Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/04—Ortho-condensed systems
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
• • 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
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides

Definitions

• the present invention relates to pyrazole compounds, salts thereof, and arthropod pest control agents characterized by containing the compounds as active ingredients.
• Pest control plays an extremely important role in providing a stable and sustainable supply of agricultural and horticultural crops.
• a wide variety of pest control agents have been developed and put into practical use.
• many insect pests have acquired drug resistance. Therefore, damage in crop production such as agriculture and horticulture is still a serious issue, and there is a desire to develop new agents that are effective against not only susceptible but also resistant pests.
• pyrazole compounds having a substituent at the 3rd or 5th position of the pyrazole ring are known.
• azolopyrimidyl pyrazole compounds such as imidazo[1,2-c]pyrimidine ring and [1,2,4]triazolo[1,5-c]pyrimidine ring
• imidazo[1,2-c]pyrimidine ring and [1,2,4]triazolo[1,5-c]pyrimidine ring have adenosine A2A receptor antagonistic activity.
• azolopyrimidyl pyrazole compounds are disclosed in which the 5-position of the pyrazole ring is unsubstituted (for example, see Patent Document 1) or has an alkyl substituent (for example, see Patent Document 2).
• the substituent at the 5-position of the pyrazole is limited to an alkyl group such as a methyl group, and the azolopyrimidyl pyrazole compound has a substituted amino group or a substituted amide group. No compounds are disclosed. Further, the use of the compound group is related to the medical field, and is different from the technical field belonging to the pest control agent or harmful arthropod control agent according to the present invention.
• An object of the present invention is to provide a compound having an excellent control effect against pests, especially harmful arthropods, mainly in the agricultural field, and intermediates useful for the production thereof.
• the present inventors focused on azolopyrimidyl pyrazole compounds and, as a result of intensive studies, found that a substituted amino group, a substituted amide group, etc. at the 3-position or 5-position of the pyrazole ring, etc.
• the present inventors have discovered that a novel azolopyrimidyl pyrazole compound group into which is introduced exhibits an excellent control effect against harmful arthropods, and has completed the present invention.
• the present invention includes the following aspects.
• Rx1 and Rx2 together with the bonding nitrogen atom represents a group that forms an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group).
• Rx3OC( O)-(where Rx3 has the same meaning as above);
• R1 is hydrogen atom, C1 to C6 alkyl group which may be optionally substituted with substituent A, or represents a C1 to C6 haloalkyl group
• Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent A, C1 to C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, substituent A A C2 to C6 alkynyl group
• Rx1 and Rx2 together with the bonding nitrogen atom represents a group that forms an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, dioxothiomorpholinyl group, thiazolidinyl group, azepanyl group, or azocanyl group).
• R1 is C1 to C6 alkyl group which may be optionally substituted with substituent A, or represents a C1 to C6 haloalkyl group
• R2 is C1 to C6 alkyl group which may be optionally substituted with substituent A, C1 to C6 haloalkyl group, or represents a C3 to C8 cycloalkyl group which may be optionally substituted with substituent B
• R1 represents a pyrimidin-5-ylmethyl group or a 2,2,2-trifluoroethyl group.
• R2 represents a methyl group, an ethyl group, a propyl group, a pyrimidin-5-ylmethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, [1] to [4], and [5]; A compound or a salt thereof according to any one of the above.
• R3 represents a hydrogen atom, a methyl group, a 2,2,2-trifluoroethyl group, an acetyl group, a cyclohexylcarbonyl group, or a 4-trifluoromethoxybenzoyl group, [1] to [4], [5], and the compound or salt thereof according to any one of [6].
• R4 is a hydrogen atom, methyl group, methylcarbamoyl group, dimethylcarbamoyl group, acetyl group, propionyl group, isopropionyl group, butyryl group, isobutyryl group, pentanoyl group, 3-methyl-1-butyryl group, 3-ethyl-1 -Pentanoyl group, (1H-pyrazol-1-yl)acetyl group, (1H-1,2,4-triazol-1-yl)acetyl group, cyclopropylmethylcarbonyl group, 2-chloroacetyl group, 2,2- Difluoroacetyl group, 2,2-dichloroacetyl group, 2,2,2-trifluoroacetyl group, 2-chloro-2,2-difluoroacetyl group, 2,2-dichloro-2-fluoroacetyl group, 2,2 , 2-trichloroacetyl group, 3,3-difluor
• R7 represents a hydrogen atom, a hydroxyl group, a chlorine atom, a methyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a propyloxy group, a 2,2,2-trifluoroethoxy group, a methylsulfanyl group, or a methylsulfonyl group, The compound or salt thereof according to any one of [1] to [4] and [5] to [10].
• R8 represents a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a chlorodifluoromethyl group, a pentafluoroethyl group, a 2-fluoroisopropyl group, or a heptafluoropropyl group, [1] to [4], [ 5] to [11] or a salt thereof. [13] The compound or a salt thereof according to any one of [1] to [4] and [5] to [12], wherein R9 represents a hydrogen atom. [14] A pest control agent containing the compound or salt thereof according to any one of [1] to [4] and [5] to [13] as an active ingredient.
• the use according to [18], wherein the pest is a harmful arthropod.
• Cx to Cy represents having x to y carbon atoms.
• x and y represent integers, and it is understood that all integers between x and y are also individually disclosed.
• C1-C6 have 1, 2, 3, 4, 5, or 6 carbon atoms
• C2-C6 has 2, 3, 4, 5, or 6 carbon atoms
• C3-C8 3, 4, 5, 6, 7, or 8 carbon atoms
• C3-C6 means having 3, 4, 5, or 6 carbon atoms, respectively.
• halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.
• the C1 to C6 alkyl group may be linear or branched, and includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, isopentyl group.
• the C1-C6 haloalkyl group represents a C1-C6 alkyl group in which the hydrogen atom is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent.
• Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, dichloromethyl group, trichloromethyl group, monobromomethyl group, dibromomethyl group, monoiodomethyl group.
• diiodomethyl group diiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2 , 2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,2,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2,2-trichloroethyl group, 2 -Chloro-1,1,2,2-tetrafluoroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, 3,3,3-trichloropropyl group 2,3,3, 3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group
• Examples of the C3 to C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
• the C2 to C6 alkenyl group represents an unsaturated hydrocarbon group that has one or more double bonds and is linear or branched. In addition, if there is a geometric isomer, it may be only one of the E form or the Z form, or a mixture of the E form and the Z form at any ratio, and there are no particular limitations as long as the number of carbon atoms is within the specified range. It never happens.
• Specific examples of C2 to C6 alkenyl groups include vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methylallyl group, 1-pentenyl group, 2-pentenyl group.
• the C2-C6 haloalkenyl group represents a C2-C6 alkenyl group in which the hydrogen atom in the above C2-C6 alkenyl group is optionally substituted with one or more halogen atoms.
• these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent.
• C2 to C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 2, 3,3-trifluoroallyl group, 3,3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group, etc. can be mentioned.
• the C2 to C6 alkynyl group refers to an unsaturated hydrocarbon group that has one or more triple bonds and is linear or branched.
• Specific examples of C2 to C6 alkynyl groups include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group.
• the C2-C6 haloalkynyl group represents a C2-C6 alkynyl group in which the hydrogen atom is optionally substituted with one or more halogen atoms.
• these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent.
• C2 to C6 haloalkynyl groups include 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -difluoro-1-butynyl group, 4-bromo-4,4 -
• the C1-C6 alkoxy group represents a group in which the above-mentioned C1-C6 alkyl groups are bonded via an oxygen atom.
• Specific examples of C1 to C6 alkoxy groups include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group, pentyloxy group, and isopentyloxy group.
• the C1-C6 haloalkoxy group represents a C1-C6 alkoxy group in which the hydrogen atom is optionally substituted with one or more halogen atoms.
• these halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can exist as a substituent.
• C1 to C6 haloalkoxy groups include difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 2,2,2 -trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3 -difluoropropyloxy group, 3,3,3-trifluoropropyloxy group, 2,3,3,3-tetrafluoropropyloxy group, 2,2,3,3,3-pentafluoropropyloxy group, 1, 2,2,3,3,3-hexafluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-tri
• the C3-C8 cycloalkoxy group represents a group in which the above-mentioned C3-C8 cycloalkyl groups are bonded via an oxygen atom.
• Specific examples of the C3 to C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like.
• the 5- to 6-membered aromatic heterocyclic group represents a cyclic aromatic substituent selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms, and containing at least one hetero atom as a ring constituent atom.
• Specific examples of the 5- to 6-membered aromatic heterocyclic group include pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, furyl group, pyrrolyl group, Examples include imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, and tetrazolyl group.
• 3- to 6-membered ring groups containing 1 to 2 oxygen atoms include oxiranyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3-dioxanyl group, 1,4 -dioxanyl group, dihydrofuran-2(3H)-one group, tetrahydro-2H-pyran-2-one group, and the like.
• the pyrazole compound of the present invention includes a compound represented by the following formula (1-1) or formula (1-2) and a salt thereof.
• R1 in formula (1-1) is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C6 which may be optionally substituted with a substituent B.
• Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, a substituent A C3 to C8 cycloalkyl group optionally substituted with B, a C2 to C6 alkenyl group optionally substituted with substituent A, a C2 to C6
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group that may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 that may be optionally substituted
• R1 in formula (1-1) contains a hydrogen atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R1 of formula (1-1) has the same meaning as the above definition, and is preferably a methyl group, Ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, or hexyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group.
• the "C1 to C6 alkyl group optionally substituted with substituent A” is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, or hexyl group.
• cyanomethyl group 1-cyanoethyl group, 2-cyanoethyl group, 3-cyanopropyl group, 2-cyanopropan-2-yl group, cyclopropylmethyl group, cyclobutylmethyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group group, ethoxyethyl group, isopropyloxymethyl group, isopropyloxyethyl group, Benzyl group, 1-phenethyl group, 2-phenethyl group, 4-cyanophenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenyl group Methyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphen
• C1 to C6 haloalkyl group in R1 of formula (1-1) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2 , 2-trifluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 2,2,3,3,3-pentafluoropropyl group , 1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, or 2,2,3,3,4, 4,5,5,5-nonafluoropentyl group, more preferably difluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, or 1,1,2,2,3,3,3-heptafluoropropyl group
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R1 of formula (1-1) has the same meaning as the above definition, and is preferably cyclo It is a propyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent B When the substituent B is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with the substituent B.
• the "C3 to C8 cycloalkyl group optionally substituted with substituent B" is preferably a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-(cyclopropane-1-carbonitrile) group, 2 -(cyclopropane-1-carbonitrile) group, 1-(1-nitrocyclopropyl) group, 1-(2-nitrocyclopropyl) group, 1-(1-cyclopropylcyclopropyl) group, 1-(2 -cyclopropylcyclopropyl) group, 1-(2-methoxycyclopropyl) group, 1-(2-ethoxycyclopropyl) group, 1-(1-phenylcyclopropyl) group, 1-(2-phenylcyclopropyl) group group, 1-(cyclopropylethane-1-one) group, 2-(cyclopropylethane-1-one) group, 1-(1-methoxycarbonylcycloprop
• the C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent A" in R1 of formula (1-1) has the same meaning as the above definition, and is preferably a vinyl group, 1-propenyl group, allyl group, 2-methylallyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group, allyl group, 2-methylallyl group , or 3-butenyl group, particularly preferably allyl group, 2-methylallyl group, or 3-butenyl group.
• a substituent described in Substituent A is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent described in Substituent A.
• C2-C6 haloalkenyl group in R1 of formula (1-1) has the same meaning as the above definition, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 3-fluoroallyl group. , or 3,3-difluoroallyl group, more preferably 3-fluoroallyl group or 3,3-difluoroallyl group, particularly preferably 3,3-difluoroallyl group.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R1 of formula (1-1) has the same meaning as the above definition, and is preferably an ethynyl group, 1 -propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, or 3-butynyl group, more preferably ethynyl group, 1-propynyl group, propargyl group, or 2-butynyl group, particularly preferably is a propargyl group or a 2-butynyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• C2-C6 haloalkynyl group in R1 of formula (1-1) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro -1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-1-butynyl group
• a fluoro-2-butynyl group more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1- It is a butynyl group, particularly preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1
• the "phenyl group optionally substituted with 0 to 5 substituents B" in R1 of formula (1-1) is a phenyl group in which hydrogen atoms are optionally substituted with 1 to 5 substituents B.
• Preferred examples of "phenyl group optionally substituted with 0 to 5 substituents B" include phenyl group, cyanophenyl group, fluorophenyl group, chlorophenyl group, tolyl group, methoxyphenyl group, phenoxyphenyl group, methylsulfanylphenyl group, A methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more preferably a phenyl group, a cyanophenyl group, a fluorophen
• the 5- to 6-membered aromatic heterocyclic group of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" in R1 of formula (1-1) has the same meaning as the above definition.
• a pyridyl group More preferred are a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, and an oxadiazolyl group, and particularly preferred is a pyridyl group. , or a pyrimidinyl group.
• the "5- to 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B" is preferably a pyridyl group, 2-cyanopyridyl group, 3-cyanopyridyl group, 4-cyanopyridyl group, 2- Fluoropyridyl group, 3-fluoropyridyl group, 4-fluoropyridyl group, 2-chloropyridyl group, 3-chloropyridyl group, 4-chloropyridyl group, 2-bromopyridyl group, 3-bromopyridyl group, 4-bromopyridyl group group, 2-iodopyridyl group, 3-iodopyridyl group, 4-iodopyridyl group, 2-methylpyridyl group, 3-methylpyridyl group, 4-methylpyridyl group, 2-trifluoromethylpyridyl group, 3-trifluoro Methylpyr
• Rx1Rx2NC( O)-(herein, Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, or C1-- which may be optionally substituted with a substituent A) in R1 of formula (1-1) C6 alkyl group, C1 to C6 haloalkyl group, C3 to C8 cycloalkyl group optionally substituted with substituent B, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cyclo Rx1 and Rx2 represent an alkoxy group, a phenyl group optionally substituted with 0 to 5 substituents, a 5-6 membered aromatic heterocycl
• phenyloxycarbonyl group propargyloxycarbonyl group, phenyloxycarbonyl group, or 4-nitrophenyloxycarbonyl group, more preferably methoxycarbonyl group, ethoxycarbonyl group, isopropyloxycarbonyl group, cyclopropyloxycarbonyl group, and propargyloxycarbonyl group.
• phenyloxycarbonyl group, or 4-nitrophenyloxycarbonyl group and particularly preferably methoxycarbonyl group or ethoxycarbonyl group.
• Rx4S(O)p- in R1 of formula (1-1) (here, Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with substituent A, a C1 to C6 alkyl group, Haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, substituent A represents a C2 to C6 alkynyl group which may be optionally substituted, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p is 0, 1, or 2.
• Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group , phenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-methylphenylsulfonyl group, or 4-trifluoromethylphenylsulfonyl group, more preferably methylsulfonyl group, ethylsulfonyl group, trifluorophenylsulfonyl group, A fluoromethylsulfonyl group, a 4-fluoromethylsulfonyl group,
• the term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R1 of formula (1-1) has the same meaning as above.
• Preferred examples of the "3- to 6-membered ring group containing 1 to 2 oxygen atoms" include oxiran-2-yl group, oxetan-3-yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, Tetrahydro-2H-pyran-2-yl group, tetrahydro-2H-pyran-3-yl group, tetrahydro-2H-pyran-4-yl group, 1,4-dioxan-2-yl group, 3-dihydrofuran-2 (3H)-one group, 4-dihydrofuran-2(3H)-one group, 3-tetrahydro-2H-pyran-2-one group, or 4-tetrahydro-2H-pyran-2-one group, and more Preferably, a te
• R2 in formula (1-2) is a hydrogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C6 which may be optionally substituted with a substituent B.
• Rx1 and Rx2 are each independently a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group which may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, a substituent A C3 to C8 cycloalkyl group optionally substituted with B, a C2 to C6 alkenyl group optionally substituted with substituent A, a C2 to C6
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group that may be optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 that may be optionally substituted
• R2 is preferably a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group optionally substituted with substituent B.
• R2 in formula (1-2) contains a hydrogen atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R2 of formula (1-2) has the same meaning as the above definition, and is preferably a methyl group, Ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, or hexyl group, more preferably methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group.
• the "C1 to C6 alkyl group optionally substituted with substituent A” is preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, pentyl group, or hexyl group.
• cyanomethyl group 1-cyanoethyl group, 2-cyanoethyl group, 3-cyanopropyl group, 2-cyanopropan-2-yl group, cyclopropylmethyl group, cyclobutylmethyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group group, ethoxyethyl group, isopropyloxymethyl group, isopropyloxyethyl group, Benzyl group, 1-phenethyl group, 2-phenethyl group, 4-cyanophenylmethyl group, 2-fluorophenylmethyl group, 3-fluorophenylmethyl group, 4-fluorophenylmethyl group, 2-chlorophenylmethyl group, 3-chlorophenyl group Methyl group, 3,5-dichlorophenylmethyl group, 4-chlorophenylmethyl group, 2-methylphenylmethyl group, 3-methylphenylmethyl group, 4-methylphenylmethyl group, 2-trifluoromethylphen
• C1 to C6 haloalkyl group in R2 of formula (1-2) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2 , 2-trifluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 2,2,3,3,3-pentafluoropropyl group , 1,1,2,2,3,3,3-heptafluoropropyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, or 2,2,3,3,4, 4,5,5,5-nonafluoropentyl group, more preferably difluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, or 1,1,2,2,3,3,3-heptafluoropropyl group
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R2 of formula (1-2) has the same meaning as the above definition, and is preferably cyclo It is a propyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent B When substituent B is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with substituent B.
• the "C3 to C8 cycloalkyl group optionally substituted with substituent B" is preferably a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-(cyclopropane-1-carbonitrile) group, 2 -(cyclopropane-1-carbonitrile) group, 1-(1-nitrocyclopropyl) group, 1-(2-nitrocyclopropyl) group, 1-(1-cyclopropylcyclopropyl) group, 1-(2 -cyclopropylcyclopropyl) group, 1-(2-methoxycyclopropyl) group, 1-(2-ethoxycyclopropyl) group, 1-(1-phenylcyclopropyl) group, 1-(2-phenylcyclopropyl) group group, 1-(cyclopropylethane-1-one) group, 2-(cyclopropylethane-1-one) group, 1-(1-methoxycarbonylcycloprop
• the C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent A" in R2 of formula (1-2) has the same meaning as the above definition, and is preferably a vinyl group, 1-propenyl group, allyl group, 2-methylallyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group, allyl group, or 2-methylallyl group. , or 3-butenyl group, particularly preferably allyl group, 2-methylallyl group, or 3-butenyl group.
• the hydrogen atom in the C2 to C6 alkenyl group is optionally substituted with the substituent described in Substituent A.
• C2 to C6 haloalkenyl group in R2 of formula (1-2) has the same meaning as the above definition, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 3-fluoroallyl group. , or 3,3-difluoroallyl group, more preferably 3-fluoroallyl group or 3,3-difluoroallyl group, particularly preferably 3,3-difluoroallyl group.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R2 of formula (1-2) has the same meaning as the above definition, and is preferably an ethynyl group, 1 -propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, or 3-butynyl group, more preferably ethynyl group, 1-propynyl group, propargyl group, or 2-butynyl group, particularly preferably is a propargyl group or a 2-butynyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• C2-C6 haloalkynyl group in R2 of formula (1-2) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro -1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-1-butynyl group A fluoro-2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1-propynyl group, or a 4,4,4-trifluoro-1- A butynyl group, particularly preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propyl group
• the "phenyl group optionally substituted with 0 to 5 substituents B" in R2 of formula (1-2) is a phenyl group in which hydrogen atoms are optionally substituted with 1 to 5 substituents B.
• Preferred examples of "phenyl group optionally substituted with 0 to 5 substituents B" include phenyl group, cyanophenyl group, fluorophenyl group, chlorophenyl group, tolyl group, methoxyphenyl group, phenoxyphenyl group, methylsulfanylphenyl group, A methylsulfinylphenyl group, a methylsulfonylphenyl group, a trifluoromethylsulfanylphenyl group, a trifluoromethylsulfinylphenyl group, or a trifluoromethylsulfonylphenyl group, more preferably a phenyl group, a cyanophenyl group, a fluorophen
• the 5- to 6-membered aromatic heterocyclic group of the "5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents B" in R2 of formula (1-2) has the same meaning as the above definition.
• a pyridyl group More preferred are a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thienyl group, a thiazolyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, and an oxadiazolyl group, and particularly preferred is a pyridyl group. , or a pyrimidinyl group.
• the "5- to 6-membered aromatic heterocyclic group optionally substituted with 0 to 4 substituents B" is preferably a pyridyl group, 2-cyanopyridyl group, 3-cyanopyridyl group, 4-cyanopyridyl group, 2- Fluoropyridyl group, 3-fluoropyridyl group, 4-fluoropyridyl group, 2-chloropyridyl group, 3-chloropyridyl group, 4-chloropyridyl group, 2-bromopyridyl group, 3-bromopyridyl group, 4-bromopyridyl group group, 2-iodopyridyl group, 3-iodopyridyl group, 4-iodopyridyl group, 2-methylpyridyl group, 3-methylpyridyl group, 4-methylpyridyl group, 2-trifluoromethylpyridyl group, 3-trifluoro Methylpyr
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be appropriately substituted with a substituent A, C1 -C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, substituted A C2 to C6 alkynyl group that may be optionally substituted with group A, a C2 to C6 haloalkynyl group, a phenyl group that may be optionally substituted with 0 to 5 substituents, or 0 to 4 substituted with substituent B.
• phenyloxycarbonyl group propargyloxycarbonyl group, phenyloxycarbonyl group, or 4-nitrophenyloxycarbonyl group, and more preferably methoxycarbonyl group, ethoxycarbonyl group, isopropyloxycarbonyl group, cyclopropyloxycarbonyl group, and propargyloxycarbonyl group.
• phenyloxycarbonyl group, or 4-nitrophenyloxycarbonyl group and particularly preferably methoxycarbonyl group or ethoxycarbonyl group.
• Rx4S(O)p- in R2 of formula (1-2) (here, Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkyl group) Haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, substituent A represents a C2 to C6 alkynyl group which may be optionally substituted, a C2 to C6 haloalkynyl group, or a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p is 0, 1, or 2.
• Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group , phenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-methylphenylsulfonyl group, or 4-trifluoromethylphenylsulfonyl group, more preferably methylsulfonyl group, ethylsulfonyl group, trifluorophenylsulfonyl group, A fluoromethylsulfonyl group, a 4-fluoromethylsulfonyl group,
• the term "3- to 6-membered ring group containing 1 to 2 oxygen atoms" in R2 of formula (1-2) has the same meaning as above.
• Preferred examples of the "3- to 6-membered ring group containing 1 to 2 oxygen atoms" include oxiran-2-yl group, oxetan-3-yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, Tetrahydro-2H-pyran-2-yl group, tetrahydro-2H-pyran-3-yl group, tetrahydro-2H-pyran-4-yl group, 1,4-dioxan-2-yl group, 3-dihydrofuran-2 (3H)-one group, 4-dihydrofuran-2(3H)-one group, 3-tetrahydro-2H-pyran-2-one group, or 4-tetrahydro-2H-pyran-2-one group, and more Preferably, a te
• R3 in formula (1-1) or formula (1-2) is a hydrogen atom, a C1 to C6 alkyl group that may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituent B.
• C6 alkynyl group, C2 to C6 haloalkynyl group, Rx1Rx2NC( O)- (where Rx1 and Rx2 are each independently substituted with a hydrogen atom, a hydroxyl group, a cyano group, or a substituent A) C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A.
• Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent B, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 haloalkynyl group, Alternatively, it represents a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. ) represents.
• R3 in formula (1-1) or formula (1-2) contains a hydrogen atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition. , preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, or isobutyl group, more preferably a methyl group, ethyl group, propyl group, or isopropyl group, still more preferably a methyl group , ethyl group, or propyl group, and particularly preferably methyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1 to C6 haloalkyl group in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2- Difluoroethyl group, 2,2,2-trifluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, or 1,1,2, 2,3,3,3-heptafluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,2 , 2,2-tetrafluoroethyl group, or 1,1,2,2,3,3,3-heptafluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoromethyl group. Ethyl group or 2,2,2,2-
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition. and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and particularly preferably a cyclo It is a propyl group or a cyclobutyl group.
• the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with the substituent described in Substituent A.
• the C2 to C6 alkenyl group of "C2 to C6 alkenyl group optionally substituted with substituent A" in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition. , preferably vinyl group, 1-propenyl group, allyl group, 2-methylallyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group, Allyl group, 2-methylallyl group, or 3-butenyl group, particularly preferably allyl group, 2-methylallyl group, or 3-butenyl group.
• a substituent described in Substituent A is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent described in Substituent A.
• C2-C6 haloalkenyl group in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably 2-fluorovinyl group, 2,2-difluorovinyl group. group, 3-fluoroallyl group, or 3,3-difluoroallyl group, more preferably 3-fluoroallyl group or 3,3-difluoroallyl group, particularly preferably 3,3-difluoroallyl group. It is the basis.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group which may be optionally substituted with substituent A" in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition, Preferably, it is an ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, or 3-butynyl group, and more preferably an ethynyl group, 1-propynyl group, propargyl group, or 2-butynyl group. It is a butynyl group, particularly preferably a propargyl group or a 2-butynyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• the "C2-C6 haloalkynyl group" in R3 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, 3 , 3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-2-butynyl group, more preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, or 4,4, A 4-trifluoro-1-butynyl group, particularly preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
• Rx1 and Rx2 together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, Represents a group forming an azepanyl group or an azocanyl group.) Each term has the same meaning as above.
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, C1
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, C1
• An oxycarbonyl group a cyclopentyloxycarbonyl group, an allyloxycarbonyl group, a propargyloxycarbonyl group, a phenyloxycarbonyl group, or a 4-nitrophenyloxycarbonyl group, and more preferably a methoxycarbonyl group, an ethoxycarbonyl group, and a propyloxycarbonyl group.
• Rx4S(O)p- in R3 of formula (1-1) or formula (1-2) (here, Rx4 is a hydroxyl group, a halogen atom, or a C1 to C6 group which may be appropriately substituted with a substituent A)
• C2-C6 halo represents an alkenyl group, a C2 to C6 alkynyl group optionally substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group optionally substituted with 0 to 5 substituents B
• p is represents an integer of 0, 1, or 2
• Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group , phenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-methylphenylsulfonyl group, or 4-trifluoromethylphenylsulfonyl group, more preferably methylsulfonyl group, ethylsulfonyl group, trifluorophenylsulfonyl group, A fluoromethylsulfonyl group, a 4-methylphenylsulfonyl group,
• R4 in formula (1-1) or formula (1-2) is a hydrogen atom, a C1 to C6 alkyl group that may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituent B.
• C3 to C8 cycloalkyl group which may be substituted C2 to C6 alkenyl group which may be optionally substituted with substituent A, C2 to C6 haloalkenyl group which may be optionally substituted with substituent A.
• C6 alkynyl group, C2 to C6 haloalkynyl group, Rx1Rx2NC( O)- (where Rx1 and Rx2 are each independently substituted with a hydrogen atom, a hydroxyl group, a cyano group, or a substituent A) C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A.
• Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent B, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 haloalkynyl group, Alternatively, it represents a phenyl group which may be optionally substituted with 0 to 5 substituents B, and p represents an integer of 0, 1, or 2. ) represents.
• R4 in formula (1-1) or formula (1-2) contains a hydrogen atom.
• the C1 to C6 alkyl group of "C1 to C6 alkyl group optionally substituted with substituent A" in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition. , preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, or an isopropyl group, and particularly preferably a methyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1 to C6 haloalkyl group in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2- Difluoroethyl group, 2,2,2-trifluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, or 1,1,2, 2,3,3,3-heptafluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group, Particularly preferred is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition. and is preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, more preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and particularly preferably a cyclo It is a propyl group or a cyclobutyl group.
• the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted with the substituent described in Substituent A.
• the C2 to C6 alkenyl group of "C2 to C6 alkenyl group optionally substituted with substituent A" in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition. , preferably vinyl group, 1-propenyl group, allyl group, 2-methylallyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group, Allyl group, 2-methylallyl group, or 3-butenyl group, particularly preferably allyl group, 2-methylallyl group, or 3-butenyl group.
• a substituent described in Substituent A is present, a hydrogen atom in a C2 to C6 alkenyl group is optionally substituted with the substituent described in Substituent A.
• C2-C6 haloalkenyl group in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably 2-fluorovinyl group, 2,2-difluorovinyl group. group, 3-fluoroallyl group, or 3,3-difluoroallyl group, more preferably 3-fluoroallyl group or 3,3-difluoroallyl group, particularly preferably 3,3-difluoroallyl group. It is the basis.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R4 of formula (1-1) or formula (1-2) is as defined above, Preferably, it is an ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, or 3-butynyl group, and more preferably an ethynyl group, 1-propynyl group, propargyl group, or 2-butynyl group. It is a butynyl group, particularly preferably a propargyl group or a 2-butynyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• C2-C6 haloalkynyl group in R4 of formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, 3 , 3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro-2-butynyl group, more preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, or 4,4, A 4-trifluoro-1-butynyl group, particularly preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
• Rx1 and Rx2 together with the nitrogen atom to which they are bonded, represent an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a thiomorpholinyl group, a dioxothiomorpholinyl group, a thiazolidinyl group, Represents a group forming an azepanyl group or an azocanyl group.) Each term has the same meaning as above.
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, C1 which may be appropriately substituted with a substituent A
• -C6 alkyl group C1-C6 haloalkyl group
• C3-C8 cycloalkyl group optionally substituted with substituent B
• C2-C6 alkenyl group optionally substituted with substituent A C2- C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 haloalkynyl group
• phenyl group optionally substituted with 0 to 5 substituents B or substituent B represents a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4.
• Each term has the same meaning as defined above.
• Rx3 is a hydrogen atom, a hydroxyl group, a halogen atom, C1 which may be appropriately substituted with a substituent A
• -C6 alkyl group C1-C6 haloalkyl group
• C3-C8 cycloalkyl group optionally substituted with substituent B
• C2-C6 alkenyl group optionally substituted with substituent A C2- C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 haloalkynyl group
• phenyl group optionally substituted with 0 to 5 substituents B or substituent B represents a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4.
• Each term has the same meaning as defined above.
• Rx4S(O)p- in R4 of formula (1-1) or formula (1-2) (here, Rx4 is a hydroxyl group, a halogen atom, or a C1 to C6 group that may be optionally substituted with a substituent A) Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 halo represents an alkenyl group, a C2 to C6 alkynyl group optionally substituted with substituent A, a C2 to C6 haloalkynyl group, or a phenyl group optionally substituted with 0 to 5 substituents B, and p is represents an integer of 0, 1, or 2) has the same meaning as defined above.
• Rx4S(O)p- is preferably a methylsulfonyl group, an ethylsulfonyl group, a trifluoromethylsulfonyl group, a 1,1,2,2,2-pentafluoroethylsulfonyl group, a cyclopropylsulfonyl group, a cyclopentylsulfonyl group , phenylsulfonyl group, 4-fluorophenylsulfonyl group, 4-chlorophenylsulfonyl group, 4-methylphenylsulfonyl group, or 4-trifluoromethylphenylsulfonyl group, more preferably methylsulfonyl group, ethylsulfonyl group, trifluorophenylsulfonyl group, A fluoromethylsulfonyl group, a 4-methylphenylsulfonyl group,
• R5 in formula (1-1) or formula (1-2) is a cyano group, a halogen atom, a C1 to C6 alkoxy group optionally substituted with substituent A, a C1 to C6 haloalkoxy group, a substituted C3 to C8 cycloalkoxy group optionally substituted with group A, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, optionally substituted with substituent A a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, or Rx4S(O)p- (where Rx4 is a hydroxyl group, a halogen atom, or a C1-C6 alkynyl group optionally substituted with a substituent A); Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent B, C2-
• R5 is a cyano group, a halogen atom, a C1 to C6 alkoxy group optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 cyclo optionally substituted with a substituent A.
• An alkoxy group or Rx4S(O)p- (where Rx4 and p have the same meanings as above) is preferred,
• R5 is a cyano group, a halogen atom, a C1 to C6 alkoxy group optionally substituted with substituent A, or Rx4S(O)p- (where Rx4 and p have the same meanings as above).
• Rx4 and p have the same meanings as above.
• R5 is preferably Rx4S(O)p- (where Rx4 and p have the same meanings as above).
• R5 in formula (1-1) or formula (1-2) contains a cyano group.
• halogen atom in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a fluorine atom, chlorine atom, bromine atom, or iodine atom, and Preferably, it is a fluorine atom, a chlorine atom, or a bromine atom, and particularly preferably a chlorine atom or a bromine atom.
• the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent A" in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition.
• the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent described in Substituent A.
• the "C1 to C6 haloalkoxy group" in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, 2, 2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, or 1,1, 2,2,3,3,3-heptafluoropropyloxy group, more preferably trifluoromethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2- A pentafluoroethoxy group or a 1,1,2,2,3,3,3-heptafluoropropyloxy group, particularly a trifluoromethoxy group or a 1,1,2,2,2-pentafluoropropyloxy group. It is an ethoxy group.
• the C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent A" in R5 in formula (1-1) or formula (1-2) is as defined above. They are synonymous, and are preferably a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group, and particularly preferably a cyclopropyloxy group. It is the basis. When the substituent A is present, one hydrogen atom in the C3 to C8 cycloalkoxy group is substituted with the substituent A.
• the C2 to C6 alkenyl group of "C2 to C6 alkenyl group optionally substituted with substituent A" in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition. It is preferably a vinyl group, a 1-propenyl group, or an allyl group, more preferably a vinyl group or an allyl group, and particularly preferably an allyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkenyl group is substituted with the substituent A.
• the "C2 to C6 haloalkenyl group" in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a 2-fluorovinyl group, a 2,2-difluoro A vinyl group, a 3-fluoroallyl group, or a 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, and particularly preferably a 3,3-difluoroallyl group. It is an allyl group.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition.
• ethynyl group, 1-propynyl group, propargyl group, 2-butynyl group, or 3-butynyl group more preferably ethynyl group, 1-propynyl group, or propargyl group, particularly preferably , ethynyl group, or propargyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• C2 to C6 haloalkynyl group in R5 in formula (1-1) or formula (1-2) has the same meaning as the above definition, and is preferably a 2-fluoroethynyl group or a 2-chloroethynyl group.
• Rx4S(O)p- in R5 of formula (1-1) or formula (1-2) (here, Rx4 is a hydroxyl group, a halogen atom, or a C1 to C6 group that may be appropriately substituted with a substituent A)
• C2-C6 halo represents an alkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, a C2-C6 haloalkynyl group, or a phenyl group optionally optionally substituted with 0-5 substituents B; represents an integer of 0, 1, or 2) has the same meaning as defined above.
• Rx4S(O)p- is preferably a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, an ethylsulfanyl group, an ethylsulfinyl group, an ethylsulfonyl group, a propylsulfanyl group, a propylsulfinyl group, a propylsulfonyl group, or a butylsulfanyl group.
• Het represents the formula (Het).
• G in formula (Het) represents CR6 or a nitrogen atom.
• the bonding position cut by the wavy line in formula (Het) represents the bonding position of Het in formulas (1-1) and (1-2).
• R6 in the formula (Het) is a hydrogen atom, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituted with substituent B. a C3-C8 cycloalkyl group that may be optionally substituted with a substituent A, a C2-C6 alkenyl group that may be optionally substituted with a substituent A, a C2-C6 haloalkenyl group that may be optionally substituted with a substituent A; group, or a C2-C6 haloalkynyl group.
• R6 is a hydrogen atom, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or C3 to C3 optionally substituted with substituent B.
• R6 is preferably a hydrogen atom, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, or a C1 to C6 haloalkyl group,
• R6 is preferably a hydrogen atom, a halogen atom, or a C1 to C6 alkyl group which may be optionally substituted with a substituent A.
• R6 in formula (Het) includes a hydrogen atom and a cyano group.
• halogen atom in R6 of formula (Het) has the same meaning as the above definition, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or A bromine atom, particularly preferably a chlorine atom or a bromine atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R6 of formula (Het) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group.
• a propyl group an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, or a propyl group, and particularly preferably a methyl group.
• substituent A one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1-C6 haloalkyl group in R6 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a dibromomethyl group, a 2,2-difluoromethyl group.
• Ethyl group, 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, or 2,2,3,3,3-pentafluoropropyl group more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, or a 2,2,3 , 3,3-pentafluoropropyl group, particularly preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R6 of formula (Het) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with the substituent A.
• the C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent A" in R6 of formula (Het) has the same meaning as the above definition, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group, and particularly preferably an allyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkenyl group is substituted with the substituent A.
• C2-C6 haloalkenyl group in R6 of formula (Het) has the same meaning as the above definition, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or A 3,3-difluoroallyl group, more preferably a 3-fluoroallyl group or a 3,3-difluoroallyl group, particularly preferably a 3,3-difluoroallyl group.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R6 of formula (Het) has the same meaning as the above definition, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, or a propargyl group, and particularly preferably an ethynyl group or a propargyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with the substituent A.
• C2-C6 haloalkynyl group in R6 of formula (Het) has the same meaning as the above definition, and is preferably a 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodo Ethynyl group, 3,3-difluoro-1-propynyl group, 3-chloro-3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, or 3,3,3 -trifluoro-1-propynyl group, more preferably 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, or 3,3,3-trifluoro-1-propynyl group,
• R7 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituted with substituent B.
• a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C2 to C6 alkenyl group which may be optionally substituted with a substituent A, a C2 to C6 haloalkenyl group which may be optionally substituted with a substituent A;
• Alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 haloalkoxy group optionally substituted with substituent A Represents a cycloalkoxy group or Rx4S(O)p- (where Rx4 and p have the same meanings as above).
• R7 is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and C3 optionally substituted with substituent B.
• R7 is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and C3 optionally substituted with substituent B.
• R7 is a hydrogen atom, a hydroxyl group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent A, a C3-C8 cycloalkyl group optionally substituted with substituent B, substituent A A C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or Rx4S(O)p- (where Rx4 and p have the same meanings as above) which may be optionally substituted with is preferred.
• R7 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
• the halogen atom in R7 of formula (Het) has the same meaning as the above definition, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. and particularly preferably a chlorine atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R7 of formula (Het) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , a propyl group, an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, or an isopropyl group, and particularly preferably a methyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1 to C6 haloalkyl group in R7 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 -trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or A 2,2,2-trifluoroethyl group, particularly preferably a difluoromethyl group or a trifluoromethyl group.
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R7 of formula (Het) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent B When the substituent B is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with the substituent B.
• the C2 to C6 alkenyl group of the "C2 to C6 alkenyl group optionally substituted with substituent A" in R7 of formula (Het) has the same meaning as the above definition, and is preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group, or allyl group, particularly preferably vinyl group, or It is an allyl group.
• substituent A is present, one hydrogen atom in the C2 to C6 alkenyl group is substituted with the substituent A.
• C2-C6 haloalkenyl group in R7 of formula (Het) has the same meaning as the above definition, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, or a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group, or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group, 2,2-difluorovinyl group, or 3-fluoroallyl group. , or 3,3-difluoroallyl group, particularly preferably 2,2-difluorovinyl group or 3,3-difluoroallyl group.
• the C2 to C6 alkynyl group of the "C2 to C6 alkynyl group optionally substituted with substituent A" in R7 of formula (Het) has the same meaning as the above definition, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, more preferably an ethynyl group, a 1-propynyl group, or a propargyl group, and particularly preferably an ethynyl group.
• substituent described in Substituent A is present, one hydrogen atom in the C2 to C6 alkynyl group is substituted with Substituent A.
• C2-C6 haloalkynyl group in R7 of formula (Het) has the same meaning as the above definition, and is preferably a 3,3-difluoro-1-propynyl group, a 3,3,3-trifluoro-1 -propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- 2-butynyl group, more preferably 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, or 4,4,4-trifluoro-1-butynyl group and particularly preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
• the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent A" in R7 of formula (Het) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , propyloxy group, isopropyloxy group, butoxy group, or isobutoxy group, more preferably methoxy group, ethoxy group, propyloxy group, or isopropyloxy group, particularly preferably methoxy group, ethoxy group, or It is a propyloxy group.
• the substituent described in Substituent A is present, the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent described in Substituent A.
• C1 to C6 haloalkoxy group in R7 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, or 1,1,2,2,3,3,3- Heptafluoropropyloxy group, more preferably trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2 -pentafluoroethoxy group or 1,1,2,2,3,3,3-heptafluoropropyloxy group, particularly preferably 2,2,2-trifluoroethoxy group.
• the C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent A" in R7 of formula (Het) has the same meaning as the above definition, and is preferably cyclopropyloxy.
• substituent A When the substituent A is present, one hydrogen atom in the C3 to C8 cycloalkoxy group is substituted with the substituent A.
• Rx4S(O)p- in R7 of formula (Het) (where Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group that may be optionally substituted with substituent A, or a C1 to C6 haloalkyl group) , a C3-C8 cycloalkyl group optionally substituted with substituent B, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, optionally substituted with substituent A represents an optionally substituted C2 to C6 alkynyl group, a C2 to C6 haloalkynyl group, or a phenyl group optionally substituted with 0 to 5 substituents B, and p is an integer of 0, 1, or 2.
• each term (represented) has the same meaning as defined above.
• the hydrogen atom in the phenyl group can be arbitrarily substituted between 1 and 5 by independent substituents B.
• Rx4 is preferably a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent B, or a substituted A phenyl group that may be optionally substituted with 0 to 5 substituents with group B, more preferably a C1 to C6 alkyl group that may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group that may be optionally substituted with substituent B.
• Rx4S(O)p- is preferably a methylsulfanyl group, methylsulfinyl group, methylsulfonyl group, ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoro Methylsulfonyl group, 1,1,2,2,2-pentafluoroethylsulfanyl group, 1,1,2,2,2-pentafluoroethylsulfinyl group, 1,1,2,2,2-pentafluoroethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl
• R8 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituted with substituent B.
• a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group which may be optionally substituted with a substituent A;
• R8 is a hydrogen atom, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and a C3 to C8 cycloalkyl group optionally substituted with substituent B.
• R8 is preferably a halogen atom, a C1 to C6 haloalkyl group, a C1 to C6 haloalkoxy group, or Rx4S(O)p- (where Rx4 and p have the same meanings as above),
• R8 is preferably a C1 to C6 haloalkyl group.
• R8 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
• the halogen atom in R8 of formula (Het) has the same meaning as the above definition, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. and particularly preferably a fluorine atom or a chlorine atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R8 of formula (Het) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , a propyl group, an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, or an isopropyl group, and particularly preferably a methyl group or an ethyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1 to C6 haloalkyl group in R8 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, Dibromomethyl group, monoiodomethyl group, diiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2 -difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,2,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2 , 2-trichloroethyl group, 2-
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R8 of formula (Het) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent B When substituent B is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with substituent B.
• the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent A" in R8 of formula (Het) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , a propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, more preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group, and particularly preferably a methoxy group or an ethoxy group. be.
• the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted with the substituent described in Substituent A.
• the "C1 to C6 haloalkoxy group" in R8 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, or 1,1,2,2,3,3,3- A heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a 1,1, A 2,2,3,3,3-heptafluoropropyloxy group, particularly a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
• the C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent A" in R8 of formula (Het) has the same meaning as the above definition, and is preferably cyclopropyloxy. group, cyclobutoxy group, cyclopentyloxy group, or cyclohexyloxy group, more preferably cyclopropyloxy group or cyclobutoxy group, particularly preferably cyclopropyloxy group.
• substituent A When the substituent A is present, one hydrogen atom in the C3 to C8 cycloalkoxy group is substituted with the substituent A.
• Rx4S(O)p- in R8 of formula (Het) (where Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group that may be appropriately substituted with substituent A, or a C1 to C6 haloalkyl group) , a C3-C8 cycloalkyl group optionally substituted with substituent B, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, optionally substituted with substituent A represents an optionally substituted C2 to C6 alkynyl group, a C2 to C6 haloalkynyl group, or a phenyl group optionally substituted with 0 to 5 substituents B, and p is an integer of 0, 1, or 2.
• each term has the same meaning as defined above.
• the hydrogen atom in the phenyl group can be arbitrarily substituted between 1 and 5 by independent substituents B.
• Rx4 is preferably a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent B, or a substituted A phenyl group that may be optionally substituted with 0 to 5 substituents with group B, more preferably a C1 to C6 alkyl group that may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group that may be optionally substituted with substituent B.
• Rx4S(O)p- is preferably a methylsulfanyl group, methylsulfinyl group, methylsulfonyl group, ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoro Methylsulfonyl group, 1,1,2,2,2-pentafluoroethylsulfanyl group, 1,1,2,2,2-pentafluoroethylsulfinyl group, 1,1,2,2,2-pentafluoroethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl
• R9 in formula (Het) is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituted with substituent B.
• a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A, a C1 to C6 alkoxy group which may be optionally substituted with a substituent A, a C1 to C6 haloalkoxy group which may be optionally substituted with a substituent A;
• R9 is a hydrogen atom, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or Rx4S(O)p- (where Rx4 and p are the above-mentioned ) is preferable, Furthermore, R9 is preferably a hydrogen atom, a halogen atom, or a C1 to C6 haloalkyl group, In particular, R9 is preferably a hydrogen atom.
• R9 in formula (Het) includes a hydrogen atom, a hydroxyl group, and a cyano group.
• the halogen atom in R9 of formula (Het) has the same meaning as the above definition, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and more preferably a fluorine atom, a chlorine atom, or a bromine atom. and particularly preferably a fluorine atom or a chlorine atom.
• the C1 to C6 alkyl group of the "C1 to C6 alkyl group optionally substituted with substituent A" in R9 of formula (Het) has the same meaning as the above definition, and is preferably a methyl group or an ethyl group. , a propyl group, an isopropyl group, a butyl group, or an isobutyl group, more preferably a methyl group, an ethyl group, or an isopropyl group, and particularly preferably a methyl group or an ethyl group.
• substituent A When the substituent A is present, one hydrogen atom in the C1 to C6 alkyl group is substituted with the substituent A.
• C1 to C6 haloalkyl group in R9 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 -trifluoroethyl group, 1,2,2,2-tetrafluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, or 1,1,2,2,3,3,3-hepta
• a fluoropropyl group more preferably a trifluoromethyl group, a 1,2,2,2-tetrafluoroethyl group, a 1,1,2,2,2-pentafluoroethyl group, or a 1,1,2, A 2,3,3,3-heptafluoropropyl group, particularly a trifluoromethyl group or a 1,1,2,2,2-pentafluoroethyl group.
• the C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent B" in R9 of formula (Het) has the same meaning as the above definition, and is preferably a cyclopropyl group. , a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group, and particularly preferably a cyclopropyl group.
• substituent B When substituent B is present, one hydrogen atom in the C3 to C8 cycloalkyl group is substituted with substituent B.
• the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with substituent A" in R9 of formula (Het) has the same meaning as the above definition, and is preferably a methoxy group or an ethoxy group. , propyloxy group, isopropyloxy group, butoxy group, or isobutoxy group, more preferably methoxy group, ethoxy group, propyloxy group, or isopropyloxy group, particularly preferably methoxy group or ethoxy group. be.
• the substituent A is present, the hydrogen atom in the C1 to C6 alkoxy group is substituted with the substituent A.
• the "C1 to C6 haloalkoxy group" in R9 of formula (Het) has the same meaning as the above definition, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2, 2-trifluoroethoxy group, 1,2,2,2-tetrafluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, or 1,1,2,2,3,3,3- A heptafluoropropyloxy group, more preferably a trifluoromethoxy group, a 1,2,2,2-tetrafluoroethoxy group, a 1,1,2,2,2-pentafluoroethoxy group, or a 1,1, A 2,2,3,3,3-heptafluoropropyloxy group, particularly a trifluoromethoxy group or a 1,1,2,2,2-pentafluoroethoxy group.
• the C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent A" in R9 of formula (Het) has the same meaning as the above definition, and is preferably cyclopropyloxy.
• substituent A When the substituent A is present, one hydrogen atom in the C3 to C8 cycloalkoxy group is substituted with the substituent A.
• Rx4S(O)p- in R9 of formula (Het) (where Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group that may be appropriately substituted with substituent A, a C1 to C6 haloalkyl group) , a C3-C8 cycloalkyl group optionally substituted with substituent B, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, optionally substituted with substituent A represents an optionally substituted C2 to C6 alkynyl group, a C2 to C6 haloalkynyl group, or a phenyl group optionally substituted with 0 to 5 substituents B, and p is an integer of 0, 1, or 2.
• each term has the same meaning as defined above.
• the hydrogen atom in the phenyl group can be arbitrarily substituted between 1 and 5 by independent substituents B.
• Rx4 is preferably a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent B, or a substituted A phenyl group that may be optionally substituted with 0 to 5 substituents with group B, more preferably a C1 to C6 alkyl group that may be optionally substituted with substituent A, a C1 to C6 haloalkyl group, or a C1 to C6 haloalkyl group that may be optionally substituted with substituent B.
• Rx4S(O)p- is preferably a methylsulfanyl group, methylsulfinyl group, methylsulfonyl group, ethylsulfanyl group, ethylsulfinyl group, ethylsulfonyl group, trifluoromethylsulfanyl group, trifluoromethylsulfinyl group, trifluoro Methylsulfonyl group, 1,1,2,2,2-pentafluoroethylsulfanyl group, 1,1,2,2,2-pentafluoroethylsulfinyl group, 1,1,2,2,2-pentafluoroethylsulfonyl group, cyclopropylsulfanyl group, cyclopropylsulfinyl
• Substituent A is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, a substituent A phenyl group that may be optionally substituted with 0 to 5 substituents with group C, a 5- to 6-membered aromatic heterocyclic group that may be optionally substituted with 0 to 4 substituents, and 3- to 6-membered aromatic heterocyclic groups containing 1 to 2 oxygen atoms. selected from the group consisting of ring groups.
• substituted A is a cyano group, a halogen atom, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, and a phenyl group that may be optionally substituted with 0 to 5 substituents. group, a 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents C, and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms.
• substituted A is a cyano group, a halogen atom, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, and a 5- to 6-membered aromatic heterocycle which may be optionally substituted with 0 to 4 substituents C. selected from the group consisting of:
• substituted A include hydroxyl group; cyano group; nitro group; As halogen atoms, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group; As C1 to C6 alkoxy groups, methoxy group, ethoxy group, propyloxy group, and isopropyloxy group; As the C1 to C6 haloalkoxy group, difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group , and 2,2,3,3,3-pentafluoropropyloxy group; As a C
• substituted A cyano group
• a halogen atom a fluorine atom, a chlorine atom, a bromine atom
• a C3 to C8 cycloalkyl group a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group
• C1 to C6 alkoxy groups methoxy group, ethoxy group, propyloxy group, and isopropyloxy group
• the C1 to C6 haloalkoxy group difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group, 2,2,2-trifluoroethoxy group, 2,2,3,3-tetrafluoropropyloxy group , and 2,2,3,3,3-pentafluoropropyloxy group
• the phenyl group which may be optionally substituted with 0
• Examples of the 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents C include a pyridyl group, a pyridine
• substituteduent A cyano group; As a halogen atom, a fluorine atom; As a C3 to C8 cycloalkyl group, a cyclopropyl group; As a C1 to C6 alkoxy group, a methoxy group and an ethoxy group;
• substituents C include phenyl group, cyanophenyl group, fluorophenyl group, chlorophenyl group, dichlorophenyl group, tolyl group, trifluoromethylphenyl group, cyclopropylphenyl group, methoxyphenyl group.
• trifluoromethoxyphenyl group methylsulfonylphenyl group, trifluoromethylsulfonylphenyl group, and trifluoromethylsulfonylphenyl group
• Examples of the 5- to 6-membered aromatic heterocyclic group which may be optionally substituted with 0 to 4 substituents C include a pyridyl group, a pyridine-N-oxide group, a 2-fluoropyridyl group, a 3-fluoropyridyl group, and a 4-fluoropyridyl group.
• Substituent B is a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, C3-C8 cycloalkoxy group, and Rx5S(O)p- (where Rx5 is a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 haloalkyl group, represents a cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, or a C2-C6 haloalky
• substituted B includes a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 halo selected from the group consisting of an alkoxy group, a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p have the same meanings as above).
• substituted B is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.
• substituted alkyl groups include hydroxyl group; cyano group; nitro group; As halogen atoms, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; As C1 to C6 alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group and hexyl group; C1 to C6 haloalkyl groups include difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, dibromomethyl group, 2,2-difluoroethyl group, 2,2 , 2-trifluoroethyl group, 1,1,2,2-tetrafluor
• substitutedine B include hydroxyl group; cyano group; As halogen atoms, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; As C1 to C6 alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and t-butyl group; As the C1 to C6 haloalkyl group, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, Fluoroethyl group, and heptafluoropropyl group; As a C3 to C8 cycloalkyl group, a cyclopropyl group; As C3 to C8 cycloal
• substitutedine atoms As C1 to C6 alkyl groups, methyl group, ethyl group, propyl group, and isopropyl group; As a C1 to C6 haloalkyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group; As C1 to C6 alkoxy groups, methoxy group, ethoxy group, and propyloxy group; As a C1 to C6 haloalkoxy group, a trifluoromethoxy group; Examples of Rx5S(O)p- include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group
• Substituent C is a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, selected from the group consisting of a C3-C8 cycloalkoxy group, and Rx5S(O)p- (wherein Rx5 and p have the same meanings as above).
• substituted C includes a cyano group, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, and a C1 to C6 haloalkoxy group. selected from the group consisting of:
• substituted C is selected from the group consisting of a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, and a C1-C6 alkoxy group.
• substituted C cyano group
• halogen atoms fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms
• C1 to C6 alkyl groups methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group and hexyl group
• C1 to C6 haloalkyl groups include difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloromethyl group, dibromomethyl group, 2,2-difluoroethyl group, 2,2 , 2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,
• substituted C cyano group
• halogen atoms fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms
• C1 to C6 alkyl groups methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, and t-butyl group
• C1 to C6 haloalkyl group difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, Fluoroethyl group, and heptafluoropropyl group
• a C3 to C8 cycloalkyl group a cyclopropyl group
• C1 to C6 alkyl groups methyl group, ethyl group, prop
• substituted C cyano group
• halogen atoms fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms
• C1 to C6 alkyl groups methyl group, ethyl group, propyl group, and isopropyl group
• a C1 to C6 haloalkyl group a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and a heptafluoropropyl group
• C1 to C6 alkoxy groups methoxy group, ethoxy group, and propyloxy group
• Rx5S(O)p- include a methylsulfanyl group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfin
• the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may contain one or more asymmetric atoms.
• the isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.
• the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may have one or two axial asymmetries.
• the isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.
• the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may include geometric isomers.
• the isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.
• the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may include rotamers.
• the isomer ratio at this time is a mixture ratio of individual or arbitrary ratios, and is not particularly limited.
• the compounds represented by formula (1-1), formula (1-2), formula (1-3), and formula (1-4) may be capable of forming salts.
• Examples include, but are not limited to, acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium. Salts that can be used as harmful arthropod control agents for agriculture and horticulture are preferred.
• the specific compounds of the present invention have the structural formulas C-1 to C-224 representing Het (Here, Het has the same meaning as above) shown in Table 1 (Here, the bond position cut by the wavy line is , represents the bonding position of Het in Table 2).
• the description "2-F-Ph” in Tables 3 and 4 means a phenyl group with a fluorine atom bonded to the 2-position
• “2-Me-Ph” The description means that it is a phenyl group with a methyl group bonded to the 2-position
• 2-Py represents a pyridin-2-yl group
• 3-Py represents a pyridin-3-yl group
• 4-Py represents a pyridin-4-yl group
• 1-Pyra represents a 1H-pyrazol-1-yl group
• 1-Tria represents a 1H-triazol-1-yl group
• other descriptions are also available. The same is true.
• production method A methods for producing the compounds represented by formula (1-1) and formula (1-2) are illustrated as production method A to production method AP.
• the method for producing the compound of the present invention is not limited to these.
• Rk is R1 or R2, and R1 and R2 are a hydrogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and optionally substituted with substituent B.
• a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent A
• a C2 to C6 alkenyl group which may be optionally substituted with a substituent A
• a C2 to C6 haloalkenyl group which may be optionally substituted with a substituent A an alkynyl group, a C2-C6 haloalkynyl group, a phenyl group that may be optionally substituted with 0 to 5 substituents, and a 5- to 6-membered aromatic heterocyclic group that may be optionally substituted with 0 to 4 substituents B.
• alkenyl group C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 haloalkynyl group, or optionally substituted with 0 to 5 substituents B.
• p represents an integer of 0, 1, or 2.
• Ra represents a hydrogen atom or a C1-C6 alkyl group which may be optionally substituted with a substituent A.
• Production method A is a method for obtaining compounds represented by formula (3-1) and formula (3-2) containing a production intermediate of the compound of the present invention, in which the compound represented by formula (2) and Rk -NHNH 2 in a solvent.
• the ratio thereof is not particularly limited, and either one may be used alone or a mixture of any ratio may be used. None.
• Rk-NHNH 2 used in this reaction can be obtained as a commercial product or produced by a known method.
• Rk-NHNH 2 may be a salt formed with an acidic compound such as hydrochloric acid or hydrobromic acid, and is not particularly limited as long as the desired reaction proceeds.
• Rk-NHNH 2 used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds, but preferably , 1 equivalent or more and 20 equivalents or less.
• This reaction can be carried out in the presence of an acid.
• acids to be used include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and p-toluenesulfonic acid, and are not particularly limited as long as the desired reaction proceeds.
• acetic acid or trifluoroacetic acid is preferred.
• the use of an acid is not essential.
• the amount of acid used in this reaction may be 1 equivalent or more relative to the compound represented by formula (2), and is not particularly limited as long as the desired reaction proceeds, but preferably, It is 1 equivalent or more and 50 equivalents or less. Furthermore, when the acid used is a liquid, it can also be used as a solvent.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol, isopropanol and trifluoroethanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate and isopropyl acetate; Ester solvents such as butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (2). be.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 180°C or below the boiling point of the solvent.
• an aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Moisture can be removed from the reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above using a drying agent such as sodium sulfate or magnesium sulfate. isn't it.
• reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compounds do not decompose.
• the reaction mixture containing the compounds represented by formula (3-1) and formula (3-2) obtained after solvent distillation is subjected to washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It can be purified by After purification, the compound of formula (3-1) and the compound of formula (3-2) may be separated, and the separation may be appropriately set depending on the desired purity.
• Production method B is a method for obtaining a compound represented by formula (3-3) containing a production intermediate of the compound of the present invention, in which the compound represented by formula (3-2) and Rb-Lv are combined with a base.
• This is a manufacturing method that includes reacting in a solvent in the presence of.
• the amount of Rb-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.
• Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.
• organic bases such as dimethylaminopyridine
• metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyl
• organic lithiums such as lithium, t-butyllithium, and hexyllithium
• metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• the amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (3-2), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-2). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl-
• solvents that are incompatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible.
• these solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-3) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-3) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-3) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• Rc represents a halogen atom
• HalR represents a halogenating agent
• R2 Ra and Rb have the same meanings as above.
• Production method C is a production method for obtaining a compound represented by formula (3-4) in which Rc represents a halogen atom, in which a compound represented by formula (3-3) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• the halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, , 3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
• the amount of halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-3), as long as the desired reaction proceeds. Preferably, the amount is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as it is 0.5 equivalent or more and the desired reaction proceeds, and is preferably 1 equivalent or more and 5 equivalents or less.
• acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid may be added. I can do it.
• the amount of acid used in this reaction is 0.01 equivalent or more with respect to the compound represented by formula (3-1), so that the desired reaction can be achieved.
• the halogenating agent used in this reaction is an iodizing agent
• the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (3-1), so that the desired reaction can be achieved.
• it is preferably 0.1 equivalent or more and 3 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (3-3). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 150°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-4) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-4) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-4) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R5a represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, which may be optionally substituted with a substituent A, or a C3 to C8 cycloalkyl group, which may be optionally substituted with a substituent B, and Q represents an oxygen atom or a sulfur atom, and R2, Ra, Rb and Rc have the same meanings as above.
• Production method D is a method for synthesizing a compound represented by formula (3-5), which comprises a compound represented by formula (3-4) and R5a-QH (where R5a has the same meaning as above). ) in a solvent in the presence of a base.
• Rc is preferably a chlorine atom, a bromine atom, or an iodine atom, more preferably a bromine atom or an iodine atom, and particularly preferably an iodine atom. be.
• R5a-QH (here, R5a and Q have the same meanings as above) used in this reaction is available as a commercial product or can be produced by a known method.
• R5a-OH is preferably methanol, ethanol, propanol, isopropanol, 2,2,2-trifluoroethanol, or 2,2,3,3,3-pentafluoropropanol, and more preferably methanol, ethanol, or 2,2,2-trifluoroethanol.
• R5a-SH is preferably methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, or butyl mercaptan, more preferably methyl mercaptan, ethyl mercaptan, or isopropyl mercaptan, and particularly preferably ethyl mercaptan.
• the amount of R5a-QH used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-4), as long as the desired reaction proceeds. Preferably, the amount is 1 equivalent or more and 20 equivalents or less.
• This reaction can be carried out by a coupling reaction using transition metals.
• the transition metals used in this reaction may have a ligand, such as palladium acetate, [1,1'-bis(diphenyl phosphino)ferrocene]palladium dichloride, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride, and the like.
• the amount of transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less relative to the compound represented by formula (3-4), but is not particularly limited as long as the desired reaction proceeds. It never happens.
• triphenylphosphine 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl, 2-di-t -Butylphosphino-2'4'6'-triisopropylbiphenyl, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and other phosphine ligands can be added.
• the amount of phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (3-4), but there are no particular limitations as long as the desired reaction proceeds. It will not be done.
• the bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate, and organic bases such as triethylamine, tributylamine, and diisopropylethylamine.
• the amount of base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-4), as long as the desired reaction proceeds, but preferably , 1 equivalent or more and 50 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but alcohol solvents such as methanol, ethanol, t-butyl alcohol, diethyl ether, diisopropyl ether, methyl- Examples include ether solvents such as t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-4). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually 30° C. or higher and 180° C. or lower or lower than the boiling point of the solvent.
• an aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
• ether solvents such as t-butyl ether
• halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride
• hydrocarbon solvents such as hexane, heptan
• solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-5) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-5) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• reaction mixture containing the compound represented by formula (3-5) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set appropriately depending on the desired purity.
• Rd represents a C1 to C6 alkyl group that may be optionally substituted with a substituent A
• R2, R5a, Q, and Rb have the same meanings as above.
• Production method E is a method for synthesizing a compound represented by formula (3-6), which involves reacting a compound represented by formula (3-5) in a solvent under acidic conditions or basic conditions. This is a manufacturing method including.
• acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular restriction as long as the desired reaction proceeds.
• the amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but preferably for the compound represented by formula (3-5). It is 0.01 equivalent or more.
• liquid acids can also be used as solvents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ethyl acetate, isopropyl acetate, and acetic acid.
• acidic solvents such as acetic acid and methanesulfonic acid
• diethyl ether diisopropyl ether
• methyl-t- Ether solvents such as butyl ether, dimethoxyethane
• Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc.
• Examples include urea-based solvents, dichloromethane, dichloroethane, chloroform, and halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-5). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 180°C or below the boiling point of the solvent.
• the base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.
• the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-5), but as long as the desired reaction proceeds, it is preferably 1 equivalent or more.
• the amount is not less than 30 equivalents and not more than 30 equivalents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• alcoholic solvents such as methanol, ethanol, isopropanol
• benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate
• nitriles such as acetonitrile amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform
• halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-5). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C or below the boiling point of the solvent.
• Post-treatment of the reaction can be carried out by a common method for reactions under acidic conditions and reactions under basic conditions.
• a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution optionally use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, etc., an alkaline aqueous solution containing dissolved potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or salt water. It can be used for.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-6) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-6) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-6) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• r represents an integer of 1 or 2
• Ox represents an oxidizing agent
• R2, R5a, Ra and Rb are as defined above.
• Production method F is a method for obtaining a compound represented by formula (3-7), which involves reacting a compound represented by formula (3-6) with an oxidizing agent (Ox) in a solvent. This is a manufacturing method including.
• oxidizing agent used in this reaction examples include peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid. It is also possible to add transition metals such as sodium tungstate.
• the amount of oxidizing agent used in this reaction is usually determined relative to the compound represented by formula (3-6). , 1.0 equivalent or more and less than 1.2 equivalents, and when producing a compound in which r is an integer of 2 in formula (3-7), it is usually 2 equivalents or more and 10 equivalents or less. Further, when adding transition metals, the amount of transition metal added is usually 0.001 equivalent or more and 1 equivalent or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, acidic solvents such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
• acidic solvents such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc.
• examples include benzene-based solvents, nitrile-based solvents such as acetonitrile, and halogen-based solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-6). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 120°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-7) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-7) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-7) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• Rd represents a C1 to C6 alkyl group that may be optionally substituted with a substituent A
• R2, R5a, Rb, and r have the same meanings as above.
• Production method G is a method for synthesizing a compound represented by formula (3-8), which involves reacting a compound represented by formula (3-7) in a solvent under acidic conditions or basic conditions. This is a manufacturing method including.
• acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular restriction as long as the desired reaction proceeds.
• the amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but it is preferably It is 0.01 equivalent or more.
• liquid acids can also be used as solvents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ethyl acetate, isopropyl acetate, and acetic acid.
• acidic solvents such as acetic acid and methanesulfonic acid
• diethyl ether diisopropyl ether
• methyl-t- Ether solvents such as butyl ether, dimethoxyethane
• Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc.
• Examples include urea-based solvents, dichloromethane, dichloroethane, chloroform, and halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-7). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 180°C or below the boiling point of the solvent.
• the base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.
• the base used in this reaction is not particularly limited as long as it is 1 equivalent or more with respect to the compound represented by formula (3-7), but as long as the desired reaction proceeds, it is preferably 1 equivalent or more.
• the amount is not less than 30 equivalents and not more than 30 equivalents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• alcoholic solvents such as methanol, ethanol, isopropanol
• benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate
• nitriles such as acetonitrile amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform
• halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-7). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C or below the boiling point of the solvent.
• Post-treatment of the reaction can be carried out by a common method for reactions under acidic conditions and reactions under basic conditions.
• a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution optionally use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, etc., an alkaline aqueous solution containing dissolved potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or salt water. It can be used for.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-8) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-8) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-8) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• Ra, R1, Rb, and Lv have the same meanings as above.
• Production method H is a method for obtaining a compound represented by formula (3-9) containing a production intermediate of the compound of the present invention, in which the compound represented by formula (3-1) and Rb-Lv are combined with a base.
• This is a manufacturing method that includes reacting in a solvent in the presence of.
• manufacturing method H can be carried out according to manufacturing method B. .
• Ra, R1, Rb, Rc and HalR have the same meanings as above.
• Production method I is a production method for obtaining a compound represented by formula (3-10) in which Rc represents a halogen atom, in which a compound represented by formula (3-9) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• manufacturing method I can be carried out according to manufacturing method C. .
• R1, R5a, Q, Ra, Rb, and Rc have the same meanings as above.
• Production method J is a method for synthesizing a compound represented by formula (3-11), comprising a compound represented by formula (3-10) and R5a-QH (where R5a and Q have the same meanings as above). ) in a solvent in the presence of a base.
• manufacturing method J can be carried out according to manufacturing method D. .
• R1, R5a, Rb, and Rd have the same meanings as above.
• Production method K is a method for synthesizing a compound represented by formula (3-13), which involves reacting a compound represented by formula (3-12) in a solvent under acidic conditions or basic conditions. This is a manufacturing method including.
• manufacturing method K can be carried out according to manufacturing method E. .
• R1, R5a, Ra, Rb, r, and Ox have the same meanings as above.
• Production method L is a method for obtaining a compound represented by formula (3-14), which involves reacting a compound represented by formula (3-11) with an oxidizing agent (Ox) in a solvent. This is a manufacturing method including.
• manufacturing method L can be carried out according to manufacturing method F. .
• R1, R5a, Rb, Rd, and r have the same meanings as above.
• Production method M is a method for synthesizing a compound represented by formula (3-16), which involves reacting a compound represented by formula (3-15) in a solvent under acidic conditions or basic conditions. This is a manufacturing method including.
• production method M can be carried out according to production method G. .
• R6 is a hydrogen atom, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, and C3 optionally substituted with substituent B.
• Production method N is a production method for obtaining a compound represented by formula (3-18) in which Rc represents a halogen atom, in which a compound represented by formula (3-17) and a halogenating agent (HalR) are combined. , is a manufacturing method that involves reacting in a solvent.
• manufacturing method N can be carried out according to manufacturing method C. .
• Re represents a halogen atom
• HalR represents a halogenating agent
• R2, R6, Rc and Rd have the same meanings as above.
• Production method O is a production method for obtaining a compound represented by formula (3-19) in which Re represents a halogen atom, in which a compound represented by formula (3-18) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• the halogenating agents used in this reaction include selectrofluor (N-fluoro-N'-triethylenediamine bis(tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, , 3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine, trimethylphenylammonium tribromide, benzyltrimethyl Examples include ammonium tribromide.
• the amount of halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-18), as long as the desired reaction proceeds. Preferably, the amount is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as it is 0.5 equivalent or more and the desired reaction proceeds, and is preferably 1 equivalent or more and 5 equivalents or less.
• acids such as inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid may be added. I can do it.
• the amount of acid used in this reaction is 0.01 equivalent or more with respect to the compound represented by formula (3-18), so that the desired reaction can be achieved.
• the halogenating agent used in this reaction is an iodizing agent
• the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (3-18), so that the desired reaction can be achieved.
• it is preferably 0.1 equivalent or more and 3 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (3-18). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 150°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (3-19) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (3-19) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (3-19) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R2, R5a, R6, Rc, and Rd have the same meanings as above.
• Production method P is a method for synthesizing a compound represented by formula (3-20), comprising a compound represented by formula (3-18) and R5a-QH (where R5a and Q have the same meanings as above). ) in a solvent in the presence of a base.
• manufacturing method P can be carried out according to manufacturing method D. .
• HalR represents a halogenating agent
• R2, R5a, Q, R6, Rd and Re have the same meanings as above.
• Production method Q is a production method for obtaining a compound represented by formula (3-21) in which Re represents a halogen atom, in which a compound represented by formula (3-20) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• manufacturing method Q can be carried out according to manufacturing method O. .
• R1, R6, Rc, Rd, and HalR have the same meanings as above.
• Production method R is a production method for obtaining a compound represented by the formula (3-23) in which Rc represents a halogen atom, in which a compound represented by the formula (3-22) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• manufacturing method R can be carried out according to manufacturing method C. .
• R1, R6, Rc, Rd, Re and HalR have the same meanings as above.
• Production method S is a production method for obtaining a compound represented by the formula (3-24) in which Re represents a halogen atom, in which a compound represented by the formula (3-23) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• manufacturing method S can be carried out according to manufacturing method O. .
• R1, R5a, Q, R6, Rc, and Rd have the same meanings as above.
• Production method T is a method for synthesizing a compound represented by formula (3-25), comprising a compound represented by formula (3-23) and R5a-QH (where R5a has the same meaning as above). ) in a solvent in the presence of a base.
• manufacturing method T can be carried out according to manufacturing method D. .
• HalR represents a halogenating agent
• R1, R5a, Q, R6, Rd, and Re are as defined above.
• Production method U is a production method for obtaining a compound represented by formula (3-26) in which Re represents a halogen atom, in which a compound represented by formula (3-25) and a halogenating agent (HalR) are combined. , a manufacturing method including reaction in a solvent.
• manufacturing method U can be carried out according to manufacturing method O. .
• R7 is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, or optionally substituted with substituent B.
• C2 to C6 haloalkynyl group C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy optionally substituted with substituent A group, or Rx4S(O)p- (where Rx4 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a substituent B as appropriate) C3 to C8 cycloalkyl group which may be substituted, C2 to C6 alkenyl group which may be optionally substituted with substituent A, C2 to C6 haloalkenyl group which may be optionally substituted with substituent A.
• R8 is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, or a C3 to C8 haloalkyl group optionally substituted with substituent B.
• Rx4S (O) represents p- (where Rx4 and p have the same meanings as above), R9 is a hydrogen atom, a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, C3 to C3 optionally substituted with substituent B C8 cycloalkyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent A, or Rx4S(O)p- (where Rx4 and p have
• Production method V is a production method for obtaining a compound represented by formula (4-2), in which a compound represented by formula (4-1) and an aminating agent (NH 2 -Lv2) are mixed in a solvent. This is a manufacturing method that involves reacting with
• Aminating agents used in this reaction include hydroxylamine-O-sulfonic acid, O-(diphenylphosphinyl)hydroxylamine, (O-(mesitylsulfonyl)hydroxylamine), O-(2,4-dinitro phenyl) hydroxylamine and the like.
• the amount of the aminating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (4-1), as long as the desired reaction proceeds. Preferably, it is 1 equivalent or more and 10 equivalents or less, and preferably 1 equivalent or more and 5 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (4-1). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 150°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (4-2) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (4-2) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (4-2) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R5 is a cyano group, a halogen atom, a C1 to C6 alkoxy group optionally substituted with a substituent A, a C1 to C6 haloalkoxy group, a C3 to C8 optionally substituted with a substituent A.
• Production method W is a production method for obtaining the compound of the present invention represented by formula (1-a), in which a compound represented by formula (4-2) and a compound represented by formula (3-27) are combined. , a manufacturing method including reaction in a solvent.
• the pyrazole carboxylic acid represented by formula (3-27) can be converted into a carboxylic acid halide and then reacted with the compound represented by formula (4-2) in the presence of a base. Further, the pyrazole carboxylic acid represented by formula (3-27) and the compound represented by formula (4-2) can be reacted in the presence of a base using a condensing agent.
• halogenating agent for synthesizing carboxylic acid halides examples include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, and the like.
• the amount of halogenating agent used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-27), as long as the desired reaction proceeds. Preferably, the amount is 1 equivalent or more and 10 equivalents or less.
• N,N-dimethylformamide can be present as a catalyst.
• the amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with respect to the compound represented by formula (3-27), but preferably 0.01 equivalent The amount is 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide Examples include amide solvents such as, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (3-27). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C or below, or below the boiling point of the solvent.
• Water can be removed from the reaction mixture containing the carboxylic acid halide obtained above using a drying agent such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the carboxylic acid halide obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the carboxylic acid halide obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• the amount of the carboxylic acid halide obtained above used in this reaction is not particularly limited as long as the desired reaction proceeds, but preferably the compound represented by formula (4-2) 1 equivalent or more and 10 equivalents or less.
• a reaction in the presence of a base will be explained.
• Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.
• organic bases such as 1,4-diazabicyclo[2.2.2]octane
• metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyllithium, t- Examples include organolithiums such as butyllithium and hexyllithium, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-27), but as long as the desired reaction proceeds, it is preferably 1 equivalent or more.
• the amount is not less than 30 equivalents and not more than 30 equivalents.
• a catalyst can be used as an activator in this reaction.
• the catalyst include 4-dimethylaminopyridine and 4-pyrrolidinopyridine.
• the amount of catalyst used in this reaction is not particularly limited as long as the desired reaction proceeds with respect to the compound represented by formula (4-2), but preferably 0.01 equivalent The amount is 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, diethyl ether, etc.
• diisopropyl ether diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane and other ether solvents
• benzene toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene and other benzene solvents
• ethyl acetate isopropyl acetate, butyl acetate, etc.
• Ester solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform , halogenated solvents such as carbon tetrachloride, and the like. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (4-2). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C or below, or below the boiling point of the solvent.
• an aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
• ether solvents such as t-butyl ether
• halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride
• hydrocarbon solvents such as hexane, heptan
• solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-a) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• reaction mixture containing the compound represented by formula (1-a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent.
• the amount of formula (3-27) used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is preferably , 1 equivalent or more and 10 equivalents or less.
• the condensing agents used in this reaction include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, N,N'-dicyclohexylcarbodiimide, Carbodiimide condensing agents such as N,N'-diisopropylcarbodiimide, imidazole dehydration condensing agents such as N,N'-carbonyldiimidazole, 1,1'-carbonyldi(1,2,4-triazole), 4-( Triazine condensing agents such as 4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexa Fluorophosphate, 1H-benzotriazol-1-yl
• the amount of condensing agent used in this reaction is not particularly limited as long as the desired reaction proceeds with respect to the compound represented by formula (3-27), but preferably 1 equivalent or more It is 10 equivalents or less.
• additives can be used together with the condensing agent.
• additives include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide, N,N'-disuccinimidyl carbonate, dimethylaminopyridine, and the like.
• the amount of the additive used in this reaction is not particularly limited as long as the desired reaction proceeds with respect to the compound represented by formula (3-27), but it is preferably 0.1 The amount is equal to or more than 10 equivalents.
• Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.
• organic bases such as 1,4-diazabicyclo[2.2.2]octane
• metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyllithium, t- Examples include organolithiums such as butyllithium and hexyllithium, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (3-27), but as long as the desired reaction proceeds, it is preferably 1 equivalent or more.
• the amount is not less than 30 equivalents and not more than 30 equivalents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide Amide solvents such as, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, triethylamine, tributylamine, diisopropylethylamine, pyridine, 2, Examples include organic base solvents such as 6-lutidine. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 1 to 200 times the weight of the compound represented by formula (3-27). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 150°C or below, or below the boiling point of the solvent.
• an aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or a saline solution. etc. can be used arbitrarily.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
• ether solvents such as t-butyl ether
• halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride
• hydrocarbon solvents such as hexane, heptan
• solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield. It is also possible to remove insoluble matter by performing a filtration operation, but this is not essential.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-a) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-a) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• G represents C-R6 or a nitrogen atom
• R6 is a hydrogen atom, a cyano group, a halogen atom, a C1 to C6 alkyl group that may be optionally substituted with a substituent A, or a C1 to C6 haloalkyl group.
• Production method This is a manufacturing method that involves reacting in a solvent.
• Rf-Lv used in this reaction can be obtained as a commercial product or produced by a known method.
• Rf-Lv may be an acid anhydride.
• the amount of Rf-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-b), and is not particularly limited as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.
• Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.
• organic bases such as dimethylaminopyridine
• metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyl
• organic lithiums such as lithium, t-butyllithium, and hexyllithium
• metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• the amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-b). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl-
• solvents that are incompatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible.
• these solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-c) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-c) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-c) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• Production method Y is a method for obtaining a compound represented by formula (1-e), which involves reacting a compound represented by formula (1-d) with an oxidizing agent (Ox) in a solvent. This is a manufacturing method including.
• manufacturing method Y can be carried out according to manufacturing method F. .
• R1, R5, R7, R8, R9, and Rb have the same meanings as above.
• Production method Z is a production method for obtaining the compound of the present invention represented by formula (1-f), in which a compound represented by formula (4-2) and a compound represented by formula (3-28) are combined. , a manufacturing method including reaction in a solvent.
• the pyrazole carboxylic acid represented by formula (3-28) can be converted into a carboxylic acid halide and then reacted with the compound represented by formula (4-2) in the presence of a base. Furthermore, the pyrazole carboxylic acid represented by formula (3-28) and the compound represented by formula (4-2) can be reacted in the presence of a base using a condensing agent.
• manufacturing method Z can be carried out according to manufacturing method W. .
• G, R1, R5, R6, R7, R8, R9, Rb, Rf, and Lv have the same meanings as above.
• Production method AA is a method for obtaining a compound represented by formula (1-h) containing the compound of the present invention, which involves reacting a compound represented by formula (1-g) with Rf-Lv in a solvent. This is a manufacturing method that includes.
• manufacturing method AA can be carried out according to manufacturing method X. .
• G, R1, R3, R4, R5a, R7, R8, R9, r, and Ox have the same meanings as above.
• Production method AB is a method for obtaining a compound represented by formula (1-j), which involves reacting a compound represented by formula (1-i) with an oxidizing agent (Ox) in a solvent. This is a manufacturing method including.
• manufacturing method AB can be carried out according to manufacturing method F. .
• Production method AC is a method for obtaining a compound represented by formula (1-l), in which a compound represented by formula (1-k) and R2a-Lv are reacted in a solvent in the presence of a base. This is a manufacturing method that includes.
• the compound represented by formula (1-k) is represented by formula (1-m) (wherein G, R3, R4, R5, R6, R7, R8, and R9 have the same meanings as above).
• the compound represented by formula (1-k) can be handled in the same manner as the compound represented by formula (1-m), and production method AC can be applied. It may be a mixture of the compound represented by formula (1-k) and the compound represented by formula (1-m), and the isomer mixing ratio may be a single one or a mixture in any ratio.
• R2a-Lv used in this reaction can be obtained as a commercially available product or produced by a known method.
• the amount of R2a-Lv used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-k), and is not particularly limited as long as the desired reaction proceeds. , preferably 1 equivalent or more and 10 equivalents or less.
• Bases used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.
• organic bases such as 1,4-diazabicyclo[2.2.2]octane
• metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyllithium, t- Examples include organic lithiums such as butyllithium and hexyllithium, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• the amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-k), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-k). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl-
• solvents that are incompatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible.
• these solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-l) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-l) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-l) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• Production method AD is a method for obtaining a compound represented by formula (1-n), in which the compound represented by formula (1-m) and R1a-Lv are reacted in a solvent in the presence of a base. This is a manufacturing method that includes.
• Production method AC by replacing the compound represented by formula (1-k) in production method AC with the compound represented by formula (1-m) and using R2a-Lv in place of R1a-Lv.
• Manufacturing method AD can be implemented.
• R2, R5, R6, R7, R8, R9, Rd, and Re have the same meanings as above.
• Production method AE is a method for obtaining a compound represented by formula (1-o), in which a compound represented by formula (4-1) and a compound represented by formula (3-27) are mixed in a solvent. This is a manufacturing method that involves reacting with
• Bases used include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, triethylamine, tributylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0 ]-7-Undecene, organic bases such as 1,4-diazabicyclo[2.2.2]octane, metal hydrides such as sodium hydride, methyllithium, butyllithium, sec-butyllithium, t-butyllithium, Examples include organic lithiums such as hexyllithium, and metal amides such as lithium diisopropylamide, lithium hexamethyldisilazane, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.
• inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride,
• the amount of base used in this reaction may be 1 equivalent or more relative to the compound represented by formula (3-27), and is not particularly limited as long as the desired reaction proceeds, but is preferably is 1 equivalent or more and 10 equivalents or less.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N,N-dimethylformamide , amide solvents such as N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (3-27). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -10°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl-
• solvents that are incompatible with water such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible.
• these solvents can be used alone or two or more kinds can be mixed in any ratio.
• the number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-o) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-o) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-o) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R2, R5a, R6, R7, R8, R9, Q, Rc, and Rd have the same meanings as above.
• Production method AF is a method for synthesizing a compound represented by formula (1-q), comprising a compound represented by formula (1-p) and R5a-QH (where R5a has the same meaning as above). ) in a solvent in the presence of a base.
• production method AF can be carried out according to production method P. .
• R2, R5, R6, R7, R8, R9, and Rd have the same meanings as above.
• Production method AG is a method for synthesizing a compound represented by formula (1-r), which is a production intermediate of the compound of the present invention, in which the compound represented by formula (1-o) is subjected to acidic conditions or basic conditions. This is a manufacturing method that involves reacting in a solvent under certain conditions.
• acids used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular restriction as long as the desired reaction proceeds.
• the amount of acid used in this reaction may be a catalytic amount and is not particularly limited as long as the desired reaction proceeds, but preferably It is 0.01 equivalent or more.
• liquid acids can also be used as solvents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ethyl acetate, isopropyl acetate, and acetic acid.
• acidic solvents such as acetic acid and methanesulfonic acid
• diethyl ether diisopropyl ether
• methyl-t- Ether solvents such as butyl ether, dimethoxyethane
• Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, etc.
• Examples include urea-based solvents, dichloromethane, dichloroethane, chloroform, and halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-o). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 180°C or below the boiling point of the solvent.
• the base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.
• the base used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-o), but as long as the desired reaction proceeds, it is preferably 1 equivalent or more.
• the amount is not less than 30 equivalents and not more than 30 equivalents.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes water, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane.
• alcoholic solvents such as methanol, ethanol, isopropanol
• benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate
• nitriles such as acetonitrile amide solvents such as N-methylpyrrolidone, N,N-dimethylformamide, N,N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, chloroform
• halogenated solvents such as carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-o). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C or below the boiling point of the solvent.
• Post-treatment of the reaction can be carried out by a common method for reactions under acidic conditions and reactions under basic conditions.
• a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution optionally use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, etc., an alkaline aqueous solution containing dissolved potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc., or salt water. It can be used for.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-r) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-r) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-r) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• the compound represented by formula (1-r) can be a useful intermediate for obtaining the compound represented by formula (1-2), which is a compound of the present invention.
• a compound represented by formula (1-2) can be obtained by subjecting the compound represented by formula (1-r) to a Curtius rearrangement reaction.
• R2, R5, R6, R7, R8, and R9 have the same meanings as above.
• Production method AH is a method for obtaining a compound represented by formula (1-s), in which a compound represented by formula (1-r) and an azide compound are reacted in a solvent in the presence of t-butanol.
• the manufacturing method includes:
• Examples of the azide compound used in this reaction include diphenylphosphoric acid azide.
• the amount of the azide compound used in this reaction is not particularly limited as long as it is 1 equivalent or more relative to the compound represented by formula (1-r), and as long as the desired reaction proceeds. , usually 1 equivalent or more and 10 equivalents or less.
• the amount of t-butanol used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-r), and is not particularly limited as long as the desired reaction proceeds. . It is also possible to use t-butanol itself as a solvent.
• the solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and toluene, xylene, benzene, chlorobenzene, and dichlorobenzene.
• alcohol solvents such as t-butanol
• ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane
• toluene xylene
• benzene chlorobenzene
• dichlorobenzene examples include benzene solvents.
• These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-r). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 150°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Addition of solvents that are incompatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. is possible. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-s) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-s) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-s) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R2, R5, R6, R7, R8 and R9 have the same meanings as above.
• Manufacturing method AI is a method for obtaining a compound represented by formula (1-t), and includes reacting a compound represented by formula (1-s) with an acid in a solvent. .
• acids used in this reaction include inorganic acids such as hydrochloric acid and hydrobromic acid, and organic acids such as methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular restriction as long as the desired reaction proceeds.
• the amount of acid used in this reaction is only a catalytic amount relative to the compound represented by formula (1-s), and is not particularly limited as long as the desired reaction proceeds; however, it is usually is 1 equivalent or more and can also be used as a solvent.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acid solvents such as hydrochloric acid and trifluoroacetic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, and dimethoxyethane. , ether solvents such as tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, esters such as ethyl acetate, isopropyl acetate and butyl acetate. and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-s). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-t) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-t) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-t) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R2, R5, R6, R7, R8, R9, Rb and Lv have the same meanings as above.
• Production method AJ is a method for obtaining a compound represented by formula (1-u), in which a compound represented by formula (1-t) and a compound represented by Rb-Lv are reacted in a solvent.
• the manufacturing method includes:
• manufacturing method AJ can be carried out according to manufacturing method B. .
• R1, R5, R6, R7, R8, R9, Rd and Re have the same meanings as above.
• Production method AK is a method for obtaining a compound represented by formula (1-v), in which a compound represented by formula (4-1) and a compound represented by formula (3-28) are mixed in a solvent. This is a manufacturing method that involves reacting with
• manufacturing method AK can be carried out according to manufacturing method AE. .
• R1, R5a, R6, R7, R8, R9, Rc, Rd, and Q have the same meanings as above.
• Production method AL is a method for synthesizing a compound represented by formula (1-x), comprising a compound represented by formula (1-w) and R5a-QH (where R5a has the same meaning as above). ) in a solvent in the presence of a base.
• manufacturing method AF can be carried out according to manufacturing method T. .
• R1, R5, R6, R7, R8, R9, and Rd have the same meanings as above.
• Production method AM is a method for synthesizing a compound represented by formula (1-y), which involves reacting a compound represented by formula (1-v) in a solvent under acidic conditions or basic conditions. This is a manufacturing method including.
• manufacturing method AM can be carried out according to manufacturing method AG.
• the compound represented by formula (1-y) can be a useful intermediate for obtaining the compound represented by formula (1-1), which is a compound of the present invention.
• a compound represented by formula (1-1) can be obtained by subjecting the compound represented by formula (1-y) to a Curtius rearrangement reaction.
• R1, R5, R6, R7, R8, and R9 have the same meanings as above.
• Production method AN is a method for obtaining a compound represented by formula (1-z), in which a compound represented by formula (1-y) and an azide compound are reacted in a solvent in the presence of t-butanol.
• the manufacturing method includes:
• Examples of the azide compound used in this reaction include diphenylphosphoric acid azide.
• the amount of the azide compound used in this reaction may be 1 equivalent or more relative to the compound represented by formula (1-y), and is not particularly limited as long as the desired reaction proceeds. , usually 1 equivalent or more and 10 equivalents or less.
• the amount of t-butanol used in this reaction is not particularly limited as long as the amount of t-butanol is 1 equivalent or more relative to the compound represented by formula (1-y), and as long as the desired reaction proceeds. .
• Tertiary butanol itself can also be used as a solvent.
• the solvents used in this reaction include alcohol solvents such as t-butanol, ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane, and toluene, xylene, benzene, chlorobenzene, and dichlorobenzene.
• alcohol solvents such as t-butanol
• ether solvents such as diisopropyl ether, methyl t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane
• toluene xylene
• benzene chlorobenzene
• dichlorobenzene examples include benzene solvents.
• These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-y). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually from 0°C to 150°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Addition of solvents that are incompatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. is possible. Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-z) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• reaction mixture containing the compound represented by formula (1-z) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-z) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R1, R5, R6, R7, R8, and R9 have the same meanings as above.
• Production method AO is a method for obtaining a compound represented by formula (1-aa), which includes reacting a compound represented by formula (1-z) with an acid in a solvent. .
• acids used in this reaction include inorganic acids such as hydrochloric acid and hydrobromic acid, and organic acids such as methanesulfonic acid, p-toluenesulfonic acid, and trifluoroacetic acid. There is no particular restriction as long as the desired reaction proceeds.
• the amount of acid used in this reaction is only a catalytic amount relative to the compound represented by formula (1-z), and is not particularly limited as long as the desired reaction proceeds; however, it is usually is 1 equivalent or more and can also be used as a solvent.
• the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but includes acid solvents such as hydrochloric acid and trifluoroacetic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, and dimethoxyethane. , ether solvents such as tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, esters such as ethyl acetate, isopropyl acetate and butyl acetate. and halogenated solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in a mixture of two or more in any ratio.
• the amount of solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but it is usually 3 times or more by weight or more and 200 times by weight relative to the compound represented by formula (1-z). It is as follows.
• the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually between -20°C and 180°C or below the boiling point of the solvent.
• aqueous solution As a post-treatment of the reaction, it is possible to perform a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture.
• an aqueous solution use an acidic aqueous solution containing hydrochloric acid, sulfuric acid, ammonium chloride, etc., an alkaline aqueous solution containing potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc., thiosulfuric acid, etc.
• An aqueous solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved, or a saline solution can be arbitrarily used.
• benzene solvents such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl- Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add Moreover, these solvents can be used alone or two or more kinds can be mixed in any ratio. The number of separations is not particularly limited and can be performed depending on the desired purity and yield.
• Water can be removed from the reaction mixture containing the compound represented by formula (1-aa) obtained above using a desiccant such as sodium sulfate or magnesium sulfate, but this is not essential.
• a desiccant such as sodium sulfate or magnesium sulfate
• reaction mixture containing the compound represented by formula (1-aa) obtained above can be subjected to solvent distillation under reduced pressure as long as the compound does not decompose.
• the reaction mixture containing the compound represented by formula (1-aa) obtained after solvent distillation can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. using an appropriate solvent. It may be set as appropriate depending on the desired purity.
• R1, R5, R6, R7, R8, R9, Rb and Lv have the same meanings as above.
• Production method AP is a method for obtaining a compound represented by formula (1-ab), in which a compound represented by formula (1-aa) and a compound represented by Rb-Lv are reacted in a solvent.
• the manufacturing method includes:
• manufacturing method AP can be carried out according to manufacturing method AJ. .
• the compound represented by formula (1-1) or formula (1-2) can be produced by arbitrarily combining production methods A to AP shown above.
• the compound represented by formula (1-1) or formula (1-2) can be produced by arbitrarily combining known methods and production methods A to AP.
• the compound of the present invention can control organisms that are harmful to plants, so it can be used as a pesticide.
• a pesticide include insecticides, fungicides, herbicides, plant growth regulators, and the like.
• insecticides fungicides, herbicides, plant growth regulators, and the like.
• it is an insecticide.
• Methods for applying the composition containing the compound of the present invention include a method in which it is brought into contact with plants or seeds, or a method in which it is contained in cultivation soil and brought into contact with roots or rhizomes of plants.
• Specific examples include foliage spraying of the composition on individual plants, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, smearing treatment on plant seeds, immersion treatment on plant seeds, and treatment on plant seeds.
• any method of application available to those skilled in the art will be sufficiently effective.
• Plants refer to those that photosynthesize and live without movement. Specific examples include rice, wheat, barley, corn, coffee, bananas, grapes, apples, pears, peaches, cherry blossoms, persimmons, citrus, soybeans, green beans, cotton, strawberries, potatoes, cabbage, lettuce, tomatoes, cucumbers, eggplants, Examples include watermelon, sugar beet, spinach, snow pea, pumpkin, sugarcane, tobacco, green pepper, sweet potato, taro, konnyaku, cotton, sunflower, rose, tulip, chrysanthemum, grass, etc., and their F1 varieties. It also includes genetically modified crops that are produced by artificially manipulating genes, etc.
• plant as used in the present invention is a general term for all parts constituting the above-mentioned individual plant, and includes, for example, stems, leaves, roots, seeds, flowers, fruits, and the like.
• seed refers to a seed that stores nutrients for seedlings to germinate and is used for agricultural propagation.
• Specific examples include seeds of corn, soybeans, cotton, rice, sugar beets, wheat, barley, sunflowers, tomatoes, cucumbers, eggplants, spinach, snow peas, pumpkins, sugarcane, tobacco, green peppers, oilseed rape, etc., and their F1 varieties.
• Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konnyaku, bulbs such as edible lilies and tulips, seed bulbs such as rakkyo, and seeds and tubers of genetically modified crops.
• the compound of the present invention has excellent effects as an active ingredient of a pest control agent or a harmful arthropod control agent, and can be used in fields, paddy fields, tea gardens, orchards, pastures, lawns, forests, gardens, street trees, etc. It can be used against harmful organisms, especially harmful arthropods, that are targeted for control in various agricultural situations.
• By applying the compound of the present invention to plant seeds it is possible to prevent damage caused by pests such as agricultural pests that occur on plants after sowing.
• the compound of the present invention exhibits a control effect against stored grain pests that damage grain stored in warehouses.
• the compound of the present invention exhibits a control effect against insects such as wood-eating pests that damage wood such as buildings, furniture, and stored wood.
• the compounds of the present invention have exterminating effects on sanitary pests that adversely affect human living environments such as houses.
• the compounds of the present invention have exterminating effects against ecto- or endoparasites of mammals and birds.
• the compounds of the present invention can control any pests such as mites, crustaceans, molluscs, and nematodes that occur and cause harm in the same situations as above.
• the compounds of the present invention are effective against pests such as insects, arthropods such as mites, crustaceans, arachnids, and centipedes, molluscs, and nematodes.
• pest names are shown below, but are not limited to these.
• Whitefly (Aleurocanthus camelliae), Whitefly (Aleurocanthus spiniferus), Whitefly (Aleurobus taonabae), Amrasca biguttulabigut tula, Aonidiella aurantii, Aphis fabae, Aphis glycines, Cotton aphid (Aphis glycines).
• Nephotettix cinctinceps Nephotettix nigropictus, Formosan leafhopper (Nephotettix virescens), Nephotettix cinctinceps zara antenna), Southern green stink bug (Nezara viridula), brown planthopper (Nilaparvata lugens), Oebalus pugnax, corn planthopper (Peregrinus maidis), black-footed planthopper (Perkinsiella saccharici) da), Phenacoccus solani, Phenacoccus solenopsis, pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera russelae), red banded stink bug (Piezodorus guildinii), white stink bug (Piezodorus hybneri), Orange mealybug (Planococcus citri), Fuji
• aciata Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, cotton leafworm (Alabama argillacea), peach caterpillar (Anarsia lineatella), velvet bean caterpillar (Anticarsia gemmatalis), archips brevi (Archips brevi) plicanus), Archips fuscocupreanus, and Archips fuscocupreanus (Archips fuscocupreanus). Argyrestia conjugella), Ascotis selenaria, Autographa nigrisigna, Bucculatrix pyrivorella, and C.
• aloptilia theivora Caloptilia zachrysa
• Carposina niponensis Carposina sasakii
• dark Hedidostem borer Chilo polychrysus
• Chilo suppressalis Choristoneura magnanima
• Cnaphalocrocis medinalis Cnaphalocrocis medinalis onogethes punctiferalis
• Ctenoplusia agnata Codling moss (Cydia pomonella)
• Diaphania indica Sugar Cane Borer (Diatraea saccharalis)
• Elasmopalpus lignosellus Grapeberry Moth (Endopiza viteana), E.
• Manacanthus stramineus chicken lice (Menopon gallinae), woolly cow lice (Solenopotes capillatus), dog lice Psocodea pests such as (Trichodectes canis); Acaphylla theavagrans, Aceria diospiri, Aceria tosichella, tulip rust mite, Aculops lycopersici, Aculops pelekassi, apple rust tick (Aculus pointedendali), and lone star tick (Aculops pelekassi).
• Thysanura pests such as Ctenolepisma villosa and Lepisma saccharina
• Araneae pests such as the redback spider (Latrodectus hasseltii); Crustacean pests such as Armadillidium vulgare, African snail (Achatina fulica), Acusta despecta sieboldiana, Euhadra peliomphala, Chacoura name Kuji (Limax Valentiana), slug (Meghimatium bilineatum), snail apple snail Gastropod pests such as (Pomacea canaliculata); Aphelenchoides besseyi, Bursaphelenchus xylophilus, Ditylenchus dipsaci, potato cyst nematode (Globodera rostoch) iensis), soybean cyst nematode (Heterodera glycines), guava root-knot nematodes
• the harmful animal is preferably a harmful arthropod, more preferably a pest of the order Storitomidae or a pest of the order Lepidoptera, and particularly preferably a brown planthopper, a green green aphid, a brown planthopper, a brown planthopper, or a brown planthopper.
• the compound of the present invention has a remarkable control effect on the above-mentioned pests that cause damage to paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc., and the occurrence of pests is predicted.
• the present invention can be applied to paddy water, foliage, or soil of paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc., depending on the season, before the outbreak of pests or when the outbreak is confirmed. It is effective as a pest control agent.
• the compound of the present invention has a remarkable controlling effect on stored grain pests and the like that occur during storage of harvested products.
• a pest control agent or harmful arthropod control agent containing the compound of the present invention as an active ingredient is sprayed, smeared, coated, dipped, coated, fumigated, or smoked onto the harvested product or the place where the harvested product is stored.
• post-harvest treatments such as pressure injection may be performed.
• a pest control agent or harmful arthropod control agent containing the compound of the present invention as an active ingredient is applied to plant seeds in an amount effective for controlling pests, either as it is, diluted with water, etc., or suspended.
• the compound of the present invention may be brought into contact with plant seeds by spraying, smearing, dipping, coating, or other treatments.
• the compound of the present invention has a remarkable control effect on wood-eating pests such as termites, Japanese wood beetles, long-eared wood beetles, white beetles, longhorn beetles, etc., and can be applied to soil or wood from buildings, etc. to control the wood-eating pests. Pests can be controlled.
• the compounds of the present invention exhibit control effects against various harmful organisms and harmful arthropods, and have the effect of protecting useful crops as well as exhibiting excellent control effects as insecticides or acaricides at low doses, so they are environmentally friendly. This has the effect of greatly contributing to reducing the load on people.
• the compound of the present invention can also be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biopesticides, etc. to exhibit excellent control effects. It is something to play.
• the compound of the present invention may be used alone, it is preferably mixed with a solid carrier, liquid carrier, gas carrier, surfactant, sticking agent, dispersant, stabilizer, etc., and is used as a powder or wettable powder. It can be used as a composition such as a wettable powder, a water-dispersible powder, a water-soluble powder, a granule, an emulsion, a liquid, a microemulsion, an aqueous suspension, an aqueous emulsion, or a suspoemulsion. The composition is not limited to these compositions as long as the effect is exhibited.
• the compound of the present invention may be used alone, it is preferably mixed with a suitable solid or liquid carrier, and optionally a surfactant, penetrating agent, spreading agent, thickener, antifreeze agent, etc.
• a surfactant penetrating agent, spreading agent, thickener, antifreeze agent, etc.
• agents, binders, anti-caking agents, disintegrants, antifoaming agents, preservatives, anti-decomposition agents, etc. it is possible to prepare liquids (soluble concentrates), emulsifiable concentrates, wettable powders, water.
• Solvent water soluble powder
• water dispersible granule water soluble granule
• suspension concentrate trate concentrated emulsion
• suspoemulsion suspoemulsion
• micro a pharmaceutical composition in any dosage form, such as an emulsion, a dustable powder, a granule, a tablet, or an emulsifiable gel.
• the preparation in any of the above dosage forms can also be provided by being enclosed in a water-soluble package such as a water-soluble capsule or a water-soluble film bag.
• the composition is not limited to these compositions as long as the effect is exhibited.
• the inert carrier that can be used in the present invention may be either solid or liquid, and examples of materials that can be used as solid inert carriers include soybean flour, grain flour, wood flour, bark flour, saw flour, Tobacco stem powder, walnut shell powder, bran, cellulose powder, residue after extracting plant extracts, synthetic polymers such as crushed synthetic resins, clays (e.g. kaolin, bentonite, acid clay, etc.), talcs (e.g. talc, pyrophyllide) etc.), silicas (e.g.
• diatomaceous earth silica sand, mica, white carbon [synthetic highly dispersed silicic acid, also known as hydrated fine powder silicon or hydrated silicic acid, and some products contain calcium silicate as a main component]), activated carbon, sulfur powder. , pumice, calcined diatomaceous earth, crushed bricks, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, and ammonium chloride, and compost. These may be used alone or in the form of a mixture of two or more.
• Materials that can be used as liquid inert carriers are selected from those that themselves have solvent ability, as well as those that do not have solvent ability but can disperse the active ingredient compound with the help of an auxiliary agent.
• Examples include the following carriers, which may be used alone or in a mixture of two or more, such as water, alcohols (such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), and ketones. (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (e.g.
• ethyl acetate, butyl acetate, propionic acid ethyl, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.
• amides eg, dimethylformamide, diethylformamide, dimethylacetamide, etc.
• nitriles eg, acetonitrile, etc.
• surfactants include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxy Ethylene fatty acid (mono- or di)ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene oxide adduct of acetylene alcohol, and alkyl Nonionic surfactants such as glycosides, alkyl sulfate ester salts, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthal
• the content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. Further, these surfactants may be used alone or in combination of two or more types.
• the application amount and application concentration of the composition containing the compound of the present invention depend on various factors, such as the purpose, target pest, crop growth status, pest outbreak tendency, weather, environmental conditions, dosage form, application method, application location, although it varies depending on the timing of application, etc., the appropriate amount of the active ingredient is generally 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm. In addition, it is generally preferable to use the active ingredient at a concentration of 1 to 300 g per 10a. Further, in the case of seed treatment, the amount of active ingredient used is 0.0001 to 1000 g per kg of seeds, preferably 0.001 to 100 g.
• composition containing the compound of the present invention When a composition containing the compound of the present invention is used as a foliar spray treatment on individual plants, a spray treatment on the soil surface, an injection treatment into the soil, or a soil irrigation treatment, it is diluted in an appropriate carrier at an appropriate concentration. After that, processing may be performed.
• a composition containing the compound of the present invention When a composition containing the compound of the present invention is brought into contact with plant seeds, the composition may be diluted to an appropriate concentration and then used by dipping, coating, spraying, or smearing on the plant seeds.
• the amount of the composition to be used when dipping, dusting, spraying or smearing is usually about 0.05 to 50%, preferably 0.1 to 30%, of the weight of dry plant seeds as the amount of active ingredients. However, it may be set as appropriate depending on the form of the composition and the type of plant seeds to be treated, and is not limited to these ranges.
• the amount of active ingredients of the compounds of the present invention represented by formulas (1-1) and (1-2) is 0.1 to 90% by weight, preferably 1 to 90% by weight, more preferably 1 to 50% by weight. %, particularly preferably from 3 to 50% by weight.
• the amount of active ingredients of the compounds of the present invention represented by formula (1-1) and formula (1-2) is usually 0.1 to 20% by weight in powder formulations, 5 to 50% by weight in emulsion formulations, and 5 to 50% by weight in hydrated formulations.
• the amount is 3 to 90% by weight for tablets, 0.1 to 20% by weight for granules, 5 to 90% by weight for flowable preparations, and 3 to 90% by weight for wettable powders.
• the amount of carrier in each dosage form is usually 60 to 99.9% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, and 80 to 99.9% by weight for granules. , and 10 to 95% by weight for flowable formulations, and 10 to 90% by weight for granule wettable powders.
• the amount of adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, and 0.1 to 20% by weight for granules.
• the amount is 0.1 to 20% by weight for flowable preparations, and 0.1 to 20% by weight for granule wettable powders.
• composition containing the compound of the present invention may optionally contain other agricultural chemicals, such as fungicides, insecticides, acaricides, nematicides, herbicides, biological pesticides, and plant growth regulators, and nucleic acid It can be used in combination with a disease control agent (International Publication No. 2014/062775), a soil conditioner, or a fertilizing substance containing as an active ingredient.
• Methods for using the compound of the present invention and other agricultural chemicals in combination include methods in which the compound of the present invention and other agricultural chemicals are formulated into one dosage form, and methods in which the compound of the invention and other agricultural chemicals are formulated into one dosage form, and both methods are used in which the compounds of the invention and other agricultural chemicals are formulated into separate dosage forms. Mix the two before use, use both at the same time in separate dosage forms, or use either one of the two in separate dosage forms. One method is to use the other after
• the ingredients contained in the insecticide are as shown in group b below, and include their salts, isomers, and N-oxides. However, known insecticides are not limited to these.
• Group b ⁇ b-1: Carbamate acetylcholinesterase (AChE) inhibitor> b-1: As a carbamate-based acetylcholinesterase (AChE) inhibitor, [b-1.1] phosphocarb, [b-1.2] alanycarb, [b-1.3] butocarboxim ( butocarboxim), [b-1.4] butoxycarboxim, [b-1.5] thiodicarb, [b-1.6] thiofanox, [b-1.7] aldicarb, [b-1.8] bendiocarb, [b-1.9] benfuracarb, [b-1.10] carbaryl, [b-1.11] Carbofuran, [b-1.12] carbosulfan, [b-1.13] ethiofencarb, [b-1.14] fenobucarb, [b-1.15] formetanate, [b-1.16] furathiocarb, [b-1.17] isopro
• ⁇ b-2 Organophosphate acetylcholinesterase (AChE) inhibitor>
• b-2 As an organophosphorus acetylcholinesterase (AChE) inhibitor, [b-2.1] acephate, [b-2.2] azamethiphos, [b-2.3] azinphos-methyl, [b-2.4] azinphos-ethyl (azinphos-ethyl), [b-2.5] ethephon, [b-2.6] cadusafos, [b-2.7] chlorethoxyfos, [b-2.8] ] chlorfenvinphos, [b-2.9] chlormephos, [b-2.10] chlorpyrifos, [b-2.11] chlorpyrifos-methyl, [ b-2.12] coumaphos, [b-2.13] cyanophos, [b-2.14] demeton-S-methyl, [b-2.15] diazinon, [b-2.16] dichlor
• ⁇ b-3 Cyclic diene organochlorine-based GABAergic chloride ion channel blocker> b-3: As a cyclic diene organochlorine GABAergic chloride ion channel blocker, [b-3.1] chlordane, [b-3.2] endosulfan, [b-3.3] Examples include lindane, [b-3.4] dienochlor, and the like.
• ⁇ b-4 Phenylpyrazole GABAergic chloride ion channel blocker>
• b-4 As a phenylpyrazole GABAergic chloride ion channel blocker, [b-4.1] ethiprole, [b-4.2] fipronil, [b-4.3] acetoprole (acetoprole), etc.
• ⁇ b-5 Sodium channel modulator> b-5: As a sodium channel modulator, [b-5.1] acrinathrin, [b-5.2] allethrin, [b-5.3] bifenthrin, [b-5.
• ⁇ b-6 Nicotinic acetylcholine receptor (nAChR) competitive modulator> b-6: As nicotinic acetylcholine receptor (nAChR) competitive modulators, [b-6.1] acetamiprid, [b-6.2] clothianidin, [b-6.3] dinotefuran ( dinotefuran), [b-6.4] imidacloprid, [b-6.5] nitenpyram, [b-6.6] thiacloprid, [b-6.7] thiamethoxam , [b-6.8] nicotine, [b-6.9] nicotine sulfate, [b-6.10] sulfoxaflor, [b-6.11] flupyradifurone , [b-6.12] triflumezopyrim, [b-6.13] flupyrimin, and the like.
• ⁇ b-7 Nicotinic acetylcholine receptor (nAChR) allosteric modulator - site I> b-7: Nicotinic acetylcholine receptor (nAChR) allosteric modulator - Site I includes [b-7.1] spinosad, [b-7.2] spinetoram, and the like.
• ⁇ b-8 Glutamatergic chloride channel (GluCl) allosteric modulator>
• b-8 Glutamatergic chloride channel (GluCl) Allosteric modulators include [b-8.1] abamectin, [b-8.2] emamectin benzoate, [b-8. 3] lepimectin, [b-8.4] milbemectin, and the like.
• ⁇ b-9 Juvenile hormone analogue> b-9: As juvenile hormone analogues, [b-9.1] hydroprene, [b-9.2] kinoprene, [b-9.3] methoprene, [b- 9.4] phenoxycarb, [b-9.5] pyriproxyfen, and the like.
• non-specific (multisite) inhibitors include [b-10.1] methyl bromide, [b-10.2] chloropicrin, [b-10.3] ] Cryolite, [b-10.4] sulfuryl fluoride, [b-10.5] borax, [b-10.6] boric acid, [ b-10.7] disodium octaborate, [b-10.8] sodium metaborate, [b-10.9] tartarite, [b-10.10] Examples include dazomet, [b-10.11] metam, and [b-10.12] carbam sodium salt.
• Chord tone organ TRPV channel modulator includes [b-11.1] pymetrozine, [b-11.2] pyrifluquinazone, [b-11.3] afidopyropen, etc. .
• ⁇ b-12 Mite growth inhibitor acting on CHS1>
• b-12 As mite growth inhibitors that act on CHS1, [b-12.1] clofentezine, [b-12.2] diflobidazin, [b-12.3] hexythiazox ( hexythiazox), [b-12.4]ethoxazole, and the like.
• ⁇ b-13 Microbial-derived insect midgut membrane disrupting agent>
• b-13 As a microorganism-derived insect midgut membrane disrupting agent, [b-13.1] Bacillus thuringiensis, [b-13.2] B. t. israelensis (B.t. subsp. Israelensis), [b-13.3]B. t. Aizawai (B.t. subsp. Aizawai), [b-13.4] B. t. Kurstaki (B.t. subsp. kurstaki), [b-13.5]B. t. B.t. subsp.
• Proteins contained in Bt crops Cry1Ab, Cry1Ac, Cry1Fa, Cry1A. 105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry 3Bb, Cry34Ab1/Cry35Ab1 (B.t. crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2A b, Vip3A, mCry3A, Cry3Ab, Cry 3Bb, Cry34Ab1/Cry35Ab1), [b-13.7] Bacillus sphaericus and the like.
• ⁇ b-14 Mitochondrial ATP synthase inhibitor>
• b-14 As mitochondrial ATP synthase inhibitors, [b-14.1] diafenthiuron, [b-14.2] azocyclotin, [b-14.3] cyhexatin , [b-14.4] fenbutatin oxide, [b-14.5] propargite, [b-14.6] tetradifon, and the like.
• ⁇ b-15 Oxidative phosphorylation uncoupler that disrupts proton gradient> b-15: As an oxidative phosphorylation uncoupler that disrupts the proton gradient, [b-15.1] chlorfenapyl, [b-15.2] DNOC (dinitro-ortho-cresol), [b-15.3] binapacryl, [b-15.4] sulfuramide ),
• ⁇ b-16 Nicotinic acetylcholine receptor (nAChR) channel blocker> b-16: As nicotinic acetylcholine receptor (nAChR) channel blockers, [b-16.1] bensultap, [b-16.2] cartap hydrochloride, [b-16.3] Examples include thiocyclam, [b-16.4] thiosultap, [b-16.5] thiosultap sodium salt, [b-16.6] monosultap, etc. .
• ⁇ b-17 Chitin biosynthesis inhibitor acting on CHS1>
• b-17 As chitin biosynthesis inhibitors that act on CHS1, [b-17.1] bistrifluron, [b-17.2] chlorfluazuron, [b-17.3] ] diflubenzuron, [b-17.4] flucycloxuron, [b-17.5] flufenoxuron, [b-17.6] hexaflumuron, [ b-17.7] lufenuron, [b-17.8] novaluron, [b-17.9] noviflumuron, [b-17.10] teflubenzuron, [b- 17.11] triflumuron, and the like.
• b-18 Chitin biosynthesis inhibitor type 1> b-18: Chitin biosynthesis inhibitor type 1 includes [b-18.1] buprofezin and the like.
• ⁇ b-19 Inhibitor of molting of insects of the order Hyridae>
• b-19 Examples of insect molting inhibitors of the order Hymenoptera include [b-19.1] cyromazine and the like.
• Octopamine receptor agonist includes [b-21.1] amitraz and the like.
• ⁇ b-22 Mitochondrial electron transport chain complex III inhibitor>
• b-22 As mitochondrial electron transport chain complex III inhibitors, [b-22.1] hydramethylnon, [b-22.2] acequinocyl, [b-22.3] fluacrypyrim ( fluacrypyrim), [b-22.4]bifenazate, and the like.
• ⁇ b-23 Mitochondrial electron transport chain complex I inhibitor (METI)>
• b-23 Mitochondrial electron transport chain complex I inhibitor (METI): [b-23.1] fenazaquin, [b-23.2] fenpyroximate, [b-23.3] pyridaben (pyridaben), [b-23.4] pyrimidifen, [b-23.5] tebufenpyrad, [b-23.6] tolfenpyrad, [b-23.7] rotenone ) etc.
• b-24 Voltage-dependent sodium channel blocker>
• Voltage-dependent sodium channel blockers include [b-24.1] indoxacarb, [b-24.2] metaflumizone, and the like.
• ⁇ b-25 Acetyl-CoA carboxylase inhibitor>
• b-25 As an acetyl-CoA carboxylase inhibitor, [b-25.1] spirodiclofen, [b-25.2] spiromesifen, [b-25.3] spiropidion , [b-25.4] spirotetramat, and the like.
• ⁇ b-26 Mitochondrial electron transport chain complex IV inhibitor>
• b-26 As a mitochondrial electron transport chain complex IV inhibitor, [b-26.1] aluminum phosphide, [b-26.2] calcium phosphide, [b-26. 3] Hydrogen phosphine, [b-26.4] zinc phosphide, [b-26.5] calcium cyanide, [b-26.6] potassium cyanide ), [b-26.7] sodium cyanide, and the like.
• ⁇ b-27 Mitochondrial electron transport chain complex II inhibitor>
• b-27 Mitochondrial electron transport chain complex II inhibitors: [b-27.1] cyenopyrafen, [b-27.2] cyflumetofen, [b-27.3] pyflubumide etc.
• ⁇ b-28 Ryanodine receptor modulator>
• b-28 As a ryanodine receptor modulator, [b-28.1] chlorantraniliprole, [b-28.2] cyantraniliprole, [b-28.3] flubendiamide (flubendiamide), [b-28.4] cyclaniliprole, [b-28.5] tetraniliprole, and the like.
• ⁇ b-29 Chord tone organ modulator target site unidentified> b-29: chordotonal organ modulator Examples of insecticides with unspecified target sites include [b-29.1] flonicamid and the like.
• GABAergic chloride ion channel allosteric modulator > b-30: GABAergic chloride ion channel allosteric modulators include [b-30.1] broflanilide, [b-30.2] fluxametamide, and the like.
• ⁇ b-31 Baculovirus> b-31: As baculoviruses, [b-31.1] Cydia pomonella GV (Cydia pomonella GV), [b-31.2] Thaumatotibia leucotreta GV (Thaumatotibia leucotreta GV), [b-31.3] Anticarsia gemmatalis MNPV, [b-31.4] Helicoverpa armigera NPV PV), etc.
• nAChR Nicotinic acetylcholine receptor
• nAChR Nicotinic acetylcholine receptor
• b-33 Other insecticides> b-33: Other insecticides include [b-33.1] azadirachtin, [b-33.2] benzoximate, [b-33.3] phenisobromolate. , [b-33.4] chinomethionat, [b-33.5] dicofol, [b-33.6] lime sulfur mixture (CaSx), [b-33.7] manzeb ), [b-33.8] pyridalyl, [b-33.9] sulfur, [b-33.10] bromopropylate, [b-33.11] Burkholderia Genus Bacterium Burkholderia spp, Wolbachia pipientis (Zap), [b-33.12] Chenopodium ambrosioides near ambrosioides extract), [b-33.13] containing glycerin or propanediol.
• ENT-8184 N-(2-Ethylhexyl)bicyclohept-5-ene-2,3-dicarboximide
• Bayer 22408 O, O-diethyl O-naphthalimido phosp horothioate
• Bayer 32394 tris(1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrate
• flometoquin [b -33.110] dichloromezothiaz
• the components contained in the disinfectant are as shown in group c below, and include their salts, isomers, and N-oxides. However, known disinfectants are not limited to these.
• Group c ⁇ c-1: Phenylamide fungicide> c-1: As a phenylamide fungicide, [c-1.1] benalaxyl, [c-1.2] benalaxyl M or kiralaxyl, [c-1.3] furaraxyl (furaxyl), [c-1.4] metalaxyl, [c-1.5] metalaxyl-M or mefenoxam, [c-1.6] oxadixyl, [c- 1.7] ofurace and the like.
• ⁇ c-2 Hydroxy(2-amino)pyrimidine fungicide> c-2: As a hydroxy(2-amino)pyrimidine fungicide, [c-2.1] bupirimate, [c-2.2] dimethylimol, [c-2.3] ethirimol ) etc.
• ⁇ c-4 Carboxylic acid disinfectant>
• c-4 Examples of carboxylic acid fungicides include [c-4.1] octilinone and the like.
• ⁇ c-5 ⁇ -tubulin polymerization inhibitor>
• c-5 As a ⁇ -tubulin polymerization inhibitor, [c-5.1] benomyl, [c-5.2] carbendazim, [c-5.3] fuberidazole, [c-5.4] thiabendazole, [c-5.5] thiophanate, [c-5.6] thiophanate-methyl, [c-5.7] diethofencarb, Examples include [c-5.8] zoxamide, [c-5.9] ethaboxam, and the like.
• ⁇ c-6 Cell division inhibitor>
• c-6 Cell division inhibitors include [c-6.1] pencycuron and the like.
• c-7 Delocalization of spectrin-like protein
• c-7 As a bactericidal agent related to delocalization of spectrin-like protein, [c-7.1] fluopicolide, [c-7.2 ] fluopimomide and the like.
• c-8 Actin/Myosin/Fimbrin function
• c-8 As bactericidal agents related to actin/myosin/fimbrin function, [c-8.1] Phenamacril, [c-8.2] Metrafenone ), [c-8.3]pyriophenone, and the like.
• ⁇ c-9 Complex I: NADH oxidoreductase inhibitor>
• c-9 Complex I: NADH oxidoreductase inhibitors include [c-9.1] diflumetrim, [c-9.2] tolfenpyrad, [c-9.3] fenazaquin. ) etc.
• SDHI agent succinate dehydrogenase inhibitor
• SDHI agents include [c-10.1] benodanil, [c-10.2] benzobindiflupyr, [c-10.3] ] Bixafen, [c-10.4] boscalid, [c-10.5] carboxin, [c-10.6] fenfuram, [c-10.7] fluopyram, [c-10.8] flutolanil, [c-10.9] fluxapyroxad, [c-10.10] furametpyr, [c-10.11] ] isofetamide, [c-10.12] isopyrazam, [c-10.13] mepronil, [c-10.14] oxycarboxin, [c-10.15] ] penthiopyrad, [c-10.16] penflufen, [c-10.17] pydiflumetofen, [c-10.18] sedaxane
• ⁇ c-11 QoI agent (quinone external inhibitor)> c-11: As a QoI agent (quinone external inhibitor), [c-11.1] azoxystrobin, [c-11.2] coumoxystrobin, [c-11.3] ] dimoxystrobin, [c-11.4] enoxastrobin, [c-11.5] famoxadone, [c-11.6] fenamidone, [c -11.7] phenaminstrobin, [c-11.8] flufenoxystrobin, [c-11.9] fluoxastrobin, [c-11.10] cresoxime methyl (kresoxim-methyl), [c-11.11] mandestrobin, [c-11.12] metominostrobin, [c-11.13] orysastrobin, [c-11] .14] picoxystrobin, [c-11.15] pyraclostrobin, [c-11.16] pyrametostrobin, [c-11.17] pyroxystrobin (
• ⁇ c-12 QiI agent (quinone internal inhibitor)> c-12: As a QiI agent (quinone internal inhibitor), [c-12.1] amisulbrom, [c-12.2] cyazofamid, [c-12.3] fenpicoxamide ( fenpicoxamide) and the like.
• ⁇ c-13 Oxidative phosphorylation uncoupling inhibitor> c-13: As oxidative phosphorylation uncoupling inhibitors, [c-13.1] binapacryl, [c-13.2] meptyldinocap, [c-13.3] dinocap ( dinocap), [c-13.4] fluazinam, [c-13.5] ferimzone, and the like.
• ⁇ c-14 ATP synthase inhibitor>
• c-14 As an ATP synthase inhibitor, [c-14.1] triphenyltin acetate (fentin acetate), [c-14.2] triphenyltin chloride (fentin chloride), [c-14.3] Examples include triphenyltin hydroxide (fentin hydroxide).
• ⁇ c-15 ATP transport>
• bactericidal agents related to c-15 include [c-15.1] silthiofam.
• ⁇ c-16 QoSI agent (quinone external stigmatellin binding subsite inhibitor)> c-16: QoSI agents (quinone external stigmatellin binding subsite inhibitors) include [c-16.1] ametoctradin and the like.
• Methionine biosynthesis inhibitors include [c-17.1] cyprodinil, [c-17.2] mepanipyrim, [c-17.3] pyrimethanil, etc. .
• ⁇ c-18 Protein biosynthesis inhibitor>
• c-18 As protein biosynthesis inhibitors, [c-18.1] blasticidin-S, [c-18.2] kasugamycin, [c-18.3] streptomycin ), [c-18.4]oxytetracycline, and the like.
• ⁇ c-19 Signal transduction inhibitor>
• c-19 As signal transduction inhibitors, [c-19.1] quinoxyfen, [c-19.2] proquinazid, [c-19.3] fenpiclonil, [c-19] .4] fludioxonil, [c-19.5] chlozolinate, [c-19.6] dimethachlone, [c-19.7] iprodione, [c-19.8] ]procymidone, [c-19.9]vinclozolin, and the like.
• ⁇ c-20 Lipid and cell membrane biosynthesis inhibitor>
• c-20 As a lipid and cell membrane biosynthesis inhibitor, [c-20.1] edifenphos, [c-20.2] iprobenfos, [c-20.3] isoprothiolane, [c-20.4] pyrazophos, [c -20.5] biphenyl, [c-20.6] chloroneb, [c-20.7] dichloran, [c-20.8] quintozene, [c-20 .9] tecnazene, [c-20.10] tolclofos-methyl, [c-20.11] echlomezol or etridiazole, [c-20.12] iodocarb, [ c-20.13] propamocarb, [c-20.14] prothiocarb, and the like.
• ⁇ c-21 Cell membrane disruptor>
• c-21 As a fungicide related to a cell membrane disruptor, [c-21.1] extract from Melaleuca alternifolia, [c-21.2] vegetable oil (mixture) eugenol , geraniol, thymol (plant oils (mixtures): eugenol, geraniol, thymol), and the like.
• ⁇ c-22 Ergosterol binder>
• c-22 As a bactericidal agent related to ergosterol binding, [c-22.1] natamycin and the like can be mentioned.
• ⁇ c-25 Amine fungicide> c-25: As amine fungicides, [c-25.1] aldimorph, [c-25.2] dodemorph, [c-25.3] fenpropimorph, [c -25.4] tridemorph, [c-25.5] fenpropidin, [c-25.6] piperalin, [c-25.7] spiroxamine, etc. It will be done.
• ⁇ c-26 3-keto reductase inhibitor in C4-position demethylation of sterol biosynthesis> c-26: As 3-keto reductase inhibitors for C4 demethylation in sterol biosynthesis, [c-26.1] fenhexamide, [c-26.2] fenpyrazamine, etc. Can be mentioned.
• ⁇ c-27 Squalene epoxidase inhibitor of sterol biosynthesis> c-27: As squalene epoxidase inhibitors of sterol biosynthesis, [c-27.1] pyributicarb, [c-27.2] naftifine, [c-27.3] terbinafine etc.
• ⁇ c-28 Cell wall biosynthesis inhibitor>
• c-28 As a cell wall biosynthesis inhibitor, [c-28.1] polyoxins, [c-28.2] dimethomorph, [c-28.3] flumorph, [c -28.4] pyrimorph, [c-28.5] benthiavalicarb, [c-28.6] benthivalicarb-isopropyl, [c-28.7] Examples include iprovalicarb, [c-28.8] mandipropamide, [c-28.9] valifenalate, and the like.
• ⁇ c-29 Melanin biosynthesis inhibitor>
• c-29 As melanin biosynthesis inhibitors, [c-29.1] phthalide or fthalide, [c-29.2] pyroquilone, [c-29.3] tricyclazole, [ c-29.4] carpropamid, [c-29.5] diclocymet, [c-29.6] fenoxanil, [c-29.7] tolprocarb, etc. .
• ⁇ c-30 Host plant resistance inducer> c-30: As a host plant resistance inducer, [c-30.1] acibenzolar-S-methyl, [c-30.2] probenazole, [c-30.3] thiazinyl (tiadinil), [c-30.4] isotianil, [c-30.5] laminarin, [c-30.6] extract from Reynoutria sachalinensis (giant knotwe) ed) ), [ c-30.7] Bacillus mycoides isolate J, [c-30.8] cell walls of Saccharomyces cerevisiae strain LAS117 LAS117), [c-30.9] fosetyl, [c-30.10] phosphorous acid, [c-30.11] sodium phosphorous acid, [c-30.12] ammonium phosphorous acid Examples include ammonium phosphite, [c-30.13] potassium salt of phosphorous acid, and the like.
• ⁇ c-31 Dithiocarbamate fungicide> c-31: As a dithiocarbamate fungicide, [c-31.1] mancozeb, [c-31.2] manzeb, [c-31.3] maneb, [c- 31.4] metiram, [c-31.5] propineb, [c-31.6] thiram, [c-31.7] zinc thiazole, [c- Examples include 31.8] zineb, [c-31.9] ziram, and [c-31.10] ferbam.
• ⁇ c-32 Phthalimide fungicide>
• c-32 As a phthalimide fungicide, [c-32.1] captan, [c-32.2] captafol, [c-32.3] folpet, [c -32.4] fluorofolpet and the like.
• ⁇ c-33 Guanidine-based fungicide> c-33: As a guanidine fungicide, [c-33.1] guazatine, [c-33.2] iminoctadine, [c-33.3] iminoctadine albesilate , [c-33.4] iminoctadine triacetate, and the like.
• ⁇ c-34 Multi-point contact active fungicide>
• c-34 As a multi-point contact active fungicide, [c-34.1] chlorothalonil, [c-34.2] dichlofluanid, [c-34.3] tolylfluanid (tolylfluanid), [c-34.4] basic copper oxychloride, [c-34.5] copper II hydroxide, [c-34.6] basic copper sulfate ( copper hydroxide sulfate), [c-34.7] organocopper compound, [c-34.8] dodecylbenzenesulfonic acid bisethylenediamine copper complex [II] dodecylbenzenesulfonic acid b isethylenediamine copper [II] salt), [c -34.9] sulfur, [c-34.10] fluoroimide, [c-34.11] anilazine, [c-34.12] dithianon, [c-34] .13] chinomethionate or quinometh
• ⁇ c-35 Biological pesticide with multiple mechanisms of action>
• c-35 As biopesticides with multiple mechanisms of action, [c-35.1] Extract from the cotyledons of Black bean seedlings (BLAD), [c-35.2] Extract from Swinglea glutinosa (Extract from Swinglea glutinosa), [c-35.3] Trichoderma atroviride strain I-1237, [c-35.4] Trichoderma atroviride strain LU132 e strain LU132), [c-35.
• Trichoderma atroviride strain SC1 [c-35.6] Trichoderma asperellum strain T34, [c-35.7] Gliocladi Gliocladium strain J1446 (Gliocladium catenulatum strain J1446), [c-35.8] Clonostachys rosea strain CR-7, [c-35.9] Bacillus amyloliquefaciens QST713 strain oliquefaciens strain QST713) , [c-35.10] Bacillus amyloliquefaciens strain FZB24, [c-35.11] Bacillus amyloliquefaciens MBI600 strain quefaciens strain MBI600), [c-35.
• c-36 Other fungicides> c-36: Other fungicides include [c-36.1] tecloftalam, [c-36.2] triazoxide, [c-36.3] flusulfamide, [c-36] .4] diclomezine, [c-36.5] cyflufenamide, [c-36.6] dodine, [c-36.7] flutianil, [c-36.8] ] tebufloquin, [c-36.9] validamycins, [c-36.10] cymoxanil, [c-36.11] picarbutrazox, [c-36] .12] quinofumelin, [c-36.13] aminopyrifen, [c-36.14] pyridachlomethyl, [c-36.15] ipflufenoquin , [c-36.16] florylpicoxamide, [c-36.17] dichlobentiazox, [c-
• the mixing ratio of the compound of the present invention and other insecticides or fungicides in a mixture of the compound of the present invention and other insecticides or fungicides is not particularly limited, but for example, the compound of the present invention: other insecticide or fungicide is 0.01:100-100:0.01, 0.1:100-100:0.1, 1:100-100:1, 1:10-10:1, or 1:1 (all by weight) conversion). Furthermore, the range of any combination of these upper and lower limits is also included as a mixing ratio. When there are two or more types of other insecticides and fungicides, the above mixing ratio refers to the total ratio of the other insecticides and fungicides to the compound of the present invention.
• the compound of the present invention has a remarkable exterminating effect on sanitary pests such as Diptera pests (culex mosquitoes, common pediculose mosquitoes, chironomid mosquitoes, houseflies, butterflies, cowfly, etc.) and Apiptera pests (german cockroaches, black cockroaches, American cockroaches, etc.) It is something.
• the compound of the present invention can be used as an anthelmintic for arthropods that cause direct harm or are vectors of disease, and can be used as an oil solution or as an anthelmintic for the surrounding environment where these pests may be latent.
• brown moths, etc. which are agricultural and forest pests, in the same way as the method described above, and flies, etc., can be controlled by controlling them by mixing them in livestock feed and droppings.
• mosquitoes it is also effective to volatilize it into the air using an electric mosquito repellent.
• the preparations in these usage forms can also be present as a mixture with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists;
• the formulations suitably contain a total amount of the compounds of the invention, for example from 0.0001% to 95% by weight.
• the compounds of the present invention can exterminate external or internal parasites of non-human mammals and birds, such as domestic animals and pets, such as cat fleas, dog fleas, Ixodes ticks, and nematodes of the family Filaridae.
• Extermination of external and internal parasites is achieved by oral, parenteral or transdermal administration.
• a small amount of the compound of the present invention may be mixed into food or feed, or an orally administered preparation such as an appropriate orally ingestible pharmaceutical composition, such as a pharmaceutically acceptable carrier or coating material, may be used.
• the medicated drinking water When administered orally as a medicated drinking water, the medicated drinking water is usually dissolved, suspended or dissolved in a suitable non-toxic solvent or water with a suspending or wetting agent such as bentonite or other excipients. It may be prepared as a dispersion. Additionally, medicated drinking water generally further contains an antifoaming agent. Medicinal drinking water can generally contain 0.01% to 1.0% by weight, preferably 0.01% to 0.1% by weight of the compound of the present invention.
• capsules, pills or tablets containing a predetermined amount of the active ingredient are usually employed.
• These use forms are prepared by homogeneously mixing the active ingredient with suitably finely divided diluents, fillers, disintegrants and/or binders such as starch, lactose, talc, magnesium stearate, vegetable gums, etc. Manufactured.
• Such dry solid unit use formulations can vary widely in weight and content of anthelmintic agent depending on the type of host animal being treated, the degree of infection and type of parasite, and the weight of the host.
• When administered via animal feed it can be homogeneously dispersed in the feed, used as a top dressing or in the form of pellets.
• the compounds of the invention are present in the final feed, for example from 0.0001% to 0.05% by weight, preferably from 0.0005% to 0.01% by weight. It is also possible to contain.
• transdermal administration it may be administered transdermally or locally as a transdermal preparation such as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, or the like.
• Transdermal and topical methods of administration also include devices attached to the animal (eg, collars, medallions, ear tags, etc.) to locally or systemically control arthropods.
• the compound of the present invention is generally used in an amount of 0.0001% to 0.1% by weight, preferably 0.001% to 0.01% by weight. All you have to do is administer it.
• a liquid carrier excipient can be administered to animals parenterally by intragastric, intramuscular, intratracheal, or subcutaneous injection.
• the active compound is preferably mixed with a suitable vegetable oil, such as peanut oil, cottonseed oil.
• suitable vegetable oil such as peanut oil, cottonseed oil.
• Such formulations may generally contain from 0.05% to 50% by weight, preferably from 0.1% to 5.0% by weight of a compound of the invention. They may also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct injection.

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• 2023
  • 2023-03-10 WO PCT/JP2023/009209 patent/WO2023171783A1/ja not_active Ceased
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