-091(*3)                                                    37-40
1-092   Cl  O  CH2OCH2(D1-108a)  C(=NOCH3)CH(CH3)S(O)2CH3  *2(～4:3)
1-093   Cl    O   CH2OCH2(D1-108a)   C(=NOCH3)CH(CH3)S(O)CH3    *1
1-094   Cl    O  CH2OCH2CH2Si(CH3)3 C(=NOCH3)CH(CH3)SCH3        *1
1-095   Cl    O   CH2OC(O)(D1-108a)   C(=NOCH3)CH(CH3)SCH3      *1
1-096   Cl    O   CH2OC(O)CH2CH2CH3   C(=NOCH3)CH(CH3)SCH3      *1
1-097   Cl    O    CH2OCH2CH3      C(=NOCH3)CH(CH3)SCH3       47-49
1-098   Cl    O    CH2OCH2CH3      C(=NOCH3)CH(CH3)S(O)2CH3     *1
1-099   Cl    O    S(O)2CH3         C(=NOCH3)CH(CH3)SCH3        *1
1-100   Cl    O    CH2C(O)NH2     C(=NOCH3)CH(CH3)SCH3          *1
1-101   Cl    O    CH2C(O)OCH2CH3  C(=NOCH3)CH(CH3)SCH3        66-68
1-102   Cl    O    C(O)OCH3        C(=NOCH3)CH(CH3)SCH3           *1
1-103   Cl    O    H               C(=NOCH3)CH(CH3)SCH2CH3     64-67
1-104   Cl    O    CH2CN         C(=NOCH3)CH(CH3)SCH2CH3   *2(～95:5)
1-105   Cl    O    CH2OC(O)OCH3     C(=NOCH3)CH(CH3)SCH3       58-61
1-105(*3)                                                 *2(～2:1)
1-106   Cl    O    CH2OCH(CH3)2    C(=NOCH3)CH(CH3)SCH3        55-57
1-107   Cl    O    CH2OCH2C≡CH     C(=NOCH3)CH(CH3)SCH3       79-81
1-108   Cl    O  CH2C(O)N(CH2CH3)2   C(=NOCH3)CH(CH3)SCH3      80-82
1-109   Cl    O    CH2C(O)OH       C(=NOCH3)CH(CH3)SCH3      209-213
1-110   Cl    O  CH2C(O)NHCH2CH3     C(=NOCH3)CH(CH3)SCH3    142-144
1-111   Cl    O    C(O)NHCH2CH3     C(=NOCH3)CH(CH3)SCH3       46-49
1-112   Cl   O   CH2OC(O)N(CH2CH3)2 C(=NOCH3)CH(CH3)SCH3   *2(～50:6)
1-113   Cl    O   CH(CH3)OCH3     C(=NOCH3)CH(CH3)SCH3   *2(～83:10)
1-114   Cl    O    CH2SCH3          C(=NOCH3)CH(CH3)SCH3        *1
1-115   Cl    O    CH(CH3)OCH2CH3  C(=NOCH3)CH(CH3)SCH3  *2(～83:17)
1-116   CH3   O    H                C(=NOCH3)CH(CH3)SCH3       72-75
1-116(*3)                                                      *1
1-116-(+)        94.5%e.e.       [α]D 24.7 +37.0°(CHCl3,c=0.443)
1-116-(-)        99%e.e.         [α]D 22.8 -45.60°(CHCl3,c=0.120)
1-117   Cl    O  CH2OC(O)OCH2CH3     C(=NOCH3)CH(CH3)SCH3      51-64
1-118   Cl    O  CH2OC(O)OCH2CH2OCH3   C(=NOCH3)CH(CH3)SCH3     *1
1-119   Cl    O  CH2OC(O)OCH2CH2OCH3   C(=NOCH3)CH(CH3)S(O)2CH3  *1
1-120   Cl    O    C(S)NHCH3     C(=NOCH3)CH(CH3)SCH3    *2(～87:13)
1-121   Cl    O    H               C(=NOCH3)CH(CH2CH3)SCH3     62-63
1-122   Cl    O    H           C(=NOCH3)CH{CH(CH3)2}SCH3  *2(～93:7)
1-123   H     O    H              C(=NOCH3)CH(CH3)SCH3       110-120
1-124   Cl    O   CH2OC(O)OCH3     C(=NOCH3)CH(CH3)SCH2CH3     46-49
1-125   CH3   O   CH2OC(O)OCH3    C(=NOCH3)CH(CH3)SCH3         86-88
1-126   Cl    O   CH2OC(O)OCH3   C(=NOCH3)CH(CH3)S(O)2CH2CH3   83-86
1-127   Cl    O    CH2OC(O)OCH3     C(=NOCH3)CH(CH2CH3)SCH3    69-70
1-128   H     O    CH2OC(O)OCH3     C(=NOCH3)CH(CH3)SCH3        *1
1-129   H     O    CH2OC(O)OCH3     C(=NOCH3)CH(CH3)S(O)2CH3    *1
1-130   Cl    O    CH2OC(O)OCH3    C(=NOCH3)CH(CH3)S(O)2CH3  113-116
1-131   Cl    O    H              C(=NOCH2CH3)CH(CH3)SCH3      64-67
1-132   Cl   O  CH2OC(O)OCH3    C(=NOCH3)CH{CH(CH3)2}SCH3  *2(～3:1)
1-133   CH3   O   CH2OC(O)OCH3    C(=NOCH3)CH(CH3)S(O)2CH3   125-127
1-134   Cl    O   CH2OC(O)OCH3    C(=NOCH2CH3)CH(CH3)SCH3      52-54
1-135   CH3   O    H              C(=NOCH3)CH(CH3)SCH2CH3      69-71
1-136   CH3   O    H             C(=NOCH3)CH(CH3)S(O)CH3     118-127
1-137   CH3   O    H             C(=NOCH3)CH(CH3)S(O)2CH3    124-129
1-138   CH3   O    H              C(=NOCH3)CH(CH3)S(O)CH2CH3  88-110
1-139   CH3   O    H           C(=NOCH3)CH(CH3)S(O)2CH2CH3   138-143
1-140   Cl    O    H              C(=NOCH2CH3)CH(CH3)SCH2CH3   55-60
1-141   CH3   O    H              C(=NOCH3)CH(CH2CH3)SCH3      80-84
1-141-(+)      85%e.e.    [α]D 23.0 +12.03°(CHCl3,c=0.142)    93-94
1-141-(-)      99%e.e.    [α]D 22.9 -46.11°(CHCl3,c=0.110)    96-97
1-142   CH3   O    CH2OC(O)CH3      C(=NOCH3)CH(CH3)SCH2CH3     *1
1-143   CH3   O    CH2OC(O)OCH3      C(=NOCH3)CH(CH3)SCH2CH3    *1
1-144   CH3   O    CH2OCH3        C(=NOCH3)CH(CH3)SCH3     *2(～5:1)
1-145   CH3  O C(O)C(=NOCH3)CH(CH3)SCH3  C(=NOCH3)CH(CH3)SCH2CH3  *1
1-146   Cl    O    H            C(=NOCH3)(D1-2a)            114-116
1-147   CH3   O    CH3           C(=NOCH3)CH(CH2CH3)SCH3       62-64
1-148   CH3   O    CH3         C(=NOCH3)CH(CH2CH3)S(O)CH3  *2(～2:1)
1-149   CH3   O    CH3      C(=NOCH3)CH(CH2CH3)S(O)2CH3   *2(～25:3)
1-150   Cl    O    CH3            C(=NOCH3)CH(CH2CH3)SCH3      65-67
1-151   CH3   O    CH3            C(=NOCH3)CH(CH3)SCH3         50-52
1-152   Cl    O    CH2(D1-33a)      C(=NOCH3)CH(CH3)SCH2CH3  110-113
1-153   Cl    O    CH2(D1-34a)       C(=NOCH3)CH(CH3)SCH2CH3     *1
1-154   CH3   O    H           C(=NOCH3)CH(CH2CH3)S(O)CH3  *2(～8:7)
1-155   CH3   O    H                C(=NOCH3)CH(CH2CH3)S(O)2CH3  *1
1-156   CH3   O    H                C(=NOCH3)CH(CH2OCH3)SCH3     *1
1-157   Cl    O  CH2(D1-32a)       C(=NOCH3)CH(CH3)SCH2CH3     80-82
1-158   CH3   O    CH3              C(=NOCH3)CH(CH3)S(O)CH3    34-35
1-159   CH3   O    CH3              C(=NOCH3)CH(CH3)S(O)2CH3   42-43
1-160   CH3   O    CH2OC(O)CH3      C(=NOCH3)CH(CH2CH3)SCH3       *1
1-161   CH3   O    CH2OC(O)OCH3    C(=NOCH3)CH(CH2CH3)SCH3     64-65
1-162   CH3   O    H                C(=NOCH3)CH(CH2OCH3)S(O)2CH3  *1
1-163   CH3   O    CH2OCH2CH3        C(=NOCH3)CH(CH3)SCH3         *1
1-164   CH3   O    CH2OC(O)OCH3     C(=NOCH3)CH(CH2OCH3)SCH3      *1
1-165   CH3   O    CH2OC(O)OCH3     C(=NOCH3)CH(CH2OCH3)S(O)CH3   *1
1-166   CH3   O    CH2OC(O)OCH3     C(=NOCH3)CH(CH2OCH3)S(O)2CH3  *1
1-167   CH3   O  CH2OC(O)OCH3  C(=NOCH3)CH(CH2CH3)S(O)CH3  *2(～3:2)
1-168   CH3   O    CH2OC(O)OCH3     C(=NOCH3)CH(CH2CH3)S(O)2CH3   *1
1-169   CH3   O    CH2OC(O)CH3   C(=NOCH3)CH(CH2CH3)S(O)CH3  126-127
1-170   CH3   O    CH2OC(O)CH3      C(=NOCH3)CH(CH2CH3)S(O)2CH3   *1
1-171   CH3   O    CH2CN            C(=NOCH3)CH(CH2CH3)SCH3      *1
1-172   CH3   O    CH2OCH2CH3        C(=NOCH3)CH(CH3)S(O)CH3     *1
1-173   CH3  O  CH2OCH2CH3   C(=NOCH3)CH(CH3)S(O)2CH3 *4(～58:27:15)
1-174   CH3   O    CH2CN            C(=NOCH3)CH(CH3)SCH3         *1
1-175   CH3   O    CH2CN        C(=NOCH3)CH(CH3)S(O)CH3    *2(～5:3)
1-176   CH3   O    CH2CN            C(=NOCH3)CH(CH3)S(O)2CH3     *1
1-177   CH3   O    CH2CN            C(=NOCH3)CH(CH2CH3)S(O)CH3   *1
1-178   CH3   O    CH2CN            C(=NOCH3)CH(CH2CH3)S(O)2CH3  *1
1-179   CH3   O    CH2OC(O)CH3   C(=NOCH3)CH(CH3)SCH3     *2(～10:1)
1-180   CH3   O    CH2OC(O)CH3      C(=NOCH3)CH(CH3)S(O)CH3      *1
1-181   CH3   O    CH2OC(O)CH3      C(=NOCH3)CH(CH3)S(O)2CH3     *1
1-182   CH3   O    CH2OC(O)OCH3     C(=NOCH3)CH(CH3)S(O)CH3      *1
1-183   CH3   O    CH2CN            C(=NOCH2CH3)CH(CH3)SCH3       *1
1-184   CH3   O    CH2CN            C(=NOCH2CH2OCH3)CH2SCH3       *1
1-185   CH3   O    CH2OCH2CH3        C(=NOCH3)CH(CH2CH3)SCH3      *1
1-186   Cl    O    CH3            C(=NOH)CH(CH3)SCH3        163-165
1-187   CH3   O    CH2OCH2CH3      C(=NOCH3)CH(CH2CH3)S(O)CH3     *1
1-188   CH3   O   CH2OCH2CH3     C(=NOCH3)CH(CH2CH3)S(O)2CH3  99-100
1-189   CH3   O    CH2OCH3          C(=NOCH3)CH(CH2CH3)S(O)CH3    *1
1-190   CH3  O   CH2OCH3      C(=NOCH3)CH(CH2CH3)S(O)2CH3  *2(～2:1)
1-191   CH3  O   CH2OCH3    C(=NOCH3)CH(CH3)S(O)2CH3  *4(～51:25:24)
1-192   CH3   O    CH2OCH3         C(=NOCH3)CH(CH2CH3)SCH3        *1
1-193   Cl    O    H             C(=NOCH3)CH2{D1-7b(3-CF3)}  133-136
1-194   Cl    O    CH3              C(=NOCH2CN)CH(CH3)SCH3       *1
1-195   Cl    O    CH3              C{=NOC(O)OCH3}CH(CH3)SCH3    *1
1-196   Cl    O    CH3              C{=NOC(O)CH3}CH(CH3)SCH3     *1
1-197   CH3   O    H                C(=NOCH3)C(CH3)2SCH3         *1
1-198   Cl    O    CH3              C(=NOCH2OCH3)CH(CH3)SCH3     *1
1-199   Br    O    H               C(=NOCH3)CH(CH3)SCH3       85-88
1-200   CH3   O    H               C(=NOCH3)C(CH3)2S(O)2CH3       *1
1-201   CH3   O    H               C(=NOCH3)CH2SCH3           97-102
1-202   CH3   O    H              C(=NOCH3)CH2S(O)2CH3       167-170
1-203   CH3   O   H  C(=NOCH3)CH(CH2CH3)OS(O)2{D1-108b(Z=4-CH3)}  *1
1-204   CH3   O    H               C(=NOCH3)CH(CH2CH3)Cl     105-107
1-205   CH3   O    H         C(=NOCH3)CH(CH2CH3)S{D1-32b(3-CF3)}  *1
1-206   CH3   S    H                C(=NOCH3)CH(CH3)SCH3       73-76
1-207   CH3   O    H               C(=NOCH3)(D1-108a)      *2(～2:1)
1-208   Cl    O    C(O)CH(CH3)SCH3   C(=NOCH3)CH3                *1
1-209   CH3   O    H              C(=NOCH3)CH(CH2CH3)SCH2CF3   70-72
1-210   Cl    O    CH2CH3          C{=NNHS(O)2CH3}CH3          41-44
1-211   CH3   O    H           C{=NNHC(O)CH3}CH(CH2CH3)SCH3  138-142
1-212   CH3   O    H              C(=NNHCH2CH3)CH(CH2CH3)SCH3     *1
1-213   CH3   O    H         C{=NNHC(O)OCH3}CH(CH2CH3)SCH3   144-146
1-214   CH3   O    H              C{=NNH(D1-37a)}CH(CH3)SCH3   49-51
1-215   Cl    O    CH3              C{=NNH(D1-37a)}CH3         39-41
1-216   CH3   O    H         C{=NNH(D1-37a)}CH(CH3)S(O)2CH3  191-194
1-217   CH3   O    H           C(=NNHCH2CF3)CH(CH2CH3)SCH3   133-135
1-217(*3)                                                    61-64
1-218   CH3   O    H            C{=NNH(D1-108a)}CH(CH2CH3)SCH3    *1
1-219   CH3   O    H              C(=NNH2)CH(CH2CH3)SCH3     127-130
1-220   CH3   O    H                C{=NNHC(O)H}CH(CH3)SCH3    41-44
1-221   Cl    O    H          C{=NNHC(O)OC(CH3)3}CH(CH3)SCH3   49-50
1-222   Cl    O    H              C{=NNHCH2CH=CH2}CH(CH3)SCH3     *1
1-223   CH3   O    H                C(=NOCH3)CH(CH2CH3)OCH3    90-92
1-224   Cl    O    H             C(=NOCH3){D1-108b(4-Cl)}    214-215
1-225   CH3   O    H       C(=NOCH3)CH(CH2CH3)SCH2CH=CH2   *2(～3:1)
1-226   CH3   O    H                C(=NOH)CH(CH3)SCH3       207-210
1-227   Cl    O    H       CH[=NNHC(O)NH{D1-108b(2,6-Cl2)}]  211-214
1-228   CH3   O    H             C{=NNHC(O)CH3}CH(CH3)SCH3   154-156
1-228(*3)                                                   116-118
1-229   Cl    O    H             C{=NNHC(O)CH3}CH(CH3)SCH3   154-156
1-230   CH3   O    C(O)Pr-c      C[=NNHC(O)Pr-c]CH(CH3)SCH3    59-61
1-231   CH3   O    H       C{=NNHC(O)OCH2(D1-108a)}CH(CH3)SCH3    *1
1-231(*3)                                                   103-105
1-232   Cl    O   H   C(=NOCH2CH2CH2CH2CH2CH3)CH(CH3)SCH3   *2(～7:3)
1-233   Cl    O    H           C(=NOCH2Pr-c)CH(CH3)SCH3    *2(～2:1)
1-234   CH3   O    H            C(=NOCH3)C(O)OCH2CH3         120-122
1-235   CH3   O    H             C(=NOCH2CH3)CN              120-122
1-236   CH3   O    H         C{=NNHC(O)CH2OCH3}CH(CH3)SCH3     64-66
1-237   CH3   O    H           C{=NNHC(O)NHCH2CH3}CH(CH3)SCH3     *1
1-238   Cl    O    H               C{=NNH(c-Hex)}CH(CH3)SCH3     *1
1-239   CH3   O    H           C{=NN=C(CH3)2}CH(CH3)SCH3     139-140
1-240   Cl    O    H      C(=NOCH3)CH(CH2CH=CH2)S(O)2CH3   *2(～7:3)
1-241   Cl    O    H   C[=NOCH2{D1-108b(4-OCH3)}]CH(CH3)SCH3   95-96
1-242   Cl    O    H           C(=NOCH2C≡CH)CH(CH3)SCH3   *2(～2:1)
1-243   Cl    O    H            C(=NOH)CH(CH3)SCH3           198-199
1-244   CH3   O    H             C(=NNH2)CH(CH3)SCH3           88-90
1-245   CH3   O    H            C(=NOCH3)CH(CH2CH3)S(Hex-c)       *1
1-246   CH3   O    H          C{=NNHC(O)(D1-32a)}CH(CH3)SCH3   60-70
1-247   CH3   O    H      C{=NNHC(O)(D1-108a)}CH(CH3)SCH3  *2(～6:1)
1-248   CH3   O    H           C{=N(D1-103m)}CH(CH3)SCH3   *2(～5:2)
1-249   CH3   O    H        C{=NNHC(O)CH2CN}CH(CH3)SCH3   *2(～10:9)
1-250   CH3   O    H            C{=NNH(D1-32a)}CH(CH3)SCH3       *1
1-251   CH3   O    H     C[=NNH{D1-108b(4-OCF3)]CH(CH3)SCH3  120-125
1-252   CH3   O    H            C(=NOCH3)C(O)NHCH3           162-168
1-253   CH3   O    H               C(=NOCH3)C(O)CH2CH3           *1
1-254   CH3   O    H     C(=NOCH3)C{=NNHC(O)CH3}CH2CH3  220(decomp.)
1-255   CH3   O    H            C(=NOCH3)C(=NOCH3)CH2CH3         *1
1-256   CH3   O    H                C(=NOCH2CN)CH(CH3)SCH3       *1
1-257   CH3   O    H          C(=NOCH2CH2OCH3)CH(CH3)SCH3  *2(～7:3)
1-258   CH3   O    H        C{=NNHC(O)CH2Pr-c}CH(CH3)SCH3  *2(～5:2)
1-259   CH3   O    H          C{=NNHC(O)CH2CH3}CH(CH3)SCH3   142-144
1-260   CH3   O    H             C{=NN=CH(OCH3)}CH(CH3)SCH3    50-54
1-261   CH3   O    H       C{=NNHC(O)CH2SCH3}CH(CH3)SCH3   *2(～3:1)
1-262   CH3   O   H           C{=NNHC(O)CH3}CH(CH3)S(O)CH3   121-123
1-263   CH3   O   H           C{=NNHC(O)CH=CH2}CH(CH3)SCH3     50-52
1-264   Cl   O   H             C(=NOCH2CH=CH2)CH(CH3)SCH3  *2(～3:2)
1-265   Cl   O   H           C{=NOCH2C(O)OCH3}CH(CH3)SCH3  *2(～7:3)
1-266   Cl   O   H          C{=NOCH2CH(CH3)OH}CH(CH3)SCH3  *2(～3:2)
1-267   Cl   O   H      C{=NOCH2C(O)(D1-103n)}CH(CH3)SCH3  *2(～4:1)
1-268  Cl   O   H  C{=NOCH2CH2CH2CH2CH2CH2CH3}CH(CH3)SCH3   *2(～1:1)
1-269   Cl    O    H            C{=NOCH2C(O)OH}CH(CH3)SCH3   145-160
1-270   CH3   O    H            C(=NOCH2CH3)CH(CH3)SCH3    *2(～1:1)
1-271   CH3   O    H           C(=NOCH2CH2CH3)CH(CH3)SCH3  *2(～3:2)
1-272   CH3   O    H             C(=NOCH2Pr-c)CH(CH3)SCH3  *2(～3:2)
1-273   CH3   O    H    C(=NOCH3)CH(CH2CH3)S{D1-108b(4-OCH3)}    *1
1-274   CH3   O    H             C(=NOCH2SCH3)CH(CH3)SCH3  *2(～3:1)
1-275   CH3   O    H    C{=NNHC(S)NH(D1-108a)}CH(CH3)SCH3  *2(～6:5)
1-276   CH3   O    H       C{=NNHC(O)NHCH2CH=CH2}CH(CH3)SCH3     *1
1-277   CH3  O   H   C[=NNHC(O)NH{D1-108b(2-CF3)}]CH(CH3)SCH3  60-70
1-278   CH3   O    H             C(=NNH2)CH(CH3)S(O)2CH3     205-210
1-279   CH3   O    H         C{=NNHC(O)CH3}CH(CH3)S(O)2CH3   182-185
1-280   CH3  O   H        C{=NNHC(O)NHPen-c}CH(CH3)SCH3    *2(～2:1)
1-281   CH3   O   H         C{=NNHC(O)C≡CCH3}CH(CH3)SCH3    170-172
1-282   CH3   O    H     C{=NNHC(O)CH2(D1-103o)} CH(CH3)SCH3      *1
1-283   CH3   O   H    C{=NNHC(O)CH2C(O)OCH2CH3}CH(CH3)SCH3   98-100
1-284   CH3   O    H                 C{=NNHC(O)CH3}CH3       235-245
1-285   CH3   O    H             C(=NOCH3)CH(CH2C≡CH)S(O)2CH3    *1
1-286   C(O)CH3  O  H                  C(=NOCH3)CH(CH2CH3)SCH3    *1
1-287   CH3   O    C(O)CH3            C(=NOCH3)CH(CH2CH3)SCH3     *1
1-288   CH3   O   H               C(=NOCH2OCH3)CH(CH3)SCH3   179-180
1-289   Cl    O    H            C(=NOCH2CF3)CH(CH3)SCH3    *2(～3:2)
1-290   CH3  O  H  C[=NNHC(O){D1-108b(4-SCF3)}]CH(CH3)SCH3 *2(～4:1)
1-291   CH3   O   H       C{=NNHC(O)NH(D1-108a)}CH(CH3)SCH3    65-70
1-292   CH3   O    H                  C(=NNHCH2CH3)CH(CH3)SCH3   *1
1-293   CH3   O    H                C{=NNHC(O)OCH3}CH(CH3)SCH3   *1
1-294   H     O    H              C{=NNHC(O)OCH3}CH(CH3)SCH3   50-52
1-295   CH3   O    H        C{=NNHS(O)2(D1-108a)}CH(CH3)SCH3 148-150
1-296   CH3   O    H          C{=NNHC(O)OCH2CH=CH2}CH(CH3)SCH3   *1
1-297   CH3   O    H            C{=NNHC(O)C(O)CH3}CH(CH3)SCH3    *1
1-298   CH3   O    H       C{=NNHC(O)(D1-103p)}CH(CH3)SCH3 *2(～4:1)
1-298(*3)                                                   160-175
1-299   CH3   O  CH2CH2OSi(CH3)2C(CH3)3  C(=NOCH3)CH(CH2CH3)SCH3   *1
1-300   CH3   O  CH2CH2OH            C(=NOCH3)CH(CH2CH3)SCH3   87-88
1-301   Cl    O    H        C(=NOCH3)CH(CH3){D1-108b(4-Cl)}  101-103
1-302   CH3   O    H                   C(=NOCH2SCH3)CH3      119-121
1-303   CH3   O    H                 C(=NOCH2CH2SCH3)CH3       82-84
1-304   CH3   O    H        C{=NNHC(O)CH(=NOCH3)}CH(CH3)SCH3   80-83
1-304(*3)                                                   104-108
1-305   CH3   O    H                 C(=NOCH3)CH(CH3)CH2SCH3   84-86
1-306   CF3   O    H                 C(=NOCH3)CH(CH2CH3)SCH3      *1
1-307  C≡CSi(CH3)3  O   CH2CH3      C(=NOCH3)CH(CH2CH3)SCH3      *1
1-308  C≡CH  O    CH2CH3           C(=NOCH3)CH(CH2CH3)SCH3   99-100
1-309   CH3   O    H              C{=NNHS(O)2CH3}CH(CH3)SCH3      *1
1-309(*3)                                                   105-110
1-310   CH3   O    H        C{=NNHC(O)SCH(CH3)2}CH(CH3)SCH3    45-48
1-311   CH3   O    CH3           C{=NNHC(O)OCH3}CH(CH3)SCH3  120-130
1-312   CH3   O   CH2CH2OCH3        C{=NNHC(O)OCH3}CH(CH3)SCH3    *1
1-313   CH3   O  H    C{=NN(CH3)C(O)OC(CH3)3}CH(CH3)SCH3   *2(～5:3)
1-314   CH3   O    H     C{=NOCH2C(O)OCH2CH3}CH(CH3)SCH3          *1
1-315   CH3   O    H    C{=NOCH2C(=NOCH3)CH3}CH(CH3)SCH3   *2(～7:3)
1-316   CH3   O    H    C{=NOCH2(D1-84a)}CH(CH3)SCH3       *2(～4:1)
1-317   CH3   O   H     C[=NOCH2{D1-33b(6-Cl)}]CH(CH3)SCH3   146-147
1-318   CH3  O   H   C[=NOCH2{D1-108b(4-CN)}]CH(CH3)SCH3   *2(～7:3)
1-319   CH3  O  H  C[=NOCH2{D1-108b(4-SCH3)}]CH(CH3)SCH 3  *2(～7:3)
1-320   CH3  O  H  C「=NNHC(O)[D1-108b{2-(D1-103q)}]」CH(CH3)SCH3 *1
1-321   CH3   O    H               C(=NOCH3)CH2(D1-98a)           *1
1-322   CH3   O   CH3              C(=NOCH3)CH2(D1-98a)           *1
1-323   CH3   O    H         C(=NOCH3)CH(CH3)CH2S(O)CH3    *2(～1:1)
1-324   CH3   O    H           C(=NOCH3)CH(CH3)CH2S(O)2CH3        *1
1-325   CH3   O   CH3          C(=NOCH3)CH(CH3)CH2SCH3     *2(～3:1)
1-326   Cl    O    H          C(=NOCH3)CH(CH3)CH2SCH3            *1
1-327   CH3   O     H           C(=NOCH3)CH(D1-108a)CN           *1
1-328   CH3   O     H            C(=NOCH3)C(=CH2)CH3             *1
1-329   CH3   O     H           C(=NOCH3)CH(OH)CH2CH3        149-150
1-330   CH3   O     H   C{=NN(CH2CH3)C(O)CH3}CH(CH3)SCH3         *1
1-331   CH3   O     H           C(=NOCH3)CH(CH3)SCH2C≡CH        *1
1-332   CH3   O     H              C(=NOCH3)CH2(D1-87a)      129-130
1-333   CH3   O    CH3            C(=NOCH3)CH2(D1-87a)     *2(～4:1)
1-334   CH3   O    CH2OCH3            C(=NOCH3)CH2(D1-98a)       *1
1-335   Cl    O     H       C{=NOCH2CH(CH3)CH2ONH2}CH(CH3)SCH3   *1
1-336   CH3   O    CH3        C(=NOCH3)CH(CH2CH3)SCH2CH=CH2      *1
1-337   Cl    O     H      C{=NOCH2C(O)CH3}CH(CH3)SCH3           *1
1-338   CH3   O     H   C(=NOCH3)CH(CH2CH3)S(O)CH2CH=CH2   *2(～1:1)
1-339   CH3   O     H      C{=NNHC(O)CH2CH2CH3}CH(CH3)SCH3     93-95
1-340   CH3   O     H      C{=NNHC(O)CH(CH3)2}CH(CH3)SCH3      36-39
1-341   CH3   O     H      C{=NN=C(CH3)OCH3}CH(CH3)SCH3      117-120
1-342   CH3   O     H      C(=NOCH3)CH(CH2CH3)S(O)2CH2CH=CH2     *1
1-343   CH3   O     H      C(=NOCH3)CH(CH2CH3)CH2SCH3            *1
1-344   CH3   O     H      C(=NOCH3)CH(CH3)CH(CH3)SCH3           *1
―――――――――――――――――――――――――――――――――― ――――――――――――――――――――――――――――――――――
No. R 3 Y R a R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
1-001 Cl O CH 2 CH 3 C (= NOCH 2 SCH 3 ) CH 3 92-95
1-002 Cl O H 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 2 (～ 92: 8)
1-003 Cl O CH 2 CH 3 C (= NOH) CH 3 144-146
1-004 Cl O CH 2 CH 3 CH (= NOH) 152-155
1-005 Cl O CH 2 CH 3 C (= NOH) CH 2 CH 3 111-113
1-006 Cl O CH 2 CH 3 C (= NOCH 2 SCH 3 ) CH 2 CH 3 45-50
1-007 Cl O CH 2 CH 3 C (= NOCH 2 CH 2 OCH 3 ) CH 2 CH 3 * 2 (~ 5: 2)
1-008 Cl O CH 2 CH 3 C {= NOCH 2 CH (OCH 3 ) 2 } CH 2 CH 3 * 2 (～ 4: 1)
1-009 Cl O CH 2 CH 3 C (= NOCH 3 ) (D1-34a) * 1
1-010 Cl O CH 2 C≡CH C (= NOCH 3 ) CH 2 SCH 3 * 2 (～ 7: 1)
1-011 Cl O CH 2 C≡CH C (= NOCH 3 ) CH 2 S (O) CH 3 * 1
1-012 Cl O CH 2 C≡CH C (= NOCH 3 ) CH 2 S (O) 2 CH 3 * 1
1-013 Cl O CH 2 CH 3 C {= NOCH 2 S (O) 2 CH 3 } CH 3 72-75
1-014 Cl O CH 2 CH 3 C (= NOCH 2 CH 2 OCH 3 ) CH 3 60-63
1-014 (* 3) * 1
1-015 Cl O H C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 115-119
1-016 Cl O CH 2 CH 3 C {= NOCH 2 CH (OCH 3 ) 2 } CH 3 * 2 (～ 3: 2)
1-017 Cl O CH 2 CH 3 C (= NOCH 2 CN) CH 3 * 2 (～ 3: 2)
1-018 Cl O CH 2 CH 3 C (= NOCH 3 ) (D1-32a) 114-116
1-018 (* 3) 131-133
1-019 Cl O H C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 111-113
1-020 Cl O CH 2 CH 3 C {= NOCH 2 S (O) CH 3 } CH 3 130-132
1-020 (* 3) * 1
1-021 Cl O H C (= NOCH 3 ) CH 2 S (O) CH 3 154-156
1-022 Cl O CH 2 CH 3 C {= NOC (O) CH 3 } CH 3 58-60
1-023 Cl O CH 2 CH 3 C {= NOC (O) CH (CH 3 ) SCH 2 CH 3 } CH 3 * 2 (~ 3: 2)
1-024 Cl O CH 2 CH 3 C {= NOC (O) CH 2 CH 2 SCH 3 } CH 3 * 2 (~ 27: 25)
1-025 Cl O CH 2 CH 3 C {= NOCH 2 C (O) NHCH 2 CF 3 } CH 3 42-46
1-026 Cl O CH 3 C (= NOCH 2 CH 2 OCH 3 ) CH 2 S (O) CH 3 72-73
1-027 Cl O CH 3 C (= NOCH 3 ) CH 2 S (O) CH 3 90-94
1-028 Cl O CH 3 C (= NOCH 3 ) CH 2 S (O) 2 CH 3 149-152
1-029 Cl O CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 85: 15)
1-030 Cl O CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 4 (～ 5: 4: 1)
1-031 Cl O CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 2 (～ 9: 1)
1-032 Cl O H C (= NOCH 3 ) CH 2 SCH 3 108-112
1-033 Cl O CH 2 C≡CH C (= NOCH 3 ) (D1-103k) * 2 (～ 5: 1)
1-034 Cl O CH 3 C (= NOCH 2 CH 3 ) CH 2 SCH 3 * 1
1-035 Cl O CH 2 CH 3 C (= NOCH 2 CH 2 SCH 3 ) CH 3 40-45
1-036 Cl O CH 2 CH 3 C {= NOCH 2 C (O) OCH 2 CH 3 } CH 3 52-57
1-037 Cl O CH 3 C (= NOCH 2 CH 3 ) CH 2 S (O) CH 3 * 2 (～ 4: 1)
1-038 Cl O CH 3 C (= NOCH 2 CH 3 ) CH 2 S (O) 2 CH 3 87-91
1-039 Cl O CH 3 C (= NOCH 2 Pr-c) CH 2 S (O) CH 3 128-130
1-040 Cl O CH 3 C (= NOCH 2 Pr-c) CH 2 S (O) 2 CH 3 155-157
1-041 Cl O CH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 72-74
1-042 Cl O CH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 2 (～ 3: 2)
1-043 Cl O CH 2 OCH 3 C (= NOCH 3 ) CH 2 SCH 3 * 1
1-044 Cl O CH 2 OCH 3 C (= NOCH 3 ) CH 2 S (O) 2 CH 3 * 2 (-85: 15)
1-045 Cl O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH 2 SCH 3 * 1
1-046 Cl O CH 2 CN C (= NOCH 3 ) CH 2 SCH 3 * 2 (～ 92: 8)
1-047 Cl O CH 3 C (= NOCH 2 Pr-c) CH 2 SCH 3 * 1
1-048 Cl O CH 3 C (= NOCH 2 CH 2 OCH 3 ) CH 2 SCH 3 * 1
1-049 Cl O CH 3 C (= NOCH 2 CH 2 OCH 3 ) CH 2 S (O) 2 CH 3 106-107
1-050 Cl O CH 3 C (= NOCH 2 SCH 3 ) CH 2 SCH 3 * 1
1-051 Cl O CH 3 C (= NOCH 2 CH 2 SCH 3 ) CH 2 SCH 3 * 1
1-052 Cl O CH 3 C (= NOCH 2 OCH 3 ) CH 2 SCH 3 85-89
1-053 Cl O CH 3 C (= NOCH 2 OCH 3 ) CH 2 S (O) CH 3 * 1
1-054 Cl O CH 3 C (= NOCH 3 ) C (O) CH 3 * 2 (～ 3: 2)
1-055 Cl O CH 3 C (= NOCH 2 OCH 3 ) CH 2 S (O) 2 CH 3 * 2 (～ 50: 7)
1-056 Cl O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-056 (* 3) * 2 (～ 81: 19)
1-056-(+) 97.1% ee [α] D 23.6 + 34.88 ° (CHCl 3 , c = 0.734)
1-056-(-) 99% ee [α] D 23.5 -41.23 ° (CHCl 3 , c = 0.624)
1-057 Cl O H C (= NOCH 3 ) CH (CH 3 ) SCH 3 80-82
1-057 (* 3) * 1
1-057-(+) 90.2% ee [α] D 23.3 + 36.92 ° (CHCl 3 , c = 0.104)
1-057-(-) 99% ee [α] D 23.2 -42.84 ° (CHCl 3 , c = 0.116)
1-058 Cl O CH 2 SCH 3 C (= NOCH 3 ) CH 2 SCH 3 * 1
1-059 Cl O CH 2 CH = CH 2 C (= NOCH 3 ) CH 2 SCH 3 * 1
1-060 Cl O CH 3 C (= NOPr-i) CN * 1
1-061 Cl O H C (= NOCH 2 CH 2 OCH 3 ) CH 2 SCH 3 75-78
1-062 Cl O H C (= NOCH 3 ) CH 2 S (O) 2 CH 3 169-171
1-063 Cl O CH 2 CN C (= NOCH 3 ) CH 2 S (O) 2 CH 3 122-124
1-064 Cl O CH 2 C≡CH C (= NOCH 3 ) C {S (O) 2 CH 3 } = CH 2 133-134
1-065 Cl O CH 2 Pr-c C (= NOCH 3 ) CH 2 SCH 3 * 1
1-066 Cl O CH (CH 3 ) OCH 3 C (= NOCH 3 ) CH 2 SCH 3 * 2 (～ 87: 13)
1-067 Cl O CH 2 (D1-108a) C (= NOCH 3 ) CH 2 SCH 3 * 1
1-068 Cl O C (O) OCH 3 C (= NOCH 3 ) CH 2 SCH 3 * 2 (～ 5: 1)
1-069 Cl O CH 2 (D1-108b, 2-Cl) C (= NOCH 3 ) CH 2 SCH 3 * 1
1-070 Cl O CH 2 (D1-108b, 3-Cl) C (= NOCH 3 ) CH 2 SCH 3 * 1
1-071 Cl O CH 2 (D1-108b, 4-Cl) C (= NOCH 3 ) CH 2 SCH 3 * 1
1-072 Cl O CH 2 C (O) OCH 3 C (= NOCH 3 ) CH 2 SCH 3 83-86
1-073 Cl O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH 2 SCH 3 * 1
1-074 Cl O CH (CH 3 ) CN C (= NOCH 3 ) CH 2 SCH 3 * 2 (～ 5: 1)
1-075 Cl O CH (CH 3 ) OCH 3 C (= NOCH 3 ) CH 2 S (O) CH 3 * 2 (～ 1: 1)
1-076 Cl O CH (CH 3 ) OCH 3 C (= NOCH 3 ) CH 2 S (O) 2 CH 3 125-127
1-077 Cl O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-077 (* 3) * 2 (～ 5: 1)
1-078 Cl O CH 3 C (= NOCH 3 ) SCH 2 CH 3 135-138
1-079 Cl O CH (CH 3 ) CN C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-080 Cl O CH 3 C (= NOCH 3 ) CH 2 CH 2 SCH 3 * 2 (～ 1: 1)
1-081 Cl O CH 2 OCH 2 (D1-108a) C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-082 Cl O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 2 (～ 3: 2)
1-083 Cl O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 144-147
1-084 Cl O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH 2 S (O) 2 CH 3 * 1
1-085 Cl O CH (CH 3 ) OC (O) OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 4: 1)
1-086 Cl O CH 2 OC (O) C (CH 3 ) 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-087 Cl O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-088 Cl O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 2 (~ 20: 13)
1-089 Cl O CH 2 OCH 2 CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-090 Cl O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 2 (～ 4: 1)
1-090 (* 3) * 2 (～ 6: 1)
1-091 Cl O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-091 (* 3) 37-40
1-092 Cl O CH 2 OCH 2 (D1-108a) C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 2 (~ 4: 3)
1-093 Cl O CH 2 OCH 2 (D1-108a) C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 1
1-094 Cl O CH 2 OCH 2 CH 2 Si (CH 3 ) 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-095 Cl O CH 2 OC (O) (D1-108a) C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-096 Cl O CH 2 OC (O) CH 2 CH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-097 Cl O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 47-49
1-098 Cl O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-099 Cl O S (O) 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-100 Cl O CH 2 C (O) NH 2 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-101 Cl O CH 2 C (O) OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 66-68
1-102 Cl O C (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-103 Cl O H C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 64-67
1-104 Cl O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 * 2 (～ 95: 5)
1-105 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 58-61
1-105 (* 3) * 2 (～ 2: 1)
1-106 Cl O CH 2 OCH (CH 3 ) 2 C (= NOCH 3 ) CH (CH 3 ) SCH 3 55-57
1-107 Cl O CH 2 OCH 2 C≡CH C (= NOCH 3 ) CH (CH 3 ) SCH 3 79-81
1-108 Cl O CH 2 C (O) N (CH 2 CH 3 ) 2 C (= NOCH 3 ) CH (CH 3 ) SCH 3 80-82
1-109 Cl O CH 2 C (O) OH C (= NOCH 3 ) CH (CH 3 ) SCH 3 209-213
1-110 Cl O CH 2 C (O) NHCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 142-144
1-111 Cl O C (O) NHCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 46-49
1-112 Cl O CH 2 OC (O) N (CH 2 CH 3 ) 2 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 50: 6)
1-113 Cl O CH (CH 3 ) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 83: 10)
1-114 Cl O CH 2 SCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-115 Cl O CH (CH 3 ) OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 83: 17)
1-116 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) SCH 3 72-75
1-116 (* 3) * 1
1-116-(+) 94.5% ee [α] D 24.7 + 37.0 ° (CHCl 3 , c = 0.443)
1-116-(-) 99% ee [α] D 22.8 -45.60 ° (CHCl 3 , c = 0.120)
1-117 Cl O CH 2 OC (O) OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 51-64
1-118 Cl O CH 2 OC (O) OCH 2 CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-119 Cl O CH 2 OC (O) OCH 2 CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-120 Cl O C (S) NHCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 87: 13)
1-121 Cl O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 62-63
1-122 Cl O H C (= NOCH 3 ) CH {CH (CH 3 ) 2 } SCH 3 * 2 (～ 93: 7)
1-123 H O H C (= NOCH 3 ) CH (CH 3 ) SCH 3 110-120
1-124 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 46-49
1-125 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 86-88
1-126 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 2 CH 3 83-86
1-127 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 69-70
1-128 H O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-129 H O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-130 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 113-116
1-131 Cl O H C (= NOCH 2 CH 3 ) CH (CH 3 ) SCH 3 64-67
1-132 Cl O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH {CH (CH 3 ) 2 } SCH 3 * 2 (~ 3: 1)
1-133 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 125-127
1-134 Cl O CH 2 OC (O) OCH 3 C (= NOCH 2 CH 3 ) CH (CH 3 ) SCH 3 52-54
1-135 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 69-71
1-136 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 118-127
1-137 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 124-129
1-138 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) S (O) CH 2 CH 3 88-110
1-139 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 2 CH 3 138-143
1-140 Cl O H C (= NOCH 2 CH 3 ) CH (CH 3 ) SCH 2 CH 3 55-60
1-141 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 80-84
1-141-(+) 85% ee [α] D 23.0 + 12.03 ° (CHCl 3 , c = 0.142) 93-94
1-141-(-) 99% ee [α] D 22.9 -46.11 ° (CHCl 3 , c = 0.110) 96-97
1-142 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 * 1
1-143 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 * 1
1-144 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 5: 1)
1-145 CH 3 O C (O) C (= NOCH 3 ) CH (CH 3 ) SCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 * 1
1-146 Cl O H C (= NOCH 3 ) (D1-2a) 114-116
1-147 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 62-64
1-148 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 2 (~ 2: 1)
1-149 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 2 (～ 25: 3)
1-150 Cl O CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 65-67
1-151 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 50-52
1-152 Cl O CH 2 (D1-33a) C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 110-113
1-153 Cl O CH 2 (D1-34a) C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 * 1
1-154 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 2 (～ 8: 7)
1-155 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 1
1-156 CH 3 O H C (= NOCH 3 ) CH (CH 2 OCH 3 ) SCH 3 * 1
1-157 Cl O CH 2 (D1-32a) C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 80-82
1-158 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 34-35
1-159 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 42-43
1-160 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-161 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 64-65
1-162 CH 3 O H C (= NOCH 3 ) CH (CH 2 OCH 3 ) S (O) 2 CH 3 * 1
1-163 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-164 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 OCH 3 ) SCH 3 * 1
1-165 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 OCH 3 ) S (O) CH 3 * 1
1-166 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 OCH 3 ) S (O) 2 CH 3 * 1
1-167 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 2 (~ 3: 2)
1-168 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 1
1-169 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 126-127
1-170 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 1
1-171 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-172 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 1
1-173 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 4 (-58: 27: 15)
1-174 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
1-175 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 2 (～ 5: 3)
1-176 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-177 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 1
1-178 CH 3 O CH 2 CN C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 1
1-179 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 10: 1)
1-180 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 1
1-181 CH 3 O CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 1
1-182 CH 3 O CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 1
1-183 CH 3 O CH 2 CN C (= NOCH 2 CH 3 ) CH (CH 3 ) SCH 3 * 1
1-184 CH 3 O CH 2 CN C (= NOCH 2 CH 2 OCH 3 ) CH 2 SCH 3 * 1
1-185 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-186 Cl O CH 3 C (= NOH) CH (CH 3 ) SCH 3 163-165
1-187 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 1
1-188 CH 3 O CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 99-100
1-189 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 * 1
1-190 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 2 (~ 2: 1)
1-191 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 * 4 (-51: 25: 24)
1-192 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-193 Cl O H C (= NOCH 3 ) CH 2 {D1-7b (3-CF 3 )} 133-136
1-194 Cl O CH 3 C (= NOCH 2 CN) CH (CH 3 ) SCH 3 * 1
1-195 Cl O CH 3 C {= NOC (O) OCH 3 } CH (CH 3 ) SCH 3 * 1
1-196 Cl O CH 3 C {= NOC (O) CH 3 } CH (CH 3 ) SCH 3 * 1
1-197 CH 3 O H C (= NOCH 3 ) C (CH 3 ) 2 SCH 3 * 1
1-198 Cl O CH 3 C (= NOCH 2 OCH 3 ) CH (CH 3 ) SCH 3 * 1
1-199 Br O H C (= NOCH 3 ) CH (CH 3 ) SCH 3 85-88
1-200 CH 3 O H C (= NOCH 3 ) C (CH 3 ) 2 S (O) 2 CH 3 * 1
1-201 CH 3 O H C (= NOCH 3 ) CH 2 SCH 3 97-102
1-202 CH 3 O H C (= NOCH 3 ) CH 2 S (O) 2 CH 3 167-170
1-203 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) OS (O) 2 {D1-108b (Z = 4-CH 3 )} * 1
1-204 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) Cl 105-107
1-205 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S {D1-32b (3-CF 3 )} * 1
1-206 CH 3 S H C (= NOCH 3 ) CH (CH 3 ) SCH 3 73-76
1-207 CH 3 O H C (= NOCH 3 ) (D1-108a) * 2 (～ 2: 1)
1-208 Cl O C (O) CH (CH 3 ) SCH 3 C (= NOCH 3 ) CH 3 * 1
1-209 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 2 CF 3 70-72
1-210 Cl O CH 2 CH 3 C {= NNHS (O) 2 CH 3 } CH 3 41-44
1-211 CH 3 O H C {= NNHC (O) CH 3 } CH (CH 2 CH 3 ) SCH 3 138-142
1-212 CH 3 O H C (= NNHCH 2 CH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-213 CH 3 O H C {= NNHC (O) OCH 3 } CH (CH 2 CH 3 ) SCH 3 144-146
1-214 CH 3 O H C {= NNH (D1-37a)} CH (CH 3 ) SCH 3 49-51
1-215 Cl O CH 3 C {= NNH (D1-37a)} CH 3 39-41
1-216 CH 3 O H C {= NNH (D1-37a)} CH (CH 3 ) S (O) 2 CH 3 191-194
1-217 CH 3 O H C (= NNHCH 2 CF 3 ) CH (CH 2 CH 3 ) SCH 3 133-135
1-217 (* 3) 61-64
1-218 CH 3 O H C {= NNH (D1-108a)} CH (CH 2 CH 3 ) SCH 3 * 1
1-219 CH 3 O H C (= NNH 2 ) CH (CH 2 CH 3 ) SCH 3 127-130
1-220 CH 3 O H C {= NNHC (O) H} CH (CH 3 ) SCH 3 41-44
1-221 Cl O H C {= NNHC (O) OC (CH 3 ) 3 } CH (CH 3 ) SCH 3 49-50
1-222 Cl O H C {= NNHCH 2 CH = CH 2 } CH (CH 3 ) SCH 3 * 1
1-223 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) OCH 3 90-92
1-224 Cl O H C (= NOCH 3 ) {D1-108b (4-Cl)} 214-215
1-225 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 2 CH = CH 2 * 2 (~ 3: 1)
1-226 CH 3 O H C (= NOH) CH (CH 3 ) SCH 3 207-210
1-227 Cl O H CH [= NNHC (O) NH {D1-108b (2,6-Cl 2 )}] 211-214
1-228 CH 3 O H C {= NNHC (O) CH 3 } CH (CH 3 ) SCH 3 154-156
1-228 (* 3) 116-118
1-229 Cl O H C {= NNHC (O) CH 3 } CH (CH 3 ) SCH 3 154-156
1-230 CH 3 O C (O) Pr-c C [= NNHC (O) Pr-c] CH (CH 3 ) SCH 3 59-61
1-231 CH 3 O H C {= NNHC (O) OCH 2 (D1-108a)} CH (CH 3 ) SCH 3 * 1
1-231 (* 3) 103-105
1-232 Cl O H C (= NOCH 2 CH 2 CH 2 CH 2 CH 2 CH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-233 Cl O H C (= NOCH 2 Pr-c) CH (CH 3 ) SCH 3 * 2 (～ 2: 1)
1-234 CH 3 O H C (= NOCH 3 ) C (O) OCH 2 CH 3 120-122
1-235 CH 3 O H C (= NOCH 2 CH 3 ) CN 120-122
1-236 CH 3 O H C {= NNHC (O) CH 2 OCH 3 } CH (CH 3 ) SCH 3 64-66
1-237 CH 3 O H C {= NNHC (O) NHCH 2 CH 3 } CH (CH 3 ) SCH 3 * 1
1-238 Cl O H C {= NNH (c-Hex)} CH (CH 3 ) SCH 3 * 1
1-239 CH 3 O H C {= NN = C (CH 3 ) 2 } CH (CH 3 ) SCH 3 139-140
1-240 Cl O H C (= NOCH 3 ) CH (CH 2 CH = CH 2 ) S (O) 2 CH 3 * 2 (～ 7: 3)
1-241 Cl O H C [= NOCH 2 {D1-108b (4-OCH 3 )}] CH (CH 3 ) SCH 3 95-96
1-242 Cl O H C (= NOCH 2 C≡CH) CH (CH 3 ) SCH 3 * 2 (～ 2: 1)
1-243 Cl O H C (= NOH) CH (CH 3 ) SCH 3 198-199
1-244 CH 3 O H C (= NNH 2 ) CH (CH 3 ) SCH 3 88-90
1-245 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (Hex-c) * 1
1-246 CH 3 O H C {= NNHC (O) (D1-32a)} CH (CH 3 ) SCH 3 60-70
1-247 CH 3 O H C {= NNHC (O) (D1-108a)} CH (CH 3 ) SCH 3 * 2 (～ 6: 1)
1-248 CH 3 O H C {= N (D1-103m)} CH (CH 3 ) SCH 3 * 2 (~ 5: 2)
1-249 CH 3 O H C {= NNHC (O) CH 2 CN} CH (CH 3 ) SCH 3 * 2 (～ 10: 9)
1-250 CH 3 O H C {= NNH (D1-32a)} CH (CH 3 ) SCH 3 * 1
1-251 CH 3 O H C [= NNH {D1-108b (4-OCF 3 )] CH (CH 3 ) SCH 3 120-125
1-252 CH 3 O H C (= NOCH 3 ) C (O) NHCH 3 162-168
1-253 CH 3 O H C (= NOCH 3 ) C (O) CH 2 CH 3 * 1
1-254 CH 3 O H C (= NOCH 3 ) C {= NNHC (O) CH 3 } CH 2 CH 3 220 (decomp.)
1-255 CH 3 O H C (= NOCH 3 ) C (= NOCH 3 ) CH 2 CH 3 * 1
1-256 CH 3 O H C (= NOCH 2 CN) CH (CH 3 ) SCH 3 * 1
1-257 CH 3 O H C (= NOCH 2 CH 2 OCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-258 CH 3 O H C {= NNHC (O) CH 2 Pr-c} CH (CH 3 ) SCH 3 * 2 (~ 5: 2)
1-259 CH 3 O H C {= NNHC (O) CH 2 CH 3 } CH (CH 3 ) SCH 3 142-144
1-260 CH 3 O H C {= NN = CH (OCH 3 )} CH (CH 3 ) SCH 3 50-54
1-261 CH 3 O H C {= NNHC (O) CH 2 SCH 3 } CH (CH 3 ) SCH 3 * 2 (~ 3: 1)
1-262 CH 3 O H C {= NNHC (O) CH 3 } CH (CH 3 ) S (O) CH 3 121-123
1-263 CH 3 O H C {= NNHC (O) CH = CH 2 } CH (CH 3 ) SCH 3 50-52
1-264 Cl O H C (= NOCH 2 CH = CH 2 ) CH (CH 3 ) SCH 3 * 2 (～ 3: 2)
1-265 Cl O H C {= NOCH 2 C (O) OCH 3 } CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-266 Cl O H C {= NOCH 2 CH (CH 3 ) OH} CH (CH 3 ) SCH 3 * 2 (～ 3: 2)
1-267 Cl O H C {= NOCH 2 C (O) (D1-103n)} CH (CH 3 ) SCH 3 * 2 (~ 4: 1)
1-268 Cl O H C {= NOCH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 } CH (CH 3 ) SCH 3 * 2 (~ 1: 1)
1-269 Cl O H C {= NOCH 2 C (O) OH} CH (CH 3 ) SCH 3 145-160
1-270 CH 3 O H C (= NOCH 2 CH 3 ) CH (CH 3 ) SCH 3 * 2 (～ 1: 1)
1-271 CH 3 O H C (= NOCH 2 CH 2 CH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 3: 2)
1-272 CH 3 O H C (= NOCH 2 Pr-c) CH (CH 3 ) SCH 3 * 2 (~ 3: 2)
1-273 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S {D1-108b (4-OCH 3 )} * 1
1-274 CH 3 O H C (= NOCH 2 SCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 3: 1)
1-275 CH 3 O H C {= NNHC (S) NH (D1-108a)} CH (CH 3 ) SCH 3 * 2 (～ 6: 5)
1-276 CH 3 O H C {= NNHC (O) NHCH 2 CH = CH 2 } CH (CH 3 ) SCH 3 * 1
1-277 CH 3 O H C [= NNHC (O) NH {D1-108b (2-CF 3 )}] CH (CH 3 ) SCH 3 60-70
1-278 CH 3 O H C (= NNH 2 ) CH (CH 3 ) S (O) 2 CH 3 205-210
1-279 CH 3 O H C {= NNHC (O) CH 3 } CH (CH 3 ) S (O) 2 CH 3 182-185
1-280 CH 3 O H C {= NNHC (O) NHPen-c} CH (CH 3 ) SCH 3 * 2 (~ 2: 1)
1-281 CH 3 O H C {= NNHC (O) C≡CCH 3 } CH (CH 3 ) SCH 3 170-172
1-282 CH 3 O H C {= NNHC (O) CH 2 (D1-103o)} CH (CH 3 ) SCH 3 * 1
1-283 CH 3 O H C {= NNHC (O) CH 2 C (O) OCH 2 CH 3 } CH (CH 3 ) SCH 3 98-100
1-284 CH 3 O H C {= NNHC (O) CH 3 } CH 3 235-245
1-285 CH 3 O H C (= NOCH 3 ) CH (CH 2 C≡CH) S (O) 2 CH 3 * 1
1-286 C (O) CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-287 CH 3 O C (O) CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-288 CH 3 O H C (= NOCH 2 OCH 3 ) CH (CH 3 ) SCH 3 179-180
1-289 Cl O H C (= NOCH 2 CF 3 ) CH (CH 3 ) SCH 3 * 2 (～ 3: 2)
1-290 CH 3 O H C [= NNHC (O) {D1-108b (4-SCF 3 )}] CH (CH 3 ) SCH 3 * 2 (~ 4: 1)
1-291 CH 3 O H C {= NNHC (O) NH (D1-108a)} CH (CH 3 ) SCH 3 65-70
1-292 CH 3 O H C (= NNHCH 2 CH 3 ) CH (CH 3 ) SCH 3 * 1
1-293 CH 3 O H C {= NNHC (O) OCH 3 } CH (CH 3 ) SCH 3 * 1
1-294 H O H C {= NNHC (O) OCH 3 } CH (CH 3 ) SCH 3 50-52
1-295 CH 3 O H C {= NNHS (O) 2 (D1-108a)} CH (CH 3 ) SCH 3 148-150
1-296 CH 3 O H C {= NNHC (O) OCH 2 CH = CH 2 } CH (CH 3 ) SCH 3 * 1
1-297 CH 3 O H C {= NNHC (O) C (O) CH 3 } CH (CH 3 ) SCH 3 * 1
1-298 CH 3 O H C {= NNHC (O) (D1-103p)} CH (CH 3 ) SCH 3 * 2 (～ 4: 1)
1-298 (* 3) 160-175
1-299 CH 3 O CH 2 CH 2 OSi (CH 3 ) 2 C (CH 3 ) 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-300 CH 3 O CH 2 CH 2 OH C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 87-88
1-301 Cl O H C (= NOCH 3 ) CH (CH 3 ) {D1-108b (4-Cl)} 101-103
1-302 CH 3 O H C (= NOCH 2 SCH 3 ) CH 3 119-121
1-303 CH 3 O H C (= NOCH 2 CH 2 SCH 3 ) CH 3 82-84
1-304 CH 3 O H C {= NNHC (O) CH (= NOCH 3 )} CH (CH 3 ) SCH 3 80-83
1-304 (* 3) 104-108
1-305 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) CH 2 SCH 3 84-86
1-306 CF 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-307 C≡CSi (CH 3 ) 3 O CH 2 CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
1-308 C≡CH O CH 2 CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 99-100
1-309 CH 3 O H C {= NNHS (O) 2 CH 3 } CH (CH 3 ) SCH 3 * 1
1-309 (* 3) 105-110
1-310 CH 3 O H C {= NNHC (O) SCH (CH 3 ) 2 } CH (CH 3 ) SCH 3 45-48
1-311 CH 3 O CH 3 C {= NNHC (O) OCH 3 } CH (CH 3 ) SCH 3 120-130
1-312 CH 3 O CH 2 CH 2 OCH 3 C {= NNHC (O) OCH 3 } CH (CH 3 ) SCH 3 * 1
1-313 CH 3 O H C {= NN (CH 3 ) C (O) OC (CH 3 ) 3 } CH (CH 3 ) SCH 3 * 2 (～ 5: 3)
1-314 CH 3 O H C {= NOCH 2 C (O) OCH 2 CH 3 } CH (CH 3 ) SCH 3 * 1
1-315 CH 3 O H C {= NOCH 2 C (= NOCH 3 ) CH 3 } CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-316 CH 3 O H C {= NOCH 2 (D1-84a)} CH (CH 3 ) SCH 3 * 2 (～ 4: 1)
1-317 CH 3 O H C [= NOCH 2 {D1-33b (6-Cl)}] CH (CH 3 ) SCH 3 146-147
1-318 CH 3 O H C [= NOCH 2 {D1-108b (4-CN)}] CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-319 CH 3 O H C [= NOCH 2 {D1-108b (4-SCH 3 )}] CH (CH 3 ) SCH 3 * 2 (~ 7: 3)
1-320 CH 3 O H C “= NNHC (O) [D1-108b {2- (D1-103q)}]” CH (CH 3 ) SCH 3 * 1
1-321 CH 3 O H C (= NOCH 3 ) CH 2 (D1-98a) * 1
1-322 CH 3 O CH 3 C (= NOCH 3 ) CH 2 (D1-98a) * 1
1-323 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) CH 2 S (O) CH 3 * 2 (～ 1: 1)
1-324 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) CH 2 S (O) 2 CH 3 * 1
1-325 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 3 ) CH 2 SCH 3 * 2 (~ 3: 1)
1-326 Cl O H C (= NOCH 3 ) CH (CH 3 ) CH 2 SCH 3 * 1
1-327 CH 3 O H C (= NOCH 3 ) CH (D1-108a) CN * 1
1-328 CH 3 O H C (= NOCH 3 ) C (= CH 2 ) CH 3 * 1
1-329 CH 3 O H C (= NOCH 3 ) CH (OH) CH 2 CH 3 149-150
1-330 CH 3 O H C {= NN (CH 2 CH 3 ) C (O) CH 3 } CH (CH 3 ) SCH 3 * 1
1-331 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) SCH 2 C≡CH * 1
1-332 CH 3 O H C (= NOCH 3 ) CH 2 (D1-87a) 129-130
1-333 CH 3 O CH 3 C (= NOCH 3 ) CH 2 (D1-87a) * 2 (～ 4: 1)
1-334 CH 3 O CH 2 OCH 3 C (= NOCH 3 ) CH 2 (D1-98a) * 1
1-335 Cl O H C {= NOCH 2 CH (CH 3 ) CH 2 ONH 2 } CH (CH 3 ) SCH 3 * 1
1-336 CH 3 O CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 2 CH = CH 2 * 1
1-337 Cl O H C {= NOCH 2 C (O) CH 3 } CH (CH 3 ) SCH 3 * 1
1-338 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 2 CH = CH 2 * 2 (~ 1: 1)
1-339 CH 3 O H C {= NNHC (O) CH 2 CH 2 CH 3 } CH (CH 3 ) SCH 3 93-95
1-340 CH 3 O H C {= NNHC (O) CH (CH 3 ) 2 } CH (CH 3 ) SCH 3 36-39
1-341 CH 3 O H C {= NN = C (CH 3 ) OCH 3 } CH (CH 3 ) SCH 3 117-120
1-342 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 2 CH = CH 2 * 1
1-343 CH 3 O H C (= NOCH 3 ) CH (CH 2 CH 3 ) CH 2 SCH 3 * 1
1-344 CH 3 O H C (= NOCH 3 ) CH (CH 3 ) CH (CH 3 ) SCH 3 * 1
――――――――――――――――――――――――――――――――――
〔第６表〕
Figure JPOXMLDOC01-appb-C000202
 ――――――――――――――――――――――――――――――――――
No.     R3    A2    Ra              Rb-1                    m.p.(℃)
――――――――――――――――――――――――――――――――――
2-001   Cl   C-F    H               C(=NOCH3)CH(CH3)SCH3      97-99
2-002   Cl   C-F    CH2OC(O)OCH3    C(=NOCH3)CH(CH3)SCH3       49-50
2-003   CH3  C-F    H               C(=NOCH3)CH(CH3)SCH3     130-131
2-004   CH3   N     H               C(=NOCH3)CH(CH3)SCH3     116-118
―――――――――――――――――――――――――――――――――― [Table 6]
Figure JPOXMLDOC01-appb-C000202
 ――――――――――――――――――――――――――――――――――
No. R 3 A 2 R a R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
2-001 Cl CF H C (= NOCH 3 ) CH (CH 3 ) SCH 3 97-99
2-002 Cl CF CH 2 OC (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 49-50
2-003 CH 3 CF H C (= NOCH 3 ) CH (CH 3 ) SCH 3 130-131
2-004 CH 3 N H C (= NOCH 3 ) CH (CH 3 ) SCH 3 116-118
――――――――――――――――――――――――――――――――――
〔第７表〕
Figure JPOXMLDOC01-appb-C000203
 ――――――――――――――――――――――――――――――――――
No.      Y    R3        Ra             Rb-1                 m.p.(℃)
――――――――――――――――――――――――――――――――――
3-001    O    CH3      H           C(=NOCH3)CH2SCH3          101-104
3-002    O    Cl       CH2CH3      C(=NOCH3)CH2SCH3              *1
3-003    O   -CH2CH2CH2-          C(=NOCH3)CH2SCH3           118-121
3-004    O    Cl       H          C(=NOCH3)CH(CH3)SCH3       117-119
3-005    O    CH3      H           C(=NOCH3)CH(CH3)SCH3       90-100
3-005-(+)     94.7%e.e.  [α]D 19.2+89.36゜(CHCl3,c=0.218)    124-127
3-005-(-)     99%e.e.    [α]D 19.2-63.22゜(CHCl3,c=0.230)    129-131
3-006    O    CH3      CH2OCH2CH3   C(=NOCH3)CH(CH3)SCH3         *1
3-007    O    CH3      CH2OC(O)CH3  C(=NOCH3)CH(CH3)SCH3         *1
3-008    O    CH3      CH2C≡CH    C(=NOCH3)CH(CH3)SCH3          *1
3-009    O    CH3      H       C(=NOCH3)CH2{D1-108b(4-Cl)}   130-133
3-010    O   CH3     C(O)OCH3   C(=NOCH3)CH(CH3)SCH3     *2(～88:12)
3-011    O    CH3      H       C(=NOCH3)CH2{D1-7b(3-CF3)}    160-164
3-012    O    CH3     CH2Pr-c    C(=NOCH3)CH(CH3)SCH3      *2(～9:1)
3-013    O    CH3      H        C(=NOCH3)CH(CH3)S(O)CH3  *2(～56:44)
3-014    O    CH3      H       C(=NOCH3)CH(CH3)S(O)2CH3      155-162
3-015  O  CH3   H   C{=NNHC(O)OC(CH3)3}CH2{D1-108b(2,6-Cl2)} 187-190
3-016    O    CH3     H          C(=NOCH3)CH(CH2CH3)SCH3       83-84
3-016-(-)     95%e.e.       [α]D 24-71.9゜(CHCl3,c=0.322)
3-017    O    CH3      H          C(=NOCH3)CH(CH2CH3)S(O)2CH3    *1
3-018    O    Cl       H        C(=NOCH3)CH(CH2CH3)SCH3        95-98
3-018-(-)     95%e.e.       [α]D 24-31.7゜(CHCl3,c=0.637)
3-019    O    Cl       H        C(=NOCH3)CH(CH2CH3)S(O)CH3    99-107
3-020    O    Cl       H       C(=NOCH3)CH(CH2CH3)S(O)2CH3    99-102
3-021    O    Cl       H       C(=NOCH3)CH2SCH3              101-105
3-022    O    Cl       H       C(=NOCH3)CH2S(O)2CH3          164-166
3-023    O    CH3      H          C(=NOCH3)CH(CH2CH3)SCH2CF3      *1
3-024    O    CH3      H    C(=NOCH3)CH(CH2CH3)S{D1-32b(3-CF3)}   *1
3-025    O    CH3      H     C{=NNHC(O)OC(CH3)3}CH(CH3)SCH3   96-100
3-026    O    H        H           C(=NOCH3)CH(CH3)SCH3          *1
3-027    O    CH3      H          C(=NOCH3)CH(CH3)SCH2CH3      90-92
3-028    O    CH3      H          C(=NOCH3)CH(CH2CH3)OCH3        *1
3-029    O   CH3     H     C(=NOCH3)CH(CH2CH3)SCH2CH=CH2   *2(～7:3)
3-030    O    CH3    H    CH[=NNHC(O)NH{D1-108b(2,6-Cl2)}]   232-234
3-031    O    CH3     H        C{=NNHC(O)CH3}CH(CH3)SCH3     165-169
3-032    O    CH3    H            C(=NOCH3)CH(CH2CH3)S(Hex-c)     *1
3-033    O    CH3      H  C(=NOCH3)CH(CH2CH3)S{D1-108b(4-OCH3)}   *1
3-034    O    CH3      H       C(=NOCH3)CH(CH2C≡CH)S(O)2CH3      *1
3-035    O   CH3      H     C{=NNHC(O)(D1-108a)}CH(CH3)SCH3  120-130
3-036    O    CH3      H        C(=NNHCH2CF3)CH(CH3)SCH3       90-95
3-036(*3)                                                       *1
3-037    O   CH3     H  C{=NNHC(O)OCH2(D1-108a)}CH(CH3)SCH3  110-118
3-038    O    CH3      H      C{=NNH(D1-108a)}CH(CH3)SCH3    128-135
3-039    O    CH3    H   C[=NNH{D1-108b(4-NO2)}CH(CH3)SCH3   155-170
3-040    O    CH3      H       C{=NNHC(O)CH2OCH3}CH(CH3)SCH3     *1
3-041    O    CH3      H       C{=NNHC(O)CH2CN}CH(CH3)SCH3     59-61
3-042    O    CH3      H       C{=NNHC(O)NHCH2CH3}CH(CH3)SCH3  78-79
3-043    O    CH3      H     C{=NNHC(O)NHCH2CH=CH2}CH(CH3)SCH3    *1
3-044    O    CH3      H         C[=NNHC(O)Pr-c]CH(CH3)SCH3  115-120
3-045   O   CH3      H   C{=NNHC(S)NH(D1-108a)}CH(CH3)SCH3 *2(～2:1)
3-046    O    CH3     H            C(=NNH2)CH(CH3)SCH3       136-143
3-047    O    CH3      H       C(=NNHCH2CH=CH2)CH(CH3)SCH3        *1
3-048    O    CH3      H          C(=NNHCH2CH3)CH(CH3)SCH3        *1
3-049    O    CH3      H         C{=NNHC(O)OC(CH3)3}CH3      207-210
3-050    O    CH3     H    C{=NNHC(O)NH(D1-108a)}CH(CH3)SCH3   80-82
3-051    O    CH3      H       C(=NOCH3)CH2S(O)2CH3          153-159
3-052    O    Cl       H           C(=NOCH3)CH2(D1-98a)      128-130
3-053    O    Cl       H           C(=NOCH3)CH2(D1-87a)      133-134
3-054    O    Cl       H          C(=NOH)CH(CH3)SCH3    185(decomp.)
3-055    O    Cl      H          C(=NOCH2CF3)CH(CH3)SCH3   *2(～1:1)
―――――――――――――――――――――――――――――――――― [Table 7]
Figure JPOXMLDOC01-appb-C000203
 ――――――――――――――――――――――――――――――――――
No. Y R 3 R a R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
3-001 O CH 3 H C (= NOCH 3 ) CH 2 SCH 3 101-104
3-002 O Cl CH 2 CH 3 C (= NOCH 3 ) CH 2 SCH 3 * 1
3-003 O -CH 2 CH 2 CH 2 -C (= NOCH 3 ) CH 2 SCH 3 118-121
3-004 O Cl H C (= NOCH 3 ) CH (CH 3 ) SCH 3 117-119
3-005 O CH 3 H C (= NOCH 3 ) CH (CH 3 ) SCH 3 90-100
3-005-(+) 94.7% ee [α] D 19.2 + 89.36 ° (CHCl 3 , c = 0.218) 124-127
3-005-(-) 99% ee [α] D 19.2 -63.22 ° (CHCl 3 , c = 0.230) 129-131
3-006 O CH 3 CH 2 OCH 2 CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
3-007 O CH 3 CH 2 OC (O) CH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
3-008 O CH 3 CH 2 C≡CH C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
3-009 O CH 3 H C (= NOCH 3 ) CH 2 {D1-108b (4-Cl)} 130-133
3-010 O CH 3 C (O) OCH 3 C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 88: 12)
3-011 O CH 3 H C (= NOCH 3 ) CH 2 {D1-7b (3-CF 3 )} 160-164
3-012 O CH 3 CH 2 Pr-c C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 9: 1)
3-013 O CH 3 H C (= NOCH 3 ) CH (CH 3 ) S (O) CH 3 * 2 (-56: 44)
3-014 O CH 3 H C (= NOCH 3 ) CH (CH 3 ) S (O) 2 CH 3 155-162
3-015 O CH 3 H C {= NNHC (O) OC (CH 3 ) 3 } CH 2 {D1-108b (2,6-Cl 2 )} 187-190
3-016 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 83-84
3-016-(-) 95% ee [α] D 24 -71.9 ° (CHCl 3 , c = 0.322)
3-017 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 * 1
3-018 O Cl H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 95-98
3-018-(-) 95% ee [α] D 24 -31.7 ° (CHCl 3 , c = 0.637)
3-019 O Cl H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) CH 3 99-107
3-020 O Cl H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 99-102
3-021 O Cl H C (= NOCH 3 ) CH 2 SCH 3 101-105
3-022 O Cl H C (= NOCH 3 ) CH 2 S (O) 2 CH 3 164-166
3-023 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 2 CF 3 * 1
3-024 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) S {D1-32b (3-CF 3 )} * 1
3-025 O CH 3 H C {= NNHC (O) OC (CH 3 ) 3 } CH (CH 3 ) SCH 3 96-100
3-026 O H H C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 1
3-027 O CH 3 H C (= NOCH 3 ) CH (CH 3 ) SCH 2 CH 3 90-92
3-028 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) OCH 3 * 1
3-029 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 2 CH = CH 2 * 2 (～ 7: 3)
3-030 O CH 3 H CH [= NNHC (O) NH {D1-108b (2,6-Cl 2 )}] 232-234
3-031 O CH 3 H C {= NNHC (O) CH 3 } CH (CH 3 ) SCH 3 165-169
3-032 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (Hex-c) * 1
3-033 O CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) S {D1-108b (4-OCH 3 )} * 1
3-034 O CH 3 H C (= NOCH 3 ) CH (CH 2 C≡CH) S (O) 2 CH 3 * 1
3-035 O CH 3 H C {= NNHC (O) (D1-108a)} CH (CH 3 ) SCH 3 120-130
3-036 O CH 3 H C (= NNHCH 2 CF 3 ) CH (CH 3 ) SCH 3 90-95
3-036 (* 3) * 1
3-037 O CH 3 H C {= NNHC (O) OCH 2 (D1-108a)} CH (CH 3 ) SCH 3 110-118
3-038 O CH 3 H C {= NNH (D1-108a)} CH (CH 3 ) SCH 3 128-135
3-039 O CH 3 H C [= NNH {D1-108b (4-NO 2 )} CH (CH 3 ) SCH 3 155-170
3-040 O CH 3 H C {= NNHC (O) CH 2 OCH 3 } CH (CH 3 ) SCH 3 * 1
3-041 O CH 3 H C {= NNHC (O) CH 2 CN} CH (CH 3 ) SCH 3 59-61
3-042 O CH 3 H C {= NNHC (O) NHCH 2 CH 3 } CH (CH 3 ) SCH 3 78-79
3-043 O CH 3 H C {= NNHC (O) NHCH 2 CH = CH 2 } CH (CH 3 ) SCH 3 * 1
3-044 O CH 3 H C [= NNHC (O) Pr-c] CH (CH 3 ) SCH 3 115-120
3-045 O CH 3 H C {= NNHC (S) NH (D1-108a)} CH (CH 3 ) SCH 3 * 2 (~ 2: 1)
3-046 O CH 3 H C (= NNH 2 ) CH (CH 3 ) SCH 3 136-143
3-047 O CH 3 H C (= NNHCH 2 CH = CH 2 ) CH (CH 3 ) SCH 3 * 1
3-048 O CH 3 H C (= NNHCH 2 CH 3 ) CH (CH 3 ) SCH 3 * 1
3-049 O CH 3 H C {= NNHC (O) OC (CH 3 ) 3 } CH 3 207-210
3-050 O CH 3 H C {= NNHC (O) NH (D1-108a)} CH (CH 3 ) SCH 3 80-82
3-051 O CH 3 H C (= NOCH 3 ) CH 2 S (O) 2 CH 3 153-159
3-052 O Cl H C (= NOCH 3 ) CH 2 (D1-98a) 128-130
3-053 O Cl H C (= NOCH 3 ) CH 2 (D1-87a) 133-134
3-054 O Cl H C (= NOH) CH (CH 3 ) SCH 3 185 (decomp.)
3-055 O Cl H C (= NOCH 2 CF 3 ) CH (CH 3 ) SCH 3 * 2 (～ 1: 1)
――――――――――――――――――――――――――――――――――
〔第８表〕
Figure JPOXMLDOC01-appb-C000204
 ――――――――――――――――――――――――――――――――――
No.     R3          Ra           Rb                       m.p.(℃)
――――――――――――――――――――――――――――――――――
4-001   Cl            =C{OCH2OC(O)CH3}C(=NOCH3)CH2SCH3        53-55
4-002   Cl   =C{OCH2OC(O)N(CH2CH3)2}C(=NOCH3)CH(CH3)SCH3   *2(～5:3)
―――――――――――――――――――――――――――――――――― [Table 8]
Figure JPOXMLDOC01-appb-C000204
 ――――――――――――――――――――――――――――――――――
No. R 3 R a R b mp (℃)
――――――――――――――――――――――――――――――――――
4-001 Cl = C {OCH 2 OC (O) CH 3 } C (= NOCH 3 ) CH 2 SCH 3 53-55
4-002 Cl = C {OCH 2 OC (O) N (CH 2 CH 3 ) 2 } C (= NOCH 3 ) CH (CH 3 ) SCH 3 * 2 (~ 5: 3)
――――――――――――――――――――――――――――――――――
〔第９表〕
Figure JPOXMLDOC01-appb-C000205
 ――――――――――――――――――――――――――――――――――
No.     R3     R2    Ra   n      Rb-1                       m.p.(℃)
――――――――――――――――――――――――――――――――――
5-001   Cl   6-Cl    H    1      C(=NOCH3)CH(CH2CH3)SCH3     103-105
5-002   Cl   6-Cl    H    1  C{=NNHC(O)OC(CH3)3}CH(CH3)SCH3  104-106
―――――――――――――――――――――――――――――――――― [Table 9]
Figure JPOXMLDOC01-appb-C000205
 ――――――――――――――――――――――――――――――――――
No. R 3 R 2 R a n R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
5-001 Cl 6-Cl H 1 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 103-105
5-002 Cl 6-Cl H 1 C {= NNHC (O) OC (CH 3 ) 3 } CH (CH 3 ) SCH 3 104-106
――――――――――――――――――――――――――――――――――
〔第１０表〕
Figure JPOXMLDOC01-appb-C000206
 ――――――――――――――――――――――――――――――――――
No.     R3    R4      Ra        Rb-1                       m.p.(℃)
――――――――――――――――――――――――――――――――――
6-001   H     CH3     H         C(=NOCH3)CH(CH2CH3)SCH3        *1
6-002   CH3   Cl      CH3       C(=NOCH3)CH(CH2CH3)SCH3        *1
6-003   H     CH3     H     C{=NNHC(O)OC(CH3)3}CH(CH3)SCH3    39-42
―――――――――――――――――――――――――――――――――― [Table 10]
Figure JPOXMLDOC01-appb-C000206
 ――――――――――――――――――――――――――――――――――
No. R 3 R 4 R a R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
6-001 H CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
6-002 CH 3 Cl CH 3 C (= NOCH 3 ) CH (CH 2 CH 3 ) SCH 3 * 1
6-003 H CH 3 H C {= NNHC (O) OC (CH 3 ) 3 } CH (CH 3 ) SCH 3 39-42
――――――――――――――――――――――――――――――――――
〔第１１表〕
Figure JPOXMLDOC01-appb-C000207
 ――――――――――――――――――――――――――――――――――
No.     R3      Ra       Rb-1                              m.p.(℃)
――――――――――――――――――――――――――――――――――
7-001   CH3     H     C{=NNHC(O)OC(CH3)3}CH(CH3)S(O)2CH3    105-107
7-002   CH3     H     C(=NOCH3)CH(CH2CH3)S(O)2CH3           128-140
―――――――――――――――――――――――――――――――――― [Table 11]
Figure JPOXMLDOC01-appb-C000207
 ――――――――――――――――――――――――――――――――――
No. R 3 R a R b-1 mp (℃)
――――――――――――――――――――――――――――――――――
7-001 CH 3 H C {= NNHC (O) OC (CH 3 ) 3 } CH (CH 3 ) S (O) 2 CH 3 105-107
7-002 CH 3 H C (= NOCH 3 ) CH (CH 2 CH 3 ) S (O) 2 CH 3 128-140
――――――――――――――――――――――――――――――――――
〔第１２表〕
――――――――――――――――――――――――――――――――――
Ｎｏ．
　　プロトン核磁気共鳴ケミカルシフト値（ＣＤＣｌ３中）：σ（ｐｐｍ）
――――――――――――――――――――――――――――――――――
1-002;
(異性体比92)9.02-8.92(m,1H),8.63-8.56(m,1H),8.09(s,1H),8.05-7.94(m,1H),7.47-7.38(m,1H),4.62(q,J=7.2Hz,1H),3.95(dq,J=13.8,6.9Hz,1H), 3.77(s,3H), 3.56(dq,J=13.8,6.6Hz,1H),2.94(s,3H), 1.76(d,J=7.2Hz,3H), 1.30-1.19(m,3H)
(異性体比8)9.02-8.92(m,1H),8.63-8.56(m,1H),8.09(s,1H),8.05-7.94(m,1H),7.47-7.38(m,1H),4.90-4.78(m,1H),3.95(dq,J=13.8,6.9Hz,1H), 3.77(s,3H), 3.56(dq,J=13.8,6.6Hz,1H),3.02(s,3H), 1.76(d,J=7.2Hz,3H), 1.30-1.19(m,3H)
1-007;
(異性体比5)9.06(d,J=2.4Hz,1H),8.77(s,1H),8.58(dd,J=4.8,1.2Hz,1H),8.12(ddd,J=8.4,2.4,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),4.30-4.10(m,4H),3.75-3.65(m,2H),3.43(s,3H),2.35-2.20(m,2H),1.18(t,J=7.2Hz,3H),1.04(t,J=7.2Hz,3H)
(異性体比2)8.92(d,J=2.4Hz,1H),8.65-8.55(m,1H),8.05-7.95(m,1H),7.87(s,1H),7.42(dd,J=8.4,4.8Hz,1H),4.03(t,J=5.1Hz,2H),3.80(q,J=7.2Hz,2H),3.75-3.60(m,2H),3.20(s,3H),2.47(q,J=7.2Hz,2H),1.22(t,J=7.2Hz,3H),1.08(t,J=7.2Hz,3H)
1-008;
(異性体比4)9.08(d,J=2.4Hz,1H),8.68(s,1H),8.59(dd,J=4.8,1.2Hz,1H),8.13(ddd,J=8.4,2.4,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),4.68(t,J=5.4Hz,1H),4.30-4.00(m,4H),3.44(s,3H),3.34(s,3H),2.30-2.15(m,2H),1.18(t,J=7.2Hz,3H),1.03(t,J=7.2Hz,3H)
(異性体比1)8.94(d,J=2.4Hz,1H),8.46(dd,J=4.8,1.2Hz,1H),8.00-7.90(m,1H),7.42(dd,J=8.4,4.8Hz,1H),7.34(s,1H),4.30-3.80(m,5H),3.50-3.30(m,3H),3.22(s,3H),2.30-2.15(m,2H),1.30-1.20(m,6H)
1-009;
9.00-8.70(m,2H),8.61(dd,J=4.8,1.5Hz,2H),7.89(ddd,J=8.4,2.7,1.5Hz,1H),7.68(s,1H),7.40(dd,J=8.4,4.8Hz,1H),7.32(dd,J=4.8,1.5Hz,2H),3.89(s,3H),3.82(q,J=7.2Hz,2H),1.24(t,J=7.2Hz,3H)
1-010;
(異性体比7)8.92(d,J=2.7Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.09(s,1H),8.02(ddd,J=8.7,2.7,1.2Hz,1H),7.44(dd,J=8.7,4.8Hz,1H),4.60-4.40(m,2H),3.70(s,3H),3.55(s,2H),2.28(t,J=2.4Hz,1H),1,93(s,3H)
(異性体比1)8.92(d,J=2.7Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.09(s,1H),8.02(ddd,J=8.7,2.7,1.2Hz,1H),7.44(dd,J=8.7,4.8Hz,1H),4.80-4.60(m,2H),4.08(s,3H),3.56(s,2H),2.28(t,J=2.4Hz,1H),2.15(s,3H)
1-011;
8.98(d,J=2.7Hz,1H),8.58(dd,J=4.8,1.5Hz,1H),8.26(s,1H),8.01(ddd,J=8.1,2.7,1.5Hz,1H),7.41(dd,J=8.1,4.8Hz,1H),4.60-4.40(m,2H),4.08(d,J=12.3Hz,1H),3.95(d,J=12.3Hz,1H),3.78(s,3H),2.59(s,3H),2.28(t,J=2.4Hz,1H)
1-012;
8.97(d,J=2.7Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.16(s,1H),7.98(ddd,J=8.1,2.7,1.2Hz,1H),7.41(dd,J=8.1,4.8Hz,1H),4.60-4.40(m,4H),3.82(s,3H),2.88(s,3H),2.29(t,J=2.4Hz,1H)
1-014(*3);
8.92(d,J=2.7Hz,1H),8.60(dd,J=4.8Hz,1.2Hz,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.88(s,1H),7.43(dd,J=8.4,4.8Hz,1H),4.02(t、J=4.8Hz,2H),3.77(q,J=7.2Hz,2H),3.36(t,J=4.8Hz,2H),3.19(s,3H),1.99(s,3H),1.22(t,J=7.2Hz,3H)
1-016;
(異性体比3)9.08(d,J=2.7Hz,1H),8.66(s,1H),8.65-8.55(m,1H),8.20-8.10(m,1H),7.50-7.40(m,1H),4.66(t,J=5.4Hz,1H),4.20-4.00(m,2H),3.89(d,J=5.4Hz,2H),3.41(s,6H),1.89(s,3H),1.30-1.15(m,3H)
(異性体比2)8.94(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.20-8.10(m,1H),7.89(s,1H),7.50-7.40(m,1H),4.30-4.20(m,1H),3.78(q,J=7.2Hz,2H),3.89(d,J=5.4Hz,2H),3.21(s,6H),1.99(s,3H),1.30-1.15(m,3H)
1-017;
(異性体比3)9.04(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.15-8.00(m,2H),7.50-7.35(m,1H),4.72(s,2H),3.79(q,J=7.2Hz,2H),1.98(s,3H),1.20(t,J=7.2Hz,3H)
(異性体比2)8.98(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.15-8.00(m,1H),7.98(s,1H),7.50-7.35(m,1H),4.55(s,2H),3.79(q,J=7.2Hz,2H),2.01(s,3H),1.26(t,J=7.2Hz,3H)
1-018;
8.70-8.60(m,1H),8.57(d,J=3.0Hz,1H),8.52(dd,J=4.8,1.2Hz,1H),7.83(s,1H),7.82(ddd,J=8.4,3.0,1.2Hz,1H),7.75-7.60(m,2H),7.34(dd,J=8.4,4.8Hz,1H),7.30-7.20(m,1H),4.20-4.05(m,2H),4.00(s,3H),1.26(t,J=7.2Hz,3H)
1-020(*3);
9.01(d,J=2.4Hz,1H),8.61(dd,J=4.8,1.2Hz,1H),8.08(ddd,J=8.4,2.4,1.2Hz,1H),8.01(s,1H),7.44(dd,J=8.4,4.8Hz,1H),4.85(d,J=11.8Hz,1H),4.78(d,J=11.8Hz,1H),4.00-3.75(m,2H),2.35(s,3H),2.03(s.3H),1.22(t,J=7.2Hz,3H)
1-023;
(異性体比3)8.93(d,J=2.7Hz,1H),8.61(dd,J=4.8,1.2Hz,1H),8.51(s,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),4.10-3.35(m,3H),2.80-2.65(m,2H),2.11(s,3H),1.45-1.10(m,9H)
(異性体比2)9.01(d,J=2.7Hz,1H),8.61(dd,J=4.8,1.2Hz,1H),8.15(s,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),4.10-3.35(m,3H),2.49(q,J=7.2Hz,2H),2.11(s,3H),1.45-1.10(m,9H)
1-024;
(異性体比27)9.05-9.00(m,1H),8.75-8.65(m,1H),8.15(s,1H),8.05-7.95(m,1H),7.50-7.40(m,1H),4.00-3.75(m,2H),3.00-2.60(m,4H),2.20-2.00(m,6H),1.30-1.15(m,3H)
(異性体比25)9.05-9.00(m,1H),8.75-8.65(m,1H),8.25(s,1H),8.05-7.95(m,1H),7.50-7.40(m,1H),4.00-3.75(m,2H),3.00-2.60(m,4H),2.20-2.00(m,6H),1.30-1.15(m,3H)
1-029;
(異性体比85)8.89(d,J=2.7Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.03(s,1H),8.00(ddd,J=8.1,2.7,1.2Hz,1H),7.43(dd,J=8.1,4.8Hz,1H),4.09(q,J=7.2Hz,1H),3.75(s,3H), 3.32(s,3H), 1.90(s,3H), 1.48(d,J=7.2Hz,3H)
(異性体比15)8.89(d,J=2.7Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.13(s,1H),8.00(ddd,J=8.1,2.7,1.2Hz,1H),7.43(dd,J=8.1,4.8Hz,1H),4.38-4.27(m,1H),3.97(brs,3H), 3.50(brs,3H), 2.20(brs,3H), 1.63-1.55(m,3H)
1-030;
(異性体比5)8.99-8.89(m,1H),8.64-8.54(m,1H),8.06-7.95(m,1H),7.99(s,1H),7.48-7.36(m,1H),4.22-4.00(m,1H),3.76(s,3H), 3.32(s,3H), 2.57(s,3H), 1.52(d,J=7.5Hz,3H)
(異性体比4)8.99-8.89(m,1H),8.64-8.54(m,1H),8.18(s,1H),8.06-7.95(m,1H),7.48-7.36(m,1H),4.22-4.00(m,1H),3.73(s,3H), 3.32(s,3H), 2.59(s,3H), 1.49(d,J=7.5Hz,3H)
(異性体比1)8.99-8.89(m,1H),8.64-8.54(m,1H),8.11(s,1H),8.06-7.95(m,1H),7.48-7.36(m,1H),4.22-4.00(m,1H),3.84(brs,3H), 3.50(brs,3H), 2.65(brs,3H), 1.73-1.60(m,3H)
1-031;
(異性体比9)8.95(d,J=2.7Hz,1H),8.58(d,J=4.8Hz,1H),8.11(s,1H),7.99-7.93(m,1H),7.41(dd,J=8.1,4.8Hz,1H),4.64(q,J=7.2Hz,1H),3.76(s,3H), 3.32(s,3H), 2.94(s,3H), 1.76(d,J=7.2Hz,3H)
(異性体比1)8.95(d,J=2.7Hz,1H),8.58(d,J=4.8Hz,1H),8.09(s,1H),7.99-7.93(m,1H),7.41(dd,J=8.1,4.8Hz,1H),4.91-4.81(m,1H),4.09(brs,3H), 3.51(brs,3H), 3.03(brs,3H), 1.82-1.74(m,3H)
1-033;
(異性体比5)8.97(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.24(s,1H),8.00(ddd,J=8.4,2.4,1.2Hz,1H),7.43(dd,J=8.4,4.8Hz,1H),4.60-4.40(m,2H),3.83(s,3H),2.71(s,3H),2.29(t,J=2.4Hz,1H),1.75-1.60(m,4H)
(異性体比1)9.00(d,J=2.1Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.25(s,1H),8.06-8.00(m,1H),7.43(dd,J=8.4,4.8Hz,1H),4.60-4.40(m,2H),3.83(s,3H),3.11(s,3H),2.26(t,J=2.1Hz,1H),1.75-1.60(m,4H)
1-034;
8.89(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),3.93(q,J=7.2Hz,2H),3.57(s,2H),3.34(s,3H),1.94(s,3H),1.02(t,J=7.2Hz,3H)
1-037;
(異性体比4)8.96(d,J=2.7Hz,1H),8.57(dd,J=4.8,1.2Hz,1H),8.24(s,1H),7.97(ddd,J=8.4,2.7,1.2Hz,1H),7.40(dd,J=8.4,4.8Hz,1H),4.15-3.90(m,4H),3.34(s,3H),2.61(s,3H),1.02(t,J=7.2Hz,3H)
(異性体比1)8.96(d,J=2.7Hz,1H),8.57(dd,J=4.8,1.2Hz,1H),8.24(s,1H),7.97(ddd,J=8.4,2.7,1.2Hz,1H),7.40(dd,J=8.4,4.8Hz,1H),4.15-3.90(m,2H),3.48(q,J=7.2Hz,2H),3.34(s,3H),2.61(s,3H),1.20(t,J=7.2Hz,3H)
1-042;
(異性体比3)8.93(d,J=2.7Hz,1H),8.63-8.57(m,1H),8.07-7.93(m,1H),7.96(s,1H),7.44(dd,J=8.1,4.8Hz,1H),4.19-4.03(m,1H),3.93-3.61(m,2H), 3.75(s,3H), 2.57(s,3H), 1.51(d,J=7.2Hz,3H), 1.30-1.15(m,3H)
(異性体比2)8.97(d,J=2.7Hz,1H),8.58-8.53(m,1H),8.15(s,1H),8.07-7.93(m,1H),7.40(dd,J=8.1,4.8Hz,1H),4.19-4.03(m,1H),3.93-3.61(m,2H), 3.72(s,3H), 2.58(s,3H), 1.49(d,J=7.2Hz,3H), 1.30-1.15(m,3H)
1-043;
8.91(d,J=2.7Hz,1H),8.58(d,J=4.8Hz,1H),8.03-7.95(m,2H),7.42(dd,J=8.7,4.8Hz,1H),5.09(brs,2H),3.70(brs,3H), 3.54(brs,2H),3.48(s,3H), 1.93(brs,3H)
1-044;
(異性体比85)8.95(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.07(s,1H),8.02-7.94(m,1H),7.41(dd,J=8.1,4.8Hz,1H),5.10(brs,2H),4.47(brs,2H), 3.82(brs,3H),3.49(s,3H), 2.85(s,3H)
(異性体比15)9.00(d,J=2.1Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.41(s,1H),8.09-7.94(m,1H),7.41(dd,J=8.1,4.8Hz,1H),5.10(brs,2H),4.47(brs,2H), 3.82(brs,3H),3.44(s,3H), 3.04(s,3H)
1-045;
8.90(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.07-7.93(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.14(brs,2H),3.80-3.65(m,5H), 3.53(brs,2H),1.93(brs,3H), 1.35-1.20(m,3H)
1-046;
(異性体比92)9.00-8.90(m,1H),8.67-8.57(m,1H),8.16(s,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.45(dd,J=8.4,4.8Hz,1H),4.63(brs,2H),3.71(brs,3H), 3.55(brs,2H),1.93(brs,3H)
(異性体比8)
9.00-8.90(m,1H),8.67-8.57(m,1H),8.39(s,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.45(dd,J=8.4,4.8Hz,1H),4.68(brs,2H),3.83(s,3H), 3.09(s,2H),2.00(s,3H)
1-047;
8.88(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.03(s,1H),7.97(ddd,J=8.4,2.4,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),3.69(d,J=7.2Hz,2H),3.59(s,2H),3.34(s,3H),1.95(s,3H),0.95-0.80(m,1H),0.40-0.25(m,2H),0.15-0.05(m,2H)
1-048;
8.89(d,J=2.4Hz,1H),8.58(dd,J=4.8Hz,1.2Hz,1H),8.03(s,1H),7.98(ddd,J=8.4,2.4,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),4.02(t、J=4.8Hz,2H),3.58(s,2H),3.40-3.30(m,2H),3.34(s,3H),3.14(s,3H),1.94(s,3H)
1-050;
8.91(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.11(s,1H),7.99(ddd,J=8.4,2.4,1.2Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),4.96(s,2H),3.55(s,2H),3.36(s,3H),1.94(s,3H),1.90(s,3H)
1-051;
8.89(d,J=2.7Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),4.03(t,J=7.2Hz,2H),3.57(s,2H),3.34(s,3H),2.47(t,J=7.2Hz,2H),1.99(s,3H),1.98(s,3H)
1-053;
8.97(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.5Hz,1H),8.25(s,1H),8.00(ddd,J=8.4,2.4,1.5Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),5.05-4.95(m,2H),4.15-4.00(m,2H),3.35(s,3H),3.11(s,3H),2.67(s,3H)
1-054;
(異性体比3)8.85(d,J=2.4Hz,1H),8.65-8.57(m,1H),8.04-7.90(m,1H),7.83(s,1H),7.43(dd,J=8.1,4.8Hz,1H),4.04(s,3H),3.33(s,3H),2.26(s,3H)
(異性体比2)8.91(d,J=2.1Hz,1H),8.65-8.57(m,1H),8.04-7.90(m,1H),7.95(s,1H),7.43(dd,J=8.1,4.8Hz,1H),3.82(s,3H),3.32(s,3H),2.36(s,3H)
1-055;
(異性体比50)8.95(d,J=2.4Hz,1H),8.70-8.55(m,1H),8.13(s,1H),8.05-7.95(m,1H),7.41(dd,J=8.4,4.8Hz,1H),5.00(s,2H),4.54(s,2H),3.40-3.30(m,3H),3.11(s,3H),2.97(s,3H)
(異性体比7)9.00(d,J=3.0Hz,1H),8.70-8.55(m,1H),8.46(s,1H),8.05-7.95(m,1H),7.41(dd,J=8.4,4.8Hz,1H),5.02(s,2H),4.54(s,2H),3.40-3.30(m,3H),3.28(s,3H),3.05(s,3H)
1-056;
8.93(d,J=2.7Hz,1H),8.63(dd,J=4.8,1.2Hz,1H),8.20(s,1H),8.01(ddd,J=8.1,2.7,1.2Hz,1H),7.46(dd,J=8.1,4.8Hz,1H),4.75(d,J=17.4Hz,1H),4.52(d,J=17.4Hz,1H),4.12(q,J=7.2Hz,1H),3.76(s,3H),1.92(s,3H), 1.52(d,J=7.2Hz,3H)
1-056(*3);
(異性体比81)8.91(d,J=2.4Hz,1H),8.63(dd,J=4.8,1.2Hz,1H),8.36(brs,1H),8.00(ddd,J=8.1,2.4,1.2Hz,1H),7.46(dd,J=8.1,4.8Hz,1H),4.95-4.32(m,2H),3.88(brs,3H),4.05-3.30(m,1H),1.91(brs,3H), 1.41(d,J=7.2Hz,3H)
(異性体比19)8.97(d,J=2.4Hz,1H),8.67-8.59(m,1H),8.21(brs,1H),8.06-7.96(m,1H),7.50-7.40(m,1H),4.95-4.32(m,2H),4.03(brs,3H),4.05-3.30(m,1H),2.18(brs,3H), 1.70-1.50(m,3H)
1-057(*3);
9.44(brs,1H),8.98(d,J=2.4Hz,1H),8.71(s,1H),8.55(dd,J=4.8,1.2Hz,1H),7.99(ddd,J=8.1,2.4,1.2Hz,1H),7.39(dd,J=8.1,4.8Hz,1H),4.17-4.01(m,1H),4.09(s,3H),2.10(s,3H), 1.52(d,J=7.2Hz,3H)
1-058;
8.98-8.91(m,1H),8.65-8.57(m,1H),8.08(s,1H),8.07-8.00(m,1H),7.44(dd,J=8.4,4.8Hz,1H),4.88(brs,2H),3.70(s,3H), 3.53(s,2H),2.26(s,3H), 1.93(s,3H)
1-059;
8.89(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.1,2.4,1.2Hz,1H),7.94(s,1H),7.43(dd,J=8.1,4.8Hz,1H),6.00-5.81(m,1H),5.30-5.16(m,2H),4.41-4.28(m,2H),3.69(s,3H),3.54(s,2H), 1.92(s,3H)
1-060;
8.90(d,J=2.7Hz,1H),8.63(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,1H),7.96(s,1H),7.45(dd,J=8.4,4.8Hz,1H),4.42(sep,J=6.3Hz,1H),3.38(s,3H),1.15(d,J=6.3Hz,6H)
1-065;
8.92(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.44(dd,J=8.4,4.8Hz,1H),3.69(s,3H),3.63(d,J=6.6Hz,2H),3.53(s,2H),1.93(s,3H),1.10-1.00(m,1H),0.60-0.45(m,2H),0.30-0.20(m,2H)
1-066;
(異性体比87)8.94(d,J=2.1Hz,1H),8.65-8.55(m,1H),8.10-7.95(m,1H),7.89(s,1H),7.44(dd,J=8.4,4.8Hz,1H),6.20-6.00(m,1H),4.00-3.25(m,8H),2.20-1.85(m,3H),1.40-1.20(m,3H)
(異性体比13)8.94(d,J=2.1Hz,1H),8.65-8.55(m,1H),8.10-7.95(m,1H),7.89(s,1H),7.44(dd,J=8.4,4.8Hz,1H),5.80-5.60(m,1H),4.00-3.25(m,8H),2.20-1.85(m,3H),1.40-1.20(m,3H)
1-067;
8.75-8.65(m,1H),8.60-8.50(m,1H),7.90-7.70(m,1H),7.50-7.30(m,7H),5.00-4.80(m,2H),3.70-3.55(m,5H),1.95-1.85(m,3H)
1-068;
(異性体比5)8.94(d,J=2.7Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.42(dd,J=8.4,4.8Hz,1H),3.99(s,3H),3.85(s,3H),3.64(s,2H),2.14(s,3H)
(異性体比1)9.00-8.90(m,1H),8.60-8.50(m,1H),8.05-7.95(m,2H),7.40-7.35(m,1H),3.99(s,3H),3.85(s,3H),3.64(s,2H),2.14(s,3H)
1-069;
8.74(d,J=2.4Hz,1H),8.55(dd,J=4.8,1.2Hz,1H),7.99(ddd,J=8.4,2.4,1.2Hz,1H),7.63(s,1H),7.50-7.20(m,5H),5.10(s,2H),3.69(s,3H),3.57(s,2H),1.92(s,3H)
1-070;
8.77(d,J=2.7Hz,1H),8.55(dd,J=4.8,1.2Hz,1H),7.90(ddd,J=8.1,2.7,1.2Hz,1H),7.59(s,1H),7.39(dd,J=8.1,4.8Hz,1H),7.35-7.15(m,4H),4.89(brs,2H),3.69(s,3H),3.57(s,2H),1.93(s,3H)
1-071;
8.77(d,J=2.7Hz,1H),8.56(dd,J=4.8,1.2Hz,1H),7.87(ddd,J=8.4,2.7,1.2Hz,1H),7.56(s,1H),7.50-7.20(m,5H),4.88(brs,2H),3.68(s,3H),3.56(s,2H),1.90(s,3H)
1-073;
8.90(d,J=2.7Hz,1H),8.61(dd,J=4.8,1.2Hz,1H),8.10-7.90(m,2H),7.44(dd,J=8.4,4.8Hz,1H),5.80-5.60(brs,2H),3.90-3.60(brs,3H),3.57(s,2H),2.11(s,3H),2.05-1.85(brs,3H)
1-074;
(異性体比5)8.97(d,J=2.7Hz,1H),8.63(dd,J=4.8,1.2Hz,1H),8.17(s,1H),8.00(ddd,J=8.1,2.7,1.2Hz,1H),7.44(dd,J=8.1,4.8Hz,1H),5.90-5.70(m,1H),4.20-3.40(m,5H),2.20-1.85(m,3H),1.35-1.10(m,3H)
(異性体比1)9.01(d,J=2.7Hz,1H),8.84(s,1H),8.54(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.1,2.7,1.2Hz,1H),7.44(dd,J=8.1,4.8Hz,1H),5.90-5.70(m,1H),4.20-3.40(m,5H),2.20-1.85(m,3H),1.35-1.10(m,3H)
1-075;
(異性体比1)9.05-8.90(m,1H),8.65-8.50(m,1H),8.05-7.90(m,2H),7.41(dd,J=8.4,4.8Hz,1H),6.10-5.90(m,1H),4.20-3.90(m,2H),3.79(s,3H),3.60-3.45(m,3H),2.67(s,3H),1.40-1.20(m,3H)
(異性体比1)9.05-8.90(m,1H),8.65-8.50(m,1H),8.05-7.90(m,2H),7.41(dd,J=8.4,4.8Hz,1H),6.10-5.90(m,1H),4.20-3.90(m,2H),3.79(s,3H),3.60-3.45(m,3H),2.44(s,3H),1.40-1.20(m,3H)
1-077;
8.91(d,J=2.7Hz,1H),8.59(d,J=4.8Hz,1H),8.03(s,1H),8.02-7.98(m,1H),7.43(dd,J=8.4,4.8Hz,1H),5.20(d,J=9.6Hz,1H),4.97(d,J=9.6Hz,1H),4.20-4.00(m,1H),3.76(s,3H),3.49(s,3H),1.94(s,3H),1.52(d,J=7.2Hz,3H)
1-077(*3);
(異性体比5)8.89(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.30-7.95(m,2H),7.44(dd,J=8.4,4.8Hz,1H),5.50-4.70(m,2H),3.92(brs,3H),3.80-3.60(m,1H),3.46(s,3H),1.90(brs,3H),1.50-1.30(m,3H)
(異性体比1)8.94(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.30-7.95(m,2H),7.42(dd,J=8.4,4.8Hz,1H),5.50-4.70(m,2H),3.95(s,3H),3.55-3.45(m,1H),3.39(s,3H),1.90(brs,3H),1.50-1.30(m,3H)
1-079;
8.96(d,J=2.7Hz,1H),8.63(dd,J=4.8,1.2Hz,1H),8.14(s,1H),8.02(ddd,J=8.4,2.7,1.2Hz,1H),7.46(dd,J=8.4,4.8Hz,1H),5.85-5.60(m,1H),4.20-3.60(m,4H),1.94(brs,3H),1.65-1.45(m,3H),1.13(d,J=6.0Hz,3H)
1-080;
(異性体比1)9.00-8.80(m,1H),8.70-8.55(m,1H),8.10-7.95(m,2H),7.55-7.40(m,1H),3.87(s,3H),3.30(s,3H),2.90-2.50(m,4H),2.05(s,3H)
(異性体比1)9.00-8.80(m,1H),8.70-8.55(m,1H),8.10-7.95(m,2H),7.55-7.40(m,1H),3.69(brs,3H),3.32(brs,3H),2.90-2.50(m,4H),2.12(brs,3H)
1-081;
8.82(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),7.95(ddd,J=8.4,2.4,1.2Hz,1H),7.85(s,1H),7.45-7.30(m,6H),5.45-5.25(m,1H),5.20-5.05(m,1H),4.75(s,2H),4.10-4.00(m,1H),3.75(s,3H),1.94(brs,3H),1.52(d,J=7.2Hz,3H)
1-082;
(異性体比3)9.05-8.95(m,1H),8.70-8.55(m,1H),8.21(s,1H),8.10-7.95(m,1H),7.50-7.35(m,1H),4.90-4.45(m,2H),4.30-4.10(m,1H),3.79(s,3H),2.56(s,3H),1.65-1.50(m,3H)
(異性体比2)9.05-8.95(m,1H),8.70-8.55(m,1H),8.35(s,1H),8.10-7.95(m,1H),7.50-7.35(m,1H),4.90-4.45(m,2H),4.30-4.10(m,1H),3.78(s,3H),2.60(s,3H),1.65-1.50(m,3H)
1-084;
8.96(d,J=2.7Hz,1H),8.70-8.55(m,1H),8.09(s,1H),8.05-7.95(m,1H),7.43(dd,J=8.4,4.8Hz,1H),5.68(brs,2H),4.47(brs,2H),3.84(brs,3H),2.89(brs,3H),2.10(s,3H)
1-085;
(異性体比4)9.00-8.90(m,1H),8.65-8.50(m,1H),8.10-7.95(m,2H),7.42(dd,J=8.4,4.8Hz,1H),4.35-4.15(m,3H),3.97(s,3H),3.80-3.60(m,1H),2.19(s,3H),1.55-1.50(m,3H),1.35-1.25(m,3H),1.13(d,J=6.0Hz,3H)
(異性体比1)9.00-8.90(m,1H),8.65-8.50(m,1H),8.10-7.95(m,2H),7.42(dd,J=8.4,4.8Hz,1H),4.35-4.15(m,3H),3.92(s,3H),3.80-3.60(m,1H),2.15(s,3H),1.55-1.50(m,3H),1.35-1.25(m,3H),1.13(d,J=6.0Hz,3H)
1-086;
8.88(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.90-5.50(m,2H),4.25-3.70(m,4H),1.95(brs,3H),1.53(d,J=7.2Hz,3H),1.21(s,9H)
1-087;
8.90(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.10-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.80-5.60(m,2H),4.12(q,J=7.2Hz,1H),3.77(brs,3H),2.10(s,3H),1.93(brs,3H),1.53(d,J=7.2Hz,3H)
1-088;
(異性体比20)9.00-8.85(m,1H),8.65-8.50(m,1H),8.09(s,1H),8.05-7.90(m,1H),7.50-7.35(m,1H),5.80-5.35(m,2H),4.67(q,J=7.2Hz,1H),3.81(s,3H),2.92(s,3H),2.10(s,3H),1.77(d,J=7.2Hz,3H)
(異性体比13)9.00-8.85(m,1H),8.65-8.50(m,1H),8.12(s,1H),8.05-7.90(m,1H),7.50-7.35(m,1H),5.60-4.90(m,2H),4.76(q,J=7.2Hz,1H),3.98(s,3H),2.95(s,3H),2.10(s,3H),1.76(d,J=7.2Hz,3H)
1-089;
8.89(d,J=2.7Hz,1H),8.56(d,J=4.8,1.2Hz,1H),8.18(s,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),5.40-4.95(m,2H),4.09(q,J=7.2Hz,1H),3.90-3.80(m,2H),3.75(s,3H),3.65-3.55(m,2H),3.39(s,3H),1.93(s,3H),1.51(d,J=7.2Hz,3H)
1-090;
(異性体比4)8.94(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.10-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.40-4.80(m,2H),4.30-3.90(m,1H),3.77(s,3H),3.47(s,3H),2.57(s,3H),1.56(d,J=7.2Hz,3H)
(異性体比1)8.96(d,J=2.4Hz,1H),8.56(dd,J=4.8,1.2Hz,1H),8.16(s,1H),8.10-7.95(m,1H),7.60-7.35(m,1H),5.40-4.80(m,2H),4.30-3.90(m,4H),3.50(s,3H),2.57(s,3H),1.52(d,J=7.2Hz,3H)
1-090(*3);
(異性体比6)9.00-8.85(m,1H),8.60-8.55(m,1H),8.50-7.95(m,2H),7.50-7.35(m,1H),5.35-4.60(m,2H),3.91(s,3H),3.80-3.40(m,4H),2.63(brs,3H),1.60-1.30(m,3H)
(異性体比1)9.00-8.85(m,1H),8.60-8.55(m,1H),8.50-7.95(m,2H),7.50-7.35(m,1H),5.35-4.60(m,2H),4.01(s,3H),3.80-3.30(m,4H),2.55(brs,3H),1.60-1.30(m,3H)
1-091;
8.96(d,J=2.4Hz,1H),8.57(dd,J=4.8,1.2Hz,1H),8.10(s,1H),8.05-7.90(m,1H),7.41(dd,J=8.4,4.8Hz,1H),5.40-5.20(m,1H),4.95-4.75(m,1H),4.69(q,J=7.2Hz,1H),3.81(s,3H),3.49(s,3H),2.90(s,3H),1.77(d,J=7.2Hz,3H)
1-092;
(異性体比4)8.86(d,J=2.7Hz,1H),8.65-8.50(m,1H),8.05-7.90(m,1H),7.79(s,1H),7.50-7.20(m,6H),5.55-4.60(m,4H),4.30-4.00(m,1H),3.77(s,3H),2.60(s,3H),1.54(d,J=7.2Hz,3H)
(異性体比3)8.90(d,J=2.7Hz,1H),8.65-8.50(m,1H),8.07(s,1H),8.05-7.90(m,1H),7.50-7.20(m,6H),5.55-4.60(m,4H),4.30-4.00(m,1H),3.77(s,3H),2.58(s,3H),1.54(d,J=7.2Hz,3H)
1-093;
8.90(d,J=2.4Hz,1H),8.56(dd,J=4.8,1.2Hz,1H),8.02(s,1H),7.92(ddd,J=8.4,2.4,1.2Hz,1H),7.45-7.25(m,6H),5.60-5.45(m,1H),5.10-4.85(m,1H),4.85-4.65(m,3H),3.81(s,3H),2.93(s,3H),1.79(d,J=7.2Hz,3H)
1-094;
8.90(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.10-7.90(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.35-5.15(m,1H),5.10-4.90(m,1H),4.09(q,J=7.2Hz,1H),3.85-3.65(m,5H),1.93(brs,3H),1.51(d,J=7.2Hz,3H),1.05-0.90(m,2H),0.03(s,9H)
1-095;
8.90-8.80(m,1H),8.60-8.50(m,1H),8.15-7.90(m,4H),7.65-7.30(m,4H),6.10-5.60(m,2H),4.25-4.00(m,1H),3.77(brs,3H),1.95(brs,3H),1.55(d,J=7.2Hz,3H)
1-096;
8.89(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.10-7.95(m,2H),7.43(dd,J=8.4,4.8Hz,1H),5.90-5.55(m,2H),4.25-3.85(m,1H),3.76(s,3H),2.34(t,J=7.2Hz,2H),1.93(brs,3H),1.75-1.60(m,2H),1.53(d,J=7.2Hz,3H),0.94(t,J=7.2Hz,3H)
1-098;
8.96(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.07(s,1H),8.05-7.90(m,1H),7.41(dd,J=8.4,4.8Hz,1H),5.45-5.25(m,1H),5.05-4.80(m,1H),4.68(q,J=7.2Hz,1H),3.81(s,3H),3.85-3.65(m,2H),2.90(s,3H),1.76(d,J=7.2Hz,3H),1.24(t,J=7.2Hz,3H)
1-099;
8.93(d,J=2.7Hz,1H),8.61(dd,J=4.8,1.2Hz,1H),8.16(s,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.43(dd,J=8.4,4.8Hz,1H),4.11(q,J=7.2Hz,1H),3.86(s,3H),3.54(s,3H),1.99(s,3H),1.60-1.50(m,3H)
1-100;
8.90(d,J=2.7Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.17(s,1H),7.98(ddd,J=8.4,2.7,1.2Hz,1H),7.45-7.35(m,1H),6.25-5.90(m,1H),5.65-5.25(m,1H),4.60-4.05(m,3H),3.76(s,3H),1.97(s,3H),1.52(d,J=7.2Hz,3H)
1-102;
8.93(d,J=2.7Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,1H),8.03(s,1H),7.42(dd,J=8.4,4.8Hz,1H),4.21(q.J=7.2Hz,1H),3.97(s,3H),3.83(s,3H),2.18(s,3H),1.65-1.50(m,3H)
1-103;
8.97(d,J=2.4Hz,1H),8.69(s,1H),8.57(brs,1H),8.54(dd,J=4.8,1.2Hz,1H),7.98(ddd,J=8.4,2.4,1.2Hz,1H),7.38(dd,J=8.4,4.8Hz,1H),4.42(q,J=7.2Hz,1H),4.09(s,3H), 2.65-2.50(m,2H),1.62(d,J=7.2Hz,3H), 1.27(t,J=7.2Hz,3H)
1-104;
(異性体比95)8.92(d,J=2.7Hz,1H),8.62(dd,J=4.8,1.2Hz,1H),8.17(s,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.44(dd,J=8.4,4.8Hz,1H),4.72(d,J=17.2Hz,1H),4.54(d,J=17.2Hz,1H), 4.23-3.98(m,1H),3.75(s,3H), 2.41-2.25(m,2H), 1.51(d,J=7.5Hz,3H), 1.14(t,J=7.2Hz,3H)
(異性体比5)8.97(s,1H),8.92(d,J=2.7Hz,1H),8.62(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.44(dd,J=8.4,4.8Hz,1H),4.95-4.85(m,1H),4.63-4.49(m,1H), 4.23-3.98(m,1H),3.75(s,3H), 2.77-2.41(m,2H), 1.42(d,J=7.2Hz,3H), 1.14(t,J=7.2Hz,3H)
1-105(*3);
(異性体比2)9.00-8.80(m,1H),8.65-8.55(m,1H),8.28(brs,1H),8.05-7.95(m,1H),7.55-7.35(m,1H),6.00-5.55(m,2H),4.00-3.60(m,7H),1.92(brs,3H),1.41(d,J=7.2Hz,3H)
(異性体比1)9.00-8.80(m,1H),8.65-8.55(m,1H),8.09(s,1H),8.05-7.95(m,1H),7.55-7.35(m,1H),6.00-5.35(m,2H),4.00-3.60(m,7H),2.15(brs,3H),1.60-1.40(brs,3H)
1-112;
(異性体比50)8.87(d,J=2.4Hz,1H),8.58(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.42(dd,J=8.4,4.8Hz,1H),5.85-5.60(m,2H),4.25-3.60(m,4H),3.40-3.20(m,4H),1.94(brs,3H),1.62(d,J=7.2Hz,3H),1.20-1.00(m,6H)
(異性体比6)8.95(d,J=2.4Hz,1H),8.60-8.50(m,1H),8.24(s,1H),8.05-7.95(m,1H),7.45-7.35(m,1H),5.85-5.60(m,2H),4.25-3.60(m,4H),3.40-3.20(m,4H),1.94(brs,3H),1.62(d,J=7.2Hz,3H),1.20-1.00(m,6H)
1-113;
(異性体比83)8.94(d,J=2.7Hz,1H),8.65-8.55(m,1H),8.10-8.00(m,1H),7.91(s,1H),7.50-7.40(m,1H),6.15-5.95(m,1H),4.10-3.90(m,1H),3.75(s,3H),3.53(s,3H),1.86(brs,3H),1.55-1.20(m,6H)
(異性体比10)9.00-8.90(m,1H),8.65-8.55(m,1H),8.10-8.00(m,1H),7.89(s,1H),7.50-7.40(m,1H),5.55-5.35(m,1H),4.10-3.90(m,1H),3.55(s,3H),3.53(s,3H),2.08(brs,3H),1.55-1.20(m,6H)
1-114;
8.93(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.11(s,1H),8.03(ddd,J=8.1,2.4,1.2Hz,1H),7.43(dd,J=8.1,4.8Hz,1H),5.14-4.98(m,1H),4.70-4.60(m,1H),4.10(q,J=7.2Hz,1H), 3.75(s,3H), 2.26(s,3H),1.93(s,3H),1.51(d,J=7.2Hz,3H)
1-115;
(異性体比83)8.92(d,J=2.4Hz,1H),8.60(d,J=4.5Hz,1H),8.06-7.99(m,1H),7.86(s,1H),7.44(dd,J=8.1,4.5Hz,1H),6.22-6.02(m,1H),4.35-3.55(m,3H),3.74(s,3H), 2.30-1.80(m,3H), 1.68-1.10(m,9H)
(異性体比17)8.92(d,J=2.4Hz,1H),8.60(d,J=4.5Hz,1H),8.06-7.99(m,1H),7.86(s,1H),7.44(dd,J=8.1,4.5Hz,1H),5.62-5.48(m,1H),4.35-3.55(m,3H),3.74(s,3H),2.30-1.80(m,3H), 1.68-1.10(m,9H)
1-116(*3)
9.12(brs,1H),8.99(d,J=2.4Hz,1H),8.62(s,1H),8.50(dd,J=4.8,1.2Hz,1H),7.98(ddd,J=8.4,2.4,1.2Hz,1H),7.36(dd,J=8.4,4.8Hz,1H),4.08(s,3H),4.05(q,J=7.2Hz,1H),2.35(s,3H),2.08(s,3H),1.53(d,J=7.2Hz,3H)
1-118;
8.92(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.11(s,1H),8.10-7.95(m,1H),7.50-7.35(m,1H),5.90-5.70(m,1H),5.65-5.40(m,1H),4.40-4.20(m,3H),3.75(brs,3H),3.65-3.50(m,2H),3.36(s,3H),1.92(brs,3H),1.53(d,J=7.2Hz,3H)
1-119;
8.96(d,J=2.4Hz,1H),8.59(dd,J=4.8,1.2Hz,1H),8.14(s,1H),8.05-7.90(m,1H),7.42(dd,J=8.4,4.8Hz,1H),6.00-5.75(m,1H),5.65-5.35(m,1H),4.80-4.55(m,1H),4.29(t,J=4.5Hz,2H),3.81(s,3H),3.60(t,J=4.5Hz,2H),3.36(s,3H),2.93(s,3H),1.76(d,J=7.2Hz,3H)
1-120;
(異性体比87)9.00-8.95(m,1H),8.61-8.58(m,1H),8.14(s,1H),8.12-8.02(m,1H),7.44(dd,J=8.1,4.8Hz,1H),6.53(s,1H),3.61(s,3H), 3.41(s,3H),3.15(q,J=7.2Hz,1H), 2.10(s,3H), 1.45(d,J=7.2Hz,3H)
(異性体比13)9.00-8.95(m,1H),8.61-8.58(m,1H),8.14(s,1H),8.12-8.02(m,1H),7.44(dd,J=8.1,4.8Hz,1H),6.45(s,1H),3.56(s,3H), 3.43(s,3H),3.24(q,J=7.2Hz,1H), 2.25(s,3H), 1.38(d,J=7.2Hz,3H)
1-122;
(異性体比93)8.98(d,J=2.7Hz,1H),8.69(s,1H),8.64(brs,1H),8.55(dd,J=4.8,1.2Hz,1H),7.98(ddd,J=8.4,2.7,1.2Hz,1H),7.39(dd,J=8.4,4.8Hz,1H),4.07(s,3H),3.82(d,J=10.8Hz,1H),2.58-2.40(m,1H), 2.13(s,3H),1.44(d,J=6.6Hz,3H),0.90(d,J=6.6Hz,3H)
(異性体比7)9.51(brs,1H),8.98(d,J=2.7Hz,1H),8.71(s,1H),8.55(dd,J=4.8,1.2Hz,1H),7.98(ddd,J=8.4,2.7,1.2Hz,1H),7.39(dd,J=8.4,4.8Hz,1H),4.08(s,3H),3.40(d,J=10.5Hz,1H),2.58-2.40(m,1H), 2.09(s,3H),1.44(d,J=6.6Hz,3H),0.90(d,J=6.6Hz,3H)
1-128;
8.97(d,J=2.4Hz,1H),8.57(dd,J=4.8,1.2Hz,1H),8.10-7.95(m,1H),7.90-7.80(m,1H),7.42(dd,J=8.4,4.8Hz,1H),7.30-7.20(m,1H),5.85-5.45(m,2H),4.00-3.80(m,7H),2.25-1.80(m,3H),1.60-1.50(brs,3H)
1-129;
8.98(d,J=2.7Hz,1H),8.65-8.50(m,1H),8.20-7.70(m,2H),7.41(dd,J=8.4,4.8Hz,1H),7.30-7.20(m,1H),5.80-5.40(m,2H),5.00-4.60(m,1H),3.81(s,3H),3.80(s,3H),3.25-2.60(m,3H),1.76(d,J=7.2Hz,3H)
1-132;
(異性体比3)8.91(d,J=2.4Hz,1H),8.60(dd,J=4.8,1.2Hz,1H),8.09(s,1H),8.01(ddd,J=8.4,2.4,1.2Hz,1H),7.43(dd,J=8.4,4.8Hz,1H),5.90-5.35(m,2H),3.90-3.50(m,7H),2.40-2.20(m,1H), 1.87(brs,3H),1.14(d,J=6.0Hz,6H)
(異性体比1)9.00-8.85(m,1H),8.65-8.50(m,1H),8.12(s,1H),8.05-7.90(m,1H),7.43(dd,J=8.4,4.8Hz,1H),5.90-5.35(m,2H),3.90-3.50(m,7H),2.40-2.20(m,1H), 1.87(brs,3H),0.98(d,J=6.0Hz,6H)
1-142;
8.95-8.85(m,1H),8.54(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,1H),7.95(s,1H),7.40(dd,J=8.4,4.8Hz,1H),5.70-5.50(m,2H),4.30-3.90(m,1H),3.75(brs,3H),2.45-2.20(m,5H),2.10(s,3H),1.55-1.45(m,3H),1.20-1.05(m,3H)
1-143;
8.91(d,J=2.4Hz,1H),8.53(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,2H),7.40(dd,J=8.4,4.8Hz,1H),5.85-5.45(m,2H),4.25-4.10(m,1H),3.79(s,3H),3.75(brs,3H),2.40-2.15(m,5H),1.60-1.40(m,3H),1.25-1.00(m,3H)
1-144;
(異性体比5)8.88(d,J=2.4Hz,1H),8.54(dd,J=4.8,1.2Hz,1H),8.20-7.95(m,2H),7.40(dd,J=8.4,4.8Hz,1H),5.30-4.75(m,2H),4.05-3.80(m,4H),3.47(s,3H),2.31(s,3H),1.81(s,3H),1.38(d,J=7.2Hz,3H)
(異性体比1)8.92(d,J=2.4Hz,1H),8.50(dd,J=4.8,1.2Hz,1H),8.20-7.95(m,2H),7.45-7.30(m,1H),5.30-4.75(m,2H),4.05-3.80(m,4H),3.38(s,3H),2.27(s,3H),2.16(s,3H),1.58(d,J=7.2Hz,3H)
1-145;
8.90(d,J=2.7Hz,1H),8.60-8.45(m,2H),8.15-8.00(m,1H),7.38(dd,J=8.4,4.8Hz,1H),4.59(q,J=7.2Hz,1H),4.47(q,J=7.2Hz,1H),4.14(s,3H),4.00(s,3H),2.75-2.55(m,2H),2.46(s,3H),2.12(s,3H),1.69(d,J=7.2Hz,3H),1.59(d,J=7.2Hz,3H),1.28(t,J=7.2Hz,3H)
1-148;
(異性体比2)8.89(d,J=2.7Hz,1H)8.55(dd,J=4.8,1.2Hz,1H),8.05-7.95(m,1H),7.85(s,1H),7.45-7.35(m,1H),4.20-4.00(m,1H),3.78(s,3H),3.29(s,3H),2.57(s,3H),2.31(s,3H),2.30-1.70(m,2H),0.90(t,J=7.2Hz,3H)
(異性体比1)8.96(d,J=2.7Hz,1H)8.50(dd,J=4.8,1.2Hz,1H),8.08(s,1H),8.05-7.95(m,1H),7.45-7.35(m,1H),4.20-4.00(m,1H),3.71(s,3H),3.28(s,3H),2.49(s,3H),2.33(s,3H),2.30-1.70(m,2H),1.03(t,J=7.2Hz,3H)
1-149;
(異性体比25)8.95(d,J=2.7Hz,1H)8.52(dd,J=4.8,1.2Hz,1H),8.02(s,1H),8.05-7.90(m,1H),7.37(dd,J=8.4,4.8Hz,1H),4.57(q,J=5.1Hz,1H),3.73(s,3H),3.29(s,3H),2.81(s,3H),2.33(s,3H),2.30-2.10(m,2H),1.06(t,J=7.2Hz,3H)
(異性体比3)9.00-8.90(m,1H),8.60-8.45(m,1H),8.10-7.90(m,2H),7.45-7.30(m,1H),4.80-4.50(m,1H),4.07(s,3H),3.50(s,3H),3.01(s,3H),2.45-2.10(m,5H),1.15-1.00(m,3H)
1-153;
8.81(d,J=2.7Hz,1H),8.60-8.55(m,3H),7.95-7.85(m,1H),7.33(s,1H),7.45-7.35(m,1H),7.30-7.20(m,2H),5.07(d,J=15.0Hz,1H),4.79(d,J=15.0Hz,1H),4.19(q,J=7.2Hz,1H),3.77(s,3H),2.45-2.30(m,2H),1.56(d,J=7.2Hz,3H),1.16(t,J=7.5Hz,3H)
1-154;
(異性体比8)9.02-8.96(m,1H),8.57(s,1H),8.56-8.46(m,1H),8.30(brs,1H),8.03-7.96(m,1H),7.45-7.35(m,1H),4.45-4.25(m,1H),4.20-4.10(m,3H),2.53(s,3H),2.45-2.15(m,5H),1.20-0.95(m,3H)
(異性体比7)9.76(brs,1H),9.02-8.96(m,1H),8.57(s,1H),8.56-8.46(m,1H),8.03-7.96(m,1H),7.45-7.35(m,1H),4.45-4.25(m,1H),4.20-4.10(m,3H),2.68(s,3H),2.45-2.15(m,5H),1.20-0.95(m,3H)
1-155;
8.98(d,J=2.4Hz,1H),8.53(s,1H),8.51(dd,J=4.8,1.2Hz,1H),8.39(brs,1H),8.00(ddd,J=8.1,2.4,1.2Hz,1H),7.38(dd,J=8.1,4.8Hz,1H),4.89(dd,J=10.5,4.8Hz,1H),4.17(s,3H),3.11(s,3H),2.55-2.40(m,1H),2.38(s,3H),2.36-2.20(m,1H),1.03(t,J=7.5Hz,3H)
1-156;
8.98(d,J=2.4Hz,1H),8.60(s,1H),8.49(dd,J=4.5,1.2Hz,1H),8.37(brs,1H),7.98(ddd,J=8.1,2.4,1.2Hz,1H),7.36(dd,J=8.1,4.5Hz,1H),4.48(dd,J=9.0,6.6Hz,1H),4.10-4.40(m,4H),3.80(dd,J=9.0,6.6Hz,1H),3.37(s,3H),2.38(s,3H),2.22(s,3H)
1-160;
8.89(d,J=2.4Hz,1H),8.53(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.4,2.4,1.2Hz,1H),7.97(s,1H),7.39(dd,J=8.4,4.8Hz,1H),5.80-5.20(m,2H),4.00-3.60(m,4H),2.45-2.25(m,3H),2.20-1.95(m,5H),1.80(brs,3H),1.03(t,J=7.5Hz,3H)
1-162;
8.97(d,J=2.7Hz,1H),8.54(s,1H),8.49(dd,J=4.8,1.8Hz,1H),8.29(brs,1H),7.98(ddd,J=8.7,2.7,1.8Hz,1H),7.36(dd,J=8.7,4.8Hz,1H),5.23(dd,J=8.1,5.4Hz,1H),4.42(dd,J=10.2,8.1Hz,1H),4.17(s,3H),3.96(dd,J=10.2,5.4Hz,1H),3.42(s,3H),3.13(s,3H),2.37(s,3H)
1-163;
8.98(d,J=2.4Hz,1H),8.43(dd,J=4.8,0.9Hz,1H),8.03-7.96(m,1H),7.92(s,1H),7.39(dd,J=8.1,4.8Hz,1H),5.18(d,J=10.2Hz,1H),5.00(d,J=10.2Hz,1H),4.12(q,J=6.9Hz,2H),3.85-3.75(m,1H),3.74(s,3H),2.34(s,3H), 1.84(s,3H),1.47(d,J=7.5Hz,3H),1.25(t,J=6.9Hz,3H)
1-164;
8.89(d,J=2.1Hz,1H),8.52(dd,J=4.8,1.2Hz,1H),8.02-7.90(m,2H),7.38(dd,J=8.1,4.8Hz,1H),5.75-5.40(m,2H),4.20-3.60(m,9H),3.36(s,3H),3.32(s,3H),2.04(s,3H)
1-165;
9.00-8.90(m,1H),8.60-8.50(m,1H),8.10-7.85(m,2H),7.45-7.35(m,1H),5.80-5.40(m,2H),4.60-4.30(m,1H),4.10-3.70(m,8H),3.50-3.30(m,3H),2.80-2.50(m,3H),2.40-2.20(m,3H)
1-166;
8.94(d,J=2.1Hz,1H),8.53(dd,J=4.8,1.5Hz,1H),8.02-7.90(m,2H),7.38(dd,J=8.1,4.8Hz,1H),5.80-5.40(m,2H),5.00-4.80(m,1H),4.28(dd,J=10.2,9.3Hz,1H),3.89(dd,J=10.2,3.6Hz,1H),3.80-3.70(m,6H),3.41(s,3H),3.03(s,3H),2.32(s,3H)
1-167;
(異性体比3)8.90(d,J=1.8Hz,1H),8.55(dd,J=4.8,1.2Hz,1H),8.10-7.80(m,2H),7.45-7.35(m,1H),5.80-5.40(m,2H),4.20-3.70(m,7H),2.70-2.40(m,3H),2.40-2.10(m,4H),2.00-1.70(m,1H),1.20-0.80(m,3H)
(異性体比2)8.94(d,J=2.1Hz,1H),8.51(dd,J=4.5,1.5Hz,1H),8.10-7.80(m,2H),7.45-7.35(m,1H),5.80-5.40(m,2H),4.20-3.70(m,7H),2.70-2.40(m,3H),2.40-2.10(m,4H),2.00-1.70(m,1H),1.20-0.80(m,3H)
1-168;
8.94(d,J=2.4Hz,1H),8.53(dd,J=4.8,1.2Hz,1H),8.02(s,1H),8.00-7.90(m,1H),7.38(dd,J=7.8,4.8Hz,1H),5.80-5.40(m,2H),4.70-4.50(m,1H),4.00-3.60(m,6H),3.10-2.70(m,3H),2.50-2.10(m,5H),1.06(t,J=7.5Hz,3H)
1-170;
8.94(d,J=2.1Hz,1H),8.53(dd,J=4.8,1.5Hz,1H),8.04-7.90(m,2H),7.38(dd,J=8.7,4.8Hz,1H),5.75-5.55(m,2H),4.70-4.50(m,1H),4.20-3.70(m,3H),3.10-2.70(m,3H),2.50-2.20(m,8H),1.07(t,J=6.6Hz,3H)
1-171;
8.93(d,J=2.1Hz,1H),8.56(d,J=4.8Hz,1H),8.12(s,1H),8.05-7.95(m,1H),7.42(dd,J=8.4,4.8Hz,1H),4.64(d,J=16.8Hz,1H),4.41(d,J=16.8Hz,1H),3.88(t,J=7.8Hz,1H),3.73(s,3H),2.39(s,3H),2.10-1.90(m,1H),1.90-1.70(m,4H),1.02(t,J=7.2Hz,3H)
1-172;
9.00-8.86(m,1H),8.65-8.45(m,1H),8.10-7.85(m,2H),7.45-7.35(m,1H),5.24-4.90(m,2H),4.20-3.50(m,6H),2.85-2.45(m,3H),2.35-2.20(m,3H), 1.80-1.45(m,3H),1.30-1.20(m,3H)
1-173;
(異性体比58)9.00-8.90(m,1H),8.60-8.50(m,1H),8.05-7.90(m,2H),7.46-7.34(m,1H),5.25(d,J=9.6Hz,1H),4.95(d,J=9.6Hz,1H),4.68(q,J=7.2Hz,1H),3.95-3.65(m,5H), 2.77(brs,3H),2.40-2.25(m,3H),1.82-1.40(m,3H),1.30-1.15(m,3H)
(異性体比27)9.00-8.90(m,1H),8.60-8.50(m,1H),8.05-7.90(m,2H),7.46-7.34(m,1H),5.25(d,J=9.6Hz,1H),4.95(d,J=9.6Hz,1H),4.68(q,J=7.2Hz,1H),3.95-3.65(m,5H), 2.95(brs,3H),2.40-2.25(m,3H),1.82-1.40(m,3H),1.30-1.15(m,3H)
(異性体比15)9.00-8.90(m,1H),8.60-8.50(m,1H),8.05-7.90(m,2H),7.46-7.34(m,1H),5.25(d,J=9.6Hz,1H),4.95(d,J=9.6Hz,1H),4.68(q,J=7.2Hz,1H),3.95-3.65(m,5H), 3.07(brs,3H),2.40-2.25(m,3H),1.82-1.40(m,3H),1.30-1.15(m,3H)
1-174;
8.93(d,J=2.7Hz,1H),8.60-8.50(m,1H),8.11(s,1H),8.10-7.90(m,1H),7.41(dd,J=8.4,4.8Hz,1H),4.62(d,J=16.5Hz,1H),4.54(d,J=16.5Hz,1H),4.13(q,J=7.2Hz,1H),3.75(s,3H),2.38(s,3H),1.83(s,3H),1.49(d,J=7.2Hz,3H)
1-175;
(異性体比5)9.00-8.85(m,1H),8.65-8.55(m,1H),8.04(s,1H),8.05-7.95(m,1H),7.42(dd,J=8.4,4.8Hz,1H),4.58(s,2H),4.25-4.00(m,1H),3.79(s,3H),2.54(s,3H),2.35(s,3H),1.50(d,J=7.2Hz,3H)
(異性体比3)9.00-8.85(m,1H),8.60-8.50(m,1H),8.16(s,1H),8.00-7.90(m,1H),7.40-7.30(m,1H),4.67(d,J=17.1Hz,1H),4.46(d,J=17.1Hz,1H),4.25-4.00(m,1H),3.76(s,3H),2.52(s,3H),2.38(s,3H),1.52(d,J=7.2Hz,3H)
1-176;
8.97(d,J=2.4Hz,1H),8.55(dd,J=4.8,1.5Hz,1H),8.14(s,1H),8.05-7.95(m,1H),7.39(dd,J=8.4,4.8Hz,1H),4.66(q,J=7.2Hz,1H),4.58(d,J=17.1Hz,1H),4.51(d,J=17.1Hz,1H),3.81(s,3H),2.85(s,3H),2.37(s,3H),1.75(d,J=7.2Hz,3H)
1-177;
9.05-8.80(m,1H),8.70-8.45(m,1H),8.25-7.90(m,2H),7.55-7.30(m,1H),4.75-4.35(m,2H),4.20-4.00(m,1H),3.85-3.70(m,3H),2.60-2.35(m,6H),2.35-1.70(m,2H),1.10―0.90(m,3H)
1-178;
8.97(d,J=2.7Hz,1H),8.55(dd,J=4.8,1.2Hz,1H),8.14(s,1H),8.00-7.90(m,1H),7.38(dd,J=8.4,4.8Hz,1H),4.65-4.45(m,3H),3.78(s,3H),2.83(s,3H),2.38(s,3H),2.30-2.10(m,2H),1.06(t,J=7.2Hz,3H)
1-179;
(異性体比10)8.95-8.85(m,1H),8.54(dd,J=4.8,1.5Hz,1H),8.05-7.90(m,2H),7.39(dd,J=8.4,4.8Hz,1H),5.75-5.25(m,2H),4.20-3.80(m,1H),3.74(brs,3H),2.40-2.00(m,6H),1.83(brs,3H),1.55-1.35(m,3H)
(異性体比1)9.00-8.90(m,1H),8.55-8.45(m,1H),8.05-7.90(m,2H),7.45-7.30(m,1H),5.75-5.25(m,2H),4.20-3.80(m,4H),2.40-1.80(m,9H),1.55-1.35(m,3H)
1-180;
9.00-8.90(m,1H),8.60-8.45(m,1H),8.10-7.90(m,2H),7.45-7.35(m,1H),5.70-5.15(m,2H),4.25-4.00(m,1H),3.85-3.70(m,3H),2.70-2.50(m,3H),2.40―2.20(m,3H),2.11(brs,3H),1.85-1.50(m,3H)
1-181;
8.96(d,J=2.4Hz,1H),8.54(dd,J=4.8,1.2Hz,1H),8.05-7.90(m,2H),7.39(dd,J=8.4,4.8Hz,1H),5.75-5.35(m,2H),4.66(q,J=7.2Hz,1H),3.80(s,3H),2.81(s,3H),2.33(s,3H),2.11(s,3H),1.75(d,J=7.2Hz,3H)
1-182;
9.00-8.85(m,1H),8.65-8.45(m,1H),8.10-7.85(m,2H),7.45-7.30(m,1H),5.80-5.40(m,2H),4.25-4.00(m,1H),3.80-3.65(m,6H),2.70-2.45(m,3H),2.40-2.20(m,3H),1.52(d,J=7.2Hz,3H)
1-183;
8.91(d,J=2.4Hz,1H),8.56(dd,J=4.8,1.5Hz,1H),8.09(s,1H),7.96(ddd,J=8.4,2.4,1.5Hz,1H),7.40(dd,J=8.4,4.8Hz,1H),4.64(d,J=16.8Hz,1H),4.51(d,J=16.8Hz,1H),4.12(q,J=7.2Hz,1H),4.10-3.90(m,2H),2.37(s,3H),1.86(s,3H),1.50(d,J=7.2Hz,3H),1.09(t,J=7.2Hz,3H)
1-184;
8.93(d,J=2.4Hz,1H),8.55(dd,J=4.8,1.5Hz,1H),8.08(s,1H),7.97(ddd,J=8.4,2.4,1.5Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),4.59(s,2H),4.02(t,J=4.2Hz,2H),3.58(s,2H),3.32(t,J=4.2Hz,2H),3.15(s,3H),2.37(s,3H),1.87(s,3H)
1-185;
8.89(d,J=2.7Hz,1H),8.55-8.50(m,1H),8.10-7.85(m,2H),7.45-7.35(m,1H),5.19(d,J=9.9Hz,1H),4.98(d,J=9.9Hz,1H),3.95-3.65(m,6H),2.45-2.30(m,3H),2.20-1.90(m,2H),1.80(s,3H),1.25(m,3H),1.03(t,J=7.2Hz,3H)
1-187;
8.90-8.85(m,1H),8.60-8.45(m,1H),8.10-7.90(m,2H),7.50-7.35(m,1H),5.30-4.90(m,2H),4.20-4.00(m,2H),3.80-3.60(m,4H),2.70-2.20(m,6H),2.00-1.70(m,2H),1.30-1.20(m,3H),1.20-0.90(m,3H)
1-189;
9.00-8.85(m,1H),8.65-8.45(m,1H),8.10-7.95(m,2H),7.50-7.35(m,1H),5.30-4.80(m,2H),4.20-4.00(m,1H),3.55-3.40(m,3H),2.75-2.20(m,9H),2.00-1.70(m,2H),1.15-0.90(m,3H)
1-190;
(異性体比2)9.00-8.90(m,1H),8.55-8.50(m,1H),8.05-7.90(m,2H),7.45-7.35(m,1H),5.20-5.10(m,1H),5.00-4.85(m,1H),4.59(dd,J=11.1,5.4Hz,1H),3.77(s,3H),3.50(s,3H),2.76(s,3H),2.40-2.10(m,2H),2.33(s,3H),1.07(t,J=7.5Hz,3H)
(異性体比1)9.00-8.90(m,1H),8.55-8.50(m,1H),8.05-7.90(m,2H),7.45-7.35(m,1H),5.20-5.10(m,1H),5.00-4.85(m,1H),4.59(dd,J=11.1,5.4Hz,1H),3.88(brs,3H),3.48(s,3H),2.88(s,3H),2.40-2.10(m,2H),2.32(s,3H),1.20-0.90(m,3H)
1-191;
(異性体比51)9.02-8.92(m,1H),8.60-8.50(m,1H),8.40-7.94(m,2H),7.45-7.35(m,1H),5.30-4.60(m,3H),3.87(brs,3H),3.47(s,3H),2.94(s,3H), 2.31(s,3H),1.82-1.42(m,3H)
(異性体比25)9.02-8.92(m,1H),8.60-8.50(m,1H),8.40-7.94(m,2H),7.45-7.35(m,1H),5.30-4.60(m,3H),4.05(s,3H),3.38(s,3H),2.78(s,3H), 2.33(s,3H),1.82-1.42(m,3H)
(異性体比24)9.02-8.92(m,1H),8.60-8.50(m,1H),8.40-7.94(m,2H),7.45-7.35(m,1H),5.30-4.60(m,3H),3.81(s,3H),3.50(s,3H),3.06(s,3H), 2.26(s,3H),1.82-1.42(m,3H)
1-192;
8.89(d,J=2.4Hz,1H),8.55-8.50(m,1H),8.05-7.85(m,2H),7.45-7.35(m,1H),5.15(d,J=10.5Hz,1H),4.90(d,J=10.5Hz,1H),4.10-3.80(m,1H),3.73(s,3H),3.50(s,3H),2.36(s,3H),2.20-1.90(m,2H),1.81(s,3H),1.03(t,J=7.2Hz,3H)
1-194;
9.10-8.80(m,1H),8.65-8.55(m,1H),8.35-8.10(m,1H),8.10-7.95(m,1H),7.50-7.35(m,1H),4.85-4.60(m,2H),3.80-3.60(m,1H),3.36(s,3H),1.90(s,3H),1.50-1.30(m,3H)
1-195;
9.05-8.80(m,1H),8.70-8.45(m,1H),8.25-7.90(m,2H),7.55-7.30(m,1H),4.75-4.35(m,2H),4.20-4.00(m,1H),3.85-3.70(m,3H),2.60-2.35(m,6H),2.35-1.70(m,2H),1.10―0.90(m,3H)
1-196;
9.00-8.80(m,1H),8.65-8.55(m,1H),8.30-7.90(m,2H),7.50-7.40(m,1H),3.85-3.30(m,4H),2.30-2.20(m,3H),2.20-1.35(m,6H)
1-197;
8.98(d,J=2.7Hz,1H),8.59(s,1H),8.49(dd,J=4.8,1.5Hz,1H),8.32(brs,1H),7.97(ddd,J=8.7,2.7.1.5Hz,1H),7.36(dd,J=8.7,4.8Hz,1H),3.96(s,3H),2.35(s,3H),2.14(s,3H),1.55(s,6H)
1-198;
9.00-8.85(m,1H),8.65-8.40(m,2H),8.10-7.90(m,1H),7.50-7.30(m,1H),5.35(m,2H),3.55-3.30(m,7H),1.90-1.75(m,3H),1.65-1.30(m,3H)
1-200;
8.97(d,J=2.7Hz,1H),8.77(brs,1H),8.58(s,1H),8.49(dd,J=4.8,1.5Hz,1H),7.98(ddd,J=7.8,2.7.1.5Hz,1H),7.36(dd,J=7.8,4.8Hz,1H),4.03(s,3H),3.08(s,3H),2.35(s,3H),1.74(s,6H)
1-203;
8.98(d,J=2.7Hz,1H),8.54(s,1H),8.50(dd,J=4.8,1.5Hz,1H),7.98(ddd,J=8.1,2.7,1.5Hz,1H),7.93(s,1H),7.78(d,J=8.4Hz,2H),7.37(dd,J=8.1,4.8Hz,1H),7.29(d,J=8.4Hz,2H),5.59(dd,J=8.7,6.0Hz,1H),4.06(s,3H),2.41(s,3H),2.35(s,3H),2.25-2.10(m,1H),2.00-1.80(m,1H),0.87(t,J=7.2Hz,3H)
1-205;
9.01-8.97(m,1H),8.72-8.66(m,1H),8.63(s,1H),8.52-8.48(m,1H),8.31(brs,1H),8.02-7.95(m,1H),7.69-7.62(m,1H),7.41-7.33(m,1H),7.30-7.23(m,1H),5.75(t,J=7.8Hz,1H),4.13(s,3H),2.37(s,3H),2.22-2.00(m,2H),1.03(t,J=7.2Hz,3H)
1-207;
(異性体比2)8.96(d,J=2.4Hz,1H),8.59(s,1H),8.56-8.44(m,2H),8.20-7.92(m,1H),7.71-7.65(m,1H),7.71-7.65(m,5H),4.09(s,3H),2.43(s,3H)
(異性体比1)8.99(d,J=1.8Hz,1H),8.67(s,1H),8.56-8.44(m,1H),8.20-7.92(m,2H),7.71-7.65(m,6H),4.11(s,3H),2.36(s,3H)
1-208;
9.00(brs,1H),8.67(brs,1H),8.07(s,1H),8.02(d,J=8.7Hz,1H),7.45(brs,1H),3.91(s,3H),3.71(q,J=6.9Hz,1H),2.10(s,3H),2.06(s,3H),1.48(d,J=6.9Hz,3H)
1-212;
8.98(d,J=3.0Hz,1H),8.70-8.60(m,1H),8.54(s,1H),8.45(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.4,3.0,1.2Hz,1H),7.86(t,J=4.5Hz,1H),7.35(dd,J=8.4,4.8Hz,1H),4.75-4.60(m,1H),3.50-3.30(m,2H),2.37(s,3H),2.15-1.70(m,5H),1.27(t,J=7.2Hz,3H),0.99(t,J=7.2Hz,3H)
1-218;
9.82(s,1H),9.00(d,J=2.7Hz,1H),8.60(s,1H),8.50(dd,J=4.8,1.2Hz,1H),8.01(ddd,J=8.4,2.7,1.2Hz,1H),7.40-6.75(m,7H),3.80-3.65(m,1H),2.40(s,3H),2.14(s,3H),2.10-1.85(m,2H),1.07(t,J=7.2Hz,3H)
1-222;
8.98(d,J=2.4Hz,1H),8.83(brs,1H),8.61(s,1H),8.53(dd,J=4.8,1.0Hz,1H),8.07(t,J=4.5Hz,1H),7.99(ddd,J=8.4,2.4,1.0Hz,1H),7.38(dd,J=8.4,4.8Hz,1H),6.05-5.85(m,1H),5.35-5.20(m,2H),4.78(q,J=7.5Hz,1H),4.10-4.00(m,2H),2.02(s,3H),1.47(d,J=7.5Hz,3H)
1-225;
(異性体比3)8.97(d,J=2.4Hz,1H),8.59(s,1H),8.47(dd,J=4.8,1.2Hz,1H),8.37(brs,1H),7.99-7.95(m,1H),7.35(dd,J=8.1,4,8Hz,1H),5.90-5.68(m,1H),5.20-5.04(m,2H),4.06(s,3H),3.16(d,J=8.1Hz,2H),2.72-2.51(m,1H),2.37(s,3H),2.14-1.77(m,2H),0.97(t,J=8.4Hz,3H)
(異性体比1)8.97(d,J=2.4Hz,1H),8.59(s,1H),8.47(dd,J=4.8,1.2Hz,1H),8.39(brs,1H),7.99-7.95(m,1H),7.35(dd,J=8.1,4,8Hz,1H),5.90-5.68(m,1H),5.20-5.04(m,2H),4.06(s,3H),3.11(d,J=8.1Hz,2H),2.72-2.51(m,1H),2.37(s,3H),2.14-1.77(m,2H),1.07-0.95(m,3H)
1-231;
10.3(brs,1H),8.98(d,J=2.4Hz,1H),8.58(s,1H),8.52(dd,J=4.8,1.2Hz,1H),8.05-7.90(m,1H),7.45-7.20(m,7H),5.26(s,2H),4.01(q,J=7.2Hz,1H),2.39(s,3H),2.20(s,3H),1.58(d,J=7.2Hz,3H)
1-232:
(異性体比7)9.76(s,1H),8.99(d,J=2.4Hz,1H),8.73(s,1H),8.56(dd,J=4.8,1.5Hz,1H),8.03-7.95(m,1H),7.46-7.36(m,1H),4.45-4.25(m,2H),4.16(q,J=7.2Hz,1H),2.09(s,3H),1.90-1.70(m,2H),1.55(d,J=7.2Hz,3H),1.50-1.25(m,6H),1.00-0.82(m,3H)
(異性体比3)9.76(s,1H),8.99(d,J=2.4Hz,1H),8.66(s,1H),8.56(dd,J=4.8,1.5Hz,1H),8.03-7.95(m,1H),7.46-7.36(m,1H),4.45-4.25(m,2H),4.16(q,J=7.2Hz,1H),2.16(s,3H),1.90-1.70(m,2H),1.66(d,J=7.2Hz,3H),1.50-1.25(m,6H),1.00-0.82(m,3H)
1-233;
(異性体比2)9.92(s,1H),9.20-8.95(m,1H),8.75(s,1H),8.60-8.50(m,1H),8.06-7.94(m,1H),7.46-7.34(m,1H),4.22-4.06(m,3H),2.09(s,3H),1.55(d,J=7.2Hz,3H),1.36-1.10(m,1H),0.73-0.60(m,2H),0.45-0.34(m,2H)
(異性体比1)9.92(s,1H),9.20-8.95(m,1H),8.70(s,1H),8.60-8.50(m,1H),8.06-7.94(m,1H),7.46-7.34(m,1H),4.50-4.40(m,1H),4.22-4.06(m,2H),2.18(s,3H),1.68(d,J=7.2Hz,3H),1.36-1.10(m,1H),0.73-0.60(m,2H),0.45-0.34(m,2H)
1-237;
11.3(brs,1H),10.0(brs,1H),9.01(d,J=2.7Hz,1H),8.60(s,1H),8.50(dd,J=4.5,1.2Hz,1H),8.05-7.95(m,1H),7.40(dd,J=8.4,4.5Hz,1H),6.06(t,J=6.0Hz,1H),3.83(q,H=7.2Hz,1H),3.45-3.35(m,2H),2.39(s,3H),2.18(s,3H),1.61(d,J=7.2Hz,3H),1.21(t,J=7.2Hz,3H)
1-238;
10.7(brs,1H),9.72(brs,1H),8.99(d,J=2.7Hz,1H),8.64(s,1H),8.54(dd,J=4.8,1.2Hz,1H),8.04(ddd,J=8.4,2.7,1.2Hz,1H),7.42(dd,J=8.4,4.8Hz,1H),4.25(q,J=7.2Hz,1H),3.70-3.50(m,1H),2.05-1.00(m,16H)
1-240;
(異性体比7)8.98(brs,1H),8.64(s,1H),8.60-8.50(m,2H),8.04-7.96(m,1H),7.41(dd,J=8.4,5.1Hz,1H),5.85-5.60(m,1H),5.25-5.10(m,2H),5.01(dd,J=9.9,5.1Hz,1H),4.19(s,3H),3.34-3.16(m,1H),3.10(s,3H),3.05-2.93(m,1H)
(異性体比3)9.65(brs,1H),8.98(brs,1H),8.67(s,1H),8.60-8.50(m,1H),8.04-7.96(m,1H),7.41(dd,J=8.4,5.1Hz,1H),5.85-5.60(m,1H),5.25-5.10(m,2H),4.88(dd,J=10.5,4.8Hz,1H),4.25(s,3H),3.34-3.16(m,1H),3.05-2.93(m,1H),2.98(s,3H)
1-242;
(異性体比2)8.99(s,1H),8.70(s,1H),8.64-8.52(m,2H),8.05-7.95(m,1H),7.48-7.36(m,1H),4.87(d,J=2.7Hz,2H),4.41(q,J=7.2Hz,1H),2.59(t,J=2.7Hz,1H),2.18(s,3H),1.67(d,J=7.2Hz,3H)
(異性体比1)9.20(s,1H),8.99(s,1H),8.72(s,1H),8.64-8.52(m,1H),8.10-8.05(m,1H),7.48-7.36(m,1H),4.58(d,J=2.7Hz,2H),4.07(q,J=7.2Hz,1H),2.25(t,J=2.7Hz,1H),2.12(s,3H),1.55(d,J=7.2Hz,3H)
1-245;
8.99(d,J=2.7Hz,1H),8.62(s,1H),8.49(dd,J=4.8,1.2Hz,1H),8.45(brs,1H),8.04-7.90(m,1H),7.36(dd,J=8.1,4,8Hz,1H),4.26-4.14(m,1H),4.08(s,3H),2.74-2.58(m,1H),2.39(s,3H),2.20-1.88(m,4H),1.85-1.67(m,2H),1.66-1.55(m,1H),1.42-1.18(m,5H),0.99(t,J=7.5Hz,3H)
1-247;
(異性体比6)12.0(brs,1H),9.41(brs,1H),8.96(d,J=2.4Hz,1H),8.52(s,1H),8.47(dd,J=4.8,1.2Hz,1H),8.05-7.30(m,7H),4.98(q,J=7.2Hz,1H),2.42(s,3H),2.16(s,3H),1.58(d,J=7.2Hz,3H)
(異性体比1)12.0(brs,1H),10.5(brs,1H),9.00(d,J=2.4Hz,1H),8.63(s,1H),8.55-8.45(m,1H),8.05-7.30(m,7H),4.20-4.00(m,1H),2.25(s,3H),2.11(s,3H),1.65(d,J=7.2Hz,3H)
1-248;
(異性体比5)9.05-8.95(m,1H),8.74(brs,1H),8.70-8.60(m,1H),8.55-8.40(m,1H),8.10-7.85(m,1H),7.45-7.30(m,1H),4.13(q,J=7.2Hz,1H),3.70-3.25(m,4H),2.36(s,3H),2.16(s,3H),2.00-1.80(m,4H),1.77(d,J=7.2Hz,3H)
(異性体比2)10.1(brs,1H),9.05-8.95(m,1H),8.70-8.60(m,1H),8.55-8.40(m,1H),8.10-7.85(m,1H),7.45-7.30(m,1H),3.91(q,J=7.2Hz,1H),3.55-3.10(m,4H),2.42(s,3H),2.11(s,3H),2.00-1.80(m,4H),1.51(d,J=7.2Hz,3H)
1-249;
(異性体比10)12.2(brs,1H),10.2(brs,1H),9.05-8.95(m,1H),8.65-8.45(m,2H),8.10-7.95(m,1H),7.50-7.35(m,1H),4.90-3.80(m,1H),3.80-3.45(m,2H),2.40-2.10(m,6H),1.65-1.50(m,3H)
(異性体比9)11.1(brs,1H),9.05-8.95(m,1H),8.65-8.45(m,3H),8.10-7.95(m,1H),7.50-7.35(m,1H),4.90-3.80(m,1H),3.80-3.45(m,2H),2.40-2.10(m,6H),1.65-1.50(m,3H)
1-250;
12.3(brs,1H),9.89(brs,1H),9.05-8.95(m,1H),8.90-8.80(m,2H),8.55-8.45(m,1H),8.30-8.15(m,1H),8.05-7.90(m,1H),7.70-7.55(m,1H),7.40-7.25(m,1H),6.95-6.80(m,1H),3.95(q,J=7.2Hz,1H),2.40(s,3H),2.17(s,3H),1.66(d,J=7.2Hz,3H)
1-253;
8.96(d,J=2.4Hz,1H),8.60(brs,1H),8.55-8.45(m,2H),8.00-7.90(m,1H),7.40-7.30(m,1H),4.19(s,3H),2.92(q,J=7.2Hz,2H),2.36(s,3H),1.16(t,J=7.2Hz,3H)
1-255;
9.00-8.90(m,1H),8.57(s,1H),8.50-8.40(m,1H),8.20-7.90(m,2H),7.40-7.25(m,1H),3.98(s,3H),3.91(s,3H),2.60-2.45(m,2H),2.31(s,3H),1.02(t,J=7.5Hz,3H)
1-256;
8.99(d,J=2.4Hz,1H),8.59(s,1H),8.51(dd,J=4.8,1.2Hz,1H),8.35-8.20(m,1H),8.05-7.95(m,1H),7.44-7.34(m,1H),4.91(s,2H),4.37(q,J=7.5Hz,1H),2.40(s,3H),2.20(s,3H),1.68(d,J=7.5Hz,3H)
1-257;
(異性体比7)9.50-9.30(m,1H),9.01-8.88(m,1H),8.65(s,1H),8.50(dd,J=4.8,1.5Hz,1H),8.10-7.85(m,1H),7.41-7.32(m,1H),4.48-4.38(m,2H),4.20-4.10(m,1H),3.80-3.64(m,2H),3.42(s,3H),2.38(s,3H),2.10(s,3H),1.55(d,J=7.2Hz,3H)
(異性体比3)9.50-9.30(m,1H),9.01-8.88(m,1H),8.61(s,1H),8.50(dd,J=4.8,1.5Hz,1H),8.10-7.85(m,1H),7.41-7.32(m,1H),4.48-4.38(m,2H),4.20-4.10(m,1H),3.80-3.64(m,2H),3.42(s,3H),2.38(s,3H),2.18(s,3H),1.66(d,J=7.5Hz,3H)
1-258;
(異性体比5)11.8(brs,1H),10.0(brs,1H),9.05-8.90(m,1H),8.59(s,1H),8.55-8.45(m,1H),8.10-7.95(m,1H),7.50-7.30(m,1H),3.84(q,J=7.2Hz,1H),2.39(s,3H),2.17(s,3H),2.05(d,J=7.2Hz,2H),1.60(d,J=7.2Hz,3H),1.20-1.00(m,1H),0.80-0.50(m,2H),0.35-0.15(m,2H)
(異性体比2)10.4(brs,1H),9.05-8.90(m,1H),8.60-8.40(m,3H),8.10-7.95(m,1H),7.50-7.30(m,1H),4.80(q,J=7.2Hz,1H),2.41(s,3H),2.36(d,J=9.6Hz,2H),2.23(s,3H),1.53(d,J=7.2Hz,3H),1.20-1.00(m,1H),0.80-0.50(m,2H),0.35-0.15(m,2H)
1-261;
(異性体比3)11.8(brs,1H),10.0(brs,1H),9.05-8.90(m,1H),8.65-8.45(m,2H),8.10-7.90(m,1H),7.45-7.25(m,1H),3.84(q,J=7.2Hz,1H),3.70-3.40(m,2H),2.45-2.20(m,9H),1.61(d,J=7.2Hz,3H)
(異性体比1)10.4(brs,1H),9.05-8.90(m,1H),8.65-8.45(m,3H),8.10-7.90(m,1H),7.45-7.25(m,1H),4.81(q,J=7.2Hz,1H),3.70-3.40(m,2H),2.45-2.20(m,9H),1.53(d,J=7.2Hz,3H)
1-264;
(異性体比3)8.99(s,1H),8.69(s,1H),8.60(s,1H),8.58-8.52(m,1H),8.01-7.98(m,1H),7.45-7.36(m,1H),6.14-5.97(m,1H),5.45-5.33(m,2H),4.84-4.74(m,2H),4.41(q,J=7.5Hz,1H),2.17(s,3H),1.67(d,J=7.5Hz,3H)
(異性体比2)9.60(s,1H),8.99(s,1H),8.72(s,1H),8.58-8.52(m,1H),8.01-7.98(m,1H),7.45-7.36(m,1H),6.14-5.97(m,1H),5.45-5.33(m,2H),4.84-4.74(m,2H),4.13(q,J=7.5Hz,1H),2.09(s,3H),1.54(d,J=7.5Hz,3H)
1-265;
(異性体比7)9.47(s,1H),9.03-8.95(m,1H),8.73(s,1H),8.56(dd,J=4.8,1.2Hz,1H),8.06-7.94(m,1H),7.46-7.36(m,1H),4.88-4.70(m,2H),3.93(q,J=7.2Hz,1H),3.85(s,3H),2.07(s,3H),1.55(d,J=7.2Hz,3H)
(異性体比3)9.03-8.95(m,1H),8.69(s,1H),8.56(dd,J=4.8,1.2Hz,1H),8.47(s,1H),8.06-7.94(m,1H),7.46-7.36(m,1H),4.57-4.41(m,2H),4.29(q,J=7.2Hz,1H),3.83(s,3H),1.97(s,3H),1.50(d,J=7.2Hz,3H)
1-266;
(異性体比3)9.43(d,J=5.1Hz,1H),8.99(s,1H),8.66(d,J=1.5Hz,1H),8.60-8.48(m,1H),8.06-7.94(m,1H),7.40(dd,J=8.1,4.8Hz,1H),4.44-3.96(m,4H),2.65-2.44(m,1H),2.12(s,3H),1.65(dd,J=7.2,1.8Hz,3H),1.34-1.20(m,3H)
(異性体比2)8.99(s,1H),8.71(s,1H),8.60-8.48(m,2H),8.06-7.94(m,1H),7.40(dd,J=8.1,4.8Hz,1H),4.44-3.96(m,4H),2.86-2.65(m,1H),2.20(d,J=1.5Hz,3H),1.54(dd,J=7.2,3.0Hz,3H),1.34-1.20(m,3H)
1-267;
(異性体比4)10.80(s,1H),9.10-8.90(m,1H),8.74(s,1H),8.59-8.49(m,1H),8.06-7.92(m,1H),7.50-7.30(m,1H),4.99-4.74(m,2H),3.89(q,J=7.2Hz,1H),3.81-3.56(m,6H),3.48-3.32(m,2H),2.07(s,3H),1.57(d,J=7.2Hz,3H)
(異性体比1)9.10-8.90(m,1H),8.68(s,1H),8.59-8.49(m,1H),8.06-7.92(m,1H),7.50-7.30(m,1H),4.99-4.74(m,2H),4.44(q,J=7.2Hz,1H),3.81-3.56(m,6H),3.56-3.48(m,2H),2.23(s,3H),1.69(d,J=7.2Hz,3H)(NHのプロトンピークは観測されなかった)
1-268;
(異性体比1)9.05-8.93(m,1H),8.69(s,1H),8.60(s,1H),8.64-8.48(m,1H),8.08-7.93(m,1H),7.55-7.30(m,1H),4.45-4.10(m,3H),2.16(s,3H),1.91-1.68(m,3H),1.65(d,J=7.2Hz,3H),1.47-1.22(m,7H),0.97-0.83(m,3H)
(異性体比1)9.76(s,1H),9.05-8.93(m,1H),8.74(s,1H),8.64-8.48(m,1H),8.08-7.93(m,1H),7.55-7.30(m,1H),4.45-4.10(m,3H),2.09(s,3H),1.91-1.68(m,3H),1.55(d,J=7.2Hz,3H),1.47-1.22(m,7H),0.97-0.83(m,3H)
1-270;
9.55 and 8.52(s,1H),9.28(d,J=2.4Hz,1H),8.79 and 8.74(s,1H),8.67-8.56(m,1H),8.56-8.40(m,1H),7.96-7.85(m,1H),4.50-3.65(m,3H),2.38 and 2.36(s,3H),2.17 and 2.10(s,3H),1.65 and 1.54(d,J=7.2Hz,3H),1.48-1.34(m,3H)
1-271;
(異性体比3)9.31(d,J=2.4Hz,1H),8.76(s,1H),8.69-8.59(m,1H),8.59-8.51(m,1H),8.48(s,1H),8.06-7.89(m,1H),4.33-4.20(m,2H),3.73(q,J=7.2Hz,1H),2.38(s,3H),2.17(s,3H),1.95-1.68(m,2H),1.65(d,J=7.2Hz,3H),1.09-0.98(m,3H)
(異性体比2)9.55(s,1H),9.31(d,J=2.4Hz,1H),8.81(s,1H),8.69-8.59(m,1H),8.59-8.51(m,1H),8.06-7.89(m,1H),4.40(q,J=7.2Hz,1H),4.33-4.20(m,2H),2.36(s,3H),2.09(s,3H),1.95-1.68(m,2H),1.54(d,J=7.2Hz,3H),1.09-0.98(m,3H)
1-272;
(異性体比3)9.03-8.93(m,1H),8.61(s,1H),8.54-8.45(m,1H),8.42(s,1H),8.04-7.92(m,1H),7.43-7.32(m,1H),4.40(q,J=7.2Hz,1H),4.24-4.03(m,2H),2.38(s,3H),2.19(s,3H),1.67(d,J=7.2Hz,3H),1.37-1.08(m,1H),0.74-0.58(m,2H),0.46-0.30(m,2H)
(異性体比2)9.67(s,1H),9.03-8.93(m,1H),8.67(s,1H),8.54-8.45(m,1H),8.04-7.92(m,1H),7.43-7.32(m,1H),4.24-4.03(m,3H),2.38(s,3H),2.10(s,3H),1.54(d,J=7.2Hz,3H),1.37-1.08(m,1H),0.74-0.58(m,2H),0.46-0.30(m,2H)
1-273;
8.99(d,J=2.4Hz,1H),8.61(s,1H),8.49(dd,J=4.8,1.2Hz,1H),8.28(s,1H),8.04-7.91(m,1H),7.47-7.31(m,3H),6.90-6.78(m,2H),4.48(dd,J=8.7,7.2Hz,1H),3.93(s,3H),3.80(s,3H),2.37(s,3H),2.31-2.02(m,2H),1.00(t,J=7.2Hz,3H)
1-274;
(異性体比3)9.12-8.93(m,2H),8.63(s,1H),8.54-8.35(m,1H),8.04-7.94(m,1H),7.44-7.30(m,1H),5.32(s,2H),4.06(q,J=7.2Hz,1H),2.38(s,3H),2.32(s,3H),2.14(s,3H),1.55(d,J=7.2Hz,3H)
(異性体比1)9.12-8.93(m,2H),8.60(s,1H),8.54-8.35(m,1H),8.04-7.94(m,1H),7.44-7.30(m,1H),5.32(s,2H),4.40(q,J=7.2Hz,1H),2.38(s,3H),2.31(s,3H),2.20(s,3H),1.68(d,J=7.2Hz,3H)
1-275;
(異性体比6)11.1(brs,1H),9.35-8.85(m,2H),8.70-8.40(m,2H),8.05-7.80(m,1H),7.70-7.50(m,1H),7.50-7.20(m,6H),4.85(q,J=7.2Hz,1H),2.35(s,3H),2.14(s,3H),1.48(d,J=7.2Hz,3H)
(異性体比5)10.1(brs,1H),9.35-8.85(m,2H),8.70-8.40(m,2H),8.05-7.80(m,1H),7.70-7.50(m,1H),7.50-7.20(m,6H),3.92(q,J=7.2Hz,1H),2.40(s,3H),2.22(s,3H),1.67(d,J=7.2Hz,3H)
1-276;
11.4(brs,1H),10.0(brs,1H),9.01(d,J=2.4Hz,1H),8.60(s,1H),8.51(dd,J=4.8,1.5Hz,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.38(dd,J=8.4,4.8Hz,1H),6.20(t,J=6.3Hz,1H),6.00-5.85(m,1H),5.30-5.10(m,2H),4.05-3.90(m,2H),3.85(q,J=7.2Hz,1H),2.39(s,3H),2.19(s,3H),1.61(d,J=7.2Hz,3H)
1-280;
(異性体比2)11.3(brs,1H),10.0-9.85(m,1H),9.00(d,J=2.4Hz,1H),8.59(s,1H),8.55-8.45(m,1H),8.05-7.95(m,1H),7.45-7.30(m,1H),5.99(d,J=7.8Hz,1H),4.30-4.05(m,1H),3.84(q,J=7.2Hz,1H),2.39(s,3H),2.17(s,3H),1.80-1.40(m,11H)
(異性体比1)10.0-9.85(m,1H),8.97(d,J=2.4Hz,1H),8.54(s,1H),8.55-8.45(m,1H),8.34(brs,1H),8.05-7.95(m,1H),7.45-7.30(m,1H),5.75(d,J=7.8Hz,1H),4.80(q,J=7.2Hz,1H),4.30-4.05(m,1H),2.37(s,3H),2.08(s,3H),1.80-1.40(m,11H)
1-282;
11.2(brs,1H),9.10(brs,1H),9.00-8.90(m,1H),8.60-8.40(m,2H),8.10-7.95(m,1H),7.37(dd,J=8.4,4.8Hz,1H),5.85-5.75(m,1H),4.88(q,J=7.2Hz,1H),3.11(s,2H),2.39(s,3H),2.08(s,3H),1.80-1.40(m,11H)
1-285;
8.98(d,J=2.4Hz,1H),8.55(brs,1H),8.53-8.48(m,1H),8.34(brs,1H),8.04-7.96(m,1H),7.38(dd,J=8.1,4.8Hz,1H),5.16(dd,J=9.6,6.6Hz,1H),4.20(s,3H),3.44-3.14(m,2H),3.11(s,3H),2.38(s,3H),2.10(t,J= 2.7Hz,1H)
1-286;
10.63(brs,1H),9.01(brs,1H),8.83(s,1H),8.62(brs,1H),8.15-8.05(m,1H),7.55-7.35(m,1H),4.20-4.05(m,4H),2.70(s,3H),2.20-1.90(m,5H),1.00(t,J=7.5Hz,3H)
1-287;
8.91(s,1H),8.53(d,J=4.5Hz,1H),8.05-7.95(m,1H),7.98(s,1H),7.40(dd,J=8.4,4.5Hz,1H),3.95-3.80(m,4H),2.74(s,3H),2.43(s,3H),2.10-1.90(m,1H),1.90-1.70(m,4H),1.03(t,J=7.2Hz,3H)
1-289;
(異性体比3)9.20-8.96(m,1H),8.68(s,1H),8.60-8.52(m,1H),8.46(s,1H),8.08-7.94(m,1H),7.48-7.36(m,1H),4.70-4.56(m,2H),4.41(q,J=7.2Hz,1H),2.17(s,3H),1.68(d,J=7.2Hz,3H)
(異性体比2)9.20-8.96(m,1H),8.77(s,1H),8.70(s,1H),8.60-8.52(s,1H),8.08-7.94(m,1H),7.48-7.36(m,1H),4.70-4.56(m,2H),3.99(q,J=7.2Hz,1H),2.11(s,3H),1.54(d,J=7.2Hz,3H)
1-290;
(異性体比4)10.1(brs,1H),9.00-8.90(m,1H),8.58(s,1H),8.50-8.40(m,1H),8.10-7.90(m,3H),7.85-7.70(m,3H),7.35-7.20(m,1H),4.45-4.25(m,1H),2.41(s,3H),2.30(s,3H),1.50(d,J=7.2Hz,3H)
(異性体比1)10.5(brs,1H),9.00-8.90(m,1H),8.56(s,1H),8.50-8.40(m,1H),8.10-7.90(m,3H),7.85-7.70(m,3H),7.35-7.20(m,1H),4.45-4.25(m,1H),2.43(s,3H),2.16(s,3H),1.62(d,J=7.2Hz,3H)
1-292;
8.97(d,J=2.7Hz,1H),8.62(brs,1H),8.53(s,1H),8.46(dd,J=4.8,1.2Hz,1H),8.05-7.80(m,2H),7.35(dd,J=8.4,4.8Hz,1H),4.83(q,J=7.2Hz,1H),3.50-3.35(m,2H),2.42(s,3H),2.01(s,3H),1.47(d,J=7.2Hz,3H),1.27(t,J=7.2Hz,3H)
1-293;
11.8(brs,1H),10.2(brs,1H),8.96(d,J=2.4Hz,1H),8.60(s,1H),8.52(dd,J=4.8,1.2Hz,1H),8.05(ddd,J=8.4,2.4,1.2Hz,1H),7.41(dd,J=8.4,4.8Hz,1H),4.01(q,J=7.2Hz,1H),3.84(s,3H),2.40(s,3H),2.20(s,3H),1.59(d,J=7.2Hz,3H)
1-296;
11.9(brs,1H),10.3(brs,1H),9.00(d,J=2.7Hz,1H),8.61(s,1H),8.60-8.50(m,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.40(dd,J=8.4,4.8Hz,1H),6.10-5.85(m,1H),5.45-5.20(m,2H),4.73(d,J=6,0Hz,2H),4.01(q,J=7.2Hz,1H),2.40(s,3H),2.21(s,3H),1.59(d,J=7.2Hz,3H)
1-297;
9.00(d,J=3.0Hz,1H),8.70-8.60(m,2H),8.55-8.45(m,1H),8.10-8.00(m,1H),7.50-7.35(m,1H),4.24(q,J=7.2Hz,1H),2.38(s,3H),2.19(s,3H),2.19(s,3H),1.59(d,J=7.2Hz,3H)(NHのプロトンピークは観測されなかった)
1-298;
(異性体比4)13.0(brs,1H),10.4(brs,1H),9.05-8.90(m,1H),8.65-8.45(m,2H),8.10-7.90(m,1H),7.45-7.30(m,1H),6.85-6.70(m,1H),4.20-4.00(m,1H),2.80-2.50(m,6H),2.41(s,3H),2.22(s,3H),1.62(d,J=7.2Hz,3H)
(異性体比1)9.05-8.90(m,1H),8.65-8.45(m,3H),8.10-7.90(m,1H),7.45-7.30(m,1H),6.75-6.65(m,1H),4.20-4.00(m,1H),2.80-1.95(m,9H),2.34(s,3H),1.70-1.50(m,3H)(NHのプロトンピークは観測されなかった)
1-299;
8.87(d,J=2.4Hz,1H),8.52(d,J=4.8Hz,1H),8.10-7.90(m,2H),7.39(dd,J=8.1,4.8Hz,1H),4.00-3.60(m,8H),2.34(s,3H),2.15-1.90(m,1H),1.80-1.60(m,4H),1.01(t,J=7.2Hz,3H),0.86(s,9H),0.10-0.02(m,6H)
1-306;
9.03(d,J=2.4Hz,1H),8.94(brs,1H),8.88(s,1H),8.63(dd,J=4.8,1.2Hz,1H),8.08(ddd,J=8.1,2.4,1.2Hz,1H),7.44(dd,J=8.1,4.8Hz,1H),4.20-4.05(m,4H),2.20-1.95(m,5H),1.00(t,J=7.5Hz,3H)
1-307;
8.93(d,J=2.7Hz,1H),8.59(dd,J=4.5,1.5Hz,1H),8.07(ddd,J=8.1,2.7,1.5Hz,1H),8.02(s,1H),7.43(dd,J=8.1,4.5Hz,1H),4.20-3.75(m,3H),3.75(s,3H),2.10-1.70(m,5H),1.23(t,J=7.2Hz,3H),1.01(t,J=7.2Hz,3H),0.26(s,9H)
1-309;
11.6(brs,1H),10.1(brs,1H),9.00(d,J=2.1Hz,1H),8.65-8.45(m,2H),7.99(ddd,J=8.4,2.1,1.2Hz,1H),7.45-7.35(m,1H),3.85(q,J=7.5Hz,1H),3.13(s,3H),2.39(s,3H),2.20(s,3H),1.60(d,J=7.5Hz,3H)
1-312;
9.70-9.50(m,1H),9.10-8.80(m,1H),8.70-8.45(m,1H),8.20-7.70(m,2H),7.50-7.30(m,1H),4.00-3.55(m,8H),3.34(s,3H),2.45-2.00(m,6H),1.41(d,J=7.5Hz,3H)
1-313;
(異性体比5)9.05-8.85(m,2H),8.68(s,1H),8.55-8.45(m,1H),8.10-7.95(m,1H),7.45-7.30(m,1H),3.95-3.70(m,1H),3.25(s,3H),2.40-2.05(m,6H),1.80(d,J=7.2Hz,3H),1.60-1.40(m,9H)
(異性体比3)9.05-8.85(m,2H),8.54(s,1H),8.55-8.45(m,1H),8.10-7.95(m,1H),7.45-7.30(m,1H),3.95-3.70(m,1H),3.17(s,3H),2.40-2.05(m,6H),1.60-1.40(m,12H)
1-314;
8.98(d,J=2.7Hz,1H),8.59(s,1H),8.52-8.46(m,1H),8.30(s,1H),8.04-7.92(m,1H),7.42-7.32(m,1H),4.80(s,2H),4.47(q,J=7.2Hz,1H),4.28(q,J=7.2Hz,2H),2.35(s,3H),2.23(s,3H),1.70(d,J=7.2Hz,3H),1.33(t,J=7.2Hz,3H)
1-315;
(異性体比7)8.59(s,1H),8.53-8.46(m,1H),8.38(s,1H),8.04-7.94(m,1H),7.42-7.32(m,1H),4.74(s,2H),4.39(q,J=7.2Hz,1H),3.93(s,3H),2.37(s,3H),2.18(s,3H),1.95(s,3H),1.66(d,J=7.2Hz,3H)
(異性体比3)8.98(d,J=2.4Hz,1H),8.59(s,1H),8.53-8.46(m,1H),8.32(s,1H),8.04-7.94(m,1H),7.42-7.32(m,1H),5.07(s,2H),4.39(q,J=7.2Hz,1H),3.88(s,3H),2.37(s,3H),2.20(s,3H),1.98(s,3H),1.67(d,J=7.2Hz,3H)
1-316;
(異性体比4)9.29(s,1H),9.03-8.96(m,1H),8.65(s,1H),8.52-8.46(m,1H),8.02-7.94(m,1H),7.42-7.32(m,1H),5.24-5.18(m,1H),4.50-4.05(m,3H),4.05-3.90(m,4H),2.38(s,3H),2.09(s,3H),1.53(d,J=7.2Hz,3H)
(異性体比1)9.03-8.96(m,1H),8.60(s,1H),8.52-8.46(m,1H),8.42(s,1H),8.02-7.94(m,1H),7.42-7.32(m,1H),5.24-5.18(m,1H),4.50-4.05(m,3H),4.05-3.90(m,4H),2.37(s,3H),2.17(s,3H),1.66(d,J=7.2Hz,3H)
1-318;
(異性体比7)8.96(s,1H),8.92(s,1H),8.61(s,1H),8.52-8.46(m,1H),8.02-7.94(m,1H),7.74-7.66(m,2H),7.58-7.48(m,2H),7.42-7.33(m,1H),5.30(s,2H),3.96(q,J=7.2Hz,1H),2.20(s,3H),2.01(s,3H),1.49(d,J=7.2Hz,3H)
(異性体比3)8.97(s,1H),8.56(s,1H),8.52-8.46(m,1H),8.27(s,1H),8.02-7.94(m,1H),7.74-7.66(m,2H),7.58-7.48(m,2H),7.42-7.33(m,1H),5.34(s,2H),4.40(q,J=7.2Hz,1H),2.32(s,3H),2.16(s,3H),1.65(d,J=7.2Hz,3H)
1-319;
(異性体比7)9.31(s,1H),9.00-8.90(m,1H),8.60(s,1H),8.50-8.45(m,1H),8.02-7.88(m,1H),7.40-7.22(m,5H),5.22(s,2H),4.12(q,J=7.2Hz,1H),2.49(s,3H),2.02(s,3H),2.00(s,3H),1.53(d,J=7.2Hz,3H)
(異性体比3)9.00-8.90(m,1H),8.58(s,1H),8.50-8.45(m,1H),8.33(s,1H),8.02-7.88(m,1H),7.40-7.22(m,5H),5.21(s,2H),4.39(q,J=7.2Hz,1H),2.49(s,3H),2.33(s,3H),2.11(s,3H),1.63(d,J=7.2Hz,3H)
1-320;
10.5(s,1H),9.06-8.90(m,1H),8.70-6.90(m,9H),4.22-4.08(m,1H),3.04-2.94(m,1H),2.43(s,3H),2.26(s,3H),2.10-1.90(m,2H),1.65(d,J=7.2Hz,3H)
1-321;
8.98(d,J=2.4Hz,1H),8.58(s,1H),8.50(dd,J=4.8,1.5Hz,1H),8.31(brs,1H),7.99(ddd,J=8.1,2.4,1.5Hz,1H),7.37(dd,J=8.1,4.8Hz,1H),4.41(t,J=8.1Hz,1H),4.11(s,3H),3.31(d,J=8.1Hz,2H),2.99(ddd,J=14.4,6.9,2.7Hz,2H),2.78(ddd,J=14.4,9.0,2.7Hz,2H),2.38(s,3H),2.20-1.90(m,2H)
1-322;
8.95-8.85(m,1H),8.52(dd,J=4.8,1.5Hz,1H),8.10-7.90(m,2H),7.39(dd,J=8.1,4.8Hz,1H),4.27(t,J=7.5Hz,1H),3.69(s,3H),3.30(s,3H),3.11(d,J=7.5Hz,2H),3.00-2.88(m,2H),2.81(ddd,J=14.4,9.3,3.3Hz,2H),2.31(s,3H),2.20-1.80(m,2H)
1-323;
(異性体比1)8.98(d,J=2.4Hz,1H),8.58-8.46(m,2H),8.42-8.30(m,1H),8.05-7.98(m,1H),7.39(dd,J=8.4,4.8Hz,1H),4.12-3.92(m,1H),4.08(s,3H),3.33(dd,J=12.9,7.2Hz,1H),3.23(dd,J=12.9,8.1Hz,1H),2.63(s,3H),2.37(s,3H),1.46-1.38(m,3H)
(異性体比1)8.98(d,J=2.4Hz,1H),8.58-8.46(m,2H),8.42-8.30(m,1H),8.05-7.98(m,1H),7.39(dd,J=8.4,4.8Hz,1H),4.12-3.92(m,1H),4.09(s,3H),3.57(dd,J=13.2,10.2Hz,1H),3.00-2.90(m,1H),2.61(s,3H),2.37(s,3H),1.46-1.38(m,3H)
1-324;
8.98(d,J=2.7Hz,1H),8.54-8.46(m,2H),8.31(brs,1H),8.05-7.98(m,1H),7.42-7.35(m,1H),4.16-3.92(m,2H),4.11(s,3H),3.28-3.18(m,1H),2.93(s,3H),2.36(s,3H),1.46-1.38(m,3H)
1-325;
(異性体比3)8.93-8.86(m,1H),8.56-8.50(m,1H),8.04-7.93(m,1H),7.92(s,1H),7.39(dd,J=8.4,4.8Hz,1H),3.70(s,3H),3.27(s,3H),3.25-3.12(m,1H),2.95-2.82(m,1H),2.66-2.52(m,1H),2.31(s,3H),2.04(s,3H),1.21(d,J=7.2Hz,3H)
(異性体比1)8.93-8.86(m,1H),8.56-8.50(m,1H),8.04-7.93(m,1H),7.92(s,1H),7.39(dd,J=8.4,4.8Hz,1H),3.99(s,3H),3.46(s,3H),3.25-3.12(m,1H),2.95-2.82(m,1H),2.66-2.52(m,1H),2.31(s,3H),2.05(s,3H),1.33(d,J=7.2Hz,3H)
1-326;
8.98(d,J=2.4Hz,1H),8.64(s,1H),8.60-8.50(m,2H),8.01(ddd,J=8.4,2.4,1.2Hz,1H),7.40(dd,J=8.4,4.8Hz,1H),4.08(s,3H),3.78-3.64(m,1H),3.10(dd,J=13.2,9.6Hz,1H),2.73(dd,J=13.2,6.9Hz,1H),2.11(s,3H),1.34(t,J=7.2Hz,3H)
1-327;
9.04-8.92(m,1H),8.63-8.46(m,2H),8.24(brs,1H),8.10-7.88(m,1H),7.58-7.18(m,6H),5.83(s,1H),4.13(s,3H),2.36(s,3H)
1-328;
9.06-8.98(m,1H),8.75-8.30(m,2H),8.62(s,1H),8.08-7.98(m,1H),7.52-7.38(m,1H),5.50-5.36(m,2H),4.03(s,3H),2.34(s,3H),2.04-1.96(m,3H)
1-330;
9.08(brs,1H),9.00-8.90(m,1H),8.65-8.40(m,2H),8.05-7.90(m,1H),7.40-7.30(m,1H),4.00-3.55(m,3H),2.36(s,3H),2.25-2.10(m,6H),1.57(d,J=7.2Hz,3H),1.25(t,J=6.9Hz,3H)
1-331;
9.05-8.95(m,2H),8.60(s,1H),8.50-8.40(m,1H),8.05-7.90(m,1H),7.40-7.30(m,1H),4.21(q,J=7.2Hz,1H),4.05(s,3H),3.45-3.20(m,2H),2.32(s,3H),2.26(t,J=2.4Hz,1H),1.58(d,J=7.2Hz,3H)
1-333;
(異性体比4)8.92(d,J=2.4Hz,1H),8.53(dd,J=4.8,1.2Hz,1H),8.01(ddd,J=8.4,2.4,1.2Hz,1H),7.97(s,1H),7.40(dd,J=8.4,4.8Hz,1H),4.77(t,J=8.1Hz,1H),3.70(s,3H),3.35-3.20(m,7H),3.03(d,J=8,1Hz,2H),2.33(s,3H)
(異性体比1)8.92(d,J=2.4Hz,1H),8.53(dd,J=4.8,1.2Hz,1H),8.01(ddd,J=8.4,2.4,1.2Hz,1H),7.97(s,1H),7.40(dd,J=8.4,4.8Hz,1H),4.96(t,J=7.8Hz,1H),4.01(s,3H),3.53(s,3H),3.35-3.20(m,4H),3.11(d,J=7.8Hz,2H),2.33(s,3H)
1-334;
8.92-8.88(m,1H),8.52(dd,J=4.8,1.2Hz,1H),8.00(ddd,J=8.4,2.7,1.2Hz,1H),7.95(s,1H),7.38(dd,J=8.4,4.8Hz,1H),5.05(s,2H),4.30-4.20(m,1H),4.07(s,3H),3.71(s,3H),3.20-3.10(m,2H),3.00-2.90(m,2H),2.85-2.70(m,2H),2.30(s,3H),2.15-2.00(m,1H),2.00-1.85(m,1H)
1-335;
9.50-8.90(m,1H),8.75-8.50(m,3H),8.05-7.90(m,1H),7.45-7.35(m,1H),4.45-4.05(m,4H),3.80-3.60(m,1H),2.60-2.20(m,1H),2.25-2.13(m,3H),1.75-1.50(m,3H),1.25-1.00(m,3H)(NH2のプロトンピークは観測されなかった)
1-336;
8.95-8.85(m,1H),8.60-8.45(m,1H),8.06-7.92(m,2H),7.45-7.35(m,1H),5.92-5.58(m,1H),5.30-4.90(m,2H),3.95-3.84(m,1H),3.80-3.70(m,3H),3.35-3.26(m,3H),3.26-2.50(m,2H),2.50-2.30(m,3H),2.30-1.60(m,2H),1.15-0.90(m,3H)
1-337;
8.97(d,J=2.4Hz,1H),8.68(s,1H),8.60-8.52(m,1H),8.44(s,1H),8.06-7.94(m,1H),7.45-7.35(m,1H),4.82(s,2H),4.46(q,J=7.2Hz,1H),2.26(s,3H),2.23(s,3H),1.70(d,J=7.2Hz,3H)
1-338;
9.46-9.34 and 8.36-8.30(m,1H),9.02-8.94(m,1H),8.62 and 8.58(s,1H),8.54-8.46(m,1H),8.04-7.94(m,1H),7.42-7.32(m,1H),6.03-5.84(m,1H),5.55-5.30(m,2H),4.65-4.55 and 4.40-4.30(m,1H),4.14 and 4.13(s,3H),3.72-3.60 and 3.34-3.24(m,1H),3.52-3.38(m,1H),2.40 and 2.39(s,3H),2.35-1.83(m,2H),1.10-0.95(m,3H)
1-342;
8.98(d,J=2.4Hz,1H),8.62-8.40(m,3H),8.04-7.92(m,1H),7.44-7.34(m,1H),6.06-5.86(m,1H),5.58-5.46(m,2H),5.04-4.92(m,1H),4.20-4.10(m,3H),3.92(d,J=7.2Hz,2H),2.62-2.42(m,1H),2.41-2.35(m,3H),2.35-2.10(m,1H),1.04-0.60(m,3H)
1-343;
8.99(s,1H),8.56(s,1H),8.54-8.45(m,1H),8.45-8.30(m,1H),8.10-7.90(m,1H),7.44-7.30(m,1H),4.06(s,3H),3.68-3.54(m,1H),3.11(dd,J=13.5,10.2Hz,1H),2.78(dd,J=13.5,6.0Hz,1H),2.39(s,3H),2.12(s,3H),2.06-1.85(m,1H),1.85-1.65(m,1H),0.93(t,J=7.5Hz,3H)
1-344;
8.99(s,1H),8.56(s,1H),8.54-8.45(m,1H),8.45-8.30(m,1H),8.10-7.90(m,1H),7.44-7.30(m,1H),4.06(s,3H),3.48-3.23(m,2H),2.39(s,3H),2.12(s,3H),1.43(d,J=6.9Hz,3H),1.26(d,J=6.9Hz,3H)
3-002;
9.09(d,J=1.8Hz,1H),8.70(dd,J=4.8,1.2Hz,1H),8.20(ddd,J=8.1,1.8,1.2Hz,1H),7.40(dd,J=8.1,4.8Hz,1H),3.92-3.81(m,2H),3.36(brs,3H),3.54(s,2H),2.08(s,3H),1.28(t,J=7.2Hz,3H)
3-006;
9.10-9.07(m,1H),8.65(dd,J=4.8,1.5Hz,1H),8.21-8.17(m,1H),7.40-7.34(m,1H),5.20(brs,2H),4.15-4.00(m,1H),3.84-3.65(m,5H),2.40(s,3H),2.04(brs,3H),1.51(d,J=7.8Hz,3H),1.26(t,J=7.2Hz,3H)
3-007;
9.20-9.00(m,1H),8.70-8.60(m,1H),8.30-8.10(m,1H),7.50-7.30(m,1H),6.10-5.60(m,2H),4.25-4.00(m,3H),4.00-3.75(m,1H),2.65-2.45(m,3H),2.45-2.20(m,3H),2.20-2.20(m,3H),1.72―1.50(m,3H)
3-008;
9.10(d,J=2.1Hz,1H),8.65(dd,J=4.8,1.8Hz,1H),8.19(ddd,J=7.5,2.1,1.8Hz,1H),7.38(dd,J=7.5,4.8Hz,1H),4.75-4.35(m,2H),4.15-4.00(m,1H),3.90-3.65(m,3H),2.43(s,3H),2.35-2.25(m,1H),2.20-1.95(m,3H),1.51(d,J=7.2Hz,3H)
3-010;
(異性体比88)9.10(d,J=1.5Hz,1H),8.66(dd,J=4.8,1.5Hz,1H),8.18(ddd,J=8.1,1.5,1.5Hz,1H),7.38(dd,J=8.1,4.8Hz,1H),4.20(q,J=7.5Hz,1H),3.99(s,3H),3.83(s,3H),2.36(s,3H),2.19(s,3H),1.58(d,J=7.5Hz,3H)
(異性体比12)9.10(d,J=1.5Hz,1H),8.66(dd,J=4.8,1.5Hz,1H),8.18(ddd,J=8.1,1.5,1.5Hz,1H),7.38(dd,J=8.1,4.8Hz,1H),4.20(q,J=7.5Hz,1H),3.92(s,3H),3.83(s,3H),2.33(s,3H),2.15(s,3H),1.58(d,J=7.5Hz,3H)
3-012;
(異性体比9)9.12-9.07(m,1H),8.68-8.60(m,1H),8.22-8.14(m,1H),7.39(dd,J=7.5,4.8Hz,1H),4.35-3.15(m,6H),2.41(s,3H),2.03(brs,3H),1.68-1.40(m,3H),1.20-1.00(m,1H),0.60-0.48(m,2H), 0.32-0.18(m,2H)
(異性体比1)9.07-9.03(m,1H),8.75-8.71(m,1H),8.22-8.14(m,1H),7.39(dd,J=7.5,4.8Hz,1H),4.35-3.15(m,6H),2.41(s,3H),2.03(brs,3H),1.68-1.40(m,3H),1.20-1.00(m,1H),0.60-0.48(m,2H), 0.32-0.18(m,2H)
3-013;
(異性体比56)9.16-9.10(m,1H),8.92(brs,1H),8.64-8.8.56(m,1H),8.20-8.12(m,1H),7.40-7.30(m,1H),4.38(q,J=7.2Hz,1H),4.15(s,3H),2.55(s,3H),2.49(s,3H),1.71(d,J=7.2Hz,3H)
(異性体比44)10.23(brs,1H),9.16-9.10(m,1H),8.64-8.8.56(m,1H),8.20-8.12(m,1H),7.40-7.30(m,1H),4.58(q,J=7.2Hz,1H),4.15(s,3H),2.69(s,3H),2.50(s,3H),1.65(d,J=7.2Hz,3H)
3-017;
9.11(d,J=2.4Hz,1H),8.90(brs,1H),8.61(dd,J=4.8,1.8Hz,1H),8.17(ddd,J=8.4,2.4.1.8Hz,1H),7.35(dd,J=8.4,4.8Hz,1H),4.87(dd,J=10.8,5.1Hz,1H),4.19(s,3H),3.10(s,3H),2.55-2.40(m,4H),2.35-2.20(m,1H),1.03(t,J=7.2Hz,3H)
3-023;
9.13(d,J=1.8Hz,1H),8.87(s,1H),8.63-8.57(m,1H),8.20-8.12(m,1H),7.39-7.30(m,1H),4.28(t,J=7.8Hz,1H),4.11(s,3H),3.30-3.00(m,2H),2.49(s,3H),2.19-1.96(m,2H),1.00(t,J=7.5Hz,3H)
3-024;
9.16-9.10(m,1H),8.84(brs,1H),8.68-8.63(m,1H),8.63-8.57(m,1H),8.20-8.15(m,1H),7.68-7.62(m,1H),7.40-7.30(m,1H),7.28-7.23(m,1H),5.70(t,J=8.1Hz,1H),4.13(s,3H),2.48(s,3H),2.27-2.00(m,2H),1.03(t,J=7.5Hz,3H)
3-026;
9.13(d,J=1.5Hz,1H),8.67(dd,J=4.8,1.5Hz,1H),8.26-8.20(m,1H),7.80(s,1H),7.44-7.38(m,1H),4.20(q,J=7.2Hz,1H),4.00(s,3H),2.19(s,3H),1.56(d,J=7.2Hz,3H)(NHのプロトンピークは観測されなかった)
3-028;
9.60-9.52(m,1H),9.14(d,J=2.1Hz,1H),8.60(dd,J=4.8,1.8Hz,1H),8.18(m,1H),7.37(dd,J=7.5,4.8Hz,1H),4.80-4.70(m,1H),4.13(s,3H),3.43(s,3H),2.48(s,3H),2.07-1.90(m,1H),1.90-1.73(m,1H),0.96(t,J=7.5Hz,3H)
3-029;
(異性体比7)9.12(d,J=1.5Hz,1H),8.95(s,1H),8.59(dd,J=4.8,1.5Hz,1H),8.20-8.13(m,1H),7.34(dd,J=8.1,4.8Hz,1H),5.90-5.74(m,1H),5.20-5.05(m,2H),4.09(s,3H),3.16(d,J=7.2Hz,2H),2.73-2.45(m,1H),2.49(s,3H),2.16-1.75(m,2H),0.97(t,J=7.2Hz,3H)
(異性体比3)9.12(d,J=1.5Hz,1H),8.93(s,1H),8.59(dd,J=4.8,1.5Hz,1H),8.20-8.13(m,1H),7.34(dd,J=8.1,4.8Hz,1H),5.90-5.74(m,1H),5.20-5.05(m,2H),4.09(s,3H),3.11(d,J=7.2Hz,2H),2.73-2.45(m,1H),2.49(s,3H),2.16-1.75(m,2H),1.05-0.93(m,3H)
3-032;
9.13(d,J=1.8Hz,1H),9.02(s,1H),8.61(dd,J=4.8,1.8Hz,1H),8.22-8.10(m,1H),7.41-7.30(m,1H),4.30-4.15(m,1H),4.11(s,3H),2.74-2.60(m,1H),2.50(s,3H),2.20-1.55(m,7H),1.42-1.18(m,5H),0.99(t,J=7.2Hz,3H)
3-033;
9.17-9.10(m,1H),8.81(s,1H),8.61(dd,J=4.8,1.5Hz,1H),8.24-8.12(m,1H),7.49-7.33(m,3H),6.89-6.78(m,2H),4.48(dd,J=8.7,7.8Hz,1H),3.96(s,3H),3.79(s,3H),2.48(s,3H),2.30-2.02(m,2H),1.00(t,J=7.8Hz,3H)
3-034;
9.14-9.10(m,1H),8.85(brs,1H),8.62(dd,J=4.8,1.8Hz,1H),8.22-8.14(m,1H),7.40-7.32(m,1H),5.19-5.10(m,1H),4.22(s,3H),3.42-3.18(m,2H),3.11(s,3H),2.49(s,3H),2.11(t,J= 2.7Hz,1H)
3-036(*3);
9.15-9.05(m,2H),8.70-8.60(m,1H),8.58(dd,J=4.8,1.5Hz,1H),8.25-8.10(m,1H),7.40-7.30(m,1H),4.82(q,J=7.5Hz,1H),4.05-3.90(m,2H),2.46(s,3H),2.02(s,3H),1.48(d,J=7.5Hz,3H)
3-040;
12.7(brs,1H),11.3(brs,1H),9.20-9.10(m,1H),8.63(dd,J=4.8,1.5Hz,1H),8.35-8.20(m,1H),7.45-7.35(m,1H),4.20-4.05(m,3H),3.52(s,3H),2.54(s,3H),2.24(s,3H),1.61(d,J=7.2Hz,3H)
3-043;
11.3(brs,1H),10.7(brs,1H),9.20-9.10(m,1H),8.63(dd,J=4.8,1.2Hz,1H),8.18(ddd,J=8.4,2.7,1.2Hz,1H),7.37(dd,J=8.4,4.8Hz,1H),6.18(t,J=5.4Hz,1H),6.00-5.85(m,1H),5.30-5.10(m,2H),4.10-3.90(m,2H),3.89(q,J=7.2Hz,1H),2.53(s,3H),2.20(s,3H),1.61(d,J=7.2Hz,3H)
3-045;
(異性体比2)11.2(brs,1H),9.40-8.90(m,2H),8.65-8.50(m,1H),8.25-8.10(m,1H),7.70-7.25(m,7H),4.83(q,J=7.2Hz,1H),2.47(s,3H),2.13(s,3H),1.80-1.50(m,3H)
(異性体比1)12.4(brs,1H),10.8(brs,1H),9.40-8.90(m,1H),8.65-8.50(m,1H),8.25-8.10(m,1H),7.70-7.25(m,7H),3.95(q,J=7.2Hz,1H),2.54(s,3H),2.24(s,3H),1.80-1.50(m,3H)
3-047;
9.21(brs,1H),9.20-9.10(m,1H),8.57(dd,J=4.8,1.2Hz,1H),8.25-8.10(m,2H),7.40-7.30(m,1H),6.10-5.85(m,1H),5.40-5.20(m,2H),4.79(q,J=7.2Hz,1H),4.15-4.00(m,2H),2.46(s,3H),2.02(s,3H),1.46(d,J=7.2Hz,3H)
3-048;
9.20(brs,1H),9.13(d,J=2.4Hz,1H),8.57(dd,J=4.8,1.5Hz,1H),8.25-8.05(m,2H),7.40-7.30(m,1H),4.79(q,J=7.2Hz,1H),3.55-3.40(m,2H),2.48(s,3H),2.01(s,3H),1.46(d,J=7.2Hz,3H),1.29(t,J=7.2Hz,3H)
3-055;
9.64 and 9.15(brs,1H),9.12(brs,1H),8.70-8.62(m,1H),8.25-8.15(m,1H),7.44-7.36(m,1H),4.65(q,J=8.1Hz,2H),4.41 and 4.03(q,J=7.5Hz,1H),2.16 and 2.09(s,3H),1,86 and 1.54(d,J=7.5Hz,3H)
4-002;
(異性体比5)9.05(d,J=2.7Hz,1H),8.60-8.50(m,1H),8.50(s,1H),8.15-8.00(m,1H),7.39(dd,J=8.4,4.8Hz,1H),6.10-5.90(m,2H),4.47(q,J=7.2Hz,1H),4.05(s,3H),3.45-3.05(m,4H),2.22(s,3H),1.71(d,J=7.2Hz,3H),1.05-0.80(m,6H)
(異性体比3)8.84(d,J=2.7Hz,1H),8.60-8.50(m,1H),8.05-7.95(m,1H),7.76(s,1H),7.35-7.20(m,1H),6.10-5.90(m,2H),4.25-4.05(m,1H),3.94(s,3H),3.45-3.05(m,4H),1.88(s,3H),1.37(d,J=7.2Hz,3H),1.25-1.10(m,6H)
6-001;
8.76(s,1H),8.70-8.60(m,1H),8.16(brs,1H),8.05-7.95(m,1H),7.86(ddd,J=8.1,2.1,1.2Hz,1H),7.46(dd,J=8.1,4.2Hz,1H),4.18-4.02(m,4H),2.34(s,3H),2.17(s,3H),2.15-1.90(m,2H),1.10-0.90(m,3H)
6-002;
8.95-8.85(m,1H),8.70-8.60(m,1H),7.91(dd,J=8.1,1.5Hz,1H),7.50-7.40(m,1H),3.85-3.75(m,4H),3.35-3.20(m,3H),2.40-2.30(m,3H),2.10-1.80(m,5H),1.10-0.90(m,3H)
―――――――――――――――――――――――――――――――――― [Table 12]
――――――――――――――――――――――――――――――――――
No.
Proton nuclear magnetic resonance chemical shift value (CDCl 3 Middle): σ (ppm)
――――――――――――――――――――――――――――――――――
1-002;
(Isomer ratio 92) 9.02-8.92 (m, 1H), 8.63-8.56 (m, 1H), 8.09 (s, 1H), 8.05-7.94 (m, 1H), 7.47-7.38 (m, 1H), 4.62 (q, J = 7.2Hz, 1H), 3.95 (dq, J = 13.8,6.9Hz, 1H), 3.77 (s, 3H), 3.56 (dq, J = 13.8,6.6Hz, 1H), 2.94 (s, 3H), 1.76 (d, J = 7.2Hz, 3H), 1.30-1.19 (m, 3H)
(Isomer ratio 8) 9.02-8.92 (m, 1H), 8.63-8.56 (m, 1H), 8.09 (s, 1H), 8.05-7.94 (m, 1H), 7.47-7.38 (m, 1H), 4.90 -4.78 (m, 1H), 3.95 (dq, J = 13.8,6.9Hz, 1H), 3.77 (s, 3H), 3.56 (dq, J = 13.8,6.6Hz, 1H), 3.02 (s, 3H), 1.76 (d, J = 7.2Hz, 3H), 1.30-1.19 (m, 3H)
1-007;
(Isomer ratio 5) 9.06 (d, J = 2.4Hz, 1H), 8.77 (s, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.12 (ddd, J = 8.4,2.4,1.2 Hz, 1H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 4.30-4.10 (m, 4H), 3.75-3.65 (m, 2H), 3.43 (s, 3H), 2.35-2.20 (m, 2H), 1.18 (t, J = 7.2Hz, 3H), 1.04 (t, J = 7.2Hz, 3H)
(Isomer ratio 2) 8.92 (d, J = 2.4Hz, 1H), 8.65-8.55 (m, 1H), 8.05-7.95 (m, 1H), 7.87 (s, 1H), 7.42 (dd, J = 8.4 , 4.8Hz, 1H), 4.03 (t, J = 5.1Hz, 2H), 3.80 (q, J = 7.2Hz, 2H), 3.75-3.60 (m, 2H), 3.20 (s, 3H), 2.47 (q , J = 7.2Hz, 2H), 1.22 (t, J = 7.2Hz, 3H), 1.08 (t, J = 7.2Hz, 3H)
1-008;
(Isomer ratio 4) 9.08 (d, J = 2.4Hz, 1H), 8.68 (s, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.13 (ddd, J = 8.4,2.4,1.2 Hz, 1H), 7.42 (dd, J = 8.4,4.8Hz, 1H), 4.68 (t, J = 5.4Hz, 1H), 4.30-4.00 (m, 4H), 3.44 (s, 3H), 3.34 (s , 3H), 2.30-2.15 (m, 2H), 1.18 (t, J = 7.2Hz, 3H), 1.03 (t, J = 7.2Hz, 3H)
(Isomer ratio 1) 8.94 (d, J = 2.4Hz, 1H), 8.46 (dd, J = 4.8,1.2Hz, 1H), 8.00-7.90 (m, 1H), 7.42 (dd, J = 8.4,4.8 Hz, 1H), 7.34 (s, 1H), 4.30-3.80 (m, 5H), 3.50-3.30 (m, 3H), 3.22 (s, 3H), 2.30-2.15 (m, 2H), 1.30-1.20 ( m, 6H)
1-009;
9.00-8.70 (m, 2H), 8.61 (dd, J = 4.8,1.5Hz, 2H), 7.89 (ddd, J = 8.4,2.7,1.5Hz, 1H), 7.68 (s, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 7.32 (dd, J = 4.8,1.5Hz, 2H), 3.89 (s, 3H), 3.82 (q, J = 7.2Hz, 2H), 1.24 (t, J = 7.2 (Hz, 3H)
1-010;
(Isomer ratio 7) 8.92 (d, J = 2.7Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.09 (s, 1H), 8.02 (ddd, J = 8.7,2.7,1.2 Hz, 1H), 7.44 (dd, J = 8.7, 4.8Hz, 1H), 4.60-4.40 (m, 2H), 3.70 (s, 3H), 3.55 (s, 2H), 2.28 (t, J = 2.4Hz , 1H), 1,93 (s, 3H)
(Isomer ratio 1) 8.92 (d, J = 2.7Hz, 1H), 8.60 (dd, J = 4.8, 1.2Hz, 1H), 8.09 (s, 1H), 8.02 (ddd, J = 8.7, 2.7, 1.2 Hz, 1H), 7.44 (dd, J = 8.7,4.8Hz, 1H), 4.80-4.60 (m, 2H), 4.08 (s, 3H), 3.56 (s, 2H), 2.28 (t, J = 2.4Hz , 1H), 2.15 (s, 3H)
1-011;
8.98 (d, J = 2.7Hz, 1H), 8.58 (dd, J = 4.8,1.5Hz, 1H), 8.26 (s, 1H), 8.01 (ddd, J = 8.1,2.7,1.5Hz, 1H), 7.41 (dd, J = 8.1,4.8Hz, 1H), 4.60-4.40 (m, 2H), 4.08 (d, J = 12.3Hz, 1H), 3.95 (d, J = 12.3Hz, 1H), 3.78 (s, 3H), 2.59 (s, 3H), 2.28 (t, J = 2.4Hz, 1H)
1-012;
8.97 (d, J = 2.7Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.16 (s, 1H), 7.98 (ddd, J = 8.1,2.7,1.2Hz, 1H), 7.41 (dd, J = 8.1,4.8Hz, 1H), 4.60-4.40 (m, 4H), 3.82 (s, 3H), 2.88 (s, 3H), 2.29 (t, J = 2.4Hz, 1H)
1-014 (* 3);
8.92 (d, J = 2.7Hz, 1H), 8.60 (dd, J = 4.8Hz, 1.2Hz, 1H), 8.01 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.88 (s, 1H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 4.02 (t, J = 4.8Hz, 2H), 3.77 (q, J = 7.2Hz, 2H), 3.36 (t, J = 4.8Hz, 2H), 3.19 (s, 3H), 1.99 (s, 3H), 1.22 (t, J = 7.2Hz, 3H)
1-016;
(Isomer ratio 3) 9.08 (d, J = 2.7Hz, 1H), 8.66 (s, 1H), 8.65-8.55 (m, 1H), 8.20-8.10 (m, 1H), 7.50-7.40 (m, 1H ), 4.66 (t, J = 5.4Hz, 1H), 4.20-4.00 (m, 2H), 3.89 (d, J = 5.4Hz, 2H), 3.41 (s, 6H), 1.89 (s, 3H), 1.30 -1.15 (m, 3H)
(Isomer ratio 2) 8.94 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.20-8.10 (m, 1H), 7.89 (s, 1H), 7.50-7.40 (m, 1H ), 4.30-4.20 (m, 1H), 3.78 (q, J = 7.2Hz, 2H), 3.89 (d, J = 5.4Hz, 2H), 3.21 (s, 6H), 1.99 (s, 3H), 1.30 -1.15 (m, 3H)
1-017;
(Isomer ratio 3) 9.04 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.15-8.00 (m, 2H), 7.50-7.35 (m, 1H), 4.72 (s, 2H ), 3.79 (q, J = 7.2Hz, 2H), 1.98 (s, 3H), 1.20 (t, J = 7.2Hz, 3H)
(Isomer ratio 2) 8.98 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.15-8.00 (m, 1H), 7.98 (s, 1H), 7.50-7.35 (m, 1H ), 4.55 (s, 2H), 3.79 (q, J = 7.2Hz, 2H), 2.01 (s, 3H), 1.26 (t, J = 7.2Hz, 3H)
1-018;
8.70-8.60 (m, 1H), 8.57 (d, J = 3.0Hz, 1H), 8.52 (dd, J = 4.8,1.2Hz, 1H), 7.83 (s, 1H), 7.82 (ddd, J = 8.4, 3.0,1.2Hz, 1H), 7.75-7.60 (m, 2H), 7.34 (dd, J = 8.4,4.8Hz, 1H), 7.30-7.20 (m, 1H), 4.20-4.05 (m, 2H), 4.00 (s, 3H), 1.26 (t, J = 7.2Hz, 3H)
1-020 (* 3);
9.01 (d, J = 2.4Hz, 1H), 8.61 (dd, J = 4.8,1.2Hz, 1H), 8.08 (ddd, J = 8.4,2.4,1.2Hz, 1H), 8.01 (s, 1H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 4.85 (d, J = 11.8Hz, 1H), 4.78 (d, J = 11.8Hz, 1H), 4.00-3.75 (m, 2H), 2.35 (s, 3H), 2.03 (s.3H), 1.22 (t, J = 7.2Hz, 3H)
1-023;
(Isomer ratio 3) 8.93 (d, J = 2.7Hz, 1H), 8.61 (dd, J = 4.8,1.2Hz, 1H), 8.51 (s, 1H), 8.01 (ddd, J = 8.4,2.7,1.2 Hz, 1H), 7.41 (dd, J = 8.4, 4.8Hz, 1H), 4.10-3.35 (m, 3H), 2.80-2.65 (m, 2H), 2.11 (s, 3H), 1.45-1.10 (m, 9H)
(Isomer ratio 2) 9.01 (d, J = 2.7Hz, 1H), 8.61 (dd, J = 4.8,1.2Hz, 1H), 8.15 (s, 1H), 8.01 (ddd, J = 8.4,2.7,1.2 Hz, 1H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 4.10-3.35 (m, 3H), 2.49 (q, J = 7.2Hz, 2H), 2.11 (s, 3H), 1.45-1.10 (m, 9H)
1-024;
(Isomer ratio 27) 9.05-9.00 (m, 1H), 8.75-8.65 (m, 1H), 8.15 (s, 1H), 8.05-7.95 (m, 1H), 7.50-7.40 (m, 1H), 4.00 -3.75 (m, 2H), 3.00-2.60 (m, 4H), 2.20-2.00 (m, 6H), 1.30-1.15 (m, 3H)
(Isomer ratio 25) 9.05-9.00 (m, 1H), 8.75-8.65 (m, 1H), 8.25 (s, 1H), 8.05-7.95 (m, 1H), 7.50-7.40 (m, 1H), 4.00 -3.75 (m, 2H), 3.00-2.60 (m, 4H), 2.20-2.00 (m, 6H), 1.30-1.15 (m, 3H)
1-029;
(Isomer ratio 85) 8.89 (d, J = 2.7Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.03 (s, 1H), 8.00 (ddd, J = 8.1,2.7,1.2 Hz, 1H), 7.43 (dd, J = 8.1,4.8Hz, 1H), 4.09 (q, J = 7.2Hz, 1H), 3.75 (s, 3H), 3.32 (s, 3H), 1.90 (s, 3H ), 1.48 (d, J = 7.2Hz, 3H)
(Isomer ratio 15) 8.89 (d, J = 2.7Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.13 (s, 1H), 8.00 (ddd, J = 8.1,2.7,1.2 Hz, 1H), 7.43 (dd, J = 8.1, 4.8Hz, 1H), 4.38-4.27 (m, 1H), 3.97 (brs, 3H), 3.50 (brs, 3H), 2.20 (brs, 3H), 1.63 -1.55 (m, 3H)
1-030;
(Isomer ratio 5) 8.99-8.89 (m, 1H), 8.64-8.54 (m, 1H), 8.06-7.95 (m, 1H), 7.99 (s, 1H), 7.48-7.36 (m, 1H), 4.22 -4.00 (m, 1H), 3.76 (s, 3H), 3.32 (s, 3H), 2.57 (s, 3H), 1.52 (d, J = 7.5Hz, 3H)
(Isomer ratio 4) 8.99-8.89 (m, 1H), 8.64-8.54 (m, 1H), 8.18 (s, 1H), 8.06-7.95 (m, 1H), 7.48-7.36 (m, 1H), 4.22 -4.00 (m, 1H), 3.73 (s, 3H), 3.32 (s, 3H), 2.59 (s, 3H), 1.49 (d, J = 7.5Hz, 3H)
(Isomer ratio 1) 8.99-8.89 (m, 1H), 8.64-8.54 (m, 1H), 8.11 (s, 1H), 8.06-7.95 (m, 1H), 7.48-7.36 (m, 1H), 4.22 -4.00 (m, 1H), 3.84 (brs, 3H), 3.50 (brs, 3H), 2.65 (brs, 3H), 1.73-1.60 (m, 3H)
1-031;
(Isomer ratio 9) 8.95 (d, J = 2.7Hz, 1H), 8.58 (d, J = 4.8Hz, 1H), 8.11 (s, 1H), 7.99-7.93 (m, 1H), 7.41 (dd, J = 8.1, 4.8Hz, 1H), 4.64 (q, J = 7.2Hz, 1H), 3.76 (s, 3H), 3.32 (s, 3H), 2.94 (s, 3H), 1.76 (d, J = 7.2 (Hz, 3H)
(Isomer ratio 1) 8.95 (d, J = 2.7Hz, 1H), 8.58 (d, J = 4.8Hz, 1H), 8.09 (s, 1H), 7.99-7.93 (m, 1H), 7.41 (dd, J = 8.1, 4.8Hz, 1H), 4.91-4.81 (m, 1H), 4.09 (brs, 3H), 3.51 (brs, 3H), 3.03 (brs, 3H), 1.82-1.74 (m, 3H)
1-033;
(Isomer ratio 5) 8.97 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.24 (s, 1H), 8.00 (ddd, J = 8.4,2.4,1.2 Hz, 1H), 7.43 (dd, J = 8.4, 4.8Hz, 1H), 4.60-4.40 (m, 2H), 3.83 (s, 3H), 2.71 (s, 3H), 2.29 (t, J = 2.4Hz , 1H), 1.75-1.60 (m, 4H)
(Isomer ratio 1) 9.00 (d, J = 2.1Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.25 (s, 1H), 8.06-8.00 (m, 1H), 7.43 ( dd, J = 8.4, 4.8Hz, 1H), 4.60-4.40 (m, 2H), 3.83 (s, 3H), 3.11 (s, 3H), 2.26 (t, J = 2.1Hz, 1H), 1.75-1.60 (m, 4H)
1-034;
8.89 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 3.93 (q, J = 7.2Hz, 2H), 3.57 (s, 2H), 3.34 (s, 3H), 1.94 (s, 3H), 1.02 (t, J = 7.2Hz, 3H)
1-037;
(Isomer ratio 4) 8.96 (d, J = 2.7Hz, 1H), 8.57 (dd, J = 4.8,1.2Hz, 1H), 8.24 (s, 1H), 7.97 (ddd, J = 8.4,2.7,1.2 Hz, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 4.15-3.90 (m, 4H), 3.34 (s, 3H), 2.61 (s, 3H), 1.02 (t, J = 7.2Hz , 3H)
(Isomer ratio 1) 8.96 (d, J = 2.7Hz, 1H), 8.57 (dd, J = 4.8,1.2Hz, 1H), 8.24 (s, 1H), 7.97 (ddd, J = 8.4,2.7,1.2 Hz, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 4.15-3.90 (m, 2H), 3.48 (q, J = 7.2Hz, 2H), 3.34 (s, 3H), 2.61 (s , 3H), 1.20 (t, J = 7.2Hz, 3H)
1-042;
(Isomer ratio 3) 8.93 (d, J = 2.7Hz, 1H), 8.63-8.57 (m, 1H), 8.07-7.93 (m, 1H), 7.96 (s, 1H), 7.44 (dd, J = 8.1 , 4.8Hz, 1H), 4.19-4.03 (m, 1H), 3.93-3.61 (m, 2H), 3.75 (s, 3H), 2.57 (s, 3H), 1.51 (d, J = 7.2Hz, 3H) , 1.30-1.15 (m, 3H)
(Isomer ratio 2) 8.97 (d, J = 2.7Hz, 1H), 8.58-8.53 (m, 1H), 8.15 (s, 1H), 8.07-7.93 (m, 1H), 7.40 (dd, J = 8.1 , 4.8Hz, 1H), 4.19-4.03 (m, 1H), 3.93-3.61 (m, 2H), 3.72 (s, 3H), 2.58 (s, 3H), 1.49 (d, J = 7.2Hz, 3H) , 1.30-1.15 (m, 3H)
1-043;
8.91 (d, J = 2.7Hz, 1H), 8.58 (d, J = 4.8Hz, 1H), 8.03-7.95 (m, 2H), 7.42 (dd, J = 8.7,4.8Hz, 1H), 5.09 (brs , 2H), 3.70 (brs, 3H), 3.54 (brs, 2H), 3.48 (s, 3H), 1.93 (brs, 3H)
1-044;
(Isomer ratio 85) 8.95 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.07 (s, 1H), 8.02-7.94 (m, 1H), 7.41 ( dd, J = 8.1, 4.8Hz, 1H), 5.10 (brs, 2H), 4.47 (brs, 2H), 3.82 (brs, 3H), 3.49 (s, 3H), 2.85 (s, 3H)
(Isomer ratio 15) 9.00 (d, J = 2.1Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.41 (s, 1H), 8.09-7.94 (m, 1H), 7.41 ( dd, J = 8.1,4.8Hz, 1H), 5.10 (brs, 2H), 4.47 (brs, 2H), 3.82 (brs, 3H), 3.44 (s, 3H), 3.04 (s, 3H)
1-045;
8.90 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.07-7.93 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 5.14 (brs, 2H), 3.80-3.65 (m, 5H), 3.53 (brs, 2H), 1.93 (brs, 3H), 1.35-1.20 (m, 3H)
1-046;
(Isomer ratio 92) 9.00-8.90 (m, 1H), 8.67-8.57 (m, 1H), 8.16 (s, 1H), 8.00 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.45 (dd , J = 8.4, 4.8Hz, 1H), 4.63 (brs, 2H), 3.71 (brs, 3H), 3.55 (brs, 2H), 1.93 (brs, 3H)
(Isomer ratio 8)
9.00-8.90 (m, 1H), 8.67-8.57 (m, 1H), 8.39 (s, 1H), 8.00 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.45 (dd, J = 8.4,4.8 Hz, 1H), 4.68 (brs, 2H), 3.83 (s, 3H), 3.09 (s, 2H), 2.00 (s, 3H)
1-047;
8.88 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.03 (s, 1H), 7.97 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.42 (dd, J = 8.4,4.8Hz, 1H), 3.69 (d, J = 7.2Hz, 2H), 3.59 (s, 2H), 3.34 (s, 3H), 1.95 (s, 3H), 0.95-0.80 ( m, 1H), 0.40-0.25 (m, 2H), 0.15-0.05 (m, 2H)
1-048;
8.89 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8Hz, 1.2Hz, 1H), 8.03 (s, 1H), 7.98 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.42 (dd, J = 8.4,4.8Hz, 1H), 4.02 (t, J = 4.8Hz, 2H), 3.58 (s, 2H), 3.40-3.30 (m, 2H), 3.34 (s, 3H), 3.14 (s, 3H), 1.94 (s, 3H)
1-050;
8.91 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.11 (s, 1H), 7.99 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 4.96 (s, 2H), 3.55 (s, 2H), 3.36 (s, 3H), 1.94 (s, 3H), 1.90 (s, 3H)
1-051;
8.89 (d, J = 2.7Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 4.03 (t, J = 7.2Hz, 2H), 3.57 (s, 2H), 3.34 (s, 3H), 2.47 (t, J = 7.2Hz, 2H), 1.99 (s, 3H), 1.98 (s, 3H)
1-053;
8.97 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.5Hz, 1H), 8.25 (s, 1H), 8.00 (ddd, J = 8.4,2.4,1.5Hz, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 5.05-4.95 (m, 2H), 4.15-4.00 (m, 2H), 3.35 (s, 3H), 3.11 (s, 3H), 2.67 (s, 3H )
1-054;
(Isomer ratio 3) 8.85 (d, J = 2.4Hz, 1H), 8.65-8.57 (m, 1H), 8.04-7.90 (m, 1H), 7.83 (s, 1H), 7.43 (dd, J = 8.1 , 4.8Hz, 1H), 4.04 (s, 3H), 3.33 (s, 3H), 2.26 (s, 3H)
(Isomer ratio 2) 8.91 (d, J = 2.1Hz, 1H), 8.65-8.57 (m, 1H), 8.04-7.90 (m, 1H), 7.95 (s, 1H), 7.43 (dd, J = 8.1 , 4.8Hz, 1H), 3.82 (s, 3H), 3.32 (s, 3H), 2.36 (s, 3H)
1-055;
(Isomer ratio 50) 8.95 (d, J = 2.4Hz, 1H), 8.70-8.55 (m, 1H), 8.13 (s, 1H), 8.05-7.95 (m, 1H), 7.41 (dd, J = 8.4 , 4.8Hz, 1H), 5.00 (s, 2H), 4.54 (s, 2H), 3.40-3.30 (m, 3H), 3.11 (s, 3H), 2.97 (s, 3H)
(Isomer ratio 7) 9.00 (d, J = 3.0Hz, 1H), 8.70-8.55 (m, 1H), 8.46 (s, 1H), 8.05-7.95 (m, 1H), 7.41 (dd, J = 8.4 , 4.8Hz, 1H), 5.02 (s, 2H), 4.54 (s, 2H), 3.40-3.30 (m, 3H), 3.28 (s, 3H), 3.05 (s, 3H)
1-056;
8.93 (d, J = 2.7Hz, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.20 (s, 1H), 8.01 (ddd, J = 8.1,2.7,1.2Hz, 1H), 7.46 (dd, J = 8.1,4.8Hz, 1H), 4.75 (d, J = 17.4Hz, 1H), 4.52 (d, J = 17.4Hz, 1H), 4.12 (q, J = 7.2Hz, 1H), 3.76 (s, 3H), 1.92 (s, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-056 (* 3);
(Isomer ratio 81) 8.91 (d, J = 2.4Hz, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.36 (brs, 1H), 8.00 (ddd, J = 8.1,2.4,1.2 Hz, 1H), 7.46 (dd, J = 8.1, 4.8Hz, 1H), 4.95-4.32 (m, 2H), 3.88 (brs, 3H), 4.05-3.30 (m, 1H), 1.91 (brs, 3H) , 1.41 (d, J = 7.2Hz, 3H)
(Isomer ratio 19) 8.97 (d, J = 2.4Hz, 1H), 8.67-8.59 (m, 1H), 8.21 (brs, 1H), 8.06-7.96 (m, 1H), 7.50-7.40 (m, 1H ), 4.95-4.32 (m, 2H), 4.03 (brs, 3H), 4.05-3.30 (m, 1H), 2.18 (brs, 3H), 1.70-1.50 (m, 3H)
1-057 (* 3);
9.44 (brs, 1H), 8.98 (d, J = 2.4Hz, 1H), 8.71 (s, 1H), 8.55 (dd, J = 4.8,1.2Hz, 1H), 7.99 (ddd, J = 8.1,2.4, 1.2Hz, 1H), 7.39 (dd, J = 8.1, 4.8Hz, 1H), 4.17-4.01 (m, 1H), 4.09 (s, 3H), 2.10 (s, 3H), 1.52 (d, J = 7.2 (Hz, 3H)
1-058;
8.98-8.91 (m, 1H), 8.65-8.57 (m, 1H), 8.08 (s, 1H), 8.07-8.00 (m, 1H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 4.88 ( brs, 2H), 3.70 (s, 3H), 3.53 (s, 2H), 2.26 (s, 3H), 1.93 (s, 3H)
1-059;
8.89 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.1,2.4,1.2Hz, 1H), 7.94 (s, 1H), 7.43 (dd, J = 8.1,4.8Hz, 1H), 6.00-5.81 (m, 1H), 5.30-5.16 (m, 2H), 4.41-4.28 (m, 2H), 3.69 (s, 3H), 3.54 (s , 2H), 1.92 (s, 3H)
1-060;
8.90 (d, J = 2.7Hz, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 1H), 7.96 (s, 1H), 7.45 (dd, J = 8.4, 4.8Hz, 1H), 4.42 (sep, J = 6.3Hz, 1H), 3.38 (s, 3H), 1.15 (d, J = 6.3Hz, 6H)
1-065;
8.92 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 3.69 (s, 3H), 3.63 (d, J = 6.6Hz, 2H), 3.53 (s, 2H), 1.93 (s, 3H), 1.10-1.00 (m, 1H), 0.60-0.45 (m, 2H), 0.30-0.20 (m, 2H)
1-066;
(Isomer ratio 87) 8.94 (d, J = 2.1Hz, 1H), 8.65-8.55 (m, 1H), 8.10-7.95 (m, 1H), 7.89 (s, 1H), 7.44 (dd, J = 8.4 , 4.8Hz, 1H), 6.20-6.00 (m, 1H), 4.00-3.25 (m, 8H), 2.20-1.85 (m, 3H), 1.40-1.20 (m, 3H)
(Isomer ratio 13) 8.94 (d, J = 2.1Hz, 1H), 8.65-8.55 (m, 1H), 8.10-7.95 (m, 1H), 7.89 (s, 1H), 7.44 (dd, J = 8.4 , 4.8Hz, 1H), 5.80-5.60 (m, 1H), 4.00-3.25 (m, 8H), 2.20-1.85 (m, 3H), 1.40-1.20 (m, 3H)
1-067;
8.75-8.65 (m, 1H), 8.60-8.50 (m, 1H), 7.90-7.70 (m, 1H), 7.50-7.30 (m, 7H), 5.00-4.80 (m, 2H), 3.70-3.55 (m , 5H), 1.95-1.85 (m, 3H)
1-068;
(Isomer ratio 5) 8.94 (d, J = 2.7Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.42 (dd, J = 8.4,4.8 Hz, 1H), 3.99 (s, 3H), 3.85 (s, 3H), 3.64 (s, 2H), 2.14 (s, 3H)
(Isomer ratio 1) 9.00-8.90 (m, 1H), 8.60-8.50 (m, 1H), 8.05-7.95 (m, 2H), 7.40-7.35 (m, 1H), 3.99 (s, 3H), 3.85 (s, 3H), 3.64 (s, 2H), 2.14 (s, 3H)
1-069;
8.74 (d, J = 2.4Hz, 1H), 8.55 (dd, J = 4.8,1.2Hz, 1H), 7.99 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.63 (s, 1H), 7.50 -7.20 (m, 5H), 5.10 (s, 2H), 3.69 (s, 3H), 3.57 (s, 2H), 1.92 (s, 3H)
1-070;
8.77 (d, J = 2.7Hz, 1H), 8.55 (dd, J = 4.8,1.2Hz, 1H), 7.90 (ddd, J = 8.1,2.7,1.2Hz, 1H), 7.59 (s, 1H), 7.39 (dd, J = 8.1,4.8Hz, 1H), 7.35-7.15 (m, 4H), 4.89 (brs, 2H), 3.69 (s, 3H), 3.57 (s, 2H), 1.93 (s, 3H)
1-071;
8.77 (d, J = 2.7Hz, 1H), 8.56 (dd, J = 4.8,1.2Hz, 1H), 7.87 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.56 (s, 1H), 7.50 -7.20 (m, 5H), 4.88 (brs, 2H), 3.68 (s, 3H), 3.56 (s, 2H), 1.90 (s, 3H)
1-073;
8.90 (d, J = 2.7Hz, 1H), 8.61 (dd, J = 4.8,1.2Hz, 1H), 8.10-7.90 (m, 2H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 5.80 -5.60 (brs, 2H), 3.90-3.60 (brs, 3H), 3.57 (s, 2H), 2.11 (s, 3H), 2.05-1.85 (brs, 3H)
1-074;
(Isomer ratio 5) 8.97 (d, J = 2.7Hz, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.17 (s, 1H), 8.00 (ddd, J = 8.1,2.7,1.2 Hz, 1H), 7.44 (dd, J = 8.1, 4.8Hz, 1H), 5.90-5.70 (m, 1H), 4.20-3.40 (m, 5H), 2.20-1.85 (m, 3H), 1.35-1.10 ( m, 3H)
(Isomer ratio 1) 9.01 (d, J = 2.7Hz, 1H), 8.84 (s, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.1,2.7,1.2 Hz, 1H), 7.44 (dd, J = 8.1, 4.8Hz, 1H), 5.90-5.70 (m, 1H), 4.20-3.40 (m, 5H), 2.20-1.85 (m, 3H), 1.35-1.10 ( m, 3H)
1-075;
(Isomer ratio 1) 9.05-8.90 (m, 1H), 8.65-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.41 (dd, J = 8.4, 4.8Hz, 1H), 6.10-5.90 (m, 1H), 4.20-3.90 (m, 2H), 3.79 (s, 3H), 3.60-3.45 (m, 3H), 2.67 (s, 3H), 1.40-1.20 (m, 3H)
(Isomer ratio 1) 9.05-8.90 (m, 1H), 8.65-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.41 (dd, J = 8.4, 4.8Hz, 1H), 6.10-5.90 (m, 1H), 4.20-3.90 (m, 2H), 3.79 (s, 3H), 3.60-3.45 (m, 3H), 2.44 (s, 3H), 1.40-1.20 (m, 3H)
1-077;
8.91 (d, J = 2.7Hz, 1H), 8.59 (d, J = 4.8Hz, 1H), 8.03 (s, 1H), 8.02-7.98 (m, 1H), 7.43 (dd, J = 8.4,4.8Hz , 1H), 5.20 (d, J = 9.6Hz, 1H), 4.97 (d, J = 9.6Hz, 1H), 4.20-4.00 (m, 1H), 3.76 (s, 3H), 3.49 (s, 3H) , 1.94 (s, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-077 (* 3);
(Isomer ratio 5) 8.89 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.30-7.95 (m, 2H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 5.50-4.70 (m, 2H), 3.92 (brs, 3H), 3.80-3.60 (m, 1H), 3.46 (s, 3H), 1.90 (brs, 3H), 1.50-1.30 (m, 3H)
(Isomer ratio 1) 8.94 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.30-7.95 (m, 2H), 7.42 (dd, J = 8.4,4.8Hz, 1H), 5.50-4.70 (m, 2H), 3.95 (s, 3H), 3.55-3.45 (m, 1H), 3.39 (s, 3H), 1.90 (brs, 3H), 1.50-1.30 (m, 3H)
1-079;
8.96 (d, J = 2.7Hz, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.14 (s, 1H), 8.02 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.46 (dd, J = 8.4,4.8Hz, 1H), 5.85-5.60 (m, 1H), 4.20-3.60 (m, 4H), 1.94 (brs, 3H), 1.65-1.45 (m, 3H), 1.13 (d , J = 6.0Hz, 3H)
1-080;
(Isomer ratio 1) 9.00-8.80 (m, 1H), 8.70-8.55 (m, 1H), 8.10-7.95 (m, 2H), 7.55-7.40 (m, 1H), 3.87 (s, 3H), 3.30 (s, 3H), 2.90-2.50 (m, 4H), 2.05 (s, 3H)
(Isomer ratio 1) 9.00-8.80 (m, 1H), 8.70-8.55 (m, 1H), 8.10-7.95 (m, 2H), 7.55-7.40 (m, 1H), 3.69 (brs, 3H), 3.32 (brs, 3H), 2.90-2.50 (m, 4H), 2.12 (brs, 3H)
1-081;
8.82 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 7.95 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.85 (s, 1H), 7.45 -7.30 (m, 6H), 5.45-5.25 (m, 1H), 5.20-5.05 (m, 1H), 4.75 (s, 2H), 4.10-4.00 (m, 1H), 3.75 (s, 3H), 1.94 (brs, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-082;
(Isomer ratio 3) 9.05-8.95 (m, 1H), 8.70-8.55 (m, 1H), 8.21 (s, 1H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H), 4.90 -4.45 (m, 2H), 4.30-4.10 (m, 1H), 3.79 (s, 3H), 2.56 (s, 3H), 1.65-1.50 (m, 3H)
(Isomer ratio 2) 9.05-8.95 (m, 1H), 8.70-8.55 (m, 1H), 8.35 (s, 1H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H), 4.90 -4.45 (m, 2H), 4.30-4.10 (m, 1H), 3.78 (s, 3H), 2.60 (s, 3H), 1.65-1.50 (m, 3H)
1-084;
8.96 (d, J = 2.7Hz, 1H), 8.70-8.55 (m, 1H), 8.09 (s, 1H), 8.05-7.95 (m, 1H), 7.43 (dd, J = 8.4,4.8Hz, 1H) , 5.68 (brs, 2H), 4.47 (brs, 2H), 3.84 (brs, 3H), 2.89 (brs, 3H), 2.10 (s, 3H)
1-085;
(Isomer ratio 4) 9.00-8.90 (m, 1H), 8.65-8.50 (m, 1H), 8.10-7.95 (m, 2H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 4.35-4.15 (m, 3H), 3.97 (s, 3H), 3.80-3.60 (m, 1H), 2.19 (s, 3H), 1.55-1.50 (m, 3H), 1.35-1.25 (m, 3H), 1.13 (d , J = 6.0Hz, 3H)
(Isomer ratio 1) 9.00-8.90 (m, 1H), 8.65-8.50 (m, 1H), 8.10-7.95 (m, 2H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 4.35-4.15 (m, 3H), 3.92 (s, 3H), 3.80-3.60 (m, 1H), 2.15 (s, 3H), 1.55-1.50 (m, 3H), 1.35-1.25 (m, 3H), 1.13 (d , J = 6.0Hz, 3H)
1-086;
8.88 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 5.90 -5.50 (m, 2H), 4.25-3.70 (m, 4H), 1.95 (brs, 3H), 1.53 (d, J = 7.2Hz, 3H), 1.21 (s, 9H)
1-087;
8.90 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.10-7.95 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 5.80 -5.60 (m, 2H), 4.12 (q, J = 7.2Hz, 1H), 3.77 (brs, 3H), 2.10 (s, 3H), 1.93 (brs, 3H), 1.53 (d, J = 7.2Hz, 3H)
1-088;
(Isomer ratio 20) 9.00-8.85 (m, 1H), 8.65-8.50 (m, 1H), 8.09 (s, 1H), 8.05-7.90 (m, 1H), 7.50-7.35 (m, 1H), 5.80 -5.35 (m, 2H), 4.67 (q, J = 7.2Hz, 1H), 3.81 (s, 3H), 2.92 (s, 3H), 2.10 (s, 3H), 1.77 (d, J = 7.2Hz, 3H)
(Isomer ratio 13) 9.00-8.85 (m, 1H), 8.65-8.50 (m, 1H), 8.12 (s, 1H), 8.05-7.90 (m, 1H), 7.50-7.35 (m, 1H), 5.60 -4.90 (m, 2H), 4.76 (q, J = 7.2Hz, 1H), 3.98 (s, 3H), 2.95 (s, 3H), 2.10 (s, 3H), 1.76 (d, J = 7.2Hz, 3H)
1-089;
8.89 (d, J = 2.7Hz, 1H), 8.56 (d, J = 4.8,1.2Hz, 1H), 8.18 (s, 1H), 8.01 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 5.40-4.95 (m, 2H), 4.09 (q, J = 7.2Hz, 1H), 3.90-3.80 (m, 2H), 3.75 (s, 3H), 3.65-3.55 (m, 2H), 3.39 (s, 3H), 1.93 (s, 3H), 1.51 (d, J = 7.2Hz, 3H)
1-090;
(Isomer ratio 4) 8.94 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8, 1.2Hz, 1H), 8.10-7.95 (m, 2H), 7.43 (dd, J = 8.4, 4.8 Hz, 1H), 5.40-4.80 (m, 2H), 4.30-3.90 (m, 1H), 3.77 (s, 3H), 3.47 (s, 3H), 2.57 (s, 3H), 1.56 (d, J = (7.2Hz, 3H)
(Isomer ratio 1) 8.96 (d, J = 2.4Hz, 1H), 8.56 (dd, J = 4.8,1.2Hz, 1H), 8.16 (s, 1H), 8.10-7.95 (m, 1H), 7.60- 7.35 (m, 1H), 5.40-4.80 (m, 2H), 4.30-3.90 (m, 4H), 3.50 (s, 3H), 2.57 (s, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-090 (* 3);
(Isomer ratio 6) 9.00-8.85 (m, 1H), 8.60-8.55 (m, 1H), 8.50-7.95 (m, 2H), 7.50-7.35 (m, 1H), 5.35-4.60 (m, 2H) , 3.91 (s, 3H), 3.80-3.40 (m, 4H), 2.63 (brs, 3H), 1.60-1.30 (m, 3H)
(Isomer ratio 1) 9.00-8.85 (m, 1H), 8.60-8.55 (m, 1H), 8.50-7.95 (m, 2H), 7.50-7.35 (m, 1H), 5.35-4.60 (m, 2H) , 4.01 (s, 3H), 3.80-3.30 (m, 4H), 2.55 (brs, 3H), 1.60-1.30 (m, 3H)
1-091;
8.96 (d, J = 2.4Hz, 1H), 8.57 (dd, J = 4.8,1.2Hz, 1H), 8.10 (s, 1H), 8.05-7.90 (m, 1H), 7.41 (dd, J = 8.4, 4.8Hz, 1H), 5.40-5.20 (m, 1H), 4.95-4.75 (m, 1H), 4.69 (q, J = 7.2Hz, 1H), 3.81 (s, 3H), 3.49 (s, 3H), 2.90 (s, 3H), 1.77 (d, J = 7.2Hz, 3H)
1-092;
(Isomer ratio 4) 8.86 (d, J = 2.7Hz, 1H), 8.65-8.50 (m, 1H), 8.05-7.90 (m, 1H), 7.79 (s, 1H), 7.50-7.20 (m, 6H ), 5.55-4.60 (m, 4H), 4.30-4.00 (m, 1H), 3.77 (s, 3H), 2.60 (s, 3H), 1.54 (d, J = 7.2Hz, 3H)
(Isomer ratio 3) 8.90 (d, J = 2.7Hz, 1H), 8.65-8.50 (m, 1H), 8.07 (s, 1H), 8.05-7.90 (m, 1H), 7.50-7.20 (m, 6H ), 5.55-4.60 (m, 4H), 4.30-4.00 (m, 1H), 3.77 (s, 3H), 2.58 (s, 3H), 1.54 (d, J = 7.2Hz, 3H)
1-093;
8.90 (d, J = 2.4Hz, 1H), 8.56 (dd, J = 4.8,1.2Hz, 1H), 8.02 (s, 1H), 7.92 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.45 -7.25 (m, 6H), 5.60-5.45 (m, 1H), 5.10-4.85 (m, 1H), 4.85-4.65 (m, 3H), 3.81 (s, 3H), 2.93 (s, 3H), 1.79 (d, J = 7.2Hz, 3H)
1-094;
8.90 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.10-7.90 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 5.35 -5.15 (m, 1H), 5.10-4.90 (m, 1H), 4.09 (q, J = 7.2Hz, 1H), 3.85-3.65 (m, 5H), 1.93 (brs, 3H), 1.51 (d, J = 7.2Hz, 3H), 1.05-0.90 (m, 2H), 0.03 (s, 9H)
1-095;
8.90-8.80 (m, 1H), 8.60-8.50 (m, 1H), 8.15-7.90 (m, 4H), 7.65-7.30 (m, 4H), 6.10-5.60 (m, 2H), 4.25-4.00 (m , 1H), 3.77 (brs, 3H), 1.95 (brs, 3H), 1.55 (d, J = 7.2Hz, 3H)
1-096;
8.89 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.10-7.95 (m, 2H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 5.90 -5.55 (m, 2H), 4.25-3.85 (m, 1H), 3.76 (s, 3H), 2.34 (t, J = 7.2Hz, 2H), 1.93 (brs, 3H), 1.75-1.60 (m, 2H ), 1.53 (d, J = 7.2Hz, 3H), 0.94 (t, J = 7.2Hz, 3H)
1-098;
8.96 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.07 (s, 1H), 8.05-7.90 (m, 1H), 7.41 (dd, J = 8.4, 4.8Hz, 1H), 5.45-5.25 (m, 1H), 5.05-4.80 (m, 1H), 4.68 (q, J = 7.2Hz, 1H), 3.81 (s, 3H), 3.85-3.65 (m, 2H ), 2.90 (s, 3H), 1.76 (d, J = 7.2Hz, 3H), 1.24 (t, J = 7.2Hz, 3H)
1-099;
8.93 (d, J = 2.7Hz, 1H), 8.61 (dd, J = 4.8,1.2Hz, 1H), 8.16 (s, 1H), 8.01 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.43 (dd, J = 8.4,4.8Hz, 1H), 4.11 (q, J = 7.2Hz, 1H), 3.86 (s, 3H), 3.54 (s, 3H), 1.99 (s, 3H), 1.60-1.50 ( m, 3H)
1-100;
8.90 (d, J = 2.7Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.17 (s, 1H), 7.98 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.45 -7.35 (m, 1H), 6.25-5.90 (m, 1H), 5.65-5.25 (m, 1H), 4.60-4.05 (m, 3H), 3.76 (s, 3H), 1.97 (s, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-102;
8.93 (d, J = 2.7Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 1H), 8.03 (s, 1H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 4.21 (qJ = 7.2Hz, 1H), 3.97 (s, 3H), 3.83 (s, 3H), 2.18 (s, 3H), 1.65-1.50 (m, 3H)
1-103;
8.97 (d, J = 2.4Hz, 1H), 8.69 (s, 1H), 8.57 (brs, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 7.98 (ddd, J = 8.4,2.4, 1.2Hz, 1H), 7.38 (dd, J = 8.4, 4.8Hz, 1H), 4.42 (q, J = 7.2Hz, 1H), 4.09 (s, 3H), 2.65-2.50 (m, 2H), 1.62 ( d, J = 7.2Hz, 3H), 1.27 (t, J = 7.2Hz, 3H)
1-104;
(Isomer ratio 95) 8.92 (d, J = 2.7Hz, 1H), 8.62 (dd, J = 4.8, 1.2Hz, 1H), 8.17 (s, 1H), 8.00 (ddd, J = 8.4, 2.7, 1.2 Hz, 1H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 4.72 (d, J = 17.2Hz, 1H), 4.54 (d, J = 17.2Hz, 1H), 4.23-3.98 (m, 1H ), 3.75 (s, 3H), 2.41-2.25 (m, 2H), 1.51 (d, J = 7.5Hz, 3H), 1.14 (t, J = 7.2Hz, 3H)
(Isomer ratio 5) 8.97 (s, 1H), 8.92 (d, J = 2.7Hz, 1H), 8.62 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.4,2.7,1.2 Hz, 1H), 7.44 (dd, J = 8.4,4.8Hz, 1H), 4.95-4.85 (m, 1H), 4.63-4.49 (m, 1H), 4.23-3.98 (m, 1H), 3.75 (s, 3H), 2.77-2.41 (m, 2H), 1.42 (d, J = 7.2Hz, 3H), 1.14 (t, J = 7.2Hz, 3H)
1-105 (* 3);
(Isomer ratio 2) 9.00-8.80 (m, 1H), 8.65-8.55 (m, 1H), 8.28 (brs, 1H), 8.05-7.95 (m, 1H), 7.55-7.35 (m, 1H), 6.00 -5.55 (m, 2H), 4.00-3.60 (m, 7H), 1.92 (brs, 3H), 1.41 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 9.00-8.80 (m, 1H), 8.65-8.55 (m, 1H), 8.09 (s, 1H), 8.05-7.95 (m, 1H), 7.55-7.35 (m, 1H), 6.00 -5.35 (m, 2H), 4.00-3.60 (m, 7H), 2.15 (brs, 3H), 1.60-1.40 (brs, 3H)
1-112;
(Isomer ratio 50) 8.87 (d, J = 2.4Hz, 1H), 8.58 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.42 (dd, J = 8.4,4.8 Hz, 1H), 5.85-5.60 (m, 2H), 4.25-3.60 (m, 4H), 3.40-3.20 (m, 4H), 1.94 (brs, 3H), 1.62 (d, J = 7.2Hz, 3H) , 1.20-1.00 (m, 6H)
(Isomer ratio 6) 8.95 (d, J = 2.4Hz, 1H), 8.60-8.50 (m, 1H), 8.24 (s, 1H), 8.05-7.95 (m, 1H), 7.45-7.35 (m, 1H ), 5.85-5.60 (m, 2H), 4.25-3.60 (m, 4H), 3.40-3.20 (m, 4H), 1.94 (brs, 3H), 1.62 (d, J = 7.2Hz, 3H), 1.20- 1.00 (m, 6H)
1-113;
(Isomer ratio 83) 8.94 (d, J = 2.7Hz, 1H), 8.65-8.55 (m, 1H), 8.10-8.00 (m, 1H), 7.91 (s, 1H), 7.50-7.40 (m, 1H ), 6.15-5.95 (m, 1H), 4.10-3.90 (m, 1H), 3.75 (s, 3H), 3.53 (s, 3H), 1.86 (brs, 3H), 1.55-1.20 (m, 6H)
(Isomer ratio 10) 9.00-8.90 (m, 1H), 8.65-8.55 (m, 1H), 8.10-8.00 (m, 1H), 7.89 (s, 1H), 7.50-7.40 (m, 1H), 5.55 -5.35 (m, 1H), 4.10-3.90 (m, 1H), 3.55 (s, 3H), 3.53 (s, 3H), 2.08 (brs, 3H), 1.55-1.20 (m, 6H)
1-114;
8.93 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.11 (s, 1H), 8.03 (ddd, J = 8.1,2.4,1.2Hz, 1H), 7.43 (dd, J = 8.1,4.8Hz, 1H), 5.14-4.98 (m, 1H), 4.70-4.60 (m, 1H), 4.10 (q, J = 7.2Hz, 1H), 3.75 (s, 3H), 2.26 (s, 3H), 1.93 (s, 3H), 1.51 (d, J = 7.2Hz, 3H)
1-115;
(Isomer ratio 83) 8.92 (d, J = 2.4Hz, 1H), 8.60 (d, J = 4.5Hz, 1H), 8.06-7.99 (m, 1H), 7.86 (s, 1H), 7.44 (dd, J = 8.1, 4.5Hz, 1H), 6.22-6.02 (m, 1H), 4.35-3.55 (m, 3H), 3.74 (s, 3H), 2.30-1.80 (m, 3H), 1.68-1.10 (m, 9H)
(Isomer ratio 17) 8.92 (d, J = 2.4Hz, 1H), 8.60 (d, J = 4.5Hz, 1H), 8.06-7.99 (m, 1H), 7.86 (s, 1H), 7.44 (dd, J = 8.1,4.5Hz, 1H), 5.62-5.48 (m, 1H), 4.35-3.55 (m, 3H), 3.74 (s, 3H), 2.30-1.80 (m, 3H), 1.68-1.10 (m, 9H)
1-116 (* 3)
9.12 (brs, 1H), 8.99 (d, J = 2.4Hz, 1H), 8.62 (s, 1H), 8.50 (dd, J = 4.8,1.2Hz, 1H), 7.98 (ddd, J = 8.4,2.4, 1.2Hz, 1H), 7.36 (dd, J = 8.4, 4.8Hz, 1H), 4.08 (s, 3H), 4.05 (q, J = 7.2Hz, 1H), 2.35 (s, 3H), 2.08 (s, 3H), 1.53 (d, J = 7.2Hz, 3H)
1-118;
8.92 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.11 (s, 1H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H) , 5.90-5.70 (m, 1H), 5.65-5.40 (m, 1H), 4.40-4.20 (m, 3H), 3.75 (brs, 3H), 3.65-3.50 (m, 2H), 3.36 (s, 3H) , 1.92 (brs, 3H), 1.53 (d, J = 7.2Hz, 3H)
1-119;
8.96 (d, J = 2.4Hz, 1H), 8.59 (dd, J = 4.8,1.2Hz, 1H), 8.14 (s, 1H), 8.05-7.90 (m, 1H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 6.00-5.75 (m, 1H), 5.65-5.35 (m, 1H), 4.80-4.55 (m, 1H), 4.29 (t, J = 4.5Hz, 2H), 3.81 (s, 3H ), 3.60 (t, J = 4.5Hz, 2H), 3.36 (s, 3H), 2.93 (s, 3H), 1.76 (d, J = 7.2Hz, 3H)
1-120;
(Isomer ratio 87) 9.00-8.95 (m, 1H), 8.61-8.58 (m, 1H), 8.14 (s, 1H), 8.12-8.02 (m, 1H), 7.44 (dd, J = 8.1,4.8Hz , 1H), 6.53 (s, 1H), 3.61 (s, 3H), 3.41 (s, 3H), 3.15 (q, J = 7.2Hz, 1H), 2.10 (s, 3H), 1.45 (d, J = (7.2Hz, 3H)
(Isomer ratio 13) 9.00-8.95 (m, 1H), 8.61-8.58 (m, 1H), 8.14 (s, 1H), 8.12-8.02 (m, 1H), 7.44 (dd, J = 8.1,4.8Hz , 1H), 6.45 (s, 1H), 3.56 (s, 3H), 3.43 (s, 3H), 3.24 (q, J = 7.2Hz, 1H), 2.25 (s, 3H), 1.38 (d, J = (7.2Hz, 3H)
1-122;
(Isomer ratio 93) 8.98 (d, J = 2.7Hz, 1H), 8.69 (s, 1H), 8.64 (brs, 1H), 8.55 (dd, J = 4.8, 1.2Hz, 1H), 7.98 (ddd, J = 8.4, 2.7, 1.2Hz, 1H), 7.39 (dd, J = 8.4, 4.8Hz, 1H), 4.07 (s, 3H), 3.82 (d, J = 10.8Hz, 1H), 2.58-2.40 (m , 1H), 2.13 (s, 3H), 1.44 (d, J = 6.6Hz, 3H), 0.90 (d, J = 6.6Hz, 3H)
(Isomer ratio 7) 9.51 (brs, 1H), 8.98 (d, J = 2.7Hz, 1H), 8.71 (s, 1H), 8.55 (dd, J = 4.8, 1.2Hz, 1H), 7.98 (ddd, J = 8.4, 2.7, 1.2Hz, 1H), 7.39 (dd, J = 8.4, 4.8Hz, 1H), 4.08 (s, 3H), 3.40 (d, J = 10.5Hz, 1H), 2.58-2.40 (m , 1H), 2.09 (s, 3H), 1.44 (d, J = 6.6Hz, 3H), 0.90 (d, J = 6.6Hz, 3H)
1-128;
8.97 (d, J = 2.4Hz, 1H), 8.57 (dd, J = 4.8,1.2Hz, 1H), 8.10-7.95 (m, 1H), 7.90-7.80 (m, 1H), 7.42 (dd, J = 8.4, 4.8Hz, 1H), 7.30-7.20 (m, 1H), 5.85-5.45 (m, 2H), 4.00-3.80 (m, 7H), 2.25-1.80 (m, 3H), 1.60-1.50 (brs, 3H)
1-129;
8.98 (d, J = 2.7Hz, 1H), 8.65-8.50 (m, 1H), 8.20-7.70 (m, 2H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 7.30-7.20 (m, 1H), 5.80-5.40 (m, 2H), 5.00-4.60 (m, 1H), 3.81 (s, 3H), 3.80 (s, 3H), 3.25-2.60 (m, 3H), 1.76 (d, J = (7.2Hz, 3H)
1-132;
(Isomer ratio 3) 8.91 (d, J = 2.4Hz, 1H), 8.60 (dd, J = 4.8,1.2Hz, 1H), 8.09 (s, 1H), 8.01 (ddd, J = 8.4,2.4,1.2 Hz, 1H), 7.43 (dd, J = 8.4, 4.8Hz, 1H), 5.90-5.35 (m, 2H), 3.90-3.50 (m, 7H), 2.40-2.20 (m, 1H), 1.87 (brs, 3H), 1.14 (d, J = 6.0Hz, 6H)
(Isomer ratio 1) 9.00-8.85 (m, 1H), 8.65-8.50 (m, 1H), 8.12 (s, 1H), 8.05-7.90 (m, 1H), 7.43 (dd, J = 8.4,4.8Hz , 1H), 5.90-5.35 (m, 2H), 3.90-3.50 (m, 7H), 2.40-2.20 (m, 1H), 1.87 (brs, 3H), 0.98 (d, J = 6.0Hz, 6H)
1-142;
8.95-8.85 (m, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 1H), 7.95 (s, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 5.70-5.50 (m, 2H), 4.30-3.90 (m, 1H), 3.75 (brs, 3H), 2.45-2.20 (m, 5H), 2.10 (s, 3H), 1.55-1.45 (m, 3H), 1.20-1.05 (m, 3H)
1-143;
8.91 (d, J = 2.4Hz, 1H), 8.53 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 2H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 5.85 -5.45 (m, 2H), 4.25-4.10 (m, 1H), 3.79 (s, 3H), 3.75 (brs, 3H), 2.40-2.15 (m, 5H), 1.60-1.40 (m, 3H), 1.25 -1.00 (m, 3H)
1-144;
(Isomer ratio 5) 8.88 (d, J = 2.4Hz, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 8.20-7.95 (m, 2H), 7.40 (dd, J = 8.4,4.8 Hz, 1H), 5.30-4.75 (m, 2H), 4.05-3.80 (m, 4H), 3.47 (s, 3H), 2.31 (s, 3H), 1.81 (s, 3H), 1.38 (d, J = (7.2Hz, 3H)
(Isomer ratio 1) 8.92 (d, J = 2.4Hz, 1H), 8.50 (dd, J = 4.8, 1.2Hz, 1H), 8.20-7.95 (m, 2H), 7.45-7.30 (m, 1H), 5.30-4.75 (m, 2H), 4.05-3.80 (m, 4H), 3.38 (s, 3H), 2.27 (s, 3H), 2.16 (s, 3H), 1.58 (d, J = 7.2Hz, 3H)
1-145;
8.90 (d, J = 2.7Hz, 1H), 8.60-8.45 (m, 2H), 8.15-8.00 (m, 1H), 7.38 (dd, J = 8.4,4.8Hz, 1H), 4.59 (q, J = 7.2Hz, 1H), 4.47 (q, J = 7.2Hz, 1H), 4.14 (s, 3H), 4.00 (s, 3H), 2.75-2.55 (m, 2H), 2.46 (s, 3H), 2.12 ( s, 3H), 1.69 (d, J = 7.2Hz, 3H), 1.59 (d, J = 7.2Hz, 3H), 1.28 (t, J = 7.2Hz, 3H)
1-148;
(Isomer ratio 2) 8.89 (d, J = 2.7Hz, 1H) 8.55 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.95 (m, 1H), 7.85 (s, 1H), 7.45-7.35 (m, 1H), 4.20-4.00 (m, 1H), 3.78 (s, 3H), 3.29 (s, 3H), 2.57 (s, 3H), 2.31 (s, 3H), 2.30-1.70 (m, 2H ), 0.90 (t, J = 7.2Hz, 3H)
(Isomer ratio 1) 8.96 (d, J = 2.7Hz, 1H) 8.50 (dd, J = 4.8,1.2Hz, 1H), 8.08 (s, 1H), 8.05-7.95 (m, 1H), 7.45-7.35 (m, 1H), 4.20-4.00 (m, 1H), 3.71 (s, 3H), 3.28 (s, 3H), 2.49 (s, 3H), 2.33 (s, 3H), 2.30-1.70 (m, 2H ), 1.03 (t, J = 7.2Hz, 3H)
1-149;
(Isomer ratio 25) 8.95 (d, J = 2.7Hz, 1H) 8.52 (dd, J = 4.8,1.2Hz, 1H), 8.02 (s, 1H), 8.05-7.90 (m, 1H), 7.37 (dd , J = 8.4,4.8Hz, 1H), 4.57 (q, J = 5.1Hz, 1H), 3.73 (s, 3H), 3.29 (s, 3H), 2.81 (s, 3H), 2.33 (s, 3H) , 2.30-2.10 (m, 2H), 1.06 (t, J = 7.2Hz, 3H)
(Isomer ratio 3) 9.00-8.90 (m, 1H), 8.60-8.45 (m, 1H), 8.10-7.90 (m, 2H), 7.45-7.30 (m, 1H), 4.80-4.50 (m, 1H) , 4.07 (s, 3H), 3.50 (s, 3H), 3.01 (s, 3H), 2.45-2.10 (m, 5H), 1.15-1.00 (m, 3H)
1-153;
8.81 (d, J = 2.7Hz, 1H), 8.60-8.55 (m, 3H), 7.95-7.85 (m, 1H), 7.33 (s, 1H), 7.45-7.35 (m, 1H), 7.30-7.20 ( m, 2H), 5.07 (d, J = 15.0Hz, 1H), 4.79 (d, J = 15.0Hz, 1H), 4.19 (q, J = 7.2Hz, 1H), 3.77 (s, 3H), 2.45- 2.30 (m, 2H), 1.56 (d, J = 7.2Hz, 3H), 1.16 (t, J = 7.5Hz, 3H)
1-154;
(Isomer ratio 8) 9.02-8.96 (m, 1H), 8.57 (s, 1H), 8.56-8.46 (m, 1H), 8.30 (brs, 1H), 8.03-7.96 (m, 1H), 7.45-7.35 (m, 1H), 4.45-4.25 (m, 1H), 4.20-4.10 (m, 3H), 2.53 (s, 3H), 2.45-2.15 (m, 5H), 1.20-0.95 (m, 3H)
(Isomer ratio 7) 9.76 (brs, 1H), 9.02-8.96 (m, 1H), 8.57 (s, 1H), 8.56-8.46 (m, 1H), 8.03-7.96 (m, 1H), 7.45-7.35 (m, 1H), 4.45-4.25 (m, 1H), 4.20-4.10 (m, 3H), 2.68 (s, 3H), 2.45-2.15 (m, 5H), 1.20-0.95 (m, 3H)
1-155;
8.98 (d, J = 2.4Hz, 1H), 8.53 (s, 1H), 8.51 (dd, J = 4.8,1.2Hz, 1H), 8.39 (brs, 1H), 8.00 (ddd, J = 8.1,2.4, 1.2Hz, 1H), 7.38 (dd, J = 8.1, 4.8Hz, 1H), 4.89 (dd, J = 10.5, 4.8Hz, 1H), 4.17 (s, 3H), 3.11 (s, 3H), 2.55- 2.40 (m, 1H), 2.38 (s, 3H), 2.36-2.20 (m, 1H), 1.03 (t, J = 7.5Hz, 3H)
1-156;
8.98 (d, J = 2.4Hz, 1H), 8.60 (s, 1H), 8.49 (dd, J = 4.5,1.2Hz, 1H), 8.37 (brs, 1H), 7.98 (ddd, J = 8.1,2.4, 1.2Hz, 1H), 7.36 (dd, J = 8.1, 4.5Hz, 1H), 4.48 (dd, J = 9.0, 6.6Hz, 1H), 4.10-4.40 (m, 4H), 3.80 (dd, J = 9.0 , 6.6Hz, 1H), 3.37 (s, 3H), 2.38 (s, 3H), 2.22 (s, 3H)
1-160;
8.89 (d, J = 2.4Hz, 1H), 8.53 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.97 (s, 1H), 7.39 (dd, J = 8.4,4.8Hz, 1H), 5.80-5.20 (m, 2H), 4.00-3.60 (m, 4H), 2.45-2.25 (m, 3H), 2.20-1.95 (m, 5H), 1.80 (brs, 3H), 1.03 (t, J = 7.5Hz, 3H)
1-162;
8.97 (d, J = 2.7Hz, 1H), 8.54 (s, 1H), 8.49 (dd, J = 4.8,1.8Hz, 1H), 8.29 (brs, 1H), 7.98 (ddd, J = 8.7,2.7, 1.8Hz, 1H), 7.36 (dd, J = 8.7, 4.8Hz, 1H), 5.23 (dd, J = 8.1, 5.4Hz, 1H), 4.42 (dd, J = 10.2, 8.1Hz, 1H), 4.17 ( s, 3H), 3.96 (dd, J = 10.2, 5.4Hz, 1H), 3.42 (s, 3H), 3.13 (s, 3H), 2.37 (s, 3H)
1-163;
8.98 (d, J = 2.4Hz, 1H), 8.43 (dd, J = 4.8,0.9Hz, 1H), 8.03-7.96 (m, 1H), 7.92 (s, 1H), 7.39 (dd, J = 8.1, 4.8Hz, 1H), 5.18 (d, J = 10.2Hz, 1H), 5.00 (d, J = 10.2Hz, 1H), 4.12 (q, J = 6.9Hz, 2H), 3.85-3.75 (m, 1H) , 3.74 (s, 3H), 2.34 (s, 3H), 1.84 (s, 3H), 1.47 (d, J = 7.5Hz, 3H), 1.25 (t, J = 6.9Hz, 3H)
1-164;
8.89 (d, J = 2.1Hz, 1H), 8.52 (dd, J = 4.8,1.2Hz, 1H), 8.02-7.90 (m, 2H), 7.38 (dd, J = 8.1,4.8Hz, 1H), 5.75 -5.40 (m, 2H), 4.20-3.60 (m, 9H), 3.36 (s, 3H), 3.32 (s, 3H), 2.04 (s, 3H)
1-165;
9.00-8.90 (m, 1H), 8.60-8.50 (m, 1H), 8.10-7.85 (m, 2H), 7.45-7.35 (m, 1H), 5.80-5.40 (m, 2H), 4.60-4.30 (m , 1H), 4.10-3.70 (m, 8H), 3.50-3.30 (m, 3H), 2.80-2.50 (m, 3H), 2.40-2.20 (m, 3H)
1-166;
8.94 (d, J = 2.1Hz, 1H), 8.53 (dd, J = 4.8,1.5Hz, 1H), 8.02-7.90 (m, 2H), 7.38 (dd, J = 8.1,4.8Hz, 1H), 5.80 -5.40 (m, 2H), 5.00-4.80 (m, 1H), 4.28 (dd, J = 10.2,9.3Hz, 1H), 3.89 (dd, J = 10.2,3.6Hz, 1H), 3.80-3.70 (m , 6H), 3.41 (s, 3H), 3.03 (s, 3H), 2.32 (s, 3H)
1-167;
(Isomer ratio 3) 8.90 (d, J = 1.8Hz, 1H), 8.55 (dd, J = 4.8, 1.2Hz, 1H), 8.10-7.80 (m, 2H), 7.45-7.35 (m, 1H), 5.80-5.40 (m, 2H), 4.20-3.70 (m, 7H), 2.70-2.40 (m, 3H), 2.40-2.10 (m, 4H), 2.00-1.70 (m, 1H), 1.20-0.80 (m , 3H)
(Isomer ratio 2) 8.94 (d, J = 2.1Hz, 1H), 8.51 (dd, J = 4.5, 1.5Hz, 1H), 8.10-7.80 (m, 2H), 7.45-7.35 (m, 1H), 5.80-5.40 (m, 2H), 4.20-3.70 (m, 7H), 2.70-2.40 (m, 3H), 2.40-2.10 (m, 4H), 2.00-1.70 (m, 1H), 1.20-0.80 (m , 3H)
1-168;
8.94 (d, J = 2.4Hz, 1H), 8.53 (dd, J = 4.8,1.2Hz, 1H), 8.02 (s, 1H), 8.00-7.90 (m, 1H), 7.38 (dd, J = 7.8, 4.8Hz, 1H), 5.80-5.40 (m, 2H), 4.70-4.50 (m, 1H), 4.00-3.60 (m, 6H), 3.10-2.70 (m, 3H), 2.50-2.10 (m, 5H) , 1.06 (t, J = 7.5Hz, 3H)
1-170;
8.94 (d, J = 2.1Hz, 1H), 8.53 (dd, J = 4.8,1.5Hz, 1H), 8.04-7.90 (m, 2H), 7.38 (dd, J = 8.7,4.8Hz, 1H), 5.75 -5.55 (m, 2H), 4.70-4.50 (m, 1H), 4.20-3.70 (m, 3H), 3.10-2.70 (m, 3H), 2.50-2.20 (m, 8H), 1.07 (t, J = (6.6Hz, 3H)
1-171;
8.93 (d, J = 2.1Hz, 1H), 8.56 (d, J = 4.8Hz, 1H), 8.12 (s, 1H), 8.05-7.95 (m, 1H), 7.42 (dd, J = 8.4,4.8Hz , 1H), 4.64 (d, J = 16.8Hz, 1H), 4.41 (d, J = 16.8Hz, 1H), 3.88 (t, J = 7.8Hz, 1H), 3.73 (s, 3H), 2.39 (s , 3H), 2.10-1.90 (m, 1H), 1.90-1.70 (m, 4H), 1.02 (t, J = 7.2Hz, 3H)
1-172;
9.00-8.86 (m, 1H), 8.65-8.45 (m, 1H), 8.10-7.85 (m, 2H), 7.45-7.35 (m, 1H), 5.24-4.90 (m, 2H), 4.20-3.50 (m , 6H), 2.85-2.45 (m, 3H), 2.35-2.20 (m, 3H), 1.80-1.45 (m, 3H), 1.30-1.20 (m, 3H)
1-173;
(Isomer ratio 58) 9.00-8.90 (m, 1H), 8.60-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.46-7.34 (m, 1H), 5.25 (d, J = 9.6Hz , 1H), 4.95 (d, J = 9.6Hz, 1H), 4.68 (q, J = 7.2Hz, 1H), 3.95-3.65 (m, 5H), 2.77 (brs, 3H), 2.40-2.25 (m, 3H), 1.82-1.40 (m, 3H), 1.30-1.15 (m, 3H)
(Isomer ratio 27) 9.00-8.90 (m, 1H), 8.60-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.46-7.34 (m, 1H), 5.25 (d, J = 9.6Hz , 1H), 4.95 (d, J = 9.6Hz, 1H), 4.68 (q, J = 7.2Hz, 1H), 3.95-3.65 (m, 5H), 2.95 (brs, 3H), 2.40-2.25 (m, 3H), 1.82-1.40 (m, 3H), 1.30-1.15 (m, 3H)
(Isomer ratio 15) 9.00-8.90 (m, 1H), 8.60-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.46-7.34 (m, 1H), 5.25 (d, J = 9.6Hz , 1H), 4.95 (d, J = 9.6Hz, 1H), 4.68 (q, J = 7.2Hz, 1H), 3.95-3.65 (m, 5H), 3.07 (brs, 3H), 2.40-2.25 (m, 3H), 1.82-1.40 (m, 3H), 1.30-1.15 (m, 3H)
1-174;
8.93 (d, J = 2.7Hz, 1H), 8.60-8.50 (m, 1H), 8.11 (s, 1H), 8.10-7.90 (m, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H) , 4.62 (d, J = 16.5Hz, 1H), 4.54 (d, J = 16.5Hz, 1H), 4.13 (q, J = 7.2Hz, 1H), 3.75 (s, 3H), 2.38 (s, 3H) , 1.83 (s, 3H), 1.49 (d, J = 7.2Hz, 3H)
1-175;
(Isomer ratio 5) 9.00-8.85 (m, 1H), 8.65-8.55 (m, 1H), 8.04 (s, 1H), 8.05-7.95 (m, 1H), 7.42 (dd, J = 8.4,4.8Hz , 1H), 4.58 (s, 2H), 4.25-4.00 (m, 1H), 3.79 (s, 3H), 2.54 (s, 3H), 2.35 (s, 3H), 1.50 (d, J = 7.2Hz, 3H)
(Isomer ratio 3) 9.00-8.85 (m, 1H), 8.60-8.50 (m, 1H), 8.16 (s, 1H), 8.00-7.90 (m, 1H), 7.40-7.30 (m, 1H), 4.67 (d, J = 17.1Hz, 1H), 4.46 (d, J = 17.1Hz, 1H), 4.25-4.00 (m, 1H), 3.76 (s, 3H), 2.52 (s, 3H), 2.38 (s, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-176;
8.97 (d, J = 2.4Hz, 1H), 8.55 (dd, J = 4.8,1.5Hz, 1H), 8.14 (s, 1H), 8.05-7.95 (m, 1H), 7.39 (dd, J = 8.4, 4.8Hz, 1H), 4.66 (q, J = 7.2Hz, 1H), 4.58 (d, J = 17.1Hz, 1H), 4.51 (d, J = 17.1Hz, 1H), 3.81 (s, 3H), 2.85 (s, 3H), 2.37 (s, 3H), 1.75 (d, J = 7.2Hz, 3H)
1-177;
9.05-8.80 (m, 1H), 8.70-8.45 (m, 1H), 8.25-7.90 (m, 2H), 7.55-7.30 (m, 1H), 4.75-4.35 (m, 2H), 4.20-4.00 (m , 1H), 3.85-3.70 (m, 3H), 2.60-2.35 (m, 6H), 2.35-1.70 (m, 2H), 1.10-0.90 (m, 3H)
1-178;
8.97 (d, J = 2.7Hz, 1H), 8.55 (dd, J = 4.8,1.2Hz, 1H), 8.14 (s, 1H), 8.00-7.90 (m, 1H), 7.38 (dd, J = 8.4, 4.8Hz, 1H), 4.65-4.45 (m, 3H), 3.78 (s, 3H), 2.83 (s, 3H), 2.38 (s, 3H), 2.30-2.10 (m, 2H), 1.06 (t, J = 7.2Hz, 3H)
1-179;
(Isomer ratio 10) 8.95-8.85 (m, 1H), 8.54 (dd, J = 4.8,1.5Hz, 1H), 8.05-7.90 (m, 2H), 7.39 (dd, J = 8.4,4.8Hz, 1H ), 5.75-5.25 (m, 2H), 4.20-3.80 (m, 1H), 3.74 (brs, 3H), 2.40-2.00 (m, 6H), 1.83 (brs, 3H), 1.55-1.35 (m, 3H) )
(Isomer ratio 1) 9.00-8.90 (m, 1H), 8.55-8.45 (m, 1H), 8.05-7.90 (m, 2H), 7.45-7.30 (m, 1H), 5.75-5.25 (m, 2H) , 4.20-3.80 (m, 4H), 2.40-1.80 (m, 9H), 1.55-1.35 (m, 3H)
1-180;
9.00-8.90 (m, 1H), 8.60-8.45 (m, 1H), 8.10-7.90 (m, 2H), 7.45-7.35 (m, 1H), 5.70-5.15 (m, 2H), 4.25-4.00 (m , 1H), 3.85-3.70 (m, 3H), 2.70-2.50 (m, 3H), 2.40-2.20 (m, 3H), 2.11 (brs, 3H), 1.85-1.50 (m, 3H)
1-181;
8.96 (d, J = 2.4Hz, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.90 (m, 2H), 7.39 (dd, J = 8.4,4.8Hz, 1H), 5.75 -5.35 (m, 2H), 4.66 (q, J = 7.2Hz, 1H), 3.80 (s, 3H), 2.81 (s, 3H), 2.33 (s, 3H), 2.11 (s, 3H), 1.75 ( d, J = 7.2Hz, 3H)
1-182;
9.00-8.85 (m, 1H), 8.65-8.45 (m, 1H), 8.10-7.85 (m, 2H), 7.45-7.30 (m, 1H), 5.80-5.40 (m, 2H), 4.25-4.00 (m , 1H), 3.80-3.65 (m, 6H), 2.70-2.45 (m, 3H), 2.40-2.20 (m, 3H), 1.52 (d, J = 7.2Hz, 3H)
1-183;
8.91 (d, J = 2.4Hz, 1H), 8.56 (dd, J = 4.8,1.5Hz, 1H), 8.09 (s, 1H), 7.96 (ddd, J = 8.4,2.4,1.5Hz, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 4.64 (d, J = 16.8Hz, 1H), 4.51 (d, J = 16.8Hz, 1H), 4.12 (q, J = 7.2Hz, 1H), 4.10 -3.90 (m, 2H), 2.37 (s, 3H), 1.86 (s, 3H), 1.50 (d, J = 7.2Hz, 3H), 1.09 (t, J = 7.2Hz, 3H)
1-184;
8.93 (d, J = 2.4Hz, 1H), 8.55 (dd, J = 4.8,1.5Hz, 1H), 8.08 (s, 1H), 7.97 (ddd, J = 8.4,2.4,1.5Hz, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 4.59 (s, 2H), 4.02 (t, J = 4.2Hz, 2H), 3.58 (s, 2H), 3.32 (t, J = 4.2Hz, 2H) 3.15 (s, 3H), 2.37 (s, 3H), 1.87 (s, 3H)
1-185;
8.89 (d, J = 2.7Hz, 1H), 8.55-8.50 (m, 1H), 8.10-7.85 (m, 2H), 7.45-7.35 (m, 1H), 5.19 (d, J = 9.9Hz, 1H) , 4.98 (d, J = 9.9Hz, 1H), 3.95-3.65 (m, 6H), 2.45-2.30 (m, 3H), 2.20-1.90 (m, 2H), 1.80 (s, 3H), 1.25 (m , 3H), 1.03 (t, J = 7.2Hz, 3H)
1-187;
8.90-8.85 (m, 1H), 8.60-8.45 (m, 1H), 8.10-7.90 (m, 2H), 7.50-7.35 (m, 1H), 5.30-4.90 (m, 2H), 4.20-4.00 (m , 2H), 3.80-3.60 (m, 4H), 2.70-2.20 (m, 6H), 2.00-1.70 (m, 2H), 1.30-1.20 (m, 3H), 1.20-0.90 (m, 3H)
1-189;
9.00-8.85 (m, 1H), 8.65-8.45 (m, 1H), 8.10-7.95 (m, 2H), 7.50-7.35 (m, 1H), 5.30-4.80 (m, 2H), 4.20-4.00 (m , 1H), 3.55-3.40 (m, 3H), 2.75-2.20 (m, 9H), 2.00-1.70 (m, 2H), 1.15-0.90 (m, 3H)
1-190;
(Isomer ratio 2) 9.00-8.90 (m, 1H), 8.55-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.45-7.35 (m, 1H), 5.20-5.10 (m, 1H) , 5.00-4.85 (m, 1H), 4.59 (dd, J = 11.1, 5.4Hz, 1H), 3.77 (s, 3H), 3.50 (s, 3H), 2.76 (s, 3H), 2.40-2.10 (m , 2H), 2.33 (s, 3H), 1.07 (t, J = 7.5Hz, 3H)
(Isomer ratio 1) 9.00-8.90 (m, 1H), 8.55-8.50 (m, 1H), 8.05-7.90 (m, 2H), 7.45-7.35 (m, 1H), 5.20-5.10 (m, 1H) , 5.00-4.85 (m, 1H), 4.59 (dd, J = 11.1, 5.4Hz, 1H), 3.88 (brs, 3H), 3.48 (s, 3H), 2.88 (s, 3H), 2.40-2.10 (m , 2H), 2.32 (s, 3H), 1.20-0.90 (m, 3H)
1-191;
(Isomer ratio 51) 9.02-8.92 (m, 1H), 8.60-8.50 (m, 1H), 8.40-7.94 (m, 2H), 7.45-7.35 (m, 1H), 5.30-4.60 (m, 3H) , 3.87 (brs, 3H), 3.47 (s, 3H), 2.94 (s, 3H), 2.31 (s, 3H), 1.82-1.42 (m, 3H)
(Isomer ratio 25) 9.02-8.92 (m, 1H), 8.60-8.50 (m, 1H), 8.40-7.94 (m, 2H), 7.45-7.35 (m, 1H), 5.30-4.60 (m, 3H) , 4.05 (s, 3H), 3.38 (s, 3H), 2.78 (s, 3H), 2.33 (s, 3H), 1.82-1.42 (m, 3H)
(Isomer ratio 24) 9.02-8.92 (m, 1H), 8.60-8.50 (m, 1H), 8.40-7.94 (m, 2H), 7.45-7.35 (m, 1H), 5.30-4.60 (m, 3H) , 3.81 (s, 3H), 3.50 (s, 3H), 3.06 (s, 3H), 2.26 (s, 3H), 1.82-1.42 (m, 3H)
1-192;
8.89 (d, J = 2.4Hz, 1H), 8.55-8.50 (m, 1H), 8.05-7.85 (m, 2H), 7.45-7.35 (m, 1H), 5.15 (d, J = 10.5Hz, 1H) , 4.90 (d, J = 10.5Hz, 1H), 4.10-3.80 (m, 1H), 3.73 (s, 3H), 3.50 (s, 3H), 2.36 (s, 3H), 2.20-1.90 (m, 2H ), 1.81 (s, 3H), 1.03 (t, J = 7.2Hz, 3H)
1-194;
9.10-8.80 (m, 1H), 8.65-8.55 (m, 1H), 8.35-8.10 (m, 1H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H), 4.85-4.60 (m , 2H), 3.80-3.60 (m, 1H), 3.36 (s, 3H), 1.90 (s, 3H), 1.50-1.30 (m, 3H)
1-195;
9.05-8.80 (m, 1H), 8.70-8.45 (m, 1H), 8.25-7.90 (m, 2H), 7.55-7.30 (m, 1H), 4.75-4.35 (m, 2H), 4.20-4.00 (m , 1H), 3.85-3.70 (m, 3H), 2.60-2.35 (m, 6H), 2.35-1.70 (m, 2H), 1.10-0.90 (m, 3H)
1-196;
9.00-8.80 (m, 1H), 8.65-8.55 (m, 1H), 8.30-7.90 (m, 2H), 7.50-7.40 (m, 1H), 3.85-3.30 (m, 4H), 2.30-2.20 (m , 3H), 2.20-1.35 (m, 6H)
1-197;
8.98 (d, J = 2.7Hz, 1H), 8.59 (s, 1H), 8.49 (dd, J = 4.8, 1.5Hz, 1H), 8.32 (brs, 1H), 7.97 (ddd, J = 8.7, 2.7. 1.5Hz, 1H), 7.36 (dd, J = 8.7, 4.8Hz, 1H), 3.96 (s, 3H), 2.35 (s, 3H), 2.14 (s, 3H), 1.55 (s, 6H)
1-198;
9.00-8.85 (m, 1H), 8.65-8.40 (m, 2H), 8.10-7.90 (m, 1H), 7.50-7.30 (m, 1H), 5.35 (m, 2H), 3.55-3.30 (m, 7H ), 1.90-1.75 (m, 3H), 1.65-1.30 (m, 3H)
1-200;
8.97 (d, J = 2.7Hz, 1H), 8.77 (brs, 1H), 8.58 (s, 1H), 8.49 (dd, J = 4.8,1.5Hz, 1H), 7.98 (ddd, J = 7.8,2.7. 1.5Hz, 1H), 7.36 (dd, J = 7.8, 4.8Hz, 1H), 4.03 (s, 3H), 3.08 (s, 3H), 2.35 (s, 3H), 1.74 (s, 6H)
1-203;
8.98 (d, J = 2.7Hz, 1H), 8.54 (s, 1H), 8.50 (dd, J = 4.8,1.5Hz, 1H), 7.98 (ddd, J = 8.1,2.7,1.5Hz, 1H), 7.93 (s, 1H), 7.78 (d, J = 8.4Hz, 2H), 7.37 (dd, J = 8.1,4.8Hz, 1H), 7.29 (d, J = 8.4Hz, 2H), 5.59 (dd, J = 8.7, 6.0 Hz, 1H), 4.06 (s, 3H), 2.41 (s, 3H), 2.35 (s, 3H), 2.25-2.10 (m, 1H), 2.00-1.80 (m, 1H), 0.87 (t , J = 7.2Hz, 3H)
1-205;
9.01-8.97 (m, 1H), 8.72-8.66 (m, 1H), 8.63 (s, 1H), 8.52-8.48 (m, 1H), 8.31 (brs, 1H), 8.02-7.95 (m, 1H), 7.69-7.62 (m, 1H), 7.41-7.33 (m, 1H), 7.30-7.23 (m, 1H), 5.75 (t, J = 7.8Hz, 1H), 4.13 (s, 3H), 2.37 (s, 3H), 2.22-2.00 (m, 2H), 1.03 (t, J = 7.2Hz, 3H)
1-207;
(Isomer ratio 2) 8.96 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.56-8.44 (m, 2H), 8.20-7.92 (m, 1H), 7.71-7.65 (m, 1H ), 7.71-7.65 (m, 5H), 4.09 (s, 3H), 2.43 (s, 3H)
(Isomer ratio 1) 8.99 (d, J = 1.8Hz, 1H), 8.67 (s, 1H), 8.56-8.44 (m, 1H), 8.20-7.92 (m, 2H), 7.71-7.65 (m, 6H ), 4.11 (s, 3H), 2.36 (s, 3H)
1-208;
9.00 (brs, 1H), 8.67 (brs, 1H), 8.07 (s, 1H), 8.02 (d, J = 8.7Hz, 1H), 7.45 (brs, 1H), 3.91 (s, 3H), 3.71 (q , J = 6.9Hz, 1H), 2.10 (s, 3H), 2.06 (s, 3H), 1.48 (d, J = 6.9Hz, 3H)
1-212;
8.98 (d, J = 3.0Hz, 1H), 8.70-8.60 (m, 1H), 8.54 (s, 1H), 8.45 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.4, 3.0,1.2Hz, 1H), 7.86 (t, J = 4.5Hz, 1H), 7.35 (dd, J = 8.4,4.8Hz, 1H), 4.75-4.60 (m, 1H), 3.50-3.30 (m, 2H ), 2.37 (s, 3H), 2.15-1.70 (m, 5H), 1.27 (t, J = 7.2Hz, 3H), 0.99 (t, J = 7.2Hz, 3H)
1-218;
9.82 (s, 1H), 9.00 (d, J = 2.7Hz, 1H), 8.60 (s, 1H), 8.50 (dd, J = 4.8,1.2Hz, 1H), 8.01 (ddd, J = 8.4,2.7, 1.2Hz, 1H), 7.40-6.75 (m, 7H), 3.80-3.65 (m, 1H), 2.40 (s, 3H), 2.14 (s, 3H), 2.10-1.85 (m, 2H), 1.07 (t , J = 7.2Hz, 3H)
1-222;
8.98 (d, J = 2.4Hz, 1H), 8.83 (brs, 1H), 8.61 (s, 1H), 8.53 (dd, J = 4.8,1.0Hz, 1H), 8.07 (t, J = 4.5Hz, 1H ), 7.99 (ddd, J = 8.4, 2.4, 1.0 Hz, 1H), 7.38 (dd, J = 8.4, 4.8 Hz, 1H), 6.05-5.85 (m, 1H), 5.35-5.20 (m, 2H), 4.78 (q, J = 7.5Hz, 1H), 4.10-4.00 (m, 2H), 2.02 (s, 3H), 1.47 (d, J = 7.5Hz, 3H)
1-225;
(Isomer ratio 3) 8.97 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.47 (dd, J = 4.8,1.2Hz, 1H), 8.37 (brs, 1H), 7.99-7.95 ( m, 1H), 7.35 (dd, J = 8.1,4,8Hz, 1H), 5.90-5.68 (m, 1H), 5.20-5.04 (m, 2H), 4.06 (s, 3H), 3.16 (d, J = 8.1Hz, 2H), 2.72-2.51 (m, 1H), 2.37 (s, 3H), 2.14-1.77 (m, 2H), 0.97 (t, J = 8.4Hz, 3H)
(Isomer ratio 1) 8.97 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.47 (dd, J = 4.8,1.2Hz, 1H), 8.39 (brs, 1H), 7.99-7.95 ( m, 1H), 7.35 (dd, J = 8.1,4,8Hz, 1H), 5.90-5.68 (m, 1H), 5.20-5.04 (m, 2H), 4.06 (s, 3H), 3.11 (d, J = 8.1Hz, 2H), 2.72-2.51 (m, 1H), 2.37 (s, 3H), 2.14-1.77 (m, 2H), 1.07-0.95 (m, 3H)
1-231;
10.3 (brs, 1H), 8.98 (d, J = 2.4Hz, 1H), 8.58 (s, 1H), 8.52 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.90 (m, 1H), 7.45 -7.20 (m, 7H), 5.26 (s, 2H), 4.01 (q, J = 7.2Hz, 1H), 2.39 (s, 3H), 2.20 (s, 3H), 1.58 (d, J = 7.2Hz, 3H)
1-232:
(Isomer ratio 7) 9.76 (s, 1H), 8.99 (d, J = 2.4Hz, 1H), 8.73 (s, 1H), 8.56 (dd, J = 4.8,1.5Hz, 1H), 8.03-7.95 ( m, 1H), 7.46-7.36 (m, 1H), 4.45-4.25 (m, 2H), 4.16 (q, J = 7.2Hz, 1H), 2.09 (s, 3H), 1.90-1.70 (m, 2H) , 1.55 (d, J = 7.2Hz, 3H), 1.50-1.25 (m, 6H), 1.00-0.82 (m, 3H)
(Isomer ratio 3) 9.76 (s, 1H), 8.99 (d, J = 2.4Hz, 1H), 8.66 (s, 1H), 8.56 (dd, J = 4.8,1.5Hz, 1H), 8.03-7.95 ( m, 1H), 7.46-7.36 (m, 1H), 4.45-4.25 (m, 2H), 4.16 (q, J = 7.2Hz, 1H), 2.16 (s, 3H), 1.90-1.70 (m, 2H) , 1.66 (d, J = 7.2Hz, 3H), 1.50-1.25 (m, 6H), 1.00-0.82 (m, 3H)
1-233;
(Isomer ratio 2) 9.92 (s, 1H), 9.20-8.95 (m, 1H), 8.75 (s, 1H), 8.60-8.50 (m, 1H), 8.06-7.94 (m, 1H), 7.46-7.34 (m, 1H), 4.22-4.06 (m, 3H), 2.09 (s, 3H), 1.55 (d, J = 7.2Hz, 3H), 1.36-1.10 (m, 1H), 0.73-0.60 (m, 2H ), 0.45-0.34 (m, 2H)
(Isomer ratio 1) 9.92 (s, 1H), 9.20-8.95 (m, 1H), 8.70 (s, 1H), 8.60-8.50 (m, 1H), 8.06-7.94 (m, 1H), 7.46-7.34 (m, 1H), 4.50-4.40 (m, 1H), 4.22-4.06 (m, 2H), 2.18 (s, 3H), 1.68 (d, J = 7.2Hz, 3H), 1.36-1.10 (m, 1H ), 0.73-0.60 (m, 2H), 0.45-0.34 (m, 2H)
1-237;
11.3 (brs, 1H), 10.0 (brs, 1H), 9.01 (d, J = 2.7Hz, 1H), 8.60 (s, 1H), 8.50 (dd, J = 4.5,1.2Hz, 1H), 8.05-7.95 (m, 1H), 7.40 (dd, J = 8.4,4.5Hz, 1H), 6.06 (t, J = 6.0Hz, 1H), 3.83 (q, H = 7.2Hz, 1H), 3.45-3.35 (m, 2H), 2.39 (s, 3H), 2.18 (s, 3H), 1.61 (d, J = 7.2Hz, 3H), 1.21 (t, J = 7.2Hz, 3H)
1-238;
10.7 (brs, 1H), 9.72 (brs, 1H), 8.99 (d, J = 2.7Hz, 1H), 8.64 (s, 1H), 8.54 (dd, J = 4.8,1.2Hz, 1H), 8.04 (ddd , J = 8.4,2.7,1.2Hz, 1H), 7.42 (dd, J = 8.4,4.8Hz, 1H), 4.25 (q, J = 7.2Hz, 1H), 3.70-3.50 (m, 1H), 2.05- 1.00 (m, 16H)
1-240;
(Isomer ratio 7) 8.98 (brs, 1H), 8.64 (s, 1H), 8.60-8.50 (m, 2H), 8.04-7.96 (m, 1H), 7.41 (dd, J = 8.4,5.1Hz, 1H ), 5.85-5.60 (m, 1H), 5.25-5.10 (m, 2H), 5.01 (dd, J = 9.9, 5.1Hz, 1H), 4.19 (s, 3H), 3.34-3.16 (m, 1H), 3.10 (s, 3H), 3.05-2.93 (m, 1H)
(Isomer ratio 3) 9.65 (brs, 1H), 8.98 (brs, 1H), 8.67 (s, 1H), 8.60-8.50 (m, 1H), 8.04-7.96 (m, 1H), 7.41 (dd, J = 8.4, 5.1Hz, 1H), 5.85-5.60 (m, 1H), 5.25-5.10 (m, 2H), 4.88 (dd, J = 10.5, 4.8Hz, 1H), 4.25 (s, 3H), 3.34- 3.16 (m, 1H), 3.05-2.93 (m, 1H), 2.98 (s, 3H)
1-242;
(Isomer ratio 2) 8.99 (s, 1H), 8.70 (s, 1H), 8.64-8.52 (m, 2H), 8.05-7.95 (m, 1H), 7.48-7.36 (m, 1H), 4.87 (d , J = 2.7Hz, 2H), 4.41 (q, J = 7.2Hz, 1H), 2.59 (t, J = 2.7Hz, 1H), 2.18 (s, 3H), 1.67 (d, J = 7.2Hz, 3H )
(Isomer ratio 1) 9.20 (s, 1H), 8.99 (s, 1H), 8.72 (s, 1H), 8.64-8.52 (m, 1H), 8.10-8.05 (m, 1H), 7.48-7.36 (m , 1H), 4.58 (d, J = 2.7Hz, 2H), 4.07 (q, J = 7.2Hz, 1H), 2.25 (t, J = 2.7Hz, 1H), 2.12 (s, 3H), 1.55 (d , J = 7.2Hz, 3H)
1-245;
8.99 (d, J = 2.7Hz, 1H), 8.62 (s, 1H), 8.49 (dd, J = 4.8,1.2Hz, 1H), 8.45 (brs, 1H), 8.04-7.90 (m, 1H), 7.36 (dd, J = 8.1,4,8Hz, 1H), 4.26-4.14 (m, 1H), 4.08 (s, 3H), 2.74-2.58 (m, 1H), 2.39 (s, 3H), 2.20-1.88 ( m, 4H), 1.85-1.67 (m, 2H), 1.66-1.55 (m, 1H), 1.42-1.18 (m, 5H), 0.99 (t, J = 7.5Hz, 3H)
1-247;
(Isomer ratio 6) 12.0 (brs, 1H), 9.41 (brs, 1H), 8.96 (d, J = 2.4Hz, 1H), 8.52 (s, 1H), 8.47 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.30 (m, 7H), 4.98 (q, J = 7.2Hz, 1H), 2.42 (s, 3H), 2.16 (s, 3H), 1.58 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 12.0 (brs, 1H), 10.5 (brs, 1H), 9.00 (d, J = 2.4Hz, 1H), 8.63 (s, 1H), 8.55-8.45 (m, 1H), 8.05- 7.30 (m, 7H), 4.20-4.00 (m, 1H), 2.25 (s, 3H), 2.11 (s, 3H), 1.65 (d, J = 7.2Hz, 3H)
1-248;
(Isomer ratio 5) 9.05-8.95 (m, 1H), 8.74 (brs, 1H), 8.70-8.60 (m, 1H), 8.55-8.40 (m, 1H), 8.10-7.85 (m, 1H), 7.45 -7.30 (m, 1H), 4.13 (q, J = 7.2Hz, 1H), 3.70-3.25 (m, 4H), 2.36 (s, 3H), 2.16 (s, 3H), 2.00-1.80 (m, 4H ), 1.77 (d, J = 7.2Hz, 3H)
(Isomer ratio 2) 10.1 (brs, 1H), 9.05-8.95 (m, 1H), 8.70-8.60 (m, 1H), 8.55-8.40 (m, 1H), 8.10-7.85 (m, 1H), 7.45 -7.30 (m, 1H), 3.91 (q, J = 7.2Hz, 1H), 3.55-3.10 (m, 4H), 2.42 (s, 3H), 2.11 (s, 3H), 2.00-1.80 (m, 4H ), 1.51 (d, J = 7.2Hz, 3H)
1-249;
(Isomer ratio 10) 12.2 (brs, 1H), 10.2 (brs, 1H), 9.05-8.95 (m, 1H), 8.65-8.45 (m, 2H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H), 4.90-3.80 (m, 1H), 3.80-3.45 (m, 2H), 2.40-2.10 (m, 6H), 1.65-1.50 (m, 3H)
(Isomer ratio 9) 11.1 (brs, 1H), 9.05-8.95 (m, 1H), 8.65-8.45 (m, 3H), 8.10-7.95 (m, 1H), 7.50-7.35 (m, 1H), 4.90 -3.80 (m, 1H), 3.80-3.45 (m, 2H), 2.40-2.10 (m, 6H), 1.65-1.50 (m, 3H)
1-250;
12.3 (brs, 1H), 9.89 (brs, 1H), 9.05-8.95 (m, 1H), 8.90-8.80 (m, 2H), 8.55-8.45 (m, 1H), 8.30-8.15 (m, 1H), 8.05-7.90 (m, 1H), 7.70-7.55 (m, 1H), 7.40-7.25 (m, 1H), 6.95-6.80 (m, 1H), 3.95 (q, J = 7.2Hz, 1H), 2.40 ( s, 3H), 2.17 (s, 3H), 1.66 (d, J = 7.2Hz, 3H)
1-253;
8.96 (d, J = 2.4Hz, 1H), 8.60 (brs, 1H), 8.55-8.45 (m, 2H), 8.00-7.90 (m, 1H), 7.40-7.30 (m, 1H), 4.19 (s, 3H), 2.92 (q, J = 7.2Hz, 2H), 2.36 (s, 3H), 1.16 (t, J = 7.2Hz, 3H)
1-255;
9.00-8.90 (m, 1H), 8.57 (s, 1H), 8.50-8.40 (m, 1H), 8.20-7.90 (m, 2H), 7.40-7.25 (m, 1H), 3.98 (s, 3H), 3.91 (s, 3H), 2.60-2.45 (m, 2H), 2.31 (s, 3H), 1.02 (t, J = 7.5Hz, 3H)
1-256;
8.99 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.51 (dd, J = 4.8,1.2Hz, 1H), 8.35-8.20 (m, 1H), 8.05-7.95 (m, 1H) , 7.44-7.34 (m, 1H), 4.91 (s, 2H), 4.37 (q, J = 7.5Hz, 1H), 2.40 (s, 3H), 2.20 (s, 3H), 1.68 (d, J = 7.5 (Hz, 3H)
1-257;
(Isomer ratio 7) 9.50-9.30 (m, 1H), 9.01-8.88 (m, 1H), 8.65 (s, 1H), 8.50 (dd, J = 4.8, 1.5Hz, 1H), 8.10-7.85 (m , 1H), 7.41-7.32 (m, 1H), 4.48-4.38 (m, 2H), 4.20-4.10 (m, 1H), 3.80-3.64 (m, 2H), 3.42 (s, 3H), 2.38 (s , 3H), 2.10 (s, 3H), 1.55 (d, J = 7.2Hz, 3H)
(Isomer ratio 3) 9.50-9.30 (m, 1H), 9.01-8.88 (m, 1H), 8.61 (s, 1H), 8.50 (dd, J = 4.8, 1.5Hz, 1H), 8.10-7.85 (m , 1H), 7.41-7.32 (m, 1H), 4.48-4.38 (m, 2H), 4.20-4.10 (m, 1H), 3.80-3.64 (m, 2H), 3.42 (s, 3H), 2.38 (s , 3H), 2.18 (s, 3H), 1.66 (d, J = 7.5Hz, 3H)
1-258;
(Isomer ratio 5) 11.8 (brs, 1H), 10.0 (brs, 1H), 9.05-8.90 (m, 1H), 8.59 (s, 1H), 8.55-8.45 (m, 1H), 8.10-7.95 (m , 1H), 7.50-7.30 (m, 1H), 3.84 (q, J = 7.2Hz, 1H), 2.39 (s, 3H), 2.17 (s, 3H), 2.05 (d, J = 7.2Hz, 2H) , 1.60 (d, J = 7.2Hz, 3H), 1.20-1.00 (m, 1H), 0.80-0.50 (m, 2H), 0.35-0.15 (m, 2H)
(Isomer ratio 2) 10.4 (brs, 1H), 9.05-8.90 (m, 1H), 8.60-8.40 (m, 3H), 8.10-7.95 (m, 1H), 7.50-7.30 (m, 1H), 4.80 (q, J = 7.2Hz, 1H), 2.41 (s, 3H), 2.36 (d, J = 9.6Hz, 2H), 2.23 (s, 3H), 1.53 (d, J = 7.2Hz, 3H), 1.20 -1.00 (m, 1H), 0.80-0.50 (m, 2H), 0.35-0.15 (m, 2H)
1-261;
(Isomer ratio 3) 11.8 (brs, 1H), 10.0 (brs, 1H), 9.05-8.90 (m, 1H), 8.65-8.45 (m, 2H), 8.10-7.90 (m, 1H), 7.45-7.25 (m, 1H), 3.84 (q, J = 7.2Hz, 1H), 3.70-3.40 (m, 2H), 2.45-2.20 (m, 9H), 1.61 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 10.4 (brs, 1H), 9.05-8.90 (m, 1H), 8.65-8.45 (m, 3H), 8.10-7.90 (m, 1H), 7.45-7.25 (m, 1H), 4.81 (q, J = 7.2Hz, 1H), 3.70-3.40 (m, 2H), 2.45-2.20 (m, 9H), 1.53 (d, J = 7.2Hz, 3H)
1-264;
(Isomer ratio 3) 8.99 (s, 1H), 8.69 (s, 1H), 8.60 (s, 1H), 8.58-8.52 (m, 1H), 8.01-7.98 (m, 1H), 7.45-7.36 (m , 1H), 6.14-5.97 (m, 1H), 5.45-5.33 (m, 2H), 4.84-4.74 (m, 2H), 4.41 (q, J = 7.5Hz, 1H), 2.17 (s, 3H), 1.67 (d, J = 7.5Hz, 3H)
(Isomer ratio 2) 9.60 (s, 1H), 8.99 (s, 1H), 8.72 (s, 1H), 8.58-8.52 (m, 1H), 8.01-7.98 (m, 1H), 7.45-7.36 (m , 1H), 6.14-5.97 (m, 1H), 5.45-5.33 (m, 2H), 4.84-4.74 (m, 2H), 4.13 (q, J = 7.5Hz, 1H), 2.09 (s, 3H), 1.54 (d, J = 7.5Hz, 3H)
1-265;
(Isomer ratio 7) 9.47 (s, 1H), 9.03-8.95 (m, 1H), 8.73 (s, 1H), 8.56 (dd, J = 4.8, 1.2Hz, 1H), 8.06-7.94 (m, 1H ), 7.46-7.36 (m, 1H), 4.88-4.70 (m, 2H), 3.93 (q, J = 7.2Hz, 1H), 3.85 (s, 3H), 2.07 (s, 3H), 1.55 (d, (J = 7.2Hz, 3H)
(Isomer ratio 3) 9.03-8.95 (m, 1H), 8.69 (s, 1H), 8.56 (dd, J = 4.8, 1.2Hz, 1H), 8.47 (s, 1H), 8.06-7.94 (m, 1H ), 7.46-7.36 (m, 1H), 4.57-4.41 (m, 2H), 4.29 (q, J = 7.2Hz, 1H), 3.83 (s, 3H), 1.97 (s, 3H), 1.50 (d, (J = 7.2Hz, 3H)
1-266;
(Isomer ratio 3) 9.43 (d, J = 5.1Hz, 1H), 8.99 (s, 1H), 8.66 (d, J = 1.5Hz, 1H), 8.60-8.48 (m, 1H), 8.06-7.94 ( m, 1H), 7.40 (dd, J = 8.1,4.8Hz, 1H), 4.44-3.96 (m, 4H), 2.65-2.44 (m, 1H), 2.12 (s, 3H), 1.65 (dd, J = 7.2, 1.8Hz, 3H), 1.34-1.20 (m, 3H)
(Isomer ratio 2) 8.99 (s, 1H), 8.71 (s, 1H), 8.60-8.48 (m, 2H), 8.06-7.94 (m, 1H), 7.40 (dd, J = 8.1, 4.8Hz, 1H ), 4.44-3.96 (m, 4H), 2.86-2.65 (m, 1H), 2.20 (d, J = 1.5Hz, 3H), 1.54 (dd, J = 7.2, 3.0Hz, 3H), 1.34-1.20 ( m, 3H)
1-267;
(Isomer ratio 4) 10.80 (s, 1H), 9.10-8.90 (m, 1H), 8.74 (s, 1H), 8.59-8.49 (m, 1H), 8.06-7.92 (m, 1H), 7.50-7.30 (m, 1H), 4.99-4.74 (m, 2H), 3.89 (q, J = 7.2Hz, 1H), 3.81-3.56 (m, 6H), 3.48-3.32 (m, 2H), 2.07 (s, 3H ), 1.57 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 9.10-8.90 (m, 1H), 8.68 (s, 1H), 8.59-8.49 (m, 1H), 8.06-7.92 (m, 1H), 7.50-7.30 (m, 1H), 4.99 -4.74 (m, 2H), 4.44 (q, J = 7.2Hz, 1H), 3.81-3.56 (m, 6H), 3.56-3.48 (m, 2H), 2.23 (s, 3H), 1.69 (d, J = 7.2Hz, 3H) (No proton peak of NH was observed)
1-268;
(Isomer ratio 1) 9.05-8.93 (m, 1H), 8.69 (s, 1H), 8.60 (s, 1H), 8.64-8.48 (m, 1H), 8.08-7.93 (m, 1H), 7.55-7.30 (m, 1H), 4.45-4.10 (m, 3H), 2.16 (s, 3H), 1.91-1.68 (m, 3H), 1.65 (d, J = 7.2Hz, 3H), 1.47-1.22 (m, 7H ), 0.97-0.83 (m, 3H)
(Isomer ratio 1) 9.76 (s, 1H), 9.05-8.93 (m, 1H), 8.74 (s, 1H), 8.64-8.48 (m, 1H), 8.08-7.93 (m, 1H), 7.55-7.30 (m, 1H), 4.45-4.10 (m, 3H), 2.09 (s, 3H), 1.91-1.68 (m, 3H), 1.55 (d, J = 7.2Hz, 3H), 1.47-1.22 (m, 7H ), 0.97-0.83 (m, 3H)
1-270;
9.55 and 8.52 (s, 1H), 9.28 (d, J = 2.4Hz, 1H), 8.79 and 8.74 (s, 1H), 8.67-8.56 (m, 1H), 8.56-8.40 (m, 1H), 7.96- 7.85 (m, 1H), 4.50-3.65 (m, 3H), 2.38 and 2.36 (s, 3H), 2.17 and 2.10 (s, 3H), 1.65 and 1.54 (d, J = 7.2Hz, 3H), 1.48- 1.34 (m, 3H)
1-271;
(Isomer ratio 3) 9.31 (d, J = 2.4Hz, 1H), 8.76 (s, 1H), 8.69-8.59 (m, 1H), 8.59-8.51 (m, 1H), 8.48 (s, 1H), 8.06-7.89 (m, 1H), 4.33-4.20 (m, 2H), 3.73 (q, J = 7.2Hz, 1H), 2.38 (s, 3H), 2.17 (s, 3H), 1.95-1.68 (m, 2H), 1.65 (d, J = 7.2Hz, 3H), 1.09-0.98 (m, 3H)
(Isomer ratio 2) 9.55 (s, 1H), 9.31 (d, J = 2.4Hz, 1H), 8.81 (s, 1H), 8.69-8.59 (m, 1H), 8.59-8.51 (m, 1H), 8.06-7.89 (m, 1H), 4.40 (q, J = 7.2Hz, 1H), 4.33-4.20 (m, 2H), 2.36 (s, 3H), 2.09 (s, 3H), 1.95-1.68 (m, 2H), 1.54 (d, J = 7.2Hz, 3H), 1.09-0.98 (m, 3H)
1-272;
(Isomer ratio 3) 9.03-8.93 (m, 1H), 8.61 (s, 1H), 8.54-8.45 (m, 1H), 8.42 (s, 1H), 8.04-7.92 (m, 1H), 7.43-7.32 (m, 1H), 4.40 (q, J = 7.2Hz, 1H), 4.24-4.03 (m, 2H), 2.38 (s, 3H), 2.19 (s, 3H), 1.67 (d, J = 7.2Hz, 3H), 1.37-1.08 (m, 1H), 0.74-0.58 (m, 2H), 0.46-0.30 (m, 2H)
(Isomer ratio 2) 9.67 (s, 1H), 9.03-8.93 (m, 1H), 8.67 (s, 1H), 8.54-8.45 (m, 1H), 8.04-7.92 (m, 1H), 7.43-7.32 (m, 1H), 4.24-4.03 (m, 3H), 2.38 (s, 3H), 2.10 (s, 3H), 1.54 (d, J = 7.2Hz, 3H), 1.37-1.08 (m, 1H), 0.74-0.58 (m, 2H), 0.46-0.30 (m, 2H)
1-273;
8.99 (d, J = 2.4Hz, 1H), 8.61 (s, 1H), 8.49 (dd, J = 4.8,1.2Hz, 1H), 8.28 (s, 1H), 8.04-7.91 (m, 1H), 7.47 -7.31 (m, 3H), 6.90-6.78 (m, 2H), 4.48 (dd, J = 8.7,7.2Hz, 1H), 3.93 (s, 3H), 3.80 (s, 3H), 2.37 (s, 3H ), 2.31-2.02 (m, 2H), 1.00 (t, J = 7.2Hz, 3H)
1-274;
(Isomer ratio 3) 9.12-8.93 (m, 2H), 8.63 (s, 1H), 8.54-8.35 (m, 1H), 8.04-7.94 (m, 1H), 7.44-7.30 (m, 1H), 5.32 (s, 2H), 4.06 (q, J = 7.2Hz, 1H), 2.38 (s, 3H), 2.32 (s, 3H), 2.14 (s, 3H), 1.55 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 9.12-8.93 (m, 2H), 8.60 (s, 1H), 8.54-8.35 (m, 1H), 8.04-7.94 (m, 1H), 7.44-7.30 (m, 1H), 5.32 (s, 2H), 4.40 (q, J = 7.2Hz, 1H), 2.38 (s, 3H), 2.31 (s, 3H), 2.20 (s, 3H), 1.68 (d, J = 7.2Hz, 3H)
1-275;
(Isomer ratio 6) 11.1 (brs, 1H), 9.35-8.85 (m, 2H), 8.70-8.40 (m, 2H), 8.05-7.80 (m, 1H), 7.70-7.50 (m, 1H), 7.50 -7.20 (m, 6H), 4.85 (q, J = 7.2Hz, 1H), 2.35 (s, 3H), 2.14 (s, 3H), 1.48 (d, J = 7.2Hz, 3H)
(Isomer ratio 5) 10.1 (brs, 1H), 9.35-8.85 (m, 2H), 8.70-8.40 (m, 2H), 8.05-7.80 (m, 1H), 7.70-7.50 (m, 1H), 7.50 -7.20 (m, 6H), 3.92 (q, J = 7.2Hz, 1H), 2.40 (s, 3H), 2.22 (s, 3H), 1.67 (d, J = 7.2Hz, 3H)
1-276;
11.4 (brs, 1H), 10.0 (brs, 1H), 9.01 (d, J = 2.4Hz, 1H), 8.60 (s, 1H), 8.51 (dd, J = 4.8,1.5Hz, 1H), 8.00 (ddd , J = 8.4,2.7,1.2Hz, 1H), 7.38 (dd, J = 8.4,4.8Hz, 1H), 6.20 (t, J = 6.3Hz, 1H), 6.00-5.85 (m, 1H), 5.30- 5.10 (m, 2H), 4.05-3.90 (m, 2H), 3.85 (q, J = 7.2Hz, 1H), 2.39 (s, 3H), 2.19 (s, 3H), 1.61 (d, J = 7.2Hz , 3H)
1-280;
(Isomer ratio 2) 11.3 (brs, 1H), 10.0-9.85 (m, 1H), 9.00 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.55-8.45 (m, 1H), 8.05-7.95 (m, 1H), 7.45-7.30 (m, 1H), 5.99 (d, J = 7.8Hz, 1H), 4.30-4.05 (m, 1H), 3.84 (q, J = 7.2Hz, 1H) , 2.39 (s, 3H), 2.17 (s, 3H), 1.80-1.40 (m, 11H)
(Isomer ratio 1) 10.0-9.85 (m, 1H), 8.97 (d, J = 2.4Hz, 1H), 8.54 (s, 1H), 8.55-8.45 (m, 1H), 8.34 (brs, 1H), 8.05-7.95 (m, 1H), 7.45-7.30 (m, 1H), 5.75 (d, J = 7.8Hz, 1H), 4.80 (q, J = 7.2Hz, 1H), 4.30-4.05 (m, 1H) , 2.37 (s, 3H), 2.08 (s, 3H), 1.80-1.40 (m, 11H)
1-282;
11.2 (brs, 1H), 9.10 (brs, 1H), 9.00-8.90 (m, 1H), 8.60-8.40 (m, 2H), 8.10-7.95 (m, 1H), 7.37 (dd, J = 8.4,4.8 Hz, 1H), 5.85-5.75 (m, 1H), 4.88 (q, J = 7.2Hz, 1H), 3.11 (s, 2H), 2.39 (s, 3H), 2.08 (s, 3H), 1.80-1.40 (m, 11H)
1-285;
8.98 (d, J = 2.4Hz, 1H), 8.55 (brs, 1H), 8.53-8.48 (m, 1H), 8.34 (brs, 1H), 8.04-7.96 (m, 1H), 7.38 (dd, J = 8.1, 4.8Hz, 1H), 5.16 (dd, J = 9.6, 6.6Hz, 1H), 4.20 (s, 3H), 3.44-3.14 (m, 2H), 3.11 (s, 3H), 2.38 (s, 3H ), 2.10 (t, J = 2.7Hz, 1H)
1-286;
10.63 (brs, 1H), 9.01 (brs, 1H), 8.83 (s, 1H), 8.62 (brs, 1H), 8.15-8.05 (m, 1H), 7.55-7.35 (m, 1H), 4.20-4.05 ( m, 4H), 2.70 (s, 3H), 2.20-1.90 (m, 5H), 1.00 (t, J = 7.5Hz, 3H)
1-287;
8.91 (s, 1H), 8.53 (d, J = 4.5Hz, 1H), 8.05-7.95 (m, 1H), 7.98 (s, 1H), 7.40 (dd, J = 8.4,4.5Hz, 1H), 3.95 -3.80 (m, 4H), 2.74 (s, 3H), 2.43 (s, 3H), 2.10-1.90 (m, 1H), 1.90-1.70 (m, 4H), 1.03 (t, J = 7.2Hz, 3H )
1-289;
(Isomer ratio 3) 9.20-8.96 (m, 1H), 8.68 (s, 1H), 8.60-8.52 (m, 1H), 8.46 (s, 1H), 8.08-7.94 (m, 1H), 7.48-7.36 (m, 1H), 4.70-4.56 (m, 2H), 4.41 (q, J = 7.2Hz, 1H), 2.17 (s, 3H), 1.68 (d, J = 7.2Hz, 3H)
(Isomer ratio 2) 9.20-8.96 (m, 1H), 8.77 (s, 1H), 8.70 (s, 1H), 8.60-8.52 (s, 1H), 8.08-7.94 (m, 1H), 7.48-7.36 (m, 1H), 4.70-4.56 (m, 2H), 3.99 (q, J = 7.2Hz, 1H), 2.11 (s, 3H), 1.54 (d, J = 7.2Hz, 3H)
1-290;
(Isomer ratio 4) 10.1 (brs, 1H), 9.00-8.90 (m, 1H), 8.58 (s, 1H), 8.50-8.40 (m, 1H), 8.10-7.90 (m, 3H), 7.85-7.70 (m, 3H), 7.35-7.20 (m, 1H), 4.45-4.25 (m, 1H), 2.41 (s, 3H), 2.30 (s, 3H), 1.50 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 10.5 (brs, 1H), 9.00-8.90 (m, 1H), 8.56 (s, 1H), 8.50-8.40 (m, 1H), 8.10-7.90 (m, 3H), 7.85-7.70 (m, 3H), 7.35-7.20 (m, 1H), 4.45-4.25 (m, 1H), 2.43 (s, 3H), 2.16 (s, 3H), 1.62 (d, J = 7.2Hz, 3H)
1-292;
8.97 (d, J = 2.7Hz, 1H), 8.62 (brs, 1H), 8.53 (s, 1H), 8.46 (dd, J = 4.8,1.2Hz, 1H), 8.05-7.80 (m, 2H), 7.35 (dd, J = 8.4,4.8Hz, 1H), 4.83 (q, J = 7.2Hz, 1H), 3.50-3.35 (m, 2H), 2.42 (s, 3H), 2.01 (s, 3H), 1.47 ( d, J = 7.2Hz, 3H), 1.27 (t, J = 7.2Hz, 3H)
1-293;
11.8 (brs, 1H), 10.2 (brs, 1H), 8.96 (d, J = 2.4Hz, 1H), 8.60 (s, 1H), 8.52 (dd, J = 4.8,1.2Hz, 1H), 8.05 (ddd , J = 8.4,2.4,1.2Hz, 1H), 7.41 (dd, J = 8.4,4.8Hz, 1H), 4.01 (q, J = 7.2Hz, 1H), 3.84 (s, 3H), 2.40 (s, 3H), 2.20 (s, 3H), 1.59 (d, J = 7.2Hz, 3H)
1-296;
11.9 (brs, 1H), 10.3 (brs, 1H), 9.00 (d, J = 2.7Hz, 1H), 8.61 (s, 1H), 8.60-8.50 (m, 1H), 8.00 (ddd, J = 8.4, 2.7, 1.2Hz, 1H), 7.40 (dd, J = 8.4, 4.8Hz, 1H), 6.10-5.85 (m, 1H), 5.45-5.20 (m, 2H), 4.73 (d, J = 6, 0Hz, 2H), 4.01 (q, J = 7.2Hz, 1H), 2.40 (s, 3H), 2.21 (s, 3H), 1.59 (d, J = 7.2Hz, 3H)
1-297;
9.00 (d, J = 3.0Hz, 1H), 8.70-8.60 (m, 2H), 8.55-8.45 (m, 1H), 8.10-8.00 (m, 1H), 7.50-7.35 (m, 1H), 4.24 ( q, J = 7.2Hz, 1H), 2.38 (s, 3H), 2.19 (s, 3H), 2.19 (s, 3H), 1.59 (d, J = 7.2Hz, 3H) (NH proton peak is observed (Not)
1-298;
(Isomer ratio 4) 13.0 (brs, 1H), 10.4 (brs, 1H), 9.05-8.90 (m, 1H), 8.65-8.45 (m, 2H), 8.10-7.90 (m, 1H), 7.45-7.30 (m, 1H), 6.85-6.70 (m, 1H), 4.20-4.00 (m, 1H), 2.80-2.50 (m, 6H), 2.41 (s, 3H), 2.22 (s, 3H), 1.62 (d , J = 7.2Hz, 3H)
(Isomer ratio 1) 9.05-8.90 (m, 1H), 8.65-8.45 (m, 3H), 8.10-7.90 (m, 1H), 7.45-7.30 (m, 1H), 6.75-6.65 (m, 1H) , 4.20-4.00 (m, 1H), 2.80-1.95 (m, 9H), 2.34 (s, 3H), 1.70-1.50 (m, 3H) (NH proton peak was not observed)
1-299;
8.87 (d, J = 2.4Hz, 1H), 8.52 (d, J = 4.8Hz, 1H), 8.10-7.90 (m, 2H), 7.39 (dd, J = 8.1,4.8Hz, 1H), 4.00-3.60 (m, 8H), 2.34 (s, 3H), 2.15-1.90 (m, 1H), 1.80-1.60 (m, 4H), 1.01 (t, J = 7.2Hz, 3H), 0.86 (s, 9H), 0.10-0.02 (m, 6H)
1-306;
9.03 (d, J = 2.4Hz, 1H), 8.94 (brs, 1H), 8.88 (s, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.08 (ddd, J = 8.1,2.4, 1.2Hz, 1H), 7.44 (dd, J = 8.1, 4.8Hz, 1H), 4.20-4.05 (m, 4H), 2.20-1.95 (m, 5H), 1.00 (t, J = 7.5Hz, 3H)
1-307;
8.93 (d, J = 2.7Hz, 1H), 8.59 (dd, J = 4.5,1.5Hz, 1H), 8.07 (ddd, J = 8.1,2.7,1.5Hz, 1H), 8.02 (s, 1H), 7.43 (dd, J = 8.1,4.5Hz, 1H), 4.20-3.75 (m, 3H), 3.75 (s, 3H), 2.10-1.70 (m, 5H), 1.23 (t, J = 7.2Hz, 3H), 1.01 (t, J = 7.2Hz, 3H), 0.26 (s, 9H)
1-309;
11.6 (brs, 1H), 10.1 (brs, 1H), 9.00 (d, J = 2.1Hz, 1H), 8.65-8.45 (m, 2H), 7.99 (ddd, J = 8.4,2.1,1.2Hz, 1H) , 7.45-7.35 (m, 1H), 3.85 (q, J = 7.5Hz, 1H), 3.13 (s, 3H), 2.39 (s, 3H), 2.20 (s, 3H), 1.60 (d, J = 7.5 (Hz, 3H)
1-312;
9.70-9.50 (m, 1H), 9.10-8.80 (m, 1H), 8.70-8.45 (m, 1H), 8.20-7.70 (m, 2H), 7.50-7.30 (m, 1H), 4.00-3.55 (m , 8H), 3.34 (s, 3H), 2.45-2.00 (m, 6H), 1.41 (d, J = 7.5Hz, 3H)
1-313;
(Isomer ratio 5) 9.05-8.85 (m, 2H), 8.68 (s, 1H), 8.55-8.45 (m, 1H), 8.10-7.95 (m, 1H), 7.45-7.30 (m, 1H), 3.95 -3.70 (m, 1H), 3.25 (s, 3H), 2.40-2.05 (m, 6H), 1.80 (d, J = 7.2Hz, 3H), 1.60-1.40 (m, 9H)
(Isomer ratio 3) 9.05-8.85 (m, 2H), 8.54 (s, 1H), 8.55-8.45 (m, 1H), 8.10-7.95 (m, 1H), 7.45-7.30 (m, 1H), 3.95 -3.70 (m, 1H), 3.17 (s, 3H), 2.40-2.05 (m, 6H), 1.60-1.40 (m, 12H)
1-314;
8.98 (d, J = 2.7Hz, 1H), 8.59 (s, 1H), 8.52-8.46 (m, 1H), 8.30 (s, 1H), 8.04-7.92 (m, 1H), 7.42-7.32 (m, 1H), 4.80 (s, 2H), 4.47 (q, J = 7.2Hz, 1H), 4.28 (q, J = 7.2Hz, 2H), 2.35 (s, 3H), 2.23 (s, 3H), 1.70 ( d, J = 7.2Hz, 3H), 1.33 (t, J = 7.2Hz, 3H)
1-315;
(Isomer ratio 7) 8.59 (s, 1H), 8.53-8.46 (m, 1H), 8.38 (s, 1H), 8.04-7.94 (m, 1H), 7.42-7.32 (m, 1H), 4.74 (s , 2H), 4.39 (q, J = 7.2Hz, 1H), 3.93 (s, 3H), 2.37 (s, 3H), 2.18 (s, 3H), 1.95 (s, 3H), 1.66 (d, J = (7.2Hz, 3H)
(Isomer ratio 3) 8.98 (d, J = 2.4Hz, 1H), 8.59 (s, 1H), 8.53-8.46 (m, 1H), 8.32 (s, 1H), 8.04-7.94 (m, 1H), 7.42-7.32 (m, 1H), 5.07 (s, 2H), 4.39 (q, J = 7.2Hz, 1H), 3.88 (s, 3H), 2.37 (s, 3H), 2.20 (s, 3H), 1.98 (s, 3H), 1.67 (d, J = 7.2Hz, 3H)
1-316;
(Isomer ratio 4) 9.29 (s, 1H), 9.03-8.96 (m, 1H), 8.65 (s, 1H), 8.52-8.46 (m, 1H), 8.02-7.94 (m, 1H), 7.42-7.32 (m, 1H), 5.24-5.18 (m, 1H), 4.50-4.05 (m, 3H), 4.05-3.90 (m, 4H), 2.38 (s, 3H), 2.09 (s, 3H), 1.53 (d , J = 7.2Hz, 3H)
(Isomer ratio 1) 9.03-8.96 (m, 1H), 8.60 (s, 1H), 8.52-8.46 (m, 1H), 8.42 (s, 1H), 8.02-7.94 (m, 1H), 7.42-7.32 (m, 1H), 5.24-5.18 (m, 1H), 4.50-4.05 (m, 3H), 4.05-3.90 (m, 4H), 2.37 (s, 3H), 2.17 (s, 3H), 1.66 (d , J = 7.2Hz, 3H)
1-318;
(Isomer ratio 7) 8.96 (s, 1H), 8.92 (s, 1H), 8.61 (s, 1H), 8.52-8.46 (m, 1H), 8.02-7.94 (m, 1H), 7.74-7.66 (m , 2H), 7.58-7.48 (m, 2H), 7.42-7.33 (m, 1H), 5.30 (s, 2H), 3.96 (q, J = 7.2Hz, 1H), 2.20 (s, 3H), 2.01 ( s, 3H), 1.49 (d, J = 7.2Hz, 3H)
(Isomer ratio 3) 8.97 (s, 1H), 8.56 (s, 1H), 8.52-8.46 (m, 1H), 8.27 (s, 1H), 8.02-7.94 (m, 1H), 7.74-7.66 (m , 2H), 7.58-7.48 (m, 2H), 7.42-7.33 (m, 1H), 5.34 (s, 2H), 4.40 (q, J = 7.2Hz, 1H), 2.32 (s, 3H), 2.16 ( s, 3H), 1.65 (d, J = 7.2Hz, 3H)
1-319;
(Isomer ratio 7) 9.31 (s, 1H), 9.00-8.90 (m, 1H), 8.60 (s, 1H), 8.50-8.45 (m, 1H), 8.02-7.88 (m, 1H), 7.40-7.22 (m, 5H), 5.22 (s, 2H), 4.12 (q, J = 7.2Hz, 1H), 2.49 (s, 3H), 2.02 (s, 3H), 2.00 (s, 3H), 1.53 (d, (J = 7.2Hz, 3H)
(Isomer ratio 3) 9.00-8.90 (m, 1H), 8.58 (s, 1H), 8.50-8.45 (m, 1H), 8.33 (s, 1H), 8.02-7.88 (m, 1H), 7.40-7.22 (m, 5H), 5.21 (s, 2H), 4.39 (q, J = 7.2Hz, 1H), 2.49 (s, 3H), 2.33 (s, 3H), 2.11 (s, 3H), 1.63 (d, (J = 7.2Hz, 3H)
1-320;
10.5 (s, 1H), 9.06-8.90 (m, 1H), 8.70-6.90 (m, 9H), 4.22-4.08 (m, 1H), 3.04-2.94 (m, 1H), 2.43 (s, 3H), 2.26 (s, 3H), 2.10-1.90 (m, 2H), 1.65 (d, J = 7.2Hz, 3H)
1-321;
8.98 (d, J = 2.4Hz, 1H), 8.58 (s, 1H), 8.50 (dd, J = 4.8,1.5Hz, 1H), 8.31 (brs, 1H), 7.99 (ddd, J = 8.1,2.4, 1.5Hz, 1H), 7.37 (dd, J = 8.1, 4.8Hz, 1H), 4.41 (t, J = 8.1Hz, 1H), 4.11 (s, 3H), 3.31 (d, J = 8.1Hz, 2H) , 2.99 (ddd, J = 14.4, 6.9, 2.7Hz, 2H), 2.78 (ddd, J = 14.4, 9.0, 2.7Hz, 2H), 2.38 (s, 3H), 2.20-1.90 (m, 2H)
1-322;
8.95-8.85 (m, 1H), 8.52 (dd, J = 4.8,1.5Hz, 1H), 8.10-7.90 (m, 2H), 7.39 (dd, J = 8.1,4.8Hz, 1H), 4.27 (t, J = 7.5Hz, 1H), 3.69 (s, 3H), 3.30 (s, 3H), 3.11 (d, J = 7.5Hz, 2H), 3.00-2.88 (m, 2H), 2.81 (ddd, J = 14.4 , 9.3,3.3Hz, 2H), 2.31 (s, 3H), 2.20-1.80 (m, 2H)
1-323;
(Isomer ratio 1) 8.98 (d, J = 2.4Hz, 1H), 8.58-8.46 (m, 2H), 8.42-8.30 (m, 1H), 8.05-7.98 (m, 1H), 7.39 (dd, J = 8.4, 4.8Hz, 1H), 4.12-3.92 (m, 1H), 4.08 (s, 3H), 3.33 (dd, J = 12.9, 7.2Hz, 1H), 3.23 (dd, J = 12.9, 8.1Hz, 1H), 2.63 (s, 3H), 2.37 (s, 3H), 1.46-1.38 (m, 3H)
(Isomer ratio 1) 8.98 (d, J = 2.4Hz, 1H), 8.58-8.46 (m, 2H), 8.42-8.30 (m, 1H), 8.05-7.98 (m, 1H), 7.39 (dd, J = 8.4, 4.8Hz, 1H), 4.12-3.92 (m, 1H), 4.09 (s, 3H), 3.57 (dd, J = 13.2, 10.2Hz, 1H), 3.00-2.90 (m, 1H), 2.61 ( s, 3H), 2.37 (s, 3H), 1.46-1.38 (m, 3H)
1-324;
8.98 (d, J = 2.7Hz, 1H), 8.54-8.46 (m, 2H), 8.31 (brs, 1H), 8.05-7.98 (m, 1H), 7.42-7.35 (m, 1H), 4.16-3.92 ( m, 2H), 4.11 (s, 3H), 3.28-3.18 (m, 1H), 2.93 (s, 3H), 2.36 (s, 3H), 1.46-1.38 (m, 3H)
1-325;
(Isomer ratio 3) 8.93-8.86 (m, 1H), 8.56-8.50 (m, 1H), 8.04-7.93 (m, 1H), 7.92 (s, 1H), 7.39 (dd, J = 8.4, 4.8Hz , 1H), 3.70 (s, 3H), 3.27 (s, 3H), 3.25-3.12 (m, 1H), 2.95-2.82 (m, 1H), 2.66-2.52 (m, 1H), 2.31 (s, 3H ), 2.04 (s, 3H), 1.21 (d, J = 7.2Hz, 3H)
(Isomer ratio 1) 8.93-8.86 (m, 1H), 8.56-8.50 (m, 1H), 8.04-7.93 (m, 1H), 7.92 (s, 1H), 7.39 (dd, J = 8.4, 4.8Hz , 1H), 3.99 (s, 3H), 3.46 (s, 3H), 3.25-3.12 (m, 1H), 2.95-2.82 (m, 1H), 2.66-2.52 (m, 1H), 2.31 (s, 3H ), 2.05 (s, 3H), 1.33 (d, J = 7.2Hz, 3H)
1-326;
8.98 (d, J = 2.4Hz, 1H), 8.64 (s, 1H), 8.60-8.50 (m, 2H), 8.01 (ddd, J = 8.4,2.4,1.2Hz, 1H), 7.40 (dd, J = 8.4, 4.8Hz, 1H), 4.08 (s, 3H), 3.78-3.64 (m, 1H), 3.10 (dd, J = 13.2, 9.6Hz, 1H), 2.73 (dd, J = 13.2, 6.9Hz, 1H ), 2.11 (s, 3H), 1.34 (t, J = 7.2Hz, 3H)
1-327;
9.04-8.92 (m, 1H), 8.63-8.46 (m, 2H), 8.24 (brs, 1H), 8.10-7.88 (m, 1H), 7.58-7.18 (m, 6H), 5.83 (s, 1H), 4.13 (s, 3H), 2.36 (s, 3H)
1-328;
9.06-8.98 (m, 1H), 8.75-8.30 (m, 2H), 8.62 (s, 1H), 8.08-7.98 (m, 1H), 7.52-7.38 (m, 1H), 5.50-5.36 (m, 2H ), 4.03 (s, 3H), 2.34 (s, 3H), 2.04-1.96 (m, 3H)
1-330;
9.08 (brs, 1H), 9.00-8.90 (m, 1H), 8.65-8.40 (m, 2H), 8.05-7.90 (m, 1H), 7.40-7.30 (m, 1H), 4.00-3.55 (m, 3H ), 2.36 (s, 3H), 2.25-2.10 (m, 6H), 1.57 (d, J = 7.2Hz, 3H), 1.25 (t, J = 6.9Hz, 3H)
1-331;
9.05-8.95 (m, 2H), 8.60 (s, 1H), 8.50-8.40 (m, 1H), 8.05-7.90 (m, 1H), 7.40-7.30 (m, 1H), 4.21 (q, J = 7.2 Hz, 1H), 4.05 (s, 3H), 3.45-3.20 (m, 2H), 2.32 (s, 3H), 2.26 (t, J = 2.4Hz, 1H), 1.58 (d, J = 7.2Hz, 3H )
1-333;
(Isomer ratio 4) 8.92 (d, J = 2.4Hz, 1H), 8.53 (dd, J = 4.8, 1.2Hz, 1H), 8.01 (ddd, J = 8.4, 2.4, 1.2Hz, 1H), 7.97 ( s, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 4.77 (t, J = 8.1Hz, 1H), 3.70 (s, 3H), 3.35-3.20 (m, 7H), 3.03 (d , J = 8,1Hz, 2H), 2.33 (s, 3H)
(Isomer ratio 1) 8.92 (d, J = 2.4 Hz, 1 H), 8.53 (dd, J = 4.8, 1.2 Hz, 1 H), 8.01 (ddd, J = 8.4, 2.4, 1.2 Hz, 1 H), 7.97 ( s, 1H), 7.40 (dd, J = 8.4,4.8Hz, 1H), 4.96 (t, J = 7.8Hz, 1H), 4.01 (s, 3H), 3.53 (s, 3H), 3.35-3.20 (m , 4H), 3.11 (d, J = 7.8Hz, 2H), 2.33 (s, 3H)
1-334;
8.92-8.88 (m, 1H), 8.52 (dd, J = 4.8,1.2Hz, 1H), 8.00 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.95 (s, 1H), 7.38 (dd, J = 8.4, 4.8Hz, 1H), 5.05 (s, 2H), 4.30-4.20 (m, 1H), 4.07 (s, 3H), 3.71 (s, 3H), 3.20-3.10 (m, 2H), 3.00 -2.90 (m, 2H), 2.85-2.70 (m, 2H), 2.30 (s, 3H), 2.15-2.00 (m, 1H), 2.00-1.85 (m, 1H)
1-335;
9.50-8.90 (m, 1H), 8.75-8.50 (m, 3H), 8.05-7.90 (m, 1H), 7.45-7.35 (m, 1H), 4.45-4.05 (m, 4H), 3.80-3.60 (m , 1H), 2.60-2.20 (m, 1H), 2.25-2.13 (m, 3H), 1.75-1.50 (m, 3H), 1.25-1.00 (m, 3H) (NH2 proton peak was not observed)
1-336;
8.95-8.85 (m, 1H), 8.60-8.45 (m, 1H), 8.06-7.92 (m, 2H), 7.45-7.35 (m, 1H), 5.92-5.58 (m, 1H), 5.30-4.90 (m , 2H), 3.95-3.84 (m, 1H), 3.80-3.70 (m, 3H), 3.35-3.26 (m, 3H), 3.26-2.50 (m, 2H), 2.50-2.30 (m, 3H), 2.30 -1.60 (m, 2H), 1.15-0.90 (m, 3H)
1-337;
8.97 (d, J = 2.4Hz, 1H), 8.68 (s, 1H), 8.60-8.52 (m, 1H), 8.44 (s, 1H), 8.06-7.94 (m, 1H), 7.45-7.35 (m, 1H), 4.82 (s, 2H), 4.46 (q, J = 7.2Hz, 1H), 2.26 (s, 3H), 2.23 (s, 3H), 1.70 (d, J = 7.2Hz, 3H)
1-338;
9.46-9.34 and 8.36-8.30 (m, 1H), 9.02-8.94 (m, 1H), 8.62 and 8.58 (s, 1H), 8.54-8.46 (m, 1H), 8.04-7.94 (m, 1H), 7.42 -7.32 (m, 1H), 6.03-5.84 (m, 1H), 5.55-5.30 (m, 2H), 4.65-4.55 and 4.40-4.30 (m, 1H), 4.14 and 4.13 (s, 3H), 3.72- 3.60 and 3.34-3.24 (m, 1H), 3.52-3.38 (m, 1H), 2.40 and 2.39 (s, 3H), 2.35-1.83 (m, 2H), 1.10-0.95 (m, 3H)
1-342;
8.98 (d, J = 2.4Hz, 1H), 8.62-8.40 (m, 3H), 8.04-7.92 (m, 1H), 7.44-7.34 (m, 1H), 6.06-5.86 (m, 1H), 5.58- 5.46 (m, 2H), 5.04-4.92 (m, 1H), 4.20-4.10 (m, 3H), 3.92 (d, J = 7.2Hz, 2H), 2.62-2.42 (m, 1H), 2.41-2.35 ( m, 3H), 2.35-2.10 (m, 1H), 1.04-0.60 (m, 3H)
1-343;
8.99 (s, 1H), 8.56 (s, 1H), 8.54-8.45 (m, 1H), 8.45-8.30 (m, 1H), 8.10-7.90 (m, 1H), 7.44-7.30 (m, 1H), 4.06 (s, 3H), 3.68-3.54 (m, 1H), 3.11 (dd, J = 13.5,10.2Hz, 1H), 2.78 (dd, J = 13.5,6.0Hz, 1H), 2.39 (s, 3H) , 2.12 (s, 3H), 2.06-1.85 (m, 1H), 1.85-1.65 (m, 1H), 0.93 (t, J = 7.5Hz, 3H)
1-344;
8.99 (s, 1H), 8.56 (s, 1H), 8.54-8.45 (m, 1H), 8.45-8.30 (m, 1H), 8.10-7.90 (m, 1H), 7.44-7.30 (m, 1H), 4.06 (s, 3H), 3.48-3.23 (m, 2H), 2.39 (s, 3H), 2.12 (s, 3H), 1.43 (d, J = 6.9Hz, 3H), 1.26 (d, J = 6.9Hz , 3H)
3-002;
9.09 (d, J = 1.8Hz, 1H), 8.70 (dd, J = 4.8,1.2Hz, 1H), 8.20 (ddd, J = 8.1,1.8,1.2Hz, 1H), 7.40 (dd, J = 8.1, 4.8Hz, 1H), 3.92-3.81 (m, 2H), 3.36 (brs, 3H), 3.54 (s, 2H), 2.08 (s, 3H), 1.28 (t, J = 7.2Hz, 3H)
3-006;
9.10-9.07 (m, 1H), 8.65 (dd, J = 4.8,1.5Hz, 1H), 8.21-8.17 (m, 1H), 7.40-7.34 (m, 1H), 5.20 (brs, 2H), 4.15- 4.00 (m, 1H), 3.84-3.65 (m, 5H), 2.40 (s, 3H), 2.04 (brs, 3H), 1.51 (d, J = 7.8Hz, 3H), 1.26 (t, J = 7.2Hz , 3H)
3-007;
9.20-9.00 (m, 1H), 8.70-8.60 (m, 1H), 8.30-8.10 (m, 1H), 7.50-7.30 (m, 1H), 6.10-5.60 (m, 2H), 4.25-4.00 (m , 3H), 4.00-3.75 (m, 1H), 2.65-2.45 (m, 3H), 2.45-2.20 (m, 3H), 2.20-2.20 (m, 3H), 1.72-1.50 (m, 3H)
3-008;
9.10 (d, J = 2.1Hz, 1H), 8.65 (dd, J = 4.8,1.8Hz, 1H), 8.19 (ddd, J = 7.5,2.1,1.8Hz, 1H), 7.38 (dd, J = 7.5, 4.8Hz, 1H), 4.75-4.35 (m, 2H), 4.15-4.00 (m, 1H), 3.90-3.65 (m, 3H), 2.43 (s, 3H), 2.35-2.25 (m, 1H), 2.20 -1.95 (m, 3H), 1.51 (d, J = 7.2Hz, 3H)
3-010;
(Isomer ratio 88) 9.10 (d, J = 1.5Hz, 1H), 8.66 (dd, J = 4.8,1.5Hz, 1H), 8.18 (ddd, J = 8.1,1.5,1.5Hz, 1H), 7.38 ( dd, J = 8.1, 4.8Hz, 1H), 4.20 (q, J = 7.5Hz, 1H), 3.99 (s, 3H), 3.83 (s, 3H), 2.36 (s, 3H), 2.19 (s, 3H ), 1.58 (d, J = 7.5Hz, 3H)
(Isomer ratio 12) 9.10 (d, J = 1.5Hz, 1H), 8.66 (dd, J = 4.8,1.5Hz, 1H), 8.18 (ddd, J = 8.1,1.5,1.5Hz, 1H), 7.38 ( dd, J = 8.1,4.8Hz, 1H), 4.20 (q, J = 7.5Hz, 1H), 3.92 (s, 3H), 3.83 (s, 3H), 2.33 (s, 3H), 2.15 (s, 3H ), 1.58 (d, J = 7.5Hz, 3H)
3-012;
(Isomer ratio 9) 9.12-9.07 (m, 1H), 8.68-8.60 (m, 1H), 8.22-8.14 (m, 1H), 7.39 (dd, J = 7.5, 4.8Hz, 1H), 4.35-3.15 (m, 6H), 2.41 (s, 3H), 2.03 (brs, 3H), 1.68-1.40 (m, 3H), 1.20-1.00 (m, 1H), 0.60-0.48 (m, 2H), 0.32-0.18 (m, 2H)
(Isomer ratio 1) 9.07-9.03 (m, 1H), 8.75-8.71 (m, 1H), 8.22-8.14 (m, 1H), 7.39 (dd, J = 7.5, 4.8Hz, 1H), 4.35-3.15 (m, 6H), 2.41 (s, 3H), 2.03 (brs, 3H), 1.68-1.40 (m, 3H), 1.20-1.00 (m, 1H), 0.60-0.48 (m, 2H), 0.32-0.18 (m, 2H)
3-013;
(Isomer ratio 56) 9.16-9.10 (m, 1H), 8.92 (brs, 1H), 8.64-8.8.56 (m, 1H), 8.20-8.12 (m, 1H), 7.40-7.30 (m, 1H) , 4.38 (q, J = 7.2Hz, 1H), 4.15 (s, 3H), 2.55 (s, 3H), 2.49 (s, 3H), 1.71 (d, J = 7.2Hz, 3H)
(Isomer ratio 44) 10.23 (brs, 1H), 9.16-9.10 (m, 1H), 8.64-8.8.56 (m, 1H), 8.20-8.12 (m, 1H), 7.40-7.30 (m, 1H) , 4.58 (q, J = 7.2Hz, 1H), 4.15 (s, 3H), 2.69 (s, 3H), 2.50 (s, 3H), 1.65 (d, J = 7.2Hz, 3H)
3-017;
9.11 (d, J = 2.4Hz, 1H), 8.90 (brs, 1H), 8.61 (dd, J = 4.8,1.8Hz, 1H), 8.17 (ddd, J = 8.4,2.4.1.8Hz, 1H), 7.35 (dd, J = 8.4, 4.8Hz, 1H), 4.87 (dd, J = 10.8, 5.1Hz, 1H), 4.19 (s, 3H), 3.10 (s, 3H), 2.55-2.40 (m, 4H), 2.35-2.20 (m, 1H), 1.03 (t, J = 7.2Hz, 3H)
3-023;
9.13 (d, J = 1.8Hz, 1H), 8.87 (s, 1H), 8.63-8.57 (m, 1H), 8.20-8.12 (m, 1H), 7.39-7.30 (m, 1H), 4.28 (t, J = 7.8Hz, 1H), 4.11 (s, 3H), 3.30-3.00 (m, 2H), 2.49 (s, 3H), 2.19-1.96 (m, 2H), 1.00 (t, J = 7.5Hz, 3H )
3-024;
9.16-9.10 (m, 1H), 8.84 (brs, 1H), 8.68-8.63 (m, 1H), 8.63-8.57 (m, 1H), 8.20-8.15 (m, 1H), 7.68-7.62 (m, 1H ), 7.40-7.30 (m, 1H), 7.28-7.23 (m, 1H), 5.70 (t, J = 8.1Hz, 1H), 4.13 (s, 3H), 2.48 (s, 3H), 2.27-2.00 ( m, 2H), 1.03 (t, J = 7.5Hz, 3H)
3-026;
9.13 (d, J = 1.5Hz, 1H), 8.67 (dd, J = 4.8,1.5Hz, 1H), 8.26-8.20 (m, 1H), 7.80 (s, 1H), 7.44-7.38 (m, 1H) 4.20 (q, J = 7.2Hz, 1H), 4.00 (s, 3H), 2.19 (s, 3H), 1.56 (d, J = 7.2Hz, 3H) (No proton peak of NH was observed)
3-028;
9.60-9.52 (m, 1H), 9.14 (d, J = 2.1Hz, 1H), 8.60 (dd, J = 4.8,1.8Hz, 1H), 8.18 (m, 1H), 7.37 (dd, J = 7.5, 4.8Hz, 1H), 4.80-4.70 (m, 1H), 4.13 (s, 3H), 3.43 (s, 3H), 2.48 (s, 3H), 2.07-1.90 (m, 1H), 1.90-1.73 (m , 1H), 0.96 (t, J = 7.5Hz, 3H)
3-029;
(Isomer ratio 7) 9.12 (d, J = 1.5Hz, 1H), 8.95 (s, 1H), 8.59 (dd, J = 4.8,1.5Hz, 1H), 8.20-8.13 (m, 1H), 7.34 ( dd, J = 8.1,4.8Hz, 1H), 5.90-5.74 (m, 1H), 5.20-5.05 (m, 2H), 4.09 (s, 3H), 3.16 (d, J = 7.2Hz, 2H), 2.73 -2.45 (m, 1H), 2.49 (s, 3H), 2.16-1.75 (m, 2H), 0.97 (t, J = 7.2Hz, 3H)
(Isomer ratio 3) 9.12 (d, J = 1.5Hz, 1H), 8.93 (s, 1H), 8.59 (dd, J = 4.8,1.5Hz, 1H), 8.20-8.13 (m, 1H), 7.34 ( dd, J = 8.1,4.8Hz, 1H), 5.90-5.74 (m, 1H), 5.20-5.05 (m, 2H), 4.09 (s, 3H), 3.11 (d, J = 7.2Hz, 2H), 2.73 -2.45 (m, 1H), 2.49 (s, 3H), 2.16-1.75 (m, 2H), 1.05-0.93 (m, 3H)
3-032;
9.13 (d, J = 1.8Hz, 1H), 9.02 (s, 1H), 8.61 (dd, J = 4.8,1.8Hz, 1H), 8.22-8.10 (m, 1H), 7.41-7.30 (m, 1H) , 4.30-4.15 (m, 1H), 4.11 (s, 3H), 2.74-2.60 (m, 1H), 2.50 (s, 3H), 2.20-1.55 (m, 7H), 1.42-1.18 (m, 5H) , 0.99 (t, J = 7.2Hz, 3H)
3-033;
9.17-9.10 (m, 1H), 8.81 (s, 1H), 8.61 (dd, J = 4.8,1.5Hz, 1H), 8.24-8.12 (m, 1H), 7.49-7.33 (m, 3H), 6.89- 6.78 (m, 2H), 4.48 (dd, J = 8.7,7.8Hz, 1H), 3.96 (s, 3H), 3.79 (s, 3H), 2.48 (s, 3H), 2.30-2.02 (m, 2H) , 1.00 (t, J = 7.8Hz, 3H)
3-034;
9.14-9.10 (m, 1H), 8.85 (brs, 1H), 8.62 (dd, J = 4.8,1.8Hz, 1H), 8.22-8.14 (m, 1H), 7.40-7.32 (m, 1H), 5.19- 5.10 (m, 1H), 4.22 (s, 3H), 3.42-3.18 (m, 2H), 3.11 (s, 3H), 2.49 (s, 3H), 2.11 (t, J = 2.7Hz, 1H)
3-036 (* 3);
9.15-9.05 (m, 2H), 8.70-8.60 (m, 1H), 8.58 (dd, J = 4.8,1.5Hz, 1H), 8.25-8.10 (m, 1H), 7.40-7.30 (m, 1H), 4.82 (q, J = 7.5Hz, 1H), 4.05-3.90 (m, 2H), 2.46 (s, 3H), 2.02 (s, 3H), 1.48 (d, J = 7.5Hz, 3H)
3-040;
12.7 (brs, 1H), 11.3 (brs, 1H), 9.20-9.10 (m, 1H), 8.63 (dd, J = 4.8,1.5Hz, 1H), 8.35-8.20 (m, 1H), 7.45-7.35 ( m, 1H), 4.20-4.05 (m, 3H), 3.52 (s, 3H), 2.54 (s, 3H), 2.24 (s, 3H), 1.61 (d, J = 7.2Hz, 3H)
3-043;
11.3 (brs, 1H), 10.7 (brs, 1H), 9.20-9.10 (m, 1H), 8.63 (dd, J = 4.8,1.2Hz, 1H), 8.18 (ddd, J = 8.4,2.7,1.2Hz, 1H), 7.37 (dd, J = 8.4, 4.8Hz, 1H), 6.18 (t, J = 5.4Hz, 1H), 6.00-5.85 (m, 1H), 5.30-5.10 (m, 2H), 4.10-3.90 (m, 2H), 3.89 (q, J = 7.2Hz, 1H), 2.53 (s, 3H), 2.20 (s, 3H), 1.61 (d, J = 7.2Hz, 3H)
3-045;
(Isomer ratio 2) 11.2 (brs, 1H), 9.40-8.90 (m, 2H), 8.65-8.50 (m, 1H), 8.25-8.10 (m, 1H), 7.70-7.25 (m, 7H), 4.83 (q, J = 7.2Hz, 1H), 2.47 (s, 3H), 2.13 (s, 3H), 1.80-1.50 (m, 3H)
(Isomer ratio 1) 12.4 (brs, 1H), 10.8 (brs, 1H), 9.40-8.90 (m, 1H), 8.65-8.50 (m, 1H), 8.25-8.10 (m, 1H), 7.70-7.25 (m, 7H), 3.95 (q, J = 7.2Hz, 1H), 2.54 (s, 3H), 2.24 (s, 3H), 1.80-1.50 (m, 3H)
3-047;
9.21 (brs, 1H), 9.20-9.10 (m, 1H), 8.57 (dd, J = 4.8, 1.2Hz, 1H), 8.25-8.10 (m, 2H), 7.40-7.30 (m, 1H), 6.10- 5.85 (m, 1H), 5.40-5.20 (m, 2H), 4.79 (q, J = 7.2Hz, 1H), 4.15-4.00 (m, 2H), 2.46 (s, 3H), 2.02 (s, 3H) , 1.46 (d, J = 7.2Hz, 3H)
3-048;
9.20 (brs, 1H), 9.13 (d, J = 2.4Hz, 1H), 8.57 (dd, J = 4.8,1.5Hz, 1H), 8.25-8.05 (m, 2H), 7.40-7.30 (m, 1H) , 4.79 (q, J = 7.2Hz, 1H), 3.55-3.40 (m, 2H), 2.48 (s, 3H), 2.01 (s, 3H), 1.46 (d, J = 7.2Hz, 3H), 1.29 ( (t, J = 7.2Hz, 3H)
3-055;
9.64 and 9.15 (brs, 1H), 9.12 (brs, 1H), 8.70-8.62 (m, 1H), 8.25-8.15 (m, 1H), 7.44-7.36 (m, 1H), 4.65 (q, J = 8.1 Hz, 2H), 4.41 and 4.03 (q, J = 7.5Hz, 1H), 2.16 and 2.09 (s, 3H), 1,86 and 1.54 (d, J = 7.5Hz, 3H)
4-002;
(Isomer ratio 5) 9.05 (d, J = 2.7Hz, 1H), 8.60-8.50 (m, 1H), 8.50 (s, 1H), 8.15-8.00 (m, 1H), 7.39 (dd, J = 8.4 , 4.8Hz, 1H), 6.10-5.90 (m, 2H), 4.47 (q, J = 7.2Hz, 1H), 4.05 (s, 3H), 3.45-3.05 (m, 4H), 2.22 (s, 3H) , 1.71 (d, J = 7.2Hz, 3H), 1.05-0.80 (m, 6H)
(Isomer ratio 3) 8.84 (d, J = 2.7Hz, 1H), 8.60-8.50 (m, 1H), 8.05-7.95 (m, 1H), 7.76 (s, 1H), 7.35-7.20 (m, 1H ), 6.10-5.90 (m, 2H), 4.25-4.05 (m, 1H), 3.94 (s, 3H), 3.45-3.05 (m, 4H), 1.88 (s, 3H), 1.37 (d, J = 7.2 Hz, 3H), 1.25-1.10 (m, 6H)
6-001;
8.76 (s, 1H), 8.70-8.60 (m, 1H), 8.16 (brs, 1H), 8.05-7.95 (m, 1H), 7.86 (ddd, J = 8.1,2.1,1.2Hz, 1H), 7.46 ( dd, J = 8.1, 4.2Hz, 1H), 4.18-4.02 (m, 4H), 2.34 (s, 3H), 2.17 (s, 3H), 2.15-1.90 (m, 2H), 1.10-0.90 (m, 3H)
6-002;
8.95-8.85 (m, 1H), 8.70-8.60 (m, 1H), 7.91 (dd, J = 8.1,1.5Hz, 1H), 7.50-7.40 (m, 1H), 3.85-3.75 (m, 4H), 3.35-3.20 (m, 3H), 2.40-2.30 (m, 3H), 2.10-1.80 (m, 5H), 1.10-0.90 (m, 3H)
――――――――――――――――――――――――――――――――――
　第１２表のプロトン核磁気共鳴ケミカルシフト値は、基準物質としてＭｅ４Ｓｉ（テトラメチルシラン）を用い、３００ＭＨｚにて測定した。
　本発明化合物の光学活性体の一部は、光学活性カラムを有する高速液体クロマトグラフィーを用いて、光学活性体に分離した。その方法について詳細に説明するが、本発明はこれらにのみ限定されるものではない。
（Ａ）光学活性体の分離
　高速液体クロマトグラフィーは、島津製作所社製；１０ＡＶＰシステムを使用した。
　また以下に記載した条件に従って、光学活性体の分離を行った。
　流速：７．０ｍｌ／ｍｉｎ.　　オーブン温度：４０℃
　移動相：ｎ－ヘキサン：エタノール＝８５：１５（体積比）
　カラム：ダイセル　ＣＨＩＲＡＬＰＡＫ　ＡＤ－Ｈ（内径２０ｍｍ、長さ２５０ｍｍ、粒子径５μｍ）、
　測定波長：２５４ｎｍ
　Ｎ－｛３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル｝－Ｎ－（シアノメチル）－２－（メトキシイミノ）－３－（メチルチオ）ブタンアミド（本発明化合物１－０７１）（６００ｍｇ）をｎ－ヘキサン：エタノール＝９：１（体積比）の混合溶媒２ｍｌに溶解させ、この溶液を０．１ｍｌに分割して、上記に記載した条件下で高速液体クロマトグラフィーにて計１５回分離作業を行い、保持時間３９．５ｍｉｎ.及び保持時間４３．３ｍｉｎ.のピークに相当する画分をそれぞれ分取した。それぞれ分取した画分の溶媒を、減圧下にて留去した後、保持時間３９．５ｍｉｎ.の画分からは、６２．５ｍｇの無色透明油状物｛ [α]D 23.5-41.23゜(CHCl3,c=0.624)｝が、保持時間４３．３ｍｉｎ.の画分からは、６５．８ｍｇの黄色油状物｛ [α]D 23.6+34.88゜(CHCl3,c=0.734)｝がそれぞれ得られた。 The proton nuclear magnetic resonance chemical shift values in Table 12 were measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference substance.
A part of the optically active form of the compound of the present invention was separated into the optically active form using high performance liquid chromatography having an optically active column. The method will be described in detail, but the present invention is not limited to these.
(A) Separation of optically active substance High performance liquid chromatography was manufactured by Shimadzu Corporation; 10AVP system was used.
The optically active substance was separated according to the conditions described below.
Flow rate: 7.0 ml / min. Oven temperature: 40 ° C
Mobile phase: n-hexane: ethanol = 85: 15 (volume ratio)
Column: Daicel CHIRALPAK AD-H (inner diameter 20 mm, length 250 mm, particle diameter 5 μm),
Measurement wavelength: 254 nm
N- {3-Chloro-1- (pyridin-3-yl) -1H-pyrazol-4-yl} -N- (cyanomethyl) -2- (methoxyimino) -3- (methylthio) butanamide (Compound 1 of the present invention) -071) (600 mg) was dissolved in 2 ml of a mixed solvent of n-hexane: ethanol = 9: 1 (volume ratio), and this solution was divided into 0.1 ml and subjected to high performance liquid chromatography under the conditions described above. Separation work was performed 15 times in total, and fractions corresponding to peaks with a retention time of 39.5 min. And a retention time of 43.3 min. Were collected respectively. After the solvent of each fraction was distilled off under reduced pressure, 62.5 mg of a colorless transparent oil {[α] D 23.5 -41.23 ° (CHCl 3 ) was obtained from the fraction having a retention time of 39.5 min. , c = 0.624)}, and 65.8 mg of a yellow oil {[α] D 23.6 + 34.88 ° (CHCl 3 , c = 0.734)} was obtained from the fraction having a retention time of 43.3 min.
（Ｂ）光学純度の決定
　更に得られた目的物を、光学活性カラムを有する高速液体クロマトグラフィーを用いて、光学純度を測定した。
　高速液体クロマトグラフィーは、日本分光社製；ＬＣ－２０００システムを使用した。
　また以下に記載した条件に従って測定を行った。
　流速：０．６ｍｌ／ｍｉｎ.　　オーブン温度：３０℃
　移動相：ｎ－ヘキサン：エタノール＝９：１（体積比）
　カラム：ダイセル　ＣＨＩＲＡＬＰＡＫ　ＡＤ－３（内径２．１ｍｍ、長さ２５０ｍｍ、粒子径５μｍ）、
　測定波長：２５４ｎｍ
　この結果、
<１>保持時間１２．０ｍｉｎ.[上記（Ａ）において保持時間３９．５ｍｉｎ.の画分から得られた６２．５ｍｇの無色透明油状物｛[α]D 23.5-41.23゜(CHCl3,c=0.624)｝]９９．９％（99%e.e.）及び
<２>保持時間１５．３ｍｉｎ.[上記（Ａ）において保持時間４３．３ｍｉｎ.の画分から得られた６５．８ｍｇの黄色油状物｛[α]D 23.6+34.88゜(CHCl3,c=0.734)｝]９８．６％（97.1%e.e.）のピークに相当する画分を検出した。 (B) Determination of optical purity Furthermore, optical purity was measured for the obtained target object using the high performance liquid chromatography which has an optically active column.
For high performance liquid chromatography, LC-2000 system manufactured by JASCO Corporation was used.
The measurement was performed according to the conditions described below.
Flow rate: 0.6 ml / min. Oven temperature: 30 ° C
Mobile phase: n-hexane: ethanol = 9: 1 (volume ratio)
Column: Daicel CHIRALPAK AD-3 (inner diameter 2.1 mm, length 250 mm, particle diameter 5 μm),
Measurement wavelength: 254 nm
As a result,
<1> Retention time 12.0 min. [62.5 mg of a colorless transparent oily substance {[α] D 23.5 -41.23 ° (CHCl 3 , c = 0.624)}] 99.9% (99% ee) and
<2> Retention time 15.3 min. [65.8 mg of yellow oil {[α] D 23.6 + 34.88 ° (CHCl 3 , c = 0.734 obtained from the fraction with retention time 43.3 min. In (A) above) )}] A fraction corresponding to a peak of 98.6% (97.1% ee) was detected.
［試験例］
　次に、本発明化合物の有害生物防除剤としての有用性について、以下の試験例において具体的に説明するが、本発明はこれらのみに限定されるものではない。
試験例１　トビイロウンカに対する殺虫試験
　本発明化合物の１０％乳剤（化合物によっては１０％水和剤を供試）を展着剤の入った水で希釈して、５００ｐｐｍ濃度の薬液を調製した。この薬液中にイネの葉鞘を約１０秒間浸漬し、風乾後試験管に入れ、この中にトビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）の２齢幼虫を試験管当たり５頭放虫し、スポンジで蓋をして２５℃恒温室に収容した。６日後の死虫数を調査し、死虫率(％)(死虫数÷供試虫数×１００)を算出した。尚、試験は２連制で行なった。
　その結果、供試した化合物の内、下記の化合物が９０％以上の死虫率を示した。 [Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.
Test Example 1 Insecticidal test against brown planthopper A 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder) was diluted with water containing a spreading agent to prepare a chemical solution having a concentration of 500 ppm. Rice leaf sheaths are immersed in this chemical solution for about 10 seconds, air-dried and placed in a test tube, and 5 second-instar larvae of the green planthopper (Nilaparvata lugens) are released per test tube and covered with a sponge. Housed in a constant temperature room. The number of dead insects after 6 days was investigated, and the death rate (%) (number of dead insects ÷ number of test insects × 100) was calculated. In addition, the test was performed by 2 continuous systems.
As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
　本発明化合物：１－００１、１－００２、１－００４、１－００６、１－００９～１－０１４、１－０１５、１－０１６、１－０１８～１－０２１、１－０２４、１－０２７～１－０３５、１－０３７、１－０３８、１－０３９、１－０４１～１－０４８、１－０５０～１－１８５、１－１８７～１－１９５、１－１９７～１－２０９、１－２１１～１－２３２～１－２６８、１－２７０～１－２７６、１－２７８～１－２８５、１－２８７～１－３１１、１－３１３～１－３４４、２－００１～２－００４、３－００１～３－００８、３－００９、３－０１０、３－０１１、３－０１２、３－０１３、３－０１４、３－０１６～３－０４２、４－００１、４－００２、５－００１、７－００１、７－００２、１－０１８（＊３）、１－０２０（＊３）、１－０５６（＊３）、１－０５７（＊３）、１－０７７（＊３）、１－０９０（＊３）、１－０９１（＊３）、１－１０５（＊３）、１－１１６（＊３）、１－２１７（＊３）、１－２２８（＊３）、１－２３１（＊３）、１－２９８（＊３）、１－３０４（＊３）、１－３０９（＊３）、３－０３６（＊３）、１－０５６（＋）、１－０５６（-）、１－０５７（＋）、１－０５７（-）、１－１１６（＋）、１－１１６（－）、１－１４１（＋）、１－１４１（－）、３－００５（＋）、３－００５（－）、３－０１６（－）、３－０１８（－） Compounds of the present invention: 1-001, 1-002, 1-004, 1-006, 1-009 to 1-014, 1-015, 1-016, 1-018 to 1-021, 1-024, 1- 027 to 1-035, 1-037, 1-038, 1-039, 1-041 to 1-048, 1-050 to 1-185, 1-187 to 1-195, 1-197 to 1-209, 1-211 to 1-232 to 1-268, 1-270 to 1-276, 1-278 to 1-285, 1-287 to 1-311, 1-313 to 1-344, 2-001 to 2- 004, 3-001 to 3-008, 3-009, 3-010, 3-011, 3-012, 3-013, 3-014, 3-016 to 3-042, 4-001, 4-002, 5-001, 7-001, 7-002, 1-018 (* 3), 1-0 0 (* 3), 1-056 (* 3), 1-057 (* 3), 1-077 (* 3), 1-090 (* 3), 1-091 (* 3), 1-105 ( * 3), 1-116 (* 3), 1-217 (* 3), 1-228 (* 3), 1-231 (* 3), 1-298 (* 3), 1-304 (* 3) ), 1-309 (* 3), 3-036 (* 3), 1-056 (+), 1-056 (-), 1-057 (+), 1-057 (-), 1-116 ( +), 1-116 (-), 1-141 (+), 1-141 (-), 3-005 (+), 3-005 (-), 3-016 (-), 3-018 (- )
試験例２　シルバーリーフコナジラミに対する殺虫試験
　内径７ｃｍのスチロールカップに湿った濾紙を敷き、その上に３ｃｍに切り取ったインゲンの葉を置いた。本発明化合物の１０％乳剤（化合物によっては１０％水和剤を供試）を展着剤の入った水で希釈して、５００ｐｐｍ濃度の薬液を調製し、回転式散布塔を用いて薬液をスチロールカップ当たり２．５ｍｌずつ散布した（２．５ｍｇ／ｃｍ２）。葉を風乾後、シルバーリーフコナジラミ（Ｂｅｍｉｓｉａ　ａｒｇｅｎｔｉｆｏｌｉｉ）の成虫を放虫し、蓋をして２５℃恒温室に収容した。５日後の死虫数を調査し、試験例１と同様の計算式から死虫率を算出した。尚、試験は２連制で行なった。
　その結果、供試した化合物の内、下記の化合物が９０％以上の死虫率を示した。 Test Example 2 Insecticidal test against silver leaf whitefly A moist filter paper was laid on a 7 cm inner diameter styrol cup, and a green leaf cut into 3 cm was placed thereon. A 10% emulsion of a compound of the present invention (depending on the compound, 10% wettable powder) is diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm, and the chemical solution is prepared using a rotary spray tower. 2.5 ml was sprayed per styrene cup (2.5 mg / cm 2 ). After the leaves were air-dried, adults of silver leaf whiteflies (Bemisia argentifolii) were released, covered, and housed in a thermostatic chamber at 25 ° C. The number of dead insects after 5 days was investigated, and the dead insect rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.
As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
本発明化合物：１－００２、１－０１０、１－０１１、１－０１２、１－０１５、１－０１９、１－０２１、１－０２４、１－０２６～１－０３４、１－０３７、１－０３８、１－０３９、１－０４１～１－０５３、１－０５５、１－０５６、１－０５７、１－０５９、１－０６１、１－０６２、１－０６５、１－０６６、１－０６８、１－０６９、１－０７１～１－０７７、１－０７９、１－０８１～１－０８８、１－０９０～１－０９３、１－０９５～１－０９８、１－１０２～１－１０７、１－１０９、１－１１１、１－１１２、１－１１３、１－１１５～１－１４５、１－１４７～１－１５１、１－１５４、１－１５５、１－１５６、１－１５８～１－１８５、１－１８７～１－１９２、１－１９４、１－１９５、１－１９８、１－１９９、１－２０１、１－２０２、１－２０４、１－２０６～１－２０９、１－２１１、１－２１２、１－２１３、１－２１４、１－２１６～１－２２０、１－２２２、１－２２３、１－２２５、１－２２６、１－２２８～１－２３０、１－２３２、１－２３３、１－２３６、１－２３９、１－２４０、１－２４２、１－２４４～１－２５０、１－２５２、１－２５３、１－２５６～１－２６２、１－２６４、１－２６５、１－２６６、１－２６８、１－２７０～１－２７４、１－２７８、１－２７９、１－２８１～１－２８５、１－２８７～１－２８９、１－２９２、１－２９３、１－２９６、１－３０５、１－３０６、１－３０９、１－３１０、１－３１３～１－３１６、１－３１９、１－３２０、１－３２２、１－３２４～１－３２６、１－３２８、１－３３０、１－３３１～１－３４４、２－００１～２－００４、３－００２、３－００４～３－００８、３－０１０、３－０１２、３－０１３、３－０１４、３－０１６～３－０２９、３－０３１、３－０３２、３－０３４、３－０４０、４－００１、４－００２、５－００１、７－００１、７－００２、１－０５６（＊３）、１－０５７（＊３）、１－０７７（＊３）、１－０９０（＊３）、１－０９１（＊３）、１－１０５（＊３）、１－１１６（＊３）、１－２１７（＊３）、１－２２８（＊３）、１－３０９（＊３）、１－０５６（＋）、１－０５６（-）、１－０５７（＋）、１－０５７（-）、１－１１６（＋）、１－１１６（－）、１－１４１（＋）、１－１４１（－）、１－００５（＋）、１－００５（－）、１－０１６（－）、１－０１８（－）、３－００５（＋）、３－００５（－）、３－０１６（－）、３－０１８（－） Compounds of the present invention: 1-002, 1-010, 1-011, 1-012, 1-015, 1-019, 1-021, 1-024, 1-026 to 1-034, 1-037, 1- 038, 1-039, 1-041 to 1-053, 1-055, 1-056, 1-057, 1-059, 1-061, 1-062, 1-065, 1-066, 1-068, 1-069, 1-071 to 1-077, 1-079, 1-081 to 1-088, 1-090 to 1-093, 1-095 to 1-098, 1-102 to 1-107, 1- 109, 1-111, 1-112, 1-113, 1-115 to 1-145, 1-147 to 1-151, 1-154, 1-155, 1-156, 1-158 to 1-185, 1-187 to 1-192, 1-194, 1-195, 1-198, 1- 99, 1-201, 1-202, 1-204, 1-206 to 1-209, 1-211, 1-212, 1-213, 1-214, 1-216 to 1-220, 1-222, 1-223, 1-225, 1-226, 1-228 to 1-230, 1-232, 1-233, 1-236, 1-239, 1-240, 1-242, 1-244 to 1- 250, 1-252, 1-253, 1-256 to 1-262, 1-264, 1-265, 1-266, 1-268, 1-270 to 1-274, 1-278, 1-279, 1-281-1-285, 1-287-1-289, 1-292, 1-293, 1-296, 1-305, 1-306, 1-309, 1-310, 1-313-1- 316, 1-319, 1-320, 1-322, 1-324 to 1-326 1-328, 1-330, 1-331-1 to 344, 2-001 to 2-004, 3-002, 3-004 to 3-008, 3-010, 3-012, 3-013, 3- 014, 3-016 to 3-029, 3-031, 3-032, 3-034, 3-040, 4-001, 4-002, 5-001, 7-001, 7-002, 1-056 ( * 3), 1-057 (* 3), 1-077 (* 3), 1-090 (* 3), 1-091 (* 3), 1-105 (* 3), 1-116 (* 3) ), 1-217 (* 3), 1-228 (* 3), 1-309 (* 3), 1-056 (+), 1-056 (-), 1-057 (+), 1-057 (−), 1-116 (+), 1-116 (−), 1-141 (+), 1-141 (−), 1-005 (+), 1-005 (−), -016 (-), 1-018 (-), 3-005 (+), 3-005 (-), 3-016 (-), 3-018 (-)
試験例３　モモアカアブラムシに対する殺虫試験
　内径３ｃｍのガラスシャーレに湿った脱脂綿を敷き、その上に同径に切り取ったカンランの葉を置き、モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）無翅成虫を４頭放虫した。１日後、本発明化合物の１０％乳剤（化合物によっては１０％水和剤を供試）を展着剤の入った水で希釈して、５００ｐｐｍ濃度の薬液を調製し、回転式散布塔にて薬液を散布（２．５ｍｇ／ｃｍ２）、蓋をして２５℃恒温室に収容した。６日後の死虫数を調査し、試験例１と同様の計算式から死虫率を算出した。尚、試験は２連制で行なった。
　その結果、供試した化合物の内、下記の化合物が９０％以上の死虫率を示した。 Test Example 3 Insecticidal test against peach aphid A moist absorbent cotton was laid on a glass petri dish with an inner diameter of 3 cm, and kanran leaves cut out to the same diameter were placed on it. did. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 500 ppm. The chemical solution was sprayed (2.5 mg / cm 2 ), covered, and stored in a constant temperature room at 25 ° C. The number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.
As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
本発明化合物：１－００１～１－００４、１－００６～１－０２４、１－０２６～１－１８５、１－１８７～１－１９２、１－１９４、１－１９５、１－１９７～１－２２３、１－２２５～１－２５３、１－２５５～１－３４４、２－００１～２－００４、３－００１～３－００８、３－００９、３－０１０、３－０１２、３－０１３、３－０１４、３－０１６～３－０４２、４－００１、４－００２、５－００１、７－００１、７－００２、１－０１４（＊３）、１－０１８（＊３）、１－０２０（＊３）、１－０５６（＊３）、１－０５７（＊３）、１－０７７（＊３）、１－０９０（＊３）、１－０９１（＊３）、１－１０５（＊３）、１－１１６（＊３）、１－２１７（＊３）、１－２２８（＊３）、１－２３１（＊３）、１－２９８（＊３）、１－３０４（＊３）、１－３０９（＊３）、３－０３６（＊３）、１－０５６（＋）、１－０５６（-）、１－０５７（＋）、１－０５７（-）、１－１１６（＋）、１－１１６（－）、１－１４１（＋）、１－１４１（－）、３－００５（＋）、３－００５（－）、３－０１６（－）、３－０１８（－） Compounds of the present invention: 1-001 to 1-004, 1-006 to 1-024, 1-026 to 1-185, 1-187 to 1-192, 1-194, 1-195, 1-197 to 1- 223, 1-225 to 1-253, 1-255 to 1-344, 2-001 to 2-004, 3-001 to 3-008, 3-009, 3-010, 3-012, 3-013, 3-014, 3-016 to 3-042, 4-001, 4-002, 5-001, 7-001, 7-002, 1-014 (* 3), 1-018 (* 3), 1- 020 (* 3), 1-056 (* 3), 1-057 (* 3), 1-077 (* 3), 1-090 (* 3), 1-091 (* 3), 1-105 ( * 3), 1-116 (* 3), 1-217 (* 3), 1-228 (* 3), 1-231 (* 3), 1-29 (* 3), 1-304 (* 3), 1-309 (* 3), 3-036 (* 3), 1-056 (+), 1-056 (-), 1-057 (+), 1-057 (-), 1-116 (+), 1-116 (-), 1-141 (+), 1-141 (-), 3-005 (+), 3-005 (-), 3 -016 (-), 3-018 (-)
試験例４　ワタアブラムシに対する殺虫試験
　内径３ｃｍのガラスシャーレに湿った脱脂綿を敷き、その上に同径に切り取ったキュウリの葉を置き、ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）無翅成虫を４頭放虫した。１日後、本発明化合物の１０％乳剤（化合物によっては１０％水和剤を供試）を展着剤の入った水で希釈して、１００ｐｐｍ濃度の薬液を調製し、回転式散布塔にて薬液を散布（２．５ｍｇ／ｃｍ２）、蓋をして２５℃恒温室に収容した。６日後の死虫数を調査し、試験例１と同様の計算式から死虫率を算出した。尚、試験は２連制で行なった。
　その結果、供試した化合物の内、下記の化合物が９０％以上の死虫率を示した。 Test Example 4 Insecticidal test against cotton aphids Wet cotton wool with a 3 cm inner diameter petri dish, and a cucumber leaf cut to the same diameter was placed on it, and four cotton aphids (Aphis gossypii) adults were released. One day later, a 10% emulsion of the compound of the present invention (depending on the compound, 10% wettable powder was tested) was diluted with water containing a spreading agent to prepare a chemical solution with a concentration of 100 ppm. The chemical solution was sprayed (2.5 mg / cm 2 ), covered, and stored in a constant temperature room at 25 ° C. The number of dead insects after 6 days was investigated, and the death rate was calculated from the same calculation formula as in Test Example 1. In addition, the test was performed by 2 continuous systems.
As a result, among the compounds tested, the following compounds showed a death rate of 90% or more.
本発明化合物：１－００１、１－００２、１－００６～１－０２１、１－０２６～１－０３５、１－０３７～１－０５７、１－０５９～１－１１１、１－１１３、１－１１５～１－１１９、１－１２１～１－１４５、１－１４７～１－１５７、１－１５９～１－１８５、１－１８７～１－１９２、１－１９４、１－１９７、１－１９８、１－２０１～１－２２３、１－２２５～１－２５０、１－２５２、１－２５３、１－２５５～１－２８９、１－２９１～１－３４４、２－００１～２－００４、３－００１～３－００８、３－００９、３－０１０、３－０１２、３－０１３、３－０１４、３－０１６～３－０２９、３－０３１～３－０４２、４－００１、４－００２、５－００１、７－００１、７－００２、１－０１４（＊３）、１－０１８（＊３）、１－０２０（＊３）、１－０５６（＊３）、１－０５７（＊３）、１－０７７（＊３）、１－０９０（＊３）、１－０９１（＊３）、１－１０５（＊３）、１－１１６（＊３）、１－２１７（＊３）、１－２２８（＊３）、１－２３１（＊３）、１－２９８（＊３）、１－３０４（＊３）、１－３０９（＊３）、３－０３６（＊３）、１－０５６（＋）、１－０５６（-）、１－０５７（＋）、１－０５７（-）、１－１１６（＋）、１－１１６（－）、１－１４１（＋）、１－１４１（－）、３－００５（＋）、３－００５（－）、３－０１６（－）、３－０１８（－） Compounds of the present invention: 1-001, 1-002, 1-006 to 1-021, 1-026 to 1-035, 1-037 to 1-057, 1-059 to 1-111, 1-113, 1- 115 to 1-119, 1-121 to 1-145, 1-147 to 1-157, 1-159 to 1-185, 1-187 to 1-192, 1-194, 1-197, 1-198, 1-201 to 1-223, 1-225 to 1-250, 1-252, 1-253, 1-255 to 1-289, 1-291 to 1-344, 2-001 to 2-004, 3- 001 to 3-008, 3-009, 3-010, 3-012, 3-013, 3-014, 3-016 to 3-029, 3-031 to 3-042, 4-001, 4-002, 5-001, 7-001, 7-002, 1-014 (* 3), 1-01 (* 3), 1-020 (* 3), 1-056 (* 3), 1-057 (* 3), 1-077 (* 3), 1-090 (* 3), 1-091 (* 3), 1-105 (* 3), 1-116 (* 3), 1-217 (* 3), 1-228 (* 3), 1-231 (* 3), 1-298 (* 3) 1-304 (* 3), 1-309 (* 3), 3-036 (* 3), 1-056 (+), 1-056 (-), 1-057 (+), 1-057 ( -), 1-116 (+), 1-116 (-), 1-141 (+), 1-141 (-), 3-005 (+), 3-005 (-), 3-016 (- ), 3-018 (-)
試験例５　モモアカアブラムシに対する土壌潅注処理試験
　本発明化合物の１０％乳剤を水道水で希釈して、濃度が１００ｐｐｍの薬液を調製した。
　プラスチックカップ植えキャベツ苗（２．５本葉期）の株元土壌部分に１０ｍｌの薬液を潅注処理し、温室内に放置した。潅注処理１日後にモモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）の成虫を２０頭／株で放虫し、その後温室内に放置した。放虫６日後の生存虫数を調査し、下記の計算式から対照値を算出した。
対照値（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
式中の文字は下記を表している。
　Ｃｂ：無処理区における処理前の虫の数
　Ｃａｉ：無処理区における最終調査時の生存虫数
　Ｔｂ：処理区における処理前の虫の数
　Ｔａｉ：処理区における最終調査時の生存虫数
　その結果、供試した化合物の内、下記の化合物が９０％以上の対照値を示した。 Test Example 5 Soil irrigation treatment test for peach aphid A 10% emulsion of the compound of the present invention was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm.
10 ml of the chemical solution was irrigated to the stock soil portion of the plastic cup planted cabbage seedling (2.5 true leaf stage) and left in the greenhouse. One day after the irrigation treatment, 20 mosquitoes / strain of adult peach aphid (Myzus persicae) were released and then left in the greenhouse. The number of surviving insects 6 days after the release was examined, and a control value was calculated from the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
The characters in the formula represent the following:
Cb: Number of insects before treatment in the untreated group Cai: Number of live insects at the time of final survey in the untreated group Tb: Number of insects before treatment in the treated group Tai: Number of live insects at the time of final survey in the treated group Results Among the compounds tested, the following compounds showed a control value of 90% or more.
本発明化合物：１－００１、１－００２、１－０１０、１－０１１、１－０１２、１－０１７、１－０１８、１－０１９、１－０２７～１－０３４、１－０３８、１－０４１～１－０４６、１－０４８、１－０４９、１－０５６～１－０５９、１－０６１、１－０６２、１－０６３、１－０６５、１－０６６、１－０６８、１－０７２～１－０７７、１－０７９、１－０８１～１－０９１、１－０９５～１－０９８、１－１０２～１－１０７、１－１１３、１－１１５～１－１１９、１－１２１、１－１２２、１－１２４～１－１２７、１－１３０、１－１３１、１－１３３、１－１３５～１－１３９、１－１４１、１－１５５、１－１５６、１－１６０、１－１６１、１－１６３、１－１６４、１－１６８、１－１６９、１－１７２、１－１７３、１－１７４、１－１７９、１－１８１、１－１８５、１－１８８、１－１９１、１－１９９、１－２０１、１－２０２、１－２１１、１－２１３、１－２２３、１－２２５、１－２２８～１－２３０、１－２４０、１－２４６、１－２５９、１－２６２、１－２６４、１－２６６、１－２６７、１－２７０、１－２７１、１－２７８、１－２８５、１－２８７、１－２９２、１－３０２、１－３０３、１－３０４、１－３０５、１－３１５、１－３１６、１－３２３、１－３２４、１－３２６、１－３３２、１－３４０、１－３４１、１－３４３、２－００１～２－００４、３－００１、３－００２、３－００３、３－００４～３－００８、３－０１０、３－０１２、３－０１３、３－０１４、３－０１６、３－０１８、３－０１９、３－０２０、３－０３１、３－０３４、４－００１、７－００１、７－００２、１－０５６（＊３）、１－０５７（＊３）、１－０７７（＊３）、１－０９０（＊３）、１－０９１（＊３）、１－１０５（＊３）、１－１１６（＊３）、１－２２８（＊３）、１－０５６（＋）、１－０５６（-）、１－０５７（＋）、１－０５７（-）、１－１１６（＋）、１－１１６（－）、１－１４１（＋）、１－１４１（－）、３－００５（＋）、３－００５（－）、３－０１６（－）、３－０１８（－） Compounds of the present invention: 1-001, 1-002, 1-010, 1-011, 1-012, 1-017, 1-018, 1-019, 1-027 to 1-034, 1-038, 1- 041 to 1-046, 1-048, 1-049, 1-056 to 1-059, 1-061, 1-062, 1-063, 1-065, 1-066, 1-068, 1-072 1-077, 1-079, 1-081 to 1-091, 1-095 to 1-098, 1-102 to 1-107, 1-113, 1-115 to 1-119, 1-121, 1- 122, 1-124 to 1-127, 1-130, 1-131, 1-133, 1-135 to 1-139, 1-141, 1-155, 1-156, 1-160, 1-161, 1-163, 1-164, 1-168, 1-169, 1-172, 1- 73, 1-174, 1-179, 1-181, 1-185, 1-188, 1-191, 1-199, 1-201, 1-202, 1-211, 1-213, 1-223, 1-225, 1-228 to 1-230, 1-240, 1-246, 1-259, 1-262, 1-264, 1-266, 1-267, 1-270, 1-271, 1- 278, 1-285, 1-287, 1-292, 1-302, 1-303, 1-304, 1-305, 1-315, 1-316, 1-323, 1-324, 1-326, 1-332, 1-340, 1-341, 1-343, 2-001 to 2-004, 3-001, 3-002, 3-003, 3-004 to 3-008, 3-010, 3- 012, 3-013, 3-014, 3-016, 3-018, 3-019 3-020, 3-031, 3-034, 4-001, 7-001, 7-002, 1-056 (* 3), 1-057 (* 3), 1-077 (* 3), 1- 090 (* 3), 1-091 (* 3), 1-105 (* 3), 1-116 (* 3), 1-228 (* 3), 1-056 (+), 1-056 (- ), 1-057 (+), 1-057 (-), 1-116 (+), 1-116 (-), 1-141 (+), 1-141 (-), 3-005 (+) , 3-005 (-), 3-016 (-), 3-018 (-)
試験例６　ネコノミ(Cat flea)に対する効果試験
　本発明化合物３.５ｍｇを３.５ｍｌのアセトンに溶解し、１０００ｐｐｍ濃度の薬液を調製した。この薬液３５０μｌを内壁表面積３５ｃｍ２のガラス製容器の底面と側面とに塗布した後、アセトンを揮発させてピラゾール及びチアゾール誘導体の薄膜をガラス容器内壁に作製した。用いたガラス容器の内壁は３５ｃｍ２なので、処理薬量は１０μｇ／ｃｍ２となる。これにネコノミ(Ctenocephalides felis)成虫（雌雄混合）を５頭放虫し、蓋をして２５℃の恒温室に収容した。４日後に行動異常が認められた虫数を調査し、下記の計算式からefficacy（％）を算出した。尚、試験は２連制で行なった。
　efficacy（％）＝（化合物由来の行動異常が認められた虫数／放虫数）×１００
　その結果、供試した化合物の内、下記の化合物が８０％以上のefficacy（％）を示した。 Test Example 6 Effect test on cat fleas 3.5 mg of the compound of the present invention was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 μl of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm 2 , acetone was volatilized to form a pyrazole and thiazole derivative thin film on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm 2 , the treatment dose is 10 μg / cm 2 . Five cat fleas (Ctenocephalides felis) adults (mixed males and females) were released on this, covered, and housed in a thermostatic chamber at 25 ° C. After 4 days, the number of insects with behavioral abnormalities was investigated, and the efficiency (%) was calculated from the following formula. In addition, the test was performed by 2 continuous systems.
efficacy (%) = (number of insects with behavioral abnormalities derived from compounds / number of worms) × 100
As a result, among the compounds tested, the following compounds showed an efficiency (%) of 80% or more.
本発明化合物：１－００１、１－００４、１－００７、１－０１０、１－０１１、１－０１２、１－０１４、１－０１５、１－０１６、１－０１７、１－０１９、１－０２１、１－０２４、１－０２６、１－０２７、１－０２８、１－０２９、１－０３０、１－０３１、１－０３２、１－０３３、１－０３４、１－０３５、１－０３６、１－０３７、１－０３８、１－０３９、１－０４０、１－０４１、１－０４２、１－０４３、１－０４４、１－０４５、１－０４６、１－０４７、１－０４８、１－０４９、１－０５０、１－０５１、１－０５２、１－０５３、１－０５４、１－０５５、１－０５６、１－０５９、１－０６６、１－０６８、１－０６９、１－０７０、１－０７１、１－０７２、１－０７４、１－０７７、１－０７９、１－０８１、１－０８２、１－０８３、１－０８５、１－０８６、１－０８７、１－０８８、１－０８９、１－０９４、１－０９５、１－０９６、１－０９７、１－０９９、１－１００、１－１０１、１－１０２、１－１０３、１－１０４、１－１０５、１－１０６、１－１０７、１－１０８、１－１０９、１－１１０、１－１１３、１－１１５、１－１１７、１－１１８、１－１２１、１－１２３、１－１２４、１－１２６、１－１２９、１－１３１、１－１３３、１－１３６、１－１３７、１－１３９、１－１４６、１－１４７、１－１４８、１－１５０、１－１５１、１－１５２、１－１５３、１－１５４、１－１５５、１－１５６、１－１５７、１－１６１、１－１６４、１－１６６、１－１６９、１－１７１、１－１７４、１－１７５、１－１７６、１－１７７、１－１７９、１－１８１、１－１８４、１－１８６、１－１８７、１－１８９、１－１９０、１－１９１、１－１９２、１－１９３、１－１９４、１－１９７、１－１９９、１－２００、１－２０１、１－２０２、１－２０３、１－２０４、１－２０５、１－２０６、１－２０７、１－２０８、１－２０９、１－０１４（＊３）、１－０５６－（＋）、１－０５７－（＋）、１－０５７（＊３）１－０７７（＊３）、１－１１６（－）、１－１４１（－） Compounds of the present invention: 1-001, 1-004, 1-007, 1-010, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017, 1-019, 1- 021, 1-024, 1-026, 1-027, 1-028, 1-029, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1-044, 1-045, 1-046, 1-047, 1-048, 1- 049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-059, 1-066, 1-068, 1-069, 1-070, 1-071, 1-072, 1-074, 1-077, 1-079, 1- 81, 1-082, 1-083, 1-085, 1-086, 1-087, 1-088, 1-089, 1-094, 1-095, 1-096, 1-097, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-113, 1- 115, 1-117, 1-118, 1-121, 1-123, 1-124, 1-126, 1-129, 1-131, 1-133, 1-136, 1-137, 1-139, 1-146, 1-147, 1-148, 1-150, 1-151, 1-152, 1-153, 1-154, 1-155, 1-156, 1-157, 1-161, 1- 164, 1-166, 1-169, 1-171, 1-174, 1-175 1-176, 1-177, 1-179, 1-181, 1-184, 1-186, 1-187, 1-189, 1-190, 1-191, 1-192, 1-193, 1- 194, 1-197, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-014 (* 3), 1-056-(+), 1-057-(+), 1-057 (* 3) 1-077 (* 3), 1-116 (-), 1-141 ( -)
試験例７　マダニ(American dog tick)に対する効果試験
　本発明化合物３.５ｍｇを３.５ｍｌのアセトンに溶解し、１０００ｐｐｍ濃度の薬液を調製した。この薬液３５０μｌを内壁表面積３５ｃｍ２のガラス製容器の底面と側面とに塗布した後、アセトンを揮発させてピラゾール及びチアゾール誘導体の薄膜をガラス容器の内壁に作製した。用いたガラス容器の内壁は３５ｃｍ２なので、処理薬量は１０μｇ／ｃｍ２となる。これにAmerican dog tick(Dermacentor variabilis)第１若虫（雌雄混合）を５頭放虫し、蓋をして２５℃の恒温室に収容した。４日後に行動異常が認められた虫数を調査し、試験例６と同様の計算式からefficacy（％）を算出した。尚、試験は２連制で行なった。
　その結果、供試した化合物の内、下記の化合物が８０％以上のefficacy(%)を示した。
　本発明化合物：１－０５６、１－０５９、１－１１５、１－１４６、１－１７１、１－１８７、１－１９７、１－１４１（－） Test Example 7 Effect test on tick (American dog tick) 3.5 mg of the compound of the present invention was dissolved in 3.5 ml of acetone to prepare a chemical solution having a concentration of 1000 ppm. After 350 μl of this chemical solution was applied to the bottom and side surfaces of a glass container having an inner wall surface area of 35 cm 2 , acetone was volatilized to form a pyrazole and thiazole derivative thin film on the inner wall of the glass container. Since the inner wall of the used glass container is 35 cm 2 , the treatment dose is 10 μg / cm 2 . Five American dog tick (Dermacentor variabilis) first nymphs (mixed males and females) were released, covered, and housed in a thermostatic chamber at 25 ° C. The number of insects in which behavioral abnormalities were observed after 4 days was investigated, and the efficiency (%) was calculated from the same calculation formula as in Test Example 6. In addition, the test was performed by 2 continuous systems.
As a result, among the compounds tested, the following compounds showed an efficiency (%) of 80% or more.
Compounds of the present invention: 1-056, 1-059, 1-115, 1-146, 1-171, 1-187, 1-197, 1-141 (−)
　本発明における新規なピラゾール及びチアゾール誘導体は、優れた有害生物防除活性、特に殺虫・殺ダニ活性を示し、且つ、ホ乳動物、魚類及び益虫等の非標的生物に対してほとんど悪影響の無い、極めて有用な化合物である。 The novel pyrazole and thiazole derivatives in the present invention exhibit excellent pest control activity, particularly insecticidal / miticidal activity, and have almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects. It is a useful compound.
　なお、２０１２年７月６日に出願された日本特許出願２０１２－１５２７５５号、２０１２年８月８日に出願された日本特許出願２０１２－１７５９０６号、２０１２年８月１５日に出願された日本特許出願２０１２－１８０２１７号、２０１２年１０月５日に出願された日本特許出願２０１２－２２３６２６号、２０１２年１１月１６日に出願された日本特許出願２０１２－２５２１３７号、２０１２年１２月４日に出願された日本特許出願２０１２－２６５３８０号、２０１２年１２月２７日に出願された日本特許出願２０１２－２８５６４８号、２０１３年１月１８日に出願された日本特許出願２０１３－００７７０３号、及び２０１３年６月１１日に出願された日本特許出願２０１３－１２２６８１号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。 Japanese Patent Application No. 2012-152755 filed on July 6, 2012, Japanese Patent Application No. 2012-175906 filed on August 8, 2012, Japanese Patent Application filed on August 15, 2012 Application 2012-180217, Japanese Patent Application 2012-223626 filed on October 5, 2012, Japanese Patent Application 2012-252137 filed November 16, 2012, filed December 4, 2012 Japanese Patent Application No. 2012-265380, Japanese Patent Application No. 2012-285648 filed on December 27, 2012, Japanese Patent Application No. 2013-007703 filed on January 18, 2013, and June 2013 Japanese Patent Application No. 2013-122681 filed on May 11th, the claims, The entire contents of the fine abstract quoted herein, as disclosed in the specification of the present invention is intended to incorporate.

Claims (17)

  1. 　式（１）で表されるピラゾール若しくはチアゾール誘導体又はその塩。
    Figure JPOXMLDOC01-appb-C000001
     ［式中、Ａ１は、－Ｎ（－Ｏ）ｍ２又は－ＣＲ１を表し、
    　Ｒ１、Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９ａ）Ｒ３０ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ２は、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２８ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９ａ）Ｒ３０ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表し、ｎが２以上の整数を表すとき、各々のＲ２は互いに同一であっても又は互いに相異なってもよい。
    　Ｂは、Ｂ－１又はＢ－２のいずれかで示される環を表す。
    Figure JPOXMLDOC01-appb-C000002
     （式中、「＊」は置換基「－Ｎ（Ｒａ）Ｒｂ」との結合位置を表し、「＊＊」は下記に示した置換基との結合位置を表す。）
    Figure JPOXMLDOC01-appb-C000003
     　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－ＯＲ６ａ、－Ｓ（Ｏ）ｒ２Ｒ６ａ、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）ＳＲ６ａ、－Ｃ（Ｓ）ＯＲ６ａ、－Ｃ（Ｓ）ＳＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｓ）Ｒ７ａ、－Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ８ａ）Ｒ９ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、ＲａはＲ３と一緒になってＣ２～Ｃ５のアルキレン鎖又はＣ２～Ｃ５アルケニレン鎖を形成することにより、Ｒａが結合する炭素原子及びＲ３が結合する炭素原子と共に５～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、－ＯＨ，－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１１ａ、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表すか、或いは、ＲｂはＲａと一緒になって＝Ｃ（Ｒｂ２）Ｒｂ３を形成してもよく、
    　Ｒｂ２は、－ＯＲ６ａ又は－Ｓ（Ｏ）ｒ２Ｒ６ａを表し、
    　Ｒｂ３は、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂ又は－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表し、
    　Ｒ５ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＨ、－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）ＳＲ１１ａ、－Ｃ（Ｓ）ＯＲ１１ａ、－Ｃ（Ｓ）ＳＲ１１ａ、－Ｃ（Ｏ）Ｒ１２ａ、－Ｃ（Ｓ）Ｒ１２ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｓ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、２つのＲ５ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｒ６ａ、Ｒ８ａ及びＲ９ａは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１０ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１０ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１０ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）ＳＲ１１ａ、－Ｃ（Ｓ）ＯＲ１１ａ、－Ｃ（Ｓ）ＳＲ１１ａ、－Ｃ（Ｏ）Ｒ１２ａ、－Ｃ（Ｓ）Ｒ１２ａ、－Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｃ（Ｓ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１３ａ）Ｒ１４ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ８ａはＲ９ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ８ａ及びＲ９ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つ、Ｒ４２、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒ７ａは、Ｒ６ａ、－Ｃ（＝ＮＲ１３ａ）Ｒ１２ａ、－Ｃ（＝ＮＯＨ）Ｒ１２ａ、－Ｃ（＝ＮＯＲ１１ａ）Ｒ１２ａ又は－Ｃ｛＝ＮＮ（Ｒ１３ａ）Ｒ１４ａ｝Ｒ１２ａを表し、
    　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂ又は－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表し、
    　Ｒ１０ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１１ａ、－ＳＨ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１０ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｒ１１ａ及びＲ１２ａは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ２Ｒ１６ａ、－Ｃ（Ｏ）ＯＲ１６ａ、－Ｃ（Ｏ）ＳＲ１６ａ、－Ｃ（Ｓ）ＯＲ１６ａ、－Ｃ（Ｓ）ＳＲ１６ａ、－Ｃ（Ｏ）Ｒ１７ａ、－Ｃ（Ｓ）Ｒ１７ａ、－Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｃ（Ｏ）Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｃ（Ｓ）Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｓ（Ｏ）ｒ２Ｎ（Ｒ１８ａ）Ｒ１９ａ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ１１ｂは、Ｃ１～Ｃ１０アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ１２ｂは、水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）ＳＲ１６ｃ、－Ｃ（Ｓ）ＯＲ１６ｃ、－Ｃ（Ｓ）ＳＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｓ）Ｒ１７ｃ、－Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｓ（Ｏ）ｒＮ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（＝ＮＯＨ）Ｒ１７ｃ、－Ｃ（＝ＮＯＲ１６ｃ）Ｒ１７ｃ、－Ｃ｛＝ＮＮ（Ｒ１８ｃ）Ｒ１９ｃ｝Ｒ１７ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ１３ａ及びＲ１４ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表すか、或いは、Ｒ１３ａはＲ１４ａと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ａ及びＲ１４ａが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＲ４２、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒ１３ｂは、水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つＲ４２、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒ１４ｂは、水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｄで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｄで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｄで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｄで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｄで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｄ、－Ｓ（Ｏ）ｒ３Ｒ１６ｄ、－Ｃ（Ｏ）ＯＲ１６ｄ、－Ｃ（Ｏ）ＳＲ１６ｄ、－Ｃ（Ｓ）ＯＲ１６ｄ、－Ｃ（Ｓ）ＳＲ１６ｄ、－Ｃ（Ｏ）Ｒ１７ｄ、－Ｃ（Ｓ）Ｒ１７ｄ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｄ）Ｒ１９ｄ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよい。
    　Ｒ１４ｅ及びＲ１４ｆは、各々独立して水素原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓ（Ｏ）ｒ３Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１４ｅはＲ１４ｆと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１４ｅ及びＲ１４ｆが結合する炭素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１、２又は３個含んでもよく、且つＲ４２、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒ１５ａは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ａ、－ＳＨ、－Ｓ（Ｏ）ｒ2Ｒ１６ａ、－Ｓ（＝ＮＲ１８ａ）Ｒ１６ａ、－Ｓ（Ｏ）（＝ＮＲ１８ａ）Ｒ１６ａ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ａが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｒ１５ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｂ、－ＳＨ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｓ（＝ＮＲ１８ｂ）Ｒ１６ｂ、－Ｓ（Ｏ）（＝ＮＲ１８ｂ）Ｒ１６ｂ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（＝ＮＯＲ１６ｂ）Ｒ１７ｂ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｂが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｒ１５ｃは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｓ（＝ＮＲ１８ｃ）Ｒ１６ｃ、－Ｓ（Ｏ）（＝ＮＲ１８ｃ）Ｒ１６ｃ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｃが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｒ１５ｄは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、－ＯＨ、－ＯＲ１６ｄ、－ＳＨ、－Ｓ（Ｏ）ｒ３Ｒ１６ｄ、－Ｓ（＝ＮＲ１８ｄ）Ｒ１６ｄ、－Ｓ（Ｏ）（＝ＮＲ１８ｄ）Ｒ１６ｄ、－Ｐ（Ｏ）（ＯＲ４１）２、－Ｐ（Ｓ）（ＯＲ４１）２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、Ｄ１－１～Ｄ１－９９のいずれかの基又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表すか、或いは、２つのＲ１５ｄが同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよく、
    　Ｒ１６ａ、Ｒ１６ｂ、Ｒ１６ｃ及びＲ１６ｄは、各々独立してシアノ、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｓ（Ｏ）ｒＲ２１、－Ｃ（Ｏ）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ１７ａ、Ｒ１７ｂ、Ｒ１７ｃ及びＲ１７ｄは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル、又はＤ１－１～Ｄ１－９９のいずれかの基を表す。
    　Ｒ１８ａ及びＲ１９ａは、各々独立して水素原子，シアノ又はＣ１～Ｃ６アルキルを表し、
    　Ｒ１８ｂ、Ｒ１９ｂ、Ｒ１８ｄ及びＲ１９ｄは、各々独立して水素原子，シアノ、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、フェニル、（Ｚ）ｑによって置換されたフェニル、ナフチル、（Ｚ）ｑによって置換されたナフチル又はＤ１－１～Ｄ１－９９のいずれかの基を表すか、或いは、Ｒ１８ｂはＲ１９ｂと一緒になってＣ２～Ｃ７のアルキレン鎖又はＣ２～Ｃ７のアルケニレン鎖を形成することにより、Ｒ１８ｂ及びＲ１９ｂが結合する窒素原子と共に３～８員環を形成してもよく、このときこのアルキレン鎖又はアルケニレン鎖は酸素原子、硫黄原子又は窒素原子を１又は２個含んでもよく、且つＲ４２、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、オキソ基又はチオキソ基によって任意に置換されてもよい。
    　Ｒ１８ｃ及びＲ１９ｃは、各々独立して水素原子，シアノ、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－ＯＲ２１、－Ｓ（Ｏ）ｒＲ２１、－Ｃ（Ｏ）ＯＲ２１、－Ｃ（Ｏ）Ｒ２２、－Ｃ（Ｓ）Ｒ２２、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
    　Ｒ２０は、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＲ２１、フェニル又は（Ｚ）ｑによって置換されたフェニルを表すか、或いは、２つのＲ２０が同一の炭素上に置換している場合、２つのＲ５ａは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよく、
    　Ｒ２１及びＲ２２は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６ハロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
    　Ｄ１－1～Ｄ１－９９は、それぞれ以下の構造で表される環を表す。
    Figure JPOXMLDOC01-appb-C000004
    Figure JPOXMLDOC01-appb-C000005
    Figure JPOXMLDOC01-appb-C000006
    　Ｘ１及びＸ１ｂは、各々独立してハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６ハロアルケニル、Ｃ２～Ｃ６ハロアルキニル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
    　ｇ１、ｇ２又はｇ４が２以上の整数を表すとき、各々のＸ１は互いに同一であっても又は互いに相異なってもよく、更に２つのＸ１が隣接する場合には、隣接する２つのＸ１は、－ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＯＣＨ２－，－ＯＣＨ２Ｏ－，－ＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＳＣＨ２－，－ＣＨ２ＣＨ２Ｎ（Ｘ１ａ）－，－ＣＨ２Ｎ（Ｘ１ａ）ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＣＨ２ＯＣＨ２－，－ＣＨ２ＯＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＣＨ＝ＣＨ－，－ＯＣＨ＝ＣＨ－，－ＳＣＨ＝ＣＨ－，－Ｎ（Ｘ１ａ）ＣＨ＝ＣＨ－，－ＯＣＨ＝Ｎ－，－ＳＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）ＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）Ｎ＝ＣＨ－，－ＯＣＨ２ＣＨ＝ＣＨ－，－ＣＨ＝ＣＨＣＨ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＸ１が結合する炭素原子と共に５員環又は６員環を形成してもよく、このとき環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよく、或いは、ｆ１、ｆ２、ｆ４、ｆ５、ｆ６、ｆ７、ｆ８又はｆ９が２以上の整数を表すとき、各々のＸ１ｂは互いに同一であっても又は互いに相異なってもよく、さらに、２つのＸ１ｂが同一の炭素上に置換している場合、２つのＸ１ｂは一緒になってオキソ、チオキソ、イミノ、Ｃ１～Ｃ６アルキルイミノ、Ｃ１～Ｃ６アルコキシイミノ又はＣ１～Ｃ６アルキリデンを形成してもよい。
    　Ｘ１ａは、水素原子、シアノ、－ＯＨ、－ＮＨ２、－ＣＨＯ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２８で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２８で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２８で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２８で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
    　Ｘ１ａの隣接位にＸ１が存在する場合には、隣接するＸ１ａとＸ１は、－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－、－ＣＨ＝ＣＨＣＨ＝ＣＨ－、－Ｎ＝ＣＨＣＨ＝ＣＨ－、－ＣＨ＝Ｎ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－Ｎ＝ＣＨ－又は－ＣＨ＝ＣＨ－ＣＨ＝Ｎ－を形成することにより、Ｘ１ａ及びＸ１のそれぞれが結合する原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合する水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよい。
    　Ｚは、ハロゲン原子、シアノ、ニトロ、－ＯＨ、－ＳＨ、－ＮＨ２、-ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６ハロアルケニル、Ｃ２～Ｃ６ハロアルキニル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、－Ｃ（＝ＮＯＲ２９）Ｒ３０、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
    　ｑが２以上の整数を表すとき、各々のＺは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺが隣接する場合には、隣接する２つのＺは－ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＯＣＨ２－，－ＯＣＨ２Ｏ－，－ＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＳＣＨ２－，－ＣＨ２ＣＨ２Ｎ（Ｘ１ａ）－，－ＣＨ２Ｎ（Ｘ１ａ）ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２ＣＨ２－，－ＣＨ２ＣＨ２ＣＨ２Ｏ－，－ＣＨ２ＣＨ２ＯＣＨ２－，－ＣＨ２ＯＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｏ－，－ＯＣＨ２ＣＨ２Ｓ－，－ＣＨ２ＣＨ＝ＣＨ－，－ＯＣＨ＝ＣＨ－，－ＳＣＨ＝ＣＨ－，－Ｎ（Ｘ１ａ）ＣＨ＝ＣＨ－，－ＯＣＨ＝Ｎ－，－ＳＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）ＣＨ＝Ｎ－，－Ｎ（Ｘ１ａ）Ｎ＝ＣＨ－，－ＯＣＨ２ＣＨ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺが結合する炭素原子と共に５員環又は６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基又はＣ１～Ｃ６アルキルスルホニル基によって任意に置換されてもよい。
    　Ｒ２８、Ｒ２８ａ、Ｒ３１及びＲ３２は、各々独立してハロゲン原子、－ＯＨ、－ＳＨ、－ＮＨ２、－ＣＨＯ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＮＨ２、－Ｃ（Ｓ）ＮＨ２、－Ｓ（Ｏ）２ＮＨ２、－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ３～Ｃ８シクロアルキルカルボニル、Ｃ１～Ｃ６ハロアルキルカルボニル、Ｃ３～Ｃ８ハロシクロアルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６ハロアルコキシカルボニル、Ｃ１～Ｃ6アルキルアミノスルホニル、ジ（Ｃ１～Ｃ６アルキル）アミノスルホニル、Ｃ１～Ｃ6アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６アルキル）アミノ、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
    　Ｒ２９及びＲ２９ａは、各々独立してＣ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ３１で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ３１で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ３１で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ３１で任意に置換された（Ｃ３～Ｃ８）シクロアルキル又はＲ３１で任意に置換された（Ｃ３～Ｃ８）シクロアルケニルを表す。
    　Ｒ３０及びＲ３０ａは、各々独立してＣ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ３２で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ３２で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ３２で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ３２で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ３２で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、フェニル、Ｃ１～Ｃ６アルキルで任意に置換されたフェニル又はハロゲン原子で任意に置換されたフェニルを表す。
    　Ｒ４０、Ｒ４０ａ及びＲ４０ｂは、各々独立してＣ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
    　Ｒ４１は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ４２は、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６ハロアルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、Ｃ１～Ｃ６ハロアルキルスルホニル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
    　ｇ１、ｆ１及びｎは、各々独立して０、１、２又は３の整数を表し、
    　ｇ２及びｆ２は、各々独立して０、１又は２の整数を表し、
    　ｇ３は、０又は１の整数を表し、
    　ｇ４及びｆ４は、各々独立して０、１、２、３又は４の整数を表し、
    　ｆ５は、０、１、２、３、４又は５の整数を表し、
    　ｆ６は、０、１、２、３、４、５又は６の整数を表し、
    　ｆ７は、０、１、２、３、４、５、６又は７の整数を表し、
    　ｆ８は、０、１、２、３、４、５、６、７又は８の整数を表し、
    　ｆ９は、０、１、２、３、４、５、６、７、８又は９の整数を表し、
    　ｑは、１、２、３、４又は５の整数を表し、
    　ｍ１、ｍ２及びｍ３は、各々独立して０又は１の整数を表し、
    　ｒ、ｒ２及びｒ３は、各々独立して０、１又は２の整数を表す。］     A pyrazole or thiazole derivative represented by the formula (1) or a salt thereof.
    Figure JPOXMLDOC01-appb-C000001
     Wherein, A 1 is, -N (-O) m2 or represents -CR 1,
    R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 3 -C 8 cycloalkyl , optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 28a (C 2 ~ C 6 ) alkenyl, C 3 ~ C 8 cycloalkenyl , optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 28a (C 2 ~ C 6 ) alkynyl, C 1 ~ C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 Alkylthio, C 1 ~ C 6 alkylsulfinyl, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkyl Aminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, -C (= NOR 29a) R 30a, Fe Represents Le, the (Z) phenyl substituted by q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q.
    R 2 represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S ( O) 2 NH 2, C 1 ~ C 6 alkyl, substituted optionally substituted with R 28a (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, optionally with R 28a (C 3 ~ C 8) cycloalkyl, C 2 ~ C 6 alkenyl, which is optionally substituted with R 28a (C 2 ~ C 6 ) alkenyl, C 3 ~ C 8 cycloalkenyl, which is optionally substituted with R 28a (C 3 ~ C 8 ) cycloalkenyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 28a , C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 Alkylthio, C 1 -C 6 alkylsulfur Finiru, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1- C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C ( = NOR 29a ) R 30a , phenyl, (Z) pheny substituted by q , Naphthyl, naphthyl substituted by q , or any group of D1-1 to D1-99, and when n represents an integer of 2 or more, each R 2 may be the same as each other Or they may be different from each other.
    B represents a ring represented by either B-1 or B-2.
    Figure JPOXMLDOC01-appb-C000002
     (In the formula, “*” represents the bonding position with the substituent “—N (R a ) R b ”, and “**” represents the bonding position with the substituent shown below.)
    Figure JPOXMLDOC01-appb-C000003
     R a is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 5a (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 5a (C 2 ~ C 6) alkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 5a (C 2 ~ C 6 ) alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 5a (C 3 ~ C 8 ) Cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 5a , —OR 6a , —S (O) r 2 R 6a , —C (O) OR 6a , -C (O) SR6a , -C (S) OR6a , -C (S) SR6a , -C (O) R7a , -C (S) R7a , -N ( R8a ) R9a , —C (O) N (R 8a ) R 9a , —C (S) N (R 8a ) R 9a, -S (O) r2 N (R 8a) R 9a, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (OR 41) 2 , Phenyl, phenyl substituted by (Z) q , naphthyl, naphthyl substituted by (Z) q , or any group of D1-1 to D1-99, or R a together with R 3 To form a C 2 -C 5 alkylene chain or a C 2 -C 5 alkenylene chain to form a 5- to 8-membered ring together with the carbon atom to which R a is bonded and the carbon atom to which R 3 is bonded. In this case, the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is a halogen atom, cyano, nitro, C 1 -C 6 alkyl, —OH, —OR 11a , -SH, S (O) r R 11a, which may be optionally substituted by oxo or thioxo group.
    R b represents —C (O) R 7b or —C (S) R 7b , or R b together with R a may form ═C (R b2 ) R b3 ,
    R b2 represents —OR 6a or —S (O) r2 R 6a ;
    R b3 represents —C (= NOH) R 12b , —C (= NOR 11b ) R 12b or —C {= NN (R 13b ) R 14b } R 12b ,
    R 5a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 10a , —OH, —OR 11a , —SH, —S ( O) r2 R 11a , —N (R 13a ) R 14a , —C (O) OH, —C (O) OR 11a , —C (O) SR 11a , —C (S) OR 11a , —C (S ) SR 11a , —C (O) R 12a , —C (S) R 12a , —C (O) N (R 13a ) R 14a , —C (S) N (R 13a ) R 14a , —S (O ) r2 N (R 13a) R 14a, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (OR 41) 2, phenyl, (Z) phenyl substituted by q , naphthyl, (Z) n substituted by q When R 5a is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino , C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene may be formed.
    R 6a , R 8a and R 9a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 10a , C 2 -C 6 alkenyl, R 10a in optionally substituted (C 2 ~ C 6) alkenyl, C 2 ~ C 6 alkynyl, optionally substituted with R 10a (C 2 ~ C 6) alkynyl, C 3 ~ C 8 cycloalkyl, with R 10a Optionally substituted (C 3 -C 8 ) cycloalkyl, C 3 -C 8 cycloalkenyl, (C 3 -C 8 ) cycloalkenyl optionally substituted with R 10a , —S (O) r2 R 11a , -C (O) OR 11a , -C (O) SR 11a , -C (S) OR 11a , -C (S) SR 11a , -C (O) R 12a , -C (S) R 12a , -N (R 13a ) R 14a , —C (O) N (R 13a ) R 14a , —C (S) N (R 13a ) R 14a , —S (O) r 2 N (R 13a ) R 14a , phenyl, phenyl substituted by (Z) q , naphthyl, ( Z) represents naphthyl substituted by q or any group of D1-1 to D1-99, or R 8a together with R 9a represents a C 2 -C 7 alkylene chain or C 2 -C 7 to form a 3- to 8-membered ring together with the nitrogen atom to which R 8a and R 9a are bonded, and this alkylene chain or alkenylene chain is an oxygen atom, sulfur atom or nitrogen atom. And may be optionally substituted with a (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 10a .
    R 7a is R 6a , -C (= NR 13a ) R 12a , -C (= NOH) R 12a , -C (= NOR 11a ) R 12a or -C {= NN (R 13a ) R 14a } R 12a Represents
    R 7b represents -C (= NOH) R 12b , -C (= NOR 11b ) R 12b or -C {= NN (R 13b ) R 14b } R 12b
    R 10a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 11a , —SH, —S (O) r 2 R 11a , —P ( Represents O) (OR 41 ) 2 , —P (S) (OR 41 ) 2 or —Si (R 40a ) (R 40b ) R 40 , or two R 10a are substituted on the same carbon If present, the two R 5a may be taken together to form an oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
    R 11a and R 12a are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkenyl, optionally with R 15a substituted (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15a (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15a Substituted (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15a , —S (O) r 2 R 16a , —C ( O) OR 16a , -C (O) SR 16a , -C (S) OR 16a , -C (S) SR 16a , -C (O) R 17a , -C (S) R 17a , -N (R 18a ) R 19a, -C (O) N ( 18a) R 19a, -C (S ) N (R 18a) R 19a, -S (O) r2 N (R 18a) R 19a, -Si (R 40a) (R 40b) R 40, phenyl, (Z) Phenyl substituted by q , naphthyl, (Z) naphthyl substituted by q , or any group of D1-1 to D1-99.
    R 11b is substituted C 1 ~ C 10 alkyl, optionally with R 15b (C 1 ~ C 6 ) alkyl, optionally substituted with C 2 ~ C 6 alkenyl, R 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, optionally substituted with C 2 ~ C 6 alkynyl, R 15b (C 2 ~ C 6) Alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r 3 R 16b , —C (O) OR 16b , —C (O) SR 16b , -C (S) OR 16b , -C (S) SR 16b , -C (O) R 17b , -C (S) R 17b , -C (O) N (R 18b ) R 19b , -C (S) N (R 18b) R 19b, - (O) represents the r3 N (R 18b) R 19b , phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q .
    R 12b is a hydrogen atom, a halogen atom, substituted cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , -C (O) SR 16c , -C (S) OR 16c , -C (S) SR 16c , -C (O) R 17c , -C (S) R 17c , -N (R 18c) R 19c, -C ( ) N (R 18c) R 19c , -C (S) N (R 18c) R 19c, -S (O) r N (R 18c) R 19c, -C (= NOH) R 17c, -C (= NOR 16c) R 17c, -C {= NN (R 18c) R 19c} R 17c, phenyl, (Z) phenyl substituted by q, naphthyl, (Z) naphthyl or substituted by q D1-1 ~ D1- Any one of 99 groups is represented.
    R 13a and R 14a each independently represent a hydrogen atom or C 1 -C 6 alkyl, or R 13a together with R 14a is a C 2 -C 7 alkylene chain or C 2 -C 7. To form a 3- to 8-membered ring together with the nitrogen atom to which R 13a and R 14a are bonded. In this case, the alkylene chain or alkenylene chain has an oxygen atom, a sulfur atom or a nitrogen atom. One may be included, and optionally substituted by a (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 15a .
    R 13b is a hydrogen atom, cyano, substituted nitro, C 1 ~ C 6 alkyl, optionally substituted with R 15b (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally with R 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15b (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —OR 16b , —S (O) r3 R 16b , —C (O) OR 16b , -C (O) SR 16b , -C (S) OR 16b , -C (S) SR 16b , -C (O) R 17b , -C (S) R 17b , -C (O ) N (R 18b) R 19b , C (S) N (R 18b ) R 19b, -S (O) r3 N (R 18b) R 19b, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (oR 41) 2, or represents phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any group of naphthyl or D1-1 ~ D1-99 replaced by q Alternatively, R 13b together with R 14b forms a C 2 to C 7 alkylene chain or a C 2 to C 7 alkenylene chain to form a 3 to 8 together with the nitrogen atom to which R 13b and R 14b are attached. In this case, the alkylene chain or alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with R 42 or R 15b (C 1 ~ C 6 Alkyl may be optionally substituted by oxo or thioxo group.
    R 14b is a hydrogen atom, cyano, substituted nitro, C 1 ~ C 6 alkyl, optionally substituted with R 15d (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally with R 15d (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15d (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15d (C 2 -C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15d , —OR 16d , —S (O) r3 R 16d , —C (O) OR 16d , -C (O) SR 16d , -C (S) OR 16d , -C (S) SR 16d , -C (O) R 17d , -C (S) R 17d , -C (O ) N (R 18d) R 19d , C (S) N (R 18d ) R 19d, -S (O) r3 N (R 18d) R 19d, -Si (R 40a) (R 40b) R 40, -P (O) (OR 41) 2, -P (S) (oR 41) 2, or represents phenyl, (Z) phenyl substituted by q, naphthyl, (Z) any group of naphthyl or D1-1 ~ D1-99 replaced by q Alternatively, R 14b may be combined with R 13b to form ═C (R 14e ) R 14f .
    R 14e and R 14f are each independently a hydrogen atom, cyano, nitro, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, R optionally substituted with 15b (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, R optionally substituted with 15b (C 2 ~ C 6) alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 15b (C 3 ~ C 8 ) cycloalkyl, -OR 16b, -S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (S) OR 16b, -C (S) SR 16b, -C (O) R 17b, -C (S) R 17b, -C (O) N R 18b) R 19b, -C ( S) N (R 18b) R 19b, -S (O) r3 N (R 18b) R 19b, -Si (R 40a) (R 40b) R 40, -P (O ) (oR 41) 2, -P (S) (oR 41) 2, phenyl, (Z) phenyl substituted by q, naphthyl, naphthyl or D1-1 ~ D1-99 substituted by (Z) q R 14e and R 14f are bonded by representing any group or R 14e together with R 14f to form a C 2 to C 7 alkylene chain or a C 2 to C 7 alkenylene chain. A 3- to 8-membered ring may be formed together with the carbon atom, and this alkylene chain or alkenylene chain may contain 1, 2 or 3 oxygen atoms, sulfur atoms or nitrogen atoms, and R 42 , R 15b At Substituted in (C 1 ~ C 6) alkyl, it may be optionally substituted by oxo or thioxo group.
    R 15a is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16a , —SH, —S (O) r 2 R 16a , —S ( ═NR 18a ) R 16a , —S (O) (═NR 18a ) R 16a , —P (O) (OR 41 ) 2 , —P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15a is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene Shape It may be.
    R 15b is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16b , —SH, —S (O) r 3 R 16b , —S ( = NR 18b ) R 16b , -S (O) (= NR 18b ) R 16b , -C (O) OH, -C (O) OR 16b , -C (O) R 17b , -C (O) N ( R 18b ) R 19b , -C (= NOR 16b ) R 17b , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, phenyl substituted by (Z) q , Naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R 15b are the same When substituted on carbon, two R 5a together may form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
    R 15c is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, —OH, —OR 16c , —SH, —S (O) r R 16c , —S ( = NR 18c ) R 16c , -S (O) (= NR 18c ) R 16c , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15c is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene Shape It may be.
    R 15d is a halogen atom, cyano, nitro, C 3 to C 8 cycloalkyl, C 3 to C 8 halocycloalkyl, —OH, —OR 16d , —SH, —S (O) r 3 R 16d , —S ( = NR 18d ) R 16d , -S (O) (= NR 18d ) R 16d , -P (O) (OR 41 ) 2 , -P (S) (OR 41 ) 2 , phenyl, (Z) q A substituted phenyl, naphthyl, naphthyl substituted by (Z) q , any group of D1-1 to D1-99 or —Si (R 40a ) (R 40b ) R 40 , or two R When 15d is substituted on the same carbon, the two R 5a together are oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene The It may form,
    R 16a , R 16b , R 16c and R 16d are each independently cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -S (O) r R 21 represents -C (O) R 22, phenyl, phenyl substituted by (Z) q, naphthyl, (Z) any of the groups naphthyl or D1-1 ~ D1-99 substituted by q.
    R 17a , R 17b , R 17c and R 17d are each independently a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 ~ C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 ( C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -C (O) R 22, -C (= NOR 21) R 22, phenyl, (Z) phenyl substituted by q, naphthyl, (Z) naphthyl substituted by q, or any group of D1-1 ~ D1-99 To express.
    R 18a and R 19a each independently represents a hydrogen atom, cyano or C 1 -C 6 alkyl;
    R 18b , R 19b , R 18d and R 19d are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl , C 3 ~ C 8 cycloalkenyl, optionally substituted optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally with R 20 and (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, phenyl, (Z ) Phenyl substituted by q , naphthyl, (Z) naphthyl substituted by q or any group of D1-1 to D1-99, or R 18b together with R 19b represents C 2 By forming a C 7 alkylene chain or a C 2 -C 7 alkenylene chain, a 3- to 8-membered ring may be formed together with the nitrogen atom to which R 18b and R 19b are bonded. The alkenylene chain may contain one or two oxygen atoms, sulfur atoms or nitrogen atoms, and is optionally substituted with (C 1 -C 6 ) alkyl, oxo group or thioxo group optionally substituted with R 42 , R 20 May be.
    R 18c and R 19c are each independently a hydrogen atom, cyano, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , —OR 21 , —S (O) r R 21 , —C (O) OR 21 , —C (O) R 22 , —C (S) R 22 , phenyl or phenyl substituted by (Z) q ;
    R 20 is a halogen atom, cyano, nitro, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, —C (O) OR 21 , phenyl or phenyl substituted by (Z) q , or when two R 20 are substituted on the same carbon, R 5a together may form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene;
    R 21 and R 22 each independently represent a hydrogen atom, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, phenyl or phenyl substituted by (Z) q .
    D1-1 to D1-99 each represent a ring represented by the following structure.
    Figure JPOXMLDOC01-appb-C000004
    Figure JPOXMLDOC01-appb-C000005
    Figure JPOXMLDOC01-appb-C000006
    X 1 and X 1b are each independently a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S ) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl C 3 -C 8 cycloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 ~ C 6 alkylthio, C 1 ~ C 6 haloalkylthio, C 1 ~ C 6 alkylsulfinyl, C 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl, C 1 ~ C 6 haloalkylcarbonyl, C 3 ~ C 8 halocycloalkyl carbonyl, C 1 ~ C 6 alkoxycarbonyl, C 1 ~ C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with a halogen atom.
    When g1, g2, or g4 represents an integer of 2 or more, each X 1 may be the same as or different from each other, and when two X 1 are adjacent, two adjacent X 1 represents —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —CH 2 CH 2 N (X 1a ) —, —CH 2 N (X 1a ) CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 -, -CH 2 OCH 2 O-, -OCH 2 CH 2 O-, -OCH 2 CH 2 S-, -CH 2 CH = CH-, -OCH = CH-, -SCH = CH-, -N (X 1a ) CH═CH—, —OCH═N—, —SCH═N—, —N (X 1 a ) CH = N-, -N (X 1a ) N = CH-, -OCH 2 CH = CH-, -CH = CHCH = CH-, -N = CHCH = CH-, -CH = NCH = CH-, Forming —N═NCH═CH—, —CH═NN═CH—, —N═CHCH═N—, or —N═CHN═CH—, together with the carbon atom to which each X 1 is attached is a 5-membered ring Or a hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group , C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group or C 1 -C 6 alkylsulfonyl group, or f1, f2, f4 , F5, f6, f7, f Or when f9 represents an integer of 2 or more, each X 1b or different are or phase from each other be identical to each other, further, when two which X 1b are substituted on the same carbon, the two X 1b may be taken together to form oxo, thioxo, imino, C 1 -C 6 alkylimino, C 1 -C 6 alkoxyimino or C 1 -C 6 alkylidene.
    X 1a is a hydrogen atom, cyano, —OH, —NH 2 , —CHO, —C (O) NH 2 , —C (S) NH 2 , —S (O) 2 NH 2 , C 1 -C 6 alkyl. , C 2 ~ C 6 alkenyl, C 2 ~ C 6 alkynyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 28 (C 1 ~ C 6 ) alkyl, optionally substituted with R 28 (C 2 ~ C 6) alkenyl, optionally substituted with R 28 (C 2 ~ C 6 ) alkynyl, optionally substituted with R 28 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 28 (C 3 -C 8 ) cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 ~ C 6 haloalkylthio, 1 ~ C 6 haloalkylsulfinyl, C 1 ~ C 6 haloalkylsulfonyl, C 1 ~ C 6 alkylcarbonyl, C 3 ~ C 8 cycloalkylcarbonyl, C 1 ~ C 6 haloalkylcarbonyl, C 3 ~ C 8 halocycloalkyl carbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, optionally substituted with C 1 -C 6 alkyl Represents a substituted phenyl or a phenyl optionally substituted with a halogen atom.
    When X 1 is present at the adjacent position of X 1a , adjacent X 1a and X 1 are —CH 2 CH 2 CH 2 CH 2 —, —CH═CHCH═CH—, —N═CHCH═CH— , —CH═N—CH═CH—, —CH═CH—N═CH—, or —CH═CH—CH═N— to form a six-membered atom together with the atoms to which each of X 1a and X 1 is attached. A hydrogen atom bonded to each carbon atom forming the ring may be a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 It may be optionally substituted with a 1 to C 6 alkoxy group, a C 1 to C 6 alkylthio group, a C 1 to C 6 alkylsulfinyl group or a C 1 to C 6 alkylsulfonyl group.
    Z represents a halogen atom, cyano, nitro, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2 , —S (O ) 2 NH 2 , C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl optionally substituted with R 28 , C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl, C 1 -C 6 alkyl Aminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino, —C (═NOR 29 ) R 30 , phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with a halogen atom.
    When q represents an integer of 2 or more, each Z may be the same as or different from each other. Furthermore, when two Zs are adjacent to each other, the two adjacent Zs are —CH 2 CH 2 CH 2 —, —CH 2 CH 2 O—, —CH 2 OCH 2 —, —OCH 2 O—, —CH 2 CH 2 S—, —CH 2 SCH 2 —, —CH 2 CH 2 N (X 1a ) —, —CH 2 N (X 1a ) CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 O—, —CH 2 CH 2 OCH 2 —, —CH 2 OCH 2 O—, —OCH 2 CH 2 O—, —OCH 2 CH 2 S—, —CH 2 CH═CH—, —OCH═CH—, —SCH═CH—, —N (X 1a ) CH═CH—, -OCH = N -, - SCH = N -, - N (X 1a) CH = N -, - N ( 1a) N = CH -, - OCH 2 CH = CH -, - N = CHCH = CH -, - CH = NCH = CH -, - N = NCH = CH -, - CH = NN = CH -, - N = By forming CHCH═N— or —N═CHN═CH—, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each Z is bonded. The hydrogen atom bonded to the carbon atom is a halogen atom, cyano, nitro, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 alkylthio group, C 1 it may be optionally substituted by ~ C 6 alkylsulfinyl group or a C 1 ~ C 6 alkylsulfonyl group.
    R 28 , R 28a , R 31 and R 32 are each independently a halogen atom, —OH, —SH, —NH 2 , —CHO, —C (O) OH, —C (O) NH 2 , —C (S) NH 2, -S ( O) 2 NH 2, -Si (R 40a) (R 40b) R 40, C 1 ~ C 6 alkoxy, C 1 ~ C 6 haloalkoxy, C 1 ~ C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 3 -C 8 cycloalkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 8 halocycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 Haloalkoxycarbonyl, C 1 -C 6 alkylaminosulfonyl, di (C 1 -C 6 alkyl) aminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di (C 1 -C 6 alkyl) aminocarbonyl, C 1 -C Represents 6 alkylamino, di (C 1 -C 6 alkyl) amino, phenyl, phenyl optionally substituted with C 1 -C 6 alkyl or phenyl optionally substituted with halogen atoms.
    R 29 and R 29a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 31 (C 1 -C 6 ) alkyl optionally substituted with R 31 , (C 2 -C 6 ) alkenyl optionally substituted with R 31 , (C 2 -C 6 ) alkynyl optionally substituted with R 31 , R optionally substituted with 31 representing the (C 3 ~ C 8) optionally substituted cycloalkyl, or R 31 (C 3 ~ C 8 ) cycloalkenyl.
    R 30 and R 30a are each independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 32 (C 1 -C 6 ) alkyl optionally substituted with R 32 , (C 2 -C 6 ) alkenyl optionally substituted with R 32 , (C 2 -C 6 ) alkynyl optionally substituted with R 32 , R optionally substituted with 32 (C 3 ~ C 8) cycloalkyl, optionally substituted with R 32 (C 3 ~ C 8 ) cycloalkenyl, phenyl, phenyl optionally substituted with C 1 ~ C 6 alkyl Alternatively, it represents phenyl optionally substituted with a halogen atom.
    R 40, R 40a and R 40b are each independently C 1 to ~ C 6 alkyl, C 1 ~ C 6 alkoxy or phenyl,
    R 41 represents C 1 -C 6 alkyl,
    R 42 represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C Represents 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, phenyl or phenyl substituted by (Z) q .
    g1, f1 and n each independently represent an integer of 0, 1, 2 or 3;
    g2 and f2 each independently represent an integer of 0, 1 or 2;
    g3 represents an integer of 0 or 1,
    g4 and f4 each independently represent an integer of 0, 1, 2, 3 or 4;
    f5 represents an integer of 0, 1, 2, 3, 4 or 5,
    f6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
    f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
    f8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
    f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
    q represents an integer of 1, 2, 3, 4 or 5;
    m1, m2 and m3 each independently represent an integer of 0 or 1,
    r, r2 and r3 each independently represents an integer of 0, 1 or 2. ]
  2. 　Ａ１は、－ＣＲ１を表し、
    　Ｒ１、Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル又はＣ１～Ｃ６アルキルカルボニルを表し、
    　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｂは、Ｂ－１を表す請求項１に記載のピラゾール誘導体又はその塩。     A 1 represents -CR 1
    R 1 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 28a , C 2 -C 6 alkynyl , (C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl optionally substituted with R 28a ,
    R 2 represents a halogen atom or C 1 -C 6 alkyl,
    The pyrazole derivative or a salt thereof according to claim 1, wherein B represents B-1.
  3. 　Ａ１は、－Ｎ（－Ｏ）ｍ２を表し、
    　Ｂは、Ｂ－１を表し、
    　Ｒ３及びＲ４は、各々独立して水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表す請求項１に記載のピラゾール誘導体又はその塩。     A 1 represents -N (-O) m2 ,
    B represents B-1,
    R 3 and R 4 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl;
    The pyrazole derivative or a salt thereof according to claim 1 , wherein R 2 represents a halogen atom or C 1 -C 6 alkyl.
  4. 　Ｂは、Ｂ－２を表し、
    　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）ＳＲ１６ｃ、－Ｃ（Ｓ）ＯＲ１６ｃ、－Ｃ（Ｓ）ＳＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｓ）Ｒ１７ｃ、－Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ又は－Ｃ（Ｓ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃを表す請求項１に記載のチアゾール誘導体又はその塩。     B represents B-2,
    R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, substituted C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 —C 6 ) alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15c , —OR 16c , —S (O) r R 16c , —C (O) OR 16c , —C (O) SR 16c , —C (S) OR 16c , —C (S) SR 16c , —C (O) R 17c , —C (S) R 17c , —N (R 18c ) R 19c , —C (O) N (R 18 The thiazole derivative or a salt thereof according to claim 1, which represents c ) R 19c or -C (S) N (R 18c ) R 19c .
  5. 　Ｒ１は、水素原子又はハロゲン原子を表し、
    　Ｒ２は、ハロゲン原子を表し、
    　Ｒ３は、水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｒ２８ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、Ｒ２８ａで任意に置換された（Ｃ２～Ｃ６）アルキニル又はＣ１～Ｃ６アルキルカルボニルを表し、
    　Ｒ４は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ６ａ、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ又は－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａを表す。
    　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表すか、或いは、ＲｂはＲａと一緒になって＝Ｃ（Ｒｂ２）Ｒｂ３を形成してもよく、
    　Ｒｂ２は、－ＯＲ６ａを表し、
    　Ｒｂ３は、－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表し、
    　Ｒ５ａは、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ、－Ｓ（Ｏ）ｒ２Ｒ１１ａ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１１ａ、－Ｃ（Ｏ）Ｎ（Ｒ１３ａ）Ｒ１４ａ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３又はＤ１－３４を表し、
    　Ｒ６ａは、Ｃ１～Ｃ６アルキル又はＲ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ７ａは、Ｃ１～Ｃ６アルキル、Ｒ１０ａで任意に置換された（Ｃ１～Ｃ６）アルキル又は－Ｃ（＝ＮＯＲ１１ａ）Ｒ１２ａを表し、
    　Ｒ７ｂは、－Ｃ（＝ＮＯＨ）Ｒ１２ｂ又は－Ｃ（＝ＮＯＲ１１ｂ）Ｒ１２ｂを表し、
    　Ｒ８ａは、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ９ａは、水素原子又はＣ１～Ｃ６アルキルを表す。
    　Ｒ１０ａは、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
    　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ１６ａ、－Ｃ（Ｏ）Ｒ１７ａ、－Ｃ（Ｏ）Ｎ（Ｒ１８ａ）Ｒ１９ａ又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
    　Ｒ１１ｂは、Ｃ１～Ｃ７アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ１６ｂ又は－Ｃ（Ｏ）Ｒ１７ｂを表し、
    　Ｒ１２ａは、Ｒ１５ａで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒＲ１６ｃ、－Ｃ（Ｏ）ＯＲ１６ｃ、－Ｃ（Ｏ）Ｒ１７ｃ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｃ）Ｒ１９ｃ、－Ｃ（＝ＮＯＲ１６ｃ）Ｒ１７ｃ、－Ｃ｛＝ＮＮ（Ｒ１８ｃ）Ｒ１９ｃ｝Ｒ１７ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－２、Ｄ１－３２又はＤ１－３４を表す。
    　Ｒ１３ａ及びＲ１４ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ１５ａは、－ＯＲ１６ａ、－Ｓ（Ｏ）ｒ２Ｒ１６ａ、フェニル又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
    　Ｒ１５ｂは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＨ、－ＯＲ１６ｂ、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＨ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（＝ＮＯＲ１６ｂ）Ｒ１７ｂ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３３又はＤ１－８４を表し、
    　Ｒ１５ｃは、ハロゲン原子、シアノ、－ＯＨ、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
    　Ｒ１６ａは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル又は－Ｎ（Ｒ２３）Ｒ２４を表す。
    　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｓ（Ｏ）ｒＲ２１、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
    　Ｒ１７ａは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
    　Ｒ１７ｂは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１７ｃは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１８ａ及びＲ１９ａは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ１８ｂは、水素原子を表すか、或いは、Ｒ１８ｂはＲ１９ｂと一緒になってＣ５のアルキレン鎖を形成することにより、Ｒ１８ｂ及びＲ１９ｂが結合する窒素原子と共に６員環を形成してもよく、このときこのアルキレン鎖は酸素原子を１個含んでもよく、
    　Ｒ１８ｃは、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ２２を表し、
    　Ｒ１９ｂは、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１９ｃは、水素原子を表す。
    　Ｒ２０は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
    　Ｒ２１は、（Ｚ）ｑによって置換されたフェニルを表し、
    　Ｒ２２は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ２３及びＲ２４は、水素原子を表し、
    　Ｘ１は、ハロゲン原子又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ２８は、ハロゲン原子を表し、
    　Ｒ２８ａは、ハロゲン原子又は－Ｓｉ（Ｒ４０ａ）（Ｒ４０ｂ）Ｒ４０を表し、
    　Ｚは、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
    　Ｒ４０、Ｒ４０ａ及びＲ４０ｂは、各々独立してＣ１～Ｃ６アルキルを表す。
    　ｇ１、ｇ４、ｍ１及びｎは、各々独立して０又は1の整数を表し、
    　ｆ５、ｆ７及びｍ３は、０を表し、
    　ｑは、１の整数を表し、
    　ｒ及びｒ３は、各々独立して０、１又は２の整数を表し、
    　ｒ２は、０又は２の整数を表す請求項２に記載のピラゾール誘導体又はその塩。     R 1 represents a hydrogen atom or a halogen atom,
    R 2 represents a halogen atom,
    R 3 represents a hydrogen atom, a halogen atom, substituted C 1 ~ C 6 alkyl, optionally substituted with R 28a (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkynyl, optionally with R 28a ( C 2 -C 6 ) alkynyl or C 1 -C 6 alkylcarbonyl,
    R 4 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
    R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) represents an r2 R 6a, -C (O) oR 6a, -C (O) R 7a, -C (O) N (R 8a) R 9a or -C (S) N (R 8a ) R 9a.
    R b represents —C (O) R 7b or —C (S) R 7b , or R b together with R a may form ═C (R b2 ) R b3 ,
    R b2 represents —OR 6a ;
    R b3 represents -C (= NOR 11b ) R 12b ,
    R 5a is cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a , —S (O) r 2 R 11a , —C (O) OH, —C (O) OR 11a , —C (O) N (R 13a ) R 14a , phenyl, phenyl substituted by (Z) q , D1-32, D1-33 or D1-34;
    R 6a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 10a ,
    R 7a represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 10a or —C (═NOR 11a ) R 12a ,
    R 7b represents -C (= NOH) R 12b or -C (= NOR 11b ) R 12b ;
    R 8a represents a hydrogen atom or C 1 -C 6 alkyl;
    R 9a represents a hydrogen atom or C 1 -C 6 alkyl.
    R 10a represents —OR 11a or —S (O) r2 R 11a ;
    R 11a is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15a , C 2 -C 6 alkynyl, -C (O) OR 16a , -C (O) R 17a , —C (O) N (R 18a ) R 19a or —Si (R 40a ) (R 40b ) R 40 ,
    R 11b is C 1 -C 7 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted with R 15b , -C (O) OR 16b or Represents -C (O) R 17b ,
    R 12a represents (C 1 -C 6 ) alkyl optionally substituted with R 15a ,
    R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, optionally substituted with C 2 ~ C 6 alkenyl, R 15c (C 2 ~ C 6) alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkynyl, optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkyl, -S (O) r R 16c , -C (O) OR 16c , -C (O) R 17c , -C (O) N (R 18c ) R 19c , -C (= NOR 16c ) R 17c , -C {= NN (R 18c ) R 19c } R 17c , phenyl, phenyl substituted by (Z) q , D1-2, D1-32 or D1-34.
    R 13a and R 14a each independently represents a hydrogen atom or C 1 -C 6 alkyl;
    R 15a represents —OR 16a , —S (O) r2 R 16a , phenyl or —Si (R 40a ) (R 40b ) R 40 ,
    R 15b is a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 16b , —S (O) r3 R 16b , —C (O) OH, —C (O) OR 16b , —C (O) represents N (R 18b ) R 19b , —C (═NOR 16b ) R 17b , (Z) q , phenyl substituted by q , D1-33 or D1-84,
    R 15c represents a halogen atom, cyano, —OH, —OR 16c , —S (O) r R 16c , phenyl, phenyl substituted by (Z) q , D1-7, D1-87 or D1-98. ,
    R 16a represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
    R 16b represents C 1 -C 6 alkyl or —N (R 23 ) R 24 .
    R 16c is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , -S (O) r R 21 , (Z) represents phenyl or D1-32 substituted by q ;
    R 17a represents C 1 -C 6 alkyl or phenyl;
    R 17b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
    R 17c represents C 1 -C 6 alkyl;
    R 18a and R 19a each independently represent C 1 -C 6 alkyl;
    R 18b represents a hydrogen atom, or R 18b together with R 19b forms a C 5 alkylene chain to form a 6-membered ring with the nitrogen atom to which R 18b and R 19b are bonded. In this case, the alkylene chain may contain one oxygen atom,
    R 18c represents C 1 -C 6 alkyl or —C (O) R 22 ,
    R 19b represents (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
    R 19c represents a hydrogen atom.
    R 20 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
    R 21 represents phenyl substituted by (Z) q ;
    R 22 represents C 1 -C 6 alkyl;
    R 23 and R 24 represent a hydrogen atom,
    X 1 represents a halogen atom or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
    R 28 represents a halogen atom,
    R 28a represents a halogen atom or —Si (R 40a ) (R 40b ) R 40 ;
    Z represents a halogen atom, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
    R 40 , R 40a and R 40b each independently represent C 1 -C 6 alkyl.
    g1, g4, m1 and n each independently represent an integer of 0 or 1,
    f5, f7 and m3 represent 0;
    q represents an integer of 1;
    r and r3 each independently represents an integer of 0, 1 or 2;
    The pyrazole derivative or a salt thereof according to claim 2, wherein r2 represents 0 or an integer of 2.
  6. 　Ａ１は、－ＣＲ１を表し、
    　Ｒ１及びＲ３は、各々独立して水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ２は、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ１２ｂは、水素原子、シアノ、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃ任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ３～Ｃ８シクロアルキル又はＲ１５ｃで任意に置換された（Ｃ３～Ｃ８）シクロアルキルを表す請求項４に記載のチアゾール誘導体又はその塩。     A 1 represents -CR 1
    R 1 and R 3 each independently represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl;
    R 2 represents a halogen atom or C 1 -C 6 alkyl,
    R 12b is a hydrogen atom, cyano, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, substituted C 2 ~ C 6 alkenyl, the R 15c optionally (C 2 ~ C 6) alkenyl, C 3 ~ C 8 cycloalkenyl, substituted is optionally substituted with R 15c (C 3 ~ C 8 ) cycloalkenyl, C 2 ~ C 6 alkynyl, optionally with R 15c (C 2 The thiazole derivative or salt thereof according to claim 4, which represents (C 3 -C 8 ) cycloalkyl optionally substituted with -C 6 ) alkynyl, C 3 -C 8 cycloalkyl or R 15c .
  7. 　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ６ａ、－Ｃ（Ｏ）Ｒ７ａ、－Ｃ（Ｏ）Ｎ（Ｒ８ａ）Ｒ９ａ又は－Ｃ（Ｓ）Ｎ（Ｒ８ａ）Ｒ９ａを表すか、或いは、ＲａはＲ３と一緒になってＣ２～Ｃ４のアルキレン鎖を形成することにより、Ｒａが結合する窒素原子及びＲ３が結合する炭素原子と共に５～７員環を形成してもよく、
    　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表し、
    　Ｒ５ａは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
    　Ｒ６ａ及びＲ７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ８ａ及びＲ９ａは、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、－Ｃ（Ｏ）ＯＲ１６ａ又は－Ｃ（Ｏ）Ｒ１７ａを表す。
    　Ｒ１１ｂは、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル又はＣ２～Ｃ６アルキニルを表し、
    　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表し、
    　Ｒ１３ｂ及びＲ１４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、、Ｄ１－３７又はＤ１－３８を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４～Ｃ６のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５～７員環を形成してもよい。
    　Ｒ１５ｂは、ハロゲン原子又はシアノを表し、
    　Ｒ１５ｃは、-ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
    　Ｒ１６ａ及びＲ１７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、、Ｄ１－３７又はＤ１－３８を表し
    　Ｒ１７ｂ及びＲ１８ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
    　Ｒ１９ｂは、水素原子又はＣ１～Ｃ６アルキルを表す。
    　Ｒ２０は、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ又はフェニルを表し、
    　Ｘ１は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ２８は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
    　Ｚは、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６ハロアルコキシ又はＣ１～Ｃ６ハロアルキルチオを表す請求項６に記載のチアゾール誘導体又はその塩。     R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) OR 6a , —C (O) R 7a , —C (O) N (R 8a ) R 9a or —C (S) N (R 8a ) R 9a , or R a together with R 3 And forming a C 2 -C 4 alkylene chain to form a 5- to 7-membered ring together with the nitrogen atom to which R a is bonded and the carbon atom to which R 3 is bonded,
    R b represents —C (O) R 7b or —C (S) R 7b ;
    R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S (O) r2 R 11a ,
    R 6a and R 7a each independently represent C 1 -C 6 alkyl;
    R 8a and R 9a each independently represents a hydrogen atom or C 1 -C 6 alkyl;
    R 11a represents C 1 -C 6 alkyl, —C (O) OR 16a or —C (O) R 17a .
    R 11b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted with R 15b ,
    R 12b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl or (C 2 -C 6 ) alkynyl optionally substituted with R 15c ,
    R 13b and R 14b are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 Cycloalkyl, —S (O) r3 R 16b , —C (O) OR 16b , —C (O) SR 16b , —C (O) R 17b , —C (O) N (R 18b ) R 19b , — C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38 Alternatively, R 13b may form a C 4 -C 6 alkylene chain together with R 14b to form a 5- to 7-membered ring with the nitrogen atom to which R 13b and R 14b are bonded. .
    R 15b represents a halogen atom or cyano,
    R 15c represents —OH, —OR 16c , —SH, —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98;
    R 16a and R 17a each independently represent C 1 -C 6 alkyl;
    R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
    R 16c is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, Phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38 R 17b and R 18b are each independently hydrogen An atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, phenyl or (Z) represents phenyl substituted by q ;
    R 19b represents a hydrogen atom or C 1 -C 6 alkyl.
    R 20 represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio or phenyl,
    X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
    R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
    The thiazole derivative according to claim 6, wherein Z represents a halogen atom, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio. Its salt.
  8. 　Ｒ１は、水素原子を表し、
    　Ｒ３は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し
    　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルキニル又は－Ｃ（Ｏ）ＯＲ６ａを表すか、或いは、ＲａはＲ３と一緒になってＣ３のアルキレン鎖を形成することにより、Ｒａが結合する窒素原子及びＲ３が結合する炭素原子と共に６員環を形成してもよく、
    　Ｒｂは、－Ｃ（Ｏ）Ｒ７ｂを表し、
    　Ｒ５ａは、Ｃ３～Ｃ８シクロアルキル又は－ＯＲ１１ａを表し、
    　Ｒ６ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１１ａは、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ１７ａを表し、
    　Ｒ１１ｂは、Ｃ１～Ｃ６アルキル又はＲ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表し、
    　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
    　Ｒ１４ｂは、水素原子を表し、
    　Ｒ１５ｂは、ハロゲン原子を表す。
    　Ｒ１５ｃは、－ＯＲ１６ｃ、－Ｓ（Ｏ）ｒＲ１６ｃ、（Ｚ）ｑによって置換されたフェニル、Ｄ１－７、Ｄ１－８７又はＤ１－９８を表し、
    　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル又はＲ２０で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
    　Ｒ１７ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１７ｂは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル又はフェニルを表し、
    　Ｒ１８ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表し、
    　Ｒ１９ｂは、水素原子を表す。
    　Ｒ２０は、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
    　Ｘ１は、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ２８は、ハロゲン原子を表し、
    　Ｚは、ハロゲン原子、ニトロ又は、Ｃ１～Ｃ６アルコキシを表し、
    　ｇ１及びｇ４は、１の整数を表し、
    　ｆ５、ｆ７、ｍ１、ｍ３及びｎは、０を表し、
    　ｑは、１又は２の整数を表し、
    　ｒは、０、１又は２の整数を表す請求項７に記載のチアゾール誘導体又はその塩。     R 1 represents a hydrogen atom,
    R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl, R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 to C 6 alkynyl or —C (O) OR 6a , or R a together with R 3 forms a C 3 alkylene chain to form a nitrogen atom to which R a is attached and R 3 May form a 6-membered ring with the carbon atom to which
    R b represents —C (O) R 7b ;
    R 5a represents C 3 -C 8 cycloalkyl or —OR 11a ;
    R 6a represents C 1 -C 6 alkyl;
    R 11a represents C 1 -C 6 alkyl or —C (O) R 17a ,
    R 11b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 15b ,
    R 12b represents hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R optionally substituted with 15c (C 1 ~ C 6) alkyl or R 15c and (C 2 ~ C 6) alkynyl,
    R 13b is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 2 -C 6 alkenyl optionally substituted with R 15b , —C (O) OR 16b , —C (O ) R 17b , —C (O) N (R 18b ) R 19b , —C (S) N (R 18b ) R 19b , phenyl or phenyl substituted by (Z) q ,
    R 14b represents a hydrogen atom,
    R 15b represents a halogen atom.
    R 15c represents —OR 16c , —S (O) r R 16c , (Z) q substituted with phenyl, D1-7, D1-87 or D1-98;
    R 16b represents C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 20 ;
    R 16c is, C 1 ~ C 6 alkyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, C 3 ~ C 8 cycloalkyl, substituted by (Z) q Represents phenyl or D1-32.
    R 17a represents C 1 -C 6 alkyl;
    R 17b represents C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 3 -C 8 cycloalkyl or phenyl;
    R 18b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, phenyl or phenyl substituted by (Z) q ;
    R 19b represents a hydrogen atom.
    R 20 represents a halogen atom, cyano, C 1 -C 6 alkoxy or phenyl,
    X 1 represents (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
    R 28 represents a halogen atom,
    Z represents a halogen atom, nitro or C 1 -C 6 alkoxy;
    g1 and g4 represent an integer of 1;
    f5, f7, m1, m3 and n represent 0;
    q represents an integer of 1 or 2,
    The thiazole derivative or a salt thereof according to claim 7, wherein r represents an integer of 0, 1 or 2.
  9. 　Ｒ７ｂは、－Ｃ｛＝ＮＮ（Ｒ１３ｂ）Ｒ１４ｂ｝Ｒ１２ｂを表す請求項２に記載のピラゾール誘導体又はその塩。 The pyrazole derivative or a salt thereof according to claim 2, wherein R 7b represents -C {= NN (R 13b ) R 14b } R 12b .
  10. 　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｃ（Ｏ）ＯＲ６ａ又は－Ｃ（Ｏ）Ｒ７ａを表し、
    　Ｒｂは、、－Ｃ（Ｏ）Ｒ７ｂ又は－Ｃ（Ｓ）Ｒ７ｂを表し、
    　Ｒ５ａは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、-ＯＨ、－ＯＲ１１ａ又は－Ｓ（Ｏ）ｒ２Ｒ１１ａを表し、
    　Ｒ６ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ７ａは、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
    　Ｒ１１ａは、Ｃ１～Ｃ６アルキル、－Ｃ（Ｏ）ＯＲ１６ａ又は－Ｃ（Ｏ）Ｒ１７ａを表し、
    　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル又はＲ１５ｃで任意に置換された（Ｃ２～Ｃ６）アルキニルを表す。
    　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ１５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｒ１５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｓ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｓ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｓ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４～Ｃ６のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５～７員環を形成してもよい。
    　Ｒ１４ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル又はＣ２～Ｃ６アルケニルを表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよく、
    　Ｒ１４ｅ及びＲ１４ｆは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、－ＯＲ１６ｂ又は－Ｓ（Ｏ）ｒ３Ｒ１６ｂを表し、
    　Ｒ１５ｂは、ハロゲン原子又はシアノを表し、
    　Ｒ１５ｃは、-ＯＨ、－ＯＲ１６ｃ、－ＳＨ、－Ｓ（Ｏ）ｒＲ１６ｃ、Ｄ１－８７又はＤ１－９８を表し、
    　Ｒ１６ａ及びＲ１７ａは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、フェニル又は（Ｚ）ｑによって置換されたフェニル表し、
    　Ｒ１６ｃは、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、Ｄ１－３７又はＤ１－３８を表す。
    　Ｒ１７ｂ、Ｒ１８ｂ及びＲ１９ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２、Ｄ１－３３、Ｄ１－３４、Ｄ１－３６、、Ｄ１－３７又はＤ１－３８を表し、
    　Ｒ２０は、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＲ２１、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
    　Ｘ１は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＲ２８で任意に置換された（Ｃ１～Ｃ６）アルキルを表し、
    　Ｒ２８は、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルキルチオを表し、
    　Ｚは、ハロゲン原子、ニトロ、Ｃ１～Ｃ６アルキル、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６ハロアルコキシ、Ｃ１～Ｃ６アルキルチオ又はＣ１～Ｃ６ハロアルキルチオを表す請求項９に記載のピラゾール誘導体又はその塩。     R a is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —C (O) Represents OR 6a or —C (O) R 7a ,
    R b represents —C (O) R 7b or —C (S) R 7b ;
    R 5a represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OH, —OR 11a or —S (O) r2 R 11a ,
    R 6a represents C 1 -C 6 alkyl;
    R 7a represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl,
    R 11a represents C 1 -C 6 alkyl, —C (O) OR 16a or —C (O) R 17a ,
    R 12b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15c (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15c (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl or (C 2 -C 6 ) alkynyl optionally substituted with R 15c .
    R 13b is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 15b (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 15b (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, (C 3 -C 8 ) cycloalkyl optionally substituted with R 15b , —S (O) r3 R 16b , —C ( O) OR 16b , —C (S) OR 16b , —C (O) SR 16b , —C (S) SR 16b , —C (O) R 17b , —C (S) R 17b , —C (O) N (R 18b ) R 19b , —C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1 represent a -37 or D1-38, or, R 1 b is by forming an alkylene chain of C 4 ~ C 6 taken together with R 14b, may form a 5- to 7-membered ring together with the nitrogen atom to which R 13b and R 14b are bonded.
    R 14b represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl or C 2 -C 6 alkenyl optionally substituted with R 15b , or R 14b together with R 13b = C (R 14e ) R 14f may be formed,
    R 14e and R 14f each independently represent a hydrogen atom, C 1 -C 6 alkyl, —OR 16b or —S (O) r3 R 16b ,
    R 15b represents a halogen atom or cyano,
    R 15c represents -OH, -OR 16c , -SH, -S (O) r R 16c , D1-87 or D1-98,
    R 16a and R 17a each independently represent C 1 -C 6 alkyl;
    R 16b is, C 1 ~ C 6 -alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) Represents phenyl substituted by alkenyl, phenyl or (Z) q ;
    R 16c is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, Phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38.
    R 17b , R 18b and R 19b are each independently a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, optionally substituted with R 20 (C 2 ~ C 6 ) alkenyl, optionally substituted with R 20 (C 2 ~ C 6) alkynyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkyl, optionally substituted with R 20 (C 3 ~ C 8 ) cycloalkenyl, -C (O) R 22, - C (= NOR 21 ) R 22 , phenyl, phenyl substituted by (Z) q , D1-32, D1-33, D1-34, D1-36, D1-37 or D1-38,
    R 20 represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1- C 6 alkylsulfonyl, —C (O) OR 21 , phenyl or phenyl substituted by (Z) q .
    X 1 represents a halogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 28 ,
    R 28 represents a halogen atom, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio,
    Z is a halogen atom, nitro, C 1 ~ C 6 alkyl, optionally substituted (C 1 ~ C 6) with R 28 alkyl, C 3 ~ C 8 cycloalkyl alkyl, C 3 ~ C 8 halocycloalkyl alkyl, C The pyrazole derivative or a salt thereof according to claim 9, which represents 1 to C 6 alkoxy, C 1 to C 6 haloalkoxy, C 1 to C 6 alkylthio or C 1 to C 6 haloalkylthio.
  11. 　Ｒ１は、水素原子を表し、
    　Ｒ２は、ハロゲン原子を表し、
    　Ｒ４は、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ３は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル又は－Ｃ（Ｏ）Ｒ７ａを表し、
    　Ｒ５ａは、－ＯＲ１１ａを表し、
    　Ｒ７ａは、Ｃ３～Ｃ８シクロアルキルを表し、
    　Ｒ１１ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１２ｂは、水素原子、Ｃ１～Ｃ６アルキル又はＲ１５ｃで任意に置換された（Ｃ１～Ｃ６）アルキルを表す。
    　Ｒ１３ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ１５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、－Ｓ（Ｏ）ｒ３Ｒ１６ｂ、－Ｃ（Ｏ）ＯＲ１６ｂ、－Ｃ（Ｏ）ＳＲ１６ｂ、－Ｃ（Ｏ）Ｒ１７ｂ、－Ｃ（Ｏ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、－Ｃ（Ｓ）Ｎ（Ｒ１８ｂ）Ｒ１９ｂ、フェニル、（Ｚ）ｑによって置換されたフェニル、Ｄ１－３２又はＤ１－３７を表すか、或いは、Ｒ１３ｂはＲ１４ｂと一緒になってＣ４のアルキレン鎖を形成することにより、Ｒ１３ｂ及びＲ１４ｂが結合する窒素原子と共に５員環を形成してもよく、
    　Ｒ１４ｂは、水素原子又はＣ１～Ｃ６アルキルを表すか、或いは、Ｒ１４ｂはＲ１３ｂと一緒になって＝Ｃ（Ｒ１４ｅ）Ｒ１４ｆを形成してもよい。
    　Ｒ１４ｅは、Ｃ１～Ｃ６アルキル又は－ＯＲ１６ｂを表し、
    　Ｒ１４ｆは、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ１５ｂは、ハロゲン原子を表し、
    　Ｒ１５ｃは、－Ｓ（Ｏ）ｒＲ１６ｃを表し、
    　Ｒ１６ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル又はフェニルを表し、
    　Ｒ１６ｃは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１７ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｃ（Ｏ）Ｒ２２、－Ｃ（＝ＮＯＲ２１）Ｒ２２、フェニル、（Ｚ）ｑによって置換されたフェニル又はＤ１－３２を表し、
    　Ｒ１８ｂは、Ｃ１～Ｃ６アルキル、Ｃ２～Ｃ６アルケニル、Ｃ３～Ｃ８シクロアルキル、フェニル又は（Ｚ）ｑによって置換されたフェニルを表す。
    　Ｒ１９ｂは、水素原子を表し、
    　Ｒ２０は、シアノ、Ｃ３～Ｃ８シクロアルキル、Ｃ３～Ｃ８シクロアルケニル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、-Ｃ（Ｏ）ＯＲ２１又はフェニルを表し、
    　Ｒ２１は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ２２は、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ２８は、ハロゲン原子を表し、
    　Ｚは、ハロゲン原子、Ｒ２８で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８ハロシクロアルキル、Ｃ１～Ｃ６ハロアルコキシ又はＣ１～Ｃ６ハロアルキルチオを表し、
    　ｇ１、ｇ４及びｍ３は、０を表し、
    　ｎは、０又は１の整数を表し、
    　ｑは、１又は２の整数を表し、
    　ｒは、０、１又は２の整数を表し、
    　ｒ３は、２の整数を表す請求項１０に記載のピラゾール誘導体又はその塩。     R 1 represents a hydrogen atom,
    R 2 represents a halogen atom,
    R 4 represents a hydrogen atom or C 1 -C 6 alkyl,
    R 3 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
    R a represents a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a or —C (O) R 7a ,
    R 5a represents -OR 11a ;
    R 7a represents C 3 -C 8 cycloalkyl,
    R 11a represents C 1 -C 6 alkyl,
    R 12b represents a hydrogen atom, C 1 -C 6 alkyl or (C 1 -C 6 ) alkyl optionally substituted with R 15c .
    R 13b is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 15b , C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, —S (O ) r3 R 16b, -C (O ) OR 16b, -C (O) SR 16b, -C (O) R 17b, -C (O) N (R 18b) R 19b, -C (S) N (R 18b ) R 19b , phenyl, phenyl substituted by (Z) q , D1-32 or D1-37, or R 13b together with R 14b forms a C 4 alkylene chain , R 13b and R 14b may form a 5-membered ring with the nitrogen atom to which they are bonded,
    R 14b represents a hydrogen atom or C 1 -C 6 alkyl, or R 14b together with R 13b may form ═C (R 14e ) R 14f .
    R 14e represents C 1 -C 6 alkyl or —OR 16b ,
    R 14f represents a hydrogen atom or C 1 -C 6 alkyl,
    R 15b represents a halogen atom,
    R 15c represents -S (O) r R 16c ;
    R 16b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, (C 1 -C 6 ) alkyl or phenyl optionally substituted with R 20 ,
    R 16c represents C 1 -C 6 alkyl;
    R 17b is optionally substituted with a hydrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, R 20 (C 1 -C 6 ) alkyl, —C (O) R 22 , —C (═NOR 21 ) R 22 , phenyl, phenyl substituted by (Z) q or D1-32,
    R 18b represents C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by (Z) q .
    R 19b represents a hydrogen atom,
    R 20 represents cyano, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, -C (O) OR 21 or phenyl,
    R 21 represents C 1 -C 6 alkyl;
    R 22 represents a hydrogen atom or C 1 -C 6 alkyl,
    R 28 represents a halogen atom,
    Z represents a halogen atom, (C 1 -C 6 ) alkyl optionally substituted with R 28 , C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxy or C 1 -C 6 haloalkylthio;
    g1, g4 and m3 represent 0;
    n represents an integer of 0 or 1,
    q represents an integer of 1 or 2,
    r represents an integer of 0, 1 or 2;
    The pyrazole derivative or a salt thereof according to claim 10, wherein r3 represents an integer of 2.
  12. 　請求項１～１１のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する有害生物防除剤。 A pest control agent comprising one or more selected from the pyrazole or thiazole derivative according to any one of claims 1 to 11 or a salt thereof as an active ingredient.
  13. 　請求項１～１１のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する農薬。 An agrochemical containing one or more selected from the pyrazole or thiazole derivatives according to any one of claims 1 to 11 or a salt thereof as an active ingredient.
  14. 　請求項１～１１のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する、哺乳動物又は鳥類の内部若しくは外部寄生虫防除剤。 A mammalian or avian internal or ectoparasite control agent comprising, as an active ingredient, one or more selected from the pyrazole or thiazole derivative according to any one of claims 1 to 11 or a salt thereof.
  15. 　請求項１～１１のいずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する殺虫剤又は殺ダニ剤。 An insecticide or acaricide containing, as an active ingredient, one or more selected from the pyrazole or thiazole derivatives or salts thereof according to any one of claims 1 to 11.
  16. 　請求項１～１１いずれかに記載のピラゾール若しくはチアゾール誘導体又はその塩から選ばれる１種又は２種以上を有効成分として含有する土壌処理剤。 A soil treatment agent containing one or more selected from the pyrazole or thiazole derivatives according to any one of claims 1 to 11 or a salt thereof as an active ingredient.
  17. 　土壌処理方法が土壌潅注処理である請求項１６に記載の土壌処理剤。 The soil treatment agent according to claim 16, wherein the soil treatment method is soil irrigation treatment.
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