WO2015125858A1 - Composé hétéro-aryle et ses applications - Google Patents

Composé hétéro-aryle et ses applications Download PDF

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WO2015125858A1
WO2015125858A1 PCT/JP2015/054597 JP2015054597W WO2015125858A1 WO 2015125858 A1 WO2015125858 A1 WO 2015125858A1 JP 2015054597 W JP2015054597 W JP 2015054597W WO 2015125858 A1 WO2015125858 A1 WO 2015125858A1
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group
substituted
unsubstituted
groups
compound
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PCT/JP2015/054597
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Japanese (ja)
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光 青山
麻記 松井
隆太郎 清田
花井　大輔
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日本曹達株式会社
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Priority claimed from JP2014084845A external-priority patent/JP2017078025A/ja
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Publication of WO2015125858A1 publication Critical patent/WO2015125858A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to heteroaryl compounds, pest control agents, insecticides or acaricides, and ectoparasite control agents. More specifically, the present invention relates to a heteroaryl compound that has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially, and a pest containing this as an active ingredient
  • the present invention relates to a control agent, an insecticide or acaricide, or an ectoparasite control agent.
  • Patent Document 1 describes a 2,6-dichloro-4-pyridinemethanol compound. This compound appears to have an excellent effect in controlling various plant diseases caused by phytopathogenic viruses, bacteria and filamentous fungi.
  • Patent Document 2 describes a pyridylpyridine compound. This compound has an effect as an agricultural and horticultural fungicide. In order to put such compounds into practical use as agricultural chemicals, they are not only sufficiently effective but also resistant to drug resistance, do not cause phytotoxicity or soil contamination on plants, and have low toxicity to livestock and fish. Etc. are required.
  • An object of the present invention is to provide a heteroaryl compound that is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized advantageously industrially, and effectively It is to provide a pest control agent, insecticide or acaricide, or ectoparasite control agent contained as a component.
  • R 1 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a C1-6 alkoxyC1-6 haloalkyl group.
  • X 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C1-6 alkoxy group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1 ⁇ 6 alkylamino groups, unsubstituted or substituted C1-6 alkylthio groups, unsubstituted or substituted C1-6 alkylsulfinyl groups, unsubstituted or substituted C1-6 alkylsulfonyl groups, Substituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10a Lumpur group, an unsubstituted or 3-6 membered heterocyclic group
  • n represents the number of X 1 and is an integer of 0-2. When m is 2 or more, X 1 may be the same as or different from each other.
  • B 1 , B 3 , and B 6 each independently represent a carbon atom or a nitrogen atom.
  • R 2 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted or unsubstituted C1-10 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C1-6 alkylcarbonyl group, carboxyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, amino group, unsubstituted or substituted C1-6 alkylamino group, aminocarbonyl group, unsubstituted Or a substituted C1-6 alkylaminocarbonyl group, mercapto group, unsubstituted or substituted group Having C1-6 alkylthio group, unsubsti
  • X 2 may be the same as or different from each other.
  • B 5 represents a carbon atom or a nitrogen atom.
  • Z represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by NR 3 .
  • R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, formyl Group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, or cyano group Indicates.
  • A represents an unsubstituted or substituted C1-6 alkylene group.
  • a pest control agent comprising at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.
  • An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compound according to [1] and a salt thereof.
  • An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] and a salt thereof.
  • the heteroaryl compound of the present invention can control pests that are problematic in crops and hygiene.
  • agricultural pests and mites can be effectively controlled.
  • ectoparasites that harm human livestock can be effectively controlled.
  • the heteroaryl compound of the present invention is a compound represented by formula (I-1) or formula (I-2) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I). .
  • the term “unsubstituted” means only a group serving as a mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
  • the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus.
  • the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
  • C1-6 indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Examples of groups that can be “substituents” are shown below. C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • An alkyl group Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc.
  • a C2-6 alkenyl group of C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;
  • a C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group;
  • a C4-8 cycloalkenyl group such as a 2-cyclopentenyl group, a 3-cyclohexenyl group, a 4-cyclooctenyl group;
  • a C6-10 aryl group such as a phenyl group or a naphthyl group;
  • a C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
  • Halogeno groups such as fluoro, chloro, bromo and iodo groups; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; A C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; A C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; A C1-6 haloalkoxy group such as a trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group; A C2-6 haloalkenyloxy group such as
  • a C1-6 alkylamino group such as a methylamino group, a dimethylamino group, a diethylamino group
  • C6-10 arylamino groups such as anilino group and naphthylamino group
  • a C6-10 aryl C1-6 alkylamino group such as a benzylamino group or a phenethylamino group
  • Formylamino group C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group
  • a C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group
  • An aminocarbonyl group; a C1-6 alkylaminocarbonyl group such as
  • a mercapto group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
  • a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
  • a C6-10 arylsulfinyl group such as a phenylsulfinyl group;
  • a C6-10 aryl C1-6 alkylsulfinyl group such as a benzylsulfinyl group, a phenethylsulfinyl group;
  • a C1-6 alkylsulfonyl group such as a methylsulfonyl
  • a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group;
  • a tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group; Cyano group; nitro group;
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • examples of the “substituent” include C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro group and the like.
  • the above “3- to 6-membered heterocyclic group” is a cyclic group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
  • Examples of the “3- to 6-membered heterocyclic group” include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclic group, and the like.
  • Examples of the 3- to 6-membered saturated heterocyclic group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like. be able to.
  • Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, etc. Can do.
  • Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
  • R 1 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a C1-6 alkoxyC1-6 haloalkyl group.
  • the “C1-6 alkyl group” in R 1 may be a straight chain or a branched chain as long as it has 3 or more carbon atoms.
  • Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • a fluoromethyl group a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2, 2,2-trifluoro-1-trifluoromethylethyl group, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, perfluorooctyl group, perfluorooctyl group A chloroocty
  • the “C1-6 haloalkoxy group” in R 1 includes a chloromethoxy group, a dichloromethoxy group, a difluoromethoxy group, a trichloromethoxy group, a trifluoromethoxy group, a 1-fluoroethoxy group, a 1,1-difluoroethoxy group, 2 , 2,2-trifluoroethoxy group, pentafluoroethoxy group, 2,2,3,4,4,4-hexafluoro-butoxy group, and the like.
  • Examples of the “C1-6 alkoxy C1-6 haloalkyl group” in R 1 include a methoxydifluoromethyl group and a 2,2,2-trifluoro-1-methoxy-1-trifluoromethylethyl group.
  • R 1 is preferably a C1-6 alkyl group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, and more preferably a C1-6 haloalkyl group.
  • X 1 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, unsubstituted or A substituted C1-6 alkoxy group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1 ⁇ 6 alkylamino groups, unsubstituted or substituted C1-6 alkylthio groups, unsubstituted or substituted C1-6 alkylsulfinyl groups, unsubstituted or substituted C1-6 alkylsulfonyl groups, Substituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C6-10a Lumpur group, an unsubstituted or 3-6 membere
  • the “C1-6 alkyl group” in X 1 may be a straight chain or a branched chain as long as it has 3 or more carbon atoms.
  • Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group.
  • C1-6 alkyl group having a substituent examples include C3-8 cycloalkyl C1-6 alkyl group such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group; fluoromethyl group, chloromethyl group, bromomethyl Group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2- Trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoro Hexyl
  • Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group; methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxy group C1-6 alkoxy C1-6 alkyl group such as methyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group; heteroaryloxy C1-6 alkyl group such as pyridin-2-yloxymethyl group A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
  • C2-6 alkenyl group for X 1 , a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl Group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • Specific examples of the “substituted C2-6 alkenyl group” include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group.
  • Examples of the “C2-6 alkynyl group” in X 1 include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl And a 1,1-dimethyl-2-butynyl group.
  • substituted C2-6 alkynyl group examples include C2-6 such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group and the like. Mention may be made of haloalkynyl groups.
  • the “C1-6 alkoxy group” in X 1 is a methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Specific examples of the “substituted C1-6 alkoxy group” include chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy.
  • Groups 2,2,2-trifluoroethoxy groups, pentafluoroethoxy groups, C1,6 haloalkoxy groups such as 2,2,3,4,4,4-hexafluoro-butoxy groups; methoxymethoxy groups, methoxyethoxy groups A C1-6 alkoxy group such as an ethoxymethoxy group; a C3-8 cycloalkyl C1-6 alkoxy group such as a cyclopropylmethyloxy group; a cyano C1-6 such as a cyanomethoxy group or a 2-cyanoethoxy group Alkoxy group; unsubstituted benzyloxy group, phenethyloxy group, etc.
  • a substituted C6-10 aryl C1-6 alkoxy group an unsubstituted or substituted 5- to 6-membered heterocyclic ring C1-6 such as a tetrahydrofuranylmethoxy group, an unsubstituted or substituted pyridylmethoxy group Alkoxy groups; cyano C1-6 alkoxy groups such as cyanomethoxy group and 2-cyanoethoxy group;
  • Examples of the substituent on the 5- to 6-membered heterocycle in the “C6-10 aryl C1-6 alkoxy group” and the “5- to 6-membered heterocycle C1-6 alkoxy group” include a C1-6 alkyl group and a C1-6 haloalkyl group.
  • C1-6 alkylcarbonyl group examples include an acetyl group and a propionyl group.
  • substituted C1-6 alkylcarbonyl group include C1-6 haloalkylacyl groups such as chloroacetyl group, trifluoroacetyl group and trichloroacetyl group.
  • Examples of the “C1-6 alkoxycarbonyl group” for X 1 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
  • C1-6 alkoxycarbonyl group having a substituent include C3-8 cycloalkyl C1-6 alkoxycarbonyl groups such as cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-cyclopropylethoxycarbonyl group; fluoromethoxycarbonyl group, chloromethoxy Carbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl
  • a C1-6 haloalkoxycarbonyl group such as a group;
  • Examples of the “C1-6 alkylamino group” for X 1 include a methylamino group, an n-butylamino group, a dimethylamino group, and a diethylamino group.
  • C1-6 alkylthio group examples include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like. be able to.
  • Specific examples of the “substituted C1-6 alkylthio group” include C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
  • C1-6 alkylsulfinyl group examples include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
  • Specific examples of the “substituted C1-6 alkylsulfinyl group” include C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
  • C1-6 alkylsulfonyl group examples include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
  • Specific examples of the “substituted C1-6 alkylsulfonyl group” include C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for X 1
  • Substituents on “group”, “C1-6 alkylamino group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, and “C1-6 alkylsulfonyl group” include C1-6 alkoxy groups A halogeno group, a cyano group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 3-6 membered heterocyclic group, and the like.
  • Examples of the “C3-8 cycloalkyl group” for X 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the “C6-10 aryl group” for X 1 may be monocyclic or polycyclic. In the polycyclic aryl group, if at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “C6-10 aryl group” include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like.
  • the “3- to 6-membered heterocyclic group” in X 1 is a cyclic group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring constituent atoms.
  • Examples of the “3- to 6-membered heterocyclic group” include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclic group, and the like.
  • Examples of the 3- to 6-membered saturated heterocyclic group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group (for details, see [1 , 3] dioxolanyl group), dioxanyl group (specifically, [1,3] dioxanyl group or [1,4] dioxanyl group).
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, and a triazolyl group (for details, [1,2,3] triazolyl group Or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,4] oxadiazolyl group or [1,3,4] oxadiazolyl group), thiadiazolyl group, tetrazolyl group, etc. Can do.
  • 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridanidyl group, and a triazinyl group.
  • Examples of the partially unsaturated 5-membered heterocyclic group include pyrrolinyl group, imidazolinyl group (dihydroimidazolyl group), pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group and the like.
  • Examples of the partially unsaturated 6-membered heterocyclic group include a thiopyranyl group, a 2H-pyridin-1-yl group, and a 4H-pyridin-1-yl group.
  • Substituents on the “C3-8 cycloalkyl group”, “C6-10 aryl group” and “3-6 membered heterocyclic group” in X 1 include C1-6 alkyl group, C1-6 haloalkyl group, C1-6 6 alkoxy group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro group and the like can be mentioned.
  • the “3- to 6-membered heterocyclic group” is preferably a 5- to 6-membered saturated heterocyclic group or a 5- to 6-membered heteroaryl group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • X 1 is preferably a halogeno group.
  • M is preferably an integer of 0 to 1.
  • B 1 , B 3 , and B 6 each independently represent a carbon atom or a nitrogen atom.
  • examples of the compound represented by formula (I-1) or formula (I-2) include compounds represented by formula (II) to formula (VI).
  • compounds represented by formula (II) to formula (V) are preferable.
  • R 2 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted or unsubstituted C1-10 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C1-6 alkylcarbonyl group, carboxyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, amino group, unsubstituted or substituted C1-6 alkylamino group, aminocarbonyl group, unsubstituted Or a substituted C1-6 alkylaminocarbonyl group, mercapto group, unsubstituted or substituted group Having C1-6 alkylthio group
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl group”, “C1-6 alkyl” in R 2 “Amino group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkylsulfonyl group”, “C3-8 cycloalkyl group”, “C6-10 aryl group”, “3—
  • Examples of the “6-membered heterocyclic group”, the “halogeno group”, and the group having a substituent in these groups include the same groups as those exemplified for X 1 above.
  • the “C1-10 alkoxy group” in R 2 and the group having a substituent in this group are the same as those exemplified in the above X 1 , n-heptyloxy group, n-octyloxy group, n-nonyloxy group And n-decyloxy group.
  • Examples of the “C2-6 alkenyloxy group” for R 2 include a vinyloxy group and an allyloxy group.
  • Examples of the “C2-6 alkynyloxy group” for R 2 include an ethynyloxy group, a 1-propynyloxy group, a 2-propynyloxy group, and the like.
  • Examples of the “C1-6 alkylaminocarbonyl group” in R 2 include a methylaminocarbonyl group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group, an i-propylaminocarbonyl group, a methyl- (i-propyl) aminocarbonyl group, and the like. Can do.
  • Examples of the “C1-6 alkylcarbonyloxy group” for R 2 include an acetyloxy group and a propionyloxy group.
  • the “C1-6 alkoxycarbonyloxy group” in R 2 includes a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, a t-butoxycarbonyl group.
  • An oxy group etc. can be mentioned.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-10 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for R 2 Group, C1-6 alkylamino group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C2-6 alkenyloxy group, C2-6 Substituents on “6 alkynyloxy group”, “C1-6 alkylaminocarbonyl group”, “C1-6 alkylcarbonyloxy group”, and “C1-6 alkoxycarbonyloxy group” include C1-6 alkoxy group, halogeno Group, cyano group, C3-8 cycloalkyl group, C6-10 aryl group, 3-6 membered heterocyclic group and the like.
  • Examples of the substituent on the “C3-8 cycloalkyl group”, “C6-10 aryl group”, and “3-6 membered heterocyclic group” in R 2 include a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group C1-6 alkoxy group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro group and the like.
  • the “3- to 6-membered heterocyclic group” is preferably a 5- to 6-membered saturated heterocyclic group or a 5- to 6-membered heteroaryl group.
  • R 2 an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C1-6 alkoxy group, Unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted
  • a C6-10 aryl group having a hydrogen atom or a halogeno group is preferred.
  • X 2 is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, an oxo group, an unsubstituted Substituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 represents an alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group.
  • n represents the number of X 2 and is an integer of 0-2. When n is 2 or more, X 2 may be the same as or different from each other.
  • C1-6 alkyl group C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” for X 2 ], “C1-6 alkylsulfonyl group”, and “halogeno group” and the group having a substituent in these groups may be the same as those exemplified for X 1 above.
  • X 2 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, or an unsubstituted or substituted C1-6 alkylthio group. Is preferred.
  • n is preferably an integer of 0 to 1.
  • B 5 represents a carbon atom or a nitrogen atom. Preferably, it is a nitrogen atom.
  • [Z, R 3 ] Z represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by NR 3 .
  • R 3 represents a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, formyl Or a C1-6 alkylcarbonyl group having an unsubstituted or substituted group, a C1-6 alkoxycarbonyl group having an unsubstituted or substituted group, or a C1-6 alkylsulfonyl group having an unsubstituted or substituted group.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl group”, and “C1-6” in R 3
  • Z an oxygen atom is preferable.
  • [A] A represents an unsubstituted or substituted C1-6 alkylene group.
  • Examples of the “C1-6 alkylene group” in A include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a propane-1,2-diyl group (ie, a propylene group), and the like.
  • Examples of the substituent on the “C1-6 alkylene group” include a C1-6 alkyl group and a cyano group.
  • the salt of the compound (I) according to the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt.
  • salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron and copper
  • salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
  • the salt of compound (I) can be obtained by a known method.
  • the heteroaryl compound of the present invention (hereinafter sometimes referred to as the present compound) is not particularly limited by its production method.
  • the salt of a compound can be obtained from a compound by a well-known method.
  • this invention compound can be obtained by the well-known manufacturing method described in the Example etc.
  • the compound of the present invention is excellent in controlling pests such as various agricultural pests and mites that affect plant growth.
  • the compound of the present invention is a highly safe compound because it has little phytotoxicity and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or an acaricide.
  • resistance to organophosphates and carbamates has been developed in many pests such as diamondback moth, leafhopper, leafhopper, and aphid, resulting in insufficient efficacy of these drugs. Is desired.
  • the compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains and further on mite-resistant strains of mites.
  • the compound of the present invention is excellent in the control effect of ectoparasites that are harmful to humans. In addition, it is a highly safe compound due to its low phytotoxicity and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an ectoparasite control agent.
  • the pest control agent or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
  • plants to be treated with the pest control agent of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, turf and the like. In that case, each part of these plants can also be processed. Examples of each part of the plant include leaves, stems, patterns, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings and the like. Further, improved varieties and varieties of these plants, cultivated varieties, and mutants, hybrids, and genetically modified organisms (GMO) can also be treated.
  • GMO genetically modified organisms
  • the pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application and the like in order to control various agricultural pests and mites.
  • Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis; (B) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella; (C) Carposinidae, for example, Carposina sasakii; (D) moths of the Craambidae family, for example, Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp.
  • Astragalus Ostrinia furnacalis
  • European corn borer Ostrinia nubilalis
  • Azuki bean Ostrinia scapulalis
  • Others Diatraea grandiosella
  • Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella
  • E Gelechiidae moths, for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella
  • G) moths of the family Gracillariidae for example, Caloptilia theivora, citrus moth (Phyllocnistis citrella), king moth (Phyllonorycter ringoniella);
  • H Hesperiidae butterflies, such as Par
  • Agrotis ipsilon, Agrotis segetum for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Seeds of the species (Heliothis spp.), Cottontail (Heliothis armigera), fake American tobacco (Heliothis v irescens); other, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, cenranga ps , Peridroma saucia, Soybean looper (Pseudoplusia includens), Trichoplusia ni; (M) Nolidae moths, eg, Misaria olinga (Earias insulana); (N) Pieridae butterflies, for example, Pieris s
  • (R) moths of the family Stahmopodidae for example, Stahmopoda needsssa
  • (T) Tortricidae moths for example, Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp .; for example, Archips spp.
  • Thysanoptera pests (a) from the Phlaeothripidae, for example, Ponticulothrips diospyrosi; (B) From the Thripidae family, for example, from Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; Other, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis;
  • Hemiptera pests Ceratomas (Archaeorrhyncha) (A) From the Delphacidae family, for example, the green planthopper (Laodelphax striatella), the green planthopper (Nilaparvata lugens), the black planthopper (Perkinsiella saccharicida), the white planthopper (Sogatella furcifera);
  • C Stink bug (Heteroptera)
  • A from the family Alydidae, for example, Riptortus clavatus
  • B from the family Coridae, for example, Cletus punctiger, Leptocorisa chinensis
  • C from the family Lygaeidae, for example, the American leaf beetle (Blissus leucopterus), the giant leaf beetle (Cavelerius saccharivorus), the leaf beetle (Togo hemipterus);
  • D From the Miridae family, for example, the black-headed turtle (Halticus insularis), the white-headed turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the naga-gumika turtle (Stenodema sibiricum), the tussidous moth ), Trigonotylus caelestialium;
  • E from the Pentatomidae family, for example, from the Nezara spp., Nezara antennata, Nezara viridula; , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Others, Dolycoris baccarum, Subtilus Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida; (F) from the family Pyrrhocoridae, for example, Dysdercus cingulatus; (G) from the family Rhopalidae, for example, Rhopalus msculatus; (H) from the family Scutelleridae, for example, Eurygaster integriceps; (I) from the family Tingidae, for example, Stephanitis nashi;
  • peach aphid Myzus persicae
  • myrtle aphid Myzus varians
  • pea beetle aphids Acyrthosiphon pisum
  • potato beetle aphids Aulacorthum solani
  • wheat aphids Brevicors Metopolophium dirhodum lettuce aphids
  • lettuce aphids Nasonovia ribis-nigri
  • hops aphids Phorodon humuli
  • barley aphids Schoizaphis graminum
  • barley aphids Sitobion avenae
  • rice aphids Toxoptera aurantii;
  • Polyphaga pests (a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne); (B) from the Attelabidae family, for example, Byctiscus betulae, Rhynchites heros; (C) from the family Bostrichidae, for example, Lyctus brunneus; (D) from the Brentidae family, for example, Cylas formicarius; (E) from the family Buprestidae, for example, Agrilus sinuatus; (F) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder; (G) Chrysomelidae, for example, Bruchus pisorum, Bruuchus rufimanus, eg, Bruchus spp .; eg, Northern corn, Dia
  • Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Inkubihoso yzae (Oule) Psylliodes angusticollis;
  • Pests Brachycera
  • A From the family Agromyzidae, for example, of the genus Liriomyza spp., Liriomyza bryoniae, Lariomyza chinensis, Liriomyza sativae, Liriomyza sativae, Liriomyza sativae, Liriomyza Others, Chromatomyia horticola, Agromyza oryzae;
  • B From the family Anthomyiidae, for example, Delia spp., Delia platura, Cabbage (Delia radicum); Other, Pegomya cunicularia;
  • C from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
  • D From the Ephydridae family, for example, Hydrellia griseo
  • Nematocera From the family of Cecidomyiidae, for example, the soybean flies (Asphondylia yushimai), the sorghum flies (Contarinia sorghicola), the flies (Mayetiola destructor), the mudworms (Sitodiplosis mosellana);
  • Grasshopper (Orthoptera) pests (a) Acrididae, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; Australian flying grasshopper (Chortoicetes terminifera),ixie locust (Dociostaurus maroccanus), Tosama locust (Locusta migratoria), Brown locust (Locustana pardalina), Red locust (Nomadacris septemfasciata), Oxya yezoensis; (B) from the family Gryllidae, for example, European crickets (Acheta domestica), Teleogryllus emma; (C) from the family Gryllotalpidae, for example, Gryllotalpa orientalis; (D) from the family Tettigoniidae, for example, Tachycines asynamorus;
  • Tick (Acari) (A) Astigmata (Acaridida) (A) Acaridae ticks, for example, Rhizoglyphus echinopus, Rhizoglyphus echinipus; Rhizoglyphus robini; for example, Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus, Acetus
  • A Mites of Tetranychidae, for example, Bryobia spp., Clover spider mite (Bryobia praetiosa), Fowl spider mite (Bryobia rubrioculus); Of the spider mite (Eotetranychus kankitus), tick (Eotetranychus asiaticus), tick (Eotetranychus kantis) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp.
  • Spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), spider mite (Oligonychus spp. , Citrus spider mites (Panonychus citri), swan spider mites (Panonychus mori), apple spider mites (Panonychus ulmi); , Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis; For example, Aponychus spp.
  • hus firmianae eg, Sasanychus spp., Sasanychus akitanus, Sasanychus pusillus; eg, Shizotetranychus spp., Shizotetranychus spel. Gastroid spider mites (Shizotetranychus longus), Shizotetranychus miscanthi, Shizotetranychus schizopus, tick (Tetranychina harti), Mite, Tetranychina harti
  • (B) Tenuipalpidae ticks for example, Brevipalpus spp. From Brevipalpus spi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus); for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other species, Tenuipalpus spp .; Other, Dolichotetranychus floridanus; (C) Tick of the family Eriophyidae, for example, Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Carnation of Aceria spp.
  • Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp.
  • emarginatae emarginatae
  • Aculops spp. Aculops lycopersici, Aculops pelekassi
  • Aculus spp. Aculus fockeui, Aculus fockeui
  • Others Acaphylla theavagrans, Chano Bidani (Calacarus carinatus), grape leaf burrowing mite (Colomerus vitis), grape rust mite (Calepitrimerus vitis), Nashisabidani (Epitrimerus pyri), Kinmoku rust mite (Paraphytoptus kikus), Makisabidani (Paracalacarus podocarpi), luchuensis tangerine rust mite (Phyllocotruta citri); (D) Mites of the family Transonemidae (eg, Tarsonemus spp.), Tarsonemus bilobatus, Tarsonemus waitei; Others, Phytonemus
  • the pest control agent of the present invention includes other active ingredients such as fungicides, insecticides / acaricides, nematicides, soil pesticides; plant regulators, synergists, fertilizers, soil improvers, animal use It may be mixed or used together with feed.
  • the combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect with respect to insecticidal / miticidal activity.
  • the synergistic effect can be confirmed by Colby's formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a standard method.
  • insecticide / acaricide, nematicide, soil insecticide, anthelmintic and the like that can be mixed or used in combination with the pest control agent of the present invention are shown below.
  • Acetylcholinesterase inhibitor (A) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxycarb Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
  • GABA-agonist chloride channel antagonists chlordane, endosulfan, etiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor; (3) Sodium channel modulators: Acrinatrin, d-cis-trans allethrin, d-transarethrin, bifenthrin, bioaresulin, bioareslin isomers, violesmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], delta
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine; (5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad; (6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime; (7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; geofenolan, ep
  • Mite growth inhibitor clofentezin, diflovidazine, hexythiazox, etoxazole;
  • Microbial-derived insect midgut mesentery Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp.
  • Crop proteins Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, phenbutasine oxide, propargite, tetradiphone; (13) Oxidative phosphorylation uncoupler: chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup; (14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride; nereistoxin; thiosultap sodium salt, thiocyclam; (15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron
  • Anthelmintic (A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, fulbendazole; fevantel, netobimine, thiophanate; thiabendazole, canbendazole; (B) salicylanilide series: closantel, oxyclozanide, rafoxanide, niclosamide; (C) substituted phenols: nitroxinyl, nitroskanate; (D) Pyrimidine series: Pirantel, Morantel; (E) imidazothiazole series: levamisole, tetramisol; (F) Tetrahydropyrimidine: praziquantel, epsiprantel; (G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole
  • Nucleic acid biosynthesis inhibitors (A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race; (B) an adenosine deamylase inhibitor: bupilimate, dimethylylmol, ethylimol; (C) DNA / RNA synthesis inhibitors: Himexazole, octirinone; (D) DNA topoisomerase II inhibitor: oxophosphate;
  • Mitotic fission inhibitor and cell division inhibitor (A) ⁇ -tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; ethaboxam; (B) Cell division inhibitor: Penciclone; (C) Delocalization inhibitor of spectrin-like protein: fluopicolide;
  • Respiratory inhibitor (A) Complex I NADH oxidoreductase inhibitor: diflumetrim; (B) Complex II succinate dehydrogenase: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumeciclos; carboxin, oxycarboxin; tifluzamide; , Isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid; (C) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Metominostrobin, Orisastrobin; Famoxadone; Fluo
  • Signaling inhibitor (A) Signaling inhibitor: quinoxyphene, proquinazide; (B) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolimate, iprodione, procymidone, vinclozolin;
  • Lipid and cell membrane synthesis inhibitors (A) Phospholipid biosynthesis, methyltransferase-inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane; (B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole; (C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb; (D) Microbial disturbance of pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain; (E) Agents that disrupt the cell membrane: an extract of Goseika Yupte (Tea Tree);
  • Cell membrane sterol biosynthesis inhibitors (A) Demethylation inhibitor at the C14 position in sterol biosynthesis: Trifolin; Triflumizole, biniconazole; Azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole, fluconazole, fluconazole-cis , Hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimethone, triadimenol, triticonazole; prothio
  • Trehalose and inositol biosynthesis agent Validamycin
  • B chitin synthase inhibitor: polyoxin, polyoxolim
  • C Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph
  • Bench Avaricarb Iprovaricarb, Toluprocarb, Variphenate
  • Mandipropamide
  • Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole; (B) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl;
  • Agents with multiple action points copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; farbum, mancozeb, maneb) , Mancopper, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; diclofluuranide, tolylfluanid; guazatine, iminotazine, iminoctadine albecylate, iminoctadine triacetate; Quinomethionate; fluorimide;
  • the ectoparasite control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
  • the compound of the present invention is excellent in the control effect of ectoparasites that are harmful to humans.
  • Examples of ectoparasites include ticks, lice and fleas.
  • Examples of host animals to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; domestic animals such as cattle, horses, pigs and sheep; warm-blooded animals such as poultry; Can be mentioned. In addition, a bee etc. can be mentioned.
  • Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, it infests the back, underarms, lower abdomen, and inner crotch of the host animal and obtains nutrients such as blood and dandruff from the animal.
  • the ectoparasite control agent of the present invention can be applied by a known veterinary technique (local, oral, parenteral or subcutaneous administration).
  • a known veterinary technique local, oral, parenteral or subcutaneous administration.
  • it is orally administered to animals by mixing tablets, capsules, feed, etc .; it is administered to animals by immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc .; kneading an ectoparasite control agent into a resin, shaping the kneaded product into an appropriate shape such as a collar or ear tag, and applying it to an animal A method of wearing and administering locally;
  • Hymenoptera pest bee of Argidae, bee of Cynipidae, bee of Diprionidae, bee of Formicidae, bee of Mutillidae, Bee of Tenthredinidae, Bee of Vespidae;
  • Formulation 1 wettable powder
  • Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above components were mixed uniformly and finely pulverized to obtain a wettable powder of 40% active ingredient.
  • Formulation 3 Granules
  • Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts
  • the above ingredients are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm, and the active ingredient is 5%. Get the granules.
  • Formulation 4 Granules
  • Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part
  • the above components are pulverized and mixed well, mixed well with water, granulated and dried, and 5% active ingredient. Get the granules.
  • Formulation 6 Granules
  • Compound of the present invention 5 parts Kaolin 94 parts White carbon 1 part
  • the compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.
  • Formulation 7 Injection
  • Compound of the present invention 0.1-1 part Peanut oil Balance After preparation, filter sterilize with a sterilization filter.
  • the filtrate was concentrated under reduced pressure to obtain a crude product of 2,6-dichloro-5-methoxypyrimidin-4-yl) methanol.
  • the resulting crude product of 2,6-dichloro-5-methoxypyrimidin-4-yl) methanol was dissolved in 20 ml of ethanol.
  • 1.2 g of triethylamine and 0.1 g of 10% palladium carbon were added at room temperature, the inside of the reaction vessel was replaced with hydrogen, and the mixture was stirred at 70 ° C. for 6 hours.
  • the reaction solution was poured into water and filtered through celite.
  • Step 1 Synthesis of ethyl 3- (ethylthio) -5- (trifluoromethyl) picolinate [ethyl 3- (ethylthio) -5- (trifluoromethyl) picolinate] 0.09 g of sodium hydride (purity 55%) was added to N, N-dimethyl Suspended in 25 ml formamide and cooled to 0 ° C. Ethyl mercaptan 0.27g was added to this, and it stirred at 0 degreeC for 30 minutes. Thereafter, 1.0 g of ethyl 3-chloro-5- (trifluoromethyl) picolinate synthesized with reference to the literature (Bessard, Y. et al.
  • 0.08 g of sodium hydride (purity 55%) was suspended in 15 ml of tetrahydrofuran and cooled to 0 ° C. To this was added 0.36 g of (3- (ethylthio) -5- (trifluoromethyl) pyridin-2-yl) methanol, and the mixture was stirred at 0 ° C. for 30 minutes. Thereafter, 0.36 g of 2,3-dichloro-5- (trifluoromethyl) pyridine was added thereto, and the mixture was warmed to room temperature and stirred for 3 hours. The reaction solution was poured into ice water and then extracted with ethyl acetate.
  • R 1 , (X 1 ) m , Z, A, B 5 , R 2 , and (X 2 ) n in Table 1 are those in the compound represented by the formula (II).
  • R a in CHR a shown in the column A of Compound No. 1-19 represents a ((3-chloro-5-trifluoromethyl-pyridin-2-yl) oxy) methyl group.
  • R 1 , (X 1 ) m , Z, A, B 5 , R 2 , and (X 2 ) n in Table 2 are those in the compound represented by the formula (III).
  • R 1 , (X 1 ) m , Z, A, B 5 , R 2 , and (X 2 ) n in Table 3 are those in the compound represented by the formula (IV).
  • R 1 , (X 1 ) m , Z, A, B 5 , R 2 , and (X 2 ) n in Table 4 are those in the compound represented by the formula (V).
  • test examples show that the compounds of the present invention are useful as active ingredients of pest control agents, particularly insecticides or acaricides. “Parts” described in the test examples is “parts by weight”.
  • Test Example 1 Efficacy Test for Bean Aphids First, 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion containing 5% active ingredient did. The bean aphid was released on the cowpea where the primary leaves developed. When one day had passed since the release, the first-born larvae that were delivered remained, and the adults were removed. The emulsion was diluted with water to a compound concentration of 125 ppm. The diluted solution was sprayed on the cowpea. Thereafter, the cowpea was kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%.
  • Test Example 2 Efficacy test against brown planthopper An emulsion was prepared according to the formulation described in Test Example 1. The emulsion was diluted with water to a compound concentration of 125 ppm. Rice seedlings were immersed in the diluted solution for 10 seconds and then air-dried. A plastic bag with a hole was put on the rice seedlings, and 10 second-instar larvae of the brown planthopper were released in the plastic bag. Thereafter, the rice seedlings were kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release of the insects, the survival of the brown planthopper was examined and the insecticidal rate was determined.
  • a drug-insensitive line (line collected in Kumamoto Prefecture in 2011 and kept indoors) was used. The following compounds were tested for efficacy against the brown planthopper. All compounds had an insecticidal rate of 80% or more. 1-12, 1-13, 1-14, 1-15, 1-20, 1-21, 1-23, 1-24, 1-26, 2-1, 2-2, 2-3, 3- 1, 4-1
  • Imidacloprid and buprofezin were tested for efficacy against the brown planthopper.
  • Imidacloprid was an insecticidal rate of 50% at 125 ppm for drug-insensitive lines.
  • Buprofezin was 70% insecticidal at 125 ppm for drug-insensitive lines.
  • Test Example 3 Efficacy Test for Tobacco Whitefly An emulsion was prepared according to the formulation described in Test Example 1. The emulsion was diluted with water to a compound concentration of 125 ppm. The diluted solution was sprayed on tomato cut leaves and then air-dried. In the flask, the leaf was fixed using absorbent cotton so that the leaf surface faced upward. In this flask, 7 pairs of adult tobacco whitefly type B were released and parasitized on tomato cut leaves. Thereafter, the tomato cut leaves were kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When two days had passed since the release, the larvae were kept and the adults were removed. The number of surviving larvae was examined when 12 days had passed since the release.
  • Next generation control rate 100 ⁇ ⁇ (T ⁇ Ca) / (Ta ⁇ C) ⁇ ⁇ 100
  • Ta Number of parasites immediately after release in the spray treatment section
  • T Number of parasites 12 days after release in the spray treatment section
  • Ca Number of parasites immediately after release in the untreated section
  • C 12 days after release in the untreated section
  • the number of parasites was tested for the efficacy of the following compounds against tobacco whiteflies. All the compounds had a next-generation control rate of 80% or more. 1-12, 1-13, 1-15, 1-16, 1-18, 1-21, 1-24, 1-26, 1-27, 2-1, 2-2, 2-3, 3- 1, 4-1
  • Test Example 4 Efficacy Test against Acacia Toyo Emulsion was prepared according to the formulation described in Test Example 1. The emulsion was diluted with water to a compound concentration of 125 ppm. Corn leaves were immersed in the diluted chemical solution for 30 seconds and then air-dried. The corn leaves were placed in a petri dish with filter paper, and 5 second-instar larvae were released on the leaves, and a glass lid was placed thereon. Thereafter, the corn leaves were kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release of the insects, the life-and-death of the kingfisher was examined and the insecticidal rate was determined. The following compounds were tested for the efficacy against the above-mentioned Ayuyoto. All compounds had an insecticidal rate of 80% or more. 1-7, 1-8, 1-9
  • Test Example 5 Efficacy test against spider mite of Kanzawa Ten adult females of spider mite from Okayama were inoculated on the primary leaves 7 to 10 days after germination of green beans seeded in a three-size pot. An emulsion was prepared according to the formulation described in Test Example 1. The emulsion was diluted with water to a compound concentration of 125 ppm. The diluted solution was sprayed on the kidney beans. Thereafter, the green beans were kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 3 days had passed since spraying, the life and death of adults were examined and the insecticidal rate was determined.
  • Heteroaryl compound having excellent pest control activity in particular, insecticidal activity and / or acaricidal activity, excellent safety, and can be synthesized industrially advantageously, and pest control agent and insecticide containing this as an active ingredient Alternatively, an acaricide or ectoparasite control agent can be provided.

Abstract

La présente invention est un composé représenté dans la formule (I-1) et analogue, ou un sel de ce dernier. La présente invention concerne un agent de lutte contre des organismes nuisibles et analogues, contenant au moins un élément choisi dans le groupe constitué du composé susmentionné et un sel de ce dernier en tant qu'ingrédient actif. [Dans la formule (I-1): R1 indique un groupe alkyle ou similaire; X1 indique un groupe alkyle ou similaire; m indique la quantité de X1 et est un nombre entier de 0 à 2; B1, B3, B6, et B5 indiquent chacun indépendamment un atome de carbone ou un atome d'azote; R2 indique un groupe alkyle ou similaire; X2 indique un groupe alkyle ou similaire; n indique la quantité de X2 et est un nombre entier de 0 à 2; Z indique un atome d'oxygène ou similaire; et A indique un groupe alkylène ou similaire.]
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