WO2017069154A1 - Amide compound and pest control agent - Google Patents

Amide compound and pest control agent Download PDF

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Publication number
WO2017069154A1
WO2017069154A1 PCT/JP2016/080957 JP2016080957W WO2017069154A1 WO 2017069154 A1 WO2017069154 A1 WO 2017069154A1 JP 2016080957 W JP2016080957 W JP 2016080957W WO 2017069154 A1 WO2017069154 A1 WO 2017069154A1
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group
substituted
unsubstituted
formula
compound
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PCT/JP2016/080957
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French (fr)
Japanese (ja)
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裕紀 古川
睦大 天野
岩佐　孝男
康介 椎木
寛子 諸江
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日本曹達株式会社
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Publication of WO2017069154A1 publication Critical patent/WO2017069154A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—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
    • A01N43/90—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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • C07D213/68—One oxygen atom attached in position 4
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

Definitions

  • the present invention relates to an amide compound and a pest control agent. More specifically, the present invention relates to an amide compound which has excellent acaricidal activity and / or insecticidal activity, is excellent in safety, and can be synthesized industrially advantageously, and a pest control agent containing this as an active ingredient About.
  • This application claims priority based on Japanese Patent Application No. 2015-207080 filed in Japan on October 21, 2015, the contents of which are incorporated herein by reference.
  • Patent Literature 1 disclose aryloxyureas and aryloxyacetic acid amides as compounds structurally related to the amide compound of the present invention.
  • An object of the present invention is to provide an amide compound having excellent pesticidal activity, in particular, acaricidal activity and / or insecticidal activity, excellent safety, and industrially advantageous synthesis, and harmful substances containing this as an active ingredient. It is to provide a biocontrol agent.
  • Z is an oxygen atom or a sulfur atom.
  • A is a group represented by the formula (A-1) or a group represented by the formula (A-2).
  • B is a group represented by the formula (B-1) when A is a group represented by the formula (A-1), and B is a group represented by the formula (A-2) It is a group represented by B-2).
  • W is a nitrogen atom or CH.
  • * represents a bonding position.
  • X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy Group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alky
  • n represents the number of substitutions of X and is an integer from 0 to 3. When n is 2 or 3, Xs may be the same or different.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a phenyl group.
  • R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • R 4 and R 5 are each independently a hydrogen atom or an unsubstituted C 1-6 alkyl group. R 4 and R 5 may be joined together to form a ring together with the carbon atom to which they are attached.
  • R 6 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
  • R 7 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted heteroaryl group.
  • a pest control agent comprising at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof as an active ingredient.
  • An acaricide or insecticide containing as an active ingredient at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
  • An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
  • the amide compound of the present invention can control pests that are problematic in crops and hygiene. In particular, mites and pests can be effectively controlled.
  • the amide compound of the present invention is a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)) or a salt of compound (1).
  • the term “unsubstituted” means that only the group serving as a mother nucleus. When only the name of a group serving as a mother nucleus is described, it means “unsubstituted” unless otherwise specified.
  • the term “substituted” 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.
  • the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
  • Specific examples of the group that can be a “substituent” include the following groups. Halogeno groups such as fluoro, chloro, bromo and iodo groups; 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, 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 A C2-6 alkenyl group such as a hexenyl group, a 5-hexenyl group;
  • Ethynyl 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc.
  • a C2-6 alkynyl group of A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cubanyl group;
  • a C3-8 cycloalkenyl group such as a 2-cyclopropenyl group, 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; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadia
  • Hydroxyl group oxo group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryloxy groups such as phenoxy group and naphthoxy group; 5- to 6-membered heteroaryloxy group such as thiazolyloxy group and pyridyloxy group;
  • Carboxyl group A formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group and propionyloxy group; A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
  • 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 C3-6 halocycloalkyl group such as a 3,3-difluorocyclobutyl group;
  • C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-
  • a aminocarbonyl group such as a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, an i-propylaminocarbonyl group;
  • Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
  • Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
  • a C1-6 alkoxyimino C1-6 alkyl group such as a methoxyiminomethyl group and a (1-methoxyimino) ethyl group;
  • 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 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
  • C2-6 alkenylthio groups such as vinylthio group and allylthio group;
  • a C2-6 alkynylthio group such as an ethynylthio group or a propargylthio group;
  • a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
  • a tri-C1-6 alkylsilyl group such as a trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
  • a tri-C6-10 arylsilyl group such as a triphenylsilyl group; In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • “Terms such as“ C1-6 ” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because a group serving as a mother nucleus is a butyl group and a substituent is an ethoxy group.
  • Z is an oxygen atom or a sulfur atom.
  • Z is an oxygen atom
  • it may be called acid amides
  • Z when Z is a sulfur atom, it may be called thioamides.
  • Thioamides in which Z in formula (1) is a sulfur atom have low water solubility compared to acid amides, and therefore have a low mobility in the environment and animal organisms, and are preferable from the viewpoint of safety. Have.
  • A represents a substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group, a substituted or unsubstituted [(pyridin-4-yl) oxy] methyl group, or a substituted or unsubstituted An unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group.
  • the substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group and [(pyridin-4-yl) oxy] methyl group in A are preferably groups represented by the formula (A-1) It is.
  • the substituted or unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group in A is preferably a group represented by the formula (A-2).
  • X represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ⁇ 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted Substituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsul
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • the “C1-6 alkyl group” in X may be a straight chain or a branched chain.
  • 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.
  • Examples of the “C2-6 alkenyl group” in X include 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.
  • the “C2-6 alkynyl group” in X is an 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 group 1,1-dimethyl-2-butynyl group and the like.
  • C1-6 alkoxy group a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
  • Examples of the “C1-6 alkylamino group” in X include a methylamino group, a dimethylamino group, and a diethylamino group.
  • Examples of the “C1-6 alkylcarbonyl group” in X include an acetyl group and a propionyl group.
  • Examples of the “C1-6 alkylaminocarbonyl group” in X include a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, and an i-propylaminocarbonyl group.
  • Examples of the “C1-6 alkoxyimino C1-6 alkyl group” in X include a methoxyiminomethyl group and a (1-methoxyimino) ethyl group.
  • C1-6 alkyl group C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylamino group”, “C1-6 alkylcarbonyl group” in X , “C1-6 alkylaminocarbonyl group”, and “C1-6 alkoxyimino C1-6 alkyl group”, preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy Groups, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group, etc .; C6-10 groups such as phenyl group, naphthyl group
  • Examples of the “C1-6 alkylthio group” in X include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like.
  • Examples of the “C1-6 alkylsulfinyl group” in X include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
  • Examples of the “C1-6 alkylsulfonyl group” in X include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
  • Examples of the “C1-6 alkoxysulfonyl group” in X include a methoxysulfonyl group, an ethoxysulfonyl group, a t-butoxysulfonyl group, and the like.
  • C1-6 alkylthio group preferably a fluoro group, a chloro group
  • Halogeno groups such as bromo group, iodo group
  • C1 ⁇ 6 alkoxy groups preferably a fluoro group
  • C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group
  • cyano group preferably a fluoro group, a chloro group
  • Halogeno groups such as bromo group, iodo group
  • C1 ⁇ 6 alkoxy groups preferably a fluoro group
  • C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group
  • cyano group preferably a fluoro group, a chloro group
  • Halogeno groups such as bromo group, iodo group
  • C1 ⁇ 6 alkoxy groups
  • Examples of the “C3-8 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the “C6-10 aryl group” in X include a phenyl group and a naphthyl group.
  • heteroaryl group in X, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group (for details, [1,2,3] Triazolyl group or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,3] oxadiazolyl group, [1,2,4] oxadiazolyl group, [1,2,5] oxadiazolyl group Or a [1,3,4] oxadiazolyl group), a thiadiazolyl group, a tetrazolyl group or the like; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group
  • Examples of the “C6-10 aryloxy group” in X include a phenoxy group and a naphthoxy group.
  • heteroaryloxy group examples include 5- to 6-membered heteroaryloxy groups such as thiazolyloxy group and pyridyloxy group.
  • Substituents on the “C3-8 cycloalkyl group”, “C6-10 aryl group”, “heteroaryl group”, “C6-10 aryloxy group”, and “heteroaryloxy group” in X are preferably fluoro Group, chloro group, bromo group, iodo group and other halogeno groups; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group C1-6 alkyl groups such as n-pentyl group and n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as perfluoro-n-pentyl group; methoxy group, ethoxy
  • X represents a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group C1-6 alkylamino group, C1-6 alkylaminocarbonyl group, C1-6 haloalkylaminocarbonyl group, C1-6 alkoxyimino C1-6 alkyl group, C6-10 aryl C1-6 alkoxyimino C1-6 alkyl group, A C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C6-10 aryl group, a heteroaryl group, a nitro group, or a cyano group is preferable, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group More preferably a C1-6 alkylamino group, a
  • R 1 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group Or a phenyl group.
  • Specific examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C2-6 alkynyl group” in R 1 are the same as those exemplified for X.
  • the substituent on the “C1-6 alkyl group”, “C2-6 alkenyl group”, or “C2-6 alkynyl group” in R 1 is preferably a halogeno group.
  • R 1 is preferably a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or a phenyl group, More preferred is a C1-6 alkyl group.
  • W is a nitrogen atom or CH.
  • R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. Specific examples of the “C1-6 alkyl group” for R 2 and R 3 include the same as those exemplified for X. The substituent on the “C1-6 alkyl group” in R 2 and R 3 is preferably a halogeno group. In formula (A-2), R 2 or R 3 is preferably a hydrogen atom.
  • B is a group represented by Formula (B-1) when A is a group represented by Formula (A-1), and A is represented by Formula (A-2).
  • the compound (1) composed of a combination of A and B in the formula (1) is a compound represented by the formula (2) or the formula (3).
  • Formula (2) is expressed by Formula (2-1) or Formula (2-2).
  • R 4 and R 5 are each independently a hydrogen atom or a C1-6 alkyl group. Examples of the C1-6 alkyl group for R 4 and R 5 are the same as those exemplified for X.
  • R 4 and R 5 are preferably methyl groups.
  • R 4 and R 5 may be connected to form a ring together with the carbon atom to which they are bonded.
  • Examples of the ring formed by connecting R 4 and R 5 include alicyclic rings having 3 to 6 carbon atoms such as a cyclopropane ring, a cyclobutane ring, and a cyclohexane ring, and a cyclopropane ring is preferable.
  • R 6 represents a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
  • R 7 is a substituted or unsubstituted aminocarbonyl group or a substituted or unsubstituted heteroaryl group.
  • Examples of the substituent on the “aminocarbonyl group” in R 6 or R 7 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy.
  • the “substituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminocarbonyl group, a substituted Or an unsubstituted C3-6 cycloalkylaminocarbonyl group, a substituted or unsubstituted cyclic aminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyaminocarbonyl group, a substituted or unsubstituted N- (C1-6 alkyl)- N- (C1-6 alkoxy) aminocarbonyl group, 2-mono C1-6 alkylhydrazine-1-carbonyl group, 2,2-diC1-6 alkylhydrazine-1-carbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) aminocarbonyl group and the like.
  • R 6 or R 7 a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an i-propylaminocarbonyl group, an n-butylaminocarbonyl group, Examples thereof include s-butylaminocarbonyl group, t-butylaminocarbonyl group, i-butylaminocarbonyl group, n-pentylaminocarbonyl group, i-pentylaminocarbonyl group, n-hexylaminocarbonyl group and the like.
  • Examples of the “di-C1-6 alkylaminocarbonyl group” in R 6 or R 7 include a dimethylaminocarbonyl group, a methylethylaminocarbonyl group, a diethylaminocarbonyl group and the like.
  • Examples of the “C3-6 cycloalkylaminocarbonyl group” in R 6 or R 7 include a cyclopropylaminocarbonyl group, a cyclobutylaminocarbonyl group, a cyclopentylaminocarbonyl group, a cyclohexylaminocarbonyl group and the like.
  • the “cyclic aminocarbonyl group” in R 6 or R 7 is a group in which a cyclic amino group such as an aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a carbonyl group, specifically piperidine-1 And -carbonyl group, piperazine-1-carbonyl group, and pyrrolidine-1-carbonyl group.
  • Examples of the “C1-6 alkoxyaminocarbonyl group” in R 6 or R 7 include methoxyaminocarbonyl group, ethoxyaminocarbonyl group, n-propoxyaminocarbonyl group and the like.
  • N- (C1-6 alkyl) -N- (C1-6 alkoxy) aminocarbonyl group in R 6 or R 7 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents of the aminocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminocarbonyl group and N-methyl-N-ethoxyaminocarbonyl group.
  • the “2-mono C1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a mono C1-6 alkylamino group as a substituent for the aminocarbonyl group. Examples thereof include a methyl hydrazine-1-carbonyl group and a 2-ethylhydrazine-1-carbonyl group.
  • the “2,2-diC1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a diC1-6 alkylamino group as a substituent of the aminocarbonyl group.
  • Examples include 2,2-dimethylhydrazine-1-carbonyl group, 2,2-diethylhydrazine-1-carbonyl group, and the like.
  • Examples of the “(((C1-6 alkoxyimino) methyl) aminocarbonyl group” in R 6 or R 7 include a ((methoxyimino) methyl) aminocarbonyl group or a ((ethoxyimino) methyl) aminocarbonyl group.
  • the “substituted or unsubstituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group, substituted or unsubstituted.
  • a C1-6 alkylaminocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group is preferred.
  • Examples of the “C2-6 haloalkenyl group” for G 1 include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
  • Examples of the “C2-6 haloalkynyl group” in G 1 include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group, and the like.
  • Examples of the “C1-6 haloalkoxy group” in G 1 include 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, and the like. Can do.
  • Examples of the “C1-6 haloalkylthio group” for G 1 include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
  • Examples of the “C1-6 haloalkylsulfinyl group” in G 1 include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
  • Examples of the “C1-6 haloalkylsulfonyl group” for G 1 include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
  • C2-6 alkenyl group “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C3-6 cycloalkyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl” in G 1 Group, C1-6 alkylsulfonyl group, C6-10 aryl group, 5-membered heteroaryl group, 6-membered heteroaryl group, condensed heteroaryl group,
  • Examples of the “halogeno group” include the same as those exemplified for X.
  • C6-10 aryl group “5-membered heteroaryl group”, “6-membered heteroaryl group”, and “fused-ring heteroaryl group” in G 1 may be substituted with “halogeno group” Good.
  • G 1 includes a C2-6 alkenyl group, a C2-6 haloalkenyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group.
  • Particularly preferred “substituted or unsubstituted aminocarbonyl group” for R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group
  • substituent G 1 is a C2-6 alkenyl group, C2-6 Haloalkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group , C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, optionally substituted with a halogeno group, C6-10 Aryl group, 6-membered heteroaryl group (option
  • Examples of the substituent on the “thioaminocarbonyl group” in R 6 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, Examples thereof include a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted (C1-6 alkoxyimino) methyl group, or an oxetanyl group. .
  • the “substituted aminothiocarbonyl group” in R 6 includes a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3 to C3— 6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted cyclic aminothiocarbonyl group, substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, substituted or unsubstituted N- (C1-6 alkyl) -N- ( C1-6 alkoxy) aminothiocarbonyl group, 2-mono C1-6 alkylhydrazine-1-thiocarbonyl group, 2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) amino
  • Examples of the “mono C1-6 alkylaminothiocarbonyl group” in R 6 include a methylaminothiocarbonyl group, an ethylaminothiocarbonyl group, an n-propylaminothiocarbonyl group, an i-propylaminothiocarbonyl group, an n-butylaminothio group.
  • Examples of the “di-C1-6 alkylaminothiocarbonyl group” in R 6 include dimethylaminothiocarbonyl group, methylethylaminothiocarbonyl group, diethylaminothiocarbonyl group and the like.
  • Examples of the “C3-6 cycloalkylaminothiocarbonyl group” for R 6 include a cyclopropylaminothiocarbonyl group, a cyclobutylaminothiocarbonyl group, a cyclopentylaminothiocarbonyl group, a cyclohexylaminothiocarbonyl group, and the like.
  • the “cyclic aminothiocarbonyl group” in R 6 is a group in which a cyclic amino group such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a thiocarbonyl group, specifically piperidine-1- A thiocarbonyl group, a piperazine-1-thiocarbonyl group, and a pyrrolidine-1-thiocarbonyl group can be mentioned.
  • Examples of the “C1-6 alkoxyaminothiocarbonyl group” for R 6 include a methoxyaminothiocarbonyl group, an ethoxyaminothiocarbonyl group, an n-propoxyaminothiocarbonyl group, and the like.
  • N— (C1-6 alkyl) -N— (C1-6 alkoxy) aminothiocarbonyl group in R 6 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents for the aminothiocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminothiocarbonyl group and N-methyl-N-ethoxyaminothiocarbonyl group.
  • the “2-mono C1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a mono C1-6 alkylamino group as a substituent of the aminothiocarbonyl group, specifically 2-methyl Examples thereof include a hydrazine-1-thiocarbonyl group and a 2-ethylhydrazine-1-thiocarbonyl group.
  • the “2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a diC1-6 alkylamino group as a substituent of the aminothiocarbonyl group. 2,2-dimethylhydrazine-1-thiocarbonyl group, 2,2-diethylhydrazine-1-thiocarbonyl group, and the like.
  • Examples of the “((C1-6 alkoxyimino) methyl) aminothiocarbonyl group” for R 6 include a ((methoxyimino) methyl) aminothiocarbonyl group or a ((ethoxyimino) methyl) aminothiocarbonyl group.
  • the “substituted or unsubstituted aminothiocarbonyl group” in R 6 is a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted.
  • a cyclic aminothiocarbonyl group a substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, a substituted or unsubstituted ((C1-6 alkoxyimino) methyl) aminothiocarbonyl group, and more preferably a substituted or unsubstituted group.
  • a substituted mono C1-6 alkylaminothiocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group is preferred.
  • G 1 Specific examples of these groups include the same ones as those exemplified in G 1. Further, the C6-10 aryl group, the 5-membered heteroaryl group, the 6-membered heteroaryl group, and the condensed heteroaryl group may be further substituted with a halogeno group.
  • Preferred G 2 is the same as described in G 1 .
  • R 6 include "substituted or unsubstituted amino thiocarbonyl group” is substituted or unsubstituted mono- C1 ⁇ 6 alkylaminothiocarbonyl group (preferred substituents G 2 are, C2 ⁇ 6 alkenyl group, C2 ⁇ 6 halo Alkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, C6-10 aryl (which may be substituted with a halogeno group)
  • heteroaryl group examples include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.
  • the “heteroaryl group” for R 7 is preferably a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, more preferably a pyridyl group or a pyrimidinyl group, and pyridin-2-yl More preferred is a group or a pyrimidin-2-yl group.
  • the “heteroaryl group” for R 7 preferably has 1 to 4 substituents, more preferably 1 to 2 substituents. When having two or more substituents, the substituents may be the same or different. When R 7 is a pyridin-2-yl group or a pyrimidin-2-yl group, the substituent is preferably at the 4-position.
  • Examples of the substituent (hereinafter referred to as Y) on the “heteroaryl group” in R 7 include a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, carboxyl group, formyl group, substituted or unsubstituted C1-6 alkyl Carbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1 -6 alkylthio group, substituted
  • Halogeno group in Y substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkoxy group, substituted Or an unsubstituted C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl Group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C1-6 alkoxysulfonyl group, substituted Or an un
  • Examples of the “C1-6 alkoxycarbonyl group” in Y include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.
  • the substituent on the “C1-6 alkoxycarbonyl group” in Y is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group Group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group C1-6 haloalkoxy groups such as: C6-10 aryl groups such as phenyl groups and naphthyl groups; cyano groups;
  • Examples of the substituent on the “heteroaryl group” for R 7 include a C1-6 haloalkoxy group, a C1-6 alkylsulfoxyimino group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkylsulfonyl group. Is preferred.
  • the amide compound of the present invention is preferably a compound represented by formula (2) (hereinafter sometimes referred to as compound (2)) or a salt thereof.
  • Z represents the same as that in the formula (1).
  • R 1 , W, X, and n are the same as those in formula (A-1).
  • R 4 , R 5 and R 6 are the same as those in the formula (B-1).
  • the salt of the compound (1) of 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 and salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
  • the amide compound of the present invention can be obtained by a known method.
  • the salt of compound (1) can be produced from compound (1) by a known method.
  • the 4-halopyridine compound is reacted with a 2-hydroxycarboxylic acid ester compound in the presence of a base to obtain a 2-[(pyridin-4-yl) oxy] carboxylic acid ester compound, which is then hydrolyzed to give 2 A — [(pyridin-4-yl) oxy] carboxylic acid compound is obtained, and this is reacted with an N-substituted amine compound to obtain a compound represented by the formula (2-2).
  • Hal is a halogeno group.
  • R 1a is not particularly limited, and is, for example, a C1-6 alkyl group.
  • a compound represented by the formula (2-1) can be obtained by using an N-hydroxycarbamic acid ester compound instead of the 2-hydroxycarboxylic acid ester compound.
  • R 1a is not particularly limited, but is, for example, a C1-6 alkyl group.
  • the amide compound of the present invention is excellent in controlling pests such as various mites that affect plant growth.
  • the amide compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals.
  • the amide compound of the present invention is useful as an active ingredient of an acaricide.
  • the amide compound of the present invention exhibits an excellent control effect not only on mites of sensitive strains but also on mite-resistant mites which have recently become a problem.
  • the amide compound of the present invention is excellent in the control effect of endoparasites that are harmful to humans and animals. 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 endoparasite control agent.
  • the amide compound of the present invention exhibits efficacy at all stages of development of organisms to be controlled, and exhibits excellent control effects on, for example, eggs, nymphs, larvae, pupae and adults such as mites and insects. .
  • the pest control agent or acaricide or insecticide of the present invention contains, as an active ingredient, at least one selected from the amide compounds of the present invention, that is, the compound (1) and the salt of the compound (1).
  • the amount of the amide compound contained in the pest control agent or the acaricide or insecticide of the present invention is not particularly limited as long as it exhibits a pest control effect.
  • the pest control agent or acaricide or insecticide of the present invention includes cereals, vegetables, root vegetables, potatoes, flowering plants, fruit trees, foliage plants, trees such as tea, coffee, cacao, grasses, turf Kind: It is preferably used for plants such as cotton.
  • the pest control agent or acaricide or insecticide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used for the part.
  • the pest control agent or acaricide or insecticide of the present invention is not particularly limited depending on the species of the plant to be applied. Examples of plant seeds include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).
  • the pest control agent or acaricide or insecticide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various mites.
  • Lepidoptera butterfly or moth (a) moths of the Arctiidae family, eg Hyphantria cunea, Lemyra imparilis; (b) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella; (c) moths of Carposinidae, for example, Carposina sasakii; (d) moths of the family Craambidae, 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
  • Gelechiidae moths for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella
  • Geometridae moths for example Ascotis selenaria
  • moths from the family Gracillariidae for example, Caloptilia theivora, citrus leafworm (Phyllocnistis citrella), phleglonorycter ringoniella
  • Hesperiidae butterflies such as Parnara
  • (k) moths of the family Lyonetiidae for example, Lyonetia clerkella, Lyonetia prunifoliella malinella, from the genus Lyonetia spp .;
  • (l) Noctuidae moths for example, Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, ), African Spodoptera littoralis, Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotis sp.
  • Agrotis ipsilon, Agrotis segetum for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Of the species (Heliothis spp.), Heliothis armigera, Heliothis virescens; Others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenis jacen Peridroma saucia), soy bean looper (Pseudoplusia includens), nettle wain (Trichoplusia ni); (m) Nolidae moths, such as Misaria Olingsa (Earias insulana); (n) Pieridae butterflies, for example, Pieris sp., Pieris brassicae, Pieris
  • Thysanoptera pest (a) from the Phlaeothripidae family, for example, Ponticulothrips diospyrosi; (b) from the Thripidae family, for example, Frankliniella intonsa, Frankliniella occidentalis; for example, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; other, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.
  • Pests of the Hemiptera (A) Cervical antrum (Archaeorrhyncha) (a) From the Delphacidae family, for example, the green planthopper (Laodelphax striatella), the green planthopper (Nilaparvata lugens), the black planthopper (Perkinsiella saccharicida), and the white planthopper (Sogatella furcifera).
  • Clypeorrhyncha (a) From the family of Cicadellidae, for example, Empoasca spp., Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Others ).
  • 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 of the family Lygaeidae, for example, the American leaf beetle (Blissus leucopterus), the leaf beetle (Cavelerius saccharivorus), the leaf beetle (Togo hemipterus); (d) From the Miridae family, for example, the black beetle turtle (Halticus insularis), the red-bellied turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the long-nosed turtle (Stenodema sibiricum), the Stellata tus rutus ), Trigonotylus caelestialium;
  • (D) Sternorrhyncha (a) from the family Adelgidae, for example, Adelges laricis; (b) Aleyrodidae, for example, Bemisia spp., Silver leaf whiteflies (Bemisia argentifolii), Tobacco whiteflies (Bemisia tabaci); Others citri), Trialeurodes vaporariorum; (c) Aphididae, for example, from Aphis spp., Aphis craccivora, bean aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii) , European apple aphids (Aphis pomi), elder-core aphids (Aphis sambuci), Aphis spiraecola; for example, Rhopalosiphum spp.
  • Aphididae for example, from Aphis spp., Aphi
  • Dysaphis spp. from the genus Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; for example, Macrosiphum spp., Macrosiphum avenae, aphid (Macrosiphum euphorbiae); e.g. Myzus spp.
  • Mussels (Myzus cerasi), peach aphids (Myzus persicae), myrtle aphids (Myzus varians); other, pea beetle aphids (Acyrthosiphon pisum), potato beetles Aphids (Brevicoryne brassicae), strawberry aphids (Chaetosiphon fragaefolii), peach beetles (Hyalopterus pruni), Hyperomyzus lactucae, black-headed aphids (Lipaphis erysimi), ura aphids Aphids (Metopolophium dirhodum), lettuce aphids (Nasonovia ribis-nigri), hops aphids (Phorodon humuli), barley aphids (Schizaphis graminum), barley aphids (Sitobion avenae), comican aphids
  • Polyphaga pests (a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne); (b) from the family Attelabidae, for example, Byctiscus betulae, Rhynchites heros; (c) from the Bostrichidae family, for example, Lyctus brunneus; (d) from the Brentidae family, for example, Cylas formicarius; (e) from the Buprestidae family, for example, Agrilus sinuatus; (f) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder; (g) Northern corn of the Chrysomelidae family, for example, Bruchus spp., Bruchus pisorum, Bruchus rufimanus; eg, Diabrotica
  • Rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi potato beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Inkubihoso yzae (Oule) Psylliodes angusticollis;
  • Flies (Diptera) pests A) Brachycera (a) From the family Agromyzidae, for example, from the genus Liriomyza spp., from Liriomyza bryoniae, from Liriomyza chinensis, from tomato leaf (Liriomyza sativae), from rio myza trifoli; Others, Chromatomyia horticola, Agromyza oryzae; (b) From the family Anthomyiidae, for example, Delia spp., Dela platura, Cabbage fly (Delia radicum); Other, Pegomya cunicularia; (c) Drosophila suzukii from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii; (d) from the Ephydridae family, for example, Hydrellia griseola;
  • Nematocera From the family Cecidomyiidae, for example, the soybean fly (Asphondylia yushimai), the sorghum fly (Contarinia sorghicola), the fly fly (Mayetiola destructor), the mud fly (Sitodiplosis mosellana).
  • Grasshopper (Orthoptera) pests (a) From the Acrididae family, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; (Dociostaurus maroccanus), grasshopper (Locusta migratoria), brown locust (Locustana pardalina), red locust (Nomadacris septemfasciata), cobaneago (Oxya yezoensis); (b) From the family of crickets (Gryllidae), for example, European cricket (Acheta domestica), Teleogryllus emma; (c) from the family Gryllotalpidae, for example, Gryllotalpa orientalis; (d) From the Tettigoniidae family, for example, Tachycines asynamorus.
  • Acrididae family for example, Schistocerca spp., Schistocerca americana, Schistocer
  • Tick (Acari) (A) Astigmata (Acaridida) (a) Acaridae ticks, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; for example, Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus tick
  • B Prostigmata mite (Actinedida)
  • (a) Tetranychidae ticks for example, Bryobia spp., Clover spider mites (Bryobia praetiosa), Fowl spider mites (Bryobia rubrioculus); , White spider mite (Eotetranychus kankitus), tick mite (Eotetranychus kankitus) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp.
  • Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychu s orthius), Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; tick, Pony Panonychus mori), apple spider mites (Panonychus ulmi); for example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus vorni, Tetranychus tranni (Tetranychus phaselus), nite spider mite (Tetranychus urticae), mite spider mite (Tetranychus viennensis); for example, Aponicchus spp.
  • Sasanychus akitanus Spider mites (Sasanychus pusillus); for example, Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanzo, chus Willow spider mites (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis, Kew spider mite (Yezonychus sapporensis);
  • Tenuipalpidae ticks for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus), for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other, Tenuipalpus zhizhilashviliae;
  • Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp.
  • the pest control agent or acaricide or insecticide of the present invention may contain components other than the amide compound of the present invention.
  • examples of other components include known carriers used for formulation.
  • conventionally known fungicides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, etc. be able to. By containing such other components, there may be a synergistic effect.
  • 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, Propoxyl Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
  • GABA-agonist chloride channel antagonists acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor, dienochlor.
  • Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine, flupiradiflon.
  • Nicotinic acetylcholine receptor allosteric modulator spinetoram, spinosad.
  • Juvenile hormone-like substances hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epofenonane, triprene.
  • Non-specific inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar.
  • Homogeneous selective feeding inhibitors flonicamid, pymetrozine, pyrifluquinazone.
  • Tick growth inhibitor clofentezin, difluvidazine, hexythiazox, etoxazole.
  • Microbial-derived insect midgut lining destroyer Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp.
  • Crop proteins Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
  • Mitochondrial ATP biosynthetic enzyme inhibitors diafenthiuron, azocyclotin, cyhexatin, fenbutasine oxide, propargite, tetradiphone.
  • Oxidative phosphorylation uncouplers chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup.
  • Nicotinic acetylcholine receptor channel blocker bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam.
  • Chitin synthesis inhibitor bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
  • Diptera molting agent cyromazine.
  • Molting hormone receptor agonists Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.
  • Octopamine receptor agonist Amitraz, demiditraz, chlordimeform.
  • Mitochondrial electron transport system complex III inhibitor acequinosyl, fluacrylpyrim, hydramethylnon.
  • Mitochondrial electron transport system complex I inhibitor phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.
  • 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 series: praziquantel, epsiprantel; (g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazo
  • Nucleic acid biosynthesis inhibitors (a) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race; (b) adenosine deaminase 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: Pencyclon; (c) Delocalization inhibitor of spectrin-like protein: fluopicolide.
  • Respiratory inhibitor (a) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad; (b) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumeciclos; carboxin, oxycarboxin; tifluzamide; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid; (c) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; pyraclostrobin, Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Met
  • Signaling inhibitor (a) Signaling inhibitor: quinoxyphene, proquinazide; (b) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.
  • Lipid and cell membrane synthesis inhibitors (a) Phospholipid biosynthesis, methyltransferase inhibitor: 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) Microorganisms that disrupt the pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain; (e) Agent that disturbs 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: Triphorine; Pyrifenox, Pyrioxazole; Phenarimol, Flurprimidol, Nuarimol; Imazalyl, Imazaryl Sulfate, Oxpoconazole, Pefrazoate, Prochloraz, Triflumizole 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
  • Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole; (b) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl.
  • Host plant resistance inducer (a) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl; (b) Others: Probenazole; thiazinyl; isotianil; laminarin;
  • 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, Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; diclofluuride, tolylfluanid; guazatine, iminoctadine acetate, iminoctadine albecate (iminoctadine trialbesilate); anilazine; dithianon; quinomethionate;
  • plant regulators that can be used in combination or in combination with the pest control agent of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1 -Naphtylacetamide, Ethiclozate, Cloxiphonac, Maleic acid hydrazide, 2,3,5-Triiodobenzoic acid
  • the endoparasite control agent or pesticide of the present invention contains at least one selected from the amide compounds of the present invention as an active ingredient.
  • the compound of the present invention can be used in an amount (pharmacologically effective amount) of 0.01 to 1000 mg per 1 kg of the host animal.
  • the endoparasite control agent or pesticide of the present invention is not particularly limited by the dosage form. Dosage forms include powders, granules, tablets, capsules, pour-on formulations, spot-on formulations, emulsions, sprays, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal injections, etc.), wafers , Biscuits, minced meat and the like.
  • the endoparasite control or control agent of the present invention may contain only the amide compound of the present invention, a carrier such as a liquid carrier, a gaseous carrier, a solid carrier, a surfactant as necessary, Other adjuvants may be further contained. Further, the endoparasite control or control agent of the present invention may be obtained by impregnating a base material such as a porous ceramic plate or a nonwoven fabric with the amide compound of the present invention.
  • Parasites that are targets of the endoparasite control or pesticide of the present invention parasitize in host animals, particularly warm-blooded animals and fish (endoparasites).
  • a host animal in which the parasite control or control agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats), laboratory animals (e.g., mice, rats, gerbils, etc.) Pets (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalos, etc.), poultry (turkeys, ducks, chickens, quails, Warm-blooded animals such as geese and pet birds (eggs, parrots, nine-birds, wild birds, parakeets, juvenile pine, canaries, etc.); and fishes such as salmon, trout, and swordfish.
  • Parasites to be controlled or controlled include the following: (1) Nematodes of Dioctophymatida (a) nematodes of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp .; (b) Nematodes of the family Soboliphymatidae, for example, Soboliphyme abei, Soboliphyme baturini, of the species Soboliphyme spp.
  • Trichocephalida nematodes (a) Trichinellidae Trichinella, for example, Trichinella spiralis from Trichinella spp .; (b) Trichuridae Trichuridae, for example, Capillaria spp. Capillaria annulata, Capillaria contorta, Capillary contorta Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
  • Trichinellidae Trichinella for example, Trichinella spiralis from Trichinella spp .
  • Trichuridae Trichuridae for example, Capillaria spp. Capillaria annulata, Capillaria contorta, Capillary contorta Capillaria
  • Rhabditida nematodes For example, Strongyloides papillosus, cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
  • Ancylostomatidae worms for example, Ancylostoma spp., Ancylostoma braziliense, Ancylostoma caninum, Zubini worms (Ancylostoma duodenale), cat helminth (Ancylostoma tubaeforme); Uncinaria spp., Uncinaria stenocephala; Bunostomum spp. (Bunostomum trigonocephalum).
  • Strongylida nematodes (a) nematodes of the family Angiostrongylidae, for example, Aelurostrongylus spp., cat lungworm (Aelurostrongylus abstrusus); Schistosomiasis (Angiostrongylus vasorum), Cantonese schistosomiasis (Angiostrongylus cantonesis); (b) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp .; (c) Filaroididae nematodes, for example, Filaroides hirthi, Filaroides osleri of Filaroides spp .; (d) Pneumoides of the family Pneumolidae (Metastrongylidae), for example, Metastrongylus aprius, Metastrongylus asymmetricus
  • Strongylida nematodes (a) Nematodirus filicollis, Nematodirus spathiger from the nematodes of the Molineidae family, for example, Nematodirus spp .; (b) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Bovine lungworm (Dictyocaulus viviparus); (c) Haemonchidae nematodes, for example, Haemonchus spp., Haemonchus contortus; Mexistocirrus spp.
  • Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, the intestinal nodules of the Chabertia ovina; the intestinal nodules (Oesophagostomum spp.) of the genus Chabertia spp.
  • elegans for example, from the species of the genus Strongylus spp., Strongylus asini, edentulous (Strongylus edentatus), Strongylus equinus , Strongylus vulgaris.
  • Oxyurida nematodes Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris of Enterobius spp. spp.), Oxyuris equi; Passalurus spp., Passalurus ambiguus.
  • Nematode of Ascaridida (a) Acaridiidae nematodes, for example, Ascaridia galli from the genus Ascaridia spp .; (b) Heterakidae nematodes such as Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis spp.
  • Anisakidae nematodes for example, Anisakis simplex from Anisakis spp .;
  • Nematodes of Ascarididae for example, Ascaris lumbricoides, Ascaris suum; Ascaris suum; Parascaris spp. (Parascaris equorum);
  • Toxocaridae nematodes for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasum, Toxocara vitulorum ), Toxocara cati.
  • Spirurida nematodes (a) Nematodes of Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria spp.
  • Nematodes of the Setariidae family for example, Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa , Setaria marshalli; Wuchereria spp., Wuchereria bancrofti;
  • Filariidae nematodes for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
  • Spirurida nematodes (a) Nematodes of the Gnathostomatidae family, for example, Gnathostoma doloresi, Gnathostoma spinigerum of Gnathostoma spp .; (b) Nematodes of the family Habronematidae (Habronema spp.), for example, Habronema majus, Habronema microstoma, Habronema muscae; From the genus Species (Draschia spp.); (c) Nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis,
  • Thelaziidae nematodes such as Thelazia spip., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini).
  • Step 1-3 Ethyl 2-methyl-2- (3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) propanoate: Compound 19 To a solution of compound 18 (6.04 g) in THF (40 ml) was added ethyl 2-amino-2-methylpropionate (2.93 g), and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 19 (4.21 g, yield 62%).
  • Step 1-4 Ethyl 2- (3-ethyl-3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) -2-methylpropanoate: Compound 20 Compound 19 (4.21 g) was dissolved in DMF (40 ml), potassium carbonate (4.18 g) and iodoethane (1.97 g) were added, and the mixture was stirred for 5 hours under ice cooling. After completion of the reaction, ethyl acetate was added and washed with an aqueous ammonium chloride solution. The organic layer was dried over magnesium sulfate and filtered, and then the solvent was distilled off under reduced pressure.
  • Step 1-6 2- (3-Ethyl-3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) -N-isobutyl-2-methylpropanamide: Compound 22 (Compound No. 1-5) To a solution of compound 21 (0.20 g) in acetonitrile (10 ml) were added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 22 (0.21 g, yield 91%).
  • Step 2-2 2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanoic acid: Synthesis of Compound 12 Lithium hydroxide monohydrate in a THF / methanol / water (32ml / 8ml / 8ml) solution of Compound 11 (6.95g) The Japanese product (1.13 g) was added and stirred overnight. After completion of the reaction, 7% HCl (14.1 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure.
  • Step 2-3 Methyl 2-methyl-2- (2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamido) propanoate: Synthesis of Compound 13 Compound 12 (2.50 g) in DMSO (30 ml) solution in diisopropylethylamine (7.76 g), 2-amino-2-methylpropionic acid methyl hydrochloride (1.69 g) and TBTU (5.14 g) were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into aqueous ammonium chloride and extracted with ethyl acetate.
  • Step 2-4 Methyl 2-methyl-2- (2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamido) propanoic acid: Synthesis of Compound 14 Compound 13 (8.44 g) in THF / methanol / water (60 ml / 15 ml Lithium hydroxide monohydrate (1.36 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (17.0 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure.
  • Step 2-5) N- [1- (Isobutylamino) -2-methyl-1-oxopropan-2-yl] -2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamide: Synthesis of Compound 15 Compound 14 (0.20 g ) In acetonitrile (10 ml) was added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain Compound 15 (Compound No.
  • Ethyl 4-bromo-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate Synthesis of Compound 2 2-Bromo-3-methyl-4-nitropyridine (16.5 g) is dissolved in THF (70 ml). , Ethyl glyoxyate (47% toluene solution: 24.7 g) and TBAF (1M THF solution: 190 ml) were added, and the mixture was stirred at room temperature for 2 days. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate.
  • Step 3-2 Ethyl 4-bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 3 A THF (241 ml) solution of Compound 2 (9.36 g) was cooled to -78 ° C. , HMPA (6.16 g) and EtI (6.44 g) were added, and NaHMDS (1.9 M: 21.7 ml) was added dropwise. After stirring at ⁇ 78 ° C. for 30 minutes, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate.
  • Step 3-3) 4-Bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylic acid: Synthesis of Compound 4 Compound 3 (2.99 g) in THF / MeOH / H 2 O (32 ml / 8 ml / 8 ml) Lithium hydroxide monohydrate (0.46 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (5.74 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer for drying and filtration, and then the solvent was distilled off under reduced pressure to obtain Compound 4 (2.99 g).
  • Step 3-5 4-Bromo-2-ethyl-N- ⁇ 2- [4- (ethylsulfonyl) pyridin-2-yl] propan-2-yl ⁇ -2,3-dihydrofuro [3,2-c] pyridine-2-carboxamide: Synthesis of Compound 6 Compound 5 was dissolved in 60 ml of dichloromethane, mCPBA (3.85 g) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, an aqueous sodium hydrogen carbonate solution was added and extracted with dichloromethane.
  • Table 1 represents substituents in the compound represented by the formula (2-1) wherein Z is an oxygen atom and R 4 and R 5 are methyl groups.
  • Table 2 shows the substituents in the compound in which Z is an oxygen atom and R 4 and R 5 together form a ring in formula (2-1).
  • Table 3 shows the substituents in the compounds represented by formula (2-2) wherein Z is an oxygen atom or sulfur atom, R 1 is an ethyl group, and R 4 and R 5 are methyl groups.
  • Table 4 shows the substituents in the compound in which Z is an oxygen atom in formula (3).
  • n D melting point
  • Et is an ethyl group
  • n Pr is a normal propyl group
  • i Pr is an isopropyl group
  • c Pr is a cyclopropyl group
  • n Bu is a normal butyl group
  • s Bu is a secondary butyl group
  • t Bu is tertiary butyl.
  • c Bu represents a cyclobutyl group
  • n Pen represents a normal pentyl group
  • i Pen represents an isopentyl group
  • c Hex represents a cyclohexyl group.
  • Formulation Example 1 (wettable powder) 40 parts of amide compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate were uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient. .
  • Formulation Example 2 (Emulsion) 30 parts of the amide compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether were mixed and dissolved to obtain an emulsion of 30% active ingredient.
  • Formulation Example 3 (Emulsion) 5 parts of the amide compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain an emulsion containing 5% active ingredient.
  • Formulation Example 4 5 parts of the amide compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated into granules having a diameter of 0.5 to 1.0 mm As a result, granules having an active ingredient content of 5% were obtained.
  • Formulation Example 5 (Granule) After 5 parts of the amide compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and kneaded well, followed by granulation drying As a result, granules having an active ingredient content of 5% were obtained.
  • Formulation Example 6 (Suspension) Mix 10 parts of the amide compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water to reduce the particle size to 3 ⁇ m A wet pulverizing agent was obtained until the suspension became 10% active ingredient.
  • Formulation Example 7 (Granule) 5 parts of the amide compound of the present invention was dissolved in an organic solvent to obtain a solution. The solution was sprayed on 94 parts of kaolin and 1 part of white carbon, and then the solvent was evaporated under reduced pressure to obtain granules. This type of granule can also be used in admixture with animal food.
  • Formulation Example 8 (Injection) 0.1 to 1 part of the amide compound of the present invention and 99 to 99.9 parts of peanut oil were uniformly mixed, and then sterilized by filtration through a sterilizing filter to obtain an injection.
  • Formulation Example 11 (Spray agent) A spray agent was obtained by uniformly mixing 1 part of the amide compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol.
  • test examples show that the compound of the present invention is useful as an active ingredient of an acaricide or an endoparasite control agent.
  • ppm indicates weight ppm.
  • Test Example 2 Efficacy test against nymph spider mites Kidney seedlings were bred in 3 inch pots, and 8 adult nymph mite from Aomori Prefecture were inoculated on primary leaves. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of ticks were examined when 10 days had elapsed since the application of the drug. The test was performed in duplicate.
  • the compounds shown in Table 8 were tested for potency against citrus red mite. All the compounds showed an insecticidal rate of 90% or more against citrus red mite.
  • Test Example 4 Efficacy test 2 against citrus mite Eight female citrus red spider mites from Kanagawa Prefecture were inoculated on the mandarin orange leaves placed in the petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the tangerine leaves in a rotary spray tower. The tangerine leaf was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
  • Test Example 5 Efficacy test against apple spider mite Eight female spider mites from Aomori Prefecture were inoculated on apple leaves placed in a petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This medicine was sprayed on the apple leaves in a rotary spray tower. The apple leaves were placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
  • the compounds shown in Table 10 were tested for efficacy against apple spider mites. All the compounds showed an insecticidal rate of 90% or more against apple spider mites.
  • Test Example 6 Efficacy test against urticae (seed treatment test) 0.1 g of each of the compounds of the present invention was dissolved in 2 mL of acetone to prepare a test chemical solution. 10 g of soybean seeds were added to the test chemical solution, air-dried, and 20 seeds were sown in a planter. After being kept in a greenhouse at 25 ° C. for 7 days, the planter was inoculated with 10 females / strain of female spider mite (Tetranychus urticae). 14 days after the inoculation, the number of spider mite parasites was investigated, and the control rate was determined by the following formula. The test was performed in duplicate.
  • Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
  • Nc Number of surviving mites in the untreated group
  • Nt Number of surviving mites in the treated group
  • the compounds Nos. 1-6 and 3-28 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
  • Test Example 7 Efficacy test against urticae (soil irrigation test)
  • the emulsion of Formulation Example 3 was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm.
  • a plastic potted kidney bean seedling (primary leaf stage) was irrigated with 25 ml of chemical solution and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%.
  • Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
  • Nc Number of surviving mites in the untreated group
  • Nt Number of surviving mites in the treated group
  • the compounds Nos. 3-28 and 3-53 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
  • Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
  • Nc Number of surviving ticks in untreated group
  • Nt Number of surviving ticks in treated group
  • Compound Nos. 1-6, 1-15, 3-27, 3-28, 3-53, 3-71 went. All the compounds showed a control rate of 90% or more against the spider mite.
  • Microscopic examination includes assessment of mortality, injury, motility, progression of development and neutral red uptake by larvae compared to DMSO controls.
  • Biological activity was defined by the minimum effective concentration (“MEC”), the concentration at which at least one of the larvae exhibited death, injury, changes in motility, changes in developmental progression or no neutral red uptake.
  • MEC minimum effective concentration
  • the compounds shown in Table 11 were subjected to in vitro efficacy tests against Ascaridia galli and Oesophagostomum dentatum. All of the compounds showed activity against one or more target parasites at an MEC of 25 ⁇ M or less.
  • the amide compound of the present invention has no phytotoxicity to crops and can effectively control pests that are problematic in crops and sanitation, especially mites and pests.

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Abstract

This pest control agent includes the compound represented by formula (1) or a salt thereof (in the formula: Z represents an oxygen or sulfur atom; B is represented by formula (B-1) when A is represented by formula (A-1); B is represented by formula (B-2) when A is represented by formula (A-2); W represents a nitrogen atom, or the like; * represents a bond position; X represents a halogen group, or the like; n represents any integer from 0 to 3; R1 represents an alkyl group, or the like; R2 and R3 represent an alkyl group, or the like; R4 and R5 represent an alkyl group; R6 represents an aminocarbonyl group, or the like; and R7 represents an aminocarbonyl group, or the like).

Description

アミド化合物および有害生物防除剤Amide compounds and pest control agents
　本発明はアミド化合物および有害生物防除剤に関する。より詳細に、本発明は、優れた殺ダニ活性および／または殺虫活性を有し、安全性に優れ、且つ工業的に有利に合成できるアミド化合物、ならびにこれを有効成分として含有する有害生物防除剤に関する。
　本願は、２０１５年１０月２１日に日本に出願された特願２０１５－２０７０８０号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to an amide compound and a pest control agent. More specifically, the present invention relates to an amide compound which has excellent acaricidal activity and / or insecticidal activity, is excellent in safety, and can be synthesized industrially advantageously, and a pest control agent containing this as an active ingredient About.
This application claims priority based on Japanese Patent Application No. 2015-207080 filed in Japan on October 21, 2015, the contents of which are incorporated herein by reference.
　本発明のアミド化合物に構造上関連する化合物として、特許文献１、特許文献２、および特許文献３にアリールオキシウレア類およびアリールオキシ酢酸アミド類が開示されている。 Patent Literature 1, Patent Literature 2, and Patent Literature 3 disclose aryloxyureas and aryloxyacetic acid amides as compounds structurally related to the amide compound of the present invention.
ＷＯ２０１２／０５００４１ＡWO2012 / 050041A ＷＯ２０１３／１２２０４１ＡWO2013 / 122041A ＷＯ２０１３／１５４０８０ＡWO2013 / 154080A
　本発明の課題は、有害生物防除活性、その中でも特に殺ダニ活性および／または殺虫活性に優れ、安全性に優れ、且つ工業的に有利に合成できるアミド化合物、ならびにこれを有効成分として含有する有害生物防除剤を提供することである。 An object of the present invention is to provide an amide compound having excellent pesticidal activity, in particular, acaricidal activity and / or insecticidal activity, excellent safety, and industrially advantageous synthesis, and harmful substances containing this as an active ingredient. It is to provide a biocontrol agent.
　上記課題を解決すべく鋭意検討した結果、以下の形態を包含する本発明を完成するに至った。
〔１〕　下記式(1)で表される化合物またはその塩。 As a result of intensive studies to solve the above problems, the present invention including the following embodiments has been completed.
[1] A compound represented by the following formula (1) or a salt thereof.
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
　式(1)中、
　Ｚは、酸素原子または硫黄原子である。
　Ａは、式(A-1)で表される基、または式(A-2)で表される基である。
　Ｂは、Ａが式(A-1)で表される基あるとき式(B-1)で表される基であり、Ａが式(A-2)で表される基であるとき式(B-2)で表される基である。 In formula (1),
Z is an oxygen atom or a sulfur atom.
A is a group represented by the formula (A-1) or a group represented by the formula (A-2).
B is a group represented by the formula (B-1) when A is a group represented by the formula (A-1), and B is a group represented by the formula (A-2) It is a group represented by B-2).
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
　式(A-1)中、Ｗは窒素原子、またはＣＨである。
　式(A-1)、および(A-2)中、
　＊は結合位置を表す。
　Ｘは、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、アミノ基、置換若しくは無置換のＣ１～６アルキルアミノ基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシイミノＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ１～６アルコキシスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のヘテロアリールオキシ基、ニトロ基、またはシアノ基である。
　ｎは、Ｘの置換数を示し且つ０～３のいずれかの整数である。ｎが２または３のときＸは互いに同じでも異なってもよい。
　Ｒ1は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、またはフェニル基である。
　Ｒ2およびＲ3は、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１～６アルキル基である。 In the formula (A-1), W is a nitrogen atom or CH.
In formulas (A-1) and (A-2),
* Represents a bonding position.
X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy Group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted A C1-6 alkoxysulfonyl group, substituted or unsubstituted C3-8 cycloal Group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted heteroaryloxy group, nitro group, or cyano It is a group.
n represents the number of substitutions of X and is an integer from 0 to 3. When n is 2 or 3, Xs may be the same or different.
R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a phenyl group.
R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
　式(B-1)および(B-2)中、
　＊は結合位置を示す。
　Ｒ4およびＲ5は、それぞれ独立して、水素原子、または無置換のＣ１～６のアルキル基である。
　Ｒ4およびＲ5は繋がって、それらが結合する炭素原子とともに環を形成してもよい。
　Ｒ6は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のアミノチオカルボニル基である。
　Ｒ7は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のヘテロアリール基である。
〔２〕　式(1)が、式(2)である、〔１〕に記載の化合物またはその塩。 In formulas (B-1) and (B-2),
* Indicates a binding position.
R 4 and R 5 are each independently a hydrogen atom or an unsubstituted C 1-6 alkyl group.
R 4 and R 5 may be joined together to form a ring together with the carbon atom to which they are attached.
R 6 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
R 7 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted heteroaryl group.
[2] The compound or salt thereof according to [1], wherein formula (1) is formula (2).
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
　式(2)中、Ｚは式(1)中のそれと同じ意味を示す。
式(2)中、Ｗ、Ｘ、ｎ、Ｒ1は式(A-1)中のそれらと同じ意味を示す。
　式(2)中、Ｒ４、Ｒ５、Ｒ６は式(B-1)中のそれらと同じ意味を示す。
〔３〕　前記〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する有害生物防除剤。
〔４〕　前記〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する殺ダニ若しくは殺虫剤。
〔５〕　前記〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する内部寄生虫防除または駆除剤。 In the formula (2), Z has the same meaning as that in the formula (1).
In the formula (2), W, X, n and R 1 have the same meanings as those in the formula (A-1).
In formula (2), R 4 , R 5 and R 6 have the same meaning as in formula (B-1).
[3] A pest control agent comprising at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof as an active ingredient.
[4] An acaricide or insecticide containing as an active ingredient at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
[5] An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
　本発明のアミド化合物は、農作物や衛生面で問題となる有害生物を防除することができる。特にダニ類および害虫を効果的に防除することができる。 The amide compound of the present invention can control pests that are problematic in crops and hygiene. In particular, mites and pests can be effectively controlled.
　本発明のアミド化合物は、式(1)で表される化合物(以下、化合物(1)と表記することがある。)または化合物(1)の塩である。 The amide compound of the present invention is a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)) or a salt of compound (1).
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　本発明において、用語「無置換(unsubstituted)」は、母核となる基のみであることを意味する。母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換」の意味である。
　一方、用語「置換(substituted)」は、母核となる基のいずれかの水素原子が、母核と同一または異なる構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１個であってもよいし、２個以上であってもよい。２個以上の置換基は同一であってもよいし、異なるものであってもよい。 In the present invention, the term “unsubstituted” means that only the group serving as a mother nucleus. When only the name of a group serving as a mother nucleus is described, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “substituted” 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.
　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基の具体例としては、以下の基を挙げることができる。
　フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；
　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；
　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基； The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Specific examples of the group that can be a “substituent” include the following groups.
Halogeno groups such as fluoro, chloro, bromo and iodo groups;
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, 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 A C2-6 alkenyl group such as a hexenyl group, a 5-hexenyl group;
　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基；
　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、キュバニル基などのＣ３～８シクロアルキル基；
　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基、４－シクロオクテニル基などのＣ３～８シクロアルケニル基；
　フェニル基、ナフチル基などのＣ６～１０アリール基；
　ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；
　ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；
　インドリル基、ベンゾフリル基、ベンゾチエニル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノリル基、イソキノリル基、キノキサリニル基などの縮合環のヘテロアリール基；
　オキシラニル基、テトラヒドロフリル基、ジオキソラニル基、ジオキラニル基などの環状エーテル基；
　アジリジニル基、ピロリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの環状アミノ基； Ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc. A C2-6 alkynyl group of
A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cubanyl group;
A C3-8 cycloalkenyl group such as a 2-cyclopropenyl group, 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;
5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl;
A 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group;
A heteroaryl group of a condensed ring such as an indolyl group, a benzofuryl group, a benzothienyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group;
A cyclic ether group such as an oxiranyl group, a tetrahydrofuryl group, a dioxolanyl group, or a dioxylanyl group;
Cyclic amino groups such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group;
　水酸基；　オキソ基；
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；
　ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのＣ２～６アルケニルオキシ基；
　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；
　フェノキシ基、ナフトキシ基などのＣ６～１０アリールオキシ基；
　チアゾリルオキシ基、ピリジルオキシ基などの５～６員環のヘテロアリールオキシ基； Hydroxyl group; oxo group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
5- to 6-membered heteroaryloxy group such as thiazolyloxy group and pyridyloxy group;
　カルボキシル基；
　ホルミル基；　アセチル基、プロピオニル基などのＣ１～６アルキルカルボニル基；
　ホルミルオキシ基；　アセチルオキシ基、プロピオニルオキシ基などのＣ１～６アルキルカルボニルオキシ基；
　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基； Carboxyl group;
A formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group;
Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group and propionyloxy group;
A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；
　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；
　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；
３，３－ジフルオロシクロブチル基などのＣ３～６ハロシクロアルキル基；
　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基などのＣ１～６ハロアルコキシ基；
　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；
　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのＣ１～６ハロアルキルカルボニル基； 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 C3-6 halocycloalkyl group such as a 3,3-difluorocyclobutyl group;
C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group;
A C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;
A C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group;
　シアノ基；　ニトロ基；　アミノ基；
　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキルアミノ基；
　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；
　ホルミルアミノ基；　アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基などのＣ１～６アルキルカルボニルアミノ基；
　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；
　Ｓ，Ｓ－ジメチルスルホキシイミノ基などのＣ１～６アルキルスルホキシイミノ基； Cyano group; nitro group; amino group;
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;
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, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
A C1-6 alkylsulfoxyimino group such as an S, S-dimethylsulfoxyimino group;
　アミノカルボニル基；
　メチルアミノカルボニル基、ジメチルアミノカルボニル基、エチルアミノカルボニル基、ｉ－プロピルアミノカルボニル基などのＣ１～６アルキルアミノカルボニル基；
　イミノメチル基、(１－イミノ)エチル基、(１－イミノ)－ｎ－プロピル基などのイミノＣ１～６アルキル基；
　ヒドロキシイミノメチル基、(１－ヒドロキシイミノ)エチル基、(１－ヒドロキシイミノ)プロピル基などのヒドロキシイミノＣ１～６アルキル基；
　メトキシイミノメチル基、(１－メトキシイミノ)エチル基などのＣ１～６アルコキシイミノＣ１～６アルキル基； An aminocarbonyl group;
A C1-6 alkylaminocarbonyl group such as a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, an i-propylaminocarbonyl group;
Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
A C1-6 alkoxyimino C1-6 alkyl group such as a methoxyiminomethyl group and a (1-methoxyimino) ethyl group;
　メルカプト基；
　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；
　トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基；
　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；
　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；
　トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；
　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；
　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；
　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；
　トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；
　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；
　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基； A mercapto group;
C1-6 alkylthio groups 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 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as vinylthio group and allylthio group;
A C2-6 alkynylthio group such as an ethynylthio group or a propargylthio group;
A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
A C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group;
A C2-6 alkenylsulfinyl group such as an allylsulfinyl group;
A C2-6 alkynylsulfinyl group such as a propargylsulfinyl group;
A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group;
A C2-6 alkenylsulfonyl group such as an allylsulfonyl group;
A C2-6 alkynylsulfonyl group such as a propargylsulfonyl group;
　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキルシリル基；
　トリフェニルシリル基などのトリＣ６～１０アリールシリル基；
　また、これらの「置換基」は、当該置換基中のいずれかの水素原子が、異なる構造の基で置換されていてもよい。 A tri-C1-6 alkylsilyl group such as a trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
A tri-C6-10 arylsilyl group such as a triphenylsilyl group;
In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure.
　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、エトキシブチル基は、母核となる基がブチル基であり、置換基がエトキシ基であるので、Ｃ２アルコキシＣ４アルキル基に分類する。 “Terms such as“ C1-6 ”indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because a group serving as a mother nucleus is a butyl group and a substituent is an ethoxy group.
　式(1)において、Ｚは酸素原子または硫黄原子である。Ｚが酸素原子であるとき酸アミド類と呼ばれることがあり、Ｚが硫黄原子であるときチオアミド類と呼ばれることがある。
　式(１)のZが硫黄原子であるチオアミド類は、酸アミド類と比較して水溶解度が低いことから、環境中や動物生体中での移行性が小さく、安全性という観点から好ましい特徴を有する。 In the formula (1), Z is an oxygen atom or a sulfur atom. When Z is an oxygen atom, it may be called acid amides, and when Z is a sulfur atom, it may be called thioamides.
Thioamides in which Z in formula (1) is a sulfur atom have low water solubility compared to acid amides, and therefore have a low mobility in the environment and animal organisms, and are preferable from the viewpoint of safety. Have.
　式(1)において、Ａは、置換若しくは無置換のＮ－[(ピリジン－４－イル)オキシ]アミノ基、置換若しくは無置換の[(ピリジン－４－イル)オキシ]メチル基、または置換若しくは無置換の２，３－ジヒドロフロ[３，２－ｃ]ピリジン－２－イル基である。 In the formula (1), A represents a substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group, a substituted or unsubstituted [(pyridin-4-yl) oxy] methyl group, or a substituted or unsubstituted An unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group.
　Ａにおける、置換若しくは無置換のＮ－[(ピリジン－４－イル)オキシ]アミノ基、[(ピリジン－４－イル)オキシ]メチル基は、好ましくは式(A-1)で表される基である。
　Ａにおける、置換若しくは無置換の２，３－ジヒドロフロ[３，２－ｃ]ピリジン－２－イル基は、好ましくは式(A-2)で表される基である。 The substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group and [(pyridin-4-yl) oxy] methyl group in A are preferably groups represented by the formula (A-1) It is.
The substituted or unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group in A is preferably a group represented by the formula (A-2).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　式(A-1)、および (A-2)中、＊は結合位置を示す。
　式(A-1)、および (A-2)中、Ｘは、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、アミノ基、置換若しくは無置換のＣ１～６アルキルアミノ基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシイミノＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ１～６アルコキシスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のヘテロアリールオキシ基、ニトロ基、またはシアノ基である。
　ｎは、Ｘの置換数を示し且つ０～３のいずれかの整数である。ｎが２または３のときＸは互いに同じでも異なってもよい。 In formulas (A-1) and (A-2), * represents a bonding position.
In the formulas (A-1) and (A-2), X represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2˜ 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted Substituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or an unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C1-6 alkoxysulfonyl group, substituted or unsubstituted A C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted heteroaryloxy group, A nitro group or a cyano group.
n represents the number of substitutions of X and is an integer from 0 to 3. When n is 2 or 3, Xs may be the same or different.
　Ｘにおける「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the “halogeno group” in X include a fluoro group, a chloro group, a bromo group, and an iodo group.
　Ｘにおける「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などを挙げることができる。 The “C1-6 alkyl group” in X may be a straight chain or a branched chain. 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.
　Ｘにおける「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 Examples of the “C2-6 alkenyl group” in X include 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.
　Ｘにおける「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The “C2-6 alkynyl group” in X is an 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 group 1,1-dimethyl-2-butynyl group and the like.
　Ｘにおける「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、ｉ－ヘキシルオキシ基などを挙げることができる。 As the “C1-6 alkoxy group” in X, a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
　Ｘにおける「Ｃ１～６アルキルアミノ基」としては、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などを挙げることができる。 Examples of the “C1-6 alkylamino group” in X include a methylamino group, a dimethylamino group, and a diethylamino group.
　Ｘにおける「Ｃ１～６アルキルカルボニル基」としては、アセチル基、プロピオニル基などを挙げることができる。 Examples of the “C1-6 alkylcarbonyl group” in X include an acetyl group and a propionyl group.
　Ｘにおける「Ｃ１～６アルキルアミノカルボニル基」としては、メチルアミノカルボニル基、ジメチルアミノカルボニル基、エチルアミノカルボニル基、ｉ－プロピルアミノカルボニル基などを挙げることができる。 Examples of the “C1-6 alkylaminocarbonyl group” in X include a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, and an i-propylaminocarbonyl group.
　Ｘにおける「Ｃ１～６アルコキシイミノＣ１～６アルキル基」としては、メトキシイミノメチル基、(１－メトキシイミノ)エチル基などを挙げることができる。 Examples of the “C1-6 alkoxyimino C1-6 alkyl group” in X include a methoxyiminomethyl group and a (1-methoxyimino) ethyl group.
　Ｘにおける「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ１～６アルキルアミノ基」、「Ｃ１～６アルキルカルボニル基」、「Ｃ１～６アルキルアミノカルボニル基」、および「Ｃ１～６アルコキシイミノＣ１～６アルキル基」上の置換基として、好ましくは、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　シアノ基；　を挙げることができる。 “C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylamino group”, “C1-6 alkylcarbonyl group” in X , “C1-6 alkylaminocarbonyl group”, and “C1-6 alkoxyimino C1-6 alkyl group”, preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy Groups, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group, etc .; C6-10 groups such as phenyl group, naphthyl group, etc. Lumpur group; a cyano group; and the like.
　Ｘにおける「Ｃ１～６アルキルチオ基」は、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。 Examples of the “C1-6 alkylthio group” in X include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like.
　Ｘにおける「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。 Examples of the “C1-6 alkylsulfinyl group” in X include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
　Ｘにおける「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the “C1-6 alkylsulfonyl group” in X include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
　Ｘにおける「Ｃ１～６アルコキシスルホニル基」としては、メトキシスルホニル基、エトキシスルホニル基、ｔ－ブトキシスルホニル基などを挙げることができる。 Examples of the “C1-6 alkoxysulfonyl group” in X include a methoxysulfonyl group, an ethoxysulfonyl group, a t-butoxysulfonyl group, and the like.
　Ｘにおける「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、「Ｃ１～６アルキルスルホニル基」、および「Ｃ１～６アルコキシスルホニル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　シアノ基；　を挙げることができる。 As a substituent on “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkylsulfonyl group”, and “C1-6 alkoxysulfonyl group” in X, preferably a fluoro group, a chloro group Halogeno groups such as bromo group, iodo group; C1˜ 6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; cyano group;
　Ｘにおける「Ｃ３～８シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基などを挙げることができる。 Examples of the “C3-8 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
　Ｘにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基などを挙げることができる。 Examples of the “C6-10 aryl group” in X include a phenyl group and a naphthyl group.
　Ｘにおける「ヘテロアリール基」としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基(詳しくは、[１，２，３]トリアゾリル基、または[１，２，４]トリアゾリル基)、オキサジアゾリル基(詳しくは、[１，２，３]オキサジアゾリル基、[１，２，４]オキサジアゾリル基、[１，２，５]オキサジアゾリル基、または[１，３，４]オキサジアゾリル基)、チアジアゾリル基、テトラゾリル基などの５員ヘテロアリール基；　ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員ヘテロアリール基；　インドリル基、ベンゾフリル基、ベンゾチエニル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノリル基、イソキノリル基、キノキサリニル基などの縮合環のヘテロアリール基などを挙げることができる。 As the “heteroaryl group” in X, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group (for details, [1,2,3] Triazolyl group or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,3] oxadiazolyl group, [1,2,4] oxadiazolyl group, [1,2,5] oxadiazolyl group Or a [1,3,4] oxadiazolyl group), a thiadiazolyl group, a tetrazolyl group or the like; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; an indolyl group , Benzofuryl group, benzothienyl group, benzimidazolyl group, benzoxa Examples thereof include a heteroaryl group having a condensed ring such as a zolyl group, a benzothiazolyl group, a quinolyl group, an isoquinolyl group, or a quinoxalinyl group.
　Ｘにおける「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the “C6-10 aryloxy group” in X include a phenoxy group and a naphthoxy group.
　Ｘにおける「ヘテロアリールオキシ基」としては、チアゾリルオキシ基、ピリジルオキシ基などの５～６員環のヘテロアリールオキシ基を挙げることができる。 Examples of the “heteroaryloxy group” in X include 5- to 6-membered heteroaryloxy groups such as thiazolyloxy group and pyridyloxy group.
　Ｘにおける「Ｃ３～８シクロアルキル基」、「Ｃ６～１０アリール基」、「ヘテロアリール基」、「Ｃ６～１０アリールオキシ基」、および「ヘテロアリールオキシ基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　シアノ基；　を挙げることができる。 Substituents on the “C3-8 cycloalkyl group”, “C6-10 aryl group”, “heteroaryl group”, “C6-10 aryloxy group”, and “heteroaryloxy group” in X are preferably fluoro Group, chloro group, bromo group, iodo group and other halogeno groups; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group C1-6 alkyl groups such as n-pentyl group and n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as perfluoro-n-pentyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butyl group C1-6 alkoxy groups such as a xy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; A cyano group;
　式(A-1)および(A-2)中、Ｘは、ハロゲノ基、Ｃ１～６アルキル基、Ｃ１～６ハロアルキル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ１～６アルキルアミノ基、Ｃ１～６アルキルアミノカルボニル基、Ｃ１～６ハロアルキルアミノカルボニル基、Ｃ１～６アルコキシイミノＣ１～６アルキル基、Ｃ６～１０アリールＣ１～６アルコキシイミノＣ１～６アルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルホニル基、Ｃ６～１０アリール基、ヘテロアリール基、ニトロ基、またはシアノ基であることが好ましく、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、Ｃ１～６アルキルアミノ基、シアノ基、またはニトロ基であることがより好ましく、ハロゲノ基、Ｃ１～６ハロアルキル基、シアノ基であることが更に好ましい
　Ｘの置換数ｎは、１または２が好ましい。 In the formulas (A-1) and (A-2), X represents a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group C1-6 alkylamino group, C1-6 alkylaminocarbonyl group, C1-6 haloalkylaminocarbonyl group, C1-6 alkoxyimino C1-6 alkyl group, C6-10 aryl C1-6 alkoxyimino C1-6 alkyl group, A C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C6-10 aryl group, a heteroaryl group, a nitro group, or a cyano group is preferable, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group More preferably a C1-6 alkylamino group, a cyano group, or a nitro group, a halogeno group, a C1-6 haloalkyl, More preferably, it is a cyano group or a cyano group.
　式(A-1)および(A-2)中、Ｒ1は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、またはフェニル基である。
　Ｒ1における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」の具体例としては、Ｘにおいて例示したそれらと同じものを挙げることができる。 In the formulas (A-1) and (A-2), R 1 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group Or a phenyl group.
Specific examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C2-6 alkynyl group” in R 1 are the same as those exemplified for X.
　Ｒ1における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、または「Ｃ２～６アルキニル基」上の置換基としては、好ましくはハロゲノ基を挙げることができる。 The substituent on the “C1-6 alkyl group”, “C2-6 alkenyl group”, or “C2-6 alkynyl group” in R 1 is preferably a halogeno group.
　式(A-1)および(A-2)中、Ｒ1は、Ｃ１～６アルキル基、Ｃ１～６ハロアルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、フェニル基であることが好ましく、Ｃ１～６アルキル基であることがより好ましい。 In the formulas (A-1) and (A-2), R 1 is preferably a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or a phenyl group, More preferred is a C1-6 alkyl group.
　式(A-1)中、Ｗは窒素原子またはＣＨである。 In the formula (A-1), W is a nitrogen atom or CH.
　式(A-2)中、Ｒ2およびＲ3は、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１～６アルキル基である。
　Ｒ2およびＲ3における「Ｃ１～６アルキル基」の具体例としては、Ｘにおいて例示したそれと同じものを挙げることができる。
　Ｒ2およびＲ3における「Ｃ１～６アルキル基」上の置換基としては、好ましくはハロゲノ基を挙げることができる。
　式(A-2)中、Ｒ2またはＲ3は、水素原子であることが好ましい。 In formula (A-2), R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the “C1-6 alkyl group” for R 2 and R 3 include the same as those exemplified for X.
The substituent on the “C1-6 alkyl group” in R 2 and R 3 is preferably a halogeno group.
In formula (A-2), R 2 or R 3 is preferably a hydrogen atom.
　式(1)において、Ｂは、Ａが式(A-1)で表される基であるとき式(B-1)で表される基であり、Ａが式(A-2)で表される基であるとき式(B-2)で表される基である。 In Formula (1), B is a group represented by Formula (B-1) when A is a group represented by Formula (A-1), and A is represented by Formula (A-2). A group represented by the formula (B-2).
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
　すなわち、式(1)における、ＡとＢとの組み合わせで構成される化合物(1)は、式(2)または式(3)で表される化合物である。 That is, the compound (1) composed of a combination of A and B in the formula (1) is a compound represented by the formula (2) or the formula (3).
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
　更に式(2)は式(2-1)または式(2-2)で表される。 Furthermore, Formula (2) is expressed by Formula (2-1) or Formula (2-2).
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
　式(B-1および(B-2)中、＊は結合位置を示す。
　式(B-1)および(B-2)中、Ｒ4およびＲ5は、それぞれ独立して、水素原子、またはＣ１～６アルキル基である。Ｒ4およびＲ5におけるＣ１～６アルキル基の例としては、Ｘにおいて例示したものと同じものを挙げることができる。式(B-1)および(B-2)中、Ｒ4およびＲ5は、メチル基であることが好ましい。
　式(B-1)および(B-2)中、Ｒ4およびＲ5は繋がって、それらが結合する炭素原子とともに環を形成してもよい。Ｒ4およびＲ5が繋がって形成される環としては、シクロプロパン環、シクロブタン環、シクロヘキサン環などの炭素数３～６の脂環を挙げることができ、好ましくはシクロプロパン環である。 In the formulas (B-1 and (B-2), * indicates a bonding position.
In the formulas (B-1) and (B-2), R 4 and R 5 are each independently a hydrogen atom or a C1-6 alkyl group. Examples of the C1-6 alkyl group for R 4 and R 5 are the same as those exemplified for X. In formulas (B-1) and (B-2), R 4 and R 5 are preferably methyl groups.
In the formulas (B-1) and (B-2), R 4 and R 5 may be connected to form a ring together with the carbon atom to which they are bonded. Examples of the ring formed by connecting R 4 and R 5 include alicyclic rings having 3 to 6 carbon atoms such as a cyclopropane ring, a cyclobutane ring, and a cyclohexane ring, and a cyclopropane ring is preferable.
　式(B-1)中、Ｒ6は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のアミノチオカルボニル基である。
　式(B-2)中、Ｒ7は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のヘテロアリール基である。 In formula (B-1), R 6 represents a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
In the formula (B-2), R 7 is a substituted or unsubstituted aminocarbonyl group or a substituted or unsubstituted heteroaryl group.
　Ｒ6またはＲ7における「アミノカルボニル基」上の置換基としては、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換の(Ｃ１～６アルコキシイミノ)メチル基、またはオキセタニル基などを挙げることができる。 Examples of the substituent on the “aminocarbonyl group” in R 6 or R 7 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy. Groups, substituted or unsubstituted mono C1-6 alkylamino groups, substituted or unsubstituted diC1-6 alkylamino groups, substituted or unsubstituted (C1-6 alkoxyimino) methyl groups, or oxetanyl groups. Can do.
　Ｒ6またはＲ7における「置換アミノカルボニル基」としては、より具体的には、置換若しくは無置換のモノＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のジＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ３～６シクロアルキルアミノカルボニル基、置換若しくは無置換の環状アミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシアミノカルボニル基、置換若しくは無置換のＮ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノカルボニル基、２－モノＣ１～６アルキルヒドラジン－１－カルボニル基、２，２－ジＣ１～６アルキルヒドラジン－１－カルボニル基、置換若しくは無置換の((Ｃ１～６アルコキシイミノ)メチル)アミノカルボニル基などを挙げることができる。 More specifically, the “substituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminocarbonyl group, a substituted Or an unsubstituted C3-6 cycloalkylaminocarbonyl group, a substituted or unsubstituted cyclic aminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyaminocarbonyl group, a substituted or unsubstituted N- (C1-6 alkyl)- N- (C1-6 alkoxy) aminocarbonyl group, 2-mono C1-6 alkylhydrazine-1-carbonyl group, 2,2-diC1-6 alkylhydrazine-1-carbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) aminocarbonyl group and the like.
　Ｒ6またはＲ7における「モノＣ１～６アルキルアミノカルボニル基」としては、メチルアミノカルボニル基、エチルアミノカルボニル基、ｎ－プロピルアミノカルボニル基、ｉ－プロピルアミノカルボニル基、ｎ－ブチルアミノカルボニル基、ｓ－ブチルアミノカルボニル基、ｔ－ブチルアミノカルボニル基、ｉ－ブチルアミノカルボニル基、ｎ－ペンチルアミノカルボニル基、ｉ－ペンチルアミノカルボニル基、ｎ－ヘキシルアミノカルボニル基等を挙げることができる。 As the “mono C1-6 alkylaminocarbonyl group” in R 6 or R 7 , a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an i-propylaminocarbonyl group, an n-butylaminocarbonyl group, Examples thereof include s-butylaminocarbonyl group, t-butylaminocarbonyl group, i-butylaminocarbonyl group, n-pentylaminocarbonyl group, i-pentylaminocarbonyl group, n-hexylaminocarbonyl group and the like.
　Ｒ6またはＲ7における「ジＣ１～６アルキルアミノカルボニル基」としては、ジメチルアミノカルボニル基、メチルエチルアミノカルボニル基、ジエチルアミノカルボニル基等を挙げることができる。 Examples of the “di-C1-6 alkylaminocarbonyl group” in R 6 or R 7 include a dimethylaminocarbonyl group, a methylethylaminocarbonyl group, a diethylaminocarbonyl group and the like.
　Ｒ6またはＲ7における「Ｃ３～６シクロアルキルアミノカルボニル基」としては、シクロプロピルアミノカルボニル基、シクロブチルアミノカルボニル基、シクロペンチルアミノカルボニル基、シクロヘキシルアミノカルボニル基等を挙げることができる。 Examples of the “C3-6 cycloalkylaminocarbonyl group” in R 6 or R 7 include a cyclopropylaminocarbonyl group, a cyclobutylaminocarbonyl group, a cyclopentylaminocarbonyl group, a cyclohexylaminocarbonyl group and the like.
　Ｒ6またはＲ7における「環状アミノカルボニル基」は、アジリジニル基、ピロリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの環状アミノ基がカルボニル基と結合したものであり、具体的にはピペリジン－１－カルボニル基、ピペラジン－１－カルボニル基、ピロリジン－１－カルボニル基を挙げることができる。 The “cyclic aminocarbonyl group” in R 6 or R 7 is a group in which a cyclic amino group such as an aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a carbonyl group, specifically piperidine-1 And -carbonyl group, piperazine-1-carbonyl group, and pyrrolidine-1-carbonyl group.
　Ｒ6またはＲ7における「Ｃ１～６アルコキシアミノカルボニル基」としては、メトキシアミノカルボニル基、エトキシアミノカルボニル基、ｎ－プロポキシアミノカルボニル基等を挙げることができる。 Examples of the “C1-6 alkoxyaminocarbonyl group” in R 6 or R 7 include methoxyaminocarbonyl group, ethoxyaminocarbonyl group, n-propoxyaminocarbonyl group and the like.
　Ｒ6またはＲ7における「Ｎ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノカルボニル基」は、アミノカルボニル基の置換基としてＣ１～６アルキル基とＣ１～６アルコキシ基を有するものであり、具体的にはＮ－メチル－Ｎ－メトキシアミノカルボニル基、Ｎ－メチル－Ｎ－エトキシアミノカルボニル基等を挙げることができる。 "N- (C1-6 alkyl) -N- (C1-6 alkoxy) aminocarbonyl group" in R 6 or R 7 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents of the aminocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminocarbonyl group and N-methyl-N-ethoxyaminocarbonyl group.
　Ｒ6またはＲ7における「２－モノＣ１～６アルキルヒドラジン－１－カルボニル基」は、アミノカルボニル基の置換基として、モノＣ１～６アルキルアミノ基を有するものであり、具体的には２－メチルヒドラジン－１－カルボニル基、２－エチルヒドラジン－１－カルボニル基等を挙げることができる。 The “2-mono C1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a mono C1-6 alkylamino group as a substituent for the aminocarbonyl group. Examples thereof include a methyl hydrazine-1-carbonyl group and a 2-ethylhydrazine-1-carbonyl group.
　Ｒ6またはＲ7における「２，２－ジＣ１～６アルキルヒドラジン－１－カルボニル基」は、アミノカルボニル基の置換基として、ジＣ１～６アルキルアミノ基を有するものであり、具体的には２，２－ジメチルヒドラジン－１－カルボニル基、２，２－ジエチルヒドラジン－１－カルボニル基等を挙げることができる。 The “2,2-diC1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a diC1-6 alkylamino group as a substituent of the aminocarbonyl group. Examples include 2,2-dimethylhydrazine-1-carbonyl group, 2,2-diethylhydrazine-1-carbonyl group, and the like.
　Ｒ6またはＲ7における「((Ｃ１～６アルコキシイミノ)メチル)アミノカルボニル基」としては、((メトキシイミノ)メチル)アミノカルボニル基、または((エトキシイミノ)メチル)アミノカルボニル基が挙げられる。 Examples of the “(((C1-6 alkoxyimino) methyl) aminocarbonyl group” in R 6 or R 7 include a ((methoxyimino) methyl) aminocarbonyl group or a ((ethoxyimino) methyl) aminocarbonyl group.
　Ｒ6またはＲ7における「置換若しくは無置換のアミノカルボニル基」は、置換若しくは無置換のモノＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ３～６シクロアルキルアミノカルボニル基、置換若しくは無置換の環状アミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシアミノカルボニル基、置換若しくは無置換の((Ｃ１～６アルコキシイミノ)メチル)アミノカルボニル基が好ましく、より好ましくは、置換若しくは無置換のモノＣ１～６アルキルアミノカルボニル基または置換若しくは無置換のＣ３～６シクロアルキルアミノカルボニル基が好ましい。 The “substituted or unsubstituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group, substituted or unsubstituted. A cyclic aminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyaminocarbonyl group, a substituted or unsubstituted ((C1-6 alkoxyimino) methyl) aminocarbonyl group, and more preferably a substituted or unsubstituted monocarbonyl group. A C1-6 alkylaminocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group is preferred.
　Ｒ6またはＲ7における「モノＣ１～６アルキルアミノカルボニル基」、「ジＣ１～６アルキルアミノカルボニル基」、「Ｃ３～６シクロアルキルアミノカルボニル基」、「環状アミノカルボニル基」、「Ｃ１～６アルコキシアミノカルボニル基」、「Ｎ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノカルボニル基」、「２－モノＣ１～６アルキルヒドラジン－１－カルボニル基」、「２，２－ジＣ１～６アルキルヒドラジン－１－カルボニル基」、「((Ｃ１～６アルコキシイミノ)メチル)アミノカルボニル基」上の置換基(以下Ｇ１とする)としては、Ｃ２～６アルケニル基、Ｃ２～６ハロアルケニル基、Ｃ２～６アルキニル基、Ｃ２～６ハロアルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、Ｃ３～６ハロシクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルスルホニル基、Ｃ６～１０アリール基、５員環のヘテロアリール基、６員環のヘテロアリール基、縮合環のヘテロアリール基、ハロゲノ基、シアノ基を挙げることができる。 “Mono C1-6 alkylaminocarbonyl group”, “Di-C1-6 alkylaminocarbonyl group”, “C3-6 cycloalkylaminocarbonyl group”, “Cyclic aminocarbonyl group”, “C1-6” in R 6 or R 7 "Alkoxyaminocarbonyl group", "N- (C1-6 alkyl) -N- (C1-6 alkoxy) aminocarbonyl group", "2-mono C1-6 alkylhydrazine-1-carbonyl group", "2,2- Examples of the substituent (hereinafter referred to as G 1 ) on the “di-C1-6 alkylhydrazine-1-carbonyl group” and “((C1-6 alkoxyimino) methyl) aminocarbonyl group” include C2-6 alkenyl group, C2-6 6 haloalkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkynyl Group, C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group , C6-10 aryl groups, 5-membered heteroaryl groups, 6-membered heteroaryl groups, condensed heteroaryl groups, halogeno groups, and cyano groups.
　Ｇ１における「Ｃ２～６ハロアルケニル基」としては、２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などを挙げることができる。 Examples of the “C2-6 haloalkenyl group” for G 1 include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
　Ｇ１における「Ｃ２～６ハロアルキニル基」としては、４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などを挙げることができる。 Examples of the “C2-6 haloalkynyl group” in G 1 include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group, and the like.
　Ｇ１における「Ｃ１～６ハロアルコキシ基」としては、２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基などを挙げることができる。 Examples of the “C1-6 haloalkoxy group” in G 1 include 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, and the like. Can do.
　Ｇ１における「Ｃ３～６ハロシクロアルキル基」としては、３，３－ジフルオロシクロブチル基などを挙げることができる。 Examples of the "C3 ~ 6 halocycloalkyl group" in G 1, and the like 3,3-difluoro-cyclobutyl group.
　Ｇ１における「Ｃ１～６ハロアルキルチオ基」としては、トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などを挙げることができる。 Examples of the “C1-6 haloalkylthio group” for G 1 include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
　Ｇ１における「Ｃ１～６ハロアルキルスルフィニル基」としては、トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などを挙げることができる。 Examples of the “C1-6 haloalkylsulfinyl group” in G 1 include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
　Ｇ１における「Ｃ１～６ハロアルキルスルホニル基」としては、トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などを挙げることができる。 Examples of the “C1-6 haloalkylsulfonyl group” for G 1 include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
　Ｇ１における「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ３～６シクロアルキル基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、「Ｃ１～６アルキルスルホニル基」、「Ｃ６～１０アリール基」、「５員環のヘテロアリール基」、「６員環のヘテロアリール基」、「縮合環のヘテロアリール基」、「ハロゲノ基」としては、Ｘにおいて例示したそれと同じものが挙げられる。 “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C3-6 cycloalkyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl” in G 1 Group, C1-6 alkylsulfonyl group, C6-10 aryl group, 5-membered heteroaryl group, 6-membered heteroaryl group, condensed heteroaryl group, Examples of the “halogeno group” include the same as those exemplified for X.
　Ｇ１における「Ｃ６～１０アリール基」、「５員環のヘテロアリール基」、「６員環のヘテロアリール基」、「縮合環のヘテロアリール基」は「ハロゲノ基」で置換されていてもよい。 The “C6-10 aryl group”, “5-membered heteroaryl group”, “6-membered heteroaryl group”, and “fused-ring heteroaryl group” in G 1 may be substituted with “halogeno group” Good.
　Ｇ１としては、Ｃ２～６アルケニル基、Ｃ２～６ハロアルケニル基、Ｃ２～６アルキニル基、Ｃ２～６ハロアルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、Ｃ３～６ハロシクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルスルホニル基、(ハロゲノ基で置換されていてもよい)Ｃ６～１０アリール基、(ハロゲノ基で置換されていてもよい)５員環若しくは６員環のヘテロアリール基、ハロゲノ基、シアノ基が好ましく、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ３～６シクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、(ハロゲノ基で置換されていてもよい)Ｃ６～１０アリール基、(ハロゲノ基で置換されていてもよい)６員環のヘテロアリール基、ハロゲノ基、シアノ基がより好ましい。 G 1 includes a C2-6 alkenyl group, a C2-6 haloalkenyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group. C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, A C6-10 aryl group (which may be substituted with a halogeno group), a 5-membered or 6-membered heteroaryl group (which may be substituted with a halogeno group), a halogeno group and a cyano group are preferred, 6 alkenyl group, C2-6 alkynyl group, C1-6 alkoxy group, C3-6 cycloalkyl group, C1-6 alkenyl A thio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group, a C6-10 aryl group (which may be substituted with a halogeno group), a 6-membered hetero ring (which may be substituted with a halogeno group) An aryl group, a halogeno group, and a cyano group are more preferable.
　Ｒ6またはＲ7における特に好ましい「置換若しくは無置換のアミノカルボニル基」は、置換若しくは無置換のモノＣ１～６アルキルアミノカルボニル基(好ましい置換基Ｇ１は、Ｃ２～６アルケニル基、Ｃ２～６ハロアルケニル基、Ｃ２～６アルキニル基、Ｃ２～６ハロアルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、Ｃ３～６ハロシクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルスルホニル基、(ハロゲノ基で置換されていてもよい)Ｃ６～１０アリール基、(ハロゲノ基で置換されていてもよい)６員環のヘテロアリール基、ハロゲノ基、シアノ基であり、より好ましい置換基Ｇ１は、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ３～６シクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、(ハロゲノ基で置換されていてもよい)フェニル基、(ハロゲノ基で置換されていてもよい)ピリジル基、ハロゲノ基、シアノ基であり、Ｚが酸素原子の場合のより更に好ましい置換基Ｇ１は、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ３～６シクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、(ハロゲノ基で置換されていてもよい)フェニル基、(ハロゲノ基で置換されていてもよい)ピリジル基、シアノ基である。)、または、置換若しくは無置換のＣ３～６シクロアルキルアミノカルボニル基(好ましい置換基Ｇ１はハロゲノ基である。)である。 Particularly preferred “substituted or unsubstituted aminocarbonyl group” for R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group (preferable substituent G 1 is a C2-6 alkenyl group, C2-6 Haloalkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group , C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, optionally substituted with a halogeno group, C6-10 Aryl group, 6-membered heteroaryl group (optionally substituted with halogeno group), halogeno More preferably the substituent G 1 is a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C3-6 cycloalkyl group, a C1-6 alkylthio group, a C1-6 alkyl group. A sulfinyl group, a C1-6 alkylsulfonyl group, a phenyl group (which may be substituted with a halogeno group), a pyridyl group (which may be substituted with a halogeno group), a halogeno group or a cyano group, and Z is an oxygen atom More preferred substituents G 1 in the case of C 2-6 alkenyl group, C 2-6 alkynyl group, C 1-6 alkoxy group, C 3-6 cycloalkyl group, C 1-6 alkylthio group, C 1-6 alkyl sulfinyl group, C1-6 alkylsulfonyl group, phenyl group (which may be substituted with a halogeno group), pyridyl group (which may be substituted with a halogeno group), Or a substituted or unsubstituted C 3-6 cycloalkylaminocarbonyl group (preferably the substituent G 1 is a halogeno group).
　Ｒ6における「チオアミノカルボニル基」上の置換基としては、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換の(Ｃ１～６アルコキシイミノ)メチル基、またはオキセタニル基などを挙げることができる。 Examples of the substituent on the “thioaminocarbonyl group” in R 6 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, Examples thereof include a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted (C1-6 alkoxyimino) methyl group, or an oxetanyl group. .
　Ｒ6における「置換アミノチオカルボニル基」としては、置換若しくは無置換のモノＣ１～６アルキルアミノチオカルボニル基、置換若しくは無置換のジＣ１～６アルキルアミノチオカルボニル基、置換若しくは無置換のＣ３～６シクロアルキルアミノチオカルボニル基、置換若しくは無置換の環状アミノチオカルボニル基、置換若しくは無置換のＣ１～６アルコキシアミノチオカルボニル基、置換若しくは無置換のＮ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノチオカルボニル基、２－モノＣ１～６アルキルヒドラジン－１－チオカルボニル基、２，２－ジＣ１～６アルキルヒドラジン－１－チオカルボニル基、置換若しくは無置換の((Ｃ１～６アルコキシイミノ)メチル)アミノチオカルボニル基などを挙げることができる。 The “substituted aminothiocarbonyl group” in R 6 includes a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3 to C3— 6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted cyclic aminothiocarbonyl group, substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, substituted or unsubstituted N- (C1-6 alkyl) -N- ( C1-6 alkoxy) aminothiocarbonyl group, 2-mono C1-6 alkylhydrazine-1-thiocarbonyl group, 2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) aminothiocarbonyl group and the like.
　Ｒ6における「モノＣ１～６アルキルアミノチオカルボニル基」としては、メチルアミノチオカルボニル基、エチルアミノチオカルボニル基、ｎ－プロピルアミノチオカルボニル基、ｉ－プロピルアミノチオカルボニル基、ｎ－ブチルアミノチオカルボニル基、ｓ－ブチルアミノチオカルボニル基、ｔ－ブチルアミノチオカルボニル基、ｉ－ブチルアミノチオカルボニル基、ｎ－ペンチルアミノチオカルボニル基、ｉ－ペンチルアミノチオカルボニル基、ｎ－ヘキシルアミノチオカルボニル基等を挙げることができる。 Examples of the “mono C1-6 alkylaminothiocarbonyl group” in R 6 include a methylaminothiocarbonyl group, an ethylaminothiocarbonyl group, an n-propylaminothiocarbonyl group, an i-propylaminothiocarbonyl group, an n-butylaminothio group. Carbonyl group, s-butylaminothiocarbonyl group, t-butylaminothiocarbonyl group, i-butylaminothiocarbonyl group, n-pentylaminothiocarbonyl group, i-pentylaminothiocarbonyl group, n-hexylaminothiocarbonyl group Etc.
　Ｒ6における「ジＣ１～６アルキルアミノチオカルボニル基」としては、ジメチルアミノチオカルボニル基、メチルエチルアミノチオカルボニル基、ジエチルアミノチオカルボニル基等を挙げることができる。 Examples of the “di-C1-6 alkylaminothiocarbonyl group” in R 6 include dimethylaminothiocarbonyl group, methylethylaminothiocarbonyl group, diethylaminothiocarbonyl group and the like.
　Ｒ6における「Ｃ３～６シクロアルキルアミノチオカルボニル基」としては、シクロプロピルアミノチオカルボニル基、シクロブチルアミノチオカルボニル基、シクロペンチルアミノチオカルボニル基、シクロヘキシルアミノチオカルボニル基等を挙げることができる。 Examples of the “C3-6 cycloalkylaminothiocarbonyl group” for R 6 include a cyclopropylaminothiocarbonyl group, a cyclobutylaminothiocarbonyl group, a cyclopentylaminothiocarbonyl group, a cyclohexylaminothiocarbonyl group, and the like.
　Ｒ6における「環状アミノチオカルボニル基」は、アジリジニル基、ピロリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの環状アミノ基がチオカルボニル基と結合したものであり、具体的にはピペリジン－１－チオカルボニル基、ピペラジン－１－チオカルボニル基、ピロリジン－１－チオカルボニル基を挙げることができる。 The “cyclic aminothiocarbonyl group” in R 6 is a group in which a cyclic amino group such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a thiocarbonyl group, specifically piperidine-1- A thiocarbonyl group, a piperazine-1-thiocarbonyl group, and a pyrrolidine-1-thiocarbonyl group can be mentioned.
　Ｒ6における「Ｃ１～６アルコキシアミノチオカルボニル基」としては、メトキシアミノチオカルボニル基、エトキシアミノチオカルボニル基、ｎ－プロポキシアミノチオカルボニル基等を挙げることができる。 Examples of the “C1-6 alkoxyaminothiocarbonyl group” for R 6 include a methoxyaminothiocarbonyl group, an ethoxyaminothiocarbonyl group, an n-propoxyaminothiocarbonyl group, and the like.
　Ｒ6における「Ｎ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノチオカルボニル基」は、アミノチオカルボニル基の置換基としてＣ１～６アルキル基とＣ１～６アルコキシ基を有するものであり、具体的にはＮ－メチル－Ｎ－メトキシアミノチオカルボニル基、Ｎ－メチル－Ｎ－エトキシアミノチオカルボニル基等を挙げることができる。 “N— (C1-6 alkyl) -N— (C1-6 alkoxy) aminothiocarbonyl group” in R 6 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents for the aminothiocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminothiocarbonyl group and N-methyl-N-ethoxyaminothiocarbonyl group.
　Ｒ6における「２－モノＣ１～６アルキルヒドラジン－１－チオカルボニル基」は、アミノチオカルボニル基の置換基として、モノＣ１～６アルキルアミノ基を有するものであり、具体的には２－メチルヒドラジン－１－チオカルボニル基、２－エチルヒドラジン－１－チオカルボニル基等を挙げることができる。 The “2-mono C1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a mono C1-6 alkylamino group as a substituent of the aminothiocarbonyl group, specifically 2-methyl Examples thereof include a hydrazine-1-thiocarbonyl group and a 2-ethylhydrazine-1-thiocarbonyl group.
　Ｒ6における「２，２－ジＣ１～６アルキルヒドラジン－１－チオカルボニル基」は、アミノチオカルボニル基の置換基として、ジＣ１～６アルキルアミノ基を有するものであり、具体的には２，２－ジメチルヒドラジン－１－チオカルボニル基、２，２－ジエチルヒドラジン－１－チオカルボニル基等を挙げることができる。 The “2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a diC1-6 alkylamino group as a substituent of the aminothiocarbonyl group. 2,2-dimethylhydrazine-1-thiocarbonyl group, 2,2-diethylhydrazine-1-thiocarbonyl group, and the like.
　Ｒ6における「((Ｃ１～６アルコキシイミノ)メチル)アミノチオカルボニル基」としては、((メトキシイミノ)メチル)アミノチオカルボニル基、または((エトキシイミノ)メチル)アミノチオカルボニル基が挙げられる。
　Ｒ6における「置換若しくは無置換のアミノチオカルボニル基」は、置換若しくは無置換のモノＣ１～６アルキルアミノチオカルボニル基、置換若しくは無置換のＣ３～６シクロアルキルアミノチオカルボニル基、置換若しくは無置換の環状アミノチオカルボニル基、置換若しくは無置換のＣ１～６アルコキシアミノチオカルボニル基、置換若しくは無置換の((Ｃ１～６アルコキシイミノ)メチル)アミノチオカルボニル基が好ましく、より好ましくは、置換若しくは無置換のモノＣ１～６アルキルアミノチオカルボニル基または置換若しくは無置換のＣ３～６シクロアルキルアミノチオカルボニル基が好ましい。 Examples of the “((C1-6 alkoxyimino) methyl) aminothiocarbonyl group” for R 6 include a ((methoxyimino) methyl) aminothiocarbonyl group or a ((ethoxyimino) methyl) aminothiocarbonyl group.
The “substituted or unsubstituted aminothiocarbonyl group” in R 6 is a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted. A cyclic aminothiocarbonyl group, a substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, a substituted or unsubstituted ((C1-6 alkoxyimino) methyl) aminothiocarbonyl group, and more preferably a substituted or unsubstituted group. A substituted mono C1-6 alkylaminothiocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group is preferred.
　Ｒ6における「モノＣ１～６アルキルアミノチオカルボニル基」、「ジＣ１～６アルキルアミノチオカルボニル基」、「Ｃ３～６シクロアルキルアミノチオカルボニル基」、「環状アミノチオカルボニル基」、「Ｃ１～６アルコキシアミノチオカルボニル基」、「Ｎ－(Ｃ１～６アルキル)－Ｎ－(Ｃ１～６アルコキシ)アミノチオカルボニル基」、「２－モノＣ１～６アルキルヒドラジン－１－チオカルボニル基」、「２，２－ジＣ１～６アルキルヒドラジン－１－チオカルボニル基」、「((Ｃ１～６アルコキシイミノ)メチル)アミノチオカルボニル基」上の置換基(Ｇ２)としては、Ｃ２～６アルケニル基、Ｃ２～６ハロアルケニル基、Ｃ２～６アルキニル基、Ｃ２～６ハロアルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、Ｃ３～６ハロシクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルスルホニル基、Ｃ６～１０アリール基、５員環のヘテロアリール基、６員環のヘテロアリール基、縮合環のヘテロアリール基、ハロゲノ基、シアノ基を挙げることができる。これらの基の具体的な例示は、Ｇ１において例示したそれらと同じものを挙げることができる。また、Ｃ６～１０アリール基、５員環のヘテロアリール基、６員環のヘテロアリール基、縮合環のヘテロアリール基は更にハロゲノ基で置換されていてもよい。好ましいＧ２は、Ｇ１で述べたものと同じものである。 In R 6 , “mono C1-6 alkylaminothiocarbonyl group”, “di-C1-6 alkylaminothiocarbonyl group”, “C3-6 cycloalkylaminothiocarbonyl group”, “cyclic aminothiocarbonyl group”, “C1- 6 alkoxyaminothiocarbonyl group ”,“ N- (C1-6 alkyl) -N— (C1-6 alkoxy) aminothiocarbonyl group ”,“ 2-mono C1-6 alkylhydrazine-1-thiocarbonyl group ”,“ The substituent (G 2 ) on “2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group”, “((C1-6 alkoxyimino) methyl) aminothiocarbonyl group” includes C2-6 alkenyl group C2-6 haloalkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C -6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 Examples thereof include a 6-haloalkylsulfonyl group, a C6-10 aryl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a condensed heteroaryl group, a halogeno group, and a cyano group. Specific examples of these groups include the same ones as those exemplified in G 1. Further, the C6-10 aryl group, the 5-membered heteroaryl group, the 6-membered heteroaryl group, and the condensed heteroaryl group may be further substituted with a halogeno group. Preferred G 2 is the same as described in G 1 .
　Ｒ6における特に好ましい「置換若しくは無置換のアミノチオカルボニル基」は、置換若しくは無置換のモノＣ１～６アルキルアミノチオカルボニル基(好ましい置換基Ｇ２は、Ｃ２～６アルケニル基、Ｃ２～６ハロアルケニル基、Ｃ２～６アルキニル基、Ｃ２～６ハロアルキニル基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、Ｃ３～６ハロシクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルスルホニル基、(ハロゲノ基で置換されていてもよい)Ｃ６～１０アリール基、(ハロゲノ基で置換されていてもよい)６員環のヘテロアリール基、ハロゲノ基、シアノ基であり、より好ましい置換基Ｇ２は、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ３～６シクロアルキル基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ６～１０アリール基、６員環のヘテロアリール基、ハロゲノ基、シアノ基である。)、または、置換若しくは無置換のＣ３～６シクロアルキルアミノチオカルボニル基(好ましい置換基Ｇ２はハロゲノ基である。)であり、より更に好ましくは、無置換のモノＣ１～６アルキルアミノチオカルボニル基である。 Particularly preferred as R 6 include "substituted or unsubstituted amino thiocarbonyl group" is substituted or unsubstituted mono- C1 ~ 6 alkylaminothiocarbonyl group (preferred substituents G 2 are, C2 ~ 6 alkenyl group, C2 ~ 6 halo Alkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, C6-10 aryl (which may be substituted with a halogeno group) A 6-membered heteroaryl group (optionally substituted with a halogeno group), a halogeno group A cyano group, more preferred substituents G 2 are, C2 ~ 6 alkenyl group, C2 ~ 6 alkynyl, C1 ~ 6 alkoxy group, C3 ~ 6 cycloalkyl, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinyl Group, C1-6 alkylsulfonyl group, C6-10 aryl group, 6-membered heteroaryl group, halogeno group, cyano group), or substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group ( A preferred substituent G 2 is a halogeno group.), More preferably an unsubstituted mono C 1-6 alkylaminothiocarbonyl group.
　Ｒ7における「ヘテロアリール基」としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；インドリル基、ベンゾフリル基、ベンゾチエニル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノリル基、イソキノリル基、キノキサリニル基などの縮合環のヘテロアリール基；などを挙げることができる。
　Ｒ7における「ヘテロアリール基」は、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基が好ましく、ピリジル基またはピリミジニル基がより好ましく、ピリジン－２－イル基またはピリミジン－２－イル基が更に好ましい。
　Ｒ7における「ヘテロアリール基」は、置換基を１～４個有することが好ましく、１～２個有することがより好ましい。置換基を２個以上有するとき置換基は互いに同じでも異なってもよい。
　Ｒ7がピリジン－２－イル基またはピリミジン－２－イル基の場合、置換基は４位にあることが好ましい。 Examples of the “heteroaryl group” in R 7 include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. 5-membered heteroaryl groups; pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl and other 6-membered heteroaryl groups; indolyl, benzofuryl, benzothienyl, benzoimidazolyl, benzoxazolyl Group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group and other condensed ring heteroaryl groups.
The “heteroaryl group” for R 7 is preferably a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, more preferably a pyridyl group or a pyrimidinyl group, and pyridin-2-yl More preferred is a group or a pyrimidin-2-yl group.
The “heteroaryl group” for R 7 preferably has 1 to 4 substituents, more preferably 1 to 2 substituents. When having two or more substituents, the substituents may be the same or different.
When R 7 is a pyridin-2-yl group or a pyrimidin-2-yl group, the substituent is preferably at the 4-position.
　Ｒ7における「ヘテロアリール基」上の置換基(以下Ｙとする)としては、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、アミノ基、置換若しくは無置換のＣ１～６アルキルアミノ基、カルボキシル基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシイミノＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ１～６アルコキシスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のヘテロアリールオキシ基、ニトロ基、シアノ基、アジリジニル基、ピロリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの環状アミノ基；　Ｓ，Ｓ－ジメチルスルホキシイミノ基などのＣ１～６アルキルスルホキシイミノ基などを挙げることができる。 Examples of the substituent (hereinafter referred to as Y) on the “heteroaryl group” in R 7 include a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, carboxyl group, formyl group, substituted or unsubstituted C1-6 alkyl Carbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1 -6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted Substituted C1-6 alkylsulfonyl group, substituted or unsubstituted C1-6 alkoxysulfonyl group, substituted or unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted hetero Cyclic amino groups such as aryl groups, substituted or unsubstituted C6-10 aryloxy groups, substituted or unsubstituted heteroaryloxy groups, nitro groups, cyano groups, aziridinyl groups, pyrrolidinyl groups, piperidyl groups, piperazinyl groups, morpholinyl groups A C1-6 alkylsulfoxyimino group such as an S, S-dimethylsulfoxyimino group;
　Ｙにおけるハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルアミノ基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシイミノＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ１～６アルコキシスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のヘテロアリールオキシ基としては、Ｘにおいて例示したそれらと同じものを挙げることができる。 Halogeno group in Y, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkoxy group, substituted Or an unsubstituted C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl Group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C1-6 alkoxysulfonyl group, substituted Or an unsubstituted C3-8 cycloalkyl group, substituted or unsubstituted The C6-10 aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, and substituted or unsubstituted heteroaryloxy group are the same as those exemplified for X. be able to.
　Ｙにおける「Ｃ１～６アルコキシカルボニル基」としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Examples of the “C1-6 alkoxycarbonyl group” in Y include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group. .
　Ｙにおける「Ｃ１～６アルコキシカルボニル基」上の置換基としては、好ましくは、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　シアノ基；　を挙げることができる。 The substituent on the “C1-6 alkoxycarbonyl group” in Y is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group Group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group C1-6 haloalkoxy groups such as: C6-10 aryl groups such as phenyl groups and naphthyl groups; cyano groups;
　Ｒ7における「ヘテロアリール基」上の置換基としては、Ｃ１～６ハロアルコキシ基、Ｃ１～６アルキルスルホキシイミノ基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基が好ましい。 Examples of the substituent on the “heteroaryl group” for R 7 include a C1-6 haloalkoxy group, a C1-6 alkylsulfoxyimino group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkylsulfonyl group. Is preferred.
　本発明のアミド化合物は、好ましくは、式(2)で表される化合物(以下、化合物(2)ということがある。)、もしくはその塩である。 The amide compound of the present invention is preferably a compound represented by formula (2) (hereinafter sometimes referred to as compound (2)) or a salt thereof.
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
　式(2)中、Ｚは式(1)中のそれと同じものを示す。
　式(2)中、Ｒ１、W、Ｘ、ｎは式(A-1)中のそれらと同じものを示す。
　式(2)中、Ｒ４、Ｒ５、Ｒ６は式(B-1)中のそれらと同じものを示す。 In the formula (2), Z represents the same as that in the formula (1).
In formula (2), R 1 , W, X, and n are the same as those in formula (A-1).
In the formula (2), R 4 , R 5 and R 6 are the same as those in the formula (B-1).
　本発明の化合物(1)の塩は、農園芸学的に許容される塩であれば、特に制限されない。例えば、塩酸、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；アンモニア、トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩などを挙げることができる。 The salt of the compound (1) of the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt. For example, 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 And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
　本発明のアミド化合物は、公知の手法によって得ることができる。また、化合物(1)の塩は、化合物(1)から公知の方法によって製造することができる。 The amide compound of the present invention can be obtained by a known method. The salt of compound (1) can be produced from compound (1) by a known method.
　本発明のアミド化合物の製造法の一例として、式(2-2)で表される化合物の製法例を以下に示す。 As an example of the method for producing the amide compound of the present invention, an example of a method for producing the compound represented by the formula (2-2) is shown below.
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
　４－ハロピリジン化合物に、塩基存在下、２－ヒドロキシカルボン酸エステル化合物を反応させ、２－[(ピリジン－４－イル)オキシ]カルボン酸エステル化合物を得、次いで、これを加水分解させて、２－[(ピリジン－４－イル)オキシ]カルボン酸化合物を得、これに、Ｎ－置換アミン化合物を反応させ、式(2-2)で表される化合物を得ることができる。なお、Ｈａｌはハロゲノ基である。Ｒ1aは特に制限されないが、例えばＣ１～６アルキル基である。
　また、２－ヒドロキシカルボン酸エステル化合物の代わりにＮ－ヒドロキシカルバミン酸エステル化合物を用いることによって、式(2-1)で表される化合物を得ることができる。 The 4-halopyridine compound is reacted with a 2-hydroxycarboxylic acid ester compound in the presence of a base to obtain a 2-[(pyridin-4-yl) oxy] carboxylic acid ester compound, which is then hydrolyzed to give 2 A — [(pyridin-4-yl) oxy] carboxylic acid compound is obtained, and this is reacted with an N-substituted amine compound to obtain a compound represented by the formula (2-2). Hal is a halogeno group. R 1a is not particularly limited, and is, for example, a C1-6 alkyl group.
In addition, a compound represented by the formula (2-1) can be obtained by using an N-hydroxycarbamic acid ester compound instead of the 2-hydroxycarboxylic acid ester compound.
　本発明のアミド化合物の製造法の別の一例として、式(3)で表される化合物の製法例を以下に示す。 As another example of the method for producing the amide compound of the present invention, a method for producing the compound represented by the formula (3) is shown below.
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
　３－メチル－４－ニトロピリジン化合物に２－オキソカルボン酸エステル化合物をテトラブチルアンモニウムフルオリド等の塩基または相関移動触媒の存在下で反応させることにより、２，３－ジヒドロフロ[３，２－ｃ]ピリジン－２－カルボン酸エステル化合物を得る。次いで、これを加水分解させて、(２，３－ジヒドロフロ[３，２－ｃ]ピリジン－２－カルボン酸化合物を得る。これに、Ｎ－置換アミン化合物を反応させ、式(3)で表される化合物を得る。なお、Ｒ1aは特に制限されないが、例えばＣ１～６アルキル基である。 By reacting a 2-oxocarboxylic acid ester compound with a 3-methyl-4-nitropyridine compound in the presence of a base such as tetrabutylammonium fluoride or a phase transfer catalyst, 2,3-dihydrofuro [3,2-c ] A pyridine-2-carboxylic acid ester compound is obtained. Then, this is hydrolyzed to obtain a (2,3-dihydrofuro [3,2-c] pyridine-2-carboxylic acid compound. This is reacted with an N-substituted amine compound and represented by the formula (3). In addition, R 1a is not particularly limited, but is, for example, a C1-6 alkyl group.
　本発明のアミド化合物は、植物の生育に影響する各種のダニ類などの有害生物の防除効果に優れている。本発明のアミド化合物は、作物に対する薬害がなく、魚類や温血動物への毒性が低いため、安全性の高い化合物である。本発明のアミド化合物は、殺ダニ剤の有効成分として有用である。本発明のアミド化合物は、感受性系統のダニ類だけでなく、近年問題となっている殺ダニ剤抵抗性系統のダニ類に対しても優れた防除効果を示す。 The amide compound of the present invention is excellent in controlling pests such as various mites that affect plant growth. The amide compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. The amide compound of the present invention is useful as an active ingredient of an acaricide. The amide compound of the present invention exhibits an excellent control effect not only on mites of sensitive strains but also on mite-resistant mites which have recently become a problem.
　本発明のアミド化合物は、人獣に害を及ぼす内部寄生虫の防除効果に優れている。また、薬害が少なく、魚類や温血動物への毒性が低いため、安全性の高い化合物である。そのため、内部寄生虫の防除剤の有効成分として有用である。 The amide compound of the present invention is excellent in the control effect of endoparasites that are harmful to humans and animals. 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 endoparasite control agent.
また、本発明のアミド化合物は、防除の対象となる生物のすべての発育ステージにおいて効力を示し、例えば、ダニ、昆虫などの卵、若虫、幼虫、蛹、成虫に対して優れた防除効果を示す。 In addition, the amide compound of the present invention exhibits efficacy at all stages of development of organisms to be controlled, and exhibits excellent control effects on, for example, eggs, nymphs, larvae, pupae and adults such as mites and insects. .
〔有害生物防除剤、殺ダニ若しくは殺虫剤〕
　本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、本発明のアミド化合物、すなわち化合物(1)および化合物(1)の塩から選ばれる少なくとも１つを有効成分として含有するものである。本発明の有害生物防除剤または殺ダニ若しくは殺虫剤に含まれるアミド化合物の量は有害生物の防除効果を示す限りにおいて特に制限されない。 [Pesticide, acaricide or insecticide]
The pest control agent or acaricide or insecticide of the present invention contains, as an active ingredient, at least one selected from the amide compounds of the present invention, that is, the compound (1) and the salt of the compound (1). The amount of the amide compound contained in the pest control agent or the acaricide or insecticide of the present invention is not particularly limited as long as it exhibits a pest control effect.
　本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、穀物類；野菜類；根菜類；イモ類；花卉類；果樹類、観葉植物；茶、コーヒー、カカオなどの樹木類；牧草類；芝類；ワタなどの植物に対して用いることが好ましい。
　植物への施用において、本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などのいずれの部位に用いてもよい。また、本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、施用される植物の種によって特に制限されない。植物の種としては、例えば、原種、変種、改良品種、栽培品種、突然変異体、ハイブリッド体、遺伝子組み換え体(ＧＭＯ)などが挙げられる。 The pest control agent or acaricide or insecticide of the present invention includes cereals, vegetables, root vegetables, potatoes, flowering plants, fruit trees, foliage plants, trees such as tea, coffee, cacao, grasses, turf Kind: It is preferably used for plants such as cotton.
In application to plants, the pest control agent or acaricide or insecticide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used for the part. Moreover, the pest control agent or acaricide or insecticide of the present invention is not particularly limited depending on the species of the plant to be applied. Examples of plant seeds include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).
　本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、各種のダニ類を防除するために、種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。 The pest control agent or acaricide or insecticide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various mites.
　本発明の有害生物防除剤によって防除可能な各種の農業害虫およびダニ類の具体例を以下に示す。 Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.
(１)鱗翅目(Lepidoptera)のチョウまたは蛾
(ａ)ヒトリガ科(Arctiidae)のガ、例えば、アメリカシロヒトリ(Hyphantria cunea)、クワゴマダラヒトリ(Lemyra imparilis)；
(ｂ)チビガ科(Bucculatricidae)のガ、例えば、ナシチビガ(Bucculatrix pyrivorella)；
(ｃ)シンクイガ科(Carposinidae)のガ、例えば、モモシンクイガ(Carposina sasakii)；
(ｄ)ツトガ科(Crambidae)のガ、例えば、ジアファニア属種(Diaphania spp.)の、ワタヘリクロノメイガ(Diaphania indica)、アメリカウリノメイガ (Diaphania nitidalis)；例えば、オストリニア属種(Ostrinia spp.)の、アワノメイガ(Ostrinia furnacalis)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、アズキノメイガ(Ostrinia scapulalis)；その他、ニカメイガ(Chilo suppressalis)、コブノメイガ(Cnaphalocrocis medinalis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、サウスウエスタンコンボーラー(Diatraea grandiosella)、クワノメイガ(Glyphodes pyloalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Parapediasia teterrella)；
(ｅ)キバガ科(Gelechiidae)のガ、例えば、イモキバガ(Helcystogramma triannulella)、ワタアカミムシ(Pectinophora gossypiella)、ジャガイモキバガ(Phthorimaea operculella)、バクガ(Sitotroga cerealella)；
(ｆ)シャクガ科(Geometridae)のガ、例えば、ヨモギエダシャク(Ascotis selenaria)；
(ｇ)ホソガ科(Gracillariidae)のガ、例えば、チャノホソガ(Caloptilia theivora)、ミカンハモグリガ(Phyllocnistis citrella)、キンモンホソガ(Phyllonorycter ringoniella)；
(ｈ)セセリチョウ科(Hesperiidae)のチョウ、例えば、イチモンジセセリ(Parnara guttata)；
(ｉ)カレハガ科(Lasiocampidae)のガ、例えば、オビカレハ(Malacosoma neustria)；
(ｊ)ドクガ科(Lymantriidae)のガ、例えば、リマントリア属種(Lymantria spp.)の、マイマイガ(Lymantria dispar)、ノンネマイマイ(Lymantria monacha)；その他の、チャドクガ(Euproctis pseudoconspersa)、ヒメシロモンドクガ(Orgyia thyellina)； (1) Lepidoptera butterfly or moth
(a) moths of the Arctiidae family, eg Hyphantria cunea, Lemyra imparilis;
(b) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella;
(c) moths of Carposinidae, for example, Carposina sasakii;
(d) moths of the family Craambidae, 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;
(f) Geometridae moths, for example Ascotis selenaria;
(g) moths from the family Gracillariidae, for example, Caloptilia theivora, citrus leafworm (Phyllocnistis citrella), phleglonorycter ringoniella;
(h) Hesperiidae butterflies, such as Parnara guttata;
(i) moths of the family Lasiocampidae, for example, Malocasoma neustria;
(j) Lymantriidae moths, for example, Lymantria spp., Lymantria dispar, Lymantria monacha; Other, Euproctis pseudoconspersa, Orgyia sp. thyellina);
(ｋ)モグリガ科(Lyonetiidae )のガ、例えば、リオネチア属種(Lyonetia spp.)の、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella malinella)；
(ｌ)ヤガ科(Noctuidae)のガ、例えば、スポドプテラ属種(Spodoptera spp.)の、スジキリヨトウ(Spodoptera depravata)、サザンアーミーワーム(Spodoptera eridania)、シロイチモジヨトウ(Spodoptera exigua)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカヨトウ(Spodoptera littoralis)、ハスモンヨトウ(Spodoptera litura)；例えば、オートグラファ属種(Autographa spp.)の、ガマキンウワバ (Autographa gamma)、タマナギンウワバ(Autographa nigrisigna)；例えば、アグロチス属種(Agrotis spp.)の、タマナヤガ(Agrotis ipsilon)、カブラヤガ(Agrotis segetum)；例えば、ヘリコベルパ属種(Helicoverpa spp.)の、オオタバコガ(Helicoverpa armigera)、タバコガ(Helicoverpa assulta)、コットンボールワーム(Helicoverpa zea)；例えば、ヘリオチス属種(Heliothis spp.)の、ワタキバガ (Heliothis armigera)、ニセアメリカタバコガ(Heliothis virescens)；その他の、ナカジロシタバ(Aedia leucomelas)、ミツモンキンウワバ(Ctenoplusia agnata)、アケビコノハ(Eudocima tyrannus)、ヨトウガ(Mamestra brassicae)、アワヨトウ(Mythimna separata)、フタオビコヤガ(Naranga aenescens)、マツキリガ(Panolis japonica)、ニセタマナヤガ(Peridroma saucia)、ソイビーンルーパー(Pseudoplusia includens)、イラクサギンウワバ(Trichoplusia ni)；
(ｍ)コブガ科(Nolidae) のガ、例えば、ミスジアオリンガ (Earias insulana)；
(ｎ)シロチョウ科(Pieridae)のチョウ、例えば、モンシロチョウ属種(Pieris spp.)のオオモンシロチョウ(Pieris brassicae)、モンシロチョウ(Pieris rapae crucivora)；
(ｏ)コナガ科(Plutellidae)のガ、例えば、アクロレピオプシス属種(Acrolepiopsis spp.)の、ネギコガ(Acrolepiopsis sapporensis)、ヤマノイモコガ(Acrolepiopsis suzukiella)；その他、コナガ(Plutella xylostella)；
(ｐ)メイガ科(Pyralidae)のガ、例えば、スジマダラメイガ(Cadra cautella)、モロコシマダラメイガ(Elasmopalpus lignosellus)、シロイチモジマダラメイガ(Etiella zinckenella)、ハチノスツヅリガ (Galleria mellonella)；
(ｑ)スズメガ科(Sphingidae)のガ、例えば、マンジュカ属種(Manduca spp.)の、トマトホーンワーム(Manduca quinquemaculata)、タバコホーンワーム(Manduca sexta)； (k) moths of the family Lyonetiidae, for example, Lyonetia clerkella, Lyonetia prunifoliella malinella, from the genus Lyonetia spp .;
(l) Noctuidae moths, for example, Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, ), African Spodoptera littoralis, Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotis sp. For example, Agrotis ipsilon, Agrotis segetum; for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Of the species (Heliothis spp.), Heliothis armigera, Heliothis virescens; Others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenis jacen Peridroma saucia), soy bean looper (Pseudoplusia includens), nettle wain (Trichoplusia ni);
(m) Nolidae moths, such as Misaria Olingsa (Earias insulana);
(n) Pieridae butterflies, for example, Pieris sp., Pieris brassicae, Pieris rapae crucivora;
(o) moths of the family Plutellidae, for example, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella of the genus Acrolepiopsis spp .; other, Plutella xylostella;
(p) Pyralidae moths, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(q) Sphingidae moth, for example, Manduca quinquemaculata, Manduca sexta of Manduca spp .;
(ｒ)ニセマイコガ科(Stathmopodidae)のガ、例えば、カキノヘタムシガ(Stathmopoda masinissa)；
(ｓ)ヒロズコガ科(Tineidae)のガ、例えば、イガ(Tinea translucens)；
(ｔ)ハマキガ科(Tortricidae)のガ、例えば、アドキソフィエス属種(Adoxophyes spp.)の、チャノコカクモンハマキ(Adoxophyes honmai)、リンゴコカクモンハマキ(Adoxophyes orana)；例えば、アルチプス属種(Archips spp.)の、リンゴモンハマキ(Archips breviplicanus)、ミダレカクモンハマキ(Archips fuscocupreanus)；その他の、トウヒノシントメハマキ (Choristoneura fumiferana)、コドリンガ(Cydia pomonella)、ブドウホソハマキ (Eupoecilia ambiguella)、ナシヒメシンクイ(Grapholitha molesta)、チャハマキ(Homona magnanima)、マメシンクイガ(Leguminivora glycinivorella)、ホソバヒメハマキ(Lobesia botrana)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、トビハマキ(Pandemis heparana)、テングハマキ(Sparganothis pilleriana)；
(ｕ)スガ科(Yponomeutidae)のガ、例えば、リンゴヒメシンクイ(Argyresthia conjugella)。 (r) moths of the family Stahmopodidae, for example, Stahmopoda masinissa;
(s) moths from the family Tineidae, for example tiger (Tinea translucens);
(t) Tortricidae moths, for example, Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp .; for example, Archips spp. ), Apple chips (Archips breviplicanus), Green chips leaf (Archips fuscocupreanus); ), Chamonaki (Homona magnanima), Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Spiananothis pill
(u) Yponomeutidae moth, for example, Argyresthia conjugella.
(２)アザミウマ目(Thysanoptera)害虫
(ａ)クダアザミウマ科(Phlaeothripidae)の、例えば、カキクダアザミウマ(Ponticulothrips diospyrosi)；
(ｂ)アザミウマ科(Thripidae)の、例えば、フランクリニェラ属種(Frankliniella spp.)の、ヒラズハナアザミウマ(Frankliniella intonsa)、ミカンキイロアザミウマ(Frankliniella occidentalis)；例えば、トリプス属種(Thrips spp.)の、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci)；その他の、クロトンアザミウマ(Heliothrips haemorrhoidalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)。 (2) Thysanoptera pest
(a) from the Phlaeothripidae family, for example, Ponticulothrips diospyrosi;
(b) from the Thripidae family, for example, Frankliniella intonsa, Frankliniella occidentalis; for example, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; other, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.
(３)カメムシ目(Hemiptera)の害虫
(Ａ)頸吻亜目(Archaeorrhyncha)
(ａ)ウンカ科(Delphacidae)の、例えば、ヒメトビウンカ(Laodelphax striatella)、トビイロウンカ(Nilaparvata lugens)、クロフツノウンカ(Perkinsiella saccharicida)、セジロウンカ(Sogatella furcifera)。 (3) Pests of the Hemiptera
(A) Cervical antrum (Archaeorrhyncha)
(a) From the Delphacidae family, for example, the green planthopper (Laodelphax striatella), the green planthopper (Nilaparvata lugens), the black planthopper (Perkinsiella saccharicida), and the white planthopper (Sogatella furcifera).
(Ｂ)頸吻亜目(Clypeorrhyncha)
(ａ)ヨコバイ科(Cicadellidae)の、例えば、エンポアスカ属種(Empoasca spp.)の、ジャガイモヒメヨコバイ(Empoasca fabae)、カキノヒメヨコバイ(Empoasca nipponica)、チャノミドリヒメヨコバイ(Empoasca onukii)、マメノミドリヒメヨコバイ(Empoasca sakaii)、；その他の、フタテンヒメヨコバイ(Arboridia apicalis)、ミドリナガヨコバイ(Balclutha saltuella)、フタテンオオヨコバイ(Epiacanthus stramineus)、ヒメフタテンヨコバイ(Macrosteles striifrons)、ツマグロヨコバイ(Nephotettix cinctinceps)。 (B) Clypeorrhyncha
(a) From the family of Cicadellidae, for example, Empoasca spp., Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Others ).
(Ｃ)カメムシ亜目(Heteroptera)
(ａ)ホソヘリカメムシ科(Alydidae)の、例えば、ホソヘリカメムシ(Riptortus clavatus)；
(ｂ)ヘリカメムシ科(Coreidae)の、例えば、ホソハリカメムシ(Cletus punctiger)、クモヘリカメムシ(Leptocorisa chinensis)；
(ｃ)ナガカメムシ科(Lygaeidae)の、例えば、アメリカコバネナガカメムシ (Blissus leucopterus)、カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)；
(ｄ)カスミカメムシ科(Miridae)の、例えば、クロトビカスミカメ(Halticus insularis)、サビイロカスミカメ (Lygus lineolaris)、コットンフリーホッパー(Psuedatomoscelis seriatus)、ナガムギカスミカメ(Stenodema sibiricum)、アカスジカスミカメ(Stenotus rubrovittatus)、イネホソミドリカスミカメ(Trigonotylus caelestialium)； (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 of the family Lygaeidae, for example, the American leaf beetle (Blissus leucopterus), the leaf beetle (Cavelerius saccharivorus), the leaf beetle (Togo hemipterus);
(d) From the Miridae family, for example, the black beetle turtle (Halticus insularis), the red-bellied turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the long-nosed turtle (Stenodema sibiricum), the Stellata tus rutus ), Trigonotylus caelestialium;
(ｅ)カメムシ科(Pentatomidae)の、例えば、ネザラ属種(Nezara spp.)の、アオクサカメムシ(Nezara antennata)、ミナミアオカメムシ(Nezara viridula)；例えば、シラホシカメムシ属種(Eysarcoris spp.)の、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)；その他の、ブチヒゲカメムシ(Dolycoris baccarum)、ナガメ(Eurydema rugosum)、ツヤアオカメムシ(Glaucias subpunctatus)、サギカメムシ(Halyomorpha halys)、クイチモンジカメムシ(Piezodorus hybneri)、チャバネアオカメムシ(Plautia crossota)、イネクロカメムシ(Scotinophora lurida)；
(ｆ)ホシカメムシ科(Pyrrhocoridae)の、例えば、アカホシカメムシ(Dysdercus cingulatus)；
(ｇ)ヒメヘリカメムシ科(Rhopalidae)の、例えば、アカヒメヘリカメムシ(Rhopalus msculatus)；
(ｈ)キンカメムシ科(Scutelleridae)の、例えば、ムギチャイロカメムシ(Eurygaster integriceps)；
(ｉ)グンバイムシ科(Tingidae)の、例えば、ナシグンバイ(Stephanitis nashi)。 (e) from the Pentatomidae family, for example, from the Nezara spp., Nezara antennata, Nezara viridula; eg, from the Eysarcoris spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis; Others, Dolycoris baccarum, Eurydema rugous moth 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 Tingidae family, for example, Stephanitis nashi.
(Ｄ)腹吻亜目(Sternorrhyncha)
(ａ)カサアブラムシ科(Adelgidae)の、例えば、カラマツカサアブラムシ(Adelges laricis)；
(ｂ)コナジラミ科(Aleyrodidae)例えば、ベミシア属種(Bemisia spp.)の、シルバーリーフコナジラミ(Bemisia argentifolii)、タバココナジラミ(Bemisia tabaci)；その他の、ミカントゲコナジラミ(Aleurocanthus spiniferus)、ミカンコナジラミ(Dialeurodes citri)、オンシツコナジラミ(Trialeurodes vaporariorum)；
(ｃ)アブラムシ科(Aphididae)、例えば、アフィス属種(Aphis spp.)の、マメアブラムシ(Aphis craccivora)、マメクロアブラムシ(Aphis fabae)、イチゴネアブラムシ(Aphis forbesi)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ニワトコアブラムシ(Aphis sambuci)、ユキヤナギアブラムシ(Aphis spiraecola)；例えば、ロパロシフム属種(Rhopalosiphum spp.)の、トウモロコシアブラムシ(Rhopalosiphum maidis)、ムギクビレアブラムシ(Rhopalosiphum padi)；例えば、ジサフィス属種(Dysaphis spp.)の、オオバコアブラムシ(Dysaphis plantaginea)、ギシギシネアブラムシ(Dysaphis radicola)；例えば、マクロシフム属種(Macrosiphum spp.)の、ムギヒゲナガアブラムシ(Macrosiphum avenae)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)；例えば、ミズス属種(Myzus spp.)の、ニワウメクロコブアブラムシ (Myzus cerasi)、モモアカアブラムシ(Myzus persicae)、カワリコブアブラムシ(Myzus varians)；その他の、エンドウヒゲナガアブラムシ(Acyrthosiphon pisum)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、イチゴケナガアブラムシ(Chaetosiphon fragaefolii)、モモコフキアブラムシ(Hyalopterus pruni)、チシャミドリアブラムシ(Hyperomyzus lactucae)、ニセダイコンアブラムシ(Lipaphis erysimi)、ソラマメヒゲナガアブラムシ(Megoura viciae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、レタスアブラムシ(Nasonovia ribis-nigri)、ホップイボアブラムシ(Phorodon humuli)、ムギミドリアブラムシ(Schizaphis graminum)、ムギヒゲナガアブラムシ(Sitobion avenae)、コミカンアブラムシ(Toxoptera aurantii)； (D) Sternorrhyncha
(a) from the family Adelgidae, for example, Adelges laricis;
(b) Aleyrodidae, for example, Bemisia spp., Silver leaf whiteflies (Bemisia argentifolii), Tobacco whiteflies (Bemisia tabaci); Others citri), Trialeurodes vaporariorum;
(c) Aphididae, for example, from Aphis spp., Aphis craccivora, bean aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii) , European apple aphids (Aphis pomi), elder-core aphids (Aphis sambuci), Aphis spiraecola; for example, Rhopalosiphum spp. For example, from the genus Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; for example, Macrosiphum spp., Macrosiphum avenae, aphid (Macrosiphum euphorbiae); e.g. Myzus spp. Mussels (Myzus cerasi), peach aphids (Myzus persicae), myrtle aphids (Myzus varians); other, pea beetle aphids (Acyrthosiphon pisum), potato beetles Aphids (Brevicoryne brassicae), strawberry aphids (Chaetosiphon fragaefolii), peach beetles (Hyalopterus pruni), Hyperomyzus lactucae, black-headed aphids (Lipaphis erysimi), ura aphids Aphids (Metopolophium dirhodum), lettuce aphids (Nasonovia ribis-nigri), hops aphids (Phorodon humuli), barley aphids (Schizaphis graminum), barley aphids (Sitobion avenae), comican aphids (Toxera)
(ｄ)カタカイガラムシ科(Coccidae)の、例えば、セロプラスター属種(Ceroplastes spp.)の、ツノロウムシ(Ceroplastes ceriferus)、ルビーロウムシ(Ceroplastes rubens)；
(ｅ)マルカイガラムシ科(Diaspididae)の、シューダウラカスピス属種(Pseudaulacaspis spp.)の、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ウメシロカイガラムシ(Pseudaulacaspis prunicola)；例えば、ウナスピス属種(Unaspis spp.)の、マサキナガカイガラムシ(Unaspis euonymi)、ヤノネカイガラムシ(Unaspis yanonensis)；その他の、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Comstockaspis perniciosa)、チャコノハカイガラムシ(Fiorinia theae)、チャノマルカイガラムシ(Pseudaonidia paeoniae)；
(ｆ)ワタフキカイガラムシ科(Margarodidae)の、例えば、オオワラジカイガラムシ(Drosicha corpulenta)、イセリアカイガラムシ(Icerya purchasi)；
(ｇ)ネアブラムシ科(Phylloxeridae)の、例えば、ブドウネアブラムシ(Viteus vitifolii)；
(ｈ)コナカイガラムシ科(Pseudococcidae )の、例えば、プラノコッカス属種(Planococcus spp.)の、ミカンコナカイガラムシ(Planococcus citri)、フジコナカイガラムシ(Planococcus kuraunhiae)；その他の、ナスコナカイガラムシ(Phenacoccus solani)、クワコナカイガラムシ(Pseudococcus comstocki)；
(ｉ)キジラミ科(Psyllidae)の、例えば、プスルラ属種(Psylla spp.)の、リンゴキジラミ(Psylla mali)、ナシキジラミ(Psylla pyrisuga)；その他の、ミカンキジラミ(Diaphorina citri)。 (d) from the family Coccidae, for example, Ceroplastes ceriferus, Ceroplastes rubens, from the genus Ceroplastes spp .;
(e) Pseudaulacaspis pentagona, Pseudaulacaspis prunicola of Pseudaulacaspis spp. from the family Diaspididae; for example, Unaspisp. , Unaspis euonymi, Unaspis yanonensis; Other, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theoni, paorie seuda );
(f) from the order of the Margarodidae, for example, Drosicha corpulenta, Icerya purchasi;
(g) from the family Aphididae (Phylloxeridae), for example, grape aphids (Viteus vitifolii);
(h) Pseudococcidae, for example, from Planococcus spp., Planococcus citri, Planococcus kuraunhiae; other, Phenacoccus solani , Pseudococcus comstocki;
(i) From the Psyllidae family, for example, Psylla mali, Psylla malis, Psylla pyrisuga; other, Diaphorina citri.
(４)カブトムシ亜目(Polyphaga)の害虫
(ａ)シバンムシ科(Anobiidae)の、例えば、タバコシバンムシ(Lasioderma serricorne)； 
(ｂ)オトシブミ科(Attelabidae)の、例えば、ドロハマキチョッキリ(Byctiscus betulae)、モモチョッキリゾウムシ(Rhynchites heros)；
(ｃ)ナガシンクイムシ科(Bostrichidae)の、例えば、ヒラタキクイムシ(Lyctus brunneus)；
(ｄ)ミツギリゾウムシ科(Brentidae)の、例えば、アリモドキゾウムシ(Cylas formicarius)；
(ｅ)タマムシ科(Buprestidae )の、例えば、アカバナガタマムシ (Agrilus sinuatus)；
(ｆ)カミキリムシ科(Cerambycidae)の、例えば、ゴマダラカミキリ(Anoplophora malasiaca)、マツノマダラカミキリ(Monochamus alternatus)、キボシカミキリ(Psacothea hilaris)、ブドウトラカミキリ(Xylotrechus pyrrhoderus)；
(ｇ)ハムシ科(Chrysomelidae)の、例えば、ブルクス属種(Bruchus spp.)の、エンドウマメゾウムシ (Bruchus pisorum)、ソラマメゾウムシ (Bruchus rufimanus)；例えば、ジアブロチカ属種(Diabrotica spp.)の、ノーザンコーンルートワーム(Diabrotica barberi)、サザンコーンルートワーム(Diabrotica undecimpunctata)、ウエスタンコーンルートワーム(Diabrotica virgifera)；例えば、フィロトレタ属種(Phyllotreta spp.)の、ノミトビヨロイムシ(Phyllotreta nemorum)、キスジノミハムシ(Phyllotreta striolata)；その他の、ウリハムシ(Aulacophora femoralis)、アズキゾウムシ(Callosobruchus chinensis)、カメノコハムシ(Cassida nebulosa)、テンサイトビハムシ(Chaetocnema concinna)、コロラドハムシ(Leptinotarsa decemlineata)、イネクビホソハムシ(Oulema oryzae)、ナスナガスネトビハムシ(Psylliodes angusticollis)； (4) Polyphaga pests
(a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne);
(b) from the family Attelabidae, for example, Byctiscus betulae, Rhynchites heros;
(c) from the Bostrichidae family, for example, Lyctus brunneus;
(d) from the Brentidae family, for example, Cylas formicarius;
(e) from the Buprestidae family, for example, Agrilus sinuatus;
(f) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder;
(g) Northern corn of the Chrysomelidae family, for example, Bruchus spp., Bruchus pisorum, Bruchus rufimanus; eg, Diabrotica spp. Rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi potato beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Inkubihoso yzae (Oule) Psylliodes angusticollis;
(ｈ)テントウムシ科(Coccinellidae)の、例えば、エピラクナ属種(Epilachna spp.)の、インゲンテントウ(Epilachna varivestis)、ニジュウヤホシテントウ(Epilachna vigintioctopunctata)；
(ｉ)ゾウムシ科(Curculionidae)の、例えば、アントノムス属種(Anthonomus spp.)の、ワタミゾウムシ(Anthonomus grandis)、ナシハナゾウムシ (Anthonomus pomorum)；例えば、シトフィルスコクゾウムシ属種(Sitophilus spp.)の、グラナリーウィービル(Sitophilus granarius)、コクゾウムシ(Sitophilus zeamais)；その他の、イネゾウムシ(Echinocnemus squameus)、イモゾウムシ(Euscepes postfasciatus)、マツアナアキゾウムシ(Hylobius abietis)、アルファルファタコゾウムシ(Hypera postica)、イネミズゾウムシ(Lissohoptrus oryzophilus)、キンケクチブトゾウムシ(Otiorhynchus sulcatus)、アカアシチビコフキゾウムシ (Sitona lineatus)、シバオサゾウムシ(Sphenophorus venatus)；
(ｊ)コメツキムシ科(Elateridae)の、例えば、メラノツス属種(Melanotus spp.)の、マルクビクシコメツキ(Melanotus fortnumi)、カンシャクシコメツキ(Melanotus tamsuyensis)；
(ｋ)ケシキスイ科(Nitidulidae)の、例えば、ヒメヒラタケシキスイ(Epuraea domina)；
(ｌ)コガネムシ科(Scarabaeidae)の、例えば、アノマラ属種(Anomala spp.)の、ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)；その他の、キンイロハナムグリ(Cetonia aurata)、コアオハナムグリ(Gametis jucunda)、ナガチャコガネ(Heptophylla picea)、ヨーロッパコフキコガネ (Melolontha melolontha)、マメコガネ(Popillia japonica)；
(ｍ)キクイムシ科(Scolytidae)の、例えば、ヤツバキクイ (Ips typographus)；
(ｎ)ハネカクシ科(Staphylinidae)の、例えば、アオバアリガタハネカクシ(Paederus fuscipes)；
(ｏ)ゴミムシダマシ科(Tenebrionidae)の、例えば、チャイロコメノゴミムシダマシ(Tenebrio molitor)、コクヌストモドキ(Tribolium castaneum)；
(ｐ)コクヌスト科(Trogossitidae)の、例えば、コクヌスト(Tenebroides mauritanicus)。 (h) from the order of the Coccinellidae, for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
(i) From the Curculionidae, for example, Anthonomus spp., Anthonomus grandis, Anthonomus pomorum; for example, Sitophilus spp. , Granary weevil (Sitophilus granarius), weevil (Sitophilus zeamais); other, weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), pine weevil (Hylobius abietis), alfalfa weevil Lissohoptrus oryzophilus), Otiorhynchus sulcatus, Red-footed weevil (Sitona lineatus), Sphenophorus venatus;
(j) from the Elateridae family, for example, Melanotus fortnumi, Melanonotus tamsuyensis, from the genus Melanotus spp .;
(k) From the family Nitidulidae, for example, Epuraea domina;
(l) From the family Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Other, Cetonia aurata, Coretis ), Heptophylla picea, Melonthatha melolontha, Popillia japonica;
(m) from the Scolytidae family, for example, Ips typographus;
(n) from the family Staphylinidae, for example, Paederus fuscipes;
(o) from the Tenebrionidae family, for example, Tenebrio molitor, Tribolium castaneum;
(p) From the family Trogossitidae, for example, Tenebroides mauritanicus.
(５)ハエ目(Diptera)の害虫
(Ａ)ハエ亜目(Brachycera)
(ａ)ハモグリバエ科(Agromyzidae)の、例えば、リリオマイザ属種(Liriomyza spp.)の、ナスハモグリバエ(Liriomyza bryoniae)、ネギハモグリバエ(Liriomyza chinensis)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii)；その他の、ナモグリバエ(Chromatomyia horticola)、イネハモグリバエ(Agromyza oryzae)；
(ｂ)ハナバエ科(Anthomyiidae)の、例えば、デリア属種(Delia spp.)の、タネバエ(Delia platura)、キャベツハナバエ (Delia radicum)；その他の、テンサイモグリハナバエ(Pegomya cunicularia)；
(ｃ)ショウジョウバエ科(Drosophilidae)の、例えば、ショウジョウバエ属種(Drosophila spp.)の、キイロショウジョウバエ(Drosophila melanogaster)、オウトウショウジョウバエ(Drosophila suzukii)；
(ｄ)ミギワバエ科(Ephydridae)の、例えば、イネヒメハモグリバエ(Hydrellia griseola)；
(ｅ)ハネオレバエ科(Psilidae)の、例えば、ニンジンサビバエ (Psila rosae)； 
(ｆ)ミバエ科(Tephritidae)の、例えば、バクトロセラ属種(Bactrocera spp.)の、ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis)；例えば、ラゴレチス属種(Rhagoletis spp.)の、ヨーロッパオウトウミバエ (Rhagoletis cerasi)、リンゴミバエ (Rhagoletis pomonella)；その他の、チチュウカイミバエ(Ceratitis capitata)、オリーブミバエ(Dacus oleae)。 (5) Flies (Diptera) pests
(A) Brachycera
(a) From the family Agromyzidae, for example, from the genus Liriomyza spp., from Liriomyza bryoniae, from Liriomyza chinensis, from tomato leaf (Liriomyza sativae), from rio myza trifoli; Others, Chromatomyia horticola, Agromyza oryzae;
(b) From the family Anthomyiidae, for example, Delia spp., Dela platura, Cabbage fly (Delia radicum); Other, Pegomya cunicularia;
(c) Drosophila suzukii from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
(d) from the Ephydridae family, for example, Hydrellia griseola;
(e) from the Pleidae family, for example, Psila rosae;
(f) From the family Tephritidae, for example, Bactrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis; for example, Rhagoletis spp. Rhagoletis cerasi), Rhagoletis pomonella; Others, Ceratitis capitata, Olive fruit fly (Dacus oleae).
(Ｂ)カ亜目(Nematocera)
(ａ)タマバエ科(Cecidomyiidae)の、例えば、ダイズサヤタマバエ(Asphondylia yushimai)、ソルガムタマバエ(Contarinia sorghicola)、ヘシアンバエ(Mayetiola destructor)、ムギアカタマバエ(Sitodiplosis mosellana)。 (B) Nematocera
(a) From the family Cecidomyiidae, for example, the soybean fly (Asphondylia yushimai), the sorghum fly (Contarinia sorghicola), the fly fly (Mayetiola destructor), the mud fly (Sitodiplosis mosellana).
(６)バッタ目(Orthoptera)の害虫
(ａ)バッタ科(Acrididae)の、例えば、スキストセルカ属種(Schistocerca spp.)の、アメリカイナゴ (Schistocerca americana)、サバクトビバッタ (Schistocerca gregaria)；その他の、オーストラリアトビバッタ(Chortoicetes terminifera)、モロッコイナゴ (Dociostaurus maroccanus)、トノサマバッタ(Locusta migratoria)、ブラウンイナゴ(Locustana pardalina)、アカトビバッタ (Nomadacris septemfasciata)、コバネイナゴ(Oxya yezoensis)；
(ｂ)コオロギ科(Gryllidae)の、例えば、ヨーロッパイエコオロギ (Acheta domestica)、エンマコオロギ(Teleogryllus emma)；
(ｃ)ケラ科(Gryllotalpidae)の、例えば、ケラ(Gryllotalpa orientalis)；
(ｄ)キリギリス科(Tettigoniidae)の、例えば、クラズミウマ (Tachycines asynamorus)。 (6) Grasshopper (Orthoptera) pests
(a) From the Acrididae family, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; (Dociostaurus maroccanus), grasshopper (Locusta migratoria), brown locust (Locustana pardalina), red locust (Nomadacris septemfasciata), cobaneago (Oxya yezoensis);
(b) From the family of crickets (Gryllidae), for example, European cricket (Acheta domestica), Teleogryllus emma;
(c) from the family Gryllotalpidae, for example, Gryllotalpa orientalis;
(d) From the Tettigoniidae family, for example, Tachycines asynamorus.
(７)ダニ類(Acari)
(Ａ)無気門目(Astigmata)のコナダニ類(Acaridida)
(ａ)コナダニ科(Acaridae)のダニ、例えば、リゾギルホス属種(Rhizoglyphus spp.)の、ネダニ(Rhizoglyphus echinopus)、ロビンネダニ(Rhizoglyphus robini)；例えば、ケナガコナダニ属種(Tyrophagus spp.)の、オンシツケナガコナダニ(Tyrophagus neiswanderi)、オオケナガコナダニ(Tyrophagus perniciosus)、ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis)；その他、アシブトコナダニ(Acarus siro)、ムギコナダニ(Aleuroglyphus ovatus)、ニセケナガコナダニ(Mycetoglyphus fungivorus)； (7) Tick (Acari)
(A) Astigmata (Acaridida)
(a) Acaridae ticks, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; for example, Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus tick
(Ｂ)前気門目(Prostigmata)のケダニ類(Actinedida)
(ａ)ハダニ科(Tetranychidae)のダニ、例えば、ブリオビア属種(Bryobia spp.)の、クローバーハダニ(Bryobia praetiosa)、ニセクローバーハダニ(Bryobia rubrioculus)；例えば、エオテトラニクス属種(Eotetranychus spp.)の、コウノシロハダニ(Eotetranychus asiaticus)、アンズハダニ(Eotetranychus boreus)、エノキハダニ(Eotetranychus celtis)、ミチノクハダニ(Eotetranychus geniculatus)、ミヤケハダニ(Eotetranychus kankitus)、クリハダニ(Eotetranychus pruni)、シイノキハダニ(Eotetranychus shii)、スミスハダニ(Eotetranychus smithi)、スギナミハダニ(Eotetranychus suginamensis)、クルミハダニ(Eotetranychus uncatus)；例えば、オリゴニクス属種(Oligonychus spp.)の、スギノハダニ(Oligonychus hondoensis)、チビコブハダニ(Oligonychus ilicis)、カラマツハダニ(Oligonychus karamatus)、マンゴーハダニ(Oligonychus mangiferus)、サトウキビハダニ(Oligonychus orthius)、アボガドハダニ(Oligonychus perseae)、エゾスギハダニ(Oligonychus pustulosus)、イネハダニ(Oligonychus shinkajii)、トドマツハダニ(Oligonychus ununguis)；例えば、パノニクス属種(Panonychus spp.)の、ミカンハダニ(Panonychus citri)、クワオオハダニ(Panonychus mori)、リンゴハダニ(Panonychus ulmi)；例えば、テトラニクス属種(Tetranychus spp.)の、ニセナミハダニ(Tetranychus cinnabarinus)、カンザワハダニ(Tetranychus kanzawai)、アシノワハダニ(Tetranychus ludeni)、ミズナラハダニ(Tetranychus quercivorus)、サガミハダニ(Tetranychus phaselus)、ナミハダニ(Tetranychus urticae)、オウトウハダニ(Tetranychus viennensis)；例えば、アポニクス属(Aponychus spp.)の、イトマキハダニ(Aponychus corpuzae)、タイリクハダニ(Aponychus firmianae)；例えば、ミドリハダニ属(Sasanychus spp.)の、ミドリハダニ(Sasanychus akitanus)、ヒメミドリハダニ(Sasanychus pusillus)；例えば、シゾテトラニクス属(Shizotetranychus spp.)の、タケスゴモリハダニ(Shizotetranychus celarius)、ケナガスゴモリハダニ(Shizotetranychus longus)、ススキスゴモリハダニ(Shizotetranychus miscanthi)、ヒメササハダニ(Shizotetranychus recki)、ヤナギハダニ(Shizotetranychus schizopus)；その他、カタバミハダニ(Tetranychina harti)、ナミケナガハダニ(Tuckerella pavoniformis)、ケウスハダニ(Yezonychus sapporensis)； (B) Prostigmata mite (Actinedida)
(a) Tetranychidae ticks, for example, Bryobia spp., Clover spider mites (Bryobia praetiosa), Fowl spider mites (Bryobia rubrioculus); , White spider mite (Eotetranychus kankitus), tick mite (Eotetranychus kankitus) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp. Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychu s orthius), Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; tick, Pony Panonychus mori), apple spider mites (Panonychus ulmi); for example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus vorni, Tetranychus tranni (Tetranychus phaselus), nite spider mite (Tetranychus urticae), mite spider mite (Tetranychus viennensis); for example, Aponicchus spp. .), Sasanychus akitanus, Spider mites (Sasanychus pusillus); for example, Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanzo, chus Willow spider mites (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis, Kew spider mite (Yezonychus sapporensis);
(ｂ)ヒメハダニ科(Tenuipalpidae)のダニ、例えば、ブレビパルプス属種(Brevipalpus spp.)の、ブドウヒメハダニ(Brevipalpus lewisi)、チャノヒメハダニ(Brevipalpus obovatus)、ミナミヒメハダニ(Brevipalpus phoenicis)、サボテンヒメハダニ(Brevipalpus russulus)、オンシツヒメハダニ(Brevipalpus californicus)；例えば、テニパルプス属種(Tenuipalpus spp.)の、ランヒメハダニ(Tenuipalpus pacificus)、カキヒメハダニ(Tenuipalpus zhizhilashviliae)；その他、パイナップルヒメハダニ(Dolichotetranychus floridanus)；
(ｃ)フシダニ科(Eriophyidae)のダニ、例えば、アセリア属種(Aceria spp.)の、カキサビダニ(Aceria diospyri)、イチジクモンサビダニ(Aceria ficus)、クリフシダニ(Aceria japonica)、クコフシダニ(Aceria kuko)、カーネーションサビダニ(Aceria paradianthi)、クコハモグリダニ(Aceria tiyingi)、チューリップサビダニ(Aceria tulipae)、シバハマキフシダニ(Aceria zoysiea)；例えば、エリオフィエス属種(Eriophyes spp.)の、ニセナシサビダニ(Eriophyes chibaensis)、ウメフシダニ(Eriophyes emarginatae)；例えばアクロプス属種(Aculops spp.)の、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi)；例えば、アクルス属種(Aculus spp.)の、モモサビダニ(Aculus fockeui)、リンゴサビダニ(Aculus schlechtendali)；その他、チャノナガサビダニ(Acaphylla theavagrans)、チャノサビダニ(Calacarus carinatus)、ブドウハモグリダニ(Colomerus vitis)、ブドウサビダニ(Calepitrimerus vitis)、ナシサビダニ(Epitrimerus pyri)、キンモクサビダニ(Paraphytoptus kikus)、マキサビダニ(Paracalacarus podocarpi)、リュウキュウミカンサビダニ(Phyllocotruta citri)；
(ｄ)ホコリダニ科(Transonemidae)のダニ、例えば、タルソネムス属種(Tarsonemus spp.)の、スジブトホコリダニ(Tarsonemus bilobatus)、アシボソホコリダニ(Tarsonemus waitei)；その他、シクラメンホコリダニ(Phytonemus pallidus)、チャノホコリダニ(Polyphagotarsonemus latus)；
(ｅ)ハシリダニ科(Penthaleidae)のダニ、例えば、ペンタレウス属種(Penthaleus spp.)の、ハクサイダニ(Penthaleus erythrocephalus)、ムギダニ(Penthaleus major)。 (b) Tenuipalpidae ticks, for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus), for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other, Tenuipalpus zhizhilashviliae;
(c) Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp. e.g., Aculops spp., Aculops lycopersici, Aculops pelekassi; e.g., Aculus fockeui, Aculus fockeui, Aculus fockeui schlechtendali); others, Acaphylla theavagrans, Calacarus carinatus, grape hammog Mites (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 pallidus, Laphatus tick );
(e) Mites of the family Penthaleidae, for example, Penthaleus erythrocephalus, Penthaleus major of Penthaleus spp.
　本発明の有害生物防除剤または殺ダニ若しくは殺虫剤は、本発明のアミド化合物以外の成分を含有してもよい。他の成分としては、製剤化のために使用する公知の担体などが挙げられる。また、他の成分として、従来公知の、殺菌剤、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、植物調節剤、共力剤、肥料、土壌改良剤、動物用飼料などを挙げることができる。このような他の成分を含有することによって、相乗効果を奏することがある。 The pest control agent or acaricide or insecticide of the present invention may contain components other than the amide compound of the present invention. Examples of other components include known carriers used for formulation. In addition, as other components, conventionally known fungicides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, etc. be able to. By containing such other components, there may be a synergistic effect.
　本発明の有害生物防除剤と混用または併用することができる、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤などの具体例を以下に示す。 Specific examples of 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.
(１)アセチルコリンエステラーゼ阻害剤：
(ａ)カーバメート系：　アラニカルブ、アルジカルブ、ベンジオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、オキサミル、ピリミカルブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、XMC、キシリルカルブ、フェノチオカルブ、MIPC、MPMC、MTMC、アルドキシカルブ、アリキシカルブ、アミノカルブ、ブフェンカルブ、クロエトカルブ、メタム・ナトリウム、プロメカルブ； (1) Acetylcholinesterase inhibitor:
(a) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxyl Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
(ｂ)有機リン系：　アセフェート、アザメチホス、アジンホス-エチル、アジンホス-メチル、カズサホス、クロルエトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホス-メチル、クマホス、シアノホス、デメトン-S-メチル、ダイアジノン、ジクロルボス/DDVP、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、EPN、エチオン、エトプロホス、ファムフール、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソカルボホス、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシジメトン-メチル、パラチオン、パラチオン-メチル、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス-メチル、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリンホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン；ブロモホス・エチル、BRP、カルボフェノチオン、シアノフェンホス、CYAP、デメトン-Ｓ-メチルスルホン、ジアリホス、ジクロフェンチオン、ジオキサベンゾホス、エトリムホス、フェンスルホチオン、フルピラゾホス、ホノホス、ホルモチオン、ホスメチラン、イサゾホス、ヨードフェンホス、メタクリホス、ピリミホス－エチル、ホスホカルブ、プロパホス、プロトエート、スルプロホス。 (b) Organophosphorus: Acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, kazusafos, chlorethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, Dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethione, etoprophos, famfur, phenamiphos, fenitrothion, fenthion, phostiazet, heptenophos, imisiaphos, isofenphos, isocarbophos, isoxathione, malathione, methalmethione, mecarbamethione Monocrotophos, nared, ometoate, oxydimethone-methyl, parathion, parathion-methyl, phentoe Folate, hosalon, phosmet, phosphamidone, phoxime, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyracrofos, pyridafenthion, quinalphos, sulfotep, tebupyrine phos, temefos, terbufos, tetrachlorvinphos, thiomethone, triazophos, trichlorfos, bamidthione; Ethyl, BRP, carbophenothion, cyanophenphos, CYAP, demeton-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etrimphos, phensulfothion, flupyrazophos, phonofos, formomothion, phosmethylan, isazophos, iodofenphos, methacliphos , Pyrimifos-ethyl, phosphocarb, propaphos, protoate, sulprophos.
(２)GABA-作動性塩素イオンチャネルアンタゴニスト：　アセトプロール、クロルデン、エンドスルファン、エチプロール、フィプロニル、ピラフルプロール、ピリプロール；カンフェクロル、ヘプタクロル、ジエノクロル。
(３)ナトリウムチャンネルモジュレーター：　アクリナトリン、d-シス-トランス アレスリン、d-トランスアレスリン、ビフェントリン、ビオアレスリン、ビオアレスリンS-シクロペンチル異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ-シフルトリン、シハロトリン、ラムダ-シハロトリン、ガンマ-シハロトリン、シペルメトリン、アルファ-シペルメトリン、ベータ-シペルメトリン、シータ-シペルメトリン、ゼータ-シペルメトリン、シフェノトリン[(1R)-トランス異性体]、デルタメトリン、エンペントリン[(EZ)-(1R)-異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン[(1R)-トランス異性体]、プラレトリン、ピレスラム、レスメトリン、シラフルオフェン、テフルスリン、テトラメトリン[(1R)-異性体]、トラロメトリン、トランスフルトリン、アレスリン、ピレトリン、ピレトリンI、ピレトリンII、プロフルトリン、ジメフルトリン、ビオエタノメトリン、ビオペルメトリン、トランスペルメトリン、フェンフルトリン、フェンピリトリン、フルブロシトリネート、フルフェンプロックス、メトフルトリン、プロトリフェンブト、ピレスメトリン、テラレトリン。 (2) GABA-agonist chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulator: Acrinatrin, d-cis-trans allelesine, d-transareleslin, bifenthrin, bioareslin, bioareslin isomers, bioresmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R) -isomers], esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, tau-fulvalinate, halfenprox, imiprothrin, cade Phosphorus, permethrin, phenothrin [(1R) -trans isomer], praretrin, pyrethram, resmethrin, silafluophene, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II , Profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, fulbrocitrinate, flufenprox, methfluthrin, protrifen butto, pyrethmethrin, terraretrin.
(４)ニコチン性アセチルコリン受容体アゴニスト：　アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、ニチアジン、チアクロプリド、チアメトキサム、スルフォキサフロール、ニコチン、フルピラジフロン。
(５)ニコチン性アセチルコリン受容体アロステリックモジュレーター：　スピネトラム、スピノサド。
(７)幼若ホルモン様物質：　ヒドロプレン、キノプレン、メソプレン、フェノキシカルブ、ピリプロキシフェン；ジオフェノラン、エポフェノナン、トリプレン。
(８)その他非特異的阻害剤：　臭化メチル、クロルピクリン、フッ化スルフリル、ホウ砂、吐酒石。
(９)同翅目選択的摂食阻害剤：　フロニカミド、ピメトロジン、ピリフルキナゾン。 (4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine, flupiradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulator: spinetoram, spinosad.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epofenonane, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar.
(9) Homogeneous selective feeding inhibitors: flonicamid, pymetrozine, pyrifluquinazone.
(１０)ダニ類生育阻害剤：　クロフェンテジン、ジフロビダジン、ヘキシチアゾクス、エトキサゾール。
(１１)微生物由来昆虫中腸内膜破壊剤：　バチルス・チューリンゲンシス亜種イスラエレンシ、バチルス・スファエリクス、バチルス・チューリンゲンシス亜種アイザワイ、バチルス・チューリンゲンシス亜種クルスタキ、バチルス・チューリンゲンシス亜種テネブリオニス、Ｂｔ作物タンパク質：Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1。
(１２)ミトコンドリアATP生合成酵素阻害剤：　ジアフェンチウロン、アゾシクロチン、シヘキサチン、酸化フェンブタスズ、プロパルギット、テトラジホン。
(１３)酸化的リン酸化脱共役剤：　クロルフェナピル、スルフラミド、DNOC；ビナパクリル、ジノブトン、ジノカップ。
(１４)ニコチン性アセチルコリン受容体チャンネルブロッカー：　ベンスルタップ、カルタップ塩酸塩；ネライストキシン；チオスルタップ一ナトリウム塩、チオシクラム。
(１５)キチン合成阻害剤：　ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン、ブプロフェジン、フルアズロン。
(１６)双翅目脱皮かく乱剤：　シロマジン。
(１７)脱皮ホルモン受容体アゴニスト：　クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド。
(１８)オクトパミン受容体アゴニスト：　アミトラズ、デミジトラズ、クロルジメホルム。
(１９)ミトコンドリア電子伝達系複合体III阻害剤：　アセキノシル、フルアクリピリム、ヒドラメチルノン。
(２０)ミトコンドリア電子伝達系複合体I阻害剤：　フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、ロテノン。 (10) Tick growth inhibitor: clofentezin, difluvidazine, hexythiazox, etoxazole.
(11) Microbial-derived insect midgut lining destroyer: Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Kurstaki, 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, fenbutasine oxide, propargite, tetradiphone.
(13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup.
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam.
(15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
(16) Diptera molting agent: cyromazine.
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonist: Amitraz, demiditraz, chlordimeform.
(19) Mitochondrial electron transport system complex III inhibitor: acequinosyl, fluacrylpyrim, hydramethylnon.
(20) Mitochondrial electron transport system complex I inhibitor: phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.
(２１)電位依存性ナトリウムチャネルブロッカー：　インドキサカルブ、メタフルミゾン。
(２２)アセチルCoAカルボキシラーゼ阻害剤：　スピロジクロフェン、スピロメシフェン、スピロテトラマト。
(２３)ミトコンドリア電子伝達系複合体IV阻害剤：　リン化アルミニウム、リン化カルシウム、ホスフィン、リン化亜鉛、シアニド。
(２４)ミトコンドリア電子伝達系複合体II阻害剤：　シエノピラフェン、シフルメトフェン、ピフルブミド。
(２５)リアノジン受容体モジュレーター：　クロラントラニリプロール、シアントラニプロール、フルベンジアミド、シクラニリプロール、テトラニリプロール。
(２６)混合機能オキシダーゼ阻害剤化合物：　ピペロニルブトキシド。
(２７)ラトロフィリン受容体作用薬：　デプシペプチド、環状デプシペプチド、24員環状デプシペプチド、エモデプシド。
(２８)その他の剤(作用機構が未知)：　アザジラクチン、ベンゾキシメート、ビフェナゼート、ブロモプロピレート、キノメチオネート、クリオライト、ジコホル、ピリダリル、ベンクロチアズ、硫黄、アミドフルメット、1,3－ジクロロプロペン、DCIP、フェニソブロモレート、ベンゾメート、メタアルデヒド、クロルベンジレート、クロチアゾベン、ジシクラニル、フェノキサクリム、フェントリファニル、フルベンジミン、フルフェナジン、ゴシップルア、ジャポニルア、メトキサジアゾン、石油、オレイン酸カリウム、テトラスル、トリアラセン、アフィドピロペン(afidopyropen)、フロメトキン、フルフィプロル(flufiprole)、フルエンスルフォン、メペルフルスリン、テトラメチルフルスリン、トラロピリル、ジメフルスリン、メチルネオデカンアミド、フルララネル、アフォキソラネル、フルキサメタミド、５－[５－(３，５－ジクロロフェニル)－５－トリフルオロメチル－４，５－ジヒドロイソオキサゾール－３－イル]－２－(１Ｈ－１，２，４－トリアゾール－１－イル)ベンゾニトリル(CAS:943137-49-3)、ブロフラニリド、その他のメタジアミド類。 (21) Voltage-gated sodium channel blocker: indoxacarb, metaflumizone.
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat.
(23) Mitochondrial electron transport complex IV inhibitor: Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport system complex II inhibitor: Sienopyrafen, cyflumethofene, pivlumide.
(25) Ryanodine receptor modulator: chlorantraniliprole, cyantraniprole, fulvendiamide, cyclaniliprol, tetraniprolol.
(26) Mixed function oxidase inhibitor compound: Piperonyl butoxide.
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (unknown mechanism of action): azadirachtin, benzoxymate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicofol, pyridalyl, bencrothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, Phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasul, trialacene, aphidopyropene (afidopyropen ), Flometokin, flufiprole, fluenesulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodeca Amide, fluralanel, afoxolanel, floxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2,4 -Triazol-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, and other metadiamides.
(２９)駆虫剤：
(ａ)ベンズイミダゾール系：　フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール；フェバンテル、ネトビミン、チオファネート；チアベンダゾール、カンベンダゾール；
(ｂ)サリチルアニリド系：　クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド；
(ｃ)置換フェノール系：　ニトロキシニル、ニトロスカネート；
(ｄ)ピリミジン系：　ピランテル、モランテル；
(ｅ)イミダゾチアゾール系：　レバミソール、テトラミソール；
(ｆ)テトラヒドロピリミジン系：　プラジカンテル、エプシプランテル；
(ｇ)その他の駆虫薬：　シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ；ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル；チアセタルサミド、メロルサミン、アルセナマイド。 (29) 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 series: praziquantel, epsiprantel;
(g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetalamide, melolsamine, arsenamide.
　本発明の有害生物防除剤と混用または併用することができる、殺菌剤の具体例を以下に示す。
(１)核酸生合成阻害剤：
(ａ)RNAポリメラーゼＩ阻害剤：　ベナラキシル、ベナラキシル-M、フララキシル、メタラキシル、メタラキシル-M；オキサジキシル；クロジラコン、オフレース；
(ｂ)アデノシンデアミナーゼ阻害剤：　ブピリメート、ジメチリモール、エチリモール；
(ｃ)DNA/RNA合成阻害剤：　ハイメキサゾール、オクチリノン；
(ｄ)DNAトポイソメラーゼII阻害剤：　オキソリン酸。 Specific examples of the bactericides that can be used in combination or in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race;
(b) adenosine deaminase inhibitor: bupilimate, dimethylylmol, ethylimol;
(c) DNA / RNA synthesis inhibitors: Himexazole, octirinone;
(d) DNA topoisomerase II inhibitor: Oxophosphate.
(２)有糸核分裂阻害剤および細胞分裂阻害剤：
(ａ)β－チューブリン重合阻害剤：　ベノミル、カルベンダジム、クロルフェナゾール、フベリダゾール、チアベンダゾール；チオファネート、チオファネートメチル；ジエトフェンカルブ；ゾキサミド；エタボキサム；
(ｂ)細胞分裂阻害剤：　ペンシクロン；
(ｃ)スペクトリン様タンパク質の非局在化阻害剤：　フルオピコリド。 (2) Mitotic fission inhibitor and cell division inhibitor:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; dietofencarb; zoxamide; ethaboxam;
(b) Cell division inhibitor: Pencyclon;
(c) Delocalization inhibitor of spectrin-like protein: fluopicolide.
(３)呼吸阻害剤：
(ａ)複合体I NADH酸化還元酵素阻害剤：　ジフルメトリム；トルフェンピラド；
(ｂ)複合体IIコハク酸脱水素酵素阻害剤：　ベノダニル、フルトラニル、メプロニル；イソフェタミド；フルオピラム；フェンフラム、フルメシクロックス；カルボキシン、オキシカルボキシン；チフルザミド；ベンゾビンジフルピル、ビキサフェン、フルキサピロキサド、フラメトピル、イソピラザム、ペンフルフェン、ペンチオピラド、セダキサン；ボスカリド；
(ｃ)複合体IIIユビキノールオキシダーゼQo阻害剤：　アゾキシストロビン、クモキシストロビン、クメトキシストロビン、エノキサストロビン、フルフェノキシストロビン、ピコキシストロビン、ピラオキシストロビン；ピラクロストロビン、ピラメトストロビン、トリクロピリカルブ；クレソキシム-メチル、トリフロキシストロビン；ジモキシストロビン、フェナミンストロビン、メトミノストロビン、オリサストロビン；ファモキサドン；フルオキサストロビン；フェンアミドン；ピリベンカルブ；
(ｄ)複合体IIIユビキノール還元酵素Qi阻害剤：　シアゾファミド；アミスルブロム；
(ｅ)酸化的リン酸化の脱共役剤：　ビナパクリル、メプチルジノカップ、ジノカップ；フルアジナム；フェリムゾン；
(ｆ)酸化的リン酸化阻害剤(ATP 合成酵素の阻害剤)：　フェンチンアセテート、塩化フェンチン、水酸化フェンチン；
(ｇ)ATP生産阻害剤：　シルチオファム；
(ｈ)複合体III：シトクローム bc1(ユビキノン還元酵素)のQx(未知)阻害剤：　アメトクトラジン。 (3) Respiratory inhibitor:
(a) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad;
(b) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumeciclos; carboxin, oxycarboxin; tifluzamide; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
(c) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; pyraclostrobin, Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Metominostrobin, Orisastrobin; Famoxadone; Fluoxastrobin; Fenamidon;
(d) Complex III ubiquinol reductase Qi inhibitor: Ciazofamide; Amisulbrom;
(e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocup, dinocup; fluazinam; ferrimzone;
(f) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): Amethoctrazine.
(４)アミノ酸およびタンパク質合成阻害剤
(ａ)メチオニン生合成阻害剤：　アンドプリム、シプロジニル、メパニピリム、ピリメタニル；
(ｂ)タンパク質合成阻害剤：　ブラストサイジン-Ｓ；カスガマイシン、カスガマイシン塩酸塩；ストレプトマイシン；オキシテトラサイクリン。 (4) Amino acid and protein synthesis inhibitors
(a) Methionine biosynthesis inhibitor: Andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(b) Protein synthesis inhibitor: blasticidin-S; kasugamycin, kasugamycin hydrochloride; streptomycin; oxytetracycline.
(５)シグナル伝達阻害剤：
(ａ)シグナル伝達阻害剤：　キノキシフェン、プロキナジド；
(ｂ)浸透圧シグナル伝達におけるMAP・ヒスチジンキナーゼ阻害剤：　フェンピクロニル、フルジオキソニル；クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン。 (5) Signaling inhibitor:
(a) Signaling inhibitor: quinoxyphene, proquinazide;
(b) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.
(６)脂質および細胞膜合成阻害剤：
(ａ)りん脂質生合成、メチルトランスフェラーゼ阻害剤：　エジフェンホス、イプロベンホス、ピラゾホス；イソプロチオラン；
(ｂ)脂質の過酸化剤：　ビフェニル、クロロネブ、ジクロラン、キンドゼン、テクナゼン、トルクロホスメチル；エトリジアゾール；
(ｃ)細胞膜に作用する剤：　ヨードカルブ、プロパモカルブ、プロパモカルブ塩酸塩、プロパモカルブホセチレート、プロチオカルブ；
(ｄ)病原菌細胞膜を撹乱する微生物：　バチルスズブチリス菌、バチルス ズブチリスQST713 株、バチルス ズブチリスFZB24 株、バチルス ズブチリスMBI600 株、バチルス ズブチリスD747株；
(ｅ)細胞膜を撹乱する剤：　ゴセイカユプテ(ティーツリー)の抽出物。 (6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyltransferase inhibitor: 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) Microorganisms that disrupt the pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain;
(e) Agent that disturbs the cell membrane: An extract of Goseika Yupte (Tea Tree).
(７)細胞膜のステロール生合成阻害剤：
(ａ)ステロール生合成におけるC14位の脱メチル化阻害剤：　トリホリン；ピリフェノックス、ピリソキサゾール；フェナリモル、フルルプリミドール、ヌアリモル；イマザリル、イマザリル硫酸塩、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、ビニコナゾール；アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール-M、エポキシコナゾール、エタコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホール、フルコナゾール、フルコナゾール－シス、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、フルキンコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール；プロチオコナゾール、ボリコナゾール；
(ｂ)ステロール生合成におけるΔ14還元酵素およびΔ8→Δ7－イソメラーゼの阻害剤：
　アルジモルフ、ドデモルフ、ドデモルフ酢酸塩、フェンプロピモルフ、トリデモルフ；フェンプロピジン、ピペラリン；スピロキサミン；
(ｃ)ステロール生合成系のC4位脱メチル化における3-ケト還元酵素阻害剤：　フェンヘキサミド；フェンピラザミン；
(ｄ)ステロール生合成系のスクワレンエポキシダーゼ阻害剤：　ピリブチカルブ；ナフチフィン、テルビナフィン。 (7) Cell membrane sterol biosynthesis inhibitors:
(a) Demethylation inhibitor at the C14 position in sterol biosynthesis: Triphorine; Pyrifenox, Pyrioxazole; Phenarimol, Flurprimidol, Nuarimol; Imazalyl, Imazaryl Sulfate, Oxpoconazole, Pefrazoate, Prochloraz, Triflumizole 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 , Fluquinconazole, simeconazole, tebuconazole, tetraconazole triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine;
(c) 3-keto reductase inhibitor in C4-demethylation of sterol biosynthesis system: phenhexamide; fenpyrazamine;
(d) Sterol biosynthetic squalene epoxidase inhibitors: Pyributicarb; Naftifine, Terbinafine.
(８)細胞壁合成阻害
(ａ)トレハラーゼ阻害剤：　バリダマイシン；
(ｂ)キチン合成酵素阻害剤：　ポリオキシン、ポリオクソリム；
(ｃ)セルロース合成酵素阻害剤：　ジメトモルフ、フルモルフ、ピリモルフ；ベンチアバリカルブ、イプロバリカルブ、トルプロカルブ、バリフェナレート；マンジプロパミド。 (8) Cell wall synthesis inhibition
(a) trehalase inhibitor: validamycin;
(b) chitin synthase inhibitor: polyoxin, polyoxorim;
(c) Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph; Bench Avaricarb, Iprovaricarb, Toluprocarb, Variphenate; Mandipropamide.
(９)メラニン生合成阻害剤
(ａ)メラニン生合成の還元酵素阻害剤：　フサライド；ピロキロン；トリシクラゾール；
(ｂ)メラニン生合成の脱水酵素阻害剤：　カルプロパミド；ジクロシメット；フェノキサニル。 (9) Melanin biosynthesis inhibitor
(a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole;
(b) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl.
(１０)宿主植物の抵抗性誘導剤：
(ａ)サリチル酸合成経路に作用する剤：　アシベンゾラル-S-メチル；
(ｂ)その他：　プロベナゾール；チアジニル；イソチアニル；ラミナリン；オオイタドリ抽出液。 (10) Host plant resistance inducer:
(a) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl;
(b) Others: Probenazole; thiazinyl; isotianil; laminarin;
(１１)作用性が不明な剤：　シモキサニル、ホセチルアルミニウム、リン酸(リン酸塩)、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、メタスルホカルブ、シフルフェナミド、メトラフェノン、ピリオフェノン、ドジン、ドジン遊離塩基、フルチアニル。 (11) Agents with unknown activity: Simoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodin, dodin free base, fluthianyl.
(１２)多作用点を有する剤：　銅(銅塩)、ボルドー液、水酸化銅、銅ナフタレート、酸化銅、オキシ塩化銅、硫酸銅、硫黄、硫黄製品、多硫化カルシウム；ファーバム、マンコゼブ、マネブ、マンカッパー、メチラム、ポリカーバメート、プロピネブ、チラム、ジネブ、ジラム；キャプタン、カプタホール、フォルペット；クロロタロニル；ジクロフルアニド、トリルフルアニド；グアザチン、イミノクタジン酢酸塩(iminoctadine triacetate)、イミノクタジンアルベシル酸塩(iminoctadine trialbesilate)；アニラジン；ジチアノン；キノメチオネート；フルオルイミド。 (12) 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, Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; diclofluuride, tolylfluanid; guazatine, iminoctadine acetate, iminoctadine albecate (iminoctadine trialbesilate); anilazine; dithianon; quinomethionate;
(１３)その他の剤：　DBEDC、フルオロフォルペット、グアザチンアセテート、ビス(8-キノリノラト)銅(II)、プロパミジン、クロロピクリン、シプロフラム、アグロバクテリウム、ベトキサジン、ジフェニルアミン、メチルイソチアネート(MITC)、ミルデオマイシン、カプサイシン、クフラネブ、シプロスルファミド、ダゾメット、デバカルブ、ジクロロフェン、ジフェンゾクワット、ジフェンゾクワットメチルスルホネート、フルメトベル、ホセチルカルシウム、ホセチルナトリウム、イルママイシン、ナタマイシン、ニトロタールイソプロピル、オキサモカルブ、ピロールニトリン、テブフロキン、トルニファニド、ザリラミド、アルゴフェーズ(Algophase)、アミカルチアゾール(Amicarthiazol)、オキサチアピプロリン(Oxathiapiprolin)、メチラム亜鉛、ベンチアゾール、トリクラミド、ユニコナゾール、ミルデオマイシン、オキシフェンチイン(Oxyfenthiin)、ピカルブトラゾクス(picarbutrazox)。 (13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofram, agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC ), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat methylsulfonate, Flumetober, Focetyl calcium, Focetyl sodium, Irumamycin, Natamycin, Nitrotal isopropyl , Oxamocarb, pyrrolnitrin, tebufloquine, torniphanide, zaliramide, Algophase, amicaliazole (Amicarthiazol), oxathiapiproline, methylam zinc, Nthiazole, trichlamide, uniconazole, mildeomycin, oxyfenthiin, picarbutrazox.
　本発明の有害生物防除剤と混用または併用することができる、植物調節剤の具体例を以下に示す。
　アブシジン酸、カイネチン、ベンジルアミノプリン、１，３－ジフェニルウレア、ホルクロルフェヌロン、チジアズロン、クロルフェヌロン、ジヒドロゼアチン、ジベレリンＡ、ジベレリンＡ４、ジベレリンＡ７、ジベレリンＡ３、１－メチルシクロプロパン、Ｎ－アセチルアミノエトキシビニルグリシン(別名：アビグリシン)、アミノオキシ酢酸、硝酸銀、塩化コバルト、ＩＡＡ、４－ＣＰＡ、クロプロップ、２，４－Ｄ、ＭＣＰＢ、インドール－３－酪酸、ジクロルプロップ、フェノチオール、１－ナフチルアセトアミド、エチクロゼート、クロキシホナック、マレイン酸ヒドラジド、２，３，５－トリヨード安息香酸、サリチル酸、サリチル酸メチル、(-)－ジャスモン酸、ジャスモン酸メチル、(+)－ストリゴール、(+)－デオキシストリゴール、(+)－オロバンコール、(+)－ソルゴラクトン、４－オキソ－４－(２－フェニルエチル)アミノ酪酸；エテホン、クロルメコート、メピコートクロリド、ベンジルアデニン、５－アミノレブリン酸。 Specific examples of plant regulators that can be used in combination or in combination with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1 -Naphtylacetamide, Ethiclozate, Cloxiphonac, Maleic acid hydrazide, 2,3,5-Triiodobenzoic acid, Salicylic acid, Methyl salicylate, (-)-Jasmonic acid, Methyl jasmonate, (+)-Strigol, (+) -Deoxystri Lumpur, (+) - Orobankoru, (+) - Sorugorakuton, 4-oxo-4- (2-phenylethyl) amino acid; ethephon, chlormequat, mepiquat chloride, benzyl adenine, 5-aminolevulinic acid.
〔内部寄生虫防除または駆除剤〕
　本発明の内部寄生虫防除剤または駆除剤は、本発明のアミド化合物から選ばれる少なくともひとつを有効成分として含有するものである。 [Internal parasite control or control agent]
The endoparasite control agent or pesticide of the present invention contains at least one selected from the amide compounds of the present invention as an active ingredient.
　本発明の内部寄生虫防除剤または駆除剤を使用する場合は、宿主動物１ｋｇに対して、本発明化合物が、０．０１～１０００ｍｇの割合となる量（医薬有効量）で使用することができる。
　本発明の内部寄生虫防除剤または駆除剤は、剤形によって特に制限されない。剤形としては、粉剤、粒剤、錠剤、カプセル剤、ポアオン製剤、スポットオン製剤、乳剤、スプレー剤、坐薬、注射剤（筋肉内、皮下、静脈内、腹腔内投与用注射剤など）、ウエハース、ビスケット、ミンチ肉等の形体であることができる。 When using the endoparasite control agent or the pesticide of the present invention, the compound of the present invention can be used in an amount (pharmacologically effective amount) of 0.01 to 1000 mg per 1 kg of the host animal. .
The endoparasite control agent or pesticide of the present invention is not particularly limited by the dosage form. Dosage forms include powders, granules, tablets, capsules, pour-on formulations, spot-on formulations, emulsions, sprays, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal injections, etc.), wafers , Biscuits, minced meat and the like.
　本発明の内部寄生虫防除または駆除剤は、本発明のアミド化合物のみを含有するものであってもよいし、液体担体、ガス状担体、固体担体などの担体、必要に応じて界面活性剤、その他の補助剤を更に含有していてもよい。
　また、本発明の内部寄生虫防除または駆除剤は、本発明のアミド化合物を多孔セラミック板や不織布などの基材に含浸させたものであってもよい。 The endoparasite control or control agent of the present invention may contain only the amide compound of the present invention, a carrier such as a liquid carrier, a gaseous carrier, a solid carrier, a surfactant as necessary, Other adjuvants may be further contained.
Further, the endoparasite control or control agent of the present invention may be obtained by impregnating a base material such as a porous ceramic plate or a nonwoven fabric with the amide compound of the present invention.
本発明の内部寄生虫防除または駆除剤の対象となる寄生虫は、宿主動物、特には温血動物や魚類の中に寄生する(内部寄生虫)。本発明の寄生虫防除または駆除剤が有効な宿主動物としては、ヒト、家畜哺乳動物(例えば、ウシ、ウマ、ブタ、ヒツジ、ヤギなど)、実験動物(例えば、マウス、ラット、スナネズミなど)、愛玩動物(例えば、ハムスター、モルモット、イヌ、ネコ、ウマ、リス、ウサギ、フェレットなど)、野生および動物園の哺乳動物(サル、キツネ、シカ、バッファローなど)、家禽(シチメンチョウ、アヒル、ニワトリ、ウズラ、ガチョウなど)、愛玩鳥(ハト、オウム、九官鳥、文鳥、インコ、ジュウシマツ、カナリアなど)などの温血動物；または、サケ、マス、ニシキゴイなどの魚類が挙げられる。寄生虫を防除および駆除することで、寄生虫が媒介する寄生虫疾患を予防または治療することができる。 Parasites that are targets of the endoparasite control or pesticide of the present invention parasitize in host animals, particularly warm-blooded animals and fish (endoparasites). Examples of a host animal in which the parasite control or control agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats), laboratory animals (e.g., mice, rats, gerbils, etc.) Pets (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalos, etc.), poultry (turkeys, ducks, chickens, quails, Warm-blooded animals such as geese and pet birds (eggs, parrots, nine-birds, wild birds, parakeets, juvenile pine, canaries, etc.); and fishes such as salmon, trout, and swordfish. By controlling and controlling the parasite, it is possible to prevent or treat a parasitic disease mediated by the parasite.
　防除または駆除対象の寄生虫としては、以下のものが挙げられる。
(１)腎虫目(Dioctophymatida)の線虫類
(ａ)腎虫科(Dioctophymatidae)の腎虫、例えば、ディオクトフィーマ属種(Dioctophyma spp.)の、腎虫(Dioctophyma renale)；
(ｂ)ソブリフィメ科(Soboliphymatidae)の腎虫、例えば、ソブリフィメ属種(Soboliphyme spp.)の、ソブリフィメ・アベイ(Soboliphyme abei)、ソブリフィメ・ブツリニ(Soboliphyme baturini)。 Parasites to be controlled or controlled include the following:
(1) Nematodes of Dioctophymatida
(a) nematodes of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp .;
(b) Nematodes of the family Soboliphymatidae, for example, Soboliphyme abei, Soboliphyme baturini, of the species Soboliphyme spp.
(２)毛頭虫目(Trichocephalida)の線虫類
(ａ)旋毛虫科(Trichinellidae)の旋毛虫、例えば、旋毛虫属種(Trichinella spp.)の、旋毛虫(Trichinella spiralis)；
(ｂ)鞭虫科(Trichuridae)の鞭虫、例えば、キャピラリア属種(Capillaria spp.)の、有環毛細線虫(Capillaria annulata)、捻転毛細線虫(Capillaria contorta)、肝毛細線虫(Capillaria hepatica)、穿通毛細線虫(Capillaria perforans)、キャピラリア・プリカ(Capillaria plica)、豚毛細線虫(Capillaria suis)；トリキュリス属種(Trichuris spp.)の、犬鞭虫(Trichuris vulpis)、牛鞭虫(Trichuris discolor)、羊鞭虫(Trichuris ovis)、トリキュリス・スクリジャビニー(Trichuris skrjabini)、豚鞭虫(Trichuris suis)。 (2) Trichocephalida nematodes
(a) Trichinellidae Trichinella, for example, Trichinella spiralis from Trichinella spp .;
(b) Trichuridae Trichuridae, for example, Capillaria spp. Capillaria annulata, Capillaria contorta, Capillary contorta Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
(３)桿線虫目(Rhabditida)の線虫類
　糞線虫科(Strongyloididae)の糞線虫、例えば、糞線虫属種(Strongyloides spp.)の、乳頭糞線虫(Strongyloides papillosus)、猫糞線虫(Strongyloides planiceps)、豚糞線虫(Strongyloides ransomi)、豚糞線虫(Strongyloides suis)、糞線虫(Strongyloides stercoralis)、アメリカ猫糞線虫(Strongyloides tumefaciens)、ネズミ糞線虫(Strongyloides ratti)。 (3) Rhabditida nematodes (Strongyloides spp.), For example, Strongyloides papillosus, cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
(４)円虫目(Strongylida)の線虫類
　鈎虫科(Ancylostomatidae)の鉤虫、例えば、鉤虫属種(Ancylostoma spp.)の、ブラジル鉤虫(Ancylostoma braziliense)、犬鉤虫(Ancylostoma caninum)、ズビニ鉤虫(Ancylostoma duodenale)、ネコ鈎虫(Ancylostoma tubaeforme)；ウンシナリア属種(Uncinaria spp.)の、狭頭鉤虫(Uncinaria stenocephala)；ブノストマム属種(Bunostomum spp.)の、牛鉤虫(Bunostomum phlebotomum)、羊鉤虫(Bunostomum trigonocephalum)。 (4) Strongylida nematodes: Ancylostomatidae worms, for example, Ancylostoma spp., Ancylostoma braziliense, Ancylostoma caninum, Zubini worms (Ancylostoma duodenale), cat helminth (Ancylostoma tubaeforme); Uncinaria spp., Uncinaria stenocephala; Bunostomum spp. (Bunostomum trigonocephalum).
(５)円虫目(Strongylida)の線虫類
(ａ)住血線虫科(Angiostrongylidae)の線虫、例えば、ネコ肺虫属種(Aelurostrongylus spp.)の、猫肺虫(Aelurostrongylus abstrusus)；住血線虫属種(Angiostrongylus spp.)の、住血線虫(Angiostrongylus vasorum)、広東住血線虫(Angiostrongylus cantonesis)；
(ｂ)クレノゾーマ科(Crenosomatidae)の線虫、例えば、クレノゾーマ属種(Crenosoma spp.)の、肺毛細線虫(Crenosoma aerophila)、キツネ肺虫(Crenosoma vulpis)；
(ｃ)フィラロイデス科(Filaroididae)の線虫、例えば、フィラロイデス属種(Filaroides spp.)の、犬肺虫(Filaroides hirthi)、フィラロイデス・オスレリ(Filaroides osleri)；
(ｄ)肺虫科(Metastrongylidae)の肺虫、例えば、豚肺虫属種(Metastrongylus spp.)の、豚肺虫(Metastrongylus apri)、メタストロンギルス・アシムメトリクス(Metastrongylus asymmetricus)、メタストロンギルス・プデンドテクタス(Metastrongylus pudendotectus)、メタストロンギルス・サルミィ(Metastrongylus salmi)；
(ｅ)開嘴虫科(Syngamidae)の開嘴虫、例えば、シアトストーマ属種(Cyathostoma spp.)の、水鳥肺虫(Cyathostoma bronchialis)；シンガムス属種(Syngamus spp.)の、スクリジャビン開嘴虫(Syngamus skrjabinomorpha)、鶏開嘴虫(Syngamus trachea)。 (5) Strongylida nematodes
(a) nematodes of the family Angiostrongylidae, for example, Aelurostrongylus spp., cat lungworm (Aelurostrongylus abstrusus); Schistosomiasis (Angiostrongylus vasorum), Cantonese schistosomiasis (Angiostrongylus cantonesis);
(b) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp .;
(c) Filaroididae nematodes, for example, Filaroides hirthi, Filaroides osleri of Filaroides spp .;
(d) Pneumoides of the family Pneumolidae (Metastrongylidae), for example, Metastrongylus aprius, Metastrongylus asymmetricus, Metastrongylus asymmetricus, Metastrongylus asymmetricus Metastrongylus pudendotectus), Metastrongylus salmi;
(e) C. elegans of the Syngamidae family, for example, Cyathostoma bronchialis of the genus Cyathostoma spp .; Scrijabin larvae of the genus Syngamus spp. Syngamus skrjabinomorpha), chicken worm (Syngamus trachea).
(６)円虫目(Strongylida)の線虫類
(ａ)モリネウス科(Molineidae)の線虫、例えば、ネマトジルス属種(Nematodirus spp.)の、細頸毛円虫(Nematodirus filicollis)、ネマトジルス・スパティガー(Nematodirus spathiger)；
(ｂ)ディクチオカウルス科(Dictyocaulidae)の線虫、例えば、ディクチオカウルス属種(Dictyocaulus spp.)の、糸状肺虫(Dictyocaulus filaria)、牛肺虫(Dictyocaulus viviparus )；
(ｃ)捻転胃虫科(Haemonchidae)の線虫、例えば、ヘモンクス属種(Haemonchus spp.)の、捻転胃虫(Haemonchus contortus)；メキストシリウス属種(Mecistocirrus spp.)の、牛捻転胃虫(Mecistocirrus digitatus)；
(ｄ)捻転胃虫科(Haemonchidae)の線虫、例えば、胃虫属種(Ostertagia spp.)の、オステルターグ胃虫(Ostertagia ostertagi)；
(ｅ)ヘリグモネラ科(Heligmonellidae)の線虫、例えば、ニッポストロンジルス属種(Nippostrongylus spp.)の、ネズミ円虫(Nippostrongylus braziliensis)；
(ｆ)毛様線虫科(Trichostrongylidae)の線虫、例えば、毛様線虫属種(Trichostrongylus spp.)の、皺胃毛様線虫(Trichostrongylus axei)、蛇状毛様線虫(Trichostrongylus colubriformis)、毛様線虫科(Trichostrongylus tenuis)；ヒオストロンギルス属種(Hyostrongylus spp.)の、紅色毛様線虫(Hyostrongylus rubidus)；オベリスコイデス属種(Obeliscoides spp.)の、オベリスコイデス・クニクリ(Obeliscoides cuniculi)。 (6) Strongylida nematodes
(a) Nematodirus filicollis, Nematodirus spathiger from the nematodes of the Molineidae family, for example, Nematodirus spp .;
(b) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Bovine lungworm (Dictyocaulus viviparus);
(c) Haemonchidae nematodes, for example, Haemonchus spp., Haemonchus contortus; Mexistocirrus spp. (Mecistocirrus digitatus);
(d) Haemonchidae nematodes, for example, Ostertagia ostertagi from the genus Ostertagia spp .;
(e) Nematodes of the family Heligmonellidae, for example Nippostrongylus braziliensis, of the genus Nippostrongylus spp .;
(f) Trichostrongylidae nematodes, for example, Trichostrongylus axei, Trichostrongylus axei, Trichostrongylus colubriformis of Trichostrongylus spp. ), Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi ).
(７)円虫目(Strongylida)の線虫類
(ａ)シャベルティア科(Chabertiidae)の線虫、例えば、シャベルティア属種(Chabertia spp.)の、羊縮小線虫(Chabertia ovina)；腸結節虫属種(Oesophagostomum spp.)の、腸結節虫(豚)(Oesophagostomum brevicaudatum)、コロンビア腸結節虫(Oesophagostomum columbianum)、豚腸結節虫(Oesophagostomum dentatum)、腸結節虫(豚)(Oesophagostomum georgianum)、腸結節虫(Oesophagostomum maplestonei)、腸結節虫(豚)(Oesophagostomum quadrispinulatum)、牛腸結節虫(Oesophagostomum radiatum)、山羊腸結節虫(Oesophagostomum venulosum)、腸結節虫(イノシシ)(Oesophagostomum watanabei)；
(ｂ)豚腎虫科(Stephanuridae)の線虫、例えば、ステファヌラス属種(Stephanurus spp.)の、豚腎虫(Stephanurus dentatus)；
(ｃ)円虫科(Strongylidae)の線虫、例えば、円虫属種(Strongylus spp.)の、ロバ円虫(Strongylus asini)、無歯円虫(Strongylus edentatus)、馬円虫(Strongylus equinus)、普通円虫(Strongylus vulgaris)。 (7) Strongylida nematodes
(a) Nematodes of the Chabertiidae family, for example, the intestinal nodules of the Chabertia ovina; the intestinal nodules (Oesophagostomum spp.) of the genus Chabertia spp. (Pigs) (Oesophagostomum brevicaudatum), Colombian intestinal nodules (Oesophagostomum columbianum), swine intestinal nodules (Oesophagostomum dentatum), intestinal nodules (pigs) (Oesophagostomum georgianum), intestinal nodules (Oesophagostomum maplestonei), intestinal nodules (Oesophagostomum maplestonei) ) (Oesophagostomum quadrispinulatum), Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum watanabei;
(b) Stephanuridae nematodes, for example, Stephanurus dentatus, from Stephanurus spp .;
(c) C. elegans (Strongylidae), for example, from the species of the genus Strongylus spp., Strongylus asini, edentulous (Strongylus edentatus), Strongylus equinus , Strongylus vulgaris.
(８)蟯虫目(Oxyurida)の線虫類
　蟯虫科(Oxyuridae)の線虫、例えば、エンテロビウス属種(Enterobius spp.)の、チンパンジー蟯虫(Enterobius anthropopitheci)、蟯虫(Enterobius vermicularis)；オキシルス属(Oxyuris spp.)の、馬蟯虫(Oxyuris equi)；パサルルス属種(Passalurus spp.)の、ウサギ蟯虫(Passalurus ambiguus)。 (8) Oxyurida nematodes, Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris of Enterobius spp. spp.), Oxyuris equi; Passalurus spp., Passalurus ambiguus.
(９)回虫目(Ascaridida)の線虫類
(ａ)ニワトリ回虫科(Ascaridiidae)の線虫、例えば、ニワトリ回虫属種(Ascaridia spp.)の、ニワトリ回虫(Ascaridia galli)；
(ｂ)盲腸虫科(Heterakidae)の線虫、例えば、ヘテラキス属種(Heterakis spp.)の、ヘテラキス・ベラムポリア(Heterakis beramporia)、ヘテラキス・ブレビスピクルム(Heterakis brevispiculum)、鶏盲腸虫(Heterakis gallinarum)、ヘテラキス・プシーラ(Heterakis pusilla)、ヘテラキス・プトオーストラリス(Heterakis putaustralis)；
(ｃ)アニサキス科(Anisakidae)の線虫、例えば、アニサキス属種(Anisakis spp.)の、アニサキス線虫(Anisakis simplex)；
(ｄ)回虫科(Ascarididae)の線虫、例えば、回虫属種(Ascaris spp.)の、ヒト回虫(Ascaris lumbricoides)、豚回虫(Ascaris suum)；パラスカリア属種(Parascaris spp.)の、馬回虫(Parascaris equorum)；
(ｅ)トキソカーラ科(Toxocaridae)の線虫、例えば、トキソカーラ属種(Toxocara spp.)の、犬回虫(Toxocara canis)、犬小回虫(Toxocara leonina)、豚回虫(Toxocarasuum)、牛回虫(Toxocara vitulorum)、猫回虫(Toxocara cati)。 (9) Nematode of Ascaridida
(a) Acaridiidae nematodes, for example, Ascaridia galli from the genus Ascaridia spp .;
(b) Heterakidae nematodes such as Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis spp. Heterakis pusilla, Heterakis putaustralis;
(c) Anisakidae nematodes, for example, Anisakis simplex from Anisakis spp .;
(d) Nematodes of Ascarididae, for example, Ascaris lumbricoides, Ascaris suum; Ascaris suum; Parascaris spp. (Parascaris equorum);
(e) Toxocaridae nematodes, for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasum, Toxocara vitulorum ), Toxocara cati.
(１０)旋尾線虫目(Spirurida)の線虫類
(ａ)オンコセルカ科(Onchocercidae)の線虫、例えば、ブルギア属種(Brugia spp.)の、マレー糸状虫(Brugia malayi)、ブルギア・パハンギィ(Brugia pahangi)、ブルギア・パティ(Brugia patei)；ディペタロネーマ属種(Dipetalonema spp.)の、ディペタロネーマ・リコンディトゥム(Dipetalonema reconditum)；イヌ糸状虫属種(Dirofilaria spp.)の、イヌ糸状虫(Dirofilaria immitis)；フィラリア属種(Filaria spp.)の、フィラリア・オクリィ(Filaria oculi)；オンコセルカ属種(Onchocerca spp.)の、頸部糸状虫(Onchocerca cervicalis)、ギブソン糸状虫(Onchocerca gibsoni)、咽頭糸状虫(Onchocerca gutturosa)；
(ｂ)セタリア科(Setariidae)の線虫、例えば、セタリア属種(Setaria spp.)の、指状糸状虫(Setaria digitata)、馬糸条虫(Setaria equina)、唇乳頭糸状虫(Setaria labiatopapillosa)、マーシャル糸状虫(Setaria marshalli)；ブケレリア属種(Wuchereria spp.)の、バンクロフト糸状虫(Wuchereria bancrofti)；
(ｃ)糸状虫科(Filariidae)の線虫、例えば、パラフィラリア属種(Parafilaria spp.)の、多乳頭糸状虫(Parafilaria multipapillosa)；ステファノフィラリア属種(Stephanofilaria spp.)の、ステファノフィラリア・アッサムエンシス(Stephanofilaria assamensis)、ステファノフィラリア・デドエシー(Stephanofilaria dedoesi)、ステファノフィラリア・カエリー(Stephanofilaria kaeli)、沖縄糸状虫(Stephanofilaria okinawaensis)、ステファノフィラリア・スティレシー(Stephanofilaria stilesi)。 (10) Spirurida nematodes
(a) Nematodes of Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria spp. Filaria oculi; Onchocerca spp., Onchocerca cervicalis, Onchocerca gibsoni, Onchocerca gutturosa;
(b) Nematodes of the Setariidae family, for example, Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa , Setaria marshalli; Wuchereria spp., Wuchereria bancrofti;
(c) Filariidae nematodes, for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
(１１)旋尾線虫目(Spirurida)の線虫類
(ａ)顎口虫科(Gnathostomatidae)の線虫、例えば、顎口虫属種(Gnathostoma spp.)の、顎口虫(Gnathostoma doloresi)、有棘顎口虫(Gnathostoma spinigerum)；
(ｂ)ハブロネーマ科(Habronematidae)の線虫、例えば、ハブロネーマ属種(Habronema spp.)の、小口胃虫(Habronema majus)、小口胃虫(Habronema microstoma)、蠅馬胃虫(Habronema muscae)；ドラスキア属種(Draschia spp.)の、大口馬胃虫(Draschia megastoma)；
(ｃ)フィザロプテラ科(Physalopteridae)の線虫、例えば、フィサロプテラ属種(Physaloptera spp.)の、犬胃虫(Physaloptera canis)、キツネ胃虫(Physaloptera cesticillata)、フィサロプテラ・エルドシオーナ(Physaloptera erdocyona)、フィサロプテラ・フェリディス(Physaloptera felidis)、エジプト猫胃虫(Physaloptera gemina)、フィサロプテラ・パピロラディラータ(Physaloptera papilloradiata)、猫胃虫(Physaloptera praeputialis)、フィサロプテラ・シュードプラエルティアリス(Physaloptera pseudopraerutialis)、ラーラ胃虫(Physaloptera rara)、フィサロプテラ・シビリカ(Physaloptera sibirica)、フィサロプテラ・ブルピニウス(Physaloptera vulpineus)；
(ｄ)ゴンギロネマ科(Gongylonematidae)の線虫、例えば、ゴンギロネーマ属種(Gongylonema spp.)の、美麗食道虫(Gongylonema pulchrum)；
(ｅ)スピロセルカ科(Spirocercidae)の線虫、例えば、アスカロプス属種(Ascarops spp.)の、類円豚胃虫(Ascarops strongylina)；
(ｆ)テラジア科(Thelaziidae)の線虫、例えば、テラジア属種(Thelazia spp.)の、東洋眼虫(Thelazia callipaeda)、テラジア・グローサ(Thelazia gulosa)、涙眼虫(Thelazia lacrymalis)、ロデシア眼虫(Thelazia rhodesi)、スクリャービン眼虫(Thelazia skrjabini)。 (11) Spirurida nematodes
(a) Nematodes of the Gnathostomatidae family, for example, Gnathostoma doloresi, Gnathostoma spinigerum of Gnathostoma spp .;
(b) Nematodes of the family Habronematidae (Habronema spp.), for example, Habronema majus, Habronema microstoma, Habronema muscae; From the genus Species (Draschia spp.);
(c) Nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaoptera pseudopraerutialis rara), Physaloptera sibirica, Physaloptera vulpineus;
(d) Nematodes of the Gongylonematidae family, for example, Gongylonema pulchrum of the genus Gongylonema spp .;
(e) Nematodes of the Spirocercidae family, for example, Ascarops strongylina of Ascarops spp.
(f) Thelaziidae nematodes such as Thelazia spip., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini).
〔その他の有害生物についての防除剤〕
　その他にも、毒針や毒液を持ち、人獣に被害を加える害虫、各種の病原体・病原菌を媒介する害虫、人に不快感を与える害虫(有毒害虫・衛生害虫・不快害虫など)の防除効果に優れている。
　以下に、その具体例を示す。
(１)ハチ目(Hymenoptera)の害虫
ミフシババチ科(Argidae)のハチ、タマバチ科(Cynipidae)のハチ、マツハバチ科(Diprionidae)のハチ、アリ科(Formicidae)のアリ、アリバチ科(Mutillidae )のハチ、スズメバチ科(Vespidae)のハチ。
(２)ハエ目(Diptera)の害虫
カ科(Culicidae)のカ、イエバエ科(Muscidae)のハエ、ツェツェバエ科(Glossinidae)のツェツェバエ、ニクバエ科のニクバエ、シラミバエ科(Hippoboscidae)のハエ、クロバエ科(Calliphoridae)のハエ、ヒツジバエ科(Oestridae)のハエ。 [Control agents for other pests]
In addition, pests that have poisonous needles and venom and cause damage to humans, pests that mediate various pathogens and pathogens, pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests, etc.) Is excellent.
The specific example is shown below.
(1) Hymenoptera pests of the genus Bee (Argidae), bee of Cynipidae, bee of Diprionidae, bee of Formicidae, bee of Mutillidae, Vespidae's bee.
(2) Diptera mosquitoes from Culicidae, Muscidae flies, Tsetse flies from Glossinidae, Drosophila flies, Hippoboscidae flies, Flies Calliphoridae flies, Oestridae flies.
(３)その他の害虫
ゴキブリ類(Blattodea)、シロアリ類(termite)、クモ類(Araneae)、ムカデ類(cetipede)、ヤスデ類(millipede)、甲殻類(crustacea)、南京虫(Cimex lectularius)。 (3) Other pest cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes, crustacea, and paddy worms (Cimex lectularius).
　次に、実施例を示し、本発明をより具体的に説明する。ただし、本発明は以下の実施例によって何ら制限されるものではない。 Next, the present invention will be described more specifically by showing examples. However, the present invention is not limited by the following examples.
〔実施例１〕
2-(3-Ethyl-3-{[2-(trifluoromethyl)pyridin-4-yl]oxy}ureido)-N-isobutyl-2-methylpropanamide(化合物番号1-5)の合成 [Example 1]
Synthesis of 2- (3-Ethyl-3-{[2- (trifluoromethyl) pyridin-4-yl] oxy} ureido) -N-isobutyl-2-methylpropanamide (Compound No. 1-5)
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
(工程１－１)
tert-Butyl N-{[2-(trifluoromethyl)pyridin-4-yl]oxy}carbamate：化合物17
　4-chloro-2-(trifluoromethyl)pyridine(4.19ｇ)とBoc-ヒドロキシルアミン(3.24ｇ)をDMSO(40ml)に溶解し、水酸化カリウム(3.20ｇ)を加え、室温で5時間攪拌した。反応終了後、塩化アンモニウム水を加えて酢酸エチルにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物17(5.76ｇ、収率90％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.59( d , 1H ) , 7.69( br , 1H ) , 7.43( d , 1H ) , 7.22( dd , 1H ) , 1.52( s , 9H ) (Step 1-1)
tert-Butyl N-{[2- (trifluoromethyl) pyridin-4-yl] oxy} carbamate: Compound 17
4-chloro-2- (trifluoromethyl) pyridine (4.19 g) and Boc-hydroxylamine (3.24 g) were dissolved in DMSO (40 ml), potassium hydroxide (3.20 g) was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, aqueous ammonium chloride was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 17 (5.76 g, yield 90%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.59 (d, 1H), 7.69 (br, 1H), 7.43 (d, 1H), 7.22 (dd, 1H), 1.52 (s, 9H)
(工程１－２)
Phenyl N-{[2-(trifluoromethyl)pyridin-4-yl]oxy}carbamate：化合物18
　化合物17(5.76ｇ)をジクロロメタン70mlに溶解し、氷冷下トリエチルアミン(3.15ｇ)を加え、クロロギ酸フェニル(3.57ｇ)を滴下し、氷冷下1時間攪拌した。反応終了後、塩化アンモニウム水を加えジクロロメタン層を分離し、これに硫酸マグネシウムを加え乾燥、ろ過後、溶媒を減圧留去した。
　得られた残渣にジクロロメタン30mlを加え、トリフルオロ酢酸14mlを滴下し、室温にて4時間撹拌した。反応液を酢酸エチルにて希釈し、飽和炭酸水素ナトリウム水溶液にて中和後、有機層を分離した。得られた有機層に硫酸マグネシウムを加え乾燥、ろ過後、溶媒を減圧留去した。析出した結晶をヘキサンで洗浄し化合物18(6.04ｇ、2工程収率98％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.64( d , 1H ) , 8.39( s , 1H ) , 7.52( d , 1H ) , 7.43～7.38( m , 2H ) , 7.32～7.27( m , 2H ) , 7.20～7.17( m , 2H ) (Step 1-2)
Phenyl N-{[2- (trifluoromethyl) pyridin-4-yl] oxy} carbamate: Compound 18
Compound 17 (5.76 g) was dissolved in 70 ml of dichloromethane, triethylamine (3.15 g) was added under ice cooling, phenyl chloroformate (3.57 g) was added dropwise, and the mixture was stirred for 1 hour under ice cooling. After completion of the reaction, aqueous ammonium chloride was added to separate the dichloromethane layer. Magnesium sulfate was added thereto for drying and filtration, and then the solvent was distilled off under reduced pressure.
Dichloromethane (30 ml) was added to the resulting residue, trifluoroacetic acid (14 ml) was added dropwise, and the mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate, neutralized with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was separated. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The precipitated crystals were washed with hexane to obtain Compound 18 (6.04 g, 2-step yield 98%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.64 (d, 1H), 8.39 (s, 1H), 7.52 (d, 1H), 7.43 to 7.38 (m, 2H), 7.32 to 7.27 (m , 2H), 7.20-7.17 (m, 2H)
(工程１－３)
Ethyl 2-methyl-2-(3-{[2-(trifluoromethyl)pyridin-4-yl]oxy}ureido)propanoate：化合物19
　化合物18(6.04ｇ)のTHF(40ml)溶液に2-アミノ-2-メチルプロピオン酸エチル(2.93ｇ)を加え、加熱還流下3時間撹拌した。反応終了後、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物19(4.21ｇ、収率62％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.64( d , 1H ) , 8.02( br , 1H ) , 7.55( d , 1H ) , 7.33( dd , 1H ) , 6.35( s , 1H ) , 4.21( q , 2H ) , 1.62( s , 6H ) , 1.27( t , 3H ) (Step 1-3)
Ethyl 2-methyl-2- (3-{[2- (trifluoromethyl) pyridin-4-yl] oxy} ureido) propanoate: Compound 19
To a solution of compound 18 (6.04 g) in THF (40 ml) was added ethyl 2-amino-2-methylpropionate (2.93 g), and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 19 (4.21 g, yield 62%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.64 (d, 1 H), 8.02 (br, 1 H), 7.55 (d, 1 H), 7.33 (dd, 1 H), 6.35 (s, 1 H), 4.21 (q, 2H), 1.62 (s, 6H), 1.27 (t, 3H)
(工程１－４)
Ethyl 2-(3-ethyl-3-{[2-(trifluoromethyl)pyridin-4-yl]oxy}ureido)-2-methylpropanoate：化合物20
　化合物19(4.21ｇ)をDMF(40ml)に溶解し、炭酸カリウム(4.18ｇ)、ヨードエタン(1.97ｇ)を加え、氷冷下5時間撹拌した。反応終了後、酢酸エチルを加え、塩化アンモニウム水溶液で洗浄し、有機層を硫酸マグネシウムにて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物20(3.51ｇ、収率77％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.64( d , 1H ) , 7.50( d , 1H ) , 7.31( dd , 1H ) , 6.25( s , 1H ) , 4.20( q , 2H ) , 3.69( br , 2H ) , 1.57( s , 6H ) , 1.27( t , 3H ) , 1.18( t , 3H ) (Step 1-4)
Ethyl 2- (3-ethyl-3-{[2- (trifluoromethyl) pyridin-4-yl] oxy} ureido) -2-methylpropanoate: Compound 20
Compound 19 (4.21 g) was dissolved in DMF (40 ml), potassium carbonate (4.18 g) and iodoethane (1.97 g) were added, and the mixture was stirred for 5 hours under ice cooling. After completion of the reaction, ethyl acetate was added and washed with an aqueous ammonium chloride solution. The organic layer was dried over magnesium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 20 (3.51 g, yield 77%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.64 (d, 1 H), 7.50 (d, 1 H), 7.31 (dd, 1 H), 6.25 (s, 1 H), 4.20 (q, 2 H), 3.69 (br, 2H), 1.57 (s, 6H), 1.27 (t, 3H), 1.18 (t, 3H)
(工程１－５)
2-(3-Ethyl-3-{[2-(trifluoromethyl)pyridin-4-yl]oxy}ureido)-2-methylpropanoic acid：化合物21
　化合物20(3.51ｇ)のTHF/メタノール/水(32ml/8ml/8ml)溶液に水酸化リチウム一水和物(0.49ｇ)を加え、一晩撹拌した。反応終了後、7%HCl(6.05ｇ)を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。析出した結晶をヘキサンで洗浄し化合物21(2.97ｇ、収率92％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.67( d , 1H ) , 7.50( d , 1H ) , 7.32( dd , 1H ) , 6.07( s , 1H ) , 3.73( br , 2H ) , 1.60( s , 6H ) , 1.18( t , 3H ) (Step 1-5)
2- (3-Ethyl-3-{[2- (trifluoromethyl) pyridin-4-yl] oxy} ureido) -2-methylpropanoic acid: Compound 21
Lithium hydroxide monohydrate (0.49 g) was added to a THF / methanol / water (32 ml / 8 ml / 8 ml) solution of compound 20 (3.51 g), and the mixture was stirred overnight. After completion of the reaction, 7% HCl (6.05 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The precipitated crystals were washed with hexane to obtain Compound 21 (2.97 g, yield 92%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.67 (d, 1 H), 7.50 (d, 1 H), 7.32 (dd, 1 H), 6.07 (s, 1 H), 3.73 (br, 2 H), 1.60 (s, 6H), 1.18 (t, 3H)
(工程１－６)
2-(3-Ethyl-3-{[2-(trifluoromethyl)pyridin-4-yl]oxy}ureido)-N-isobutyl-2-methylpropanamide：化合物22(化合物番号1-5)
　化合物21(0.20ｇ)のアセトニトリル(10ml)溶液にジイソプロピルエチルアミン(0.31ｇ)、イソブチルアミン(0.048ｇ)、TBTU(0.31ｇ)を加え、室温にて一晩撹拌した。反応終了後、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物22(0.21ｇ、収率91％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.63( d , 1H ) , 7.49( d , 1H ) , 7.28( dd , 1H ) , 6.64( s , 1H ) , 6.10( br , 1H ) , 3.69( br , 2H ) , 3.09( dd , 2H ) , 1.84～1.74( m , 1H ) , 1.60( s , 6H ) , 1.18( t , 3H ) , 0.908( d , 6H ) (Step 1-6)
2- (3-Ethyl-3-{[2- (trifluoromethyl) pyridin-4-yl] oxy} ureido) -N-isobutyl-2-methylpropanamide: Compound 22 (Compound No. 1-5)
To a solution of compound 21 (0.20 g) in acetonitrile (10 ml) were added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 22 (0.21 g, yield 91%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.63 (d, 1H), 7.49 (d, 1H), 7.28 (dd, 1H), 6.64 (s, 1H), 6.10 (br, 1H), 3.69 (br, 2H), 3.09 (dd, 2H), 1.84 to 1.74 (m, 1H), 1.60 (s, 6H), 1.18 (t, 3H), 0.908 (d, 6H)
〔実施例２〕
N-[1-(Isobutylamino)-2-methyl-1-oxopropan-2-yl]-2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanamide(化合物番号3-19)の合成 [Example 2]
Synthesis of N- [1- (Isobutylamino) -2-methyl-1-oxopropan-2-yl] -2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanamide (Compound No. 3-19)
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
(工程２－１)
Ethyl 2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanoate：化合物11の合成
　2-(trifluoromethyl)pyridin-4-ol(化合物10、4.00ｇ)をDMF(40ml)に溶解し、Ethyl 2-bromobutanoate(7.18ｇ)、炭酸セシウム(16.0ｇ)を加え、80℃で6時間攪拌した。反応終了後、飽和食塩水を加えて酢酸エチルにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて粗精製し、化合物11(6.95ｇ)を得た。化合物11はそのまま次の反応に使用した。 (Process 2-1)
Ethyl 2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanoate: Synthesis of Compound 11 2- (trifluoromethyl) pyridin-4-ol (Compound 10, 4.00 g) was dissolved in DMF (40 ml), Ethyl 2-bromobutanoate (7.18 g) and cesium carbonate (16.0 g) were added, and the mixture was stirred at 80 ° C. for 6 hours. After completion of the reaction, saturated brine was added and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was roughly purified by silica gel column chromatography to obtain compound 11 (6.95 g). Compound 11 was used as such in the next reaction.
(工程２－２)
2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanoic acid：化合物12の合成
　化合物11(6.95ｇ)のTHF/メタノール/水(32ml/8ml/8ml)溶液に水酸化リチウム一水和物(1.13ｇ)を加え、一晩撹拌した。反応終了後、7%HCl(14.1ｇ)を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。析出した結晶をヘキサンで洗浄し化合物12(4.80ｇ、2工程収率79％)を得た。
　1H-NMR(DMSO-d6 , δ(ppm)) 8.55( d , 1H ) , 7.39( d , 1H ) , 7.20( dd , 1H ) , 5.09( dd , 1H ) , 2.01～1.87 ( m , 2H ) , 0.99( t , 3H ) (Step 2-2)
2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanoic acid: Synthesis of Compound 12 Lithium hydroxide monohydrate in a THF / methanol / water (32ml / 8ml / 8ml) solution of Compound 11 (6.95g) The Japanese product (1.13 g) was added and stirred overnight. After completion of the reaction, 7% HCl (14.1 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The precipitated crystals were washed with hexane to obtain Compound 12 (4.80 g, 2-step yield 79%).
1 H-NMR (DMSO-d6, δ (ppm)) 8.55 (d, 1H), 7.39 (d, 1H), 7.20 (dd, 1H), 5.09 (dd, 1H), 2.01 to 1.87 (m, 2H) , 0.99 (t, 3H)
(工程２－３)
Methyl 2-methyl-2-(2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanamido)propanoate：化合物13の合成
　化合物12(2.50ｇ)のDMSO(30ml)溶液にジイソプロピルエチルアミン(7.76ｇ)、2-アミノ-2-メチルプロピオン酸メチル塩酸塩(1.69ｇ)、TBTU(5.14ｇ)を加え、室温にて3時間撹拌した。反応終了後、反応液を塩化アンモニウム水に注加し、酢酸エチルにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物13(3.28ｇ、収率94％、融点75-77℃)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.59( d , 1H ) , 7.26( d , 1H ) , 7.01( dd , 1H ) , 6.77( s , 1H ) , 4.59( t , 1H ) , 3.73( s , 3H ) , 2.06～1.99( m , 2H ) , 1.55( s , 3H ) , 1.54( s , 3H ) , 1.05( t , 3H ) (Step 2-3)
Methyl 2-methyl-2- (2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanamido) propanoate: Synthesis of Compound 13 Compound 12 (2.50 g) in DMSO (30 ml) solution in diisopropylethylamine (7.76 g), 2-amino-2-methylpropionic acid methyl hydrochloride (1.69 g) and TBTU (5.14 g) were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into aqueous ammonium chloride and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 13 (3.28 g, yield 94%, melting point 75-77 ° C.).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.59 (d, 1 H), 7.26 (d, 1 H), 7.01 (dd, 1 H), 6.77 (s, 1 H), 4.59 (t, 1 H), 3.73 (s, 3H), 2.06 to 1.99 (m, 2H), 1.55 (s, 3H), 1.54 (s, 3H), 1.05 (t, 3H)
(工程２－４)
Methyl 2-methyl-2-(2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanamido)propanoic acid：化合物14の合成
　化合物13(8.44ｇ)のTHF/メタノール/水(60ml/15ml/15ml)溶液に水酸化リチウム一水和物(1.36ｇ)を加え、一晩撹拌した。反応終了後、7%HCl(17.0ｇ)を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。析出した結晶をヘキサンで洗浄し化合物14(7.28ｇ、収率93％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.56( d , 1H ) , 7.27( d , 1H ) , 7.19( s , 1H ) , 7.02( dd , 1H ) , 4.58( t , 1H ) , 2.06～1.99( m , 2H ) , 1.59( s , 3H ) , 1.55( s , 3H ) , 1.05( t , 3H ) (Step 2-4)
Methyl 2-methyl-2- (2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanamido) propanoic acid: Synthesis of Compound 14 Compound 13 (8.44 g) in THF / methanol / water (60 ml / 15 ml Lithium hydroxide monohydrate (1.36 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (17.0 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The precipitated crystals were washed with hexane to obtain Compound 14 (7.28 g, yield 93%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.56 (d, 1H), 7.27 (d, 1H), 7.19 (s, 1H), 7.02 (dd, 1H), 4.58 (t, 1H), 2.06 to 1.99 (m, 2H), 1.59 (s, 3H), 1.55 (s, 3H), 1.05 (t, 3H)
(工程２－５)
N-[1-(Isobutylamino)-2-methyl-1-oxopropan-2-yl]-2-{[2-(trifluoromethyl)pyridin-4-yl]oxy}butanamide：化合物15の合成
　化合物14(0.20ｇ)のアセトニトリル(10ml)溶液にジイソプロピルエチルアミン(0.31ｇ)、イソブチルアミン(0.048ｇ)、TBTU(0.31ｇ)を加え、室温にて3時間撹拌した。反応終了後、溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物15(化合物番号3-19、0.21ｇ、収率91％、融点112-113℃)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm))8.58( d , 1H ) , 7.25( d , 1H ) , 7.22( s , 1H ) , 7.00( dd , 1H ) , 6.09( br , 1H ) , 4.59( t , 1H ) , 3.14～3.03( m , 2H ) , 2.06～1.99( m , 2H ) , 1.82～1.72( m , 1H ) , 1.61( s , 3H ) , 1.55( s , 3H ) , 1.04( t , 3H ) , 0.902( d , 3H ) , 0.900( d , 3H ) (Step 2-5)
N- [1- (Isobutylamino) -2-methyl-1-oxopropan-2-yl] -2-{[2- (trifluoromethyl) pyridin-4-yl] oxy} butanamide: Synthesis of Compound 15 Compound 14 (0.20 g ) In acetonitrile (10 ml) was added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain Compound 15 (Compound No. 3-19, 0.21 g, yield 91%, melting point 112-113 ° C.). It was.
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.58 (d, 1 H), 7.25 (d, 1 H), 7.22 (s, 1 H), 7.00 (dd, 1 H), 6.09 (br, 1 H), 4.59 (t, 1H), 3.14 ~ 3.03 (m, 2H), 2.06 ~ 1.99 (m, 2H), 1.82-1.72 (m, 1H), 1.61 (s, 3H), 1.55 (s, 3H), 1.04 ( t, 3H), 0.902 (d, 3H), 0.900 (d, 3H)
〔実施例３〕
4-Bromo-2-ethyl-N-{2-[4-(ethylsulfonyl)pyridin-2-yl]propan-2-yl}-2,3-dihydrofuro[3,2-c]pyridine-2-carboxamide(化合物番号4-4)の合成 Example 3
4-Bromo-2-ethyl-N- {2- [4- (ethylsulfonyl) pyridin-2-yl] propan-2-yl} -2,3-dihydrofuro [3,2-c] pyridine-2-carboxamide ( Synthesis of Compound No. 4-4)
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
(工程３－１)
Ethyl 4-bromo-2,3-dihydrofuro[3,2-c]pyridine-2-carboxylate：化合物2の合成
　2-Bromo-3-methyl-4-nitropyridine(16.5ｇ)をTHF(70ml)に溶解し、グリオキシ酸エチル(47％トルエン溶液：24.7ｇ)およびTBAF(1M THF溶液：190ml)を加え、室温にて2日間攪拌した。反応終了後、飽和炭酸水素ナトリウム水溶液を加えて酢酸エチルにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物2( 11.1ｇ、収率54％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 8.13( d , 1H ) , 6.83 ( d , 1H ) , 5.30( dd , 1H ) , 4.30( q , 2H ) , 3.57( dd , 1H ) , 3.37( dd , 1H ) , 1.34( t , 3H ) (Process 3-1)
Ethyl 4-bromo-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 2 2-Bromo-3-methyl-4-nitropyridine (16.5 g) is dissolved in THF (70 ml). , Ethyl glyoxyate (47% toluene solution: 24.7 g) and TBAF (1M THF solution: 190 ml) were added, and the mixture was stirred at room temperature for 2 days. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain compound 2 (11.11 g, yield 54%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.13 (d, 1H), 6.83 (d, 1H), 5.30 (dd, 1H), 4.30 (q, 2H), 3.57 (dd, 1H), 3.37 (dd, 1H), 1.34 (t, 3H)
(工程３－２)
Ethyl 4-bromo-2-ethyl-2,3-dihydrofuro[3,2-c]pyridine-2-carboxylate：化合物3の合成
　化合物2(9.36ｇ)のTHF(241ml)溶液を－78℃に冷却し、HMPA(6.16ｇ)、EtI(6.44ｇ)を加え、NaHMDS(1.9M：21.7ml)を滴下した。－78℃で30分撹拌した後、室温で1時間撹拌した。反応終了後、塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物3( 6.14ｇ、収率59％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 8.11( d , 1H ) , 6.80 ( d , 1H ) , 4.31～4.25( m , 2H ) , 3.55( d , 1H ) , 3.18( d , 1H ) , 2.18～1.97( m , 2H ) , 1.32( t , 3H ) , 1.00( t , 3H ) (Step 3-2)
Ethyl 4-bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 3 A THF (241 ml) solution of Compound 2 (9.36 g) was cooled to -78 ° C. , HMPA (6.16 g) and EtI (6.44 g) were added, and NaHMDS (1.9 M: 21.7 ml) was added dropwise. After stirring at −78 ° C. for 30 minutes, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 3 (6.14 g, yield 59%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.11 (d, 1H), 6.80 (d, 1H), 4.31 ~ 4.25 (m, 2H), 3.55 (d, 1H), 3.18 (d, 1H ), 2.18 to 1.97 (m, 2H), 1.32 (t, 3H), 1.00 (t, 3H)
(工程３－３)
4-Bromo-2-ethyl-2,3-dihydrofuro[3,2-c]pyridine-2-carboxylic acid：化合物4の合成
　化合物3(2.99ｇ)のTHF/MeOH/H2O(32ml/8ml/8ml)溶液に水酸化リチウム一水和物(0.46ｇ)を加え、一晩撹拌した。反応終了後、7%HCl(5.74ｇ)を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去して化合物4( 2.99ｇ)を得た。化合物4は精製することなく次の反応に使用した。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 9.00( br , 1H ) , 8.20( d , 1H ) , 6.84 ( d , 1H ) , 3.62( d , 1H ) , 3.22( d , 1H ) , 2.25～2.01( m , 2H ) , 1.06( t , 3H ) (Step 3-3)
4-Bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylic acid: Synthesis of Compound 4 Compound 3 (2.99 g) in THF / MeOH / H 2 O (32 ml / 8 ml / 8 ml) Lithium hydroxide monohydrate (0.46 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (5.74 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer for drying and filtration, and then the solvent was distilled off under reduced pressure to obtain Compound 4 (2.99 g). Compound 4 was used in the next reaction without purification.
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 9.00 (br, 1H), 8.20 (d, 1H), 6.84 (d, 1H), 3.62 (d, 1H), 3.22 (d, 1H), 2.25 to 2.01 (m, 2H), 1.06 (t, 3H)
(工程３－４)
4-Bromo-2-ethyl-N-{2-[4-(ethylthio)pyridin-2-yl]propan-2-yl}-2,3-dihydrofuro[3,2-c]pyridine-2-carboxamide：化合物5の合成
　化合物4をジクロロメタン60mlに溶解し、2-[4-(ethylthio)pyridin-2-yl]propan-2-amine(2.16ｇ)、EDCI塩酸塩(2.68ｇ)、HOBt(1.49ｇ)、トリエチルアミン(2.02ｇ)を加え、室温にて5時間撹拌した。反応終了後、塩化アンモニウム水溶液を加えてジクロロメタンにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物5( 3.53ｇ、2工程収率78％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 8.81( s , 1H ) , 8.29( d , 1H ) , 8.13( d , 1H ) , 7.14( d , 1H ) , 7.01( dd , 1H ) , 6.86( d , 1H ) , 3.58( d , 1H ) , 3.14( d , 1H ) , 3.00( q , 2H ) , 2.24～2.15( m , 1H ) ,  1.99～1.90( m , 1H ) , 1.74( s , 3H ) , 1.73( s , 3H ) , 1.39( t , 3H ) , 1.00( t , 3H ) (Process 3-4)
4-Bromo-2-ethyl-N- {2- [4- (ethylthio) pyridin-2-yl] propan-2-yl} -2,3-dihydrofuro [3,2-c] pyridine-2-carboxamide: Synthesis of Compound 5 Compound 4 is dissolved in 60 ml of dichloromethane, 2- [4- (ethylthio) pyridin-2-yl] propan-2-amine (2.16 g), EDCI hydrochloride (2.68 g), HOBt (1.49 g) , Triethylamine (2.02 g) was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, an aqueous ammonium chloride solution was added and extracted with dichloromethane. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain compound 5 (3.53 g, 2-step yield 78%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.81 (s, 1H), 8.29 (d, 1H), 8.13 (d, 1H), 7.14 (d, 1H), 7.01 (dd, 1H), 6.86 (d, 1H), 3.58 (d, 1H), 3.14 (d, 1H), 3.00 (q, 2H), 2.24 to 2.15 (m, 1H), 1.99 to 1.90 (m, 1H), 1.74 (s, 3H), 1.73 (s, 3H), 1.39 (t, 3H), 1.00 (t, 3H)
(工程３－５)
4-Bromo-2-ethyl-N-{2-[4-(ethylsulfonyl)pyridin-2-yl]propan-2-yl}-2,3-dihydrofuro[3,2-c]pyridine-2-carboxamide：化合物6の合成
　化合物5をジクロロメタン60mlに溶解し、氷冷下、mCPBA(3.85ｇ)を加え、室温にて5時間撹拌した。反応終了後、炭酸水素ナトリウム水溶液を加えてジクロロメタンにて抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物6(化合物番号4-4、2.77ｇ、収率73％、融点132-134℃)を得た。
1H-NMR(CDCl3 / TMS , δ(ppm)) 8.79( dd , 1H ) , 8.16( d , 1H ) , 8.02( s , 1H ) , 7.81( d , 1H ) , 7.65( dd , 1H ) , 6.86( d , 1H ) , 3.52( d , 1H ) , 3.16～3.11( m , 3H ) , 2.20～2.11( m , 1H ) , 1.97～1.88( m , 1H ) , 1.78( s , 6H ) , 1.31( t , 3H ) , 1.00( t , 3H ) (Step 3-5)
4-Bromo-2-ethyl-N- {2- [4- (ethylsulfonyl) pyridin-2-yl] propan-2-yl} -2,3-dihydrofuro [3,2-c] pyridine-2-carboxamide: Synthesis of Compound 6 Compound 5 was dissolved in 60 ml of dichloromethane, mCPBA (3.85 g) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, an aqueous sodium hydrogen carbonate solution was added and extracted with dichloromethane. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 6 (Compound No. 4-4, 2.77 g, yield: 73%, melting point: 132-134 ° C.).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.79 (dd, 1H), 8.16 (d, 1H), 8.02 (s, 1H), 7.81 (d, 1H), 7.65 (dd, 1H), 6.86 (d, 1H), 3.52 (d, 1H), 3.16 ~ 3.11 (m, 3H), 2.20 ~ 2.11 (m, 1H), 1.97 ~ 1.88 (m, 1H), 1.78 (s, 6H), 1.31 ( t, 3H), 1.00 (t, 3H)
〔中間体製造例１〕
Ethyl 2-(trifluoromethyl)-2,3-dihydrofuro[3,2-c]pyridine-2-carboxylate：化合物8の合成 [Intermediate Production Example 1]
Ethyl 2- (trifluoromethyl) -2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 8
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
　3-メチル-4-ニトロピリジン(2.00ｇ)をアセトニトリル(40ml)に溶解し、トリフルオロピルビン酸エチル(3.71ｇ)および炭酸カリウム(12.0ｇ)を加え、加熱還流下5時間撹拌した。トリフルオロピルビン酸エチル(3.71ｇ)を追加し、更に加熱還流下1時間撹拌した。反応終了後、塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物8(1.68ｇ、収率44％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 8.42( s , 2H ) , 6.96 ( d , 1H ) , 4.41～4.33( m , 2H ) , 3.75( d , 1H ) , 3.71( d , 1H ) , 1.35( t , 3H ) 3-Methyl-4-nitropyridine (2.00 g) was dissolved in acetonitrile (40 ml), ethyl trifluoropyruvate (3.71 g) and potassium carbonate (12.0 g) were added, and the mixture was stirred with heating under reflux for 5 hours. Ethyl trifluoropyruvate (3.71 g) was added, and the mixture was further stirred with heating under reflux for 1 hr. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 8 (1.68 g, yield 44%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.42 (s, 2H), 6.96 (d, 1H), 4.41 ~ 4.33 (m, 2H), 3.75 (d, 1H), 3.71 (d, 1H ), 1.35 (t, 3H)
〔中間体製造例２〕
Methyl 2-phenyl-2,3-dihydrofuro[3,2-c]pyridine-2-carboxylate：化合物9の合成 [Intermediate Production Example 2]
Methyl 2-phenyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 9
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
　3-メチル-4-ニトロピリジン(0.50ｇ)をアセトニトリル(20ml)に溶解し、ベンゾイルぎ酸メチル(0.89ｇ)、炭酸カリウム(1.49ｇ)およびテトラブチルアンモニウムブロマイド(0.17ｇ)を加え、加熱還流下一晩撹拌した。反応終了後、塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層に硫酸マグネシウムを加えて乾燥、ろ過後、溶媒を減圧留去した。得られた残渣をシリカゲルカラムクロマトグラフィーにて精製し、化合物9(0.66ｇ、収率72％)を得た。
　1H-NMR(CDCl3 / TMS , δ(ppm)) 8.39( d , 1H ) , 8.36( s , 1H ) , 7.57～7.54( m , 2H ) , 7.43～7.34( m , 3H ) , 6.98( d , 1H ) , 4.23( d , 1H ) , 3.77( s , 3H ) , 3.58( d , 1H ) 3-Methyl-4-nitropyridine (0.50 g) is dissolved in acetonitrile (20 ml), methyl benzoylformate (0.89 g), potassium carbonate (1.49 g) and tetrabutylammonium bromide (0.17 g) are added and heated to reflux. Stirred overnight. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain compound 9 (0.66 g, yield 72%).
1 H-NMR (CDCl 3 / TMS, δ (ppm)) 8.39 (d, 1H), 8.36 (s, 1H), 7.57 to 7.54 (m, 2H), 7.43 to 7.34 (m, 3H), 6.98 (d , 1H), 4.23 (d, 1H), 3.77 (s, 3H), 3.58 (d, 1H)
　前述の方法、または特許文献１～特許文献３に記載のようなスキームに従って本発明化合物を製造した。第１表は式(2-1)中、Ｚが酸素原子、Ｒ4とＲ5がメチル基で表される化合物中の置換基を表す。第２表は式(2-1)中、Ｚが酸素原子、Ｒ4とＲ5が一緒になって環を形成している化合物中の置換基を表す。第３表は式(2-2)中、Ｚが酸素原子または硫黄原子、Ｒ1がエチル基、Ｒ4とＲ5がメチル基で表される化合物中の置換基を表す。第４表は式(3)中、Ｚが酸素原子で表される化合物中の置換基を表す。表中には、各化合物の物性として、性状、融点(m.p.)、または屈折率(ｎD)を併せて示す。
　尚、表中、Ｅｔはエチル基、nＰｒはノルマルプロピル基、iＰｒはイソプロピル基、cＰｒはシクロプロピル基、nＢｕはノルマルブチル基、sＢｕはセカンダリーブチル基、tＢｕはターシャリーブチル基、cＢｕはシクロブチル基、nＰｅｎはノルマルペンチル基、iＰｅｎはイソペンチル基、cＨｅｘはシクロヘキシル基を表す。 The compound of the present invention was produced according to the method described above or a scheme as described in Patent Documents 1 to 3. Table 1 represents substituents in the compound represented by the formula (2-1) wherein Z is an oxygen atom and R 4 and R 5 are methyl groups. Table 2 shows the substituents in the compound in which Z is an oxygen atom and R 4 and R 5 together form a ring in formula (2-1). Table 3 shows the substituents in the compounds represented by formula (2-2) wherein Z is an oxygen atom or sulfur atom, R 1 is an ethyl group, and R 4 and R 5 are methyl groups. Table 4 shows the substituents in the compound in which Z is an oxygen atom in formula (3). In the table, properties, melting point (mp), or refractive index (n D ) are also shown as physical properties of each compound.
In the table, Et is an ethyl group, n Pr is a normal propyl group, i Pr is an isopropyl group, c Pr is a cyclopropyl group, n Bu is a normal butyl group, s Bu is a secondary butyl group, and t Bu is tertiary butyl. Group, c Bu represents a cyclobutyl group, n Pen represents a normal pentyl group, i Pen represents an isopentyl group, and c Hex represents a cyclohexyl group.
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
　第１表～第４表に示した化合物のうち、粘性オイルまたはアモルファスの物性の化合物については1Ｈ－ＮＭＲ(ＣＤＣｌ3)を測定した。第５表にその測定値を示す。 Among the compounds shown in Tables 1 to 4, 1 H-NMR (CDCl 3 ) was measured for viscous oils or amorphous physical compounds. Table 5 shows the measured values.
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
〔製剤処方〕
　本発明の有害生物防除剤の製剤実施例を若干示すが、添加物および添加割合は、これら実施例に限定されるべきものではなく、広範囲に変化させることが可能である。製剤実施例中の部は重量部を示す。製剤実施例中の％は重量％を示す。
　農園芸用および水稲用の製剤処方を示す。 [Prescription formulation]
Although some formulation examples of the pest control agent of the present invention are shown, the additives and addition ratios should not be limited to these examples, and can be varied in a wide range. The part in a formulation example shows a weight part. % In the formulation examples represents% by weight.
The formulation for agricultural and horticultural use and paddy rice is shown.
製剤実施例１　(水和剤)
　本発明のアミド化合物４０部、珪藻土５３部、高級アルコール硫酸エステル４部、およびアルキルナフタレンスルホン酸塩３部を均一に混合して微細に粉砕して、有効成分４０％の水和剤を得た。 Formulation Example 1 (wettable powder)
40 parts of amide compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate were uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient. .
製剤実施例２　(乳剤)
　本発明のアミド化合物３０部、キシレン３３部、ジメチルホルムアミド３０部、およびポリオキシエチレンアルキルアリルエーテル７部を混合溶解して、有効成分３０％の乳剤を得た。 Formulation Example 2 (Emulsion)
30 parts of the amide compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether were mixed and dissolved to obtain an emulsion of 30% active ingredient.
製剤実施例３　(乳剤)
　本発明のアミド化合物５部、ジメチルホルムアミド９３．６部、およびポリオキシエチレンアルキルアリールエーテル１．４部を混合溶解して、有効成分５％の乳剤を得た。 Formulation Example 3 (Emulsion)
5 parts of the amide compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain an emulsion containing 5% active ingredient.
製剤実施例４　(粒剤)
　本発明のアミド化合物５部、タルク４０部、クレー３８部、ベントナイト１０部、およびアルキル硫酸ソーダ７部を均一に混合して微細に粉砕後、直径０．５～１．０ｍｍの粒状に造粒して有効成分５％の粒剤を得た。 Formulation Example 4 (Granule)
5 parts of the amide compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated into granules having a diameter of 0.5 to 1.0 mm As a result, granules having an active ingredient content of 5% were obtained.
製剤実施例５　(粒剤)
　本発明のアミド化合物５部、クレー７３部、ベントナイト２０部、ジオクチルスルホサクシネートナトリウム塩１部、およびリン酸カリウム１部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分５％の粒剤を得た。 Formulation Example 5 (Granule)
After 5 parts of the amide compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and kneaded well, followed by granulation drying As a result, granules having an active ingredient content of 5% were obtained.
製剤実施例６　(懸濁剤)
　本発明のアミド化合物１０部、ポリオキシエチレンアルキルアリルエーテル４部、ポリカルボン酸ナトリウム塩２部、グリセリン１０部、キサンタンガム０．２部、および水７３．８部を混合し、粒度が３μｍ以下になるまで湿式粉砕し、有効成分１０％の懸濁剤を得た。 Formulation Example 6 (Suspension)
Mix 10 parts of the amide compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water to reduce the particle size to 3 μm A wet pulverizing agent was obtained until the suspension became 10% active ingredient.
　内部寄生虫防除剤もしくは駆除剤の製剤処方を示す。 Indicates the formulation of an internal parasite control or control agent.
製剤実施例７　(顆粒剤)
　本発明のアミド化合物５部を有機溶媒中で溶解させて溶液を得、該溶液をカオリン９４部およびホワイトカーボン１部の上に噴霧し、次いで溶媒を減圧下蒸発させ、顆粒剤を得た。この種の顆粒は動物の餌と混合して使用することもできる。 Formulation Example 7 (Granule)
5 parts of the amide compound of the present invention was dissolved in an organic solvent to obtain a solution. The solution was sprayed on 94 parts of kaolin and 1 part of white carbon, and then the solvent was evaporated under reduced pressure to obtain granules. This type of granule can also be used in admixture with animal food.
製剤実施例８　(注入剤)
　本発明のアミド化合物０．１～１部とラッカセイ油９９～９９．９部を均一に混合し、次いで滅菌フィルターによりろ過滅菌し、注入剤を得た。 Formulation Example 8 (Injection)
0.1 to 1 part of the amide compound of the present invention and 99 to 99.9 parts of peanut oil were uniformly mixed, and then sterilized by filtration through a sterilizing filter to obtain an injection.
製剤実施例９　(ポアオン剤)
　本発明のアミド化合物５部、ミリスチン酸エステル１０部、およびイソプロパノール８５部を均一に混合してポアオン剤を得た。 Formulation Example 9 (Pour-on agent)
A pour-on agent was obtained by uniformly mixing 5 parts of the amide compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.
製剤実施例１０　(スポットオン剤)
　本発明のアミド化合物１０～１５部、パルミチン酸エステル１０部、およびイソプロパノール７５～８０部を均一に混合してスポットオン剤を得た。 Formulation Example 10 (Spot-on agent)
The spot-on agent was obtained by uniformly mixing 10 to 15 parts of the amide compound of the present invention, 10 parts of palmitate ester and 75 to 80 parts of isopropanol.
製剤実施例１１　(スプレー剤)
　本発明のアミド化合物１部、プロピレングリコール１０部、およびイソプロパノール８９部を均一に混合してスプレー剤を得た。 Formulation Example 11 (Spray agent)
A spray agent was obtained by uniformly mixing 1 part of the amide compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol.
〔生物試験〕
　本発明化合物が、殺ダニ剤または内部寄生虫防除剤の有効成分として有用であることを以下の試験例で示す。下記試験例中のｐｐｍは重量ｐｐｍを示す。 [Biological test]
The following test examples show that the compound of the present invention is useful as an active ingredient of an acaricide or an endoparasite control agent. In the following test examples, ppm indicates weight ppm.
(試験例１)　カンザワハダニに対する効力試験
　３寸鉢でインゲンを育苗し、初生葉上に、岡山県産のカンザワハダニ雌成虫を８頭接種した。次いで前記製剤実施例３の乳剤を化合物濃度１２５ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を前記インゲンに散布した。該インゲンを、温度２５℃、湿度６５％の恒温室内に置いた。薬剤散布から１０日経過したときにダニの生死を調査した。試験は２反復で行った。 (Test example 1) Efficacy test against Kanzawa spider mite Green beans were bred in 3 inch pots, and 8 female Kanzawa spider mites from Okayama Prefecture were inoculated on primary leaves. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of ticks were examined when 10 days had elapsed since the application of the drug. The test was performed in duplicate.
　第６表に示す番号の化合物について、カンザワハダニに対する効力試験を行った。いずれの化合物も９０％以上の殺虫率を示した。 The compounds with the numbers shown in Table 6 were tested for potency against the Kanzawa spider mite. All the compounds showed an insecticidal rate of 90% or more.
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
(試験例２)　ナミハダニに対する効力試験
　３寸鉢でインゲンを育苗し、初生葉上に、青森県産のナミハダニ雌成虫を８頭接種した。次いで前記製剤実施例３の乳剤を化合物濃度１２５ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を前記インゲンに散布した。該インゲンを、温度２５℃、湿度６５％の恒温室内に置いた。薬剤散布から１０日経過したときにダニの生死を調査した。試験は２反復で行った。 (Test Example 2) Efficacy test against nymph spider mites Kidney seedlings were bred in 3 inch pots, and 8 adult nymph mite from Aomori Prefecture were inoculated on primary leaves. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of ticks were examined when 10 days had elapsed since the application of the drug. The test was performed in duplicate.
　第７表に示す番号の化合物について、ナミハダニに対する効力試験を行った。いずれの化合物も９０％以上の殺虫率を示した。 The compounds with the numbers shown in Table 7 were tested for potency against the spider mite. All the compounds showed an insecticidal rate of 90% or more.
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037
(試験例３)　ミカンハダニに対する効力試験１
　シャーレに入れたミカン葉上に、和歌山県産のミカンハダニ雌成虫を８頭接種した。次いで前記製剤実施例３の乳剤を化合物濃度１２５ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を回転散布塔にて前記ミカン葉に散布した。該ミカン葉を、温度２５℃、湿度６５％の恒温室内に置いた。薬剤散布から１０日経過したときに、ダニの生死を調査した。試験は２反復で行った。 (Test Example 3) Efficacy test 1 against citrus mite
Eight female citrus spider mites from Wakayama Prefecture were inoculated on the mandarin leaves placed in the petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the tangerine leaves in a rotary spray tower. The tangerine leaf was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
　第８表に示す化合物について、ミカンハダニに対する効力試験を行った。いずれの化合物もミカンハダニに対して９０％以上の殺虫率を示した。 The compounds shown in Table 8 were tested for potency against citrus red mite. All the compounds showed an insecticidal rate of 90% or more against citrus red mite.
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
(試験例４)　ミカンハダニに対する効力試験２
　シャーレに入れたミカン葉上に、神奈川県産のミカンハダニ雌成虫を８頭接種した。次いで前記製剤実施例３の乳剤を化合物濃度１２５ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を回転散布塔にて前記ミカン葉に散布した。該ミカン葉を、温度２５℃、湿度６５％の恒温室内に置いた。薬剤散布から１０日経過したときに、ダニの生死を調査した。試験は２反復で行った。 (Test Example 4) Efficacy test 2 against citrus mite
Eight female citrus red spider mites from Kanagawa Prefecture were inoculated on the mandarin orange leaves placed in the petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the tangerine leaves in a rotary spray tower. The tangerine leaf was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
　第９表に示す化合物について、ミカンハダニに対する効力試験を行った。いずれの化合物もミカンハダニに対して９０％以上の殺虫率を示した。 The compounds shown in Table 9 were tested for potency against citrus red mite. All the compounds showed an insecticidal rate of 90% or more against citrus red mite.
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039
(試験例５)　リンゴハダニに対する効力試験
　シャーレに入れたリンゴ葉上に、青森県産のリンゴハダニ雌成虫を８頭接種した。次いで前記製剤実施例３の乳剤を化合物濃度１２５ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を回転散布塔にて前記リンゴ葉に散布した。該リンゴ葉を、温度２５℃、湿度６５％の恒温室内に置いた。薬剤散布から１０日経過したときに、ダニの生死を調査した。試験は２反復で行った。 (Test Example 5) Efficacy test against apple spider mite Eight female spider mites from Aomori Prefecture were inoculated on apple leaves placed in a petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This medicine was sprayed on the apple leaves in a rotary spray tower. The apple leaves were placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
　第１０表に示す化合物について、リンゴハダニに対する効力試験を行った。いずれの化合物もリンゴハダニに対して９０％以上の殺虫率を示した。 The compounds shown in Table 10 were tested for efficacy against apple spider mites. All the compounds showed an insecticidal rate of 90% or more against apple spider mites.
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
(試験例６)ナミハダニに対する効力試験（種子処理試験）
　本発明化合物の各々０．１ｇをアセトン２ｍＬで溶解し、試験用薬液を調整した。１０ｇのダイズ種子を前記試験用薬液に加え風乾させ、プランターに２０粒播種した。７日間２５℃温室に保ったあと、該プランターにナミハダニ（Tetranychus urticae）雌成虫を１０頭／株で接種した。接種１４日後にナミハダニ寄生数を調査し、以下の式により防除率を求めた。試験は２反復で行った。
防除率（％）＝100-{(Nt)／(Nc)×100}
　式中の文字は下記を表している。
　Nc：無処理区における生存ダニ数
　Nt：処理区における生存ダニ数
　化合物番号1-6、3-28の化合物についてナミハダニに対する効力試験を行った。いずれの化合物もナミハダニに対して９０％以上の防除率を示した。 (Test Example 6) Efficacy test against urticae (seed treatment test)
0.1 g of each of the compounds of the present invention was dissolved in 2 mL of acetone to prepare a test chemical solution. 10 g of soybean seeds were added to the test chemical solution, air-dried, and 20 seeds were sown in a planter. After being kept in a greenhouse at 25 ° C. for 7 days, the planter was inoculated with 10 females / strain of female spider mite (Tetranychus urticae). 14 days after the inoculation, the number of spider mite parasites was investigated, and the control rate was determined by the following formula. The test was performed in duplicate.
Control rate (%) = 100-{(Nt) / (Nc) × 100}
The characters in the formula represent the following:
Nc: Number of surviving mites in the untreated group Nt: Number of surviving mites in the treated group The compounds Nos. 1-6 and 3-28 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
(試験例７)ナミハダニに対する効力試験（土壌灌注試験）
　前記製剤実施例３の乳剤を水道水で希釈して濃度が１００ｐｐｍの薬液を調整した。プラスチック鉢植えインゲン苗（初生葉期）に薬液２５ｍｌを株元潅注し、温度２５℃、湿度６０%の恒温室内に置いた。潅注処理３日後にナミハダニ（Tetranychus urticae）雌成虫を１５頭／株で接種し、接種１０日後の生存ダニ数を調査し、以下の式により防除率を求めた。試験は２反復で行った。
防除率（％）＝100-{(Nt)／(Nc)×100}
　式中の文字は下記を表している。
　Nc：無処理区における生存ダニ数
　Nt：処理区における生存ダニ数
　化合物番号3-28、3-53の化合物についてナミハダニに対する効力試験を行った。いずれの化合物もナミハダニに対して９０％以上の防除率を示した。 (Test Example 7) Efficacy test against urticae (soil irrigation test)
The emulsion of Formulation Example 3 was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm. A plastic potted kidney bean seedling (primary leaf stage) was irrigated with 25 ml of chemical solution and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. Three days after the irrigation treatment, adult female worms (Tetranychus urticae) were inoculated at 15 heads / strain, the number of surviving ticks 10 days after the inoculation was examined, and the control rate was determined by the following formula. The test was performed in duplicate.
Control rate (%) = 100-{(Nt) / (Nc) × 100}
The characters in the formula represent the following:
Nc: Number of surviving mites in the untreated group Nt: Number of surviving mites in the treated group The compounds Nos. 3-28 and 3-53 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
(試験例８)ナミハダニに対する効力試験（浸根試験）
　前記製剤実施例３の乳剤を水道水で希釈して濃度が９．４ｐｐｍの薬液を調整した。インゲン苗（初生葉期）の根部を洗い、根を露出させ、薬液に浸漬処理した。その後温度２５℃、湿度６０％の恒温室内に置いた。浸漬処理３日後にナミハダニ（Tetranychus urticae）雌成虫を１０頭／株で接種し、接種１４日後の生存雌成虫数を調査し、以下の式により防除率を求めた。試験は２反復で行った。
防除率（％）＝100-{(Nt)／(Nc)×100}
　式中の文字は下記を表している。
　Nc：無処理区における生存ダニ数
　Nt：処理区における生存ダニ数
　化合物番号1-6、1-15、3-27、3-28、3-53、3-71の化合物についてナミハダニに対する効力試験を行った。いずれの化合物もナミハダニに対して９０％以上の防除率を示した。 (Test Example 8) Efficacy test against the spider mite (Deep root test)
The emulsion of Preparation Example 3 was diluted with tap water to prepare a chemical solution having a concentration of 9.4 ppm. The root part of the kidney seedling (primary leaf stage) was washed, the root was exposed, and immersed in a chemical solution. Then, it was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. Three days after the immersion treatment, adult female worms (Tetranychus urticae) were inoculated at 10 heads / strain, the number of living female adults 14 days after the inoculation was examined, and the control rate was determined by the following formula. The test was performed in duplicate.
Control rate (%) = 100-{(Nt) / (Nc) × 100}
The characters in the formula represent the following:
Nc: Number of surviving ticks in untreated group Nt: Number of surviving ticks in treated group Compound Nos. 1-6, 1-15, 3-27, 3-28, 3-53, 3-71 went. All the compounds showed a control rate of 90% or more against the spider mite.
(試験例９)キュウリに対する薬害試験
　前記製剤実施例３の乳剤を化合物濃度１５０ｐｐｍとなるように水で希釈して薬剤を得た。３寸鉢に植えたキュウリ苗(第二本葉展開期)に薬剤を散布し温室内に置いた。散布７日後に薬害の有無を調査した。薬害は指数０(薬害なし)～１０(枯死)の１１段階で評価した。
　化合物番号1-6、1-14、1-15、3-11、3-28、3-42の化合物についてキュウリに対する薬害試験を行った。いずれの化合物も指数０(薬害なし)であった。 (Test Example 9) Chemical damage test for cucumber The emulsion of Formulation Example 3 was diluted with water to a compound concentration of 150 ppm to obtain a drug. The cucumber seedlings planted in 3 inch pots (second true leaf development stage) were sprayed with the drug and placed in the greenhouse. The presence or absence of chemical damage was investigated 7 days after spraying. The phytotoxicity was evaluated in 11 grades, index 0 (no phytotoxicity) to 10 (dead).
The compound nos. 1-6, 1-14, 1-15, 3-11, 3-28 and 3-42 were subjected to a phytotoxicity test against cucumber. All compounds had an index of 0 (no phytotoxicity).
(試験例１０)　ニワトリ回虫(Ascaridia galli)および豚腸結節虫(Oesophagostomum dentatum)に対するin vitro効力試験
　腸在(gut-welling)の幼虫期の二つの寄生虫：ニワトリ回虫(Ascaridiagalli)、幼虫３期(「Ｌ３」)；および豚腸結節虫(Oesophagostomum dentatum)、幼虫３期および４期(それぞれ「Ｌ３」および「Ｌ４」)を用いてin vitroで、本発明化合物の生物活性を調べた。これらの試験を行う場合、各種濃度の本発明化合物のＤＭＳＯ溶液を調製し、９６ウェルマイクロタイタープレートでインキュベートした。次に、ウェル当たり幼虫２０匹で寄生虫を接種した。生物活性は、顕微鏡検査によって調査した。顕微鏡検査には、ＤＭＳＯ対照と比較した死亡率、傷害、運動性、発達の進行および幼虫によるニュートラルレッド取り込みの評価などがある。生物活性は、幼虫のうちの少なくとも１匹が死亡、傷害、運動性の変化、発達進行における変化またはニュートラルレッド取り込み無しを示す濃度である最小有効濃度(「ＭＥＣ」)によって定義した。
　第１１表に示す化合物について、ニワトリ回虫(Ascaridia galli)および豚腸結節虫(Oesophagostomum dentatum)に対するin vitro効力試験を行った。いずれの化合物も２５μＭ以下のＭＥＣで１種以上の対象の寄生虫に対して活性を示した。 (Test Example 10) In vitro efficacy test against Ascaridia galli and Oesophagostomum dentatum Two parasites in the larval stage of the gut-welling: Ascaridiagalli, 3rd stage of larvae ("L3"); and Oesophagostomum dentatum, 3rd and 4th stages of larvae ("L3" and "L4", respectively), and the biological activity of the compounds of the present invention was examined in vitro. When performing these tests, DMSO solutions of various concentrations of the compounds of the present invention were prepared and incubated in 96-well microtiter plates. Next, parasites were inoculated with 20 larvae per well. Biological activity was investigated by microscopy. Microscopic examination includes assessment of mortality, injury, motility, progression of development and neutral red uptake by larvae compared to DMSO controls. Biological activity was defined by the minimum effective concentration (“MEC”), the concentration at which at least one of the larvae exhibited death, injury, changes in motility, changes in developmental progression or no neutral red uptake.
The compounds shown in Table 11 were subjected to in vitro efficacy tests against Ascaridia galli and Oesophagostomum dentatum. All of the compounds showed activity against one or more target parasites at an MEC of 25 μM or less.
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041
　本発明のアミド化合物は、農作物に対する薬害がなく、農作物や衛生面で問題となる有害生物、特にダニ類および害虫を効果的に防除することができる。 The amide compound of the present invention has no phytotoxicity to crops and can effectively control pests that are problematic in crops and sanitation, especially mites and pests.

Claims (5)

  1. 〔１〕　下記式(1)で表される化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000001
     　式(1)中、
    　Ｚは、酸素原子または硫黄原子である。
    　Ａは、式(A-1)で表される基、または式(A-2)で表される基である。
    　Ｂは、Ａが式(A-1)で表される基あるとき式(B-1)で表される基であり、Ａが式(A-2)で表される基であるとき式(B-2)で表される基である。
    Figure JPOXMLDOC01-appb-C000002
     　式(A-1)中、Ｗは窒素原子、またはＣＨである。
    　式(A-1)、および(A-2)中、
    　＊は結合位置を表す。
    　Ｘは、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、アミノ基、置換若しくは無置換のＣ１～６アルキルアミノ基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルキルアミノカルボニル基、置換若しくは無置換のＣ１～６アルコキシイミノＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ１～６アルコキシスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のヘテロアリールオキシ基、ニトロ基、またはシアノ基である。
    　ｎは、Ｘの置換数を示し且つ０～３のいずれかの整数である。ｎが２または３のときＸは互いに同じでも異なってもよい。
    　Ｒ1は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、またはフェニル基である。
    　Ｒ2およびＲ3は、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１～６アルキル基である。
    Figure JPOXMLDOC01-appb-C000003
     　式(B-1)および(B-2)中、
    　＊は結合位置を示す。
    　Ｒ4およびＲ5は、それぞれ独立して、水素原子、または無置換のＣ１～６のアルキル基である。
    　Ｒ4およびＲ5は繋がって、それらが結合する炭素原子とともに環を形成してもよい。
    　Ｒ6は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のアミノチオカルボニル基である。
    　Ｒ7は、置換若しくは無置換のアミノカルボニル基、または置換若しくは無置換のヘテロアリール基である。     [1] A compound represented by the following formula (1) or a salt thereof.
    Figure JPOXMLDOC01-appb-C000001
     In formula (1),
    Z is an oxygen atom or a sulfur atom.
    A is a group represented by the formula (A-1) or a group represented by the formula (A-2).
    B is a group represented by the formula (B-1) when A is a group represented by the formula (A-1), and B is a group represented by the formula (A-2) It is a group represented by B-2).
    Figure JPOXMLDOC01-appb-C000002
     In the formula (A-1), W is a nitrogen atom or CH.
    In formulas (A-1) and (A-2),
    * Represents a bonding position.
    X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy Group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted A C1-6 alkoxysulfonyl group, substituted or unsubstituted C3-8 cycloal Group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted heteroaryloxy group, nitro group, or cyano It is a group.
    n represents the number of substitutions of X and is an integer from 0 to 3. When n is 2 or 3, Xs may be the same or different.
    R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a phenyl group.
    R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
    Figure JPOXMLDOC01-appb-C000003
     In formulas (B-1) and (B-2),
    * Indicates a binding position.
    R 4 and R 5 are each independently a hydrogen atom or an unsubstituted C 1-6 alkyl group.
    R 4 and R 5 may be joined together to form a ring together with the carbon atom to which they are attached.
    R 6 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
    R 7 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted heteroaryl group.
  2. 　式(1)が、式(2)である、請求項１に記載の化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000004
     　式中、Ｚ、Ｗ、Ｘ、ｎ、Ｒ1、Ｒ４、Ｒ５、及びＲ６は請求項１に記載の通りである。     The compound or a salt thereof according to claim 1, wherein the formula (1) is the formula (2).
    Figure JPOXMLDOC01-appb-C000004
     In the formula, Z, W, X, n, R 1 , R 4 , R 5 , and R 6 are as defined in claim 1.
  3. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する有害生物防除剤。 A pest control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof.
  4. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する殺ダニ若しくは殺虫剤。 An acaricide or insecticide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof.
  5. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する内部寄生虫防除または駆除剤。 An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof.
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JP6585328B1 (en) * 2018-04-09 2019-10-02 日本曹達株式会社 Phenoxyurea compounds and pest control agents
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