WO2013065725A1 - フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法 - Google Patents

フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法 Download PDF

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WO2013065725A1
WO2013065725A1 PCT/JP2012/078143 JP2012078143W WO2013065725A1 WO 2013065725 A1 WO2013065725 A1 WO 2013065725A1 JP 2012078143 W JP2012078143 W JP 2012078143W WO 2013065725 A1 WO2013065725 A1 WO 2013065725A1
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group
alkyl
alkoxy
same
cycloalkyl
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PCT/JP2012/078143
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English (en)
French (fr)
Japanese (ja)
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松崎　義広
中尾　勇美
英二 安河内
佳典 御所
遠西　正範
諏訪　明之
佳代 犬飼
元文 中野
藤岡　伸祐
三原　純
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日本農薬株式会社
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Priority to CN201280053503.4A priority Critical patent/CN104024222A/zh
Priority to IN3976CHN2014 priority patent/IN2014CN03976A/en
Publication of WO2013065725A1 publication Critical patent/WO2013065725A1/ja

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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    • 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
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    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
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    • 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
    • A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
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    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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Definitions

  • the present invention relates to an agricultural and horticultural insecticide containing a novel phthalamide derivative containing a fused heterocyclic group or a salt thereof as an active ingredient and a method for using the same.
  • an object of the present invention is to provide a new compound for a novel agricultural and horticultural insecticide.
  • the present inventors have found that the phthalamide derivative or its salt, which has not been known so far, has excellent characteristics that a conventional similar compound does not have, and As a result of research, the present invention has been completed.
  • X 1 is (a1) hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 8 ) alkyl group; (a4) (C 1 -C 8 ) haloalkyl group; (a5) (C 1 -C 8 ) alkoxy group; (a6) (C 1 -C 8 ) haloalkoxy group; (a7) (C 1 -C 8 ) alkylthio group; (a8) (C 1 -C 8 ) haloalkylthio group; (a9) a (C 1 -C 8 ) alkylsulfinyl group; (a10) (C 1 -C 8 ) haloalkylsulfinyl group; (a11) (C 1 -C 8 ) alkylsulfonyl group; (a12) (C 1 -C 8 ) haloalkylsulfonyl group; (a13) a carbamoyl
  • X 2 may be the same or different, (b2) a halogen atom; (b3) a (C 1 -C 8 ) alkyl group; (b4) (C 1 -C 8 ) haloalkyl group; (b5) (C 1 -C 8 ) alkoxy groups; (b6) (C 1 -C 8 ) haloalkoxy group; (b7) a carbamoyl group; (b8) an amino group; (b9) (C 1 -C 8 ) alkylamino group; (b10) (C 3 -C 8 ) cycloalkylamino group; (b11) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkylamino groups; (b12) (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkylamino groups; (b13) Bis (C 1 -C 8 ) alkylamino group (the alkyl groups may be the same
  • Y 1 is, (c1) hydrogen atom; (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c5) (C 1 -C 8 ) haloalkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c7) (C 1 -C 8 ) haloalkoxy group; (c8) (C 1 -C 8 ) alkylthio group; (c9) (C 1 -C 8 ) haloalkylthio group; (c10) (C 1 -C 8 ) alkylsulfinyl group; (c11) (C 1 -C 8 ) haloalkylsulfinyl group; (c12) (C 1 -C 8 ) alkylsulfonyl group; or (c13) represents a (C 1 -C 8 ) haloalkylsulfonyl group;
  • Y 2 may be the same or different, (d2) a halogen atom; (d3) a (C 1 -C 8 ) alkyl group; (d4) (C 1 -C 8 ) haloalkyl group; (d5) (C 1 -C 8 ) alkoxy group; (d6) (C 1 -C 8 ) haloalkoxy group; (d7) (C 1 -C 8 ) alkylthio group; (d8) (C 1 -C 8 ) haloalkylthio group; (d9) a (C 1 -C 8 ) alkylsulfinyl group; (d10) (C 1 -C 8 ) haloalkylsulfinyl group; (d11) (C 1 -C 8 ) alkylsulfonyl group; or (d12) represents a (C 1 -C 8 ) haloalkylsulfonyl group,
  • n 0, 1, or 2.
  • Z 1 , Z 2 , and Z 3 may be the same or different, and may be a nitrogen atom, CH, CY 2 , or C—AQ (where C—AQ is in the general formula (I)) , Z 1 , Z 2 , and Z 3 may be only bonded to one of them).
  • A represents a linear or branched (C 1 -C 8 ) alkylene group, Q represents a fused heterocyclic group selected from the group listed below.
  • W 1 may be the same or different, (e1) hydrogen atom; (e2) a halogen atom; (e3) a cyano group; (e4) formyl group; (e5) a cyano (C 1 -C 8 ) alkyl group; (e6) a (C 1 -C 8 ) alkyl group; (e7) (C 2 -C 8 ) alkenyl group; (e8) (C 2 -C 8 ) alkynyl group; (e9) (C 2 -C 8 ) haloalkenyl group; (e10) (C 3 -C 8 ) cycloalkyl group; (e11) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy groups; (e12) (C 1 -C 8 ) alkoxy group; (e13) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl
  • R 4 (R 5 ) N group (wherein R 4 and R 5 may be the same or different and are a hydrogen atom, a (C 1 -C 8 ) alkyl group, (C 3 -C 8 ) cyclo) Alkyl group, (C 2 -C 8 ) alkenyl group, (C 2 -C 8 ) alkynyl group, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group, (C 1 -C 8 ) haloalkyl Group, (C 3 -C 8 ) halocycloalkyl group, (C 1 -C 8 ) alkylcarbonyl group, (C 1 -C 8 ) alkoxycarbonyl group, aryl group, may be the same or different, and (a) halogen Atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 )
  • Arylcarbonyl group which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f ) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group (M) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • substituents selected from (p) (C 1 -C 8 ) alkylcarbonyl group, (q) carboxyl group, (r) (C 1 -C 8 ) alkoxycarbonyl group, and (s) phenoxy group (C 1 -C 8 ) alkyl group having a ring on the ring; heterocyclic group, which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group (E) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) Haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group,
  • (e38) an aryl group; (e39) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C
  • (e40) aryloxycarbonyloxy group; (e41) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (
  • (e43) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (e45) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (e47) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • W 2 , W 2a , W 2b and W 2c may be the same or different.
  • W 2 and W 3 can be combined to form a 5- to 8-membered saturated nitrogen-containing heterocycle containing one nitrogen atom.
  • (f6) a halogen atom;
  • (f7) (C 1 -C 8 ) alkoxy group; or
  • W 2b and W 2c may combine with each other to form an unsubstituted 5- to 8-membered saturated or unsaturated aliphatic ring together with the carbon atom to which they are bonded. Contains ⁇ 2 oxygen atoms.
  • W 3 and W 3a may be the same or different, (m1) hydrogen atom; (m2) cyano group; (m3) formyl group; (m4) a cyano (C 1 -C 8 ) alkyl group; (m5) a (C 1 -C 8 ) alkyl group; (m6) (C 2 -C 8 ) alkenyl group; (m7) (C 2 -C 8 ) alkynyl group; (m8) (C 2 -C 8 ) haloalkenyl group; (m9) (C 3 -C 8 ) cycloalkyl group; (m10) (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl groups; (m11) (C 1 -C 8 ) haloalkyl group; (m12) (C 3 -C 8 ) halocycloalkyl group; (m13) a (C 3 -C 8 ) halocycloalkyl (C 1
  • W 4 , W 5 , W 6 , and W 7 may be the same or different, (g1) hydrogen atom; (g2) a halogen atom; (g3) a cyano group; (g4) formyl group; (g5) a cyano (C 1 -C 8 ) alkyl group; (g6) (C 1 -C 8 ) alkyl group; (g7) (C 2 -C 8 ) alkenyl group; (g8) (C 2 -C 8 ) alkynyl group; (g9) (C 2 -C 8 ) haloalkenyl group; (g10) (C 3 -C 8 ) cycloalkyl group; (g11) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy groups; (g12) (C 1 -C 8 ) alkoxy group; (g13) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) al
  • R 1 is, (h1) a (C 1 -C 8 ) alkyl group; (h2) (C 2 -C 8 ) alkenyl group; (h3) (C 2 -C 8 ) alkynyl group; (h4) (C 3 -C 8 ) cycloalkyl group; (h5) a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (h6) a hydroxy (C 1 -C 8 ) alkyl group; (h7) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h8) a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; (h10) a (C 1 -C 8 ) alkyls
  • (h12) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8) haloalkyl group, (g) (C 1 -C 8) alkoxy groups, (h) (C 1 -C 8) haloalkoxy group, (i) (C 3 -C 8) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkylsulfon
  • (h13) an arylthio (C 1 -C 8 ) alkyl group; (h14) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalky
  • (h15) an aryl (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h16) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C
  • (h17) aryl (C 1 -C 8 ) alkyl; (h18) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulf
  • (h19) an aryloxy (C 1 -C 8 ) alkyl group; (h20) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkyl
  • (h21) an aryl (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h22) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1
  • an aryl (C 1 -C 8 ) alkoxycarbonyl (C 1 -C 8 ) alkyl group; (h24) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C
  • (h25) an arylcarbonyloxy (C 1 -C 8 ) alkyl group; (h26) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) halo
  • (h27) arylmethylideneiminooxy (C 1 -C 8 ) alkyl; (h28) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 )
  • (h29) an aryl (C 1 -C 8 ) alkoxyimino (C 1 -C 8 ) alkyl group; (h30) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (
  • B represents a linear or branched (C 1 -C 8 ) alkylene group
  • R 7 is (i1) represents a (C 1 -C 8 ) alkyl group
  • R 8 is (j1) hydrogen atom;
  • (j2) (C 1 -C 8 ) alkyl group;
  • (j3) a cyano group;
  • (j4) (C 1 -C 8 ) alkylcarbonyl group;
  • (j6) (C 1 -C 8 ) alkoxycarbonyl group;
  • (j7) an aryl group; (j8) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1
  • (j9) an arylsulfonyl group; or (j10) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group,
  • R 2 is (k1) hydrogen atom; (k2) (C 1 -C 8 ) alkyl group; (k3) (C 3 -C 8 ) cycloalkyl group; or (k4) represents a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; or (k5) R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom. It is also possible to form a good 5- to 8-membered saturated nitrogen-containing heterocycle.
  • R 3 is (l1) hydrogen atom; (l2) (C 1 -C 8 ) alkyl group; (l3) (C 3 -C 8 ) cycloalkyl group; or (l4) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl; Indicates. ] Or a salt thereof.
  • X 1 is (a1) hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 8 ) alkyl group; (a4) (C 1 -C 8 ) haloalkyl group; (a5) (C 1 -C 8 ) alkoxy group; (a6) (C 1 -C 8 ) haloalkoxy group; (a7) (C 1 -C 8 ) alkylthio group; (a8) (C 1 -C 8 ) haloalkylthio group; (a9) a (C 1 -C 8 ) alkylsulfinyl group; (a10) (C 1 -C 8 ) haloalkylsulfinyl group; (a11) (C 1 -C 8 ) alkylsulfonyl group; (a12) a (C 1 -C 8 ) haloalkylsulfonyl group,
  • the substituent other than X 1 is
  • X 2 is, (b2) a halogen atom; (b3) a (C 1 -C 8 ) alkyl group; (b4) (C 1 -C 8 ) haloalkyl group; (b5) (C 1 -C 8 ) alkoxy groups; (b6) a (C 1 -C 8 ) haloalkoxy group, Substituents other than X 2 are as defined in [1].
  • X 1 is (a1) hydrogen atom; (a2) a halogen atom; (a3) a (C 1 -C 8 ) alkyl group; (a4) (C 1 -C 8 ) haloalkyl group; (a5) (C 1 -C 8 ) alkoxy group; (a6) (C 1 -C 8 ) haloalkoxy group; (a7) (C 1 -C 8 ) alkylthio group; (a8) (C 1 -C 8 ) haloalkylthio group; (a9) a (C 1 -C 8 ) alkylsulfinyl group; (a10) (C 1 -C 8 ) haloalkylsulfinyl group; (a11) (C 1 -C 8 ) alkylsulfonyl group; (a12) a (C 1 -C 8 ) haloalkylsulfonyl group, X 2 is, (b2)
  • X 1 is (a1) hydrogen atom; (a2) a halogen atom; (a7) (C 1 -C 8 ) alkylthio group; (a9) a (C 1 -C 8 ) alkylsulfinyl group; or (a11) (C 1 -C 8 ) alkylsulfonyl group;
  • X 2 is, (b2) a halogen atom; m represents 0 or 1;
  • Y 1 is, (c1) hydrogen atom; (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c8) (C 1 -C 8 ) alkylthio group; or (c10) (C 1 -C 8 ) alkylsulfinyl group;
  • Indicate Y 2 is, (d2) a halogen atom; (d3) a (C 1 -C 8 ) alkyl group; (d4) (C 1 -C 8 ) haloalkyl group; (d5) (C 1 -C 8 ) alkoxy group; or (d6) (C 1 -C 8 ) haloalkoxy group; n represents 0 or 1.
  • Q is Q1, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q16, Q18, Q19, Q21, Q23, Q24, Q25, Q26, Q27, Q28, Q29, Q30
  • W 1 may be the same or different, (e1) hydrogen atom; (e4) Formyl group (e6) a (C 1 -C 8 ) alkyl group;
  • R 4 and R 5 may be the same or different and are a hydrogen atom, a (C 1 -C 8 ) alkyl group, (C 3 -C 8 ) cyclo) Alkyl group, (C 2 -C 8 ) alkenyl group, (C 2 -C 8 ) alkynyl group, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group, (C 1 -C 8 ) haloalkyl Group, (C 3 -C 8 ) halocycloalkyl group, (C 1 -C 8 ) alkylcarbonyl group, (C 1 -C 8 ) alkoxycarbonyl group,
  • Heterocyclic group which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f ) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group (M) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • R 4 (R 5 ) N (C 1 -C 8 ) alkyl group wherein R 4 and R 5 are the same as above); (e34) R 4 (R 5 ) NCO— group (wherein R 4 and R 5 are as defined above); (e35) R 4 (R 5 ) NCOO— group (wherein R 4 and R 5 are the same as above); (e36) R 4 (R 5 ) NSO 2 — group (wherein R 4 and R 5 are the same as above); (E37) R 4 (R 5) NCON (R 5) - group; (wherein, R 4 and R 5 is as defined above, R 5 together may be the same or different.)
  • (e38) an aryl group; (e39) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C
  • W 4 , W 5 , W 6 , and W 7 may be the same or different, (g1) hydrogen atom;
  • (g2) a halogen atom; (g6) (C 1 -C 8 ) alkyl group; (g12) (C 1 -C 8 ) alkoxy group; (g14) (C 1 -C 8 ) haloalkyl group; or (g27) (C 1 -C 8 ) alkoxycarbonyl group; P indicates 0.
  • R 1 is (h1) a (C 1 -C 8 ) alkyl group; (h2) (C 2 -C 8 ) alkenyl group; (h3) (C 2 -C 8 ) alkynyl group; (h5) a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (h7) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h8) a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; (h10) a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group; (h12) may be the same or different, (a) halogen atom, (b)
  • (h14) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h16) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h17) aryl (C 1 -C 8 ) alkyl; (h18) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulf
  • (h20) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h22) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h24) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h26) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h28) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h30) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • R 7 is (i1) represents a (C 1 -C 8 ) alkyl group
  • R 8 is (j1) hydrogen atom; (j2) (C 1 -C 8 ) alkyl group; (j3) a cyano group; (j4) (C 1 -C 8 ) alkylcarbonyl group; (j5) (C 1 -C 8 ) haloalkylcarbonyl group; (j6) (C 1 -C 8 ) alkoxycarbonyl group;
  • (j8) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyls
  • (j10) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyls
  • R 2 is (k1) hydrogen atom; or (k2) represents a (C 1 -C 8 ) alkyl group; (k5) or R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom
  • a 5- to 8-membered saturated nitrogen-containing heterocycle, which may be R 3 is (l1) hydrogen atom; or (l2) (C 1 -C 8 ) alkyl group; Showing, The phthalamide derivative according to [1] or a salt thereof represented by:
  • X 1 is (a2) represents a halogen atom; m represents 0.
  • Y 1 is the same or different, (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c8) (C 1 -C 8 ) alkylthio group; or (c10) a (C 1 -C 8 ) alkylsulfinyl group; n represents 0.
  • Z 2 represents CAQ.
  • Q represents Q1, Q8 or Q18, “where, W 1 is, (e1) hydrogen atom; (e4) formyl group; (e6) a (C 1 -C 8 ) alkyl group; (e10) (C 3 -C 8 ) cycloalkyl group; (e11) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy groups; (e12) (C 1 -C 8 ) alkoxy group; (e13) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (e14) (C 1 -C 8 ) haloalkyl group; (e15) (C 1 -C 8 ) haloalkoxy group; (e18) (C 1 -C 8 ) alkylthio group; (e19) (C 1 -C 8 ) alkylsulfinyl group; (e27) (C
  • R 4 (R 5 ) N group (wherein R 4 and R 5 may be the same or different and are a hydrogen atom, a (C 1 -C 8 ) alkyl group, (C 3 -C 8 ) cyclo) Alkyl group, (C 2 -C 8 ) alkenyl group, (C 2 -C 8 ) alkynyl group, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group, (C 1 -C 8 ) haloalkyl Group, (C 3 -C 8 ) halocycloalkyl group, (C 1 -C 8 ) alkylcarbonyl group, (C 1 -C 8 ) alkoxycarbonyl group, aryl group, may be the same or different, and (a) halogen Atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 )
  • substituents selected from (p) (C 1 -C 8 ) alkylcarbonyl group, (q) carboxyl group, (r) (C 1 -C 8 ) alkoxycarbonyl group, and (s) phenoxy group May be the same or different, and (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C 1- C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) ( C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy, (j) (C 1 -C 8 ) alkylthio, (k) (C 1 -C 8 ) haloalkylthio, (
  • Aryl (C 1 -C 8 ) alkyl groups which may be the same or different, (a) halogen atoms, (b) cyano groups, (c) nitro groups, (d) formyl groups, (e) (C 1 -C 8 ) an alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy, (j) (C 1 -C 8 ) alkylthio, (k) (C 1 -C 8 ) haloalkylthio, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (
  • W 2 , W 2a and W 2b may be the same or different, (f1) hydrogen atom; (f2) a (C 1 -C 8 ) alkyl group; or
  • W 3 and W 3a may be the same or different, (m1) hydrogen atom; (m2) cyano group; (m4) a cyano (C 1 -C 8 ) alkyl group; (m5) a (C 1 -C 8 ) alkyl group; (m6) (C 2 -C 8 ) alkenyl group; (m7) (C 2 -C 8 ) alkynyl group; (m8) (C 2 -C 8 ) haloalkenyl group; (m9) (C 3 -C 8 ) cycloalkyl group; (m10) (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl groups; (m11) (C 1 -C 8 ) haloalkyl group; (m14) a (C 1 -C 8 ) alkylthio (C 1 -C 8 )
  • W 4 , W 5 , W 6 , and W 7 may be the same or different, (g1) hydrogen atom; (g2) a halogen atom; (g6) (C 1 -C 8 ) alkyl group; (g12) (C 1 -C 8 ) alkoxy group; or (g14) (C 1 -C 8 ) haloalkyl group; p is 0. "
  • R 1 is (h1) a (C 1 -C 8 ) alkyl group; (h2) (C 2 -C 8 ) alkenyl group; (h3) (C 2 -C 8 ) alkynyl group; (h5) a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (h7) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h8) a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; (h10) a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group;
  • (h14) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h16) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h18) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h20) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h22) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h24) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h28) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h30) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • R 8 is (j1) hydrogen atom; (j3) a cyano group; or (j5) represents a (C 1 -C 8 ) haloalkylcarbonyl group, and t represents 0 or 1.
  • R 2 is (k1) hydrogen atom; or (k2) represents a (C 1 -C 8 ) alkyl group; (k5) or R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom A 5- to 8-membered saturated nitrogen-containing heterocycle may be formed.
  • R 3 is (l1) hydrogen atom; or (l2) (C 1 -C 8 ) alkyl group;
  • [7] [1] An agricultural and horticultural insecticide comprising the phthalamide derivative or a salt thereof according to any one of [1] to [6] as an active ingredient. [8] [7] A method for using an agricultural and horticultural insecticide according to [7], wherein the plant or soil is treated with an effective amount of the agricultural and horticultural insecticide. [9] An animal parasite control agent comprising the phthalamide derivative or a salt thereof according to any one of [1] to [6] as an active ingredient.
  • the phthalamide derivatives or salts thereof of the present invention have structural features such as having a condensed heterocyclic group that a conventional compound does not have.
  • the compound of the present invention exhibits an excellent effect not only on lepidopterous pests but also on thrips, coleoptera, flies and stink bugs.
  • the compound of the present invention has an insecticidal effect against thrips pests, which is not disclosed or suggested in the prior art and is a feature that a conventional similar compound does not have.
  • the above-mentioned compounds of the present invention are also effective against pests parasitic on pets such as dogs and cats or livestock such as cows and sheep.
  • Halo means “halogen atom” and represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom
  • (C 1 -C 8 ) alkyl group means, for example, a methyl group, an ethyl group, a normal group, Propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group 1-methylbutyl group, normal hexyl group, isohexyl group, 1,1,2-
  • (C 2 -C 8) alkenyl group include vinyl group, allyl group, Isopurope Group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3, A linear or branched alkenyl group having 2 to 8 carbon atoms such as a 3-dimethyl-1-butenyl group, a heptenyl group, an octenyl group, etc .;
  • (C 2 -C 8 ) alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl
  • Straight chain or branched chain carbon atoms of 2 to 8 such as 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3,3-dimethyl-1-butynyl group, heptynyl group, octynyl group, etc.
  • An alkynyl group is shown.
  • (C 3 -C 8 ) cycloalkyl means, for example, a cyclic alkyl having 3 to 8 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
  • a “(C 1 -C 8 ) alkoxy group” means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy Group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group 1,1,2-trimethylpropyloxy group, heptylo Shi group, a linear or branched C 1 -C 8 alkoxy group such as octyl group, a "(C 2 -C 8) alkenyloxy group", for example, propenyloxy group, butenyloxy A linear or branched alkenyloxy group having 2 to 8 carbon atoms, such as a group
  • (C 1 -C 8 ) alkylthio group means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group, heptylthio group, octylthio group and the like, which are linear or branched alkylthio groups having 1 to 8 carbon atoms, such as “(C 1 -C 8 ) alkylsulfin
  • Inyl group isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropyl Straight chain such as sulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, isohexylsulfinyl group, 1,1,2-trimethylpropylsulfinyl group, heptylsulfinyl group, octylsulfinyl group, etc.
  • alkylsulfinyl group indicates branched 1-8 carbon atoms alkylsulfinyl group, a "(C 1 -C 8) alkylsulfonyl group", for example, methylsulfonyl group, Tylsulfonyl group, normal propylsulfonyl group, isopropylsulfonyl group, normal butylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulf
  • the “(C 2 -C 8 ) alkenylthio group” means, for example, a linear or branched carbon atom number 2 such as propenylthio group, butenylthio group, pentenylthio group, hexenylthio group, heptenylthio group, octenylthio group, etc.
  • (C 2 -C 8 ) alkenylsulfinyl group means, for example, linear or branched chain such as propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group, hexenylsulfinyl group, heptenylsulfinyl group, octenylsulfinyl group, etc.
  • alkenylsulfinyl group having 2 to 8 carbon atoms and “(C 2 -C 8 ) alkynylsulfinyl group” means, for example, propynylsulfinyl group, butynylsulfinyl group, pentynylsulfinyl group, hexynylsulfinyl group A straight chain or branched chain alkynylsulfinyl group having 2 to 8 carbon atoms such as a group, heptynylsulfinyl group, octynylsulfinyl group and the like.
  • (C 2 -C 8 ) alkenylsulfonyl group means, for example, linear or branched chain such as propenylsulfonyl group, butenylsulfonyl group, pentenylsulfonyl group, hexenylsulfonyl group, heptenylsulfonyl group, octenylsulfonyl group, etc.
  • alkenylsulfonyl group having 2 to 8 carbon atoms and “(C 2 -C 8 ) alkynylsulfonyl group” means, for example, propynylsulfonyl group, butynylsulfonyl group, pentynylsulfonyl group, hexynylsulfonyl group A straight chain or branched chain alkynylsulfonyl group having 2 to 8 carbon atoms such as a group, heptynylsulfonyl group, octynylsulfonyl group and the like;
  • (C 1 -C 8 ) alkyl group “(C 2 -C 8 ) alkenyl group”, “(C 2 -C 8 ) alkynyl group”, “(C 3 -C 8 ) cycloalkyl group”, “(C 1 -C 8 ) alkoxy”, “(C 2 -C 8 ) alkynyloxy”, “(C 3 -C 8 ) cycloalkyl”, “(C 1 -C 8 ) alkoxy”
  • One or two or more halogen atoms may be substituted at substitutable positions. When two or more halogen atoms are substituted, the halogen atoms may be the same or different.
  • Halo (C 1 -C 8 ) alkyl “Halo (C 2 -C 8 ) alkenyl”, “Halo (C 2 -C 8 ) alkynyl”, “Halo (C 3 -C 8 )”, respectively “Cycloalkyl group”, “halo (C 1 -C 8 ) alkoxy group”, “halo (C 1 -C 8 ) alkylthio group”, “halo (C 1 -C 8 ) alkylsulfinyl group”, “halo (C 1 -C 8 ) alkylsulfonyl group "and” halo (C 3 -C 8 ) cycloalkyl group ".
  • aryl group refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group and the like.
  • expressions such as “(C 1 -C 8 )”, “(C 2 -C 8 )”, “(C 3 -C 8 )” indicate the range of the number of carbon atoms of various substituents. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “(C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group”, a linear or branched chain It indicates that an alkoxy group having 1 to 8 carbon atoms is bonded to a linear or branched alkyl group having 1 to 8 carbon atoms.
  • a linear or branched carbon number of 1 to It indicates that 8 alkoxy groups and a cyclic alkyl group having 3 to 8 carbon atoms are bonded to a linear or branched alkyl group having 1 to 8 carbon atoms.
  • Examples of the “(C 1 -C 8 ) alkylene group” include a methylene group, an ethylene group, a propylene group, an isopropylene group, and a butylene group.
  • W 2 and W 3 are combined to form one nitrogen atom, and further include 1 to 2 identical or different heteroatoms selected from oxygen atom, nitrogen atom and sulfur atom.
  • Preferable 5- to 8-membered nitrogen-containing heterocyclic rings include pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and the like.
  • Heterocyclic group and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms.
  • Examples of the ⁇ aromatic heterocyclic group '' include, for example, furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl and the like Cyclic aromatic heterocyclic groups; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, indazolyl, pyrrolopyrazinyl, imidazopyr Aromatic condensed heterocycl
  • non-aromatic heterocyclic group examples include oxiranyl, thiylyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, azolidinyl, oxazolidinyl, oxazolidinyl, Imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-1,3-oxazolidin-5-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1- Dioxide tetrahydropyranyl,
  • heterocyclic group examples include isoquinolinyl, tetrazolyl, quinolinyl, isoxazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrazolyl, benzimidazolyl, 2,3-dioxoisoindolyl, tetrahydrofuranyl, oxiranyl, thienyl, pyridazinyl and the like. It is done.
  • Examples of the salt of the phthalamide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate and oxalate. And organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.
  • inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate and oxalate.
  • organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate
  • salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion
  • the phthalamide derivative represented by the general formula (I) and the salt thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers and diastereomers may be present.
  • the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio.
  • the phthalamide derivative represented by the general formula (I) and the salt thereof of the present invention may have two kinds of geometric isomers derived from a carbon-carbon or carbon-nitrogen double bond in the structural formula.
  • the present invention encompasses all geometric isomers and mixtures containing them in any proportion.
  • X 1 is (a1) hydrogen atom; (a2) a halogen atom; (a7) (C 1 -C 8 ) alkylthio group; (a9) a (C 1 -C 8 ) alkylsulfinyl group; or (a11) (C 1 -C 8 ) alkylsulfonyl group;
  • X 2 is, (b2) a halogen atom; m represents 0 or 1; Y 1 is (c1) hydrogen atom; (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c8) (C 1 -C 8 ) alkylthio group; or (c10) (C 1 -C 8 ) alkylsulfinyl group; Indicate Y 2 is, (d2) a halogen atom; (d3) a (C 1 -C 8 ) alkyl group; (d4) (C 1 -C 8 ) haloalkyl group; (d5) (C 1 -C 8 ) alkoxy group; or (d6) (C 1 -C 8 ) haloalkoxy group; n represents 0 or 1;
  • Q is Q1, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q13, Q16, Q18, Q19, Q21, Q23, Q24, Q25, Q26, Q27, Q28, Q29, Q30
  • W 1 may be the same or different, (e1) hydrogen atom; (e2) a halogen atom; (e6) a (C 1 -C 8 ) alkyl group; (e10) (C 3 -C 8 ) cycloalkyl group;
  • R 4 (R 5 ) N group (wherein R 4 and R 5 may be the same or different and are a hydrogen atom, a (C 1 -C 8 ) alkyl group, (C 3 -C 8 ) cyclo) Alkyl group, (C 2 -C 8 ) alkenyl group, (C 2 -C 8 ) alkynyl group, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group, (C 1 -C 8 ) haloalkyl Group, (C 3 -C 8 ) halocycloalkyl group, (C 1 -C 8 ) alkylcarbonyl group, (C 1 -C 8 ) alkoxycarbonyl group, aryl group, may be the same or different, and (a) halogen Atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 )
  • Arylcarbonyl group which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f ) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group (M) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • Aryl (C 1 -C 8 ) alkyl groups which may be the same or different, (a) halogen atoms, (b) cyano groups, (c) nitro groups, (d) formyl groups, (e) (C 1 -C 8 ) an alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy, (j) (C 1 -C 8 ) alkylthio, (k) (C 1 -C 8 ) haloalkylthio, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (
  • a halogen atom may be identical or different, (a) a halogen atom, (b) a cyano group, (c) nitro group, (d) formyl, (e) (C 1 -C 8) alkyl group, (f) (C 1- C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m ) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • R 4 (R 5 ) N (C 1 -C 8 ) alkyl group wherein R 4 and R 5 are the same as above
  • R 4 (R 5 ) NCO— group wherein R 4 and R 5 are as defined above
  • R 4 (R 5 ) NCOO— group wherein R 4 and R 5 are the same as above
  • W 4 , W 5 , W 6 , and W 7 may be the same or different, (g1) hydrogen atom; (g2) a halogen atom; (g6) (C 1 -C 8 ) alkyl group; (g12) (C 1 -C 8 ) alkoxy group; (g14) (C 1 -C 8 ) haloalkyl group; or (g27) (C 1 -C 8 ) alkoxycarbonyl group; P indicates 0. "
  • R 1 is (h1) a (C 1 -C 8 ) alkyl group; (h2) (C 2 -C 8 ) alkenyl group; (h3) (C 2 -C 8 ) alkynyl group; (h5) a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (h7) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h8) a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; (h10) a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group;
  • (h12) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8) haloalkyl group, (g) (C 1 -C 8) alkoxy groups, (h) (C 1 -C 8) haloalkoxy group, (i) (C 3 -C 8) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkylsulfon
  • (h14) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h16) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h18) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h20) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h22) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h24) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h26) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h28) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h30) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • R 7 is (i1) represents a (C 1 -C 8 ) alkyl group
  • R 8 is (j1) hydrogen atom; (j2) (C 1 -C 8 ) alkyl group; (j3) a cyano group; (j4) (C 1 -C 8 ) alkylcarbonyl group; (j5) (C 1 -C 8 ) haloalkylcarbonyl group; (j6) (C 1 -C 8 ) alkoxycarbonyl group;
  • (j8) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyls
  • (j10) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyls
  • R 2 is (k1) hydrogen atom; or (k2) represents a (C 1 -C 8 ) alkyl group; (k5) or R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom
  • a 5- to 8-membered saturated nitrogen-containing heterocycle, which may be R 3 is (l1) hydrogen atom; or (l2) (C 1 -C 8 ) alkyl group.
  • X 1 is (a2) represents a halogen atom; m represents 0.
  • Y 1 is the same or different, (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c8) (C 1 -C 8 ) alkylthio group; or (c10) a (C 1 -C 8 ) alkylsulfinyl group; n represents 0.
  • Z 2 represents CAQ.
  • Q represents Q1, Q8 or Q18, “where, W 1 is, (e1) hydrogen atom; (e6) a (C 1 -C 8 ) alkyl group; (e10) (C 3 -C 8 ) cycloalkyl group; (e11) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy groups; (e12) (C 1 -C 8 ) alkoxy group; (e13) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (e14) (C 1 -C 8 ) haloalkyl group; (e15) (C 1 -C 8 ) haloalkoxy group;
  • R 4 (R 5 ) N group (wherein R 4 and R 5 may be the same or different and are a hydrogen atom, a (C 1 -C 8 ) alkyl group, (C 3 -C 8 ) cyclo) Alkyl group, (C 2 -C 8 ) alkenyl group, (C 2 -C 8 ) alkynyl group, (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group, (C 1 -C 8 ) haloalkyl Group, (C 3 -C 8 ) halocycloalkyl group, (C 1 -C 8 ) alkylcarbonyl group, (C 1 -C 8 ) alkoxycarbonyl group, aryl group, may be the same or different, and (a) halogen Atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 )
  • Arylcarbonyl group which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f ) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group (M) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • Aryl (C 1 -C 8 ) alkyl groups which may be the same or different, (a) halogen atoms, (b) cyano groups, (c) nitro groups, (d) formyl groups, (e) (C 1 -C 8 ) an alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy, (j) (C 1 -C 8 ) alkylthio, (k) (C 1 -C 8 ) haloalkylthio, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (
  • Heterocyclic group which may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f ) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group (M) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 )
  • a heterocycle (C 1 -C 8 ) alkyl group which may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) ( C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsul
  • W 2 and W 2a may be the same or different (f1) hydrogen atom; (f2) a (C 1 -C 8 ) alkyl group; or (f3)
  • W 3 is, (m1) hydrogen atom; (m2) cyano group; (m4) a cyano (C 1 -C 8 ) alkyl group; (m5) a (C 1 -C 8 ) alkyl group; (m6) (C 2 -C 8 ) alkenyl group; (m7) (C 2 -C 8 ) alkynyl group; (m8) (C 2 -C 8 ) haloalkenyl group; (m9) (C 3 -C 8 ) cycloalkyl group; (m10) (C 1 -C 8 ) alkoxy (C 1 -C 8 )
  • W 4 , W 5 , W 6 , and W 7 may be the same or different, (g1) hydrogen atom; (g2) a halogen atom; (g6) (C 1 -C 8 ) alkyl group; (g12) (C 1 -C 8 ) alkoxy group; or (g14) (C 1 -C 8 ) haloalkyl group; p is 0. "
  • R 1 is (h1) a (C 1 -C 8 ) alkyl group; (h2) (C 2 -C 8 ) alkenyl group; (h3) (C 2 -C 8 ) alkynyl group; (h5) a (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (h7) a (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl group; (h8) a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; (h10) a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group;
  • (h14) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h16) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h18) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h20) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h22) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h24) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 3 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h28) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • (h30) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 8 ) alkyl group, (f) (C 1 -C 8 ) haloalkyl group, (g) (C 1 -C 8 ) alkoxy group, (h) (C 1 -C 8 ) haloalkoxy group, (i) (C 5 -C 8 ) cycloalkyl ( C 1 -C 8 ) alkoxy group, (j) (C 1 -C 8 ) alkylthio group, (k) (C 1 -C 8 ) haloalkylthio group, (l) (C 1 -C 8 ) alkylsulfinyl group, (m) (C 1 -C 8 ) haloalkylsulfinyl group, (n) (C 1 -C 8 ) alkyl
  • R 2 is (k1) hydrogen atom; or (k2) represents a (C 1 -C 8 ) alkyl group; (k5) or R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 identical or different heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom A 5- to 8-membered saturated nitrogen-containing heterocycle may be formed.
  • R 3 is (l1) hydrogen atom; or (l2) (C 1 -C 8 ) alkyl group.
  • -X 1 represents (a2) a halogen atom; and m represents 0.
  • Y 1 is the same or different and represents (c4) (C 1 -C 8 ) alkyl group; and n represents 0.
  • Z 2 represents CAQ and Q represents Q8 “where W 3 is an (m5) (C 1 -C 8 ) alkyl group; (m9) (C 3 -C 8 ) A cycloalkyl group; or (m11) (C 1 -C 8 ) haloalkyl.
  • W 4 , W 5 , W 6 and W 7 may be the same or different and each represents (g1) a hydrogen atom; or (g14) (C 1 -C 8 ) haloalkyl group.
  • R 1 is a (h8) (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group; (h9) (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; or ( h10) a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group;
  • -R 2 is (k1) a hydrogen atom and R 3 is (l1) a hydrogen atom.
  • the compound which has 1 or 2 or more of each substituent which the above-mentioned or the following preferable aspect or specific compound has is preferable.
  • the phthalamide derivative represented by the general formula (I) can be produced by reacting with the compound represented by the general formula (V) or (VI) in the presence of a base in an inert solvent.
  • Hydrocarbons such as chlorobenzene, dichlorobenzene and fluorobenzene, chain or cyclic ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide and dimethylacetamide
  • Inert solvents such as amides, acids such as acetic acid, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and the like, and these inert solvents may be used alone or in combination of two or more. Can be used.
  • each reactant may be used in an equimolar amount, but amines represented by general formula (III) or general formula (IV) may be used in excess.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating from a reaction system.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogenated compounds such as chlorobenzene, dichlorobenzene and fluorobenzene.
  • Aromatic hydrocarbons linear or cyclic ethers such as methyl tertiary butyl ether, diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide, dimethylacetamide,
  • An inert solvent such as 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.
  • Examples of the base used in this reaction include organic bases such as triethylamine and pyridine, inorganic bases such as potassium carbonate, sodium bicarbonate, sodium carbonate and sodium hydroxide, Examples thereof include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride, alkali metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide, butyl lithium and the like.
  • the amount used may be appropriately selected from the range of equimolar to excess molar relative to the phthalamide derivative represented by the general formula (I-1) or (I-2).
  • reaction temperature can be from room temperature to the reflux temperature of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.
  • the target product After completion of the reaction, it may be isolated from the reaction system containing the target product according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • compounds showing a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group in the definition of R 1 in the general formulas (I), (I-1) and (I-2) are those skilled in the art. Is usually carried out by oxidation with an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide, so that R 1 is a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group, Alternatively, a compound showing a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group can be produced. In addition, sulfur atoms present in Q26 and Q30 can be similarly oxidized to produce sulfoxy compounds and sulfones.
  • the derivatives represented by the general formula (III) are novel compounds, for example, the general formula (III-1) (Wherein Y 1 , Y 2 , Z 1 , Z 2 , Z 3 , n, A and M are the same as above), and a compound represented by the general formula (VII)
  • a compound represented by the general formula (III-2) can be produced by reacting the derivative represented by the formula (III-2) in the presence of a base in an inert solvent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • chain or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane; petroleum ether, ligroin, ethyl Chain or cyclic ethers such as ether, methyl tertiary butyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); halogens such as methylene chloride, chloroform, carbon tetrachloride Hydrocarbons; aromatic hydrocarbons such as benzene, toluene, xylene; halogenated aromatic hydrocarbons such as chlorobenzene, fluorobenzene, dichlorobenzene; acetone, methyl ethyl ketone (MEK), methyl-i Ketones such as propyl ketone and methyl isobutyl
  • Bases that can be used in this reaction include alkali metal carbonates and bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide.
  • Alkali metal such as alkali metal and alkaline earth metal hydroxide, alkali metal amide such as lithium amide, sodium amide, potassium amide, etc., hydride of alkali metal such as lithium hydride, sodium hydride, potassium hydride, etc.
  • Alkali metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide, etc., triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, Pyridine, 4-dimethyl Organic bases such as minopyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO) and 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) it can.
  • the amount used can be appropriately selected within the range of 1 molar equivalent to 10 molar equivalents relative to the compound represented by the general formula (III-1).
  • phase transfer catalyst can be used in this reaction, for example, tetramethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide, tetrabutylammonium bissulfate, tetrabutylammonium iodide, trioctylmethylammonium chloride, benzyl Quaternary ions such as triethylammonium bromide, butylpyridinium bromide, heptylpyridinium bromide, benzyltriethylammonium chloride; crown ethers such as dibenzo-18-crown-6, dicyclohexyl-18-crown-6, 18-crown-6 [2.2.2] -cryptate, [2.1.1] -cryptate, [2.2.1] -cryptate, [2.2.
  • each reactant may be used in an equimolar amount, but either of the derivatives represented by general formula (III-1) or general formula (VII) may be used in excess. it can.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, it is also possible to use for the next reaction process, without isolating from a reaction system.
  • the compound of the general formula (III-1) is a known publication, Chem. B Abstr. 58, 3444e (1963); Bull. Soc. Chim. Fr. (1934) 539-545; Chem. Res. Miniprint, Vol. 8 (1987), 2133-2139; Chem. Soc. B, (1967), 1154-1158; Chem. Soc. (1961), 221-222; Amer. Chem. Soc. 111, 1989, 5880-5886, and the like.
  • Specific examples include 4-nitrobenzyl chloride (commercially available), 4-bromobenzyl chloride (commercially available), 2-chloro-4-nitrobenzyl chloride, 2-methyl-4-nitrobenzyl chloride, 2-methoxy-4-nitro.
  • nitro-substituted benzoic acids and esters thereof used as a raw material for the derivative represented by the general formula (III-1) are disclosed in, for example, Chem. Ber. 52, 1919, 1083; Bull. Soc. Chim. Fr. (1962), 2255-2261; Tetrahedron, (1985), 115-118; Chem. Pharm. Bull. 41, (1993), pages 894-906, etc., and can be produced by a method described in the document or a method analogous thereto.
  • the derivative represented by the general formula (III-2) obtained by the above reaction is for example, an aniline derivative represented by the general formula (III-3) can be produced by reduction according to the method described in New Experimental Chemistry Lecture 14 Oxidation and Reduction [II] (Maruzen Co., Ltd.). it can.
  • the amine derivative represented by general formula (IV) can be manufactured according to the method described in the international publication 2001-23350 pamphlet, for example.
  • Manufacturing method 3-1 Manufacturing method of Q1 ' (W 1 , W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Manufacturing method 3-2 Manufacturing method of Q2 ', Q3', Q4 ' (W 1 , W 4 , W 5 , W 6 and W 7 are the same as above.) Similarly, derivatives represented by the general formulas Q2 ′, Q3 ′, and Q4 ′ are disclosed in production method 2-1, for example, from diaminopyridines (Qb, Qc, Qd) substituted with a heptafluoroisopropyl group. According to the method, imidazopyridines can be produced.
  • Manufacturing method 3-3 Manufacturing method of Q8 ' (W 3 , W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula (Q8 ′) are described in 4-heptafluoroisopropyl-1,2-phenylenediamine (Qa) from J.P. Heterocycl. Chem. 2, (1965), p. 41, 5- (heptafluoroisopropyl) benzimidazolin-2-one can be produced.
  • N 1 -cyclopropyl-4-fluoro-5-heptafluoroisopropyl-1,2-phenylenediamine (Qa ′), which can be produced according to the method described in JP-A-2001-122636, 1-cyclopropyl-5-fluoro-6- (heptafluoroisopropyl) benzimidazolin-2-one can be prepared.
  • Production method 3-4 Manufacturing method of Q9 ', Q10' (W 3 , W 4 , W 5 , W 6 and W 7 are the same as above.) Similarly, imidazopyridines (Q9 ′, Q10 ′) can be produced from diaminopyridines Qb ′, Qd ′ substituted with a heptafluoroisopropyl group according to the production method described in Production Method 2-3.
  • Production method 3-5 Manufacturing method of Q6 ' (W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula (Q6 ′) are, for example, 2-methyl-4- (heptafluoroisopropyl) aniline (Qe) described in JP-A No. 2001-122836, Org. Synth. According to the method described in Volume 20, (1940), p. 73, 5-heptafluoroisopropyl-1H-indazole can be produced.
  • Production method 3-6 Manufacturing method of Q18 'and Q19' (Wherein, W 2, W 2a, W 3, W 4, W 5, W 6 and W 7 are the same .R the alkyl group of C 1 ⁇ 6, Hal represents a halogen atom.)
  • the derivatives represented by the general formula (Q18 ′) are, for example, from methyl 2-chloromethyl-4- (heptafluoroisopropyl) phenylcarbamate (Qf) and 2-methoxyethylamine described in JP-A No. 2001-342186. 3- (2-methoxyethyl) -6-heptafluoroisopropyl-3,4-dihydro-1H-quinazolin-2-one can be prepared.
  • Production method 3-7 Manufacturing method of Q11 ' (W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula (Q11 ′) can be obtained from 2-amino-5-heptafluoroisopropylphenol (Qh) described in JP-A No. 2001-122836 from Heterocycl. Chem. 2, (1965), page 41, 6- (heptafluoroisopropyl) benzoxazolin-2-one can be produced.
  • Production method 3-8 Manufacturing method of Q13 ' (W 4 , W 5 and W 6 are the same as above.)
  • the derivatives represented by the general formula (Q13 ′) can be produced from 2-amino-3-hydroxypyridines (Qi) according to the method disclosed in Production Method 2-7.
  • Q12 ′ 2-amino-5-heptafluoroisopropylthiophenol (Qj), which can be produced by the method described in JP-A-2001-122836, according to J. Am. Heterocycl. Chem. 2, (1965), page 41, 6- (heptafluoroisopropyl) benzothiazolin-2-one can be produced.
  • Qj 2-amino-5-heptafluoroisopropylthiophenol
  • Production method 3-10 Manufacturing method of Q5 ' (W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula (Q5 ′) include, for example, 4-heptafluoroisopropyl-1,2-phenylenediamine (Qa) described in JP-A No. 2001-122836, Org. Synth. 3, 3-106 (1955), 5-heptafluoroisopropyl-1H-benzotriazole can be produced.
  • Q24 ′ Manufacturing method of Q24 'and Q29' (W 2 , W 2a , W 2b , W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula (Q24 ′) can be prepared from 2-amino-5-heptafluoroisopropylbenzyl alcohol (Qk), which can be produced by the method described in JP-A No. 2001-122836, from J.A. Heterocycl. Chem. 2, (1965), page 41, 7- (heptafluoroisopropyl) benzoxazin-3-one can be produced.
  • Ql 2-amino-5-heptafluoroisopropylphenethyl alcohols
  • J. Org. Heterocycl. Chem. 2, (1965) page 41, 8- (heptafluoroisopropyl) benzoxazepin-4-one can be produced.
  • Production method 3-13 Manufacturing method of Q28 ' (W 4 , W 5 , W 6 and W 7 are the same as above.)
  • the derivatives represented by the general formula (Q28 ′) can produce 1H-quinoxalin-2-one by, for example, dehydrating condensation of (Qa) and trifluoropyruvic acid ester described above and cyclization. it can.
  • Production method 3-14 Manufacturing method of Q14 'and Q15' (W 3 , W 4 , W 5 , W 6 , W 7 and A are the same as above.)
  • Derivatives represented by the general formula (Q14 ′) include (Qa) and 3-methyl-4-nitrophenylacetic acid ester described above in J. Org. Am. Chem. Soc. 75, (1953), p. 1292, by condensation.
  • Compounds of the general formula (Q15 ′) are obtained by combining (Qh) described above with 3-methyl-4-nitrophenylacetic acid esters, Am. Chem. Soc. 75, (1953), p. 1292, by condensation.
  • Production method 3-15 Manufacturing method of Q7 ' (W 1 , W 4 , W 5 , W 6 and W 7 are the same as above.)
  • the derivatives represented by the general formula (Q7 ′) can be produced by subjecting the indole derivative (Qo) to heptafluoroisopropylation by the method described in JP-A-2001-122836.
  • the compound of Q16 is produced by a production method 3-10. It can be manufactured by the same method as the manufacturing method of Q5 ′.
  • the compound of Q17 can produce the corresponding phthalic imide compound by reacting the corresponding phthalic diester compound with ammonia.
  • the compound of Q21 is produced by the production method 3-3. It can manufacture according to the manufacturing method of Q8 '.
  • Q23 is a manufacturing method 3-1. It can manufacture according to the manufacturing method of Q1 '.
  • the compounds of Q25 and Q27 can be produced by the production method 3-12. It can manufacture according to the manufacturing method of Q26 '.
  • As the compound of Q31, the corresponding urea compound is produced by the production method 3-7. It can manufacture according to the manufacturing method of Q11 '.
  • Typical examples of the phthalamide derivative represented by the general formula (I) of the present invention are shown in Tables 1 to 31 below, but the present invention is not limited to these.
  • n- represents normal
  • iso represents iso
  • t- represents tertiary
  • c- represents alicyclic hydrocarbon group
  • Ph represents phenyl group
  • * Indicates enantiomer S form.
  • the physical properties indicate melting point (° C.) or refractive index n D (measurement temperature; ° C.).
  • the compounds described as “NMR” in the physical property column show 1 H-NMR data in Table 32.
  • the agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry, horticultural, and stored grains that harm paddy rice, fruit trees, vegetables, other crops, and flowers. It is suitable for pest control such as pests, sanitary pests, and nematodes.
  • Lepidoptera examples include the following: Lepidoptera (Lepidoptera) pests include, for example, Aura moth (Parasa consocia), red killer whale (Anomis mesogona), swallowtail (Papilio xuthus), azukiyamamushiga (Matsumuraeses azukivora), azuki nomeiga (Ostrinia scapulalis), optera a emptera White butterfly (Hyphantria cunea), Common squirrel (Ostrinia furnacalis), Common squirrel (Pseudaletia separata), Common squirrel (Tinea translucens), Common squirrel (Bactra furfurana), Common squirrel (Parnara guttata), Common squirrel Sesamia inferens, Brachmia triannulella, Monema flavescens, Nettle squirrels (Trichoplusia ni), Pleuroptya ruralis, Cystidia
  • insects of the order of the Hemiptera include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Trigonotylus coelestialium, etc.
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Aohamuri (Eucetonia roelofsi), Azuki weevil (Callosobruchus chinensis), Alci Weevil (Hypera postica), Green weevil (Echinocnemus squameus), Rice beetle (Oulema oryzae), Rice beetle (Oulema orzae) Ladybird (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), weevil (Aulacophora femoralis) Pea weevil (Bruchus pisorum), giant stag beetle (E
  • Diptera (Flyidae) pests include, for example, Culex pipiens pallens, red winged fly flies (Pegomya hyoscyami), red winged fly flies (Liriomyza huidobrensis), house flies (Musca domestica), rice flies Sandy fly (Hydrellia sasakii), Agromyza oryzae, Scarlet flyfly (Hydrellia griseola), Whiteflies (Hydrellia ⁇ ⁇ griseola), Common beetle (Ophiomyia phaseoli), Drosophila cucumber Fly flies such as Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis, Clogmia albipunctata, Tipula alex niorhynchus), Anopheles sinensis, radish fly (Hylemya brassicae), soybean fly
  • Hymenoptera pests (Pristomyrmex ponnes), Arachibachie, Moneorumium pharaohnis, Pheidole noda, Athalia rosae, Cristodon (Dryocosmus kurius), japonica), hornets, black bee wasp (Athalia infumata), horned bee (Arge pagana), Japanese bee (Athalia japonica), hachiriari (Acromyrmex spp.), fire ant (Solenopsis spp.), apple bee (Arge pa) Ruriari (Ochetellus glaber),
  • insects of the order Diptera include, butterfly (Homorocoryphus lineosus), kerat (Gryllotalpa sp.), Coago (Oxya hyla intricata), Cobainago (Oxya yezoensis), Tosama locust (Locusta migraya), Oneya ⁇ p Himeksakiri (Homorocoryphus jezoensis), and Emma cricket (Teleogryllus emma),
  • thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Thrips thrips (Haplothrips aculeatus), Thrips thrips, obscurus), black thrips (Lisrips floridensis), gladiolus thrips (Thrips simplex), black thrips (Thrips nigropilosus), black thrips (Heliothrips haemorrhoidalis), blue thrips Thrips (Leeuwenia pasanii), Shiimaruda thrips (Litotetothrips pasaniae), Citrus srips (Scirtothrips citri), Thrips thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines) Thrips Thrips hawaiiensis, Haplothrips kurdjumovi,
  • Examples of the pests of the mite include: Leptotrombidium akamushi, American dock chick (Dermacentor variabilis), house dust mite (Ornithonyssus bacoti), black mite (Demodex canis), mite (Rhipicephalus sanguineus) Tetranychus ludeni, Tetranychus truncatus, Mite spider mite (Tetranychus viennensis), Kanzawa spider mite (Tetranychus kanzawai), Stag beetle mite (Cheyletus malaccensis), Spider mite (Tyrophae Dermacentor taiwanicus, Acaphylla theavagrans, Butterfly mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Alaska mite (Ornithonyssus sylvairum), Nami spider mite (Tetranychu) urticae), Scarlet mite (Erioph
  • termite pests include amphic termites (Reticulitermes miyatakei), American termites (Incisitermes minor), termites (Coptotermes formosanus), termites (Hodotermopsis japonica), camphor termites (Reticulitermes termm ants) ), White termites (Glyptotermes ), Termites termites (Glyptotermes nakajimai), termite termites (Pericapritermes nitobei), and termites termites (Reticulitermes speratus),
  • cockroach Periplaneta fuliginosa
  • German cockroach Blattella germanica
  • Great cockroach Blatta orientalis
  • Greater cockroach Periplaneta brunnea
  • Greater cockroach Blattella lituriplaneta
  • Ponica American cockroach Periplaneta americana
  • Fleas include, for example, human fleas (Pulex irritans), cat fleas (Ctenocephalideselifelis), and chicken fleas (Ceratophyllus gallinae),
  • nematodes for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-breasted nematode (Pratylenchus penetrans), red-footed nematode (Meloidogyne hapla), sweet potato nematode (Meloidogine nematode) Globodera rostochiensis), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), wheat neptune nematode (Pratylenchus neglectus), and semylene nemu
  • molluscs examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Icustabdespect .
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • animal parasitic mites that are one of the targets of the animal parasite control agent of the present invention include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, and Kita ticks (Haemaphysalis).
  • tick mite Haemaphysalis kitaokai
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • Of tick Ixodes persulcatus
  • kingfisher tick Amblyomma testudinarium
  • giant tick Haemaphysalis megaspinosa
  • amino tick Dermacentor reticulatus
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • the animal parasite control agent containing the compound of the present invention is particularly effective for controlling fleas belonging to the family Flea, particularly dog fleas and cat fleas.
  • Examples of ectoparasites which are further controlled by the animal parasite control agent of the present invention include bovine lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine lice (Linognathus vituli), pig lice (ae) suis), lice (Phthirus pubis), and head lice (Pediculus humanus capitis), and lice such as dog lice, blood-sucking dipterous insects, such as catfish (Tabanus trigonus), tiger beetle, Is mentioned.
  • the animal parasite control agent of the present invention is also effective against endoparasites, and examples of such endoparasites include pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms.
  • endoparasites include pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms.
  • Nematodes, crustaceans such as Manson's crested worm, caudate tapeworm, crustacea, multi-headed crustacea, single crested worm, and multi-crusted worms, schistosoma japonicum, and liver Insects such as moths, and protozoa such as coccidium, malaria parasites, intestinal granulocysts, toxoplasmas, and cryptosporidiums.
  • the agricultural and horticultural insecticide containing the phthalamide derivative represented by the general formula (I) of the present invention as an active ingredient is effective against the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, and flower buds. It has a remarkable control effect, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, other crops, flower buds, etc. before or when the occurrence of pests is confirmed, according to the time when the occurrence of pests is expected.
  • the desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds, paddy water, stalks and leaves, or soil and other cultivation carriers.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomato, spinach, broccoli, lettuce, onion, green onion, bell pepper, eggplant, strawberry, pepper, pork etc.), root vegetables (carrots, potatoes, sweet potatoes, sweet potatoes, sweet potatoes, turnips, lotus roots, burdock, garlic etc.), processing crops (Salmon, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), cucumbers (pumpkin, cucumber, watermelon, (Wow, melon,
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • Plants to which tolerance to an acetyl CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation into a plant acetyl-CoA carboxylase, which is introduced into a plant or imparting resistance, and further, chimeric plastic technology (GuraT.
  • Base substitution mutation-introduced nucleic acid typified by “Repairing the Genome's Spelling Mistakes. Science 285: 316-318”
  • Plants resistant to acetyl CoA carboxylase inhibitors and ALS inhibitors can be created by introducing site-specific amino acid substitution mutations into the CoA carboxylase gene and ALS gene.
  • the agricultural and horticultural insecticides of the invention can be used.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
  • ⁇ - such as Cry1Ab, Cry1Ac, Cry1F,
  • Bosome inactivating protein RIP
  • steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3A, etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0374 753, WO 93/07278, WO 95/34656, EP-A-0427 529, EP-A-451878, WO 03. / 052073 and the like.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination or systematized with these techniques.
  • the insecticide for agricultural and horticultural use according to the present invention is used to control various insect pests as they are, or appropriately diluted with water or the like, or suspended in an amount effective for controlling insects or nematodes.
  • pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • they can also be used for application to house building materials, smoke, baits, and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a spraying method for crop foliage stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate.
  • Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • a field crop In a field crop, it can be processed to a seed or a cultivation carrier close to a plant body from sowing to raising seedling.
  • treatment on a plant source of a plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the spraying treatment of the granule to the seedling nursery is preferable.
  • the agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
  • the derivative represented by the general formula (I) of the present invention or a salt thereof is dissolved, separated, suspended by blending them in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio.
  • Appropriate dosage forms such as suspensions, emulsions, liquids, wettable powders, wettable powders, granules, powders, tablets, packs, etc. can be used by turbidity, mixing, impregnation, adsorption or adhesion. It ’s fine.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required.
  • additive components include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.
  • the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • Cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride,
  • amphoteric surfactants such as amino acid type and betaine type. These surfactants may be used alone or in combination of two or more.
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica ( Inorganic fine powders such as fumed silica (white carbon).
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinyl pyrrolidone, fumed silica (fumed silica, white carbon), ester gum, petroleum resin, sodium tripolyphosphate , Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft A copolymer etc. are mentioned.
  • polysaccharides such as starch, alginic acid, mannose, galactose, polyvinyl pyrrolidone, fumed silica (fumed silica, white carbon), este
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
  • the amount of the pest control agent of the present invention is various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application Depending on the location, application time, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.
  • the pesticides of the present invention can be further controlled against other pests, insecticides for agro-horticultural use, acaricides, It can be used by mixing with nematodes, fungicides, biological pesticides, etc., and it can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc. depending on the situation of use.
  • Other agricultural and horticultural insecticides, acaricides, nematicides used for such purposes include, for example:
  • XMC 3,5-xylyl methylcarbamate
  • Bacillus thuringienses aizawai Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid,
  • Examples of agricultural and horticultural fungicides used for the same purpose include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, and acibenzolar-S. -methyl), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam , Isotianil, isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil (imazalil) il), iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, ecromesol echlomezole, edifenphos, etaconazole,
  • herbicides include, for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,3,6-TBA, 2,4,5-T, 2 , 4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4 -CPA, 4-CPA (4-chlorophenoxyacetic acid), 4-CPB, 4-CPP, MCP, MCPA, MCPA-thioethyl, MCPB, MCPB, ioxynil, acronifen, azafenidin ), Acifluorfen, aziprotryne, azimsulfuron, asuram, acetochlor, atrazine, atraton, anisuron, anilofos ), Aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino acid Aropichlor (aminocyclopyr
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CV), insect pox virus (EntomopoXI virus, EPV) ) And other virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
  • microbial pesticide to be used by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • examples of biological pesticides include Encarsia ⁇ ⁇ formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysilis (Dacnusahysticulus) ), Natural enemy organisms such as Amblyseius cucumeris and Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1- Can be used in combination with pheromone such as octadecene It is.
  • Example 1-1 10 g of 1,2-phenylenediamine, 32.7 g of heptafluoro-2-iodopropane, 14.6 g of sodium carbonate and 1 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixture of 100 ml of ethyl acetate and 100 ml of water. Under stirring at room temperature, 16 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C.
  • Example 1-2 4-Heptafluoroisopropyl-1,2-phenylenediamine (2.76 g) was dissolved in 5 ml of trifluoroacetic acid, and the reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, excess trifluoroacetic acid was distilled off under reduced pressure, and the resulting residue was washed with an ether-hexane mixed solvent to give 5-heptafluoroisopropyl-2-trifluoromethyl-1H-benzimidazole 3 0.1 g was obtained. Physical properties: m. p. 132-133 ° C.
  • Example 1-3 Dissolve 2.12 g of 5-heptafluoroisopropyl-2-trifluoromethyl-1H-benzimidazole and 1.38 g of 3-methyl-4-nitrobenzyl bromide in 20 ml of acetonitrile, add 1.25 g of potassium carbonate, and heat to reflux. For 3 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 1-4 1.0 g of 5-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -2-trifluoromethyl-1H-benzimidazole is dissolved in 20 ml of ethanol, 0.53 g of ammonium chloride, 0.56 g of iron powder. And 10 ml of water were added and stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 3-1 2.76 g of 4-heptafluoroisopropyl-1,2-phenylenediamine synthesized according to the production method of Example 1-1 was dissolved in a mixed solution of 10 ml of acetic acid and 3 ml of water, and 0.76 g of sodium nitrite was stirred with ice cooling. Of water was added dropwise. After completion of the dropwise addition, the mixture was heated to 80 ° C. and stirred for 1 hour, ice water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 3-2 1.3 g of 5-heptafluoroisopropyl-1H-benzotriazole and 1.04 g of 3-methyl-4-nitrobenzyl bromide synthesized according to the production method of Example 3-1 were dissolved in 20 ml of acetonitrile, and 0.7 g of potassium carbonate was dissolved. In addition, the reaction was conducted for 3 hours under heating and reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 3-3 0.62 g of 5-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -1H-benzotriazole synthesized according to the production method of Example 3-2 was dissolved in 12 ml of ethanol, 0.37 g of ammonium chloride, 0.38 g of iron powder and 6 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 4-1 2.0 g of 4-heptafluoroisopropyl-2-methylaniline described in JP-A-2001-122836 was dissolved in 8 ml of acetic acid, 0.6 g of sodium nitrite was added, and the reaction was carried out for a whole day and night with stirring at room temperature. After completion of the reaction, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 1.1 g of 5-heptafluoroisopropyl-1H-indazole. Physical properties: m. p. 129-130 ° C.
  • Example 4-2 0.86 g of 5-heptafluoroisopropyl-1H-indazole prepared in Example 4-1 and 0.76 g of 3-methyl-4-nitrobenzyl bromide were dissolved in 20 ml of acetonitrile, added with 0.82 g of potassium carbonate, and heated to reflux. The reaction was carried out for 3 hours below. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 4-3 0.98 g of 5-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -1H-indazole prepared in Example 4-2 was dissolved in 20 ml of ethanol, 0.53 g of ammonium chloride, 0.5% of iron powder. 56 g and 10 ml of water were added and stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 5-1 0.99 g of 5-chloro-1H-indole and 1.50 g of 3-methyl-4-nitrobenzyl bromide were dissolved in 10 ml of DMF, 1.08 g of potassium carbonate was added, and the reaction was performed at 60 ° C. for 3 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 1.5 g of 5-chloro-1- (3-methyl-4-nitrobenzyl) -1H-indole. .
  • Example 5-2 Dissolve 1.2 g of 5-chloro-1- (3-methyl-4-nitrobenzyl) -1H-indole in 20 ml of ethanol, add 1.07 g of ammonium chloride, 1.12 g of iron powder and 10 ml of water, and add 3 ml at room temperature. Stir for hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.1 g of 1- (4-amino-3-methylbenzyl) -5-chloro-1H-indole.
  • Example 5-3 1.1 g of 1- (4-amino-3-methylbenzyl) -5-chloro-1H-indole and 0.6 g of phthalic anhydride were dissolved in 10 ml of acetic acid and reacted for 3 hours under heating and reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with an ether-hexane mixed solvent to give 2- ⁇ 4-[(5-chloro-1H-indol-1-yl) methyl] -2-methyl. 1.6 g of phenyl ⁇ isoindoline-1,3-dione was obtained.
  • Example 5-4 2- ⁇ 4-[(5-chloro-1H-indol-1-yl) methyl] -2-methylphenyl ⁇ isoindoline-1,3-dione 1.6 g, heptafluoro-2-iodopropane 1.4 g, 0.64 g of sodium carbonate and 0.05 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixture of 30 ml of propionitrile and 30 ml of water. While stirring at room temperature, 0.84 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C. and stirred for 1 hour.
  • Example 5-5 2- ⁇ 4-[(5-chloro-3-heptafluoroisopropyl-1H-indol-1-yl) methyl] -2-methylphenyl ⁇ isoindoline-1,3-dione (1.25 g) was dissolved in ethanol (20 ml). Then, 0.33 g of hydrazine hydrate was added, and the reaction was carried out for 3 hours with heating under reflux. After standing to cool, insolubles were removed by filtration, and the solvent was distilled off under reduced pressure.
  • Example 6-1 9.55 g of 2,5-difluoronitrobenzene was dissolved in 60 ml of DMF, and 3.4 g of cyclopropylamine and 12.4 g of potassium carbonate were added. After stirring at 60 ° C. for 3 hours, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 11.0 g of N-cyclopropyl-4-fluoro-2-nitroaniline.
  • Example 6-2 11.0 g of N-cyclopropyl-4-fluoro-2-nitroaniline obtained in Example 6-1 was dissolved in 200 ml of ethanol, 15.0 g of ammonium chloride, 15.6 g of iron powder and 100 ml of water were added, For 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 9.2 g of N 1 -cyclopropyl-4-fluoro-1,2-phenylenediamine.
  • Example 6-3 9.2 g of N 1 -cyclopropyl-4-fluoro-1,2-phenylenediamine obtained in Example 6-2, 20.0 g of heptafluoro-2-iodopropane, 8.7 g of sodium carbonate, and tetrabutyl hydrogen sulfate 0.5 g of ammonium was sequentially added to a mixture of 100 ml of ethyl acetate and 100 ml of water. While stirring at room temperature, 11.5 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the mixture was stirred at room temperature for 1 hour. The organic layer was separated, washed with saturated brine, and dried over magnesium sulfate.
  • Example 6-4 2.6 g of N 1 -cyclopropyl-4-fluoro-5-heptafluoroisopropyl-1,2-phenylenediamine obtained in Example 6-3 was dissolved in 10 ml of THF, and 1,1′-carbonyldiimidazole 2. 5 g was added, and the reaction was carried out for 2 hours under reflux with heating. After completion of the reaction, ice water was added and extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate.
  • Example 6-5 1-Cyclopropyl-5-fluoro-6- (heptafluoroisopropyl) benzimidazolinone 0.72 g and 3-methyl-4-nitrobenzyl bromide 0.55 g obtained in Example 6-4 were dissolved in 10 ml of acetonitrile. Then, 0.41 g of potassium carbonate was added, and the reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 6-6 3-Cyclopropyl-6-fluoro-5-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -2-oxo-2,3-dihydro-1H-benzoate obtained in Example 6-5 0.90 g of imidazole was dissolved in 20 ml of ethanol, 0.53 g of ammonium chloride, 0.56 g of iron powder and 10 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 6-7 (S) -3-Chloro-N 1- ⁇ 4-[(3-cyclopropyl-6-fluoro-5-heptafluoroisopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylthioethyl) phthalamide (compound Nanba8-136) 3-Cyclopropyl-1- (4-amino-3-methylbenzyl) -6-fluoro-5-heptafluoroisopropyl-2-oxo-2,3-dihydro-1H-benzoate obtained in Example 6-6 0.55 g of imidazole and 0.34 g of (S) -4-chloro-3- (1-methyl-2-methylthioethylimino) -3H-isobenzofuran-1-one were dissolved in 5 ml of acetonitrile, and 0.
  • Example 7-1 20.8 g of 4-heptafluoroisopropyl-1,2-phenylenediamine synthesized according to the production method of Example 1-1 was dissolved in 150 ml of THF, 24.5 g of 1,1′-carbonyldiimidazole was added, and the mixture was heated under reflux. The reaction was performed for 2 hours. After completion of the reaction, ice water was added and extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate.
  • Example 7-2 9.4 g of 5- (heptafluoroisopropyl) benzimidazolinone obtained in Example 7-1 was dissolved in 80 ml of DMA, and 1.36 g of 60% sodium hydride was added with stirring at room temperature. After stirring for 1 hour, a solution of 6.78 g of di-t-butyl dicarbonate in 80 ml of DMA was added dropwise. After further stirring for 1 hour, ice water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 7-3 4.1 g of t-butyl 5-heptafluoroisopropyl-2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate obtained in Example 7-2 was dissolved in 50 ml of DMA and stirred at room temperature. 0.44 g of 60% sodium hydride was added. After stirring for 1 hour, 2.34 g of 3-methyl-4-nitrobenzyl bromide was added. After further stirring for 1 hour, ice water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 20 ml of acetonitrile, 15 ml of trifluoroacetic acid was added, and the reaction was carried out for 2 hours under reflux with heating. After completion of the reaction, the solvent was distilled off under reduced pressure, ice water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 7-4 Dissolve 0.9 g of 6-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -2-oxo-2,3-dihydro-1H-benzimidazole obtained in Example 7-3 in 10 ml of acetonitrile. Then, 0.32 g of dimethylcarbamoyl chloride and 0.69 g of potassium carbonate were added, and the reaction was carried out for 3 hours while heating under reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 7-5 0.90 g of 1-dimethylcarbamoyl-5-heptafluoroisopropyl-3- (3-methyl-4-nitrobenzyl) -2-oxo-2,3-dihydro-1H-benzimidazole obtained in Example 7-4 was dissolved in 20 ml of ethanol, 0.46 g of ammonium chloride, 0.48 g of iron powder and 10 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 7-6 (S) -3-Chloro-N 1- ⁇ 4-[(3-dimethylcarbamoyl-6-heptafluoroisopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl) methyl] -2 - methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylthioethyl) phthalamide (compound Nanba8-266) 0.5 g of 3- (4-amino-3-methylbenzyl) -1-dimethylcarbamoyl-6-heptafluoroisopropyl-2-oxo-2,3-dihydro-1H-benzimidazole obtained in Example 7-5 And (S) -4-chloro-3- (1-methyl-2-methylthioethylimino) -3H-isobenzofuran-1-one (0.32 g) are dissolved in 3 ml of acetonitrile, and 0.01 g of
  • Example 8-1 6.0 g of 2-aminophenol, 19.5 g of heptafluoro-2-iodopropane, 9.2 g of sodium carbonate and 0.5 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixed solution of 50 ml of ethyl acetate and 50 ml of water. While stirring at room temperature, 11.5 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C. and stirred for 1 hour. The organic layer was separated, washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over magnesium sulfate.
  • Example 8-2 1.66 g of 5-heptafluoroisopropyl-2-aminophenol obtained in Example 8-1 was dissolved in 20 ml of acetonitrile, 0.72 g of ethyl chlorocarbonate and 0.5 g of potassium carbonate were added, and the mixture was heated under reflux for 3 hours. Reaction was performed. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 1.5 g of 6-heptafluoroisopropyl-2-benzoxazolinone. Physical properties: m. p. 152-153 ° C.
  • Example 8-3 0.85 g of 6-heptafluoroisopropyl-2-benzoxazolinone obtained in Example 8-2 and 0.57 g of 2-methyl-3-nitrobenzyl chloride were dissolved in 20 ml of acetonitrile, and 0.58 g of potassium carbonate was dissolved. In addition, the reaction was conducted for 3 hours under heating and reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 8-4 0.90 g of 6-heptafluoroisopropyl-3- (2-methyl-3-nitrobenzyl) -2-benzoxazolinone obtained in Example 8-3 was dissolved in 20 ml of ethanol, 0.56 g of ammonium chloride, Iron powder 0.53g and water 10ml were added, and it stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 9-1 A reaction of 1.40 g of 2-fluoro-4- (heptafluoroisopropyl) aniline and 1.92 g of potassium isopropylxanthate was carried out in 10 ml of DMF at 100 ° C. for 3 hours. After completion of the reaction, 1N aqueous hydrochloric acid was added to acidify the solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with an ether-hexane mixed solvent to obtain 1.5 g of 6-heptafluoroisopropyl-2-mercaptobenzothiazole. Physical properties: m. p. 126-128 ° C.
  • Example 9-2 0.70 g of 6-heptafluoroisopropyl-2-mercaptobenzothiazole obtained in Example 9-1 and 0.22 g of potassium hydroxide were dissolved in 5 ml of water, and 0.70 g of 35% hydrogen peroxide solution was added. The reaction was carried out at 3 ° C. for 3 hours. After completion of the reaction, 1N aqueous hydrochloric acid was added to acidify the solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 9-3 0.32 g of 6-heptafluoroisopropyl-2-benzothiazolinone obtained in Example 9-2 and 0.25 g of 3-methyl-4-nitrobenzyl bromide were dissolved in 10 ml of acetonitrile, and 0.21 g of potassium carbonate was dissolved. In addition, the reaction was performed for 3 hours under heating and reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 9-4 0.37 g of 6-heptafluoroisopropyl-3- (3-methyl-4-nitrobenzyl) -2-benzothiazolinone obtained in Example 9-3 was dissolved in 15 ml of ethanol, 0.21 g of ammonium chloride, 0.22 g of iron powder and 8 ml of water were added and stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 10-1 Methyl 2-chloromethyl-4-heptafluoroisopropylphenyl carbamate (1.8 g) was dissolved in ethanol (40 ml), 2-methoxyethylamine (0.72 g) was added, and the reaction was carried out with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the resulting residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 10-2 0.95 g of 3- (2-methoxyethyl) -6-heptafluoroisopropyl-3,4-dihydro-1H-quinazolin-2-one obtained in Example 10-1 was dissolved in 3 ml of monochlorobenzene to obtain 60% Sodium hydride 0.07g and DMA 0.26g were added, and it stirred at room temperature for 30 minutes. 0.64 g of 3-methyl-4-nitrobenzyl bromide was added, and the mixture was further stirred at room temperature for 3 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 10-3 6-Heptafluoroisopropyl-3- (2-methoxyethyl) -1- (3-methyl-4-nitrobenzyl) -3,4-dihydro-1H-quinazolin-2-one obtained in Example 10-2 0.81 g was dissolved in 20 ml of ethanol, 0.42 g of ammonium chloride, 0.43 g of iron powder and 10 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 10-4 (S) -3-Chloro-N 1- (4- ⁇ [6-heptafluoroisopropyl-3- (2-methoxyethyl) -2-oxo-3,4-dihydro-2H-quinazolin-1-yl] methyl ⁇ -2-methylphenyl) -N 2 - (1-methyl-2-methylsulfinyl-ethyl) phthalamide (compound Nanba18-98) and (S)-3-chloro -N 1 - (4- ⁇ [6- heptafluoro-isopropyl-3- (2-methoxyethyl) -2-oxo-3,4-dihydro -2H- quinazolin-1-yl] methyl ⁇ -2-methylphenyl) -N 2 - (1-methyl-2- Synthesis of methylsulfonylethyl) phthalamide (Compound No.
  • Example 11-1 1.67 g of 2-nitrobenzoic acid was dissolved in 10 ml of toluene, 0.01 g of DMF was added, and 1.19 g of thionyl chloride was added dropwise under ice cooling. After heating under reflux for 1 hour, the solvent was distilled off under reduced pressure. The obtained acid chloride was dissolved in 5 ml of THF and added dropwise to 5 ml of 2M-methylamine THF solution and 2.02 g of triethylamine in 10 ml of THF under ice-cooling and stirring. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes, water was added, and the mixture was extracted with ethyl acetate.
  • Example 11-3 0.69 g of 2-amino-N-methylbenzamide obtained in Example 11-2, 1.64 g of heptafluoro-2-iodopropane, 0.73 g of sodium carbonate and 0.05 g of tetrabutylammonium hydrogen sulfate were added to ethyl acetate. Sequentially added to a mixture of 5 ml and 5 ml of water. While stirring at room temperature, 1.6 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C. and stirred for 1 hour. The organic layer was separated, washed with saturated brine, and dried over magnesium sulfate.
  • Example 11-4 0.89 g of 2-amino-5-heptafluoroisopropyl-N-methylbenzamide obtained in Example 11-3 was dissolved in 6 ml of THF, 1.4 g of 1,1′-carbonyldiimidazole was added, and the mixture was heated under reflux. The reaction was performed for 2 hours. After completion of the reaction, ice water was added and extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate.
  • Example 11-5 0.63 g of 6-heptafluoroisopropyl-3-methyl-1H, 3H-quinazoline-2,4-dione obtained in Example 11-4 and 0.44 g of 3-methyl-4-nitrobenzyl bromide were added to 15 ml of acetonitrile. It melt
  • Example 11-6 0.74 g of 6-heptafluoroisopropyl-3-methyl-1- (3-methyl-4-nitrobenzyl) -1H, 3H-quinazoline-2,4-dione obtained in Example 11-5 was added to 5 ml of ethanol. After dissolution, 0.41 g of ammonium chloride, 0.42 g of iron powder and 3 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 11-7 (S) -3-Chloro-N 1- ⁇ 4-[(2,4-dioxo-6-heptafluoroisopropyl-3-methyl-3,4-dihydro-2H-quinazolin-1-yl) methyl] -2 - methylphenyl ⁇ -N 2 - (1-methyl-2-methylsulfinyl-ethyl) phthalamide (compound Nanba18-177) and (S)-3-chloro -N 1 - ⁇ 4 - [( 2,4- dioxo 6-heptafluoro-isopropyl-3-methyl-3,4-dihydro -2H- quinazolin-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - (1-methyl-2-methylsulfonyl-ethyl) phthalamide ( Synthesis of Compound No.
  • Example 11-6 1- (4-Amino-3-methylbenzyl) -3-methyl-6-heptafluoroisopropyl-1H, 3H-quinazoline-2,4-dione obtained in 1) and (S) -4-chloro- 0.19 g of 3- (1-methyl-2-methylthioethylimino) -3H-isobenzofuran-1-one was dissolved in 3 ml of acetonitrile, 0.01 g of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 3 hours.
  • Example 12-1 13.6 g of 2-aminobenzamide, 24.1 g of heptafluoro-2-iodopropane, 15.9 g of sodium carbonate and 0.8 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixture of 100 ml of ethyl acetate and 100 ml of water. While stirring at room temperature, 17.4 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C. and stirred for 1 hour. The organic layer was separated, washed with saturated brine, and dried over magnesium sulfate.
  • Example 12-2 5.7 g of 2-amino-5-heptafluoroisopropylbenzamide obtained in Example 12-1 was dissolved in 20 ml of THF, 8.7 g of 1,1′-carbonyldiimidazole was added, and the reaction was allowed to proceed for 2 hours with heating under reflux. went. After completion of the reaction, ice water was added and extracted with ethyl acetate. The organic layer was washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate.
  • Example 12-4 6-Heptafluoroisopropyl-3- (3-methyl-4-nitrobenzyl) -1H, 3H-quinazoline-2,4-dione 0.71 g obtained in Example 12-3 was dissolved in 4 ml of DMA, and 60% Sodium hydride 0.06g was added and it stirred at room temperature for 30 minutes. 0.21 g of methyl iodide was added and the mixture was further stirred at room temperature for 3 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 12-5 6.13 g of 6-heptafluoroisopropyl-1-methyl-3- (3-methyl-4-nitrobenzyl) -1H, 3H-quinazoline-2,4-dione obtained in Example 12-4 was added to 4 ml of ethanol. After dissolution, 0.37 g of ammonium chloride, 0.38 g of iron powder and 2 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 12-6 (S) -3-Chloro-N 1- ⁇ 4-[(2,4-dioxo-6-heptafluoroisopropyl-1-methyl-1,2-dihydro-4H-quinazolin-3-yl) methyl] -2 - methylphenyl ⁇ -N 2 - (1-methyl-2-methylsulfinyl-ethyl) phthalamide (compound Nanba19-8) and (S)-3-chloro -N 1 - ⁇ 4 - [( 2,4- dioxo 6-heptafluoro-isopropyl-1-methyl-1,2-dihydro -4H- quinazolin-3-yl) methyl] -2-methylphenyl ⁇ -N 2 - (1-methyl-2-methylsulfonyl-ethyl) phthalamide ( Synthesis of Compound No.
  • Example 13-1 24.7 g of anthranilic acid, 60 g of heptafluoro-2-iodopropane, 55.3 g of sodium carbonate and 2 g of tetrabutylammonium hydrogen sulfate were sequentially added to a mixture of 200 ml of ethyl acetate and 200 ml of water. While stirring, the internal temperature was kept at 40 ° C., and 34.8 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the mixture was further stirred for 1 hour. The organic layer was separated, washed successively with 1N aqueous hydrochloric acid and saturated brine, and dried over magnesium sulfate.
  • Example 13-2 0.92 g of 5-heptafluoroisopropyl anthranilic acid obtained in Example 13-1 was dissolved in 2 ml of trifluoroacetic anhydride and reacted for 1 hour under heating to reflux. After completion of the reaction, the mixture was concentrated to dryness under reduced pressure, and the resulting residue was dissolved in 10 ml of xylene. 0.5 g of 3-methyl-4-nitrobenzylamine was added, and the reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 13-3 0.85 g of 6-heptafluoroisopropyl-3- (3-methyl-4-nitrobenzyl) -2-trifluoromethyl-3H-quinazolin-4-one obtained in Example 13-2 was dissolved in 10 ml of ethanol. Then, 0.41 g of ammonium chloride, 0.42 g of iron powder and 5 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 13-4 (S) -3-Chloro-N 1- ⁇ 4-[(6-heptafluoroisopropyl-4-oxo-2-trifluoromethyl-4H-quinazolin-3-yl) methyl] -2-methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylthioethyl) phthalamide (compound Nanba23-10) 0.50 g of crude 3- (4-amino-3-methylbenzyl) -6-heptafluoroisopropyl-2-trifluoromethyl-3H-quinazolin-4-one obtained in Example 13-3 and (S) 0.27 g of -4-chloro-3- (1-methyl-2-methylthioethylimino) -3H-isobenzofuran-1-one is dissolved in 5 ml of acetonitrile, 0.01 g of trifluoroacetic acid is added, and 3 hours at room temperature.
  • Example 14-1 6.26 g of 2-aminothiophenol and 6.07 g of triethylamine were dissolved in 50 ml of THF, and 9.75 g of bromoacetate-t-butyl was added with stirring at room temperature. The mixture was further stirred at room temperature for 1 hour, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 12.0 g of 2-aminophenylthioacetic acid-t-butyl.
  • Example 14-2 11.97 g of 2- (2-aminophenyl) thioacetic acid-t-butyl obtained in Example 14-1, 17.76 g of heptafluoro-2-iodopropane, 7.95 g of sodium carbonate, and tetrabutylammonium hydrogen sulfate 0 0.5 g was sequentially added to a mixture of 100 ml of ethyl acetate and 100 ml of water. Under stirring, the internal temperature was kept at 40 ° C., and 10.45 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the mixture was further stirred for 1 hour.
  • Example 14-3 1.42 g of [2-amino-5- (heptafluoroisopropyl) phenyl] thioacetic acid-t-butyl obtained in Example 14-2 was dissolved in 5 ml of 4N hydrogen chloride-ethyl acetate solution, and heated under reflux. The reaction was carried out for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in 10 ml of THF, and 1.1 g of triethylamine and 1.8 g of 2-chloro-1-methylpyridinium iodide were added. After stirring at room temperature for 3 hours, water was added and the mixture was extracted with ethyl acetate.
  • Example 14-4 0.67 g of 7-heptafluoroisopropyl-2H-benzo [1,4] thiazin-3-one obtained in Example 14-3 and 0.51 g of 3-methyl-4-nitrobenzyl bromide were dissolved in 20 ml of acetonitrile. Then, 0.42 g of potassium carbonate was added, and the reaction was carried out under reflux with heating for 3 hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 14-5 7-Heptafluoroisopropyl-3- (3-methyl-4-nitrobenzyl) -2H-benzo [1,4] thiazin-3-one 0.82 g obtained in Example 14-4 was dissolved in 10 ml of ethanol. Then, 0.45 g of ammonium chloride, 0.48 g of iron powder and 5 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 14-6 (S) -3-Chloro-N 1- ⁇ 4-[(7-heptafluoroisopropyl-3-oxo-2H-benzo [1,4] thiazin-4-yl) methyl] -2-methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylthioethyl) phthalamide (compound Nanba26-10) 3- (4-Amino-3-methylbenzyl) -7-heptafluoroisopropyl-2H-benzo [1,4] thiazin-3-one 0.36 g and (S) -4 obtained in Example 14-5 -Chloro-3- (1-methyl-2-methylthioethylimino) -3H-isobenzofuran-1-one (0.27 g) was dissolved in 3 ml of acetonitrile, 0.01 g of trifluoroacetic acid was added, and the mixture was stirred at room temperature for 3 hours.
  • Example 15-1 4-Heptafluoroisopropyl-1,2-phenylenediamine (1.38 g) was dissolved in xylene (5 ml), ethyl trifluoropyruvate (0.85 g) was added, and the reaction was carried out for 3 hours with heating under reflux.
  • Example 15-2 Using 0.38 g of 6-heptafluoroisopropyl-2-oxo-3-trifluoromethyl-1H-quinoxalin-2-one and 0.23 g of 3-methyl-4-nitrobenzyl bromide obtained in Example 15-1 in acetonitrile It melt
  • Example 15-3 Using 0.27 g of 6-heptafluoroisopropyl-1- (3-methyl-4-nitrobenzyl) -2-oxo-3-trifluoromethyl-1H-quinoxalin-2-one obtained in Example 15-2 in ethanol It melt
  • Example 15-4 (S) -3-Chloro-N 1- ⁇ 4-[(6-heptafluoroisopropyl-2-oxo-3-trifluoromethyl-2H-quinoxalin-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - (1-methyl-2-methylthioethyl) phthalamide (compound Nanba28-13) and (S) -3-chloro -N 1 - ⁇ 4 - [( 7- heptafluoroisopropyl-2-oxo-3- trifluoromethyl -2H- quinoxalin-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylthioethyl) phthalamide (compound Nanba28-16) Crude product of 1- (4-amino-3-methylbenzyl) -6-heptafluoroisopropyl-2-oxo-3-trifluoromethyl-1H-quinoxalin
  • Example 16-1 3.9 g of N-methyl-1,2-phenylenediamine dihydrochloride, 7.1 g of heptafluoro-2-iodopropane, 6.36 g of sodium carbonate and 0.2 g of tetrabutylammonium hydrogen sulfate, 20 ml of ethyl acetate and 20 ml of water To the mixture. While stirring at room temperature, 3.56 g of sodium dithionite was added in small portions over 30 minutes. After completion of the addition, the temperature was raised to 40 ° C. and stirred for 1 hour. The organic layer was separated, washed with saturated brine, and dried over magnesium sulfate.
  • Example 16-2 2.00 g of a mixture of N 1 -methyl-4-heptafluoroisopropyl-1,2-phenylenediamine and N 1 -methyl-5-heptafluoroisopropyl-1,2-phenylenediamine obtained in Example 16-1 It melt
  • Example 16-3 1- [2-Amino-4- (heptafluoroisopropyl) phenyl] -3-ethyl-1-methylurea and 1- [2-amino-5- (heptafluoroisopropyl) phenyl] obtained in Example 16-2 2.03 g of a mixture of -3-ethyl-1-methylurea and 1.7 g of triethylamine were dissolved in 10 ml of THF, 1.66 g of triphosgene was added, and the reaction was carried out for 2 hours while stirring at room temperature. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 16-4 3-ethyl-7-heptafluoroisopropyl-1-methyl-1H, 3H, 5H-benzo [1,3,5] triazepine-2,4-dione obtained in Example 16-3, 1.24 g and 3- 0.74 g of methyl-4-nitrobenzyl bromide was dissolved in 15 ml of acetonitrile, 1.32 g of potassium carbonate was added, and the reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 16-5 3-ethyl-8-heptafluoroisopropyl-5-methyl-5- (3-methyl-4-nitrobenzyl) -1H, 3H, 5H-benzo [1,3,5] obtained in Example 16-4 1.07 g of triazepine-2,4-dione was dissolved in 20 ml of ethanol, 0.54 g of ammonium chloride, 0.56 g of iron powder and 10 ml of water were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, insoluble material was removed using celite, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.
  • Example 16-6 (S) -3-Chloro-N 1- ⁇ 4-[(2,4-dioxo-3-ethyl-8-heptafluoroisopropyl-5-methyl-2,3,4,5-tetrahydro-1H-benzo [ 1,3,5] triazepine-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - (1-methyl-2-methylsulfinyl-ethyl) phthalamide (compound Nanba31-8) and (S) -3 -Chloro-N 1- ⁇ 4-[(2,4-dioxo-3-ethyl-8-heptafluoroisopropyl-5-methyl-2,3,4,5-tetrahydro-1H-benzo [1,3,5 ] triazepine-1-yl) methyl] -2-methylphenyl ⁇ -N 2 - synthesis of (1-methyl-2-methylsulfonyl-ethyl) phthalamide (compound Nanba
  • Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
  • Test Example 1 Test for insecticide test on Frankliniella occidentalis The kidney leaf fixed on the agar medium was inoculated with female adults of orange thrips and allowed to lay eggs for one day. Further, after 3 days, hatching larvae on the leaf pieces were counted, and then a chemical solution diluted with 500 ppm of a drug containing the compounds shown in Tables 1 to 19, 21, 21, and 23 to 31 as an active ingredient was sprayed. did. The number of larvae of this species that survived 4 days after the treatment was investigated, the mortality rate was calculated by the following formula, and the following criteria were used. Two consecutive systems.
  • Test Example 2 Insecticidal test against Plutella xylostella Spikelet seedlings were released from adult adults of spider moths and laid, and two days after release, Chinese cabbage seedlings with spawning eggs were shown in Tables 1 to 19, Tables 21 and 23. Tables 31 to 31 were immersed for about 30 seconds in a chemical solution diluted with 50 ppm of a drug containing the compound as an active ingredient, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C. The number of hatching insects was investigated 6 days after immersion in the chemical solution, the death rate was calculated by the following formula, and the determination was performed according to the following criteria. 1 zone, 10 heads, 3 units.
  • Test Example 3 Insecticidal test against Spodoptera litura Cabbage leaf pieces (variety: seasonal harvest) in a solution obtained by diluting the drug containing the compounds shown in Tables 1 to 19, 21 and 23 to 31 to 500 ppm. ) was soaked for about 30 seconds, air-dried, placed in a plastic petri dish with a diameter of 9 cm, inoculated with second-instar larvae, capped, and allowed to stand in a thermostatic chamber at 25 ° C. The number of live and dead insects was investigated 8 days after the inoculation, and the death rate was calculated according to the following formula. 1 zone, 10 heads, 3 units.
  • Test Example 4 Insecticidal test against Adoxophyes sp. Adhesive leaves of chemicals containing the compounds listed in Tables 1 to 19, 21, 21, and 23 to 31 diluted to 500 ppm as an active ingredient. It was immersed for about 30 seconds, air-dried, placed in a plastic petri dish with a diameter of 9 cm, inoculated with chinook leafworm larvae, and then allowed to stand in a temperature-controlled room at 25 ° C. and 70% humidity. The number of live and dead insects was investigated 8 days after the inoculation, and the determination was made in the same manner as in Test Example 3. 1 zone, 10 heads, 3 units.
  • Test Example 5 Control test against peach aphid ( Myzus persicae ) Chinese cabbage aphid larvae were inoculated by planting Chinese cabbage in a plastic pot with a diameter of 8 cm and a height of 8 cm. The next day, the chemicals (500 ppm) containing the compounds listed in Tables 1 to 19, 21 and 23 to 31 as active ingredients are sprayed on the stems and leaves of potted Chinese cabbage and air-dried. The number of parasites of the peach aphid parasitizing each Chinese cabbage on the sixth day after spraying the drug was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
  • Ta Number of parasites before spraying in the treated zone
  • Ca Number of parasites before spraying in the untreated zone
  • C Criteria for determining the number of parasites after spraying in the untreated zone.
PCT/JP2012/078143 2011-11-02 2012-10-31 フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法 WO2013065725A1 (ja)

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WO2014178363A1 (ja) * 2013-04-30 2014-11-06 日本農薬株式会社 ジアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法
WO2014183415A1 (zh) * 2013-05-17 2014-11-20 南开大学 具有光学活性和几何异构的双酰胺衍生物与制备及应用
WO2015169999A1 (en) 2014-05-09 2015-11-12 Orion Corporation Pharmacologically active quinazolinedione derivatives
US9255108B2 (en) 2012-04-10 2016-02-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9359365B2 (en) 2013-10-04 2016-06-07 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9708348B2 (en) 2014-10-03 2017-07-18 Infinity Pharmaceuticals, Inc. Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
US9751888B2 (en) 2013-10-04 2017-09-05 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9775844B2 (en) 2014-03-19 2017-10-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10160761B2 (en) 2015-09-14 2018-12-25 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
US10759806B2 (en) 2016-03-17 2020-09-01 Infinity Pharmaceuticals, Inc. Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors
US10919914B2 (en) 2016-06-08 2021-02-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
CN115536597A (zh) * 2022-09-29 2022-12-30 山东新华制药股份有限公司 一种高纯苯甲酸阿格列汀中间体的制备方法

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CN111971283B (zh) * 2018-03-26 2023-04-14 肿瘤研究所基金会 具有增强的抗肿瘤作用的新型化合物
CN110294719B (zh) * 2019-07-15 2023-02-28 五邑大学 一种噻唑烷酮化合物的合成方法
CN115583922B (zh) * 2022-10-17 2023-09-19 黄山学院 含氟n-(3-(苯并噁唑-2-基)苯基)酰胺类化合物及其制备方法和应用

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US9255108B2 (en) 2012-04-10 2016-02-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
WO2014178363A1 (ja) * 2013-04-30 2014-11-06 日本農薬株式会社 ジアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法
WO2014183415A1 (zh) * 2013-05-17 2014-11-20 南开大学 具有光学活性和几何异构的双酰胺衍生物与制备及应用
US10329299B2 (en) 2013-10-04 2019-06-25 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9359365B2 (en) 2013-10-04 2016-06-07 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9751888B2 (en) 2013-10-04 2017-09-05 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9828377B2 (en) 2013-10-04 2017-11-28 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US11541059B2 (en) 2014-03-19 2023-01-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9775844B2 (en) 2014-03-19 2017-10-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10675286B2 (en) 2014-03-19 2020-06-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
WO2015169999A1 (en) 2014-05-09 2015-11-12 Orion Corporation Pharmacologically active quinazolinedione derivatives
US10253047B2 (en) 2014-10-03 2019-04-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10941162B2 (en) 2014-10-03 2021-03-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9708348B2 (en) 2014-10-03 2017-07-18 Infinity Pharmaceuticals, Inc. Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
US10160761B2 (en) 2015-09-14 2018-12-25 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
US11247995B2 (en) 2015-09-14 2022-02-15 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
US11939333B2 (en) 2015-09-14 2024-03-26 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
US10759806B2 (en) 2016-03-17 2020-09-01 Infinity Pharmaceuticals, Inc. Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors
US10919914B2 (en) 2016-06-08 2021-02-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
CN115536597A (zh) * 2022-09-29 2022-12-30 山东新华制药股份有限公司 一种高纯苯甲酸阿格列汀中间体的制备方法

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