WO2012176856A2 - Pesticide - Google Patents

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Publication number
WO2012176856A2
WO2012176856A2 PCT/JP2012/065928 JP2012065928W WO2012176856A2 WO 2012176856 A2 WO2012176856 A2 WO 2012176856A2 JP 2012065928 W JP2012065928 W JP 2012065928W WO 2012176856 A2 WO2012176856 A2 WO 2012176856A2
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WO
WIPO (PCT)
Prior art keywords
compound
atom
formula
salt
alkyi
Prior art date
Application number
PCT/JP2012/065928
Other languages
French (fr)
Other versions
WO2012176856A3 (en
Inventor
Kenichi Nakamoto
Masakazu SERIZAWA
Yuko Nishihama
Tatsuya Kani
Tatsuya Shimada
Original Assignee
Ishihara Sangyo Kaisha, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha, Ltd. filed Critical Ishihara Sangyo Kaisha, Ltd.
Publication of WO2012176856A2 publication Critical patent/WO2012176856A2/en
Publication of WO2012176856A3 publication Critical patent/WO2012176856A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/14—Ethers
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
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    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
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    • A—HUMAN NECESSITIES
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    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
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    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • 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
    • A01N43/72—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
    • A01N43/80—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 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—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 three ring hetero atoms
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids

Definitions

  • the present invention relates to a pesticide containing, as an active ingredient, the after-described novel compound represented by the formula (I) or its salt, i.e. a 3- arylphenyl sulfide derivative or its salt.
  • Patent Document 1 discloses a 3-arylphenyl sulfide derivative useful as an insecticide or miticide. However, the compound of the formula (I) or its salt is not disclosed.
  • Patent Document 2 discloses a (3-sulfur atom-substituted phenyl) heteroaryl derivative useful as an insecticide or miticide. However, the compound of the formula (I) or its salt is not disclosed.
  • Patent Document 1 WO99/55668
  • Patent Document 2 JP-A-2008-308448
  • the present inventors have conducted various studies on 3-arylphenyl sulfide derivatives in an effort to find a superior pesticide. As a result, they have found that the after-described novel compound of the formula (I) or its salt has a very high controlling effect against pests at a low dose and at the same time has safety to crop plants or mammals, and have accomplished the present invention.
  • the present invention provides the following (1) to (16).
  • each of R 1 and R 2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyi, haloalkyi, alkoxy, haloalkoxy or cyano;
  • R 3 is alkyi or haloalkyi;
  • n is an integer of 0 or 1 ; and
  • Q is any of the following formulae [Q-1] to [Q-6]:
  • each of A 1 to A 8 which may be the same or different from one another is CH or a nitrogen atom, provided that when any of A 1 to A 8 is CH, it may be substituted by R 4 , and among A 1 to A 8 , the number of groups which may be nitrogen atoms, is from 0 to 3; each of B 1 to B 4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of B 1 to B 4 is CH, it may be substituted by R 4 , and among B 1 to B 4 , the number of groups which may be nitrogen atoms, is from 0 to 1 ; each of B 5 to B 7 which may be the same or different from one another, is C(R 5 )(R 6 ), an oxygen atom, a sulfur atom, SO or S0 2 ; each of E 1 to E 4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of E 1 to E 4 is CH, it may be substituted by R 4 ,
  • each of J 1 to J 6 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of J 1 to J 6 is CH, it may be substituted by R 4 , and among J 1 to J 6 , the number of groups which may be nitrogen atoms, is from 0 to 2; each of L 1 to L 5 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of L 1 to L 5 is CH, it may be substituted by R 4 , and among L 1 to L 5 , the number of groups which may be nitrogen atoms, is from 0 to 2;
  • L 6 is an oxygen atom or a sulfur atom;
  • R 4 is a halogen atom, alkyl, haloalkyi, alkoxy, haloalkoxy
  • R 1 is a hydrogen atom, a halogen atom, alkyl or alkoxy
  • R 2 is a hydrogen atom, a halogen atom, alkyl or alkoxy
  • R 3 is alkyl or haloalkyl
  • Q is the formula [Q-1], [Q-2] or [Q-4].
  • R 1 is a hydrogen atom, a halogen atom, alkyl or alkoxy
  • R 2 is a hydrogen atom, a halogen atom, alkyl or alkoxy
  • R 3 is alkyl or haloalkyl
  • Q is the formula [Q-1] or [Q-2].
  • X is a bromine atom, -B(OH) 2 or pinacolatoboranyl
  • n is an integer of 0 or 1
  • each of R and R 2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano
  • R 3 is alkyl or haloalkyl, provided that a case wherein R 1 is a hydrogen atom or a fluorine atom, R 2 is methyl, and R 3 is trifluoroethyl, is excluded.
  • a method for controlling pests which comprises applying an effective amount of the compound or its salt as defined in the above (1 ) thereto.
  • a method for controlling insects, mites, nematodes or soil pests which comprises applying an effective amount of the compound or its salt as defined in the above (1 ) thereto.
  • a method for controlling insects or mites which comprises applying an effective amount of the compound or its salt as defined in the above (1) thereto.
  • a pesticide containing the above compound of the formula (I) or its salt as an active ingredient has a very high controlling effect against pests at a low dose and at the same time has safety to crop plants or mammals.
  • halogen atom in the formula (I) or the halogen atom as a substituent an atom of fluorine, chlorine, bromine or iodine may be mentioned.
  • the number of the halogen atoms as the substituents may be 1 or more, and if more, the respective halogen atoms may be the same or different. Further, the positions for substitution with such halogen atoms may be any positions.
  • the alkyl or alkyl moiety in the formula (I) may be linear or branched.
  • Ci-6 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- butyl, tert-butyl, pentyl or hexyl may be mentioned.
  • the pyridyl which may be substituted with R 11 in the formula (I) may, for example, be 2-pyridyl, 3-pyridyl or 4-pyridyl.
  • the number of substituents is from 1 to 4. Further, when it is substituted with a plurality of
  • R 11 the plurality of R 1 may be the same or different.
  • the number of substituents is from 1 to 5. Further, when it is substituted with a plurality of R 11 , the plurality of R 11 may be the same or different.
  • the salt of the compound of the above formula (I) includes all kinds so long as they are acceptable in this technical field.
  • an ammonium salt such as a dimethyl ammonium salt or a triethyl ammonium salt
  • an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate
  • an organic acid salt such as an acetate or a methane sulfonate
  • the compound of the above formula (I) may have isomers such as optical isomers, and such isomers and mixtures thereof are both included in the present invention.
  • isomers are in the form of a mixture, unless otherwise specified.
  • various isomers other than those mentioned above may be included within the scope of the common knowledge in this technical field.
  • it may have a chemical structure different from the above formula (I), but for those skilled in the art, it can sufficiently be recognized that it is in an isomeric relationship and falls within the scope of the present invention.
  • the compound of the above formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) and its raw material compound can be produced by the following processes [1 ] and [2] and in accordance with a usual process for producing a salt.
  • the present invention is by no means limited to such processes.
  • the above formula (II) representing an intermediate for the production of the compound of the formula (I) or its salt is constituted by the formula (ll-a), and the formula (ll-b). ESS [1]
  • Route A in the process [1] can be carried out by reacting the compound of the formula (III) and the compound of the formula (ll-a) in the presence of a base and a transition metal catalyst in a solvent.
  • Route B in the process [1] can be carried out by reacting the compound of the formula (IV) and a compound of the formula (ll-b) in the presence of a base and a transition metal catalyst in a solvent.
  • the compounds of the formulae (ll-a) and (ll-b) include novel compounds and can be produced by a method disclosed in
  • the compound of the formula (IV) may be a known compound or may be produced by reacting the corresponding magnesium reagent or lithium reagent with trimethyl borate.
  • the transition metal catalyst may suitably be selected for use from e.g. a palladium compound such as palladium-activated carbon, palladium acetate, dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium or tris(dibenzalacetone)palladium; and a nickel compound such as
  • the transition metal catalyst may be used in an amount of from 0.001 to 1 time by mol, preferably from 0.01 to 0.1 time by mol, to the compound of the formula (III) or the formula (ll-b).
  • one or more may suitably be selected for use from e.g. an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkaline earth metal hydroxide such as calcium hydroxide or magnesium hydroxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; an alkali metal acetate such as sodium acetate or potassium acetate; a metal hydride such as sodium hydride or potassium hydride; a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium tert-butoxide; and an organic base such as triethylamine, ⁇ , ⁇ -dimethylaniline, pyridine, 4-N,N-dimethylamino pyridine or 1 ,8- diazabicyclo[5.4.0]-7-undecene.
  • an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide
  • the base may be used in an amount of from 1 to 5 times by mol, preferably from 1.5 to 3 times by mol, to the compound of the formula (III) or (ll-b).
  • the solvent may be any solvent so long as it is inert to the reaction.
  • one or more may suitably be selected for use from e.g.
  • an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or dimethoxy ethane
  • an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene
  • an aprotic polar solvent such as ⁇ , ⁇ -dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methyl-2- pyrolidone, dimethylsulfoxide or sulforane
  • a nitrile such as acetonitrile or propionitrile
  • an ester such as ethyl acetate or ethyl propionate
  • an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane
  • a protonic solvent such as water, methanol or ethanol.
  • the reaction temperature is usually from -50 to 200°C, preferably from 20 to
  • the reaction time is usually from 0.5 to 48 hours, preferably from 1 to 24 hours.
  • the oxidizing agent may suitably be selected for use from e.g. an aqueous hydrogen peroxide solution, m-chloroperbenzoic acid, perbenzoic acid, sodium periodide, OXONE (tradename of E.I. du Pont; containing potassium hydrogen peroxosulfate), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite and sodium hypochlorite.
  • the oxidizing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (l-a).
  • This reaction may be carried out, if necessary, in the presence of a catalyst.
  • the catalyst may be selected for use from e.g. sodium tungstate and flavin.
  • the catalyst may be used in an amount of from 0.0001 to 1 time by mol, preferably from 0.001 to 0.05 time by mol, to the compound of the formula (l-a).
  • the solvent may be any solvent so long as it is inert to the reaction.
  • one or more may suitably be selected for use from e.g. a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; an ester such as ethyl acetate or ethyl propionate; and acetic acid.
  • the reaction temperature is usually from -50 to 150°C, preferably from 0 to 50°C.
  • the reaction time is usually from 0.5 to 48 hours, preferably from 1 to 30 hours.
  • a compound of the formula (ll-b-1) may be produced, for example, by the reactions of the following (1) to (4).
  • the first stage can be carried out in the presence of a halosulfonylation agent.
  • the halosulfonylation agent may suitably be selected from e.g. a halosulfonic acid compound such as chlorosulfonic acid or bromosulfonic acid.
  • halosulfonylation agent may be used in an amount of from 1 to 100 times by mol, preferably from 1 to 10 times by mol, to the compound of the formula (V).
  • This reaction may be carried out in the presence of a solvent, as the case requires.
  • the solvent may be any solvent so long as it is inert to the reaction, and one or more may suitably be selected for use from e.g. an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or dimethoxyethane; a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic
  • hydrocarbon such as chlorobenzene or dichlorobenzene
  • an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane
  • organic acid such as acetic acid or propionic acid
  • the reaction temperature is usually from -10°C to 200°C, preferably from 10°C to 150°C.
  • the reaction time is usually from about 0.2 to 48 hours, preferably from 0.5 to 24 hours.
  • the second stage can be carried out by the reaction in the presence of a reducing agent in acetic acid.
  • a reducing agent one or more may suitably be selected for use from e.g. a phosphorus compound such as red phosphorus or triphenyl phosphine; and a halogenated compound such as potassium iodide or iodine.
  • the reducing agent may be used in an amount of from 1 to 100 times by mol, preferably from 1 to 10 times by mol, to the compound of the formula (VI).
  • the reaction temperature is usually from 0°C to 200°C, preferably from 0°C to 150°C.
  • the reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.
  • the third stage can be carried out by the reaction in the presence of water and a base in a solvent.
  • the base may, for example, be the same one as in the above process [1].
  • the base may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 5 times by mol, to the compound of the formula (VII).
  • the solvent may, for example, be the same one as in the above process [1 ].
  • the reaction temperature is usually from -20 to 150°C, preferably from 0°C to 100°C.
  • the reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.
  • the fourth stage can be carried out usually by reacting the compound of the formula (VIII) or (IX) with the compound of the formula (X) in the presence of a base in a solvent.
  • the base may, for example, be the same one as in the above process [1].
  • the base may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 5 times by mol, to the compound of the formula (VIII).
  • This reaction may be carried out, as the case requires, in the presence of a radical initiator.
  • the radical initiator may be suitably selected for use from e.g.
  • the radical initiator may be used in an amount of from 0 to 5 times by mol, preferably from 0.1 to 2 times by mol, to the compound of the formula (VIII).
  • the solvent may, for example, be the same one as in the above process [1].
  • the reaction temperature is usually from -50 to 200°C, preferably from 0 to
  • the reaction time is usually from 0.5 to 72 hours, preferably from 1 to 48 hours.
  • a compound of the formula (ll-b-2) can be produced, for example, by the following reaction.
  • X R 1 , R 2 and R 3 are as defined above.
  • This reaction can be carried out by reacting a compound of the formula (ll-b-1) in the presence of an oxidizing agent in a solvent.
  • the oxidizing agent may, for example, be the same one as in the above process [2].
  • the oxidizing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (ll-b-1).
  • This reaction may be carried out, as the case requires, in the presence of a catalyst.
  • the catalyst may be selected for use from e.g. sodium tungstate, flavin, etc.
  • the catalyst may be used in an amount of from 0.0001 to 1 time by mol, preferably from 0.001 to 0.05 time by mol, to the compound of the formula (ll-b-1).
  • the solvent may be any solvent so long as it is inert to the reaction, and for example, one or more may suitably be selected for use from e.g. a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; an ester such as ethyl acetate or ethyl propionate; and acetic acid.
  • a halogenated alkane such as chloroform, dichloromethane or dichloroethane
  • an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene
  • an ester such as ethyl acetate or ethyl propionate
  • acetic acid e.g. a halogenated alkane such as chloroform, dichloromethane or dichloroethane
  • an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene
  • an ester such as e
  • the reaction temperature is usually from -50 to 150°C, preferably from 0 to 50°C.
  • the reaction time is usually from 0.5 to 48 hours, preferably from 1 to 30 hours.
  • a compound of the formula (ll-a-1 ) can be produced, for example, by the following reaction.
  • X R 1 , R 2 , R 3 and n are as defined above.
  • the compound of the formula (ll-b) is reacted with a metal reagent, then reacted with a trialkylborane and finally hydrolyzed with an acid.
  • the metal reagent one or more may suitably be selected for use from e.g. a magnesium compound such as magnesium or isopropyl magnesium chloride; and a lithium compound such as lithium chloride or n-butyl lithium.
  • the metal reagent may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 3 times by mol, to the compound of the formula (ll-b).
  • the trialkylborane one or more may suitably be selected for use from e.g. trimethylborane, triethylborane,
  • the trialkylborane may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 2 times by mol, to the compound of the formula (Ilb).
  • the acid one or more may suitably be selected for use from e.g. acetic acid, hydrochloric acid, sulfuric acid, etc.
  • the acid may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 3 times by mol, to the compound of the formula (ll-b).
  • one or more may suitably be selected for use from e.g. an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or
  • dimethoxyethane an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; and an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane.
  • aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene
  • aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane.
  • the reaction is carried out usually in an inert gas atmosphere such as nitrogen gas or argon gas.
  • the temperature for the reaction is usually from -150°C to 150°C, preferably from -100°C to 100°C.
  • the reaction time is usually from about 0.5 to 48 hours, preferably from 1 to 24 hours.
  • the compound of the formula (ll-a-2) can be produced, for example, by the following reaction.
  • X R 1 , R 2 , R 3 and n are as defined above.
  • the transition metal catalyst may, for example, be the same one as in the above process [1].
  • the transition metal catalyst may be used in an amount of from 0.001 to 1 time by mol, preferably from 0.01 to 0.1 time by mol, to the compound of the formula (ll-b).
  • the base may, for example, be the same one as in the above process [1].
  • the solvent may, for example, be the same one as in the above process [1].
  • the reaction is carried out usually in an inert gas atmosphere such as nitrogen gas or argon gas.
  • the temperature for the reaction is usually from -20°C to 150°C, preferably from 0°C to 00°C.
  • the reaction time is usually from about 1 to 48 hours, preferably from 1 to 24 hours.
  • the pesticide containing the compound of the present invention is useful, for example, as an agent to control insects, mites, nematodes or soil pests which become problematic in the agricultural and horticultural fields, i.e. as an agricultural and horticultural insecticide, miticide, nematicide or soil pesticide or as an agent to control insects or mites parasitic on animals i.e. as an agent to control parasites on animals.
  • the compound of the present invention is useful as an agricultural and
  • insects e.g. aphids such as green peach aphid (Mvzus persicae) and cotton aphid (Aphis gossypii); agricultural insect pests such as diamondback moth (Plutella xyjostella), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), codling moth (Cvdia pomonella), bollworm(Heliothis zea), tobacco budworm (Heliothis virescens), gypsy moth (Lvmantria dispar), rice leafroller
  • aphids such as green peach aphid (Mvzus persicae) and cotton aphid (Aphis gosypii)
  • agricultural insect pests such as diamondback moth (Plutella xyjostella), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), codling moth (Cvd
  • plant parasitic mites such as two-spotted spider mite (Tetranvchus urticae), carmine spider mite (Tetranvchus cinnabarinus).
  • kanzawa spider mite Tetranvchus kanzawai
  • citrus red mite Panonychus citri
  • European red mite Panonvchus ulmi
  • plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, white-tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acrjs), and pine wood nematode (Bursaphelenchus xylophilus); and soil pests, e.g. isopods such as pillbugs (Armadillidium vulqare) and pillbugs (Porcellio scaber).
  • isopods such as pillbugs (Armadillidium vulqare) and pillbugs (Porcellio scaber).
  • the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. Particularly, it is more effective for controlling plant parasitic mites and agricultural insect pests, and accordingly it is useful as an insecticide or miticide. Further, it is effective against insect pests having acquired resistance to organophosphorus, carbamate, synthetic pyrethroid and/or neonicotinoid insecticides.
  • the compound of the present invention has excellent systemic properties, and by the application of the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention to soil treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.
  • insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be agricultural and horticultural insecticides, miticides, nematicides or soil pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.
  • the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water- based suspension concentrate, an oil-based suspension concentrate, water soluble granules, a water soluble powder, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation.
  • a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water- based suspension concentrate, an oil-based suspension concentrate, water soluble granules, a water soluble powder, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation.
  • a formulation such as a dust
  • Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone,
  • anionic surfactants such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkyl
  • each of the components as such adjuvants may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use. For example, various adjuvants which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, an anti-mold agent, and so on, may also be employed.
  • the weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001 :99.999 to 95:5, preferably from
  • such a formulation may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders e.g. surfactants, vegetable oils or mineral oils may be added thereto, as the case requires.
  • a diluent such as water
  • various spreaders e.g. surfactants, vegetable oils or mineral oils
  • the nematicide or soil pesticide containing the compound of the present invention cannot generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects. However, it is usually applied in a concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 50,000 g, preferably from 1 to 30,000 g, per hectare. Further, the present invention includes such a method for controlling insects, mites, nematodes or soil pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.
  • compositions of the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e.g. mixing or drenching), surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed. Further, it is possible to feed domestic animals with a food
  • the active ingredient may also be applied by a so-called ultra low-volume application method.
  • the composition may be composed of 100% of the active ingredient.
  • the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity ⁇ reducing agents, whereby synergistic effects or activities may sometimes be obtained.
  • Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone, a plant growth regulating agent, and so on.
  • an insecticidal, miticidal, nematicidal or soil pesticidal composition having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals the application range, the application time, the pesticidal activities, etc. may be improved to preferred directions.
  • the compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together.
  • the present invention includes such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
  • the compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1 :300 to 300:1 , preferably from 1 :100 to 100:1 , by weight. Further, the dose for the application is such that the total amount of the active compounds is from 0.1 to 50,000 g, preferably from 1 to 30,000 g, per hectare.
  • the present invention includes a method for controlling insects, mites, nematodes or soil pests by an application of such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
  • the active ingredient compounds of an insect pest control agents such as the insecticide, the miticide, the nematicide or the soil insect pesticide in the above- mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
  • organic phosphate compounds such as profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos,
  • pyridaphenthion pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, phorate, phoxim and triazophos;
  • carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC and fenothiocarb;
  • nereistoxin derivatives such as cartap, thiocyclam, bensultap, thiosultap-sodium, thiosultap-disodium, monosultap, bisultap and thiocyclam hydrogen oxalate;
  • organic chlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor and dieldrin
  • organic metal compounds such as fenbutatin oxide and cyhexatin
  • pyrethroid compounds such as fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin,
  • benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron,
  • juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb and diofenolan;
  • pyridazinone compounds such as pridaben
  • pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole and pyriprole;
  • neonicotinoids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran and nithiazine;
  • hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide and halofenozide;
  • pyridine compounds such as pyridalyl and flonicamid
  • cyclic keto-enol compounds such as spirodiclofen; spiromesifen and
  • strobilurin compounds such as fluacrypyrim
  • pyrimidinamine compounds such as flufenerim
  • microbial agricultural chemicals such as insecticidal crystal proteins produced by Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect viruses, etomopathogenic fungi, and nematophagous fungi;
  • antibiotics or semisynthetic antibiotics such as avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin, emamectin and spinetoram; natural products, such as azadirachtin and rotenone; and repellents, such as deet.
  • the active ingredient compounds of the fungicide in the above-mentioned other agricultural chemicals include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
  • anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil and ferimzone;
  • triazoropyrimidine compounds such as 5-chloro-7-(4-methylpiperidin-1 -yl)-6- (2,4,6-trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine;
  • pyridinamine compounds such as fluazinam
  • azole compounds such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
  • tetraconazole oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole,
  • quinoxaline compounds such as quinomethionate
  • dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb and thiram;
  • organic chlorine compounds such as fthalide, chlorothalonil and quintozene
  • imidazole compounds such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, thiabendazole and fuberiazole;
  • cyanoacetamide compounds such as cymoxanil
  • anilide compounds such as metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benalaxyl, benalaxyl-M (another name: kiralaxyl, chiralaxyl), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isotianil, tiadinil and sedaxane;
  • sulfamide compounds such as dichlofluanid
  • copper compounds such as cupric hydroxide and oxine copper
  • isoxazole compounds such as hymexazol
  • organophosphorus compounds such as fosetyl-AI, tolclofos-methyl, S-benzyl 0,0-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate, aluminum ethylhydrogen phosphonate, edifenphos, and iprobenfos;
  • phthalimide compounds such as captan, captafol and folpet;
  • dicarboximide compounds such as procymidone, iprodione and vinclozolin;
  • benzanilide compounds such as flutolanil and mepronil
  • amide compounds such as penthiopyrad, mixture of 3-(difluoromethyl)-1 -methyl- N[(1 RS,4SR,9SR)-1 ,2,3,4-tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5- yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-1 -methyl-N-[(1 RS,4SR,9SR)-1 ,2,3,4- tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide
  • benzamide compounds such as fluopyram and zoxamide
  • piperazine compounds such as triforine
  • pyridine compounds such as pyrifenox
  • carbinol compounds such as fenarimol
  • piperidine compounds such as fenpropidin
  • morpholine compounds such as fenpropimorph and tridemorph
  • organotin compounds such as fentin hydroxide and fentin acetate
  • urea compounds such as pencycuron
  • cinnamic acid compounds such as dimethomorph and flumorph
  • phenylcarbamate compounds such as diethofencarb
  • cyanopyrrole compounds such as fludioxonil and fenpiclonil
  • strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, and fluoxastrobin;
  • oxazolidinone compounds such as famoxadone
  • thiazolecarboxamide compounds such as ethaboxam
  • valinamide compounds such as iprovalicarb and benthiavalicarb-isopropyl
  • acylamino acid compounds such as methyl N-(isopropoxycarbonyl)-L-valyl- (3RS)-3-(4-chlorophenyl)- -alaninate (valiphenalate);
  • imidazolinone compounds such as fenamidone
  • hydroxyanilide compounds such as fenhexamid
  • benzenesulfonamide compounds such as flusulfamide
  • oxime ether compounds such as cyflufenamid
  • antibiotics such as validamycin, kasugamycin and polyoxins
  • guanidine compounds such as iminoctadine and dodine
  • quinoline compounds such as 6-tert-butyl-8-fluoro-2,3-dimethylquinolin- 4-yl acetate (tebufloquin);
  • thiazolidine compounds such as (z)-2-(2-fluoro-5-(trifluromethyl)phenylthio)-2-(3- (2-methoxyphenyl)thiazolidin-2-yliden)acetonitrile (flutianil);
  • agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may , for example, be the active ingredient compounds in the herbicides as disclosed in The Pesticide Manual(15th edition), particularly those of soil treatment type.
  • the pesticides against parasites on animals are effective for controlling e.g.
  • harmful external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or harmful internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasites.
  • the external parasites may, for example, be animal parasitic acarus or fleas.
  • the animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphvsalis lonqicornis, Haemaphvsalis flava, Haemaphvsalis campanulata, Haemaphvsalis concinna, Haemaphvsalis japonica, Haemaphvsalis kitaokai, Haemaphvsalis ias, Ixodes oyatus, Ixodes
  • the pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of ticks among them.
  • the animal parasitic fleas may, for example, be externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Pulicidae,
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga qallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus.
  • the pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of fleas belonging to
  • Pulicidae particularly Ctenocephalides canis and Ctenocephalides felis, among them.
  • Other external parasites may, for example, be sucking lice (An jolura) such as shortnosed cattle louse (Haematopinus eurysternus), horse sucking louse
  • the internal parasites may, for example, be nematodes such as lung worms, whipworms
  • trematoda such as Spirometra erinacei, Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps, Echinococcus granulosus, and Echinococcus multilocularis; trematoda such as
  • Schistosoma iaponicum and Fasciola hepatica and protozoa such as coccidia, malaria parasites (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and Cryptosporidium.
  • the host animals may, for example, be pet animals, domestic animals, and poultry, such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries), cows, horses, pigs, sheep, ducks and chickens.
  • the pesticides against parasites on animals, containing the compounds of the present invention are particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control of external parasites, among them.
  • the compound of the present invention when used as a pesticide against parasites on animals, it may be used as it is or may be used together with suitable adjuvants, as formulated into various formulations such as a dust, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable concentrate, a water-based suspension concentrate and an oil-based suspension concentrate. In addition to such formulations, it may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention.
  • the adjuvants to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as adjuvants for formulation of agricultural and horticultural insecticide, miticide, nematicide or soil pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, acetone, acetonitrile, N-methylacetamide, ⁇ , ⁇ -dimethylacetamide, N,N-dimethylformamide, 2- pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol,
  • the blend ratio of the compound of the present invention to various adjuvants is usually from 0.1 :99.9 to 90:10, by weight. In the actual use of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e.g. surfactants, vegetable oils or mineral oils) may be added thereto, as the case requires.
  • a diluent such as water
  • various spreaders e.g. surfactants, vegetable oils or mineral oils
  • Administration of the compound of the present invention to a host animal is carried out orally or parenterally.
  • an oral administration method a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned.
  • a parenteral administration method there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e.g.
  • intravenous administration intramuscular administration, intradermal administration, hypodermic administration, etc.
  • a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal
  • the dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the deceased symptom, etc., but it is usually administered in a proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal.
  • the present invention also includes a method for controlling a pest by the above- mentioned administration method or by the above-mentioned dose, particularly a method for controlling external parasites or internal parasites.
  • the present invention by controlling pests parasitic on animals as described above, it is possible to prevent or cure various diseases of the host animal thereby caused in some cases.
  • the present invention also includes a
  • preventive or therapeutic agent for an animal disease caused by parasites containing the compound of the present invention as an active ingredient, and a method for preventing or curing an animal disease caused by parasites.
  • various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc. may be used in admixture with or in combination with the
  • the present invention includes such a mixed pesticidal composition having the above-mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.
  • a mixed solution comprising 1.0 g of 5-b omo-2,2-difluorobenzo[d][1 ,3]dioxole, 1.4 g of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.12 g of tetrakis(triphenylphosphine)palladium, 0.89 g of sodium carbonate, 5 mL of
  • a mixed solution comprising 0.11 g of 6-bromoquinazoline, 0.16 g of (2-fluoro-4- methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.030 g of
  • a mixed solution comprising 0.71 g of 5-bromo-2,2-difluorobenzo[d][1 ,3]dioxole,
  • a mixed solution comprising 10 g of (5-bromo-4-chloro-2-methylphenyl)-2,2,2- trifluoroethyl sulfide and 80 mL of diethyl ether was cooled to -70°C in a nitrogen atmosphere.
  • 21 mL of n-butyllithium n-hexane solution, 1.59 mol/L was dropwise added over a period of 10 minutes.
  • a mixed solution comprising 3.4 g of trimethoxy borane and 25 mL of diethyl ether, was dropwise added over 15 minutes at a temperature of from -60°C to -55°C.
  • Me represents methyl, Et ethyl, n-Pr n-propyl, i-Pr isopropyl, n-Bu n-butyl, i-Bu isobutyl, s-Bu secondary butyl, t-Bu tert-butyl, n-Pentyl n-pentyl, Ph phenyl, and Py pyridyl and 2-F-Ph represents phenyl substituted with F at the 2-position, and 3-CF 3 -2-Py 2-pyridyl substituted with CF 3 at the 3-position.
  • a compound identified with "-" represents one not substituted with R 4
  • a compound identified with "4-F” indicates that only the substitution position identified in the chemical structural formula in the Table is substituted with R 4 , i.e. only the 4-position is substituted with a fluorine atom.
  • the numerical value shown in the column for the physical properties is a melting point (°C).
  • H-NMR data [measured by 1 H-Nuclear magnetic resonance spectroscopy, ⁇ is a chemical shift] are shown in Tables 56 and 57. In Tables 1 to 57, No. represents the compound number.
  • An insecticidal solution was prepared to bring the concentration of the compound of the present invention to 50 ppm.
  • a kidney bean having only one primordial leaf left was transplanted to a pot ( diameter: 8 cm, height: 7 cm ), and 20 adults of two-spotted spider mite were released thereon. Together with the kidney bean leaf, they were dipped in the above insecticidal solution for about 5 seconds, dried in air and then left in a constant temperature chamber at 25°C with lightening.
  • the number of dead adults were counted, and the mortality of adults was calculated by the following equation.
  • Adults that dropped from the leaf or were moribund were included in the number of dead. The test was carried out with respect to the above-mentioned Compound Nos.
  • Rice seedling was dipped for about 10 seconds in an insecticidal solution adjusted to bring the concentration of the compound of the present invention to 200 ppm and then dried in air, its root was wrapped with a wet absorbent cotton, and the seedling was put into a test tube. Then, 20 second-third instar nymphs of brown planthopper were released therein, and the test tube was covered with a gauze and left in a constant temperature chamber at 25°C with lightening. On the 5th day after the release, the number of dead nymphs were counted, and the mortality was calculated by the following equation.
  • the above components are uniformly mixed to obtain a wettable powder.
  • the above components are uniformly mixed to obtain a dust.
  • the mixture of the above components is mixed with compound of the present invention in a weight ratio of 4:1 to obtain a wettable powder.
  • the above components are uniformly mixed and pulverized to obtain a base liquid, and
  • the above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules.
  • the above components are uniformly mixed and dissolved to obtain an ultra low volume formulation.

Abstract

To provide a novel pesticide. The present invention provides a compound represented by the formula (I) or its salt, and a pesticide containing it as an active ingredient: (I) wherein each of R1 and R2 is a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano, R3 is alkyl or haloalkyl, n is an integer of 0 or 1, and Q is any of the formulae [Q-1] to [Q-6].

Description

DESCRIPTION
TITLE OF INVENTION: PESTICIDE TECHNICAL FIELD
The present invention relates to a pesticide containing, as an active ingredient, the after-described novel compound represented by the formula (I) or its salt, i.e. a 3- arylphenyl sulfide derivative or its salt. BACKGROUND ART
Patent Document 1 discloses a 3-arylphenyl sulfide derivative useful as an insecticide or miticide. However, the compound of the formula (I) or its salt is not disclosed.
Further, Patent Document 2 discloses a (3-sulfur atom-substituted phenyl) heteroaryl derivative useful as an insecticide or miticide. However, the compound of the formula (I) or its salt is not disclosed.
PRIOR ART DOCUMENTS PATENT DOCUMENTS
Patent Document 1 : WO99/55668
Patent Document 2: JP-A-2008-308448
DISCLOSURE OF INVENTION TECHNICAL PROBLEM
For many years, many pesticides have been used, but many of them have various problems such that the effects are inadequate, their use is restricted as insects, etc. have acquired resistance, etc. Accordingly, it is desired to develop a novel pesticide substantially free from such problems. SOLUTION TO PROBLEM
The present inventors have conducted various studies on 3-arylphenyl sulfide derivatives in an effort to find a superior pesticide. As a result, they have found that the after-described novel compound of the formula (I) or its salt has a very high controlling effect against pests at a low dose and at the same time has safety to crop plants or mammals, and have accomplished the present invention.
That is, the present invention provides the following (1) to (16).
(1 ) A compound represented by the formula (I) or its salt:
Figure imgf000003_0001
(I)
wherein each of R1 and R2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyi, haloalkyi, alkoxy, haloalkoxy or cyano; R3 is alkyi or haloalkyi; n is an integer of 0 or 1 ; and Q is any of the following formulae [Q-1] to [Q-6]:
Figure imgf000004_0001
Figure imgf000004_0002
[Q-4] [Q-5] [Q-6]
wherein each of A1 to A8 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of A1 to A8 is CH, it may be substituted by R4, and among A1 to A8, the number of groups which may be nitrogen atoms, is from 0 to 3; each of B1 to B4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of B1 to B4 is CH, it may be substituted by R4, and among B1 to B4, the number of groups which may be nitrogen atoms, is from 0 to 1 ; each of B5 to B7 which may be the same or different from one another, is C(R5)(R6), an oxygen atom, a sulfur atom, SO or S02; each of E1 to E4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of E1 to E4 is CH, it may be substituted by R4, and among E1 to E4, the number of groups which may be nitrogen atoms, is from 0 to 1 ; each of E5 to E8 which may be the same or different from one another, is C(R5)(R6), an oxygen atom, a sulfur atom, SO or SO2; each of G1 to G5 and G7 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of G1 to G5 and G7 is CH, it may be
substituted by.R4, and among G1 to G5 and G7, the number of groups which may be nitrogen atoms, is from 0 to 3; G6 is an oxygen atom or a sulfur atom; each of J1 to J6 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of J1 to J6 is CH, it may be substituted by R4, and among J1 to J6, the number of groups which may be nitrogen atoms, is from 0 to 2; each of L1 to L5 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of L1 to L5 is CH, it may be substituted by R4, and among L1 to L5, the number of groups which may be nitrogen atoms, is from 0 to 2; L6 is an oxygen atom or a sulfur atom; R4 is a halogen atom, alkyl, haloalkyi, alkoxy, haloalkoxy, cyano, nitro, COR7, CO2R7, N(R8)COR7, N(R8)CO2R7, NR9R10, CONR9R10, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, phenyl which may be substituted by R11, or pyridyl which may be substituted by R11, provided that when the number of R4 is two or more, the plurality of R4 may be the same or different; each of R5 and R6 which are independent of each other, is a hydrogen atom, a halogen atom, alkyl or haloalkyi, provided that when the number of R5 or R6 is two or more, the plurality of R5 or R6 may be the same or different; each of R7, R8, R9 and R 0 which are independent of one another, is a hydrogen atom or alkyl; when R9 and R10 are alkyl, R9 and R10 may, together with the nitrogen atom to which they are bonded, form a 5- or 6-membered ring; and R11 is a halogen atom, alkyl, haloalkyi, alkoxy or haloalkoxy.
(2) The compound or its salt according to the above (1), wherein Q is any of the formulae [Q-1] to [Q-5].
(3) The compound or its salt according to the above (1), wherein Q is the formula [Q- 1], [Q-2] or [Q-4].
(4) The compound or its salt according to the above (1 ), wherein R1 is a hydrogen atom, a halogen atom, alkyl or alkoxy; R2 is a hydrogen atom, a halogen atom, alkyl or alkoxy; R3 is alkyl or haloalkyl; and Q is the formula [Q-1], [Q-2] or [Q-4].
(5) The compound or its salt according to the above (1), wherein Q is the formula [Q- 1] or [Q-2].
(6) The compound or its salt according to the above (1), wherein R1 is a hydrogen atom, a halogen atom, alkyl or alkoxy; R2 is a hydrogen atom, a halogen atom, alkyl or alkoxy; R3 is alkyl or haloalkyl; and Q is the formula [Q-1] or [Q-2].
d represented by the formula (II):
Figure imgf000005_0001
(Π)
wherein X is a bromine atom, -B(OH)2 or pinacolatoboranyl; n is an integer of 0 or 1 ; each of R and R2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; R3 is alkyl or haloalkyl, provided that a case wherein R1 is a hydrogen atom or a fluorine atom, R2 is methyl, and R3 is trifluoroethyl, is excluded.
(8) The compound according to the above (7), wherein R is a fluorine atom, a chlorine atom or methyl; and R2 is a chlorine atom or methyl.
(9) The compound according to the above (7), wherein R is a chlorine atom; and R2 is a chlorine atom or methyl.
(10) The compound according to the above (7), (8) or (9) wherein n is 0; and R3 is trifluoroethyl, trifluoropropyl, difluoroethyl or n-propyl.
(11) A pesticide containing the compound or its salt as defined in the above (1 ), as an active ingredient.
(12) An insecticide, miticide, nematicide or soil pesticide containing the compound or its salt as defined in the above (1), as an active ingredient.
(13) An insecticide or miticide containing the compound or its salt as defined in the above (1), as an active ingredient.
(14) A method for controlling pests, which comprises applying an effective amount of the compound or its salt as defined in the above (1 ) thereto.
(15) A method for controlling insects, mites, nematodes or soil pests, which comprises applying an effective amount of the compound or its salt as defined in the above (1 ) thereto.
(16) A method for controlling insects or mites, which comprises applying an effective amount of the compound or its salt as defined in the above (1) thereto.
ADVANTAGEOUS EFFECTS OF INVENTION
A pesticide containing the above compound of the formula (I) or its salt as an active ingredient has a very high controlling effect against pests at a low dose and at the same time has safety to crop plants or mammals. DESCRIPTION OF EMBODIMENTS
As the halogen atom in the formula (I) or the halogen atom as a substituent, an atom of fluorine, chlorine, bromine or iodine may be mentioned. The number of the halogen atoms as the substituents may be 1 or more, and if more, the respective halogen atoms may be the same or different. Further, the positions for substitution with such halogen atoms may be any positions.
The alkyl or alkyl moiety in the formula (I) may be linear or branched. As its specific example, Ci-6 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec- butyl, tert-butyl, pentyl or hexyl may be mentioned.
The pyridyl which may be substituted with R11 in the formula (I) may, for example, be 2-pyridyl, 3-pyridyl or 4-pyridyl. When the pyridyl is substituted with R11 , the number of substituents is from 1 to 4. Further, when it is substituted with a plurality of
R11 , the plurality of R1 may be the same or different.
When the phenyl in the formula (I) is substituted with R 1, the number of substituents is from 1 to 5. Further, when it is substituted with a plurality of R11 , the plurality of R11 may be the same or different.
The salt of the compound of the above formula (I) includes all kinds so long as they are acceptable in this technical field. For example, an ammonium salt such as a dimethyl ammonium salt or a triethyl ammonium salt; an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate; or an organic acid salt such as an acetate or a methane sulfonate, may be mentioned.
The compound of the above formula (I) may have isomers such as optical isomers, and such isomers and mixtures thereof are both included in the present invention. In this specification, isomers are in the form of a mixture, unless otherwise specified. Further, in the present invention, various isomers other than those mentioned above, may be included within the scope of the common knowledge in this technical field. Further, depending upon the type of the isomer, it may have a chemical structure different from the above formula (I), but for those skilled in the art, it can sufficiently be recognized that it is in an isomeric relationship and falls within the scope of the present invention.
The compound of the above formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) and its raw material compound can be produced by the following processes [1 ] and [2] and in accordance with a usual process for producing a salt. However, the present invention is by no means limited to such processes. Further, the above formula (II) representing an intermediate for the production of the compound of the formula (I) or its salt, is constituted by the formula (ll-a), and the formula (ll-b). ESS [1]
Figure imgf000007_0001
In the process [1], Q, R1, R2, R3 and n are as defined above. X' is -B(OH)2 or pinacolatoboranyl, and X" is a bromine atom.
Route A in the process [1] can be carried out by reacting the compound of the formula (III) and the compound of the formula (ll-a) in the presence of a base and a transition metal catalyst in a solvent.
Route B in the process [1] can be carried out by reacting the compound of the formula (IV) and a compound of the formula (ll-b) in the presence of a base and a transition metal catalyst in a solvent. The compounds of the formulae (ll-a) and (ll-b) include novel compounds and can be produced by a method disclosed in
WO2007/034755.
The compound of the formula (IV) may be a known compound or may be produced by reacting the corresponding magnesium reagent or lithium reagent with trimethyl borate.
The transition metal catalyst may suitably be selected for use from e.g. a palladium compound such as palladium-activated carbon, palladium acetate, dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium or tris(dibenzalacetone)palladium; and a nickel compound such as
bis(triphenylphosphine)nickel chloride or tetrakis(triphenylphosphine)nickel. The transition metal catalyst may be used in an amount of from 0.001 to 1 time by mol, preferably from 0.01 to 0.1 time by mol, to the compound of the formula (III) or the formula (ll-b).
As the base, one or more may suitably be selected for use from e.g. an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkaline earth metal hydroxide such as calcium hydroxide or magnesium hydroxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal bicarbonate such as sodium hydrogen carbonate or potassium hydrogen carbonate; an alkali metal acetate such as sodium acetate or potassium acetate; a metal hydride such as sodium hydride or potassium hydride; a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium tert-butoxide; and an organic base such as triethylamine, Ν,Ν-dimethylaniline, pyridine, 4-N,N-dimethylamino pyridine or 1 ,8- diazabicyclo[5.4.0]-7-undecene. The base may be used in an amount of from 1 to 5 times by mol, preferably from 1.5 to 3 times by mol, to the compound of the formula (III) or (ll-b). The solvent may be any solvent so long as it is inert to the reaction. For example, one or more may suitably be selected for use from e.g. an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or dimethoxy ethane; an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; an aprotic polar solvent such as Ν,Ν-dimethylformamide, Ν,Ν-dimethylacetamide, N-methyl-2- pyrolidone, dimethylsulfoxide or sulforane; a nitrile such as acetonitrile or propionitrile; an ester such as ethyl acetate or ethyl propionate; an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane; and a protonic solvent such as water, methanol or ethanol.
The reaction temperature is usually from -50 to 200°C, preferably from 20 to
150°C.
The reaction time is usually from 0.5 to 48 hours, preferably from 1 to 24 hours.
Figure imgf000008_0001
(I-a) (I-b)
In the process [2], Q, R1, R2 and R3 are as defined above. This reaction can be carried out by reacting the compound of the formula (l-a) in the presence of an oxidizing agent in a solvent.
The oxidizing agent may suitably be selected for use from e.g. an aqueous hydrogen peroxide solution, m-chloroperbenzoic acid, perbenzoic acid, sodium periodide, OXONE (tradename of E.I. du Pont; containing potassium hydrogen peroxosulfate), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite and sodium hypochlorite. The oxidizing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (l-a).
This reaction may be carried out, if necessary, in the presence of a catalyst. The catalyst may be selected for use from e.g. sodium tungstate and flavin. The catalyst may be used in an amount of from 0.0001 to 1 time by mol, preferably from 0.001 to 0.05 time by mol, to the compound of the formula (l-a).
The solvent may be any solvent so long as it is inert to the reaction. For example, one or more may suitably be selected for use from e.g. a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; an ester such as ethyl acetate or ethyl propionate; and acetic acid.
The reaction temperature is usually from -50 to 150°C, preferably from 0 to 50°C. The reaction time is usually from 0.5 to 48 hours, preferably from 1 to 30 hours. [Process 1 for intermediate]
Among compounds included in the formula (ll-b) for the starting material in the process [1], a compound of the formula (ll-b-1) may be produced, for example, by the reactions of the following (1) to (4).
(1) First stage of halosulfonylating a compound of the formula (V) to obtain a compound of the formula (VI).
(2) A second stage of reducing the compound of the formula (VI) to obtain a compound of the formula (VII).
(3) A third stage of hydrolyzing the compound of the formula (VII) to obtain a compound of the formula (VIII) or (IX).
(4) A fourth stage of reacting the compound of the formula (VIII) or (IX) with a compound of the formula (X) to obtain a compound of the formula (ll-b).
Now, (1 ) to (4) will be described in detail. In the following formulae, X", R1, R2 and R3 are as defined above, W is a halogen atom, and L is a halogen atom, a mesyl
Figure imgf000009_0001
(1) The first stage can be carried out in the presence of a halosulfonylation agent. The halosulfonylation agent may suitably be selected from e.g. a halosulfonic acid compound such as chlorosulfonic acid or bromosulfonic acid. The
halosulfonylation agent may be used in an amount of from 1 to 100 times by mol, preferably from 1 to 10 times by mol, to the compound of the formula (V).
This reaction may be carried out in the presence of a solvent, as the case requires. The solvent may be any solvent so long as it is inert to the reaction, and one or more may suitably be selected for use from e.g. an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or dimethoxyethane; a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic
hydrocarbon such as chlorobenzene or dichlorobenzene; an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane; and an organic acid such as acetic acid or propionic acid.
The reaction temperature is usually from -10°C to 200°C, preferably from 10°C to 150°C.
The reaction time is usually from about 0.2 to 48 hours, preferably from 0.5 to 24 hours.
(2) The second stage can be carried out by the reaction in the presence of a reducing agent in acetic acid. As the reducing agent, one or more may suitably be selected for use from e.g. a phosphorus compound such as red phosphorus or triphenyl phosphine; and a halogenated compound such as potassium iodide or iodine. The reducing agent may be used in an amount of from 1 to 100 times by mol, preferably from 1 to 10 times by mol, to the compound of the formula (VI).
The reaction temperature is usually from 0°C to 200°C, preferably from 0°C to 150°C. The reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.
(3) The third stage can be carried out by the reaction in the presence of water and a base in a solvent.
The base may, for example, be the same one as in the above process [1]. The base may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 5 times by mol, to the compound of the formula (VII). The solvent may, for example, be the same one as in the above process [1 ].
The reaction temperature is usually from -20 to 150°C, preferably from 0°C to 100°C.
The reaction time is usually from 1 to 48 hours, preferably from 1 to 24 hours.
(4) The fourth stage can be carried out usually by reacting the compound of the formula (VIII) or (IX) with the compound of the formula (X) in the presence of a base in a solvent.
The base may, for example, be the same one as in the above process [1]. The base may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 5 times by mol, to the compound of the formula (VIII).
This reaction may be carried out, as the case requires, in the presence of a radical initiator. The radical initiator may be suitably selected for use from e.g.
sulfurous acid, a sulfite, or a sulfurous acid adduct such as Rongalite (tradename of
Kanto Kagaku, sodium/formaldehyde sulfoxylate). The radical initiator may be used in an amount of from 0 to 5 times by mol, preferably from 0.1 to 2 times by mol, to the compound of the formula (VIII).
The solvent may, for example, be the same one as in the above process [1]. The reaction temperature is usually from -50 to 200°C, preferably from 0 to
150°C.
The reaction time is usually from 0.5 to 72 hours, preferably from 1 to 48 hours. [Process 2 for intermediate]
Among compounds included in the formula (ll-b) for the starting material in the process [1], a compound of the formula (ll-b-2) can be produced, for example, by the following reaction. In the formulae, X", R1, R2 and R3 are as defined above.
Figure imgf000010_0001
This reaction can be carried out by reacting a compound of the formula (ll-b-1) in the presence of an oxidizing agent in a solvent.
The oxidizing agent may, for example, be the same one as in the above process [2]. The oxidizing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (ll-b-1).
This reaction may be carried out, as the case requires, in the presence of a catalyst. The catalyst may be selected for use from e.g. sodium tungstate, flavin, etc. The catalyst may be used in an amount of from 0.0001 to 1 time by mol, preferably from 0.001 to 0.05 time by mol, to the compound of the formula (ll-b-1).
The solvent may be any solvent so long as it is inert to the reaction, and for example, one or more may suitably be selected for use from e.g. a halogenated alkane such as chloroform, dichloromethane or dichloroethane; an aromatic hydrocarbon such as chlorobenzene or dichlorobenzene; an ester such as ethyl acetate or ethyl propionate; and acetic acid.
The reaction temperature is usually from -50 to 150°C, preferably from 0 to 50°C.
The reaction time is usually from 0.5 to 48 hours, preferably from 1 to 30 hours. [Process 3 for intermediate] Among compounds included in the formula (ll-a) for the starting material in the process [1], a compound of the formula (ll-a-1 ) can be produced, for example, by the following reaction. In the following formula, X", R1, R2, R3 and n are as defined above.
Figure imgf000011_0001
The compound of the formula (ll-b) is reacted with a metal reagent, then reacted with a trialkylborane and finally hydrolyzed with an acid.
As the metal reagent, one or more may suitably be selected for use from e.g. a magnesium compound such as magnesium or isopropyl magnesium chloride; and a lithium compound such as lithium chloride or n-butyl lithium. The metal reagent may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 3 times by mol, to the compound of the formula (ll-b). As the trialkylborane, one or more may suitably be selected for use from e.g. trimethylborane, triethylborane,
triisopropylborane, etc. The trialkylborane may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 2 times by mol, to the compound of the formula (Ilb).
As the acid, one or more may suitably be selected for use from e.g. acetic acid, hydrochloric acid, sulfuric acid, etc. The acid may be used in an amount of from 0.3 to 5 times by mol, preferably from 0.5 to 3 times by mol, to the compound of the formula (ll-b).
As the solvent, one or more may suitably be selected for use from e.g. an ether such as diethyl ether, butyl methyl ether, tetrahydrofuran, 1 ,4-dioxane or
dimethoxyethane; an aromatic hydrocarbon such as benzene, toluene, xylene or chlorobenzene; and an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane.
The reaction is carried out usually in an inert gas atmosphere such as nitrogen gas or argon gas.
The temperature for the reaction is usually from -150°C to 150°C, preferably from -100°C to 100°C.
The reaction time is usually from about 0.5 to 48 hours, preferably from 1 to 24 hours.
[Process 4 for intermediate]
Among compounds included in the formula (ll-a) for the starting material in the process [1], the compound of the formula (ll-a-2) can be produced, for example, by the following reaction. In the following formulae, X", R1, R2, R3 and n are as defined above.
Figure imgf000012_0001
The compound of the formula (ll-b) and compound of the formula (XI) are reacted in the presence of a base and a transition metal catalyst in a solvent.
The transition metal catalyst may, for example, be the same one as in the above process [1]. The transition metal catalyst may be used in an amount of from 0.001 to 1 time by mol, preferably from 0.01 to 0.1 time by mol, to the compound of the formula (ll-b).
The base may, for example, be the same one as in the above process [1].
The solvent may, for example, be the same one as in the above process [1]. The reaction is carried out usually in an inert gas atmosphere such as nitrogen gas or argon gas.
The temperature for the reaction is usually from -20°C to 150°C, preferably from 0°C to 00°C.
The reaction time is usually from about 1 to 48 hours, preferably from 1 to 24 hours.
Preferred embodiments of the pesticide containing the compound of the present invention will be described below. The pesticide containing the compound of the present invention is useful, for example, as an agent to control insects, mites, nematodes or soil pests which become problematic in the agricultural and horticultural fields, i.e. as an agricultural and horticultural insecticide, miticide, nematicide or soil pesticide or as an agent to control insects or mites parasitic on animals i.e. as an agent to control parasites on animals.
The compound of the present invention is useful as an agricultural and
horticultural insecticide, miticide, nematicide or soil pesticide. Specifically, it is effective to control insects, e.g. aphids such as green peach aphid (Mvzus persicae) and cotton aphid (Aphis gossypii); agricultural insect pests such as diamondback moth (Plutella xyjostella), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), codling moth (Cvdia pomonella), bollworm(Heliothis zea), tobacco budworm (Heliothis virescens), gypsy moth (Lvmantria dispar), rice leafroller
(Cnaphalocrocis medjnalis), smaller tea tortrix (Adoxophyes sp_J, Colorado potato beetle (Leptinotarsa decemlineata), cucurbit leaf beetle (Aulacophora femoralis), boll weevil (Anthonomus grandis), planthoppers, leafhoppers, scales, bugs, whiteflies, thrips, grasshoppers, anthomyiid flies, scarabs, black cutworm (Agrotis ipsilon), cutworm (Agrotis segetum) and ants; gastropods such as slugs and snails; hygienic insect pests such as tropical rat mite (Qrnithonvssus bacoti), cockroaches, housefly (Musca domestica) and house mosquito (Culex pipiens); stored grain insect such as angoumois grain moth (Sitotroga cerealella), adzuki bean weevil (Callosobruchus chinensis), red flour beetle (Tribolium castaneum) and mealworms; and household goods insect pests such as casemaking clothes moth (Tinea pellionella), black carpet beetle (Attagenus japonicus) and subterranean termites; mites, e.g. plant parasitic mites such as two-spotted spider mite (Tetranvchus urticae), carmine spider mite (Tetranvchus cinnabarinus). kanzawa spider mite (Tetranvchus kanzawai), citrus red mite (Panonychus citri), European red mite (Panonvchus ulmi), broad mite
(Polyphaqotarsonemus latus), pink citrus rust mite (Aculops pelekassi) and bulb mite (Rhizoqlyphus echinopus); and domestic mites such as mold mite (Tyrophaqus putrescentiae), Dermatophaqoides farinae, Chelacaropsis moorei; nematodes, e.g. plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, white-tip nematode (Aphelenchoides besseyi), strawberry bud nematode (Nothotylenchus acrjs), and pine wood nematode (Bursaphelenchus xylophilus); and soil pests, e.g. isopods such as pillbugs (Armadillidium vulqare) and pillbugs (Porcellio scaber). Among them, the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. Particularly, it is more effective for controlling plant parasitic mites and agricultural insect pests, and accordingly it is useful as an insecticide or miticide. Further, it is effective against insect pests having acquired resistance to organophosphorus, carbamate, synthetic pyrethroid and/or neonicotinoid insecticides. Moreover, the compound of the present invention has excellent systemic properties, and by the application of the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention to soil treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.
Another preferred embodiments of the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be agricultural and horticultural insecticides, miticides, nematicides or soil pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.
The agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention, is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water- based suspension concentrate, an oil-based suspension concentrate, water soluble granules, a water soluble powder, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation. However, so long as it is suitable for the purpose of the present invention, it may be formulated into any type of formulation which is commonly used in this field. Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone,
chlorobenzene, cyclohexane, dimethylsulfoxide, Ν,Ν-dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; anionic surfactants such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a salt of a condensate of naphthalene sulfonate with formaldehyde; nonionic surfactants such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, a polyethylene glycol, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil, and a polyoxypropylene fatty acid ester; vegetable and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, and liquid paraffins; and so on. Each of the components as such adjuvants may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use. For example, various adjuvants which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, an anti-mold agent, and so on, may also be employed.
The weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001 :99.999 to 95:5, preferably from
0.005:99.995 to 90:10.
In the actual application of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders e.g. surfactants, vegetable oils or mineral oils may be added thereto, as the case requires.
The application of the agricultural and horticultural insecticide, miticide,
nematicide or soil pesticide containing the compound of the present invention cannot generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects. However, it is usually applied in a concentration of the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 50,000 g, preferably from 1 to 30,000 g, per hectare. Further, the present invention includes such a method for controlling insects, mites, nematodes or soil pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.
Various formulations of the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e.g. mixing or drenching), surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed. Further, it is possible to feed domestic animals with a food
containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their excrements. Furthermore, the active ingredient may also be applied by a so-called ultra low-volume application method. In this method, the composition may be composed of 100% of the active ingredient.
Further, the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity^ reducing agents, whereby synergistic effects or activities may sometimes be obtained. Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone, a plant growth regulating agent, and so on. Especially, with an insecticidal, miticidal, nematicidal or soil pesticidal composition having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals, the application range, the application time, the pesticidal activities, etc. may be improved to preferred directions. The compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together. The present invention includes such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
The mixing ratio of the compound of the present invention to the active
compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1 :300 to 300:1 , preferably from 1 :100 to 100:1 , by weight. Further, the dose for the application is such that the total amount of the active compounds is from 0.1 to 50,000 g, preferably from 1 to 30,000 g, per hectare. The present invention includes a method for controlling insects, mites, nematodes or soil pests by an application of such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
The active ingredient compounds of an insect pest control agents, such as the insecticide, the miticide, the nematicide or the soil insect pesticide in the above- mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
organic phosphate compounds, such as profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos,
pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet, phorate, phoxim and triazophos;
carbamate compounds, such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC and fenothiocarb;
nereistoxin derivatives, such as cartap, thiocyclam, bensultap, thiosultap-sodium, thiosultap-disodium, monosultap, bisultap and thiocyclam hydrogen oxalate;
organic chlorine compounds, such as dicofol, tetradifon, endosulfan, dienochlor and dieldrin; organic metal compounds, such as fenbutatin oxide and cyhexatin; pyrethroid compounds, such as fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta-cypermethrin, beta-cyfluthrin, metofluthrin, phenothrin, flumethrin and decamethrin;
benzoylurea compounds, such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron,
noviflumuron and fluazuron;
juvenile hormone-like compounds, such as methoprene, pyriproxyfen, fenoxycarb and diofenolan;
pyridazinone compounds, such as pridaben;
pyrazole compounds, such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole and pyriprole;
neonicotinoids, such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran and nithiazine;
hydrazine compounds, such as tebufenozide, methoxyfenozide, chromafenozide and halofenozide;
pyridine compounds, such as pyridalyl and flonicamid;
cyclic keto-enol compounds, such as spirodiclofen; spiromesifen and
spirotetramat;
strobilurin compounds, such as fluacrypyrim;
pyrimidinamine compounds, such as flufenerim;
dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds;
other compounds, such as flupyradifurone, NNI-0711 (pyflubumide), flometoquin, buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen, triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1 ,3- dichloropropene, diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyantraniliprole, cyenopyrafen, pyrifluquinazon, fenazaquin, amidoflumet, sulfluramid, hydramethylnon, metaldehyde, HGW-86, ryanodine, verbutin, AKD-1022, chlorobenzoate,
thiazolylcinnanonitrile, sulfoxaflor, fluensulfone, 3-bromo-N-(2-bromo-4-chloro-6-(1- cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1 H-pyrazole-5- carboxyamide, 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)-6-methylphenyl)- 1 -(3-chloropyridin-2-yl)-1 H-pyrazole-5-carboxyamide, 3-bromo-N-(2-bromo-4-chloro-6- (cyclopropylmethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1 H-pyrazole-5- carboxyamide, 3-bromo-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1 -(3- chloropyridin-2-yl)-1 H-pyrazole-5-carboxyamide and 3-bromo-1-(3-chloropyridin-2-yl)- N-(4-cyano-2-methyl-6-(methylcarbamoyl)phenyl)-1 H-pyrazole-5-carboxyamide; and the like. Further, it may be used in combination with or together with microbial agricultural chemicals, such as insecticidal crystal proteins produced by Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect viruses, etomopathogenic fungi, and nematophagous fungi;
antibiotics or semisynthetic antibiotics, such as avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin, emamectin and spinetoram; natural products, such as azadirachtin and rotenone; and repellents, such as deet.
The active ingredient compounds of the fungicide in the above-mentioned other agricultural chemicals include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
anilinopyrimidine compounds, such as mepanipyrim, pyrimethanil, cyprodinil and ferimzone;
triazoropyrimidine compounds, such as 5-chloro-7-(4-methylpiperidin-1 -yl)-6- (2,4,6-trifluorophenyl)[1 ,2,4]triazolo[1 ,5-a]pyrimidine;
pyridinamine compounds, such as fluazinam;
azole compounds, such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
tetraconazole, oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole,
diniconazole, tricyclazole, probenazole, simeconazole, pefurazoate, ipconazole and imibenconazole;
quinoxaline compounds, such as quinomethionate;
dithiocarbamate compounds, such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb and thiram;
organic chlorine compounds, such as fthalide, chlorothalonil and quintozene; imidazole compounds, such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, thiabendazole and fuberiazole;
cyanoacetamide compounds, such as cymoxanil;
anilide compounds, such as metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benalaxyl, benalaxyl-M (another name: kiralaxyl, chiralaxyl), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isotianil, tiadinil and sedaxane;
sulfamide compounds, such as dichlofluanid;
copper compounds, such as cupric hydroxide and oxine copper;
isoxazole compounds, such as hymexazol;
organophosphorus compounds, such as fosetyl-AI, tolclofos-methyl, S-benzyl 0,0-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate, aluminum ethylhydrogen phosphonate, edifenphos, and iprobenfos;
phthalimide compounds, such as captan, captafol and folpet;
dicarboximide compounds, such as procymidone, iprodione and vinclozolin;
benzanilide compounds, such as flutolanil and mepronil;
amide compounds, such as penthiopyrad, mixture of 3-(difluoromethyl)-1 -methyl- N[(1 RS,4SR,9SR)-1 ,2,3,4-tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5- yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-1 -methyl-N-[(1 RS,4SR,9SR)-1 ,2,3,4- tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide
(isopyrazam), silthiopham, fenoxanil and furametpyr;
benzamide compounds, such as fluopyram and zoxamide;
piperazine compounds, such as triforine;
pyridine compounds, such as pyrifenox;
carbinol compounds, such as fenarimol;
piperidine compounds, such as fenpropidin; morpholine compounds, such as fenpropimorph and tridemorph;
organotin compounds, such as fentin hydroxide and fentin acetate;
urea compounds, such as pencycuron;
cinnamic acid compounds, such as dimethomorph and flumorph;
phenylcarbamate compounds, such as diethofencarb;
cyanopyrrole compounds, such as fludioxonil and fenpiclonil;
strobilurin compounds, such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, and fluoxastrobin;
oxazolidinone compounds, such as famoxadone;
thiazolecarboxamide compounds, such as ethaboxam;
valinamide compounds, such as iprovalicarb and benthiavalicarb-isopropyl;
acylamino acid compounds, such as methyl N-(isopropoxycarbonyl)-L-valyl- (3RS)-3-(4-chlorophenyl)- -alaninate (valiphenalate);
imidazolinone compounds, such as fenamidone;
hydroxyanilide compounds, such as fenhexamid;
benzenesulfonamide compounds, such as flusulfamide;
oxime ether compounds, such as cyflufenamid;
anthraquinone compounds;
crotonic compounds;
antibiotics, such as validamycin, kasugamycin and polyoxins;
guanidine compounds, such as iminoctadine and dodine;
quinoline compounds, such as 6-tert-butyl-8-fluoro-2,3-dimethylquinolin- 4-yl acetate (tebufloquin);
thiazolidine compounds, such as (z)-2-(2-fluoro-5-(trifluromethyl)phenylthio)-2-(3- (2-methoxyphenyl)thiazolidin-2-yliden)acetonitrile (flutianil);
and other compounds, such as pyribencarb, isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam- sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom
(another name: amibromdole), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2- methoxy-4-methylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3- trifluoromethylpyridine, pyriofenone, mandipropamid, fluopicolide, carpropamid, meptyldinocap, N-tiS'^'-dichloro-l .l-dimethy phenacy^-S-trifluoromethyl^- pyridinecarboxyamide, N-[(3',4'-dichloro- ,1 -dimethyl)phenacyl]-3-methyl-2- thiophencarboxyamide, N-[(3',4'-dichloro- ,1 -dimethyl)phenacyl]-1 -methyl-3- trifluoromethyl-4-pyrazolecarboxyamide, N-[[2'-methyl-4'-(2-propyloxy)-1 ,1 - dimethyl]phenacyl]-3-trifluoromethyl-2-pyridinecarboxyamide, N-[[2'-methyl-4'-(2- propyloxy)-1 , 1 -dimethyl]phenacyl]-3-methyl-2-thiophencarboxyamide, N-[[2'-methyl-4'- (2-propyloxy)-1 , 1 -dimethyl]phenacyl]-1 -methyl-3-trif luoromethyl-4- pyrazolecarboxyamide, N-[[4'-(2-propyloxy)-1 , 1 -dimethyl]phenacyl]-3-trifluoromethyl-2- pyridinecarboxyamide, N-[[4'-(2-propyloxy)-1 , 1 -dimethyl]phenacyl]-3-methyl-2- thiophencarboxyamide, N-[[4'-(2-propyloxy)-1 , 1 -dimethyl]phenacyl]-1 -methyl-3- trifluoromethyl-4-pyrazolecarboxyamide, N-[[2'-methyl-4'-(2-pentyloxy)-1 ,1 - dimethyl]phenacyl]-3-trifluoromethyl-2-pyridinecarboxyamide, N-[[4'-(2-pentyloxy)-1 ,1 - dimethyl]phenacyl]-3-trifluoromethyl-2-pyridinecarboxyamide, spiroxamine, S-2188 (fenpyrazamine), S-2200, ZF-9646, BCF-051 , BCM-061 and BCM-062.
Further, agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may , for example, be the active ingredient compounds in the herbicides as disclosed in The Pesticide Manual(15th edition), particularly those of soil treatment type.
The pesticides against parasites on animals are effective for controlling e.g.
harmful external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or harmful internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasites.
The external parasites may, for example, be animal parasitic acarus or fleas.
Their species are so many that it is difficult to list all of them, and therefore, their typical examples will be given.
The animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphvsalis lonqicornis, Haemaphvsalis flava, Haemaphvsalis campanulata, Haemaphvsalis concinna, Haemaphvsalis japonica, Haemaphvsalis kitaokai, Haemaphvsalis ias, Ixodes oyatus, Ixodes
nipponensis, Ixodes persulcatus, Amblyomma testudinarium, Haemaphvsalis
meqaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis; red mite
(Dermanvssus gallinae); northern fowl mites such as Ornithonvssus sylviarum, and Ornithonvssus bursa; trombiculidae such as Eutrombicula wichmanni,
Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji,
Leptotrombidium tosa, Neotrombicula autumnalis, Eutrombicula alfredduqesi, and
Helenicula mivaqawai; cheyletidae such as Cheyletiella vasguri, Cheyletiella
parasitivorax, and Cheyletiella blakei; sarcoptic mange mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cvnotis, Sarcoptes scabiei, and Notoedres cati; and Demodicidae such as Demodex canis. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of ticks among them.
The animal parasitic fleas may, for example, be externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Pulicidae,
Ceratephyllus, etc. Fleas belonging to Pulicidae may for example, be
Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga qallinacea, Xenopsylla cheopis, Leptopsylla segnis, Nosopsyllus fasciatus, and Monopsyllus anisus. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of fleas belonging to
Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among them.
Other external parasites may, for example, be sucking lice (An jolura) such as shortnosed cattle louse (Haematopinus eurysternus), horse sucking louse
(Haematopinus asini), sheep louse, longnosed cattle louse (Linognathus vituli), and head louse (Pediculus capitis); biting lice such as dog biting louse (Trichodectes canis); and blood-sucking dipterous insects such as horsefly (Tabanus trigonus), biting midges (Culicoides schultzei), and blackfly (Simulium ornatum). Further, the internal parasites may, for example, be nematodes such as lung worms, whipworms
(Trichuris), tuberous worms, gastric parasites, ascaris, and filarioidea; cestoda such as Spirometra erinacei, Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps, Echinococcus granulosus, and Echinococcus multilocularis; trematoda such as
Schistosoma iaponicum and Fasciola hepatica; and protozoa such as coccidia, malaria parasites (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and Cryptosporidium.
The host animals may, for example, be pet animals, domestic animals, and poultry, such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries), cows, horses, pigs, sheep, ducks and chickens. The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control of external parasites, among them.
Among pet animals or domestic animals, they are effective particularly for dogs and cats, cows and horses.
When the compound of the present invention is used as a pesticide against parasites on animals, it may be used as it is or may be used together with suitable adjuvants, as formulated into various formulations such as a dust, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable concentrate, a water-based suspension concentrate and an oil-based suspension concentrate. In addition to such formulations, it may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention. The adjuvants to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as adjuvants for formulation of agricultural and horticultural insecticide, miticide, nematicide or soil pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, acetone, acetonitrile, N-methylacetamide, Ν,Ν-dimethylacetamide, N,N-dimethylformamide, 2- pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol,
isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, dipropylene glycol monomethyl ether, or dipropylene glycol n-butyl ether; an antioxidant such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium hydrogenmetasulfite, propyl gallate or sodium thiosulfate; a coating film- forming agent such as polyvinylpyrrolidone, polyvinyl alcohol, or a copolymer of vinyl acetate and vinyl pyrrolidone; the vegetable oils and mineral oils as exemplified above as adjuvants for formulation of agricultural and horticultural insecticide, miticide, nematicide or soil pesticides; a carrier such as lactose, sucrose, glucose, starch, wheat flour, corn powder, soybean cake and meal, defatted rice bran, calcium carbonate or other commercially available feed materials; and so on. One or more of the
respective components of these adjuvants may be suitably selected for use, so long as such will not depart from the purpose of the present invention. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use, and still further, some among the above-mentioned various adjuvants to be used in the agricultural and horticultural field may suitably be selected for use.
The blend ratio of the compound of the present invention to various adjuvants is usually from 0.1 :99.9 to 90:10, by weight. In the actual use of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e.g. surfactants, vegetable oils or mineral oils) may be added thereto, as the case requires.
Administration of the compound of the present invention to a host animal is carried out orally or parenterally. As an oral administration method, a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned. As a parenteral administration method, there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e.g. intravenous administration, intramuscular administration, intradermal administration, hypodermic administration, etc.; a method wherein it is administered on the body surface by spot-on treatment, pour-on treatment or spray treatment; or a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal.
The dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the deceased symptom, etc., but it is usually administered in a proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal.
The present invention also includes a method for controlling a pest by the above- mentioned administration method or by the above-mentioned dose, particularly a method for controlling external parasites or internal parasites.
Further, in the present invention, by controlling pests parasitic on animals as described above, it is possible to prevent or cure various diseases of the host animal thereby caused in some cases. Thus, the present invention also includes a
preventive or therapeutic agent for an animal disease caused by parasites, containing the compound of the present invention as an active ingredient, and a method for preventing or curing an animal disease caused by parasites.
When the compound of the present invention is used as a pesticide against parasites on animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc., may be used in admixture with or in combination with the
adjuvants. Further, as the case requires, other animal drugs or agricultural
chemicals, such as vermicides, anti-coccidium agents, insecticides, miticides, pulicides, nematicides, bactericides or antibacterial agents, may be mixed or combined for use, whereby improved effects may sometimes be obtained. The present invention includes such a mixed pesticidal composition having the above-mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.
EXAMPLES
Now, the present invention will be described in further detail with reference to Examples, but it should be understood that the present invention is by no means thereby restricted. Firstly, Preparation Examples for the compounds of the present invention will be described.
PREPARATION EXAMPLE 1
Preparation of 2,2-difluoro-5-(2-fluoro-4-methyl-5-((2,2,2,- trifluoroethyl)thio)phenyl)benzo[d][1 ,3]dioxole (compound No. 37-29)
A mixed solution comprising 1.0 g of 5-b omo-2,2-difluorobenzo[d][1 ,3]dioxole, 1.4 g of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.12 g of tetrakis(triphenylphosphine)palladium, 0.89 g of sodium carbonate, 5 mL of
tetrahydrofuran and 5 mL of water, was heated and refluxed for 18 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane/ethyl acetate=95/5 (volume ratio)) to obtain 1.6 g of the desired product as an oil.
PREPARATION EXAMPLE 2
Preparation of 2,2-difluoro-5-(2-fluoro-4-methyl-5-((2,2,2- trifluoroethyl)sulfinyl)phenyl)benzo[d][1 ,3]dioxole (compound No. 37-30)
To a mixed solution comprising 1.3 g of (2,2-diflluoro-5-(2-fluoro-4-methyl-5- ((2,2,2-trifluoroethyl)thio)phenyl)benzo[d][1 ,3]dioxole and 10 mL of ethyl acetate, 0.86 g of m-chloroperbenzoic acid was added dividedly in two times and reacted at room temperature for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with an aqueous sodium bicarbonate solution, water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane/ethyl acetate=60/40 (volume ratio)) to obtain 1.2 g of the desired product (melting point: 80-85°C).
PREPARATION EXAMPLE 3
Preparation of 6-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)quinazoline (compound No. 31-1 )
A mixed solution comprising 0.11 g of 6-bromoquinazoline, 0.16 g of (2-fluoro-4- methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.030 g of
tetrakis(triphenylphosphine)palladium, 0.1 g of sodium carbonate, 3 mL of
tetrahydrofuran and 3 mL of water, was heated and refluxed for 19 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane/ethyl acetate=50/50 (volume ratio)) to obtain 0.17 g of the desired product (melting point: 103-105°C).
PREPARATION EXAMPLE 4
Preparation of 5-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)-2,2- difluorobenzo[d][1 ,3]dioxole (compound No. 37-55)
A mixed solution comprising 0.71 g of 5-bromo-2,2-difluorobenzo[d][1 ,3]dioxole,
1.1 g of (2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid, 0.17 g of tetrakis(triphenylphosphine)palladium, 1.0 g of sodium carbonate, 15 mL of
tetrahydrofuran and 15 mL of water, was heated and refluxed for 13 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous magnesium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column
chromatography (eluent: n-heptane/ethyl acetate=98/2 (volume ratio)) to obtain 1.0 g of the desired product as an oil.
PREPARATION EXAMPLE 5
Preparation of 5-(2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)sulfinyl)phenyl)-2,2- difluorobenzo[d][1 ,3]dioxole (compound No. 37-56)
To a mixed solution comprising 1.0 g of 5-(2-chloro-4-methyl-5-((2,2,2- trifluoroethyl)thio)phenyl)-2,2-difluorobenzo[d][1 ,3]clioxole and 18 mL of chloroform, a mixed solution comprising 0.62 g of m-chloroperbenzoic acid and 8 mL of chloroform, was added and reacted at 0°C for 30 minutes and then at room temperature for one hour. The solvent was distilled off under reduced pressure, and an aqueous sodium bicarbonate solution was added to the residue, followed by extraction with ethyl acetate. Then, the organic layer was washed with an aqueous sodium chloride solution, and anhydrous magnesium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-heptane/ethyl acetate=85/15 (volume ratio)) to obtain 0.94 g of the desired product (melting point: 134-135°C).
PREPARATION EXAMPLE 6
Preparation of (5-bromo-4-chloro-2-methylphenyl)-2,2,2-trifluoroethyl sulfide
(intermediate compound No. 55-33)
(1 ) To 16 mL of chlorosulfonic acid, 8.0 g of 1-bromo-2-chloro-4-methylbenzene was dropwise added at 0°C and reacted at room temperature for 30 minutes and at 60°C for one hour. The reaction solution was left to cool to room temperature and then put into ice water, and precipitated crystals were collected by filtration and washed with water to obtain 12 g of 5-bromo-4-chloro-2-methylbenzene-1-sulfonyl chloride (melting point: 90-91 °C).
(2) To 12 g of 5-bromo-4-chloro-2-methylbenzene-1-sulfonyl chloride obtained in the above (1), 22 mL of acetic acid, 2.5 g of red phosphorus and 0.15 g of iodine were added, followed by heating and refluxing for 4.5 hours. The reaction mixture was left to cool to room temperature, and then, the solid was collected by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate and then washed with water, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution, and anhydrous magnesium sulfate was added for drying. The solvent was distilled off under reduced pressure to obtain 10 g of S-(5-bromo-4-chloro-2-methylphenyl)ethane thioate (melting point: 42-43°C).
(3) 9.8 g of S-(5-bromo-4-chloro-2-methylphenyl)ethane thioate obtained in the above (2), 25 mL of ethanol and 25 mL of water were mixed, and 3.5 g of sodium hydroxide was added, followed by a reaction at room temperature for 15 hours.
Ethanol was distilled off under reduced pressure, and the reaction solution was neutralized with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution, and anhydrous magnesium sulfate was added for drying. The solvent was distilled off under reduced pressure to obtain 8.1 g of solid 5-bromo-4-chloro-2-methylbenzenethiol (melting point: 75-77°C).
(4) To a mixed solution comprising 4.0 g of 5-bromo-4-chloro-2- methylbenzenethiol obtained in the above (3), 4.7 g of potassium carbonate, 2.6 g of Rongalite and 20 mL of N,N-dimethylformamide, 5.3 g of 1 ,1 ,1-trifluoro-2-iodoethane was dropwise added. After completion of the dropwise addition, the mixture was reacted at room temperature for 20 hours. Water was added to the reaction solution, followed by extraction with a mixed solvent of n-heptane/tert-butylmethylether=75/25 (volume ratio). Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous magnesium sulfate was added for drying. The solvent was distilled off under reduced pressure to obtain 5.3 g of the desired product as an oil.
PREPARATION EXAMPLE 7 . Preparation of (2-chloro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)boronic acid (intermediate compound No. 55-42)
A mixed solution comprising 10 g of (5-bromo-4-chloro-2-methylphenyl)-2,2,2- trifluoroethyl sulfide and 80 mL of diethyl ether was cooled to -70°C in a nitrogen atmosphere. To this solution, 21 mL of n-butyllithium (n-hexane solution, 1.59 mol/L) was dropwise added over a period of 10 minutes. After 10 minutes, a mixed solution comprising 3.4 g of trimethoxy borane and 25 mL of diethyl ether, was dropwise added over 15 minutes at a temperature of from -60°C to -55°C. Then, the temperature was raised to -20°C, and 60 g of 20% sulfuric acid was dropwise added and further reacted at room temperature for two hours. From this reaction mixture, an organic layer was separated, washed with water and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was washed with n-heptane to obtain 5.5 g of the desired product (melting point: 154-156°C).
Typical examples of the compound of the above formula (I) will be given in
Tables 1 to 54, and typical examples of the intermediate compound will be given in Table 55. These compounds can be prepared based on the above-described
Preparation Examples or the above-described various processes for the production of the compounds of the formula (I) and the intermediate compounds. In Tables 1 to 55, Me represents methyl, Et ethyl, n-Pr n-propyl, i-Pr isopropyl, n-Bu n-butyl, i-Bu isobutyl, s-Bu secondary butyl, t-Bu tert-butyl, n-Pentyl n-pentyl, Ph phenyl, and Py pyridyl and 2-F-Ph represents phenyl substituted with F at the 2-position, and 3-CF3-2-Py 2-pyridyl substituted with CF3 at the 3-position. Further, in the column for R4, a compound identified with "-" represents one not substituted with R4, and for example, a compound identified with "4-F" indicates that only the substitution position identified in the chemical structural formula in the Table is substituted with R4, i.e. only the 4-position is substituted with a fluorine atom. The numerical value shown in the column for the physical properties is a melting point (°C). Further, with respect to some of the compounds of the above formula (I) and the intermediate compounds, H-NMR data [measured by 1H-Nuclear magnetic resonance spectroscopy, δ is a chemical shift] are shown in Tables 56 and 57. In Tables 1 to 57, No. represents the compound number.
Figure imgf000025_0001
Figure imgf000026_0001
Figure imgf000028_0001
Figure imgf000029_0001
W
28
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
TABLE 7 (R4)
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
TABLE 13
Figure imgf000047_0001
Physical
No. R1 R2 R3 R4 n
properties
13-1 F Me CH2CF3 — 0 92.2
13-2 F Me CH2CF3 — 1 140-142
13-3 F Me CH2CF3 3-F 0
13-4 F Me CH2CF3 3-F 1
13-5 F Me CH2CF3 4-F 0 100.5
13-6 F Me CH2CF3 4-F 1
13-7 F Me CH2CF3 6-F 0
13-8 F Me CH2CF3 6-F 1
13-9 F Me CH2CF3 3-CI 0
13-10 F Me CH2CF3 3-CI 1
13-11 F Me CH2CF3 4-CI 0 120-123
13-12 F Me CH2CF3 4-CI 1 85-87
13-13 F Me CH2CF3 6-CI 0
13-14 F Me CH2CF3 6-CI 1
13-15 F Me CH2CF3 4-Me 0 Oil
13-16 F Me CH2CF3 6-Me 0 Oil
13-17 F Me CH2CF3 6-Me 1 149-151
13-18 F Me CH2CF3 4-CF3 0 95-99
13-19 F Me CH2CF3 6-CF3 0 71.7
13-20 F Me CH2CF3 6-CF3 1 119.3
13-21 F Me CH2CF3 3-OMe 0
13-22 F Me CH2CF3 4-OMe 0
13-23 F Me CH2CF3 6-OMe 0
13-24 F Me CH2CF3 3-OCF3 0
13-25 F Me CH2CF3 4-OCF3 0
13-26 F Me CH2CF3 6-OCF3 0
13-27 F Me CH2CF3 3-CN 0
13-28 F Me CH2CF3 4-CN 0
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
W 201
49
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
TABLE 18 (r4)
Figure imgf000054_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
Figure imgf000061_0001
Figure imgf000062_0001
TABLE 27
Figure imgf000063_0001
Figure imgf000064_0001
TABLE 29 S(0)nR3
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
„
TABLE 31 (conl inued)
Physical
No. R R2 R3 R4 n
properties
31-57 F Me GH2CF3 4-Br 0 86-88
31-58 F Me CH2CF3 4-Br 1 Oil
31-59 F Me CH2CF3 8-OCH2CF3 0 112-115
31-60 F Me CH2CF3 8-OCH2CF3 1 30-132
31-61 F Me CH2CF3 6-Ph 0 105-107
31-62 F Me CH2CF3 6-Ph 1 151-154
31-63 F Me CH2CF3 6,8-(OEt)2 0 87-89
31-64 F Me CH2CF3 6,8-(OEt)2 1
31-65 F Me CH2CF3 6,8-(OCH2CF3)2 0 88-90
31-66 F Me CH2CF3 6,8-(OCH2CF3)2 1 130-134
31-67 Me Me CH2CF3 4-Br 0 78-82
31-68 Me Me CH2CF3 4-Br 1 82-86
31-69 F Me CH2CHF2 4-Br 0 127-129
31-70 F Me CH2CHF2 4-Br 1 134-136
31-71 F Me Et — 1 110-111
Figure imgf000070_0001
Figure imgf000071_0001
TABLE 34
Figure imgf000072_0001
Figure imgf000073_0001
TABLE 36
Figure imgf000074_0001
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
36-1 F Me CH2CF3 — 0 CH2 CH2 0
36-2 F Me CH2CF3 — 0 CH2 CH2 1
36-3 F Me CH2CF3 — S CH2 CH2 0
36-4 F Me CH2CF3 — S CH2 CH2 1
36-5 F Me CH2CF3 — SO CH2 CH2 0
36-6 F Me CH2CF3 — SO CH2 CH2 1
36-7 F Me CH2CF3 — SO2 CH2 CH2 0
36-8 F Me CH2CF3 — SO2 CH2 CH2 1
36-9 F Me CH2CF3 — CH2 O CH2 0
36-10 F Me CH2CF3 — CH2 O CH2 1
36-11 F Me CH2CF3 — CH2 S CH2 0
36-12 F Me CH2CF3 — CH2 S CH2 1
36-13 F Me CH2CF3 — CH2 SO CH2 0
36-14 F Me CH2CF3 — CH2 SO CH2 1
36-15 F Me CH2CF3 — CH2 SO2 CH2 0
36-16 F Me CH2CF3 — CH2 SO2 CH2 1
36-17 F Me CH2CF3 — CH2 CH2 O 0
36-18 F Me CH2CF3 — CH2 CH2 O 1
36-19 F Me CH2CF3 — CH2 CH2 S 0
36-20 F Me CH2CF3 — CH2 CH2 S 1
36-21 F Me CH2CF3 — CH2 CH2 SO 0
36-22 F Me CH2CF3 — CH2 CH2 SO 1
36-23 F Me CH2CF3 — CH2 CH2 SO2 0
36-24 F Me CH2CF3 — CH2 CH2 SO2 1
36-25 F Me CH2CF3 — O CH2 O 0 Oil
36-26 F Me CH2CF3 — O CH2 O 1 Oil
36-27 F Me CH2CF3 — O CHF 0 0
36-28 F Me CH2CF3 — O CHF O 1 TABLE 36 (continued)
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
36-29 F Me CH2CF3 — 0 CF2 0 0 Oil
36-30 F Me CH2CF3 — 0 CF2 0 1 104-106
36-31 F Me CH2CF3 — 0 CHMe 0 0
36-32 F Me CH2CF3 — 0 CHMe 0 1
36-33 F Me CH2CF3 — 0 CHCF3 0 0
36-34 F Me CH2CF3 — 0 CHCF3 0 1
36-35 F Me CH2CF3 — 0 CMe2 0 0
36-36 F Me CH2CF3 — 0 CMe2 0 1
36-37 F Me CH2CF3 — 0 C(CF3) 2 0 0
36-38 F Me CH2CF3 — 0 C(CF3) 2 0 1
36-39 F Me CH2CF3 3-F 0 CF2 0 0
36-40 F Me CH2CF3 3-F 0 CF2 0 1
36-41 F Me CH2CF3 4-F 0 CF2 0 0
36-42 F Me CH2CF3 4-F 0 CF2 0 1
36-43 F Me CH2CF3 3-CI 0 CF2 0 0
36-44 F Me CH2CF3 3-CI 0 CF2 0 1
36-45 F Me CH2CF3 4-CI 0 CF2 0 0
36-46 F Me CH2CF3 4-CI 0 CF2 0 1
36-47 F Me CH2CF3 3-CF3 0 CF2 0 0
36-48 F Me CH2CF3 3-CF3 0 CF2 0 1
36-49 F Me CH2CF3 4-CF3 O CF2 0 0
36-50 F Me CH2CF3 4-CF3 0 CF2 0 1
36-51 H Me CH2CF3 — 0 CF2 0 0
36-52 H Me CH2CF3 — 0 CF2 0 1
36-53 Me Me CH2CF3 — 0 CF2 0 0
36-54 Me Me CH2CF3 — 0 CF2 0 1
36-55 CI Me CH2CF3 — 0 CF2 0 0
36-56 CI Me CH2CF3 — 0 CF2 0 1
TABLE 37 (r4)
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
37-1 F Me CH2CF3 — 0 CH2 CH2 0
37-2 F Me CH2CF3 — 0 CH2 CH2 1
37-3 F Me CH2CF3 — S CH2 CH2 0
37-4 F Me CH2CF3 — S CH2 CH2 1
37-5 F Me CH2CF3 — SO CH2 CH2 0
37-6 F Me CH2CF3 — SO CH2 CH2 1
37-7 F Me CH2CF3 — SO2 CH2 CH2 0
37-8 F Me CH2CF3 SO2 CH2 CH2 1
37-9 F Me CH2CF3 — CH2 O CH2 0
37-10 F Me CH2CF3 — CH2 O CH2 1
37-1 F Me CH2CF3 — CH2 S CH2 0
37-12 F Me CH2CF3 — CH2 S CH2 1
37-13 F Me CH2CF3 — CH2 SO CH2 0
37-14 F Me CH2CF3 — CH2 SO CH2 1
37-15 F Me CH2CF3 — CH2 SO2 CH2 0
37-16 F Me CH2CF3 — CH2 SO2 CH2 1
37-17 F Me CH2CF3 — CH2 CH2 O 0
37-18 F Me CH2CF3 — CH2 CH2 O 1
37-19 F Me CH2CF3 — CH2 CH2 S 0
37-20 F Me CH2CF3 — CH2 CH2 S 1
37-21 F Me CH2CF3 — CH2 CH2 SO 0
37-22 F Me CH2CF3 — CH2 CH2 SO 1
37-23 F Me CH2CF3 — CH2 CH2 SO2 0
37-24 F Me CH2CF3 — CH2 CH2 SO2 1
37-25 F Me CH2CF3 — O CH2 O 0 Oil
37-26 F Me CH2CF3 — O CH2 O 1 Oil
37-27 F Me CH2CF3 — O CHF O 0
37-28 F Me CH2CF3 — O CHF O 1
Figure imgf000077_0001
Figure imgf000078_0001
TABLE 37 (continued)
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
37-85 F H CH2CF3 — O CF2 O 0 Oil
37-86 F H CH2CF3 — O CF2 O 1 100-101
37-87 F F CH2CF3 — O CF2 O 0 Oil
37-88 F . F CH2CF3 — O CF2 O 1 98-99
37-89 F CI CH2CF3 — O CF2 O 0 53-54
37-90 F CI CH CF3 — O CF2 O 1 142-143
37-91 F Et CH2CF3 — O CF2 O 0
37-92 F Et CH2CF3 — O CF2 O 1
37-93 F CF3 CH2CF3 — O CF2 O 0
37-94 F CF3 CH2CF3 — O CF2 O 1
37-95 F OMe CH2CF3 — . O CF2 O 0
37-96 F OMe CH2CF3 — O CF2 O 1
37-97 F CN CH2CF3 — O CF2 O 0
37-98 F CN CH2CF3 — O CF2 O 1
37-99 CI H CH2CF3 — O CF2 O 0 61-63
37-100 CI H CH2CF3 — O CF2 O 1 132-133
37-101 CI F CH2CF3 — O CF2 O 0 Oil
37-102 CI F CH2CF3 — O CF2 O 1 133-134
37-103 CI CI CH2CF3 — O CF2 O 0 Oil
37-104 CI CI CH2CF3 — O CF2 O 1 173-174
37-105 CI Et CH2CF3 — O CF2 O 0
37-106 CI Et CH2CF3 — O CF2 O 1
37-107 CI CF3 CH2CF3 — O CF2 O 0
37-108 CI CF3 CH2CF3 — O CF2 O 1
37-109 CI OMe CH2CF3 — O CF2 O 0 Oil
37- 0 CI OMe CH2CF3 — O CF2 O 1 169-170
37-111 CI CN CH2CF3 — O CF2 O 0
37-112 CI CN CH2CF3 — O CF2 O 1
TABLE 37 (continued)
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
37-113 Me H CH2CF3 — O CF2 O 0
37-114 Me H CH2CF3 — O CF2 O 1
37-115 Me F CH2CF3 — O CF2 O 0 Oil
37-116 Me F CH2CF3 — O CF2 O 1 139-140
37-117 Me CI CH2CF3 — O CF2 O 0 Oil
37-118 Me CI CH2CF3 — O CF2 O 1 166-167
37-119 Me Et CH2CF3 — O CF2 O 0
37-120 Me Et CH2CF3 — O CF2 O 1
37-121 Me CF3 CH2CF3 — O CF2 O 0
37-122 Me CF3 CH2CF3 — O CF2 O 1
37-123 Me OMe CH2CF3 — O CF2 O 0
37-124 Me OMe CH2CF3 — O CF2 O 1
37-125 Me CN CH2CF3 — O CF2 O 0
37-126 Me CN CH2CF3 — O CF2 O 1
37-127 OMe H CH2CF3 — O CF2 O 0
37-128 OMe H CH2CF3 — O CF2 O 1
37-129 OMe F CH2CF3 — O CF2 O 0 70-71
37-130 OMe F CH2CF3 — O CF2 O 1 99-100
37-131 OMe CI CH2CF3 — O CF2 O 0
37- 32 OMe CI CH2CF3 — O CF2 O 1
37-133 OMe Me CH2CF3 — O CF2 O 0
37-134 OMe Me CH2CF3 — O CF2 O 1
37- 35 OMe CF3 CH2CF3 — O CF2 O 0
37-136 OMe CF3 CH2CF3 — O CF2 O 1
37-137 OMe OMe CH2CF3 — O CF2 O 0
37-138 OMe OMe CH2CF3 — O CF2 O 1
37-139 OMe CN CH2CF3 — O CF2 O 0
37-140 OMe CN CH2CF3 — O CF2 O 1
Figure imgf000081_0001
Figure imgf000082_0001
Figure imgf000083_0001
TABLE 38
Figure imgf000084_0001
Physical
No. R1 R2 R3 R4 B5 B6 B7 n
properties
38-1 F Me CH2CF3 — CH2 CH2 CH2 0
38-2 F Me CH2CF3 — CH2 CH2 CH2 1
38-3 F Me CH2CF3 — 0 CH2 0 0 Oil
38-4 F Me CH2CF3 — 0 CH2 0 i 120-123
38-5 F Me CH2CF3 — 0 CHF 0 0
38-6 F Me CH2CF3 — 0 CHF 0 1
38-7 F Me CH2CF3 — 0 CF2 0 0
38-8 F Me CH2CF3 — - 0 CF2 0 1
38-9 F Me CH2CF3 ■— 0 CHMe 0 0
38-10 F Me CH2CF3 — 0 CHMe 0 1
38-11 F Me CH2CF3 — 0 CHCF3 0 0
38-12 F Me CH2CF3 — 0 CHCF3 0 1
38-13 F Me CH2CF3 — 0 CMe2 0 0
38-14 F Me CH2CF3 — 0 CMe2 0 1
38-15 F Me CH2CF3 — 0 C(CF3)2 0 0
38-16 F Me CH2CF3 — 0 C(CF3)2 0 1
38-17 H Me CH2CF3 — 0 CH2 0 0
38-18 H Me CH2CF3 — 0 CH2 0 1
38-19 H Me CH2CF3 — 0 CF2 0 0
38-20 H Me CH2CF3 — O CF2 0 1
38-21 Me Me CH2CF3 — 0 CH2 0 0
8-22 Me Me CH2CF3 — 0 CH2 0 1
38-23 Me Me CH2CF3 — 0 CF2 0 0
38-24 Me Me CH2CF3 — 0 CF2 0 1
8-25 CI Me CH2CF3 — 0 CH2 0 0
8-26 CI Me CH2CF3 — 0 CH2 0 1
8-27 CI Me CH2CF3 — 0 CF2 0 0
8-28 CI Me CH2CF3 — 0 CF2 0 1 TABLE 39
Figure imgf000085_0001
Physical
No. R1 R2 R3 R4 E5 E6 E7 E8 n
properties
39-1 F Me CH2CF3 — CH2 CH2 CH2 CH2 0
39-2 F Me CH2CF3 — CH2 CH2 CH2 CH2 1
39-3 F Me CH2CF3 — 0 CH2 CH2 CH2 0
39-4 F Me CH2CF3 — 0 CH2 CH2 CH2 1
39-5 F Me CH2CF3 — 0 CH2 0 CH2 0
39-6 F Me CH2CF3 — 0 CH2 0 CH2 1
39-7 F Me CH2CF3 — 0 CF2 0 CH2 0
39-8 F Me CH2CF3 — 0 CF2 0 CH2 1
39-9 F Me CH2CF3 — 0 CH2 0 CF2 0
39-10 F Me CH2CF3 — 0 CH2 0 CF2 1
39-11 F Me CH2CF3 — 0 CF2 0 CF2 0
39-12 F Me CH2CF3 — 0 CF2 0 CF2 1
39-13 F Me CH2CF3 — 0 CH2 CH2 0 0 Oil
39-14 F Me CH2CF3 — 0 CH2 CH2 0 1 Oil
39-15 F Me CH2CF3 — 0 CF2 CF2 0 0
39-16 F Me CH2CF3 — 0 CF2 CF2 0 1
39-17 F Me CH2CF3 — CH2 CH2 CH2 0 0
39-18 F Me CH2CF3 — CH2 CH2 CH2 0 1
39-19 F Me CH2CF3 — CH2 0 CH2 0 0
39-20 F Me CH2CF3 — CH2 0 CH2 0 1
39-21 F Me CH2CF3 — CF2 0 CH2 0 0
39-22 F Me CH2CF3 — CF2 0 CH2 0 1
39-23 F Me CH2CF3 — CH2 0 CF2 0 0
39-24 F Me CH2CF3 — CH2 0 CF2 0 1
39-25 F Me CH2CF3 — CF2 0 CF2 0 0
39-26 F Me CH2CF3 — CF2 0 CF2 0 1
39-27 F Me CH2CF3 — S CH2 CH2 CH2 0
39-28 F Me CH2CF3 — S CH2 CH2 CH2 1 TABLE 40 (r4)
Physical
No. R1 R2 R3 R4 E5 E6 E7 E8 n
properties
40-1 F Me CH2CF3 — CH2 CH2 CH2 CH2 0
40-2 F Me CH2CF3 — CH2 CH2 CH2 CH2 1
40-3 F Me CH2CF3 — 0 CH2 CH2 CH2 0
40-4 F Me CH2CF3 — 0 CH2 CH2 CH2 1
40-5 F Me CH2CF3 — 0 CH2 0 CH2 0
40-6 F Me CH2CF3 — 0 CH2 0 CH2 1
40-7 F Me CH2CF3 — 0 CF2 0 CH2 0
40-8 F Me CH2CF3 — 0 CF2 0 CH2 1
40-9 F Me CH2CF3 — 0 CH2 0 CF2 0
40-10 F Me CH2CF3 — 0 CH2 0 CF2 1
40-11 F Me CH2CF3 — 0 CF2 0 CF2 0
40-12 F Me CH2CF3 — 0 CF2 0 CF2 1
40-13 F Me CH2CF3 — 0 CH2 CH2 0 0 Oil
40-14 F Me CH2CF3 — 0 CH2 CH2 0 1 81 -83
40-15 F Me CH2CF3 — 0 CF2 CF2 0 0
40-16 F Me CH2CF3 — 0 CF2 CF2 0 1
40-17 F Me CH2CF3 — CH2 CH2 CH2 0 0
40-18 F Me CH2CF3 — CH2 CH2 CH2 0 1
40-19 F Me CH2CF3 — CH2 0 CH2 0 0
40-20 F Me CH2CF3 — CH2 0 CH2 0 1
40-21 F Me CH2CF3 — CF2 0 CH2 0 0
0-22 F Me CH2CF3 — CF2 0 CH2 0 1
0-23 F Me CH2CF3 — CH2 0 CF2 0 0
0-24 F Me CH2CF3 — CH2 0 CF2 0 1
0-25 F Me CH2CF3 — CF2 0 CF2 0 0
0-26 F Me CH2CF3 — CF2 0 CF2 0 1
0-27 F Me CH2CF3 — S CH2 CH2 CH2 0
0-28 F Me CH2CF3 — S CH2 CH2 CH2 1
Figure imgf000087_0001
TABLE 41 (continued)
Physical
No. R1 R2 R3 R4 G5 G6 G7 n
properties
41-29 F Me CH2CF3 4-NO2 N 0 N 0 119-121
41-30 F Me CH2CF3 4-NO2 N 0 N 1
41-31 F Me CH CF3 3-F N S N 0 47-49
41-32 F Me CH2CF3 3-F N S N 1 76-80
41-33 F Me CH2CF3 3-CI N S N 0 50-52
41-34 F Me CH2CF3 3-CI N S N 1 50-55
41-35 F Me CH2CF3 4-Br N S N 0 95-97
41-36 F Me CH2CF3 4-Br N S N 1 129-131
41-37 Me Me CH2CF3 4-Br N S N 0 82-83
41-38 Me Me CH2CF3 4-Br N S N 1 212-215
Figure imgf000089_0001
TABLE 42 (continued)
Physical
No. R1 R2 R3 R4 G5 G6 G7 n
properties
42-29 F Me CH2CF3 4-F N 0 N 0 Oil
42-30 F Me CH2CF3 4-F N 0 N 1
42-31 F Me CH2CF3 4-CI N 0 N 0 31 -35
42-32 F Me CH2CF3 4-CI N 0 N 1 97-99
42-33 F Me CH2CF3 4-Me N 0 N 0 Oil
42-34 F Me CH2CF3 4-Me N 0 N 1 103-105
42-35 F Me CH2CF3 4-CF3 N 0 N 0 64-66
42-36 F Me CH2CF3 4-CF3 N 0 N 1 Oil
42-37 F Me CH2CF3 4-F N S N 0 75-77
42-38 F Me CH2CF3 4-F N S N 1 92-94
42-39 F Me CH2CF3 4-CI N . S N 0 Oil
42-40 F Me CH2CF3 4-CI N S N 1 102-105
42-41 F Me CH2CF3 4-Br N S N 0 Oil
42-42 F Me CH2CF3 4-Br N S N 1 108-1 10
TABLE 43
Figure imgf000091_0001
Figure imgf000092_0001
Figure imgf000093_0001
Figure imgf000094_0001
Figure imgf000095_0001
Figure imgf000096_0001
Figure imgf000097_0001
Figure imgf000098_0001
Figure imgf000099_0001
Figure imgf000100_0001
TABLE 53
Physical
No. R1 R2 R3 R4 L5 L6 n
properties
53-1 F Me CH2CF3 — N 0 0
53-2 F Me CH2CF3 — N 0 1
53-3 F Me CH2CF3 — N s 0
53-4 F Me CH2CF3 — N s 1
53-5 F Me CH2CF3 — CH 0 0
53-6 F Me CH2CF3 — CH 0 1
53-7 F Me CH2CF3 1-F CH 0 0
53-8 F Me CH2CF3 1-F CH 0 1
53-9 F Me CH2CF3 2-F CH 0 0
53-10 F Me CH2CF3 2-F CH 0 1
53-11 F Me CH2CF3 1-CI CH 0 0
53-12 F Me CH2CF3 1-CI CH 0 1
53-13 F Me CH2CF3 1-Me CH 0 0
53-14 F Me CH2CF3 1-Me CH 0 1
53-15 F Me CH2CF3 I -CF3 CH 0 0
53-16 F Me CH2CF3 I-CF3 CH 0 1
53-17 F Me CH2CF3 — CH s 0
53-18 F Me CH2CF3 — CH s 1
53-19 F Me CH2CF3 1-F CH s 0
53-20 F Me CH2CF3 1-F CH s 1
53-21 F Me CH2CF3 2-F CH s 0
53-22 F Me CH2CF3 2-F CH s 1
53-23 F Me CH2CF3 1-CI CH s 0
53-24 F Me CH2CF3 1-CI CH s 1
53-25 F Me CH2CF3 1-Me CH s 0
53-26 F Me CH2CF3 1-Me CH s 1
3-27 F Me CH2CF3 I -CF3 CH s 0
53-28 F Me CH2CF3 I -CF3 CH s 1
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
TABLE 56
Figure imgf000105_0001
Figure imgf000106_0001
Figure imgf000107_0001
Figure imgf000108_0001
Figure imgf000109_0001
TABLE 57
Figure imgf000110_0001
Now, Test Examples will be described.
TEST EXAMPLE 1
Test on adults of two-spotted spider mite ( Tetranychus urticae )
An insecticidal solution was prepared to bring the concentration of the compound of the present invention to 50 ppm. A kidney bean having only one primordial leaf left, was transplanted to a pot ( diameter: 8 cm, height: 7 cm ), and 20 adults of two-spotted spider mite were released thereon. Together with the kidney bean leaf, they were dipped in the above insecticidal solution for about 5 seconds, dried in air and then left in a constant temperature chamber at 25°C with lightening. On the second or third day after the treatment, the number of dead adults were counted, and the mortality of adults was calculated by the following equation. Adults that dropped from the leaf or were moribund were included in the number of dead. The test was carried out with respect to the above-mentioned Compound Nos. 1-1 , 1 -24, 1 -25, 3-1 , 4-1 , 4-2, 4-5, 4- 6, 4-7, 4-8, 4-11 , 4-13, 4-14, 4-15, 4-17, 4-18, 4-19, 4-20, 4-23, 4-29, 4-75, 4-77, 4-79,
4- 80, 4-81 , 4-85, 4-86, 4-87, 4-89, 4-93, 4-94, 4-95, 4-96, 5-1 , 5-2, 5-5, 5-6, 5-9, 5-10,
5- 11 , 5-15, 5-17, 5-25, 5-75, 5-86, 5-87, 5-88, 5-89, 5-91 , 5-93, 5-95, 5-99, 5-105, 5- 106, 5-107, 5-108, 5-109, 5-112, 6-1 , 6-11 , 6-28, 6-30, 6-31 , 6-34, 7-1 , 9-1 , 9-55, 10-1 , 10-15, 12-1 , 12-2, 12-75, 13-1 , 13-2, 13-5, 13-11 , 13-15, 13-18, 13-19, 13-20, 13-75, 13-76, 13-85, 13-86, 14-1 , 15-1 , 16-27, 17-1 , 18-1 , 18-15, 18-29, 18-30, 20-1 , 20-2, 22-1 , 22-2, 24-1 , 24-2, 24-27, 25-1 , 25-3, 25-4, 25-9, 25-10, 25-27, 25-29, 25-31 , 27-1 , 27-29, 27-30, 28-1 , 31-1 , 31-2, 31 -27, 31-29, 31-30, 31-31 , 31-32, 31 -45, 31 -49, 31 - 50, 31-55, 31 -56, 31-57, 31 -58, 31 -59, 31 -60, 31 -65, 31 -67, 31 -68, 31 -69, 31 -70, 32-1 , 32-2, 32-3, 32-4, 32-9, 32-27, 32-29, 32-30, 33-1 , 34-1 , 35-1 , 36-25, 36-26, 36-29, 36-
30, 37-25, 37-26, 37-29, 37-30, 37-35, 37-36, 37-51 , 37-52, 37-53, 37-54, 37-55, 37- 56, 37-57, 37-58, 37-59, 37-60, 37-65, 37-66, 37-67, 37-68, 37-75, 37-76, 37-85, 37- 86, 37-87, 37-88, 37-89, 37-90, 37-99, 37-100, 37-101 , 37-102, 37-103, 37-104, 37- 110, 37-117, 37-141 , 37-143, 37-144, 37-145, 37-146, 37-147, 37-148, 37-149, 37-150,
37- 151 , 37-152, 37-157, 37-159, 37-160, 37-162, 37-163, 37-164, 37-167, 37-168, 37- 169, 37-170, 37-171 , 37-172, 37-177, 37-178, 37-189, 37-190, 37-191 , 37-192, 37- 193, 37-194, 37-205, 37-206, 37-207, 37-208, 37-215, 37-216, 37-223, 37-224, 38-3,
38- 4, 39-13, 41 -9, 41 -21 , 41 -22, 41 -29, 41 -31 , 41 -32, 41 -33, 41-35, 41 -37, 42-9, 42- 10, 42-13, 42-14, 42-15, 42-16, 42-17, 42-18, 42-19, 42-20, 42-21 , 42-22, 42-29, 42-
31 , 42-32, 42-33, 42-34, 42-35, 42-36, 42-37, 42-38, 42-39, 43-9, 43-10, 43-21 , 43-22, 44-15, 44-25, 46-15, 48-1 , 50-1 , whereby all compounds showed a mortality of adults of at least 90%.
Mortality of adults (%) = (The number of dead two-spotted spider mites/The number of treated two-spotted spider mites ) x 100
TEST EXAMPLE 2
Test on controlling effects against brown planthopper (Nilaparvata lugens)
Rice seedling was dipped for about 10 seconds in an insecticidal solution adjusted to bring the concentration of the compound of the present invention to 200 ppm and then dried in air, its root was wrapped with a wet absorbent cotton, and the seedling was put into a test tube. Then, 20 second-third instar nymphs of brown planthopper were released therein, and the test tube was covered with a gauze and left in a constant temperature chamber at 25°C with lightening. On the 5th day after the release, the number of dead nymphs were counted, and the mortality was calculated by the following equation.
The test was carried out with respect to the above-mentioned Compound Nos. 3- 1 , 4-17, 4-85, 6-1 , 6-11 , 6-28, 6-34, 7-1 , 20-1 , 24-1 , 24-27, 25-3, 25-27, 36-25, 36-26, 37-25, 37-29, 37-30, 37-51 , 37-52, 37-65, 37-76, 37-85, 37-87, 37-88, 37-89, 37-90, 37-143, 37-144, 37-145, 37-146, 37-147, 37-152, 37-159, 37-160, 37-162, 37-163, 37- 164, 37-167, 37-193, 37-194, 37-205, 38-3, 38-4, 41 -9, 41 -10, 41 -21 , 41 -31 , 42-9, 42- 10, 42-13, 42-15, 42-17, 42-29, 42-31 , 42-32, 42-33, 42-34, 42-35, 43-9, 43-10, 46-15, 48-1 , 50-1 , whereby all compounds showed a mortality of at least 90%.
Mortality (%)=(The number of dead insects/The number of released insects)x100
Now, Formulation Examples are described below.
FORMULATION EXAMPLE 1
(1 ) Compound of the present invention 20 parts by weight
(2) Clay 70 parts by weight
(3) White carbon 5 parts by weight
(4) Sodium polycarboxylate 3 parts by weight
(5) Sodium alkylnaphthalene sulfonate 2 parts by weight
The above components are uniformly mixed to obtain a wettable powder.
FORMULATION EXAMPLE 2
(1) Compound of the present invention 5 parts by weight (2) Talc .60 parts by weight
(3) Calcium carbonate 34.5 parts by weight
(4) Liquid paraffin 0.5 part by weight
The above components are uniformly mixed to obtain a dust.
FORMULATION EXAMPLE 3
(1) Compound of the present invention 20 parts by weight
(2) N,N-dimethylacetamide 20 parts by weight
(3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight
(4) Calcium dodecylbenzene sulfonate 2 parts by weight
(5) Xylene 48 parts by weight
The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.
FORMULATION EXAMPLE 4
(1) Clay 68 parts by weight
(2) Sodium lignin sulfonate 2 parts by weight
(3) Polyoxyethylenealkylaryl sulfate 5 parts by weight
(4) White carbon 25 parts by weight
The mixture of the above components is mixed with compound of the present invention in a weight ratio of 4:1 to obtain a wettable powder.
FORMULATION EXAMPLE 5
(1) Compound of the present invention 50 parts by weight
(2) Sodium alkylnaphthalene sulfonate condensation product of formaldehyde 2 parts by weight
(3) Silicone oil 0.2 part by weight
(4) Water 47.8 parts by weight
The above components are uniformly mixed and pulverized to obtain a base liquid, and
(5) Sodium polycarboxylate 5 parts by weight
(6) Anhydrous sodium sulfate 42.8 parts by weight
are added, and the mixture is uniformly mixed, granulated and dried to obtain water- dispersible granules.
FORMULATION EXAMPLE 6
(1 ) Compound of the present invention 5 parts by weight
(2) Polyoxyethyleneoctylphenyl ether 1 part by weight
(3) Polyoxyethylene alkyl ether phosphoric acid ester 0.1 part by weight
(4) Granular calcium carbonate 93.9 parts by weight
The above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules.
FORMULATION EXAMPLE 7
(1 ) Compound of the present invention 2.5 parts by weight
(2) N,N-dimethylacetamide 2.5 parts by weight
(3) Soybean oil 95.0 parts by weight
The above components are uniformly mixed and dissolved to obtain an ultra low volume formulation.
FORMULATION EXAMPLE 8
(1) Compound of the present invention 10 parts by weight
(2) Diethylene glycol monoethyl ether 80 parts by weight 1 ^ ^
(3) Polyoxyethylenealkyl ether 10 parts by weight
The above components are uniformly mixed to obtain a soluble concentrate.
The entire disclosure of Japanese Patent Application No. 2011 -140463 filed on June 24, 2011 including specification, claims, drawings and summary is incorporated herein by reference in its entirety.

Claims

CLAIMS:
1. A compound represented by the formula (I) or its salt:
Figure imgf000114_0001
(I)
wherein each of R1 and R2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy or cyano; R3 is alkyl or haloalkyl; n is an integer of 0 or 1 ; and Q is any of the following formulae [Q-1] to [Q-6]:
Figure imgf000114_0002
[Q- 1 ] [Q-2] [Q-3]
Figure imgf000114_0003
[Q-4] [Q-5] [Q-6]
wherein each of A1 to A8 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of A1 to A8 is CH, it may be substituted by R4, and among A1 to A8, the number of groups which may be nitrogen atoms, is from 0 to 3; each of B1 to B4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of B1 to B4 is CH, it may be substituted by R4, and among B1 to B4, the number of groups which may be nitrogen atoms, is from 0 to 1 ; each of B5 to B7 which may be the same or different from one another, is C(R5)(R6), an oxygen atom, a sulfur atom, SO or SO2; each of E1 to E4 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of E1 to E4 is CH, it may be substituted by R4, and among E1 to E4, the number of groups which may be nitrogen atoms, is from 0 to 1 ; each of E5 to E8 which may be the same or different from one another, is C(R5)(R6), an oxygen atom, a sulfur atom, SO or SO2; each of G1 to G5 and G7 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of G1 to G5 and G7 is CH, it may be substituted by R4, and among G1 to G5 and G7, the number of groups which may be nitrogen atoms, is from 0 to 3; G6 is an oxygen atom or a sulfur atom; each of J1 to J6 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of J1 to J6 is CH, it may be substituted by R4, and among J1 to J6, the number of groups which may be nitrogen atoms, is from 0 to 2; each of L1 to L5 which may be the same or different from one another, is CH or a nitrogen atom, provided that when any of L1 to L5 is CH, it may be substituted by R4, and among L1 to L5, the number of groups which may be nitrogen atoms, is from 0 to 2; L6 is an oxygen atom or a sulfur atom; R4 is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, COR7, CO2R7, N(R8)COR7, N(R8)C02R7, NR9R10, CONR9R10, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyi, alkylsulfonyl, haloalkylsulfonyl, phenyl which may be substituted by R11, or pyridyl which may be substituted by R11, provided that when the number of R4 is two or more, the plurality of R4 may be the same or different; each of R5 and R6 which are independent of each other, is a hydrogen atom, a halogen atom, alkyi or haloalkyi, provided that when the number of R5 or R6 is two or more, the plurality of R5 or R6 may be the same or different; each of R7, R8, R9 and R10 which are independent of one another, is a hydrogen atom or alkyi; when R9 and R10 are alkyi, R9 and R10 may, together with the nitrogen atom to which they are bonded, form a 5- or 6-membered ring; and R11 is a halogen atom, alkyi, haloalkyi, alkoxy or haloalkoxy.
2. The compound or its salt according to Claim 1 , wherein Q is any of the formulae [Q-1] to [Q-5].
3. The compound or its salt according to Claim 1 , wherein Q is the formula [Q-1], [Q- 2] or [Q-4].
4. The compound or its salt according to Claim 1 , wherein R1 is a hydrogen atom, a halogen atom, alkyi or alkoxy; R2 is a hydrogen atom, a halogen atom, alkyi or alkoxy; R3 is alkyi or haloalkyi; and Q is the formula [Q-1], [Q-2] or [Q-4].
5. The compound or its salt according to Claim 1 , wherein Q is the formula [Q-1] or
[Q-2].
6. The compound or its salt according to Claim 1 , wherein R1 is a hydrogen atom, a halogen atom, alkyi or alkoxy; R2 is a hydrogen atom, a halogen atom, alkyi or alkoxy; R3 is alkyi or haloalkyi; and Q is the formula [Q-1 ] or [Q-2].
7. A compound represented by the formula (II):
Figure imgf000115_0001
(Π)
wherein X is a bromine atom; -B(OH)2 or pinacolatoboranyl; n is an integer of 0 or 1 ; each of R1 and R2 which are independent of each other, is a hydrogen atom, a halogen atom, alkyi, haloalkyi, alkoxy, haloalkoxy or cyano; R3 is alkyi or haloalkyi, provided that a case wherein R1 is a hydrogen atom or a fluorine atom, R2 is methyl, and R3 is trifluoroethyl, is excluded.
8. The compound according to Claim 7, wherein R1 is a fluorine atom, a chlorine atom or methyl; and R2 is a chlorine atom or methyl.
9. The compound according to Claim 7 or 8, wherein n is 0; and R3 is trifluoroethyl, trifluoropropyl, difluoroethyl or n-propyl.
10. A pesticide containing the compound or its salt as defined in Claim 1 , as an active ingredient.
11. An insecticide, miticide, nematicide or soil pesticide containing the compound or its salt as defined in Claim 1 , as an active ingredient.
12. An insecticide or miticide containing the compound or its salt as defined in Claim 1 , as an active ingredient.
13. A method for controlling pests, which comprises applying an effective amount of the compound or its salt as defined in Claim 1 thereto.
14. A method for controlling insects, mites, nematodes or soil pests, which comprises applying an effective amount of the compound or its salt as defined in Claim 1 thereto.
15. A method for controlling insects or mites, which comprises applying an effective amount of the compound or its salt as defined in Claim 1 thereto.
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