WO2017164108A1 - Composé hétérocyclique - Google Patents

Composé hétérocyclique Download PDF

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Publication number
WO2017164108A1
WO2017164108A1 PCT/JP2017/010882 JP2017010882W WO2017164108A1 WO 2017164108 A1 WO2017164108 A1 WO 2017164108A1 JP 2017010882 W JP2017010882 W JP 2017010882W WO 2017164108 A1 WO2017164108 A1 WO 2017164108A1
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group
compound
halogen atoms
hereinafter referred
optionally
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Japanese (ja)
Inventor
貴將 田邊
中嶋　祐二
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to certain heterocyclic compounds and harmful arthropod control agents.
  • An object of the present invention is to provide a compound having an excellent control effect against harmful arthropods.
  • a 1 represents a nitrogen atom or CR 4
  • R 4 represents a hydrogen atom, OR 27 , NR 28 R 29 , a cyano group, a nitro group, or a halogen atom
  • Any one of A 2 , A 3 , and A 4 represents a nitrogen atom, and the remainder represents CR 6
  • R 6 is a hydrogen atom
  • one or more halogen atoms optionally C1-C6 may be an alkyl group having a nitro group
  • OR 18, NR 18 R 19 , a cyano group, or a halogen atom
  • a plurality of R 6 is Can be the same or different
  • R 1 is a C1-C10 chain hydrocarbon group having one or more halogen atoms, (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, and one or more halogen atoms (C1-C5 Alkyl
  • R 13 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, one or more A (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having a halogen atom, a phenyl group optionally having one or more substituents selected from group D, or one or more selected from group D
  • R 14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and one or more halogen atoms.
  • R 15 and R 16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, n represents 0, 1 or 2; m represents 0, 1 or 2; x represents 0 or 1; y represents 0, 1, or 2.
  • Group B C1-C6 alkoxy group optionally having one or more halogen atoms, C3-C6 alkenyloxy group optionally having one or more halogen atoms, having one or more halogen atoms
  • Group D C1-C6 chain hydrocarbon group which may have one or more halogen atoms, hydroxy group, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms
  • a C3-C6 alkenyloxy group which may have one or more, a C3-C6 alkynyloxy group which may have one or more halogen atoms, a sulfanyl group, or a C1-C6 which may have one or more halogen atoms.
  • C6 alkylsulfanyl group C1-C6 alkylsulfinyl group optionally having one or more halogen atoms
  • C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, amino group, NHR 21 , NR The group consisting of 21 R 22 , C (O) R 21 group, OC (O) R 21 group, C (O) OR 21 group, cyano group, nitro group, and halogen atom.
  • ⁇ R 21 and R 22 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms ⁇
  • Group E C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, C1-C6 alkoxy group which may have one or more halogen atoms, one or more halogen atoms
  • Group F C1-C6 alkoxy group optionally having one or more halogen atoms, NHR 21 , NR 21 R 22 , cyano group, phenyl optionally having one or more substituents selected from Group D A group, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a group A group consisting of a 3-7-membered non-aromatic heterocyclic group which may have one or more substituents selected from C.
  • Group C C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C6 alkoxy group optionally having one or more halogen atoms, one or more halogen atoms A group consisting of an optionally substituted C3-C6 alkenyloxy group, an optionally substituted C3-C6 alkynyloxy group, and a halogen atom.
  • Group G A group consisting of a halogen atom and a C1-C6 haloalkyl group.
  • an N oxide compound thereof hereinafter, the compound represented by the formula (I) and the N oxide compound thereof will be referred to as the present compound).
  • R 3 is a C1-C6 alkyl group having one or more halogen atoms, NR 11 R 12 , a phenyl group optionally having one or more substituents selected from group D, 1 or 2 nitrogen atoms 6-membered aromatic heterocyclic group (this 6-membered aromatic heterocyclic group may have one or more substituents selected from group D), 1, 2, 3 or 4 nitrogen atoms
  • a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), or a halogen atom
  • R 11 and R 12 The compounds according to any one of [1] to [5], wherein each independently represents a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms.
  • R 1 is a C1-C10 chain hydrocarbon group, or 3 or more with a halogen atom (C1-C5 alkoxy) C2-C5 alkyl group having 3 or more halogen atoms [1] to [6 ] The compound in any one. [8] The compound according to any one of [1] to [6], wherein R 1 is a C1-C6 perfluoroalkyl group.
  • R 1 is an ethyl group
  • a 1 is a nitrogen atom
  • R 3 is a C1-C6 alkyl group having one or more halogen atoms, NR 11 R 12 , one or more substituents selected from group D
  • a 6-membered aromatic heterocyclic group having 1 or 2 nitrogen atoms (the 6-membered aromatic heterocyclic group has one or more substituents selected from the group D;
  • a 5-membered aromatic heterocyclic group containing 1, 2, 3 or 4 nitrogen atoms (the 5-membered aromatic heterocyclic group has one or more substituents selected from group D).
  • R 11 and R 12 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms, and R 1 is The compound according to any one of [1] to [3], which is a C1-C6 perfluoroalkyl group.
  • a harmful arthropod control agent comprising the compound according to any one of [1] to [9] and an inert carrier.
  • a harmful arthropod control composition comprising the compound according to any one of [1] to [9] and an inert carrier.
  • a method for controlling harmful arthropods which comprises applying an effective amount of the compound according to any one of [1] to [9] to harmful arthropods or habitats of harmful arthropods.
  • One or more components selected from the group consisting of group (a), group (b), group (c), group (d) and group (e), and any one of [1] to [9] A composition containing the compound described in 1.
  • the compound of the present invention Since the compound of the present invention has an excellent control activity against harmful arthropods, it is useful as an active ingredient of a harmful arthropod control agent.
  • halogen atoms when it has two or more halogen atoms, these halogen atoms may be the same or different from each other.
  • CX-CY means that the number of carbon atoms is X to Y.
  • C1-C6 means 1 to 6 carbon atoms.
  • the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the “chain hydrocarbon group” represents an alkyl group, an alkenyl group or an alkynyl group.
  • alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group and a hexyl group are mentioned.
  • alkenyl group examples include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, Examples include 1,1-dimethyl-2-propenyl group, 1-ethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group and 5-hexenyl group.
  • alkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples thereof include 2-butynyl group, 4-pentynyl group and 5-hexynyl group.
  • C1-C6 haloalkyl group represents a group in which a hydrogen atom of a C1-C6 alkyl group is substituted with a halogen atom, and examples thereof include a C1-C6 fluoroalkyl group.
  • C1-C6 haloalkyl group examples include chloroethyl group, 2,2,2-trifluoroethyl group, 2-bromo-1,1,2,2-tetrafluoroethyl group, 2,2,3,3 -Tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, and perfluorohexyl group.
  • C1-C6 fluoroalkyl group refers to a group in which a hydrogen atom of a C1-C6 alkyl group is substituted with a fluorine atom, for example, 2,2,2-trifluoroethyl group, 2,2,3,3 -Tetrafluoropropyl group, 1-methyl-2,2,3,3-tetrafluoropropyl group, and perfluorohexyl group.
  • C1-C5 fluoroalkoxy C2-C5 fluoroalkyl group represents a group in which a C1-C5 alkoxy group having one or more fluorine atoms is bonded to a C2-C5 alkyl group having one or more fluorine atoms.
  • C1-C6 perfluoroalkyl group refers to a group in which all hydrogen atoms of a C1-C6 alkyl group are substituted with fluorine atoms.
  • a trifluoromethyl group a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group.
  • Group and nonafluorobutyl group are examples include 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl group and 2,2-difluoro-3- (2,2,2-trifluoroethoxy) propyl group.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • 3-7-membered non-aromatic heterocyclic group means an aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine Ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, or 1,4-thiazepane ring .
  • Examples of the 3-7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from group E include the groups shown below.
  • Examples of “phenyl C1-C3 alkyl group ⁇ the phenyl group in the group may have one or more substituents selected from group D ⁇ ” include, for example, benzyl group, 2-fluorobenzyl group, 4- Examples thereof include a chlorobenzyl group, a 4- (trifluoromethyl) benzyl group, and a 2- [4- (trifluoromethyl) phenyl] ethyl group.
  • “(C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms” means a group in which (C1-C5 alkoxy) moiety and / or (C2-C5 alkyl) moiety has one or more halogen atoms.
  • (C1-C5 alkoxy) C1-C4 alkyl group having 3 or more halogen atoms means a group in which (C1-C5 alkoxy) moiety and / or (C1-C4 alkyl) moiety has 3 or more halogen atoms.
  • 2- (trifluoromethoxy) ethyl group 2,2-difluoro-3- (2,2,2-trifluoroethoxy) propyl group, 3- (2-chloroethoxy) -2,2-difluoro Examples include a propyl group and a 3-methoxy-2,2,3-trifluoropropyl group.
  • (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms means that the (C1-C5 alkylsulfanyl) moiety and / or the (C2-C5 alkyl) moiety has one or more halogen atoms Represents a group, for example, 2,2-difluoro-2- (trifluoromethylsulfanyl) ethyl group.
  • (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms means that the (C1-C5 alkylsulfinyl) moiety and / or the (C2-C5 alkyl) moiety has one or more halogen atoms Represents a group, for example, 2,2-difluoro-2- (trifluoromethanesulfinyl) ethyl group.
  • (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms means that a (C1-C5 alkylsulfonyl) moiety and / or (C2-C5 alkyl) moiety has one or more halogen atoms Represents a group such as 2,2-difluoro-2- (trifluoromethanesulfonyl) ethyl group.
  • the “(C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms” means that the (C3-C6 cycloalkyl) moiety and / or the (C1-C3 alkyl) moiety is one or more.
  • (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from group G means that a (C3-C7 cycloalkyl) moiety and / or a (C1-C3 alkyl) moiety is a group G Represents a group having one or more substituents selected from, for example, (2,2-difluorocyclopropyl) methyl group, [1- (trifluoromethyl) cyclopropyl] methyl group, [2- (trifluoromethyl) Cyclopropyl] methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, 2-cyclopropyl-3,3,3-trifluoropropyl group, and 1,1,2,2-tetra A fluoro-2- [2- (trifluoromethyl) cyclopropyl] ethyl group can be mentioned.
  • the “5- or 6-membered aromatic heterocyclic group” means a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, and the 5-membered aromatic heterocyclic group means a pyrrolyl group, a furyl group, a thienyl group, A pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an oxadiazolyl group, or a thiadiazolyl group.
  • a 6-membered aromatic heterocyclic group is a pyridyl group, pyridazinyl group, pyrimidinyl group, or pyrazinyl group. Represents.
  • the “6-membered aromatic heterocyclic group having 1 or 2 nitrogen atoms” represents a pyridyl group, a pyridazinyl group, a pyrimidinyl group or a pyrazinyl group.
  • “5-membered aromatic heterocyclic group having 1, 2, 3 or 4 nitrogen atoms” means a pyrrolyl group, pyrazolyl group, imidazolyl group, 1,2,4-triazolyl group, 1,2,3-triazolyl group Or a tetrazolyl group.
  • Het the structure represented by the following formula (Hereinafter referred to as Het.
  • # 1 represents a bonding position between Het and R 1 —S (O) m
  • # 2 represents Represents the bonding position of Het and Het.
  • the compound “A 4 is CR 6 , one of A 2 and A 3 is a nitrogen atom and the other is CR 6 ” is a compound in which Het is Het-1 in the compound of the present invention Or a compound that is Het-2.
  • the compound “A 4 is a nitrogen atom and A 2 and A 3 are CR 6 ” represents a compound of the present compound in which Het is Het-3.
  • the N oxide compound is a compound represented by the formula (N-1), a compound represented by the formula (N-2), a compound represented by the formula (N-3), a compound represented by the formula (N-4), Alternatively, the compound represented by the formula (N-5) is represented.
  • N-1 a compound represented by the formula (N-1)
  • N-2 a compound represented by the formula (N-2)
  • N-3 a compound represented by the formula (N-4)
  • N-4 a compound represented by the formula (N-4)
  • N-5 is represented.
  • symbols represent the above meanings, and a plurality of R 6 may be the same or different.
  • Examples of the compound of the present invention include the following compounds.
  • [Aspect 1] A compound in which R 1 is a C1-C10 chain hydrocarbon group having 2 or more halogen atoms or a (C1-C5 fluoroalkoxy) C2-C5 fluoroalkyl group in the compound of the present invention
  • [Aspect 2] A compound in which R 1 is a C1-C10 chain hydrocarbon group having two or more halogen atoms in the compound of the present invention
  • [Aspect 3] A compound in which R 1 is a C1-C10 alkyl group having 3 or more fluorine atoms in the compound of the present invention
  • [Aspect 4] A compound in which R 1 is a C1-C10 perfluoroalkyl group in the compound of the present invention
  • [Aspect 5] A compound in which R 1 is a C2-C10 perfluoroalkyl group in the compound of the present invention
  • a compound of the present invention wherein R 2 is a C1-C3 alkyl group optionally having one or more halogen atoms;
  • a compound of the present invention wherein R 2 is a C1-C6 alkyl group;
  • a compound in which R 2 is a C1-C3 alkyl group in the compound of the present invention;
  • Aspect 9 A compound in which R 2 is a methyl group or an ethyl group in the compound of the present invention;
  • Aspect 10 A compound of the present invention wherein R 2 is an ethyl group;
  • R 3 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group B, and one or more substituents selected from group D.
  • a phenyl group which may have, one 6-membered aromatic heterocyclic group selected from group L (the six-membered aromatic heterocyclic group may have one or more substituents selected from group D; 1) a 5-membered aromatic heterocyclic group selected from group W (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), OR 12 , NR 11 R 12 , NR 11a R 12a , NR 24 NR 11 R 12 , or a compound that is a halogen atom; Group L: Group W: ⁇ Wherein R 26 represents a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 3 is a C1-C6 alkyl group which may have one or more halogen atoms, and a phenyl group which may have one or more substituents selected from Group G 1-membered aromatic heterocyclic group selected from group L (the 6-membered aromatic heterocyclic group may have one or more substituents selected from group G), W-1 to One 5-membered aromatic heterocyclic group selected from W-6 (the 5-membered aromatic heterocyclic group may have one or more substituents selected from Group G), NR 11 R 12 , NR 24 NR 11 R 12 , or a halogen atom, and R 11 , R 12, and R 24 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms.
  • a compound; [Aspect 13] A compound of the present invention, wherein R 3 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a halogen atom; [Aspect 14] A compound of the present invention, wherein R 3 is a C1-C6 alkyl group having one or more halogen atoms, or a halogen atom;
  • R 6 is a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a halogen atom in the compound of the present invention
  • a compound in which A 1 is a nitrogen atom or CR 4 and R 4 is a hydrogen atom or a halogen atom in the compound of the present invention [Aspect 19] A compound in which A 1 is a nitrogen atom or CH in the compound of the present invention. [Aspect 20] A compound in which A 1 is a nitrogen atom in the compound of the present invention.
  • a compound of the present invention, wherein Het is Het-1 or Het-2;
  • Aspect 22 A compound of the present invention, wherein Het is Het-1.
  • Aspect 23 A compound of the present invention, wherein Het is Het-2;
  • Aspect 24 A compound of the present invention, wherein Het is Het-3;
  • R 1 is a C1-C10 chain hydrocarbon group having one or more halogen atoms, and R 2 is an ethyl group;
  • R 1 is a C1-C10 chain hydrocarbon group having one or more halogen atoms
  • R 2 is an ethyl group
  • R 3 is a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from group B, a phenyl group optionally having one or more substituents selected from group G;
  • One 6-membered aromatic heterocyclic group selected from group L (the six-membered aromatic heterocyclic group may have one or more substituents selected from group
  • T 1 and T 2 are each independently a fluorine atom, a chlorine atom, a trifluoromethyl group, or a methyl group.
  • R 101 is a halogen atom, a C1-C5 chain hydrocarbon group having 3 or more halogen atoms
  • T 1 and T 2 are each independently a fluorine atom, a chlorine atom, a trifluoromethyl group, Or a methyl group
  • R 3 is a C1-C6 alkyl group having one or more halogen atoms, NR 11 R 12 , a phenyl group optionally having one or more substituents selected from group D, a nitrogen atom
  • a 6-membered aromatic heterocyclic group having 1 or 2 (the 6-membered aromatic heterocyclic group may have one or more substituents selected from group D), 1, 2, 3 or 4 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), or a halogen atom
  • R 11 and R 12 are each independently have a hydrogen atom or one or more halogen atoms It is also be C1-C3 al
  • R 101 is a halogen atom, a C1-C5 chain hydrocarbon group having 3 or more halogen atoms
  • T 1 and T 2 are each independently a fluorine atom, a chlorine atom, a trifluoromethyl group, Or a methyl group
  • R 3 is a C1-C6 alkyl group having one or more halogen atoms, NR 11 R 12 , a phenyl group optionally having one or more substituents selected from group D, a nitrogen atom
  • a 6-membered aromatic heterocyclic group having 1 or 2 (the 6-membered aromatic heterocyclic group may have one or more substituents selected from group D), 1, 2, 3 or 4 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group may have one or more substituents selected from group D), or a halogen atom
  • R 11 and R 12 are each independently have a hydrogen atom or one or more halogen atoms It is also be C1-C3
  • R 101 is a halogen atom, a C1-C5 chain hydrocarbon group having 3 or more halogen atoms
  • T 1 and T 2 are each independently a fluorine atom, a chlorine atom, a trifluoromethyl group, Or a methyl group
  • R 3 is a C1-C6 alkyl group having one or more halogen atoms, or a halogen atom
  • R 6 is a hydrogen atom, optionally having one or more halogen atoms.
  • the compound of the present invention can be produced, for example, by the following production method.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as aliphatic halogenated hydrocarbons) and nitriles such as acetonitrile (hereinafter referred to as nitriles).
  • Alcohols such as methanol and ethanol (hereinafter referred to as alcohols), acetic acid, water, and mixtures thereof.
  • the oxidizing agent used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.
  • the oxidizing agent When hydrogen peroxide is used as the oxidizing agent, sodium carbonate or a catalyst may be added as necessary.
  • the catalyst used for the reaction include tungstic acid and sodium tungstate.
  • the oxidizing agent is usually in a proportion of 1 to 1.2 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, sodium carbonate or a catalyst may be added as necessary. Examples of the catalyst used in the reaction include sodium tungstate.
  • the oxidizing agent is usually in a proportion of 1 to 2 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol.
  • the reaction temperature is usually in the range of ⁇ 20 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • water is added to the reaction mixture and extracted with an organic solvent, and the organic layer is extracted with an aqueous solution of a reducing agent (for example, sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (for example, sodium bicarbonate) as necessary. Wash.
  • Compound (Ic) can be obtained by drying and concentrating the organic layer.
  • Compound (Ic) can be produced in a one-step reaction (one pot) by reacting compound (Ia) with an oxidizing agent.
  • the reaction can be carried out according to the method for producing compound (Ic) from compound (Ib) using an oxidizing agent in a proportion of usually 2 to 5 mol per 1 mol of compound (Ia).
  • the compound (Ie) of the present invention can be produced according to the method described in Production Method 1, using the compound (Id) instead of the compound (Ia) of the present invention.
  • This invention compound (If) can be manufactured according to the method of the manufacturing method 1 using this invention compound (Ie) instead of this invention compound (Ib).
  • the compound represented by the formula (Ig) (hereinafter referred to as the present compound (Ig)) is composed of the compound represented by the formula (M-1) (hereinafter referred to as the compound (M-1)) and the formula (R). -1) (hereinafter referred to as compound (R-1)) can be produced by reacting in the presence of a base.
  • X 1 represents a halogen atom, and other symbols have the same meaning as described above.
  • Compound (R-1) is a commercially available compound or can be produced according to a known method. The reaction is usually performed in a solvent.
  • solvent used in the reaction examples include tetrahydrofuran (hereinafter referred to as THF), ethers such as ethylene glycol dimethyl ether, methyl tert-butyl ether, and 1,4-dioxane (hereinafter referred to as ethers), toluene, xylene.
  • THF tetrahydrofuran
  • ethers such as ethylene glycol dimethyl ether, methyl tert-butyl ether, and 1,4-dioxane (hereinafter referred to as ethers), toluene, xylene.
  • aromatic hydrocarbons hereinafter referred to as aromatic hydrocarbons
  • DMF dimethylformamide
  • NMP N-methylpyrrolidone
  • dimethylsulfoxide and the like.
  • Polar solvents hereinafter referred to as aprotic polar solvents
  • Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, and alkali metal carbonates such as potassium carbonate and sodium carbonate.
  • compound (M-1) is usually used at a ratio of 1 to 10 mol
  • base is usually used at a ratio of 1 to 10 mol.
  • the reaction temperature is usually in the range of 0 ° C to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (Ig) of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound (Ig) of the present invention comprises a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)).
  • M-2 a compound represented by formula (M-2)
  • R-2 a compound represented by formula (R-2)
  • X 2 represents a chlorine atom, a bromine atom, an iodine atom, a C1-C10 perfluoroalkylsulfonyloxy group, or a tosyloxy group, and other symbols have the same meanings as described above.
  • Compound (R-2) may be a commercially available compound or may be according to a known method. The reaction is usually performed in a solvent.
  • Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride, and alkali metal carbonates. You may add a reducing agent to reaction as needed. Examples of the reducing agent used in the reaction include sodium hydroxymethanesulfinate, tetrakis (dimethylamino) ethylene and the like.
  • compound (R-2) is usually in a proportion of 1 to 10 mol
  • base is usually in a proportion of 1 to 10 mol
  • reducing agent is 0.1 to 2 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of 0 ° C to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (Ig) of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound (Ia) of the present invention can be produced according to the following method. [Wherein X represents a halogen atom, X 4 represents a chlorine atom, a bromine atom, or an iodine atom, M represents Sn (n—C 4 H 9 ) 3 , ZnCl, MgCl, or MgBr; The symbol represents the same meaning as described above. ] First, a method for producing a compound represented by the formula (M-9) (hereinafter referred to as compound (M-9)) will be described.
  • Compound (M-9) is a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) and a compound represented by formula (M-6) (hereinafter referred to as compound (M-6)).
  • M-8 a compound represented by formula (M-8)
  • M-6 a compound represented by formula (M-6)
  • metal catalyst used in the reaction examples include tetrakis (triphenylphosphine) palladium (0), 1,1′-bis (diphenylphosphino) ferrocenepalladium (II) dichloride, tris (dibenzylideneacetone) dipalladium (0), Palladium catalysts such as palladium (II) acetate, nickel catalysts such as bis (cyclooctadiene) nickel (0) and nickel (II) chloride, copper catalysts such as copper (I) iodide and copper (I) chloride, etc. It is done. In the reaction, a ligand, a base and an inorganic halide may be added as necessary.
  • Examples of the ligand used in the reaction include triphenylphosphine, xanthophos, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl, 1,1′-bis (diphenylphosphino) ferrocene, 2- Dicyclohexylphosphino-2 ′, 4 ′, 6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 1,2-bis (diphenylphosphino) ethane, 2,2′-bipyridine 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline and the like.
  • Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases such as triethylamine, diisopropylethylamine, pyridine, and 4- (dimethylamino) pyridine.
  • Examples of the inorganic halide used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride, and alkali metal chlorides such as lithium chloride and sodium chloride.
  • compound (M-6) is usually used in a proportion of 1 to 10 mol
  • metal catalyst is usually used in a proportion of 0.01 to 0.5 mol, relative to 1 mol of compound (M-8).
  • the ligand is usually used in a proportion of 0.01 to 1 mol
  • the base is usually used in a proportion of 0.1 to 5 mol
  • the inorganic halide is usually used in a proportion of 0.1 to 5 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M-6) can be produced, for example, according to the method described in WO 03/024961 or the method described in Organic Process Research & Development, 2004, 8, 192-200. After completion of the reaction, compound (M-9) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound (Ia) of the present invention is produced by reacting the compound (M-9) with a compound represented by the formula (R-3) (hereinafter referred to as compound (R-3)) in the presence of a base. can do.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • the base used for the reaction include alkali metal carbonates and alkali metal hydrides.
  • compound (R-3) is usually used at a ratio of 1 to 10 mol
  • base is usually used at a ratio of 1 to 10 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound (Ia) of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • X is preferably a fluorine atom or a chlorine atom.
  • Reference manufacturing method 1 Compound (M-2) can be produced by reacting compound (M-1) with an alkali metal sulfide.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • the alkali metal sulfide used for the reaction include sodium sulfide and sodium hydrogen sulfide.
  • the sulfurizing agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M-1).
  • the reaction temperature is usually in the range of 0 ° C to 180 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • X 1 is preferably a fluorine atom or a chlorine atom.
  • Compound (M-1a) can be produced by reacting compound (M-3) with phosphorus oxychloride or phosphorus oxybromide.
  • the reaction is usually performed in a solvent.
  • the solvent used for the reaction include aromatic hydrocarbons.
  • phosphorus oxychloride can also be used as a solvent.
  • phosphorus oxychloride or phosphorus oxybromide is usually used at a ratio of 1 to 10 mol per 1 mol of compound (M-3).
  • the reaction temperature is usually in the range of 0 ° C to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • compound (M-1a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-1b) can be produced by reacting compound (M-1a) with an inorganic fluoride or inorganic iodide.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures thereof.
  • the inorganic fluoride used in the reaction include potassium fluoride, sodium fluoride, cesium fluoride and the like.
  • Examples of the inorganic iodide used in the reaction include potassium iodide and sodium iodide.
  • an inorganic fluoride or an inorganic iodide is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M-1a).
  • the reaction temperature is usually in the range of 0 ° C to 250 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • compound (M-1b) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Reference manufacturing method 3 Compound (M-3) can be produced by dealkylating a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) in the presence of an acid.
  • M-4 a compound represented by formula (M-4)
  • R 41 represents a methyl group or an ethyl group, and other symbols represent the same meaning as described above.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include aliphatic halogenated hydrocarbons, aromatic hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • Examples of the acid used in the reaction include mineral acids such as hydrochloric acid, boron halides such as boron trichloride and boron tribromide, titanium chloride, and aluminum chloride.
  • an acid is usually used at a ratio of 0.1 to 10 mol with respect to 1 mol of the compound (M-4).
  • the mineral acid can also be used as a solvent.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound (M-7) a compound represented by the formula (M-5) (hereinafter referred to as the compound (M-5)) is used instead of the compound (M-8), and the compound described in the production method 5 is used. It can be produced according to the method for producing (M-9).
  • Compound (M-4a) can be produced according to the method for producing compound (Ia) of the present invention described in Production Method 5 using Compound (M-7) instead of Compound (M-9). it can.
  • Compound (M-4b) and Compound (M-4c) can be produced according to the method described in Production Method 1, using Compound (M-4a) instead of Compound (Ia) of the present invention.
  • compound (M-2a) a compound in which Het is Het-1 (hereinafter referred to as compound (M-2a)) is a compound in which Het is Het-1 in compound (M-3) (hereinafter, referred to as compound (M-2a)).
  • Compound (M-3a)) and a sulfurizing agent can be reacted.
  • a plurality of R 6 may be the same or different, and other symbols represent the same meaning as described above.
  • the reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers and aromatic hydrocarbons.
  • Examples of the sulfurizing agent used in the reaction include 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-disulfide and diphosphorus pentasulfide.
  • the sulfiding agent is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (M-3a).
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • compound (M-2a) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • compound (M-2b) a compound in which Het is Het-2 (hereinafter referred to as compound (M-2b)) is a compound in which Het is Het-2 in compound (M-3) (hereinafter, referred to as compound (M-2b)).
  • Compound (M-3b)) can be produced by reacting with a sulfurizing agent.
  • a plurality of R 6 may be the same or different, and other symbols represent the same meaning as described above.
  • Compound (M-2b) can be produced according to the method described in Reference Production Method 5, using compound (M-3b) in place of compound (M-3a).
  • Reference manufacturing method 7 In the compound (M-8), a compound in which m is 0 (hereinafter referred to as compound (M-8a)), a compound in which m is 1 (hereinafter referred to as compound (M-8b)), and m A compound in which is 2 (hereinafter referred to as compound (M-8c)) can be produced according to the following method.
  • X 7 represents a chlorine atom, a bromine atom, or an iodine atom, and other symbols have the same meaning as described above. However, when X 7 is a bromine atom, X 4 is a bromine atom or a chlorine atom, and when X 7 is a chlorine atom, X 4 represents a chlorine atom.
  • Compound (M-11) is produced by reacting a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with thiobenzoic acid in the presence of a copper catalyst and a base. can do.
  • Compound (M-10) is a commercially available compound or can be produced according to a known method. The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures thereof.
  • Examples of the copper catalyst used in the reaction include copper chloride, copper bromide, and copper iodide.
  • Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases such as triethylamine, diisopropylethylamine, pyridine, and 4- (dimethylamino) pyridine.
  • a ligand may be added as necessary.
  • Examples of the ligand used in the reaction include 2,2′-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, and the like.
  • thiobenzoic acid is usually used in a proportion of 1 to 10 mol
  • copper catalyst is usually used in a proportion of 0.01 to 0.5 mol, based on 1 mol of compound (M-10).
  • the ligand is usually used in a proportion of 0.01 to 1 mol
  • the base is usually used in a proportion of 0.1 to 5 mol.
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M-11) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-12) can be produced by solvolysis of compound (M-11) in the presence of a base.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction water or alcohols are used.
  • the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates, and sodium methoxide.
  • the base is generally used at a ratio of 1 to 5 mol with respect to 1 mol of the compound (M-11).
  • the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (M-12) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M-11) can also be produced, for example, according to the method described in International Publication No. 2011/068171, or the method described in Journal Organic Chemistry, 1978, 43 (6), 1190-1192. .
  • Compound (M-8a) can be produced according to the method described in Production Method 4, using Compound (M-12) in place of Compound (M-2).
  • Compound (M-8b) can be produced according to the method described in Production Method 1, using Compound (M-8a) instead of Compound (Ia) of the present invention.
  • Compound (M-8c) can be produced according to the method described in Production Method 1, using Compound (M-8b) in place of Compound (Ib) of the present invention.
  • compound (IA) m is 1, n is 2, R 3a , R 3b , and R 3c are hydrogen atoms, and R 1 and R 2 are [Table 1] to [Table 5]. Or a combination of any of the above (hereinafter referred to as compound group SX2).
  • compound (IB) In the compound represented by formula (IB) (hereinafter referred to as compound (IB)), m is 0, n is 2, and R 3a , R 3b , and R 3c are hydrogen atoms.
  • a compound in which R 1 and R 2 are any combination described in [Table 1] to [Table 5] hereinafter referred to as compound group SX7).
  • compound (IC) In the compound represented by formula (IC) (hereinafter referred to as compound (IC)), m is 0, n is 2, and R 3a , R 3b , and R 3c are hydrogen atoms.
  • IC compound represented by formula (IC)
  • m is 0, n is 2, and R 3a , R 3b , and R 3c are hydrogen atoms.
  • R 1 and R 2 are any combination described in [Table 1] to [Table 5] (hereinafter referred to as compound group SX13).
  • compound (IC) m is 2, n is 2, R 3a , R 3b , and R 3c are hydrogen atoms, and R 1 and R 2 are [Table 1] to [Table 5]. Or a combination of any of the above (hereinafter referred to as compound group SX15).
  • compound (ID) In the compound represented by formula (ID) (hereinafter referred to as compound (ID)), m is 0, n is 2, and R 3a , R 3b , and R 3c are hydrogen atoms.
  • a compound in which R 1 and R 2 are any combination described in [Table 1] to [Table 5] hereinafter referred to as compound group SX19).
  • compound (ID) m is 1, n is 2, R 3a , R 3b , and R 3c are hydrogen atoms, and R 1 and R 2 are [Table 1] to [Table 5]. Or a combination of any of the above (hereinafter referred to as compound group SX20).
  • compound (ID) m is 1, n is 2, R 3a and R 3c are hydrogen atoms, R 3b is a trifluoromethyl group, and R 1 and R 2 are [Table 1 ] To [Table 5] in any combination (hereinafter referred to as compound group SX23).
  • compound (IE) m is 1, n is 2, R 3a , R 3b , and R 3c are hydrogen atoms, and R 1 and R 2 are [Table 1] to [Table 5] Or a combination of any of the above (hereinafter referred to as compound group SX26).
  • compound (IE) m is 2, n is 2, R 3a , R 3b , and R 3c are hydrogen atoms, and R 1 and R 2 are [Table 1] to [Table 5]. Or a combination of any of the above (hereinafter referred to as compound group SX27).
  • compound (IF) In the compound represented by formula (IF) (hereinafter referred to as compound (IF)), m is 0, n is 2, and R 3a , R 3b , and R 3c are hydrogen atoms.
  • R 1 and R 2 are any combination described in [Table 1] to [Table 5] (hereinafter referred to as compound group SX31).
  • compound (IA) m is 0, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX40).
  • m is 1, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX41).
  • compound (IA) In the compound (IA), m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX46).
  • compound (IA) m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX47).
  • compound (IA) In the compound (IA), m is 2, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX48).
  • compound group SX49 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX49).
  • compound (IA) m is 1, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX50).
  • compound (IA) m is 2, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX51).
  • compound (IA) In the compound (IA), m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX55).
  • compound (IA) m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX56).
  • compound (IA) m is 2, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX57).
  • compound group SX58 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX58).
  • compound (IA) m is 1, n is 2, R 1 is a 2,2,3,4,4,4-hexafluorobutyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX59).
  • compound group SX60 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX60).
  • compound group SX62 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX62).
  • compound (IB) In the compound (IB), m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX79).
  • compound group SX80 In the compound (IB), m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX80).
  • compound (IB) In the compound (IB), m is 2, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX81).
  • compound (IB) In compound (IB), m is 0, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX82).
  • compound group SX83 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX83).
  • compound group SX84 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX84).
  • compound (IB) In the compound (IB), m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX88).
  • compound (IB) m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX89).
  • compound (IB) m is 2, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any of [Table 6] to [Table 16] (hereinafter referred to as compound group SX90).
  • compound group SX91 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX91).
  • compound group SX93 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX93).
  • m is 1, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX107).
  • compound group SX112 In the compound (IC), m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX112).
  • compound group SX113 In the compound (IC), m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX113).
  • compound group SX114 In the compound (IC), m is 2, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX114).
  • compound group SX115 In the compound (IC), m is 0, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX115).
  • compound group SX116 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX116).
  • compound group SX117 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX117).
  • compound group SX121 In the compound (IC), m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX121).
  • compound group SX122 In the compound (IC), m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX122).
  • compound group SX123 In the compound (IC), m is 2, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX123).
  • compound group SX124 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX124).
  • compound group SX125 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX125).
  • compound group SX126 A compound in which R 3a , R 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX126).
  • compound group SX127 In the compound (IC), m is 0, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX127).
  • compound group SX129 In the compound (IC), m is 2, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX129).
  • compound (ID) m is 2, n is 2, R 1 is a trifluoromethyl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c are [Tables] 6] to [Table 16] are any combination of the compounds (hereinafter referred to as compound group SX138).
  • m is 1, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX140).
  • compound (ID) m is 0, n is 2, R 1 is a perfluoroethyl group, R 2 is an ethyl group, and R 3a , R 3b , and R 3c are [Table 6 ] To [Table 16] are any combination (hereinafter referred to as compound group SX142).
  • compound (ID) m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX145).
  • compound (ID) m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX146).
  • compound (ID) m is 2
  • n is 2
  • R 1 is a 1,1,2,2-tetrafluoroethyl group
  • R 2 is an ethyl group
  • R 3a R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX147).
  • compound (ID) m is 0, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX148).
  • compound (ID) m is 1, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX149).
  • compound (ID) m is 2
  • n is 2
  • R 1 is a 1,1,2,3,3,3-hexafluoropropyl group
  • R 2 is an ethyl group
  • a compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX150).
  • compound (ID) m is 0, n is 2, R 1 is a perfluoropropyl group, R 2 is an ethyl group, and R 3a , R 3b , and R 3c are [Table 6 ] To [Compound 16] (hereinafter referred to as compound group SX151).
  • compound (ID) In the compound (ID), m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX154).
  • compound (ID) m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any of [Table 6] to [Table 16] (hereinafter referred to as compound group SX155).
  • compound (ID) m is 2
  • n is 2
  • R 1 is a perfluoropropan-2-yl group
  • R 2 is an ethyl group
  • R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX156).
  • compound (ID) m is 0, n is 2, R 1 is a 2,2,3,4,4,4-hexafluorobutyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX157).
  • compound (ID) m is 1, n is 2, R 1 is a 2,2,3,4,4,4-hexafluorobutyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX158).
  • compound (ID) m is 2
  • n is 2
  • R 1 is a 2,2,3,4,4,4-hexafluorobutyl group
  • R 2 is an ethyl group
  • a compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX159).
  • compound group SX160 In the compound (ID), m is 0, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX160).
  • compound group SX161 In the compound (ID), m is 1, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX161).
  • compound group SX162 In the compound (ID), m is 2, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX162).
  • m is 0, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX172).
  • m is 1, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX173).
  • compound group SX178 In the compound (IE), m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX178).
  • compound group SX179 In the compound (IE), m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX179).
  • compound group SX180 In the compound (IE), m is 2, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX180).
  • compound (IE) In compound (IE), m is 0, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX181).
  • compound (IE) m is 1, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX182).
  • compound (IE) m is 2, n is 2, R 1 is a 1,1,2,3,3,3-hexafluoropropyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX183).
  • compound (IE) m is 2, n is 2, R 1 is a perfluoropropyl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c are [Table 6 ] To [Table 16] are any combination of the compounds (hereinafter referred to as compound group SX186).
  • compound (IE) m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX187).
  • compound (IE) m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX188).
  • compound (IE) In compound (IE), m is 0, n is 2, R 1 is a 2,2,3,4,4,4-hexafluorobutyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX190).
  • compound (IE) m is 1, n is 2, R 1 is a 2,2,3,4,4,4-hexafluorobutyl group, R 2 is an ethyl group, A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX191).
  • compound group SX192 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX192).
  • R 1 is a 2,2,3,3,4,4,4-heptafluorobutyl group
  • R 2 is an ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX193).
  • m is 1, n is 2, R 1 is 2,2,3,3,4,4,4-heptafluorobutyl group, R 2 is ethyl group A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX194).
  • m is 1, n is 2, R 1 is a 2,2,2-trifluoroethyl group, R 2 is an ethyl group, R 3a , R 3b , And R 3c is any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX206).
  • compound group SX211 In the compound (IF), m is 0, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX211).
  • compound group SX212 In the compound (IF), m is 1, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX212).
  • compound group SX213 In the compound (IF), m is 2, n is 2, R 1 is a 1,1,2,2-tetrafluoroethyl group, R 2 is an ethyl group, R 3a , R A compound in which 3b and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX213).
  • compound group SX214 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX214).
  • compound group SX216 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX216).
  • compound group SX220 In the compound (IF), m is 0, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX220).
  • compound group SX221 In the compound (IF), m is 1, n is 2, R 1 is a perfluoropropan-2-yl group, R 2 is an ethyl group, R 3a , R 3b , and R 3c Is a combination of any one of [Table 6] to [Table 16] (hereinafter referred to as compound group SX221).
  • compound group SX224 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX224).
  • compound group SX225 A compound in which R 3a , R 3b , and R 3c are any combination described in [Table 6] to [Table 16] (hereinafter referred to as compound group SX225).
  • the compound of the present invention is mixed with one or more components selected from the group consisting of the following group (a), group (b), group (c), group (d) and group (e) (hereinafter referred to as this component). Or it can use together.
  • the mixed use or combination means that the compound of the present invention and the present component are used simultaneously, separately or at intervals.
  • this invention compound and this component may be contained in the respectively separate formulation, and may be contained in one formulation.
  • One aspect of the present invention is one or more components selected from the group consisting of group (a), group (b), group (c), and group (d) and group (e) (ie, the present component), And a composition containing the compound of the present invention.
  • Group (a) is a group of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients, comprising the following subgroups a-1 to a-10.
  • Subgroup a-1 Carbamate acetylcholinesterase (AChE) inhibitor
  • Subgroup a-2 Organophosphorus acetylcholinesterase (AChE) inhibitor
  • Subgroup a-3 GABAergic chloride channel blocker subgroup a-4: GABAergic chloride channel allosteric modulator subgroup a-5: sodium channel modulator subgroup a-6: nicotinic acetylcholine receptor (nAChR) competitive modulator subgroup a-7: ryanodine receptor modulator subgroup a-8: Microbial material subgroup a-9: nematicidal active ingredient subgroup a-10: other insecticidal active ingredient / acaricidal active ingredient
  • Group (b) is a group of bactericidal active ingredients consisting of the following subgroups b-1 to b-18.
  • Subgroup b-1 PA fungicide (phenylamide)
  • Subgroup b-2 MBC fungicide (methylbenzimidazole carbamate)
  • Subgroup b-3 Thiazolecarboxamide subgroup b-4: SDHI (succinate dehydrogenase inhibitor)
  • Subgroup b-5 QoI fungicide (Qo inhibitor)
  • Subgroup b-6 QiI fungicide (Qi inhibitor)
  • Subgroup b-7 Thiophenecarboxamide subgroup b-8: AP fungicide (anilinopyrimidine)
  • Subgroup b-9 PP fungicide (phenylpyrrole)
  • Subgroup b-10 AH fungicide (aromatic hydrocarbon)
  • Subgroup b-11 DMI-bactericides (demethylation inhibitors)
  • Subgroup b-12 CCA fungicide (carboxylic amide)
  • Group (c) is a group of plant growth regulating components consisting of the following subgroup c-1, subgroup c-2 and subgroup c-3.
  • Subgroup c-1 Plant growth regulating component
  • Subgroup c-2 Mycorrhizal subgroup c-3: Rhizobium
  • Group (d) is a group of chemical damage reducing components.
  • Group (e) is a group of synergists.
  • the composition containing the present component and the present compound exhibits the effect of the composition depending on the content or content of the present component or the present compound in the composition. Therefore, the use of the composition can be determined according to the effect expressed by the composition.
  • the composition may have one or more uses.
  • One aspect of the composition is an agrochemical composition.
  • Another aspect of the composition is a harmful arthropod control composition.
  • Another aspect of the composition is an insecticidal, acaricidal or nematicidal composition.
  • Another aspect of the composition is a bactericidal composition.
  • Another aspect of the composition is a plant growth regulating composition.
  • Yet another aspect of the composition is a safener composition.
  • alanycarb + SX means a combination of alanicarb and SX.
  • the abbreviation SX means any one compound of the present invention selected from the compound groups SX1 to SX234.
  • all of the components described below are known components, and can be obtained from commercially available preparations or produced by known methods. If this component is a microorganism, it can also be obtained from a fungus depository.
  • the numbers in parentheses represent CAS registration numbers.
  • Agrobacterium radiobactor (Strain 84, etc.) + SX, Bacillus amyloliquefaciens + SX, Bacillus amyloliquefaciens QST713 strain + SX, Bacillus amyloliquefaciens FZB24 + SX, Bacillus amyloliquefaciens MBI600 + SX, Bacillus amyloliquefaciens D747 + SX, Bacillus amyloliquefaciens AT332 + SX, Bacillus amyloliquefaciens PTA4838 + SX, Bacillus ⁇ Bacillus pumilus + SX, Bacillus simplex (Bacillus simplex, CGF2856, etc.) + SX, Bacillus subtilis + SX, Bacillus subtilis QST713 + SX, Bacillus subtilis HAI0404 + SX, Bacillus ⁇ Sub
  • harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites. Specific examples of such harmful arthropods include the following.
  • Hemiptera Japanese brown planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted plant (Javesella pellucella), colofinosi (Delphacidae); Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalisoa, Emp ), Corn Leaf Hopper (Dalbulus maidis), White Leafhopper (Cofana spectra), etc.
  • Adelgidae Scotinophara lurida, Malayan rice black bug (Scotinophara coarctata), Nezara antennata, Eysarcoris aeneus, ysoris , White stink bugs (Eysarcoris ventralis), spotted stink bugs (Eysarcoris annamita), blue stink bugs (Halyomorpha halys), southern stink bugs (Nezara viridula), Brown stink bug (Euschistus bands) , Dichelops melacanthus, etc. (Pentatomidae); Burrower brown bug (Scaptocoris castanea), etc.
  • Alydidae such as Cletus punctiger, Leptoglossus australis, Coreidae, Caverelius saccharyorus hemipterus) Lygaeidae (Blissus leucopterus) and other species (Lygaeidae); Trigonotylus caelestialium, Stenotus vitrubrovittatus, Luna calculus (Stenode) Miridae; Onitsuna lice (Trialeurodes vaporariorum), Tobacco whiteflies (Bemisia tabaci), Citrus whitefly (Dialeurodes citri), Citrus elegans (Aleurocanthus spiniferus), Chalge eleanthus ), Etc .; Aleyrodidae; Abgrallaspis cyanophylli, Aonidiella aurantii, Daspidiotus perniciosus, Scots Diaspididae such as Pseudaulacaspis pentag
  • Cicada such as Giant Cicada (Quesada gigas).
  • Lepidoptera Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itteno eel moth (Scirpophaga incertulas), Rupela albina medina, Hacasino maiga (Marasmia exigua), cotton moth (Notarcha derogata), yellow corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), yellow moth (Hellula undalis), monk black moth terrel Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc.
  • Thysanoptera Citrus thrips (Frankliniella occidentalis), Thrips palmiet (Sriptos etbisiton) ), Thripidae such as Echinothrips americanus; Phthaothripripae such as Haplothrips aculeatus.
  • Diptera Drosophila (Delia platura), onion flies (Delia antiqua), etc., Anthomyiidae; Tomato leafhopper (Liriomyza sativae), bean leafworm (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafworms (Agromyzidae); ), Eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quinzland fruit fly (Bactrocera tryoni), CeratitisCcapitata, etc.
  • Coleoptera Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cue Diabrotica balteata), Cucurbit tle Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Bark beetle (Oulema melanopus), potato beetle (Aulacophora femoralis), Phyllotreta bb Cabe black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Inedro beetle (Oulema oryzae), Grape colaspi
  • Carabidae Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), Black marsh (Tomarus gibbosus), Holotrichiall Haga crinita) and other genus Phyllophaga genus (Phyllophaga spp.), Diloboderus usabderus genus Diloboderus genus (Diloboderus spp.) and other scarab beetles (Scarabaeidae); Eusces Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus S subsignatus), Sugarcane weevil (Sphenophorus levis), Sabihyo weevil (Scepticus griseus) mis), Brazilian weevil (Zabrotes subfasciat
  • Tribolium castaneum, Tribolium confusum, etc . Tribolium castaneum, Tribolium confusum, etc .; Tenebrionidae; Epilachna vigintioctopunctata, etc .; Bostrychidae; Leopardidae (Ptinidae); Anoplophora malasiaca, Migdolus fryanus, etc. , Melanotus legatus, Anchastus spp., Connoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., Etc. Elateridae; Staphylinidae such as Paederus fuscipes.
  • Orthoptera Tosama locust (Locusta migratoria),ixie flying grasshopper (Dociostaurus maroccanus), Australian flying grasshopper (Chortoicetes terminifera), Red-spotted grasshopper (Nomadacris septemfasciata), Brown Locust ina Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoula femurrubrum) gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Red-tailed hawk (Oxya japonica), Grasshopper Locust (Patanga succincta), etc. ridi
  • Hymenoptera bee (Athalia rosae), Japanese bee (Athalia japonica) and other bees (Tenthredinidae); fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta Department (Formicidae) etc.
  • Cockroaches (Blattodea): German cockroaches (Blattellidae) such as the German cockroach (Blattella germanica); Family (Blattidae); Yamato termite (Reticulitermes speratus), Japanese termite (Coptotermes formosanus), American ant termite (Incisitermes orminor), Great white termite (Cryptotermes domesticus), Thai one termite (Odontotermes ⁇ ant hunter) (Glyptotermes satsumensis), Nakajima Termites (Glyptotermes nakajimai), Caterpillars (Glyptotermes fuscus), Termites (Hodotermopsis sjostedti), Coptotermes guangzhouen sis), Amite Termites (Reticulitermes amamianus), Miyatake Termites (Reticulitermes miyatakei), Camellia Termites (Reticuli
  • Tick spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Mite spider mite (Tetranychus evansi), Citrus spider mite (Panonychus citri), Apple spider mite (Panonychus ⁇ ulmi), Ony chus ⁇ s Tetranychidae); citrus mite (Aculops pelekassi), Ryukyu mandarin mite (Phyllocoptruta citri), tomato rustic mite (Aculops lycopersici), green rustic mite (Calacarus carinatus), green moth mite (Acaphylla ⁇ sei sei seisei) (Aculus pointedendali), oyster mite (Aceria diospyri), Aceria tosichella, terrestrial mite (Shevtchenkella sp.), Etc.
  • Eriophyidae Eriophyidae
  • Mite Tenuipalpidae such as ticks (Brevipalpus phoenicis); Tuckerellidae (Tuckerellidae); Ixodes ovatus, Ixodes ⁇ persulcatus, Black-legged ticks (Ixodescapscapularis), American tick ticks (Amblyomma americanum), Oticid ticks (Boophilus microplus), Tick ticks (Rhipicephalus sanguineus), etc.
  • Acaridae such as Tyrophagus putrescentiae and Tyrophagus similis; Dermatophagoides farinae, Dermatophagoides pteronyssinus and other mites (Pyroglyphidae); clawlet mite (Cheyletus eruditus), stag beetle mite (Cheyletus malaccensis), horn mite (Cheyletus moorei), crayfish tick (Cheyletiella yasguri), etc.
  • Scaroptidae Scaroptidae
  • Scaroptidae (Demodex canis); Demodexidae; Listrophoridae; Haplochthoniidae; Macronyssidae); Dermanyssidae such as Dermanyssusaegallinae; Dermanyssidae; Trombiculidae such as Leptotrombidium akamushi.
  • the harmful arthropod control agent of the present invention contains the compound of the present invention and an inert carrier.
  • the harmful arthropod control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and if necessary, a surfactant and other adjuvants for formulation.
  • the harmful arthropod control agent of the present invention can be mixed with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists.
  • the harmful arthropod control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur).
  • Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), n
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • fixing agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (is
  • the base material of the resin preparation examples include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base material using an ordinary kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc. It can be processed into resin preparations such as plate, film, tape, net, and string. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
  • bait base examples include cereal flour, vegetable oil, sugar, crystalline cellulose, and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid.
  • antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid
  • preservatives such as dehydroacetic acid.
  • Additives for preventing accidental eating by children and pets such as pepper powder, cheese flavor, onion flavor, peanut oil and other pest-attracting flavors are added.
  • an effective amount of the compound of the present invention is applied directly to harmful arthropods and / or to pest habitats (plants, soil, households, animal bodies, etc.). Is done.
  • the harmful arthropod control method of the present invention is usually used in the form of the harmful arthropod control agent of the present invention.
  • the application amount is usually 1 to 10000 g as the amount of the compound of the present invention per 10,000 m 2 .
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually applied by diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.
  • These preparations and water dilutions of these preparations may be sprayed directly onto harmful arthropods or plants such as crops to be protected from harmful arthropods, and also control pests that inhabit cultivated soil Therefore, the soil may be treated.
  • it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
  • the amount applied is the amount of the compound of the present invention per 1 m 2 of the treated area when treated on the surface, and is usually 0.
  • the amount of the compound of the present invention per 1 m 3 of the treatment space is usually 0.01 to 500 mg.
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. Apply oils, aerosols, smoke, poison baits, etc. as they are.
  • the harmful arthropod control agent of the present invention When used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals.
  • systemic suppression for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag.
  • the amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
  • Production Example 2 The compounds produced according to Production Example 1 (6) and their physical properties are shown below.
  • Formula (100) In which R 100 , A 7 , and R 103 are represented by [Table 15].
  • Production Example 4 The compounds produced according to Production Example 3 and their physical properties are shown below.
  • Formula (100) In which R 100 , A 7 , and R 103 are represented by [Table 16].
  • Production Example 8 A mixture of 300 mg of intermediate (5), 440 mg of potassium carbonate and 5 mL of NMP was stirred at room temperature for 10 hours under hexafluoropropene atmosphere. A saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the obtained residue was diluted with 7.0 mL of ethanol, and 1.6 mL of 28% aqueous ammonia solution was added at room temperature.
  • the mixture was heated and stirred at 60 ° C. for 2.5 hours, allowed to cool to room temperature, added to saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate.
  • the obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
  • the obtained residue was subjected to silica gel chromatography to obtain 1.3 g of intermediate (8) represented by the following formula.
  • Production Example 10 (1) A mixture of 10 g of methyl 5-chloro-2-pyrazinecarboxylate, 28 mL of sodium methoxide (28% methanol solution), and 100 mL of THF was stirred for 3 hours under ice cooling. To the resulting reaction mixture, 18 mL of ethyl methyl sulfone was added under ice cooling. The reaction mixture was heated to 80 ° C. and stirred for 24 hours. The resulting reaction mixture was allowed to cool to room temperature, 2N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated.
  • Production Example 11 (2) The present compound S-17 can be produced according to the method described in Production Example 1 (6) using the intermediate (13) instead of the intermediate (5).
  • Production Example 12 (2) Compound S-18 can be produced according to the method described in Production Example 1 (6) using Intermediate (14) instead of Intermediate (5).
  • Production Example 13 The compounds that can be produced according to Production Example 11 (1) and Production Example 12 (2) are shown below.
  • Formula (300) is shown below.
  • Production Example 15 The compounds that can be produced according to Production Example 14 are shown below.
  • a part represents a weight part.
  • Formulation Example 1 10 parts of any one of compounds S-1 to S-44 are mixed with a mixture of 35 parts of xylene and 35 parts of DMF, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto. , Mix to obtain each formulation.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and 20 parts of any one of compounds S-1 to S-44 are added and mixed. To obtain each wettable powder.
  • Formulation Example 4 One part of any one of compounds S-1 to S-44 is mixed with an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of isopropyl acid phosphate and 93.7 parts of kaolin clay are mixed therewith. Are added to the mixture with sufficient stirring, and acetone is removed by evaporation to obtain each powder.
  • Formulation Example 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of compounds S-1 to S-44, and 55 parts of water are mixed and wet. Each flowable agent is obtained by pulverizing by a pulverization method.
  • Formulation Example 6 0.1 part of any one of compounds S-1 to S-44 is mixed with a mixture of 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of kerosene to obtain each oil.
  • Formulation Example 7 10 mg of any one of compounds S-1 to S-44 is mixed with 0.5 ml of acetone, and this solution is mixed with 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.). Add to the mixture and mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder termed breeding solid feed powder CE-2, Nippon Claire Co., Ltd.
  • Formulation Example 8 0.1 part of any one of compounds S-1 to S-44, 49.9 parts of neothiozole (manufactured by Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are added. Fill and shake, and attach an actuator to obtain an oil aerosol.
  • Formulation Example 9 0.6 part of any one of compounds S-1 to S-44, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts of kerosene and Emulsifier ⁇ Rheodor MO-60 (manufactured by Kao Corporation) ⁇ 1 part and 50 parts of distilled water are filled in an aerosol container, and after attaching a valve, 40 parts of propellant (LPG) is added through the valve. Pressurize to obtain an aqueous aerosol.
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • xylene 3.39 parts of kerosene and Emulsifier ⁇ Rheodor MO-60 (manufactured by Kao Corporation) ⁇ 1 part and 50 parts of distilled water
  • LPG propellant
  • Formulation Example 10 0.1 g of any one of compounds S-1 to S-44 is mixed with 2 ml of propylene glycol, impregnated into a ceramic plate of 4.0 ⁇ 4.0 cm and thickness of 1.2 cm, and heated smoking Get the agent.
  • Formulation Example 11 5 parts of any one of compounds S-1 to S-44 and ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT (registered trademark) WD301, manufactured by Sumitomo Chemical Co., Ltd.) ) 95 parts are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • ACRIFT registered trademark
  • WD301 manufactured by Sumitomo Chemical Co., Ltd.
  • Formulation Example 12 5 parts of any one of compounds S-1 to S-44 and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is molded from an extrusion molding machine into a molding die. Is extruded to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • Formulation Example 13 Any one of compounds S-1 to S-44 100 mg, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg, and stearin Mix 2.5 mg of magnesium acid and compress the resulting mixture to an appropriate size to obtain tablets.
  • Formulation Example 14 Any one of compounds S-1 to S-44 25 mg, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is mixed with a hard shell gelatin capsule or hydroxypropyl Fill into methylcellulose capsules to obtain capsules.
  • Formulation Example 15 Any one of compounds S-1 to S-44 100 mg, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, Veegum K (Vanderbilt Co.) 100 mg Then, distilled water is added to and mixed with 35 mg of the fragrance and 500 mg of the colorant so as to have a final volume of 100 ml to obtain a suspension for oral administration.
  • distilled water is added to and mixed with 35 mg of the fragrance and 500 mg of the colorant so as to have a final volume of 100 ml to obtain a suspension for oral administration.
  • Formulation Example 16 5% by weight of any one of compounds S-1 to S-44 is mixed with 5% by weight of an emulsifier, 3% by weight of benzyl alcohol, and 30% by weight of propylene glycol, and the pH of this solution is 6.0 to 6. After adding a phosphate buffer so that it may be 5, water is added as a remainder and the liquid for oral administration is obtained.
  • Formulation Example 17 5% by weight of aluminum distearate in 57% by weight of fractionated coconut oil and 3% by weight of polysorbate 85 is added and dispersed by heating. This is cooled to room temperature and 25% by weight of saccharin is dispersed in the oily vehicle. To this, 10% by weight of any one of compounds S-1 to S-44 is allocated to obtain a paste preparation for oral administration.
  • Formulation Example 18 5% by weight of any one of compounds S-1 to S-44 is mixed with 95% by weight of limestone powder, and granules for oral administration are obtained using the wet granulation method.
  • Formulation Example 19 5 parts of any one of compounds S-1 to S-44 are mixed with 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate are mixed with this to obtain a spot-on liquid agent.
  • Formulation Example 20 10 parts of any one of compounds S-1 to S-44 are mixed with 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed with this to obtain a pour-on solution.
  • Formulation Example 22 0.15% by weight of any one of compounds S-1 to S-44, 95% by weight of animal feed, and 4.85% by weight of a mixture composed of dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) Mix well and obtain animal feed premix.
  • Formulation Example 23 7.2 g of any one of compounds S-1 to S-44 and 92.8 g of Fosco (registered trademark) S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) were mixed at 100 ° C. Cool to solidify to obtain a suppository.
  • Fosco registered trademark
  • test examples the efficacy of the compound of the present invention against harmful arthropods is shown by test examples.
  • the test was performed to prevent insect escape and the temperature was 25 ° C.
  • Test example 1 A test compound is prepared according to the method described in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing the test compound at a predetermined concentration. About 30 cotton aphids (all stages) are inoculated on Cucumber sativas seedlings (second true leaf development stage) planted in a container. After 1 day, the diluted solution is sprayed on the seedlings at a rate of 10 mL / seedling. After 5 days, the number of live insects is examined, and the control value is obtained by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai Number of live insects at the time of survey in the treated group It means a group that operates in the same manner as the treatment group except that the test compound is not used.
  • Cb Number of test insects in the untreated group
  • Cai Number of live insects at the time of survey in the untreated group
  • Tb Number of test insects in the treated group
  • Tai Number of live insects at the time of survey in the treated group It means a group that operates in the same manner as the treatment group except that the test compound is not used.
  • the compound of the present invention exhibits an excellent control effect against harmful arthropods.

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Abstract

La présente invention décrit un composé, représenté par la formule (1) [où A1 représente un atome d'azote ou CR4, R4 représentant un atome d'hydrogène ou similaire, n'importe lequel de A2, A3, et A4 représente un atome d'azote et le reste représente CR6, R6 représentant un atome d'hydrogène ou similaire et une pluralité de R6 étant identiques ou différents, R1 représente un groupe hydrocarboné à chaîne ouverte en C1 à C10 ou similaire ayant un atome d'halogène ou plus, R2 représente un groupe alkyle en C1 à C6 ou similaire qui peuvent avoir un ou plusieurs atomes d'halogène, q représente 0, 1, 2, ou 3, R3 représente un groupe hydrocarboné à chaîne ouverte en C1 à C6 ou similaire qui peuvent avoir un ou plusieurs substituants sélectionnés dans le groupe B, et une pluralité de R3 peuvent être identiques ou différents lorsque q à la valeur de 2 ou 3], ou son composé N oxyde présente un excellent effet d'extermination d'un arthropode nuisible.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2018221720A1 (ja) * 2017-06-01 2020-04-16 住友化学株式会社 複素環化合物及びそれを含有する組成物
WO2024080354A1 (fr) 2022-10-14 2024-04-18 住友化学株式会社 Composé de sulfonamide et composition de lutte contre les arthropodes nuisibles le contenant
WO2024189139A1 (fr) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Lutte contre des nuisibles résistants aux insecticides

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Publication number Priority date Publication date Assignee Title
JP2000026421A (ja) * 1998-01-29 2000-01-25 Kumiai Chem Ind Co Ltd ジアリ―ルスルフィド誘導体及び有害生物防除剤
JP2004524310A (ja) * 2001-02-22 2004-08-12 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 有害生物防除剤としての使用のためのピリジルピリミジン類
WO2016030229A1 (fr) * 2014-08-25 2016-03-03 Syngenta Participations Ag Dérivés hétérocycliques à action pesticide comportant des substituants contenant du soufre
WO2016121970A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour lutter contre les arthropodes nuisibles

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000026421A (ja) * 1998-01-29 2000-01-25 Kumiai Chem Ind Co Ltd ジアリ―ルスルフィド誘導体及び有害生物防除剤
JP2004524310A (ja) * 2001-02-22 2004-08-12 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 有害生物防除剤としての使用のためのピリジルピリミジン類
WO2016030229A1 (fr) * 2014-08-25 2016-03-03 Syngenta Participations Ag Dérivés hétérocycliques à action pesticide comportant des substituants contenant du soufre
WO2016121970A1 (fr) * 2015-01-30 2016-08-04 住友化学株式会社 Composé bipyridine et son utilisation pour lutter contre les arthropodes nuisibles

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2018221720A1 (ja) * 2017-06-01 2020-04-16 住友化学株式会社 複素環化合物及びそれを含有する組成物
JP7269876B2 (ja) 2017-06-01 2023-05-09 住友化学株式会社 複素環化合物及びそれを含有する組成物
WO2024080354A1 (fr) 2022-10-14 2024-04-18 住友化学株式会社 Composé de sulfonamide et composition de lutte contre les arthropodes nuisibles le contenant
WO2024189139A1 (fr) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Lutte contre des nuisibles résistants aux insecticides

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