Amide compound and noxious arthropod control composition containing same

Abstract

The present invention provides a compound having an excellent controlling efficacy against harmful arthropods. (In the formula, R1 represents a C1-C6 chain hydrocarbon group or the like, R2, R3, R5, R6 and R7 may be the same or different from each other and represent a hydrogen atom or the like, R4 represents a C1-C6 chain hydrocarbon group or the like, R8 and R9 may be the same or different from each other and represent a hydrogen atom or the like, m represents 0, 1, 2 or 3, n represents 1, 2, 3 or 4, R10 represents a hydrogen atom or the like, Y represents a single bond, an oxygen atom or-S (O) u-, in the case where Y is a single bond, p represents 0, Q represents a C1-C8 chain hydrocarbon group or the like, and n represents a hydrogen atom or the like. When Y is an oxygen atom or-S (O) u-, p represents 0, 1, 2, 3, 4, 5, 6 or 7, Q represents a C1-C8 chain hydrocarbon group or the like, u represents 0, 1 or 2, and R11 and R12 are the same or different from each other and represent a hydrogen atom or the like. ) The compound represented by formula (1) or a salt thereof has an excellent controlling effect on harmful arthropods. # imgabs0 #

Description

Technical Field

[0001] This patent application claims priority and benefits under the Paris Convention based on Japanese Patent Application No. 2023-000414 (filed on January 5, 2023), and all the contents described in the above application are incorporated into this specification by reference herein.

[0002] The present invention relates to an amide compound and a pest arthropod control composition containing the amide compound. Background Art

[0003] So far, various compounds have been studied for the purpose of controlling pest arthropods. For example, Patent Document 1 describes that a certain compound has a pest control effect.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: WO 2014 / 119696 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] The problem of the present invention is to provide a compound having excellent control efficacy against pest arthropods.

[0009] Means for Solving the Problems

[0010] The present invention is as follows.

[0011] 〔1〕A compound represented by formula (I) (hereinafter referred to as Compound N of the present invention) or a salt thereof (hereinafter, Compound N of the present invention or a salt thereof is referred to as the compound of the present invention).

[0012]

[0013] 〔In the formula,

[0014] R 1 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, a C1-C3 alkylcarbonyl group which may have one or more halogen atoms, a C1-C3 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C3 alkylsulfonyl group which may have one or more halogen atoms, or a hydrogen atom,

[0015] R 2 , R 3 , R 5 , R 6 and R 7are the same as or different from each other, and represent a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, a C1-C3 alkoxy group which may have one or more halogen atoms, or a hydrogen atom.

[0016] R 4 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a C1-C3 alkoxy group which may have one or more halogen atoms.

[0017] R 8 and R 9 are the same as or different from each other, and represent a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, a phenyl group, a pyridyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group {the phenyl group, the pyridyl group, the furyl group, the tetrahydrofuryl group, the thienyl group, the tetrahydrothienyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group may have one or more substituents selected from Group B}, or a hydrogen atom.

[0018] m represents 0, 1, 2 or 3.

[0019] When m is 2 or 3, the two or three Rs 2 and R 3 may each independently be the same as or different from each other.

[0020] n represents 1, 2, 3 or 4.

[0021] When n is 2, 3 or 4, the two, three or four Rs 6 and R 7 may each independently be the same as or different from each other.

[0022] R 2 and R 3 may together form -(CR 13 R 14 )-(CR 15 R 16 ) a -(CR 17 R 18 )- or -(CR 19 R 20 ) b -Z 1 -(CR 21 R 22 ) c -.

[0023] R4 and R 5 can together form -(CR 23 R 24 )-(CR 25 R 26 ) d -(CR 27 R 28 )-、or -(CR 29 R 30 ) e -Z 2 -(CR 31 R 32 ) f -,

[0024] R 6 and R 7 can together form -(CR 33 R 34 )-(CR 35 R 36 ) g -(CR 37 R 38 )-、or -(CR 39 R 40 ) h -Z 3 -(CR 41 R 42 ) i -,

[0025] R 8 and R 9 can together form -(CR 43 R 44 )-(CR 45 R 46 ) j -(CR 47 R 48 )-、or -(CR 49 R 50 ) k -Z 4 -(CR 51 R 52 ) r -,

[0026] a, d, g and j each independently represent 0, 1, 2 or 3,

[0027] b, c, e, f, h, i, k and r each independently represent 1 or 2,

[0028] Z 1 、Z 2 、Z 3 and Z 4Identical to or different from each other, and represent an oxygen atom, a sulfur atom or NR 53 ,

[0029] R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 、R 42 、R 43 、R 44 、R 45 、R 46 、R 47 、R 48 、R 49 、R 50 、R 51 、R 52 and R 53 Identical to or different from each other, and represent a C1-C4 alkyl group which may have one or more halogen atoms, or a hydrogen atom

[0030] When a, d, g or j is 2 or 3, two or three Rs 15 、R 16 、R 25 、R 26 、R 35 、R 36 、R 45 and R 46 may each independently be identical to or different from each other

[0031] When b, c, e, f, h, i, k or r is 2, two Rs 19 、R 20 、R 21 、R 22 、R29 , R 30 , R 31 , R 32 , R 39 , R 40 , R 41 , R 42 , R 49 , R 50 , R 51 and R 52 each independently may be the same or different,

[0032] multiple Rs 53 each independently may be the same or different,

[0033] R 10 represents a C1-C3 chain hydrocarbon group that may have one or more substituents selected from group D, a C1-C4 alkoxycarbonyl group that may have one or more halogen atoms, a cyano group, a formyl group, a carboxyl group, a carbamoyl group, a halogen atom, or a hydrogen atom,

[0034] Y represents a single bond, an oxygen atom, or -S(O) u -,

[0035] When Y is a single bond, p represents 0, and Q represents a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group F, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group H, or a hydrogen atom,

[0036] When Y is an oxygen atom or -S(O) u -, p represents 0, 1, 2, 3, 4, 5, 6, or 7, and Q represents a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group H, or a group selected from group G,

[0037] u represents 0, 1, or 2,

[0038] R 11 and R 12 are the same as or different from each other, and represent a C1-C4 alkyl group that may have one or more halogen atoms, a halogen atom, or a hydrogen atom,

[0039] When p is 1, 2, 3, 4, 5, 6, or 7, 1, 2, 3, 4, 5, 6, or 7 Rs 11 and R 12 each independently may be the same or different.

[0040] Group A: A C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group E, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylcarbonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, phenyl, pyridyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl {the phenyl, the pyridyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the pyridazinyl, the pyrimidinyl and the pyrazinyl may have one or more substituents selected from Group B}, a halogen atom, a hydroxyl group, a cyano group and CONR 54 R 55 constituted group.

[0041] R 54 and R 55 are the same or different from each other, and represent a C1-C4 alkyl group which may have one or more halogen atoms, or a hydrogen atom.

[0042] Group B: A C1-C4 chain hydrocarbon group which may have one or more halogen atoms, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylthio group which may have one or more halogen atoms, a C1-C4 alkylsulfinyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, phenyl which may have one or more halogen atoms, phenoxy which may have one or more halogen atoms, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a halogen atom and CONR 54 R 55 constituted group.

[0043] Group C: consisting of a C1-C4 chain hydrocarbon group which may have one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group E, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylcarbonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, phenyl, pyridyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl {the phenyl, the pyridyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the pyridazinyl, the pyrimidinyl and the pyrazinyl may have one or more substituents selected from Group B}, halogen atom, hydroxyl group, cyano group and CONR 54 R 55 comprising the group.

[0044] Group D: consisting of a hydroxyl group and a halogen atom.

[0045] Group E: consisting of a C1-C4 alkoxy group which may have one or more halogen atoms, a cyano group, a hydroxyl group and a halogen atom.

[0046] Group F: consisting of a C3-C8 alicyclic hydrocarbon group, indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, pyridyl, quinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuryl, benzothienyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl {the C3-C8 alicyclic hydrocarbon group, the indanyl, the 1,2,3,4-tetrahydronaphthyl, the phenyl, the naphthyl, the pyridyl, the quinolinyl, the pyridazinyl, the pyrimidinyl, the pyrazinyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the benzofuryl, the benzothienyl, the 1,3-benzodioxolyl and the 1,4-benzodioxanyl may have one or more substituents selected from Group C}, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group and CONR 54 R 55 comprising the group.

[0047] Group G: A group consisting of a C3-C8 alicyclic hydrocarbon group, an indanyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a naphthyl group, a pyridyl group, a quinolinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a furyl group, a thienyl group, a pyrrolidinyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuryl group, and a benzothienyl group {the C3-C8 alicyclic hydrocarbon group, the indanyl group, the 1,2,3,4-tetrahydronaphthyl group, the phenyl group, the naphthyl group, the pyridyl group, the quinolinyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the furyl group, the thienyl group, the pyrrolidinyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the oxadiazolyl group, the thiadiazolyl group, the benzofuryl group, and the benzothienyl group may have one or more substituents selected from Group A}.

[0048] Group H: A group consisting of a C3-C8 alicyclic hydrocarbon group, an indanyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a phenoxy group, a naphthyl group, a pyridyl group, a quinolinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a furyl group, a thienyl group, a pyrrolidinyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuryl group, a benzothienyl group, a 1,3-benzodioxolyl group, a 1,4-benzodioxanyl group {the C3-C8 alicyclic hydrocarbon group, the indanyl group, the 1,2,3,4-tetrahydronaphthyl group, the phenyl group, the phenoxy group, the naphthyl group, the pyridyl group, the quinolinyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the furyl group, the thienyl group, the pyrrolidinyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the oxadiazolyl group, the thiadiazolyl group, the benzofuryl group, the benzothienyl group, the 1,3-benzodioxolyl group, and the 1,4-benzodioxanyl group may have one or more substituents selected from Group C}, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, and CONR 54 R 55 composed of. ]

[0049] 〔2〕The compound or its salt according to 〔1〕, wherein R 1 is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0050] 〔3〕The compound or its salt according to 〔1〕 or 〔2〕, wherein R 8 and R 9 are the same or different from each other and are a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0051] 〔4〕The compound or its salt according to any one of 〔1〕to 〔3〕, wherein R 10 is a C1-C3 chain hydrocarbon group which may have one or more substituents selected from group D, or a hydrogen atom.

[0052] 〔5〕The compound or its salt according to any one of 〔1〕to 〔4〕, wherein n is 1.

[0053] 〔6〕The compound or its salt according to any one of 〔1〕to 〔5〕, wherein m is 0 or 1.

[0054] 〔7〕The compound or its salt according to any one of 〔1〕to 〔5〕, wherein m is 0.

[0055] 〔8〕A harmful arthropod control composition, which contains an inert carrier and the compound or its salt according to any one of 〔1〕to 〔7〕.

[0056] 〔9〕A composition, which contains one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound or its salt according to any one of 〔1〕to 〔7〕,

[0057] Group (a): The group consisting of an insecticidal active ingredient, a miticidal active ingredient and a nematicidal active ingredient;

[0058] Group (b): A bactericidal active ingredient;

[0059] Group (c): A plant growth regulating ingredient;

[0060] Group (d): A repellent ingredient.

[0061] 〔10〕A method for controlling harmful arthropods, wherein an effective amount of the compound or its salt according to any one of 〔1〕to 〔7〕 or an effective amount of the composition according to 〔9〕 is applied to the harmful arthropods or their habitats.

[0062] 〔11〕A seed or vegetative propagation organ, which retains an effective amount of the compound or its salt according to any one of 〔1〕to 〔7〕 or an effective amount of the composition according to 〔9〕.

[0063] Advantages of the Invention

[0064] By the present invention, harmful arthropods can be controlled. Detailed Description of the Invention

[0065] The substituents in the present invention will be described.

[0066] The halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0067] When the substituent has two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different from each other.

[0068] The expression "CX-CY" in this specification means that the number of carbon atoms is from X to Y. For example, the expression "C1-C6" means that the number of carbon atoms is from 1 to 6.

[0069] The so-called chain hydrocarbon group means an alkyl group, an alkenyl group or an alkynyl group.

[0070] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group and a hexyl group.

[0071] Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 1-ethyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group and a 5-hexenyl group.

[0072] Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-ethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group and a 5-hexynyl group.

[0073] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group and a hexyloxy group.

[0074] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a 2-methylpropionyl group and a hexanoyl group. More specifically, examples of the C1-C3 alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group and an isobutyryl group.

[0075] Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group and a pentyloxycarbonyl group. More specifically, examples of the C1-C3 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group and an isopropoxycarbonyl group.

[0076] Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group and an isopropylsulfonyl group.

[0077] The so-called alicyclic hydrocarbon group means a cycloalkyl group, a cycloalkenyl group or a cycloalkynyl group.

[0078] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.

[0079] As the cycloalkenyl group, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl groups can be mentioned.

[0080] As the cycloalkynyl group, for example, cyclohexynyl group can be mentioned.

[0081] There may be one or more stereoisomers of the compound of the present invention. As the stereoisomers, for example, enantiomers, diastereomers, and geometric isomers can be mentioned. The compound of the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0082] The compound N of the present invention sometimes forms an acid addition salt. As the acid for forming the acid addition salt, for example, inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid can be mentioned. The acid addition salt can be obtained, for example, by mixing the compound N of the present invention with an acid.

[0083] As the form of the compound N of the present invention, the following compounds can be mentioned.

[0084] 〔Form 1〕In the compound N of the present invention, R 4 and R 5 are the same or different from each other and are a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, or a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or R 4 and R 5 together form -(CR 23 R 24 )-(CR 25 R 26 ) d -(CR 27 R 28 )-、or -(CR 29 R 30 ) e -Z 2 -(CR 31 R 32 ) f - compound.

[0085] 〔Form 2〕In the compound N of the present invention, R 4 and R 5 are the same or different from each other and are a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, or R 4 and R 5 together form -(CR 23 R 24 )-(CR 25 R 26 ) d -(CR 27 R 28 )- compound.

[0086] [Mode 3] In the compound N of the present invention, R 4 and R 5 are the same or different from each other and are C1-C6 alkyl groups, or R 4 and R 5 together form a compound of -(CR 23 R 24 )-(CR 25 R 26 ) d -(CR 27 R 28 )-.

[0087] [Mode 4] In Mode 1, R 1 is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0088] [Mode 5] In Mode 2, R 1 is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0089] [Mode 6] In Mode 3, R 1 is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0090] [Mode 7] In Mode 4, R 8 and R 9 are the same or different from each other and are a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, tetrahydrofuranyl, tetrahydrothienyl {the tetrahydrofuranyl and the tetrahydrothienyl may have one or more substituents selected from Group B}, or a hydrogen atom.

[0091] [Mode 8] In Mode 5, R 8 and R 9 are the same or different from each other and are a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, tetrahydrofuranyl, tetrahydrothienyl {the tetrahydrofuranyl and the tetrahydrothienyl may have one or more substituents selected from Group B}, or a hydrogen atom.

[0092] [Mode 9] In Mode 6, R 8 and R9 A compound which is the same as or different from each other and is a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, a tetrahydrofuranyl group, a tetrahydrothienyl group {the tetrahydrofuranyl group and the tetrahydrothienyl group may have one or more substituents selected from Group B}, or a hydrogen atom.

[0093] 〔Mode 10〕In Mode 4, R 8 and R 9 A compound which is the same as or different from each other and is a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0094] 〔Mode 11〕In Mode 5, R 8 and R 9 A compound which is the same as or different from each other and is a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0095] 〔Mode 12〕In Mode 6, R 8 and R 9 A compound which is the same as or different from each other and is a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

[0096] 〔Mode 13〕In Mode 7, R 10 A compound which is a C1-C3 chain hydrocarbon group which may have one or more substituents selected from Group D, a halogen atom, or a hydrogen atom.

[0097] 〔Mode 14〕In Mode 8, R 10 A compound which is a C1-C3 chain hydrocarbon group which may have one or more substituents selected from Group D, a halogen atom, or a hydrogen atom.

[0098] 〔Mode 15〕In Mode 9, R 10 A compound which is a C1-C3 chain hydrocarbon group which may have one or more substituents selected from Group D, a halogen atom, or a hydrogen atom.

[0099] 〔Mode 16〕In Mode 10, R 10 A compound which is a C1-C3 chain hydrocarbon group which may have one or more substituents selected from Group D, a halogen atom, or a hydrogen atom.

[0100] 〔Mode 17〕In Mode 11, R 10A compound which is a C1-C3 chain hydrocarbon group, a halogen atom or a hydrogen atom that may have one or more substituents selected from group D.

[0101] 〔Mode 18〕In Mode 12, R 10 A compound which is a C1-C3 chain hydrocarbon group, a halogen atom or a hydrogen atom that may have one or more substituents selected from group D.

[0102] 〔Mode 19〕In Mode 7, R 10 A compound which is a hydrogen atom.

[0103] 〔Mode 20〕In Mode 8, R 10 A compound which is a hydrogen atom.

[0104] 〔Mode 21〕In Mode 9, R 10 A compound which is a hydrogen atom.

[0105] 〔Mode 22〕In Mode 10, R 10 A compound which is a hydrogen atom.

[0106] 〔Mode 23〕In Mode 11, R 10 A compound which is a hydrogen atom.

[0107] 〔Mode 24〕In Mode 12, R 10 A compound which is a hydrogen atom.

[0108] 〔Mode 25〕A compound in Mode 13 where n is 1.

[0109] 〔Mode 26〕A compound in Mode 14 where n is 1.

[0110] 〔Mode 27〕A compound in Mode 15 where n is 1.

[0111] 〔Mode 28〕A compound in Mode 16 where n is 1.

[0112] 〔Mode 29〕A compound in Mode 17 where n is 1.

[0113] 〔Mode 30〕A compound in Mode 18 where n is 1.

[0114] 〔Mode 31〕A compound in Mode 19 where n is 1.

[0115] 〔Mode 32〕A compound in Mode 20 where n is 1.

[0116] 〔Mode 33〕A compound in Mode 21 where n is 1.

[0117] 〔Mode 34〕A compound in Mode 22 where n is 1.

[0118] [Mode 35] A compound in which n is 1 in Mode 23.

[0119] [Mode 36] A compound in which n is 1 in Mode 24.

[0120] [Mode 37] A compound in which m is 0 or 1 in Mode 25.

[0121] [Mode 38] A compound in which m is 0 or 1 in Mode 26.

[0122] [Mode 39] A compound in which m is 0 or 1 in Mode 27.

[0123] [Mode 40] A compound in which m is 0 or 1 in Mode 28.

[0124] [Mode 41] A compound in which m is 0 or 1 in Mode 29.

[0125] [Mode 42] A compound in which m is 0 or 1 in Mode 30.

[0126] [Mode 43] A compound in which m is 0 or 1 in Mode 31.

[0127] [Mode 44] A compound in which m is 0 or 1 in Mode 32.

[0128] [Mode 45] A compound in which m is 0 or 1 in Mode 33.

[0129] [Mode 46] A compound in which m is 0 or 1 in Mode 34.

[0130] [Mode 47] A compound in which m is 0 or 1 in Mode 35.

[0131] [Mode 48] A compound in which m is 0 or 1 in Mode 36.

[0132] [Mode 49] A compound in which m is 0 in Mode 25.

[0133] [Mode 50] A compound in which m is 0 in Mode 26.

[0134] [Mode 51] A compound in which m is 0 in Mode 27.

[0135] [Mode 52] A compound in which m is 0 in Mode 28.

[0136] [Mode 53] A compound in which m is 0 in Mode 29.

[0137] [Mode 54] A compound in which m is 0 in Mode 30.

[0138] [Mode 55] A compound in which m is 0 in Mode 31.

[0139] 〔Mode 56〕In mode 32, a compound where m is 0.

[0140] 〔Mode 57〕In mode 33, a compound where m is 0.

[0141] 〔Mode 58〕In mode 34, a compound where m is 0.

[0142] 〔Mode 59〕In mode 35, a compound where m is 0.

[0143] 〔Mode 60〕In mode 36, a compound where m is 0.

[0144] 〔Mode 61〕Among any of modes 1 to 60 or compound N of the present invention, a compound where Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group F, or a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group H.

[0145] 〔Mode 62〕Among any of modes 1 to 60 or compound N of the present invention, a compound where Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group F.

[0146] 〔Mode 63〕Among any of modes 1 to 60 or compound N of the present invention, a compound where Y is an oxygen atom, p is 1, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group H, or a group selected from group G.

[0147] 〔Mode A1〕In compound N of the present invention, R 10 is a C1-C3 chain hydrocarbon group that may have one or more substituents selected from group D, a halogen atom, or a hydrogen atom.

[0148] 〔Mode A2〕In compound N of the present invention, R 10 is a methyl group, a halogen atom, or a hydrogen atom.

[0149] 〔Mode A3〕In compound N of the present invention, R 10 is a hydrogen atom.

[0150] 〔Mode A4〕In mode A1, a compound where Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group F, or a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group H.

[0151] 〔Mode A5〕In mode A2, a compound where Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from group F, or a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group H.

[0152] [Mode A6] In Mode A3, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F, or a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from Group H.

[0153] [Mode A7] In Mode A1, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F.

[0154] [Mode A8] In Mode A2, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F.

[0155] [Mode A9] In Mode A3, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F.

[0156] [Mode A10] In Mode A1, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F 2 in the C1-C8 chain hydrocarbon group.

[0157] Group F 2 : A group consisting of a C3-C6 alicyclic hydrocarbon group, a phenyl group, a naphthyl group, a benzofuranyl group, a benzothiophenyl group {the C3-C6 alicyclic hydrocarbon group, the phenyl group, the naphthyl group, the benzofuranyl group, and the benzothiophenyl group may have one or more substituents selected from Group C 2}, and a halogen atom.

[0158] Group C 2 : A group consisting of a C1-C3 alkyl group that may have one or more halogen atoms, a C1-C3 alkoxy group that may have one or more halogen atoms, a phenyl group that may have one or more substituents selected from Group B 2 , and a halogen atom.

[0159] Group B 2 : A group consisting of a C1-C3 alkyl group that may have one or more halogen atoms, a C1-C3 alkoxy group that may have one or more halogen atoms, and a halogen atom.

[0160] [Mode A11] In Mode A2, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F 2 in the C1-C8 chain hydrocarbon group.

[0161] [Mode A12] In Mode A3, Y is a single bond, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group F 2 in the C1-C8 chain hydrocarbon group.

[0162] [Mode A13] In Mode A1, Y is an oxygen atom, p is 1, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group H, or a compound of one kind of group selected from Group G.

[0163] [Mode A14] In Mode A2, Y is an oxygen atom, p is 1, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group H, or a compound of one kind of group selected from Group G.

[0164] [Mode A15] In Mode A3, Y is an oxygen atom, p is 1, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group H, or a compound of one kind of group selected from Group G.

[0165] [Mode A16] In Mode A1, Y is an oxygen atom, p is 1, R 11 and R 12 are hydrogen atoms, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group H 2 , or a compound of one kind of group selected from Group G 2 .

[0166] Group H 2 : A group consisting of a C3-C6 cycloaliphatic hydrocarbon group, a phenyl group, a naphthyl group, a benzofuranyl group, a benzothienyl group {the C3-C6 cycloaliphatic hydrocarbon group, the phenyl group, the naphthyl group, the benzofuranyl group, and the benzothienyl group may have one or more substituents selected from Group C 2}, and a halogen atom.

[0167] Group G 2 : A group consisting of a C3-C6 cycloaliphatic hydrocarbon group, a phenyl group, a naphthyl group, a benzofuranyl group, a benzothienyl group {the C3-C6 cycloaliphatic hydrocarbon group, the phenyl group, the naphthyl group, the benzofuranyl group, and the benzothienyl group may have one or more substituents selected from Group A 2}, and a halogen atom.

[0168] Group A 2 : A group consisting of a C1-C3 alkoxy group that may have one or more halogen atoms, and a phenyl group that may have one or more halogen atoms.

[0169] [Mode A17] In Mode A2, Y is an oxygen atom, p is 1, R 11 and R 12 are hydrogen atoms, and Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from Group H 2 , or a compound of one kind of group selected from Group G 2 .

[0170] [Mode A18] In Mode A3, Y is an oxygen atom, p is 1, R 11and R 12 is a hydrogen atom, Q is a C1-C8 chain hydrocarbon group that may have one or more substituents selected from the group H 2 or a compound of one group selected from the group G 2 .

[0171] 〔Mode B1〕In the compound N of the present invention, R 4 is a C1-C3 alkyl group that may have one or more halogen atoms, R 5 is a C1-C3 alkyl group that may have one or more halogen atoms or a hydrogen atom, or R 4 and R 5 together form a compound of -(CH2)4-.

[0172] 〔Mode B2〕In the compound N of the present invention, R 4 and R 5 are the same or different from each other and are C1-C3 alkyl groups that may have one or more halogen atoms, or R 4 and R 5 together form a compound of -(CH2)4-.

[0173] 〔Mode B3〕In the compound N of the present invention, R 4 and R 5 are the same or different from each other and are C1-C3 alkyl groups, or R 4 and R 5 together form a compound of -(CH2)4-.

[0174] 〔Mode B4〕In the compound N of the present invention, R 4 and R 5 together form a compound of -(CH2)4-.

[0175] 〔Mode B5〕In Mode B1, R 1 is a compound of a C1-C4 alkyl group or a hydrogen atom that may have one or more halogen atoms.

[0176] 〔Mode B6〕In Mode B2, R 1 is a compound of a C1-C4 alkyl group or a hydrogen atom that may have one or more halogen atoms.

[0177] 〔Mode B7〕In Mode B3, R 1 is a compound of a C1-C4 alkyl group or a hydrogen atom that may have one or more halogen atoms.

[0178] 〔Mode B8〕In Mode B4, R 1 is a compound of a C1-C4 alkyl group or a hydrogen atom that may have one or more halogen atoms.

[0179] 〔Mode B9〕In Mode B5, R8 and R 9 are the same as or different from each other and are C1-C20 chain hydrocarbon groups which may have one or more substituents selected from Group A 2 , C3-C6 cycloalkyl groups which may have one or more substituents selected from Group A 2 , or a compound of a hydrogen atom.

[0180] [Mode B10] In Mode B5, R 8 and R 9 are the same as or different from each other and are a compound of a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A 2 or a hydrogen atom.

[0181] [Mode B11] In Mode B6, R 8 and R 9 are the same as or different from each other and are C1-C20 chain hydrocarbon groups which may have one or more substituents selected from Group A 2 , C3-C6 cycloalkyl groups which may have one or more substituents selected from Group A 2 , or a compound of a hydrogen atom.

[0182] [Mode B12] In Mode B6, R 8 and R 9 are the same as or different from each other and are a compound of a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A 2 or a hydrogen atom.

[0183] [Mode B13] In Mode B7, R 8 and R 9 are the same as or different from each other and are C1-C20 chain hydrocarbon groups which may have one or more substituents selected from Group A 2 , C3-C6 cycloalkyl groups which may have one or more substituents selected from Group A 2 , or a compound of a hydrogen atom.

[0184] [Mode B14] In Mode B7, R 8 and R 9 are the same as or different from each other and are a compound of a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A 2 or a hydrogen atom.

[0185] [Mode B15] In Mode B8, R 8 and R 9 are the same as or different from each other and are C1-C20 chain hydrocarbon groups which may have one or more substituents selected from Group A 2 , C3-C6 cycloalkyl groups which may have one or more substituents selected from Group A 2A compound having one or more substituents selected from C3-C6 cycloalkyl or a hydrogen atom.

[0186] [Mode B16] In Mode B8, R 8 and R 9 are the same or different from each other and are a C1-C20 chain hydrocarbon group or a hydrogen atom which may have one or more substituents selected from Group A 2 A compound having one or more substituents selected from Group A or a hydrogen atom.

[0187] [Mode B17] In any one of Modes B1 to B16 or Compound N of the present invention, n is 1, and R 6 and R 7 is a hydrogen atom.

[0188] [Mode B18] In any one of Modes B1 to B16 or Compound N of the present invention, n is 1, R 6 and R 7 are hydrogen atoms, m is 0 or 1, and R 2 and R 3 are hydrogen atoms.

[0189] [Mode B19] In any one of Modes B1 to B16 or Compound N of the present invention, n is 1, R 6 and R 7 are hydrogen atoms, and m is 0.

[0190] A compound which is any one of Modes A1 to A18 and any one of Modes B1 to B19.

[0191] Next, a method for producing the compound of the present invention will be described.

[0192] Production Method 1

[0193] The compound represented by formula (I) (i.e., Compound N of the present invention) can be produced by reacting the compound represented by formula (M-1) (hereinafter referred to as Compound (M-1)) with the compound represented by formula (M-2) (hereinafter referred to as Compound (M-2)) in the presence of a condensing agent.

[0194]

[0195] [In the formula, the symbols represent the same meanings as described above.]

[0196] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene (hereinafter referred to as aromatic hydrocarbons); aliphatic hydrocarbons such as hexane (hereinafter referred to as aliphatic hydrocarbons); ethers such as diethyl ether and tetrahydrofuran (hereinafter referred to as THF) (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) (hereinafter referred to as amides); esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); and mixtures thereof.

[0197] Examples of the condensing agent used in the reaction include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate. Regarding the amount of the condensing agent used in the reaction, it can generally be used in any proportion from 1 mole to an excess amount relative to 1 mole of the compound (M-1), and preferably 1 mole to 3 moles.

[0198] The reaction can be carried out in the presence of a base as needed. Examples of the base used in the reaction include carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as carbonates); tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, and 1,5-diazabicyclo[4.3.0]non-5-ene (hereinafter referred to as tertiary amines); and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine (hereinafter referred to as nitrogen-containing aromatic compounds). Regarding the amount of the base used, it can generally be used in any proportion from 1 mole to an excess amount relative to 1 mole of the compound (M-1), and preferably 1 mole to 3 moles.

[0199] The reaction can also be carried out in the presence of 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide, etc. instead of or in addition to the base as needed. Regarding their amounts used, it can generally be used in any proportion from 0.01 mole to 1 mole relative to 1 mole of the compound (M-1), and preferably in a proportion of 0.05 mole to 0.2 mole.

[0200] The reaction time of the reaction is usually in the range of 5 minutes to 72 hours. The reaction temperature of the reaction is usually in the range of -20°C to 100°C (wherein, when the boiling point of the solvent used is lower than 100°C, it is -20°C to the boiling point of the solvent).

[0201] In the reaction, the molar ratio of compound (M-1) to compound (M-2) can be arbitrarily set, but is preferably an equimolar ratio or a ratio close thereto. For example, the ratio of compound (M-2) is 1 to 3 moles relative to 1 mole of compound (M-1).

[0202] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are performed to obtain the compound N of the present invention.

[0203] Compound (M-2) is a commercially available compound or can be produced according to known methods.

[0204] Production method 2

[0205] The compound N of the present invention can also be produced by reacting the compound represented by formula (M-3) (hereinafter referred to as compound (M-3)) with compound (M-2) in the presence of a base.

[0206]

[0207] [In the formula, G 1 represents a chlorine atom, a bromine atom or an iodine atom, and the other symbols represent the same meanings as described above.]

[0208] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aliphatic hydrocarbons; aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles such as acetonitrile and butyronitrile (hereinafter referred to as nitriles); amides; sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as sulfoxides); and mixtures thereof.

[0209] Examples of the base used in the reaction include carbonates, tertiary amines, and nitrogen-containing aromatic compounds. Regarding the amount of the base used, it can usually be used in any ratio from 1 mole to an excess amount relative to 1 mole of compound (M-3), and is preferably 1 to 3 moles.

[0210] The reaction time of the reaction is usually in the range of 5 minutes to 72 hours. The reaction temperature of the reaction is usually in the range of -20°C to 100°C.

[0211] In the reaction, the molar ratio of compound (M-3) to compound (M-2) can be arbitrarily set, but is preferably an equimolar ratio or a ratio close thereto. Specifically, relative to 1 mole of compound (M-3), compound (M-2) is 0.5 to 3 moles.

[0212] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are performed to obtain the compound N of the present invention.

[0213] Manufacturing method 3

[0214] The compound N of the present invention can also be produced by reacting the compound represented by the formula (M-4) (hereinafter referred to as compound (M-4)) with compound (M-2).

[0215]

[0216] [In the formula, G 2 represents methyl or ethyl, and the other symbols represent the same meanings as described above.]

[0217] The reaction can be carried out in a solvent or under solvent-free conditions. Examples of the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, esters, nitriles, amides, sulfoxides, and mixtures thereof.

[0218] The reaction time of the reaction is usually in the range of 5 minutes to 72 hours. The reaction temperature of the reaction is usually in the range of 50°C to 200°C.

[0219] In the reaction, the molar ratio of compound (M-4) to compound (M-2) can be arbitrarily set, but an equimolar ratio or a ratio close thereto is preferred. Specifically, with respect to 1 mole of compound (M-4), compound (M-2) is 0.5 to 3 moles.

[0220] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain the compound N of the present invention.

[0221] Manufacturing method 4

[0222] The compound N of the present invention can also be produced by reacting the compound represented by the formula (M-5) (hereinafter referred to as compound (M-5)) with the compound represented by the formula (M-6) (hereinafter referred to as compound (M-6)).

[0223]

[0224] [In the formula, the symbols represent the same meanings as described above.]

[0225] The reaction can be carried out in a solvent or under solvent-free conditions. Examples of the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, esters, nitriles, amides, sulfoxides, and mixtures thereof.

[0226] The reaction time of the reaction is usually in the range of 5 minutes to 72 hours. The reaction temperature of the reaction is usually in the range of -20°C to 160°C.

[0227] In the reaction, the molar ratio of compound (M-5) to compound (M-6) can be arbitrarily set. Preferably, relative to 1 mole of compound (M-5), compound (M-6) is 1 mole to 50 moles.

[0228] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound N of the present invention.

[0229] Compound (M-6) is a commercially available compound or can be manufactured according to known methods. In compound (M-6), R 8 and R 9 When they are hydrogen atoms, that is, when compound (M-6) is formaldehyde, paraformaldehyde can also be used instead of compound (M-6).

[0230] Hereinafter, the manufacturing method of the intermediate will be described.

[0231] Reference Manufacturing Method 1

[0232] Compound (M-1) can be manufactured by subjecting compound (M-4) to a hydrolysis reaction in the presence of a base.

[0233]

[0234] [In the formula, the symbols represent the same meanings as described above.]

[0235] The reaction can be carried out in the presence of a base, water and an organic solvent. Examples of the solvent used in the reaction include ethers; nitriles; alcohols such as methanol, ethanol, and propanol; and mixtures thereof.

[0236] Examples of the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.

[0237] The reaction time of the reaction is usually in the range of 5 minutes to 72 hours. The reaction temperature of the reaction is usually in the range of 0 °C to 100 °C.

[0238] Regarding the amount of the base used in the reaction, it can usually be used in any proportion from 1 mole to an excess amount relative to 1 mole of compound (M-1), and preferably 1 mole to 5 moles.

[0239] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound (M-1).

[0240] Reference Manufacturing Method 2

[0241] Compound (M-3) can be produced by reacting compound (M-1) with a halogenating agent.

[0242]

[0243] [In the formula, the symbols represent the same meanings as described above.]

[0244] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, and mixtures thereof.

[0245] Examples of the halogenating agent used in the reaction include thionyl chloride, oxalyl chloride, phosphoryl chloride, phosphoryl bromide, and phosphorus tribromide.

[0246] The reaction time of the reaction is usually in the range of 5 minutes to 24 hours. The reaction temperature of the reaction is usually in the range of 0 to 100 °C.

[0247] Regarding the amount of the halogenating agent used in the reaction, it can usually be used in any ratio from 1 mole to an excess amount relative to 1 mole of compound (M-1), and preferably 1 to 5 moles.

[0248] After the reaction is completed, post-treatment operations such as concentration can be directly performed on the reaction mixture to obtain compound (M-3).

[0249] Reference Production Method 3

[0250] Compound (M-4) can be produced by reacting the compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) with the compound represented by formula (M-8) (hereinafter referred to as compound (M-8)).

[0251]

[0252] [In the formula, the symbols represent the same meanings as described above.]

[0253] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, and mixtures thereof.

[0254] The reaction time of the reaction is usually in the range of 5 minutes to 24 hours. The reaction temperature of the reaction is usually in the range of 0 to 100 °C.

[0255] In the reaction, the molar ratio of compound (M-7) to compound (M-8) can be arbitrarily set, but preferably, relative to 1 mole of compound (M-7), compound (M-8) is 1 mole to 10 moles.

[0256] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. After-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound (M-4).

[0257] Compound (M-7) is a commercially available compound or can be produced according to a known method.

[0258] Compound (M-8) is a commercially available compound.

[0259] Reference Production Method 4

[0260] Compound (M-2) can be produced by reacting the compound represented by formula (M-9) (hereinafter referred to as compound (M-9)) with compound (M-6).

[0261]

[0262] [In the formula, the symbols represent the same meanings as described above.]

[0263] The reaction can be carried out according to Production Method 4 using compound (M-9) instead of compound (M-5).

[0264] Compound (M-9) is a commercially available compound or can be produced according to a known method.

[0265] Reference Production Method 5

[0266] Compound (M-5) can be produced by reacting compound (M-1) with compound (M-9) in the presence of a condensing agent.

[0267]

[0268] [In the formula, the symbols represent the same meanings as described above.]

[0269] The reaction can be carried out according to Production Method 1 using compound (M-9) instead of compound (M-2).

[0270] The compound of the present invention can be mixed or used in combination with one or more components selected from the following groups (a), (b), (c), and (d) (hereinafter referred to as this component).

[0271] The above-mentioned mixing or using in combination means that the compound of the present invention and this component are used simultaneously, separately, or at intervals.

[0272] When the compound of the present invention and this component are used simultaneously, the compound of the present invention and this component can be contained in separate preparations or in the same preparation.

[0273] One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., this component) and a compound of the present invention.

[0274] Group (a) is a group consisting of acetylcholinesterase inhibitors (e.g., carbamate pesticides, organophosphorus pesticides), GABA-gated chloride channel blockers (e.g., phenylpyrazole pesticides), sodium channel modulators (e.g., pyrethroid pesticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid pesticides), allosteric modulators of nicotinic acetylcholine receptors, allosteric modulators of glutamate-gated chloride channels (e.g., macrolide pesticides), juvenile hormone mimetics, multi-site inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, insect midgut intima disruptors derived from microorganisms, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin pesticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III, and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide pesticides), chordotonal organ modulators, microbial pesticides, and other insecticidal, acaricidal, and nematicidal active ingredients. These ingredients are listed according to the classification of the mode of action based on IRAC.

[0275] Group (b) is a group consisting of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are listed according to the classification of the mode of action based on FRAC.

[0276] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[0277] Group (d) is a group of repellent components.

[0278] Examples of the combination of this component and the compound of the present invention are described below. For example, alanycarb + SX means the combination of alanycarb and SX.

[0279] It should be noted that the abbreviation of SX refers to any one of the present invention compounds selected from the compound groups SX1 to SX210 and the present invention compounds 1 to 108 of the present invention. In addition, the components described below are all known components, which can be obtained from commercially available preparations or manufactured by known methods. When the component is a microorganism, it can also be obtained from a microorganism preservation institution. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0280] The combination of the component of the above group (a) and the present invention compound:

[0281] Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha-cypermethrin + SX, Alpha-endosulfan + SX, Aluminium phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphidephosphide)+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride+SX, cartap+SX, chinomethionat+SX, chlorantraniliprole+SX, chlordane+SX, chlorethoxyfos+SX, chlorfenapyr+SX, chlorfenvinphos+SX, chlorfluazuron+SX, chlormephos+SX, chloropicrin+SX, chlorpyrifos+SX, chlorpyrifos-methyl+SX, chromafenozide+SX, clofentezine+SX, clothianidin+SX, concanamycinA) +SX, coumaphos +SX, cryolite +SX, cyanophos +SX, cyantraniliprole +SX, cyclaniliprole +SX, cyclobutrifluram +SX, cycloprothrin +SX, cycloxaprid +SX, cyenopyrafen +SX, cyetpyrafen +SX, cyflumetofen +SX, cyfluthrin +SX, cyhalodiamide +SX, cyhalothrin +SX, cyhexatin +SX, cypermethrin +SX, cyphenothrin +SX, cyproflanilide +SX, cyromazine +SX, dazomet +SX, deltamethrin +SX, demeton-S-methyl +SX, diafenthiuron +SX, diazinon +SX, dichlorvos +SX, dicloromezotiaz +SX, dicofol +SX, dicrotophos +SX, diflovidazin +SX, diflubenzuron +SX, dimefluthrin +SX, dimethoate +SX, dimethylvinphos +SX, dimpropyridaz +SX, dinotefuran +SX, disodium octaborate +SX, disulfoton +SX, DNOC (2-methyl-4,6-dinitrophenol +SX, doramectin +SX, dried leaves of Dryopterisfilix-mas)+SX, emamectin-benzoate)+SX, empenthrin)+SX, endosulfan)+SX, EPN (O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, epsilon-metofluthrin)+SX, epsilon-momfluorothrin+SX, esfenvalerate)+SX, ethiofencarb)+SX, ethion)+SX, ethiprole)+SX, ethoprophos)+SX, etofenprox)+SX, etoxazole)+SX, extract of Artemisia absinthium)+SX, extract of Azadirachta indica)+SX, extract of Cassia nigricans)+SX, extract of clitoria ternatea)+SX, extract of Symphytum officinale)+SX, extract of Chenopodium ambrosioides)+SX, extract of Tanacetum vulgare)+SX, extract of Urtica dioica)+SX, extract of Viscum album)+SX, famphur)+SX, fenamiphos)+SX, fenazaquin)+SX, fenbutatinoxide)+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, flometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX, fluchlordiniliprole+SX, flucycloxuron+SX, flucythrinate+SX, fluensulfone+SX, flufenoprox+SX, flufenoxuron+SX, flufiprole+SX, flumethrin+SX, flupentiofenox+SX, flupyradifurone+SX, flupyrimin+SX, flupyroxystrobin+SX, fluralaner+SX, fluvalinate+SX, fluxametamide+SX, formetanate+SX, fosthiazate+SX, furamethrin+SX, furathiocarb+SX, gamma-cyhalothrin+SX, GS-omega / kappa HXTX-Hv1a peptide+SX, halfenprox+SX, halofenozide+SX, heptafluthrin+SX, heptenophos+SX, hexaflumuron+SX, hexythiazox+SX, potassium salt ofhop betaacid)+SX, hydramethylnon)+SX, hydroprene)+SX, imicyafos)+SX, imidacloprid)+SX, imidaclothiz)+SX, imiprothrin)+SX, indazapyroxamet)+SX, indoxacarb)+SX, isocycloseram+SX, isofenphos)+SX, isoprocarb)+SX, isopropyl-O-(methoxyaminothiophosphoryl)salicylate)+SX, isoxathion)+SX, ivermectin)+SX, kadethrin)+SX, kappa-tefluthrin)+SX, kappa-bifenthrin)+SX, kinoprene)+SX, lambda-cyhalothrin)+SX, ledprona+SX, lenoremycin)+SX, lepimectin)+SX, lime sulfur)+SX, lotilaner)+SX, lufenuron)+SX, machine oil)+SX, malathion)+SX, mecarbam)+SX, meperfluthrin)+SX, metaflumizone)+SX, metam)+SX, methamidophos)+SX, methidathion)+SX, methiocarb)+SX, methomyl)+SX, methoprene)+SX, methoxychlor)+SX, methoxyfenozide)+SX, methyl bromide)+SX, metofluthrin)+SX, metolcarb)+SX, metoxadiazone)+SX, mevinphos)+SX, milbemectin)+SX, milbemycinoxime)+SX, mivorilaner+SX, flubendiamide (modoflaner)+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX, nicofluprole+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX, novaluron+SX, noviflumuron+SX, oil of the seeds of Chenopodium anthelminticum+SX, omethoate+SX, oxamyl+SX, oxazosulfyl+SX, oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, permethrin+SX, phenothrin+SX, phenthoate+SX, phorate+SX, phosalone+SX, phosmet+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginate (propyleneglycolalginate)+SX, prothiofos)+SX, pyflubumide+SX, pymetrozine)+SX, pyraclofos)+SX, pyrethrins)+SX, pyridaben)+SX, pyridalyl)+SX, pyridaphenthion)+SX, pyrifluquinazone)+SX, pyrimidifen)+SX, pyriminostrobin)+SX, pyriprole)+SX, pyriproxyfen)+SX, quinalphos)+SX, resmethrin)+SX, rotenone)+SX, ryanodine)+SX, sarolaner)+SX, selamectin)+SX, sigma-cypermethrin)+SX, silafluofen)+SX, sodium borate)+SX, sodium metaborate)+SX, spidoxamat+SX, spinetoram)+SX, spinosad)+SX, spirobudifen)+SX, spirodiclofen)+SX, spiromesifen)+SX, spiropidion)+SX, spirotetramat)+SX, sulfiflumin)+SX, sulfluramid)+SX, sulfotep)+SX, sulfoxaflor)+SX, sulfur)+SX, sulfurylfluoride)+SX, tartar emetic)+SX, tau-fluvalinate)+SX, tebufenozide)+SX, tebufenpyrad)+SX, tebupirimfos)+SX, teflubenzuron)+SX, tefluthrin)+SX, temephos)+SX, terbufos)+SX, terpene components extracted from Chenopodium ambrosioidesConstituents of the extract of Chenopodium ambrosioides near Ambrosioides)+SX, tetrachlorantraniliprole+SX, tetrachlorvinphos+SX, tetradifon+SX, tetramethrin+SX, tetramethylfluthrin+SX, tetraniliprole+SX, theta-cypermethrin+SX, thiacloprid+SX, thiamethoxam+SX, thiocyclam+SX, thiodicarb+SX, thiofanox+SX, thiometon+SX, thiosultap-disodium+SX, thiosultap-monosodium+SX, tigolaner+SX, tiorantraniliprole+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, trifluenfuronate+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, umifoxolaner+SX, vamidothion+SX, wood extract of Quassia amara+SX, XMC (3,5-dimethylphenyl N-methylcarbamate, N-methylamino 3,5-dimethylphenyl ester)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphidephosphide) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}inden-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methylsulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylthio)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methylsulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT cropprotein Cry1Fa)+SX, BT crop protein Cry1A.105)+SX, BT crop protein Cry2Ab)+SX, BT crop protein Vip3A)+SX, BT crop protein mCry3A)+SX, BT crop protein Cry3Ab)+SX, BT crop protein Cry3Bb)+SX, BT crop protein Cry34Ab1 / Cry35Ab1)+SX, Adoxophyes orana GV (granulovirus) strain BV-0001)+SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus))+SX, Autographa californica MNPV)+SX, Cydia pomonella GV strain V15)+SX, Cydia pomonella GV strain V22)+SX, Cryptophlebia leucotreta GV)+SX, Dendrolimus punctatus cypovirus)+SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003)+SX, Helicoverpa zea NPV)+SX, Lymantria dispar NPV)+SX, Mamestra brassicae NPV)+SX, Mamestra configurata NPV)+SX, Neodiprion abietisNPV)+SX, Neodiprion lecontei NPV)+SX, Neodiprion sertifer NPV)+SX, Nosema locustae)+SX, Orgyia pseudotsugata NPV)+SX, Pieris rapae GV)+SX, Plodia interpunctella GV)+SX, Spodoptera exigua MNPV)+SX, Spodoptera littoralis MNPV)+SX, Spodoptera litura NPV)+SX, Arthrobotrys dactyloides)+SX, Bacillus firmus strain GB-126)+SX, Bacillus firmus strain I-1582)+SX, Bacillus firmus strain NCIM2637)+SX, Bacillus megaterium)+SX, Bacillus sp. strain AQ175)+SX, Bacillus sp. strain AQ177)+SX, Bacillus sp. strain AQ178)+SX, Bacillus sphaericus strain 2362 serotype H5a5b)+SX, Bacillus sphaericus strain ABTS1743)+SX, Bacillus thuringiensis strain AQ52)+SX, Bacillus thuringiensis strain BD#32)+SX, Bacillus thuringiensis strain CR-371)+SX,CR-371)+SX, Bacillus thuringiensis subsp. aizawai strain ABTS-1857)+SX, Bacillus thuringiensis subsp. aizawai strain AM65-52)+SX, Bacillus thuringiensis subsp. aizawai strain GC-91)+SX, Bacillus thuringiensis subsp. aizawai strain NB200)+SX, Bacillus thuringiensis subsp. aizawai Serotype strain H-7)+SX, Bacillus thuringiensis subsp. kurstaki strain ABTS351)+SX, Bacillus thuringiensis subsp. kurstaki strain BMP123)+SX, Bacillus thuringiensis subsp. kurstaki strain CCT1306)+SX, Bacillus thuringiensis subsp. kurstaki strain EG2348)+SX, Bacillus thuringiensis subsp. kurstaki strain EG7841)+SX, Bacillus thuringiensis subsp. kurstaki strain EVB113-19)+SX, Bacillus thuringiensis subsp. kurstaki strain F810)+SX, Bacillus thuringiensis subsp. kurstaki strain HD-1)+SXstrain HD-1)+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54)+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11)+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12)+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176)+SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002)+SX, Bacillus thuringiensis subsp. morrisoni)+SX, Bacillus thuringiensis var. colmeri)+SX, Bacillus thuringiensis var. darmstadiensis strain 24-91)+SX, Bacillus thuringiensis var. dendrolimus)+SX, Bacillus thuringiensis var. galleriae)+SX, Bacillus thuringiensis var. israelensis strain BMP144)+SX, Bacillus thuringiensis var. israelensis serotype strain H-14)+SX, Bacillus thuringiensis var. japonensis strain buibui)+SX, Bacillus thuringiensis var. sandiego strain M-7)+SXM-7)+SX, Bacillus thuringiensis var. 7216+SX, Bacillus thuringiensis var. aegypti+SX, Bacillus thuringiensis var. T36+SX, Beauveria bassiana strain ANT-03+SX, Beauveria bassiana strain ATCC74040+SX, Beauveria bassiana strain GHA+SX, Beauveria brongniartii+SX, Burkholderia rinojensis strain A396+SX, Chromobacterium subtsugae strain PRAA4-1T+SX, Dactyllela ellipsospora+SX, Dectylaria thaumasia+SX, Hirsutella minnesotensis+SX, Hirsutella rhossiliensis+SX, Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium lecanii strain KV01+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX, Lecanicillium lecanii conidia of strain DAOM216596+SX, Lecanicillium muscarium strain Ve6+SX, Metarhizium anisopliae strain F52+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. anisopliae microspora BIPESCO5 / F52 strain (Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52) + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawa strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecanii strain NCIM1312 + SX, Wolbachia pipientis + SX.

[0282] Combination of the present component of group (b) with the compound of the present invention:

[0283] acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II)acetate + SX, copper(II)hydroxide + SX, copperoxychloride + SX, copper(II)sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SXCymoxanil + SX, Cyproconazole + SX, Cyprodinil + SX, Dichlobentiazox + SX, Dichlofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dicloran + SX, Diethofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole - M + SX, Dinocap + SX, Dipotassium hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acid bisethylenediamine copper(II)salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Extract of Allium sativum, Extract of the cotyledons of lupine plantlets(“BLAD”), Extract of Equisetum arvense, Extract of Melaleuca alternifolia, Extract of Reynoutria sachalinensis, Extract of Tropaeolum majusFamoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate + SX, Fentinchloride + SX, Fentin hydroxide + SX, Ferbam + SX, Ferimzone + SX, Florylpicoxamid + SX, Fluazinam + SX, Flubeneteram + SX, Fludioxonil + SX, Flufenoxadiazam + SX, Flufenoxystrobin + SX, Fluindapyr + SX, Flumetylsulforim + SX, Flumorph + SX, Fluopicolide + SX, Fluopyram + SX, Fluopimomide + SX, Fluoroimide + SX, Fluoxapiprolin + SX, Fluoxastrobin + SX, Fluoxytioconazole + SX, Fluquinconazole + SX, Flusilazole + SX, Flusulfamide + SX, Flutianil + SX, Flutolanil + SX, Flutriafol + SX, Fluxapyroxad + SX, Folpet + SX, Fosetyl + SX, Fosetyl - aluminium + SX, Fuberidazole + SX, Furalaxyl + SX, Furametpyr + SX, Guazatine + SX,Hexaconazole + SX, Hymexazole + SX, Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine triacetate + SX, Inpyrfluxam + SX, Iodocarb + SX, Ipconazole + SX, Ipflentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamid + SX, Metconazole + SX, Methasulfocarb + SX, Metiram + SX, Metominostrobin + SX, Metrafenone + SX, Metyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octhilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX,Oxathiapiprolin + SX, Oxine - copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxycarboxin + SX, Oxytetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX, Piperalin + SX, Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, Probenazole + SX, Prochloraz + SX, Procymidone + SX, Propamidine + SX, Propamocarb + SX, Propiconazole + SX, Propineb + SX, Proquinazid + SX, Prothiocarb + SX, Prothioconazole + SX, Pydiflumetofen + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyraoxystrobin + SX, Pyrapropoyne + SX, Pyraziflumid + SX, Pyrazophos + SX, Pyribencarb + SX, Pyributicarb + SX, Pyridachlometyl + SX, Pyrifenox + SX, Pyrimethanil + SX, Pyrimorph + SX,Pyriofenone + SX, Pyrisoxazole + SX, Pyroquilon + SX, Quillaja extract + SX, Quinconazole + SX, Quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX, Saponins of Chenopodium quinoa + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium hydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thiophanate + SX, Thiophanate-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos-methyl + SX, Tolfenpyrad + SX, Tolprocarb + SX, Tolylfluanid + SX, Triadimefon + SX, Triadimenol + SX, Triazoxide + SX, Triclopyricarb + SX, Tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX, Triticonazole + SX, Validamycin + SX, Valifenalate + SX,Vinclozolin + SX, Yellow mustard powder + SX, Zinc thiazole + SX, Zineb + SX, Ziram + SX, Zoxamide + SX, N’-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (1202781-91-6) + SX, N’-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidine (929908-57-6) + SX, N’-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (1052688-31-9) + SX, N’-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidine (2055589-28-9) + SX, N’-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (2055756-21-1) + SX, N’-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidine (2062599-39-5) + SX, N’-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylformamidine (2101814-55-3) + SX, N’-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, (2Z)-Ethyl 3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX,(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S,2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentane-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX,2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(Difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethylsulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SXN-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester + SX, N-{[3-(Acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-Acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-{[3-(Acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-Allyl-N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-Allyl-N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX,3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SXN-Methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, Ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, Methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, 1-(2,3-Dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(Difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-Difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-Chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, Ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, Ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-Chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[Acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-Methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-Methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-Difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxolane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX3-[3-(3-Cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-Cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-Methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)methyl carbamate + SX, ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)methyl carbamate + SX, ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)methyl carbamate + SX, (Z)-methyl 2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyacrylate + SX, (Z)-methyl 2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyacrylate + SX, (Z)-methyl 2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyacrylate + SX, 1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, (2Z)-methyl 3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]acrylate + SX, Agrobacterium radiobactor strain K1026, Agrobacterium radiobactor strain K84, Bacillus amyloliquefaciens strain PTA-4838 (Aveo™ EZ Nematicide), Bacillus amyloliquefaciens strain AT332, Bacillus amyloliquefaciens strain B3, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain DB101Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SXBacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SXBurkholderia cepacia type Wisconsin strain M54 + SX, biocontrol yeast Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, Cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SXPseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa PF-A22UL strain + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SXTrichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SXTrichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX.

[0284] The combination of the present component of group (c) and the compound of the present invention:

[0285] 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl) acetic acid) + SX, IBA (4-(1H-indol-3-yl) butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy) acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy) butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, cholinechloride)+SX, cloprop)+SX, cyanamide)+SX, cyclanilide)+SX, daminozide)+SX, decan-1-ol)+SX, dichlorprop)+SX, dikegulac)+SX, dimethipin)+SX, diquat)+SX, ethephon)+SX, ethychlozate)+SX, flumetralin)+SX, flurprimidol)+SX, forchlorfenuron)+SX, formononetin)+SX, Gibberellin A)+SX, GibberellinA3)+SX, inabenfide)+SX, Kinetin)+SX, lipochitooligosaccharide)SP104+SX, maleic hydrazide)+SX, mefluidide)+SX, mepiquat-chloride)+SX, oxidizedglutathione)+SX, paclobutrazol)+SX, pendimethalin)+SX, prohexadione-calcium)+SX, prohydrojasmon)+SX, pyraflufen-ethyl)+SX, sintofen)+SX, sodium 1-naphthaleneacetate)+SX, sodium cyanate)+SX, thidiazuron)+SX, triapenthenol)+SX, tribufos)+SX, trinexapac-ethyl)+SX, uniconazole-P)+SX, 2-(naphthalen-1-yl)acetamide)+SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid+SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate+SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol+SX, Claroideoglomusetunicatum)+SX, Claroideoglomus claroideum)+SX, Funneliformis mosseae)+SX, Gigaspora margarita)+SX, Gigaspora rosea)+SX, Glomus aggregatum)+SX, Glomus deserticola)+SX, Glomus monosporum)+SX, Paraglomus brasillianum)+SX, Rhizophagus clarus)+SX, Rhizophagus intraradices strain RTI-801)+SX, Rhizophagus irregularis strain DAOM 197198)+SX, Azorhizobium caulinodans)+SX, Azospirillum amazonense)+SX, Azospirillum brasilense strain XOH)+SX, Azospirillum brasilense strain Ab-V5)+SX, Azospirillum brasilense strain Ab-V6)+SX, Azospirillum caulinodans+SX, Azospirillum halopraeferens)+SX, Azospirillum irakense)+SX, Azospirillum lipoferum)+SX, Bradyrhizobium elkanii strain SEMIA 587)+SX, Bradyrhizobium elkanii strain SEMIA 5019)+SX, Bradyrhizobium japonicum strain TA-11)+SX, Bradyrhizobium japonicum strain USDA 110)+SX, Bradyrhizobium liaoningense)+SX, Bradyrhizobium lupini)+SX, Delftia acidovorans strain RAY209)+SX, Mesorhizobium ciceri)+SX, Mesorhizobium huakuiiHuakii)+SX, Mesorhizobium loti)+SX, Rhizobium etli)+SX, Rhizobium galegae)+SX, Rhizobium leguminosarum bv. Phaseoli)+SX, Rhizobium leguminosarum bv. Trifolii)+SX, Rhizobium leguminosarum bv. Viciae)+SX, Rhizobium trifolii)+SX, Rhizobium tropici)+SX, Sinorhizobium fredii)+SX, Sinorhizobium meliloti)+SX, Zucchini Yellow Mosaik Virus weak strain)+SX.

[0286] The combination of the component of the above group (d) and the compound of the present invention:

[0287] Anthraquinone)+SX, Deet)+SX, Icaridin)+SX.

[0288] The ratio of the compound of the present invention to this component is not particularly limited, and examples thereof include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc. based on the weight ratio (compound of the present invention: this component).

[0289] The compound of the present invention is effective against harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following animals.

[0290] Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, Stenocranus pacificus, etc.; Cicadellidae such as Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, Amrasca biguttula biguttula, etc.; Aphrophoridae such as Philaenus spumarius; Cercopidae such as Mahanarva posticata, Mahanarva fimbriolata, etc.Aphididae such as Aphisfabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi, Brevicoryne brassicae, Dysaphis plantaginea, Lipaphis erysimi, Macrosiphum euphorbiae, Aulacorthum solani, Nasonovia ribisnigri, Rhopalosiphumpadi, Rhopalosiphum maidis, Toxoptera citricida, Hyalopterus pruni, Melanaphis sacchari, Tetraneuranigriabdominalis, Ceratovacuna lanigera, Eriosomalanigerum, Sitobion avenae, etc.; Phylloxeridae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc.; Adelgidae such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae, etc.;Pentatomidae such as Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Euschistus heros, Piezodorus guildinii, Oebalus pugnax, Dichelops melacanthus, Piezodorus hybneri, etc.; Cydnidae such as Scaptocoris castanea; Alydidae such as Riptortus clavatus, Leptocorisa chinensis, Leptocorisa acuta; Coreidae such as Cletus punctiger, Leptoglossus australis; Lygaeidae such as Cavelerius saccharivorus, Togohemipterus, Blissus leucopterus; Miridae such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Pealius euryaeScale insects in the family Diaspididae such as Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, etc.; scale insects in the family Coccidae such as Ceroplastes rubens, etc.; scale insects in the family Margarodidae such as Icerya purchasi, Icerya seychellarum, etc.; scale insects in the family Pseudococcidae such as Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi, etc.; psyllids in the family Psyllidae such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola, etc.; lace bugs in the family Tingidae such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc.; bed bugs in the family Cimicidae such as Cimex lectularius, Cimex hemipterus, etc.; cicadas in the family Cicadidae such as Quesada gigas, etc.Triatomine bugs such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodnius prolixus, etc. (Reduviidae);

[0291] Lepidoptera: Crambidae such as Chilo suppressalis, Chilo polychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellula undalis, Herpetogramma luctuosale, Parapediasia teterrellus, Nymphula depunctalis, Diatraea saccharalis, Leucinodes orbonalis, etc.; Pyralidae such as Elasmopalpus lignosellus, Plodia interpunctella, Euzophera batangensis, Cadra cautella, etc.Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis spp. such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Anticarsia gemmatalis, Alabama argillacea, Hydraecia immanis, etc. (Noctuidae); Pieris rapae, etc. (Pieridae);Tortricidae such as Grapholita molesta, Grapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citripestis sagittiferella, Lobesia botrana, etc.; Gracillariidae such as Caloptilia theivora, Phyllonorycter ringoniella, etc.; Carposinidae such as Carposina sasakii, etc.; Lyonetiidae such as Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella, etc.; Lymantriidae such as Lymantria spp. including Lymantria dispar, Euproctis spp. including Euproctis pseudoconspersa, etc.; Plutellidae such as Plutella xylostella, etc.; Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Tuta absoluta, etc.; Arctiidae such as Hyphantria cunea, etc.; Castniidae such as Telchin licus, etc.Cossidae such as Cossus insularis; Geometridae such as Ascotis selenaria; Limacodidae such as Parasalepida; Stathmopodidae such as Stathmopoda masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokona feralis, Synanthedon hector, Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens, Tineola bisselliella.

[0292] Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, Scirtothrips perseae; Phlaeothripidae such as Haplothrips aculeatus.

[0293] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, Pegomya cunicularia, etc.; Ulidiidae such as Tetanops myopaeformis, etc.; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola, etc.; Chloropidae such as Chlorops oryzae, etc.; Tephritidae such as Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae such as Hydrellia griseola, Hydrellia philippina, Hydrellia sasakii, etc.; Drosophilidae such as Drosophila suzukii, Drosophila melanogaster, etc.; Phoridae such as Megaselia spiracularis, etc.; Psychodidae such as Clogmia albipunctata, etc.; Sciaridae such as Bradysia difformis, Bradysia odoriphaga, etc.; Cecidomyiidae such as Mayetiola destructor, Orseolia oryzae, etc.; Diopsidae such as Diopsis macrophthalma, etc.Glossina palpalis, Glossina morsitans, etc. of the family Glossinidae; Simulium japonicum, Simulium damnosum, etc. of the family Simuliidae; the subfamily Phlebotominae; Tipula aino, Tipula oleracea, Tipula paludosa, etc. of the family Tipulidae; Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus, etc. of the family Culicidae; Prosimulium yezoensis, Simulium ornatum, etc. of the family Simuliidae; Tabanus trigonus, etc. of the family Tabanidae; Musca domestica, Muscina stabulans, Stomoxys calcitrans, Haematobia irritans, etc. of the family Muscidae; the family Calliphoridae; the family Sarcophagidae;Chironomidae such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai, etc.; Fannidae.

[0294] Coleoptera: Diabrotica spp. (e.g., Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae, Diabrotica balteata, Cucurbit Beetle (Diabrotica speciosa), etc.), Cerotoma trifurcata, Oulema melanopus, Aulacophora femoralis, Phyllotreta striolata, Phyllotreta cruciferae, Phyllotreta pusilla, Psylliodes chrysocephala, Psylliodes punctulata, Leptinotarsa decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confinis, Epitrix cucumeris, Dicladispa armigera, Myochrous denticollis, Laccoptera quadrimaculata, Epitrix hirtipennis, Phaedon brassicae, Medythia nigrobilineata, etc. (Chrysomelidae); Seedcorn beetle (Stenolophus lecontei), Clivina impressifrons, etc. (Carabidae);Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophyllapicea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga crinita and other Phyllophaga spp., Diloboderus abderus and other Diloboderus spp.; Anthriibidae such as Araecerus coffeae; Aponidae such as Cylas formicarius; Bruchidae such as Zabrotes subfasciatus; Scolytidae such as Tomicus piniperda, Hypothenemus hampei; Curculionidae such as Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineaticollis, Anthonomus grandis, Sphenophorus venatus, Sphenophorus callosus, Sternechus subsignatus, Sphenophorus levis, Scepticus griseus, Scepticus uniformis, Aracanthus mourei and other Aracanthus spp., Eutinobothrus brasiliensis and other Curculionidae;Tenebrionidae such as Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus, etc.; Coccinellidae such as Epilachna vigintioctopunctata, etc.; Bostrychidae such as Lyctus brunneus, Rhizopertha dominica, etc.; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii, etc.; Elateridae such as Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., etc.; Staphylinidae such as Paederus fuscipes, etc.; Dermestidae such as Anthrenus verbasci, Dermestes maculates, Trogoderma granarium, etc.; Anobiidae such as Lasioderma serricorne, Stegobium paniceum, etc.; Laemophloeidae such as Cryptolestes ferrugineus, etc.; Silvanidae such as Oryzaephilus surinamensis, etc.; Nitidulidae such as Brassicogethes aeneus, etc.

[0295] Orthoptera: Acrididae such as Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina, Anacridium melanorhodon, Calliptamus italicus, Melanoplus differentialis, Melanoplus bivittatus, Melanoplus sanguinipes, Melanoplus femurrubrum, Camnula pellucida, Schistocerca gregaria, Gastrimargus musicus (Yellow-winged locust), Austracris guttulosa (Spur-throated locust), Oxya yezoensis, Oxya japonica, Patanga succincta, etc.; Gryllotalpidae such as Gryllotalpa orientalis; Gryllidae such as Acheta domestica, Teleogryllus emma; Tettigoniidae such as Anabrus simplex.

[0296] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Brown leaf-cutting ant (Attacapiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes and other Camponotus spp., Pogonomyrmex occidentalis and other Pogonomyrmex spp., Wasmania auropunctata and other Wasmania spp., Anoplolepis gracilipes and other Formicidae; Vespidae such as Vespa mandarinia, Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae; Siricidae such as Urocerus gigas; Bethylidae.

[0297] Order Blattodea: Blattella germanica of the family Ectobiidae; Periplaneta fuliginosa, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Blatta orientalis, etc. of the family Blattidae; Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans, etc. of the family Termitidae.

[0298] Order Siphonaptera: Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Echidnophaga gallinacea; Hectopsyllidae such as Tunga penetrans; Ceratophyllidae such as Nosopsyllus fasciatus.

[0299] Psocodae: Pediculidae such as Pediculus humanus capitis; Pthiridae such as Pthirus pubis; Haematopinidae such as Haematopinus eurysternus, Haematopinus suis; Linognathidae such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicoliidae such as Bovicola bovis, Bovicola ovis, Bovicola breviceps, Damalinia forficula, Werneckiella spp.; Trichodectidae such as Trichodectes canis, Felicola subrostratus; Menoponidae such as Menopon gallinae, Menacanthus stramineus, Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelididae such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, Liposcelis entomophila.

[0300] Thysanura: Lepismatidae such as Ctenolepisma villosa, Lepisma saccharina.

[0301] Order Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.; Eriophyidae such as Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri, Aceria tosichella, Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae;Ticks of the family Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus, etc.; Argasidae such as Argas persicus, Ornithodoros hermsi, Ornithodoros turicata, etc.; Acaridae such as Tyrophagus putrescentiae, Tyrophagus similis, etc.; Pyroglyphidae such as Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc.; Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella yasguri, etc.;Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp.; Sarcoptidae such as Notoedres cati, Notoedres muris, Sarcoptes scabiei; Listrophoridae such as Listrophorus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum, Ornithonyssus bacoti; Varroidae such as Varroa jacobsoni; Demodicidae such as Demodex canis, Demodex cati; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellare.

[0302] Order Araneae: Eutichuridae such as Cheiracanthium japonicum; Theridiidae such as Latrodectus hasseltii.

[0303] Order Polydesmida: Paradoxosomatidae such as Oxidus gracilis, Nedyopus tambanus.

[0304] Order Isopoda: Armadillidiidae such as Armadillidium vulgare.

[0305] Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus.

[0306] Gastropoda: Limacidae such as Limax marginatus and Limax flavus; Philomycidae such as Meghimatium bilineatum; Ampullariidae such as Pomacea canaliculata; Lymnaeidae such as Austropeplea ollula.

[0307] Nematoda: Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, Radopholus similis; Heteroderidae such as Meloidogyne javanica, Meloidogyne incognita, guava root - knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, Globodera rostochiensis, Globodera pallida, Meloidogyne chitwoodi; Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as Nothotylenchus acris, Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as Xiphinema index; Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus.

[0308] Harmful arthropods such as harmful insects and harmful mites, harmful mollusks and harmful nematodes can also be harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes with reduced sensitivity to pesticides, acaricides, molluscicides or nematicides, or with strong drug resistance.

[0309] As a method for controlling harmful arthropods of the present invention, it can be implemented by directly applying an effective amount of the compound or composition A of the present invention to harmful arthropods and / or to the habitats of harmful arthropods (plants, soil, indoors of houses, animals, etc.). As a method for controlling harmful arthropods of the present invention, for example, foliar treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment can be mentioned.

[0310] For the compound or composition A of the present invention, generally, inactive carriers such as solid carriers, liquid carriers, and gaseous carriers, and surfactants are mixed, and formulation aids such as binders, dispersants, and stabilizers are added as needed, and formulated into aqueous suspension formulations, oily suspension formulations, oil formulations, emulsion formulations, emulsion preparations, microemulsion formulations, microcapsule formulations, wettable powders, water-dispersible granules, powders, granules, tablets, aerosol formulations, resin formulations, etc. for use. It is not limited to these formulations, and it can be formulated into the dosage forms described in Manual on development and use of FAO and WHOSpecifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications (Manual on development and use of FAO and WHOSpecifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications), 2016, ISSN: 0259 - 2517 for use.

[0311] In these formulations, the compound or composition A of the present invention is usually contained in an amount of 0.0001 to 99% by weight.

[0312] Examples of the solid carrier include clays (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, palygorskite, silica white, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granular materials of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0313] Examples of the liquid carrier include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylene ethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0314] Examples of the gaseous carrier include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0315] Examples of the surfactant include nonionic surfactants (polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, etc.) and anionic surfactants (alkyl sulfonate, alkyl aryl sulfonate, alkyl sulfate, etc.).

[0316] Examples of the other adjuvants for the preparation include binders, dispersants, colorants, stabilizers, etc. Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, and butylated hydroxytoluene.

[0317] In addition, as a component for enhancing or assisting the efficacy of the active ingredient, an adjuvant can be used. Specifically, examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark), etc.

[0318] In the present invention, examples of the plant include the whole plant, stem and leaf, flower, spike, fruit, trunk, branch, crown, seed, vegetative propagation organ, and seedling.

[0319] The vegetative propagation organ refers to a part of the root, stem, leaf, etc. of a plant that has the ability to grow when the part is cut off from the main body and placed in the soil. Examples of the vegetative propagation organ include, for example, tuberous root, creeping root, bulb, corm (or solid bulb), tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. It should be noted that the stolon is sometimes also referred to as a runner, and the propagule is also referred to as a bulblet, which is divided into a broad bud and a bulbil. The vine cutting refers to the slender shoots (the general term for leaves and stems, shoot without roots) of sweet potato, Dioscorea japonica, etc. The bulb, corm, tuber, rhizome, cane cuttings, rhizophore, or tuberous root are also collectively referred to as a bulb. The cultivation of potatoes starts by implanting tubers into the soil, but the tubers used are usually referred to as seed potatoes.

[0320] As a method of applying an effective amount of the compound or composition A of the present invention to soil for controlling harmful arthropods, for example, a method of applying an effective amount of the compound or composition A of the present invention to the soil before or after transplanting plants can be mentioned. More specifically, for example, hole treatment (hole spraying, hole soil mixing), root treatment (root spraying, root soil mixing, root perfusion, late-stage root treatment during seedling raising), furrow treatment (furrow spraying, furrow soil mixing), ridge treatment (ridge spraying, ridge soil mixing, ridge spraying during the growth period), furrow treatment at sowing time (furrow spraying at sowing time, furrow soil mixing at sowing time), overall treatment (whole soil spraying, whole soil mixing), side treatment of ridge cultivation, water surface treatment (water surface application, water surface application after water storage), other soil spraying treatments (granule foliar spraying during the growth period, spraying under the canopy or around the trunk, soil surface spraying, soil surface mixing, hole spraying, surface spraying of the ridge part, inter-plant spraying), other perfusion treatments (soil perfusion, perfusion during seedling raising, liquid injection treatment, plant base perfusion, drip irrigation of liquid medicine, chemical solution irrigation), seedling box treatment (seedling box spraying, seedling box perfusion, liquid medicine accumulation in the seedling box), seedling tray treatment (seedling tray spraying, seedling tray perfusion, liquid medicine accumulation in the seedling tray), seedbed treatment (seedbed spraying, seedbed perfusion, seedbed spraying in the paddy field nursery, seedling dipping), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, spraying before covering soil at sowing time, spraying after covering soil at sowing time, covering soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, soil mixing at the rain dripping part, planting position treatment, granule calyx spraying, paste fertilizer mixing).

[0321] As seed treatment, for example, treatment of seeds or vegetative propagation organs with the compound or composition A of the present invention can be mentioned. Specifically, for example: spraying treatment in which a suspension of the compound or composition A of the present invention is atomized and sprayed onto the surface of seeds or vegetative propagation organs; coating treatment in which the compound or composition A of the present invention is coated on seeds or vegetative propagation organs; dipping treatment in which seeds or vegetative propagation organs are dipped in a liquid medicine of the compound or composition A of the present invention for a certain period of time; a method of coating seeds or vegetative propagation organs with a carrier containing the compound or composition A of the present invention (coating treatment, pellet coating treatment, etc.). As the above-mentioned vegetative propagation organs, seed potatoes can be particularly mentioned.

[0322] When treating seeds or vegetative propagation organs with Composition A, Composition A can be formulated into a single preparation for treating seeds or vegetative propagation organs, or can be formulated into different multiple preparations and applied to seeds or vegetative propagation organs in several times. As a method of formulating Composition A into different multiple preparations and applying them in several times, for example, there can be mentioned: treating with a preparation containing only the compound of the present invention as an active ingredient, allowing the seeds or vegetative propagation organs to air-dry, and then treating with a preparation containing this ingredient; and treating with a preparation containing the compound of the present invention and this ingredient as active ingredients, allowing the seeds or vegetative propagation organs to air-dry, and then treating with a preparation containing this ingredient other than the ingredient that has been treated.

[0323] The seeds or vegetative propagation organs retaining the compound of the present invention or Composition A in the present invention refer to: seeds or vegetative propagation organs in a state where the compound of the present invention or Composition A adheres to the surface of the seeds or vegetative propagation organs. For the above-mentioned seeds or vegetative propagation organs retaining the compound of the present invention or Composition A, materials other than the compound of the present invention or Composition A can be adhered before or after adhering the compound of the present invention or Composition A to the seeds or vegetative propagation organs.

[0324] In addition, when Composition A forms a layer and adheres to the surface of seeds or vegetative propagation organs, the layer is formed of one layer or multiple layers. In addition, when formed of multiple layers, each layer is a layer containing one or more active ingredients, or is formed of a layer containing one or more active ingredients and a layer not containing active ingredients.

[0325] Seeds or vegetative propagation organs retaining the compound of the present invention or Composition A can be obtained, for example, by the following method: applying a preparation containing the compound of the present invention or Composition A to seeds or vegetative propagation organs using the aforementioned seed treatment method.

[0326] When using the compound of the present invention or Composition A for controlling harmful arthropods in the agricultural field, the application rate is usually 1 to 10,000 g based on the amount of the compound of the present invention per 10,000 m 2 . When treating seeds or vegetative propagation organs, the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g relative to 1 Kg of seeds or vegetative propagation organs. When the compound of the present invention or Composition A is formulated into an emulsion, wettable powder, suspension agent, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm and applied, and granule agents, powder agents, etc. are usually applied directly.

[0327] In addition, the compound or composition A of the present invention can also be treated by methods such as winding a resin preparation processed into a sheet or line around a crop, stretching it near the crop, or laying it on the root soil.

[0328] When the compound or composition A of the present invention is used for controlling harmful arthropods inhabiting in a house, for its application amount, in the case of surface treatment, based on the amount of the compound of the present invention per 1 m 2 of the treated area, it is usually 0.01 - 1000 mg, and in the case of space treatment, based on the amount of the compound of the present invention per 1 m 3 of the treated space, it is usually 0.01 - 500 mg. When the compound or composition A of the present invention is formulated into an emulsion, wettable powder, suspension agent, etc., it is usually diluted with water so that the effective ingredient concentration becomes 0.1 - 10000 ppm and applied, and oil agents, aerosol agents, fumigants, bait agents, etc. are applied directly.

[0329] When the compound or composition A of the present invention is used for controlling external parasites of livestock such as cattle, horses, pigs, sheep, goats, chickens, and small animals such as dogs, cats, rats, and mice, it can be used for animals by methods known in veterinary medicine. As specific usage methods, for the purpose of systemic inhibition, it is administered by, for example, tablets, mixing into feed, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and for the purpose of non-systemic inhibition, it is used by methods such as spraying an oil agent or aqueous liquid, pouring treatment or drip treatment, washing the animal with a shampoo preparation, or making a resin preparation into a collar, ear tag and having the animal wear it. The amount of the compound or composition A of the present invention when administered to an animal is usually in the range of 0.1 - 1000 mg relative to 1 kg of the animal's body weight.

[0330] The compound or composition A of the present invention can be used as a control agent for harmful arthropods in agricultural lands such as dry fields, paddy fields, lawns, and orchards. As plants, for example, the following plants can be cited.

[0331] Maize (dent corn, flint corn, soft corn, pop corn, waxy corn, sweet corn, non-sweet corn), rice (long-grain rice, short-grain rice, medium-grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct seeding, transplantation, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, their respective winter wheat types, spring wheat types), barley (two-row barley (= brewing barley), six-row barley, naked barley, sticky barley, their respective winter barley types, spring barley types), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland cotton, pima cotton), soybean (mature seed harvest variety, edamame variety, green manure variety, their respective indeterminate growth type, determinate growth type, semi-determinate growth type), peanut, buckwheat, sugar beet (for sugar production, for feed, root vegetable, leaf vegetable, for fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (for oil extraction, for food, for ornamental use), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, spring chrysanthemum, artichoke, lettuce, etc.), liliaceous vegetables (scallion, onion, garlic, asparagus, etc.), umbelliferous vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceous vegetables (spinach, chard, etc.), labiatae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, Japanese yam, taro, pome fruits (apple, European pear, Japanese pear, white pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, ume, cherry, apricot, prune, etc.), citrus fruits (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date palm, coconut, ornamental plants, forest plants, turf grasses, forage grasses.

[0332] The above-mentioned plants may be any commonly cultivated varieties without particular limitation. The above-mentioned plants also include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred tolerance to HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, herbicides such as bromoxynil or dicamba; plants that can synthesize selective toxins known in Bacillus species such as Bacillus thuringiensis; plants that can confer specific insecticidal activity by synthesizing gene fragments partially identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insects.

[0333] Examples

[0334] Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples only.

[0335] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, Bu represents butyl, t-Bu represents tert-butyl, C2F5 represents perfluoroethyl, c-Pr represents cyclopropyl, c-Bu represents cyclobutyl, c-C5H9 represents cyclopentyl, c-C6H 11 represents cyclohexyl, Ph represents phenyl, Py2 represents 2-pyridyl, Py3 represents 3-pyridyl, and Py4 represents 4-pyridyl. When c-Pr, Ph, Py2, Py3, and Py4 have substituents, the substituents and the substitution positions are described together before the symbol. For example, 1-CN-c-Pr represents 1-cyanocyclopropyl, 3-F-Ph represents 3-fluorophenyl, 3,4,5-(OCH3)3-Ph represents 3,4,5-trimethoxyphenyl, and 5-CF3-Py2 represents 5-(trifluoromethyl)-2-pyridyl.

[0336] First, production examples of the compounds of the present invention and their production intermediates are shown.

[0337] Reference Production Example 1

[0338] To a mixture of 0.83 g of 5,6-dichloro-1-naphthol, 0.92 g of ethyl 5-(bromomethyl)isoxazole-3-carboxylate and 5 mL of DMF was added 0.81 g of potassium carbonate, and the mixture was stirred at room temperature for 21 hours. Water was added to the resulting mixture, and extraction was carried out using methyl tert-butyl ether (hereinafter referred to as MTBE). The resulting organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate = 3:1) to obtain 0.95 g of Intermediate 1 represented by the following formula.

[0339]

[0340] Intermediate 1: 1 1H-NMR (CDCl3) δ: 8.14 (1H, d), 7.94 (1H, d), 7.54 (1H, t), 7.52 (1H, d), 6.94 (1H, d), 6.84 (1H, s), 5.40 (2H, s), 4.47 (2H, q), 1.43 (3H, t).

[0341] Reference Production Example 1-1

[0342] The compounds produced according to Reference Production Example 1 and their physical property values are shown below.

[0343]

[0344] Intermediate 2: 1 1H-NMR (CDCl3) δ: 7.51 - 7.42 (2H, m), 7.38 (1H, s), 7.26 - 7.20 (1H, m), 6.98 - 6.92 (2H, m), 6.81 (1H, s), 6.70 (1H, dt), 5.26 (2H, s), 4.46 (2H, q), 1.42 (3H, t).

[0345] Reference Production Example 2

[0346] To a mixture of 0.95 g of Intermediate 1 and 20 mL of THF was added 5 mL of 1 mol / L aqueous sodium hydroxide solution, and the mixture was stirred for 18 hours. 10% Hydrochloric acid was added to the resulting mixture, and extraction was carried out using MTBE. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.88 g of Intermediate 3 represented by the following formula.

[0347]

[0348] Intermediate 3: 11H-NMR (CDCl3) δ: 8.14 (1H, d), 7.95 (1H, d), 7.56 - 7.51 (2H, m), 6.95 (1H, d), 6.90 (1H, s), 5.42 (2H, s).

[0349] Reference Production Example 2-1

[0350] The compounds produced according to Reference Production Example 2 and their physical property values are shown below.

[0351]

[0352] Intermediate 4: 1 1H-NMR (CDCl3) δ: 7.51 - 7.44 (2H, m), 7.38 (1H, s), 7.26 - 7.21 (1H, m), 6.99 - 6.93 (2H, m), 6.85 (1H, s), 6.71 (1H, dt), 5.27 (2H, s).

[0353] Reference Production Example 3

[0354] To a mixture of 0.40 g of Intermediate 3, 0.45 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.02 g of 1-hydroxybenzotriazole, and 10 mL of chloroform was added 0.30 g of 1-(methylamino)cyclopentanemethanamine, and the mixture was stirred at room temperature for 17 hours. The resulting mixture was concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (chloroform:methanol = 10:1) to obtain 0.40 g of Intermediate 5 represented by the following formula.

[0355]

[0356] Intermediate 5: 1 1H-NMR (CDCl3) δ: 8.15 (1H, d), 7.93 (1H, d), 7.53 (1H, t), 7.51 (1H, d), 7.44 (1H, s), 6.94 (1H, d), 6.88 (1H, s), 5.38 (2H, s), 3.40 (2H, d), 2.32 (3H, s), 1.76 - 1.34 (9H, m).

[0357] Reference Production Example 3-1

[0358] The compounds produced according to Reference Production Example 3 and their physical property values are shown below.

[0359]

[0360] Intermediate 6: 11H-NMR (DMSO-D6) δ: 8.52 (1H, s), 8.17 (1H, d), 7.83 (1H, d), 7.72 - 7.68 (2H, m), 7.34 (1H, d), 7.10 (1H, s), 5.61 (2H, s), 3.23 (2H, br), 2.28 (3H, s), 1.05 (6H, s).

[0361]

[0362] Intermediate 7: 1 1H-NMR (CDCl3) δ: 7.72 (1H, s), 7.50 - 7.43 (2H, m), 7.38 (1H, s), 7.26 - 7.20 (1H, m), 6.98 - 6.91 (2H, m), 6.82 (1H, s), 6.70 (1H, dt), 5.24 (2H, s), 4.65 (1H, s), 3.72 (2H, d), 1.89 - 1.64 (8H, m), 1.45 (9H, s).

[0363] Reference Production Example 4

[0364] To a mixture of 0.74 g of Intermediate 7 and 20 mL of chloroform was added 2 mL of trifluoroacetic acid, and the mixture was stirred at room temperature for 4 hours and 30 minutes. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (chloroform:methanol = 10:1) to obtain 0.57 g of Intermediate 8 represented by the following formula.

[0365]

[0366] Intermediate 8: 1 1H-NMR (CDCl3) δ: 7.51 - 7.44 (2H, m), 7.38 (2H, s), 7.26 - 7.21 (1H, m), 6.99 - 6.92 (2H, m), 6.83 (1H, s), 6.70 (1H, dt), 5.24 (2H, s), 3.41 (2H, d), 1.86 - 1.61 (6H, m), 1.54 - 1.43 (2H, m), 1.42 - 1.24 (2H, m).

[0367] Reference Production Example 5

[0368] To a mixture of 1.05 g of 5-bromo-2-(difluoromethyl)benzofuran, 1.62 g of bis(pinacolato)diboron, 1.25 g of potassium acetate, and 20 mL of dimethoxyethane was added 0.31 g of 1,1'-bis(diphenylphosphino)ferrocene palladium(II) dichloride, and the mixture was stirred at 80 °C for 3 hours and 30 minutes. After cooling to room temperature, water was added to the resulting mixture, and extraction was carried out using MTBE. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate = 10:1) to obtain 0.74 g of Intermediate 9 shown by the following formula.

[0369]

[0370] Intermediate 9: 1 H-NMR (CDCl3) δ: 8.14 (1H, s), 7.84 (1H, d), 7.53 (1H, d), 7.02 (1H, s), 6.75 (1H, t), 1.37 (12H, s).

[0371] Reference Production Example 5-1

[0372] The compounds produced according to Reference Production Example 5 and their physical property values are shown below.

[0373]

[0374] Intermediate 10: 1 H-NMR (CDCl3) δ: 8.75 (1H, dd), 8.12 (1H, dd), 7.84 (1H, dd), 5.99 (1H, s), 2.65 (3H, s), 2.30 (3H, s), 1.36 (12H, s).

[0375] Reference Production Example 6

[0376] To a mixture of 0.74 g of Intermediate 9, 0.59 g of ethyl 5-(bromomethyl)isoxazole-4-carboxylate, 1.04 g of potassium carbonate, 20 mL of toluene, and 4 mL of water was added 0.29 g of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred under heating to reflux for 1 hour. After cooling to room temperature, water was added to the resulting mixture, and extraction was carried out using MTBE. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate = 5:1) to obtain 0.42 g of Intermediate 11 shown by the following formula.

[0377]

[0378] Intermediate 11: 11H-NMR (CDCl3) δ: 7.53 (1H, s), 7.52 (1H, d), 7.28 (1H, d), 7.00 (1H, s), 6.75 (1H, t), 6.33 (1H, s), 4.41 (2H, q), 4.24 (2H, s), 1.39 (3H, t).

[0379] Reference Production Example 6-1

[0380] The compounds produced according to Reference Production Example 6 and their physical property values are shown below.

[0381]

[0382] In the compound represented by formula (A-1), (CH2) p -Y-Q is a compound as described in any one of [Table A-1].

[0383] [Table A-1]

[0384] Intermediate <![CDATA[(CH2) p -Y-Q]]> 11 <![CDATA[CH2-[4-(pyrazol-1-yl)-Ph]]]> 12 <![CDATA[CH2-[6-(pyrazol-1-yl)-Py3]]]> 13 <![CDATA[CH2-4-Ph-Ph]]> 14 <![CDATA[CH2CH=CH-3,4-Me2-Ph]]> 15 <![CDATA[CH2-4-Py2-Ph]]> 16 <![CDATA[CH2-[6-(3,5-Dimethyl-pyrazol-1-yl)-Py3]]]>

[0385] Intermediate 11: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.73 (1H, d), 7.68 (2H, d), 7.34 (2H, d), 6.48 (1H, t), 6.36 (1H, s), 4.42 (2H, q), 4.17 (2H, s), 1.40 (3H, t).

[0386] Intermediate 12: 1 1H-NMR (CDCl3) δ: 8.57 (1H, d), 8.33 (1H, d), 7.98 (1H, d), 7.74 (1H, d), 7.72 (1H, dd), 6.48 (1H, dd), 6.41 (1H, s), 4.43 (2H, q), 4.18 (2H, s), 1.40 (3H, t).

[0387] Intermediate 13: 1 1H-NMR (CDCl3) δ: 7.61 - 7.52 (4H, m), 7.48 - 7.41 (2H, m), 7.39 - 7.29 (3H, m), 6.39 (1H, s), 4.42 (2H, q), 4.18 (2H, s), 1.40 (3H, t).

[0388] Intermediate 14: 11H-NMR (CDCl3) δ: 7.15 (1H, s), 7.13 - 7.06 (2H, m), 6.51 (1H, d), 6.48 (1H, s), 6.21 (1H, dt), 4.43 (2H, q), 3.70 (2H, d), 2.26 (3H, s), 2.25 (3H, s), 1.41 (3H, t).

[0389] Intermediate 15: 1 1H-NMR (CDCl3) δ: 8.72 - 8.66 (1H, m), 7.98 (2H, d), 7.80 - 7.78 (2H, m), 7.37 (2H, d), 7.27 - 7.21 (1H, m), 6.36 (1H, s), 4.42 (2H, q), 4.19 (2H, s), 1.39 (3H, t).

[0390] Intermediate 16: 1 1H-NMR (CDCl3) δ: 8.32 (1H, d), 7.85 (1H, d), 7.67 (1H, dd), 6.39 (1H, s), 6.00 (1H, s), 4.42 (2H, q), 4.16 (2H, s), 2.63 (3H, s), 2.30 (3H, s), 1.40 (3H, t).

[0391] Reference Production Example 7

[0392] The compounds produced according to Reference Production Example 2 and their physical property values are shown below.

[0393]

[0394] In the compound represented by formula (A-2), (CH2) p -Y-Q is a compound as described in any one of [Table A-2].

[0395] [Table A-2]

[0396] Intermediate <![CDATA[(CH2) p -Y-Q]]> 17 <![CDATA[CH2-[4-(pyrazol-1-yl)-Ph]]]> 18 <![CDATA[CH2CH=CH-3,4-Me2-Ph]]> 19 <![CDATA[CH2-4-Py2-Ph]]> 20 <![CDATA[CH2-[2-CHF2-benzofuran-5-yl]]]> 21 <![CDATA[CH2O-3-F-5-C≡CH-Ph]]>

[0397] Intermediate 17: 1 1H-NMR (CDCl3) δ: 7.92 (1H, d), 7.76 (1H, d), 7.68 (2H, d), 7.35 (2H, d), 6.49 (1H, t), 6.41 (1H, s), 4.19 (2H.s).

[0398] Intermediate 18: 11H-NMR (CDCl3) δ: 7.16 (1H, s), 7.13 - 7.06 (2H, m), 6.54 (1H, s), 6.53 (1H, d), 6.21 (1H, dt), 3.73 (2H, d), 2.26 (3H, s), 2.25 (3H, s).

[0399] Intermediate 19: 1 1H-NMR (DMSO-D6) δ: 8.68 - 8.63 (1H, m), 8.07 (2H, d), 7.93 (1H, dt), 7.88 (1H, td), 7.42 (2H, d), 7.34 (1H, ddd), 6.60 (1H, s), 4.28 (2H, s).

[0400] Intermediate 20: 1 1H-NMR (CDCl3) δ: 7.55 - 7.50 (2H, m), 7.28 (1H, dd), 7.00 (1H, s), 6.75 (1H, t), 6.39 (1H, s), 4.26 (2H, s).

[0401] Intermediate 21: 1 1H-NMR (DMSO-D6) δ: 7.10 (1H, dt), 7.05 (1H, s), 7.02 - 6.98 (1H, m), 6.98 (1H, s), 5.41 (2H, s), 4.36 (1H, s).

[0402] Reference Production Example 8

[0403] The compounds produced according to Reference Production Example 3 and their physical property values are shown below.

[0404]

[0405] In the compound represented by formula (A-3), R 1 , R 4 , R 5 and the combination of (CH2) p -Y-Q are compounds with any combination described in [Table A-3].

[0406] [Table A-3]

[0407]

[0408] Intermediate 22: 1H-NMR(CDCl3) δ: 8.45 - 8.36 (1H, m), 6.42 (1H, s), 3.35 (2H, d), 2.78 (2H, t), 2.16 (3H, s), 1.74 - 1.65 (2H, m), 1.45 - 1.35 (2H, m), 1.02 (6H, s), 0.94 (3H, t).

[0409] Intermediate 23: 1 H-NMR(CDCl3) δ: 7.46 - 7.34 (1H, m), 7.14 (4H, s), 6.36 (1H, s), 4.07 (2H, s), 3.35 (2H, d), 2.53 (2H, q), 2.33 (3H, s), 1.78 - 1.46 (9H, m), 1.08 (3H, t).

[0410] Intermediate 24: 1 H-NMR(CDCl3) δ: 7.91 (1H, d), 7.72 (1H, d), 7.69 - 7.55 (3H, m), 7.32 (2H, d), 6.47 (1H, t), 6.43 (1H, s), 4.13 (2H, s), 3.47 (2H, d), 2.40 (3H, s), 1.80 - 1.55 (8H, m).

[0411] Intermediate 25: 1 H-NMR(CDCl3) δ: 8.47 (1H, d), 7.68 - 7.53 (1H, m), 6.82 (1H, d), 3.36 (2H, d), 2.96 - 2.84 (1H, m), 1.76 - 1.53 (8H, m), 1.08 (6H, d).

[0412] Intermediate 26: 1 H-NMR(CDCl3) δ: 7.91 (1H, d), 7.73 (1H, d), 7.67 (2H, d), 7.56 - 7.48 (1H, m), 7.34 (2H, d), 6.47 (1H, dd), 6.42 (1H, s), 4.15 (2H, s), 3.33 (2H, d), 2.93 - 2.83 (1H, m), 1.74 - 1.45 (9H, m), 1.06 (6H, d).

[0413] Intermediate 27: 11H-NMR (CDCl3) δ: 8.13 (1H, d), 7.91 (1H, d), 7.62 (1H, s), 7.53 - 7.49 (2H, m), 6.93 (1H, d), 6.88 (1H, s), 5.37 (2H, s), 3.36 (2H, d), 2.93 - 2.87 (1H, m), 1.72 - 1.56 (8H, m), 1.09 (3H, s), 1.07 (3H, s).

[0414] Intermediate 28: 1 1H-NMR (CDCl3) δ: 7.50 (1H, s), 7.14 (4H, s), 6.36 (1H, s), 4.06 (2H, s), 3.33 (2H, d), 2.91 - 2.85 (1H, m), 2.33 (3H, s), 1.71 - 1.53 (8H, m), 1.07 (3H, s), 1.05 (3H, s).

[0415] Intermediate 29: 1 1H-NMR (CDCl3) δ: 7.52 (1H, s), 7.30 - 7.28 (2H, m), 7.24 - 7.17 (3H, m), 6.45 (1H, s), 3.35 (2H, d), 2.93 - 2.86 (1H, m), 2.80 (2H, t), 2.69 (2H, t), 2.09 - 2.01 (2H, m), 1.71 - 1.55 (8H, m), 1.08 (3H, s), 1.06 (3H, s).

[0416] Intermediate 30: 1 1H-NMR (CDCl3) δ: 7.52 (1H, s), 7.14 (1H, s), 7.11 - 7.06 (2H, m), 6.52 - 6.48 (2H, m), 6.24 - 6.16 (1H, m), 3.68 (2H, d), 3.35 (2H, d), 2.92 - 2.86 (1H, m), 2.25 (6H, s), 1.70 - 1.56 (8H, m), 1.08 (3H, s), 1.06 (3H, s).

[0417] Intermediate 31: 1 1H-NMR (CDCl3) δ: 7.53 (1H, s), 6.43 (1H, s), 3.35 (2H, d), 2.93 - 2.87 (1H, m), 2.67 (2H, d), 2.11 - 2.00 (1H, m), 1.71 - 1.55 (8H, m), 1.08 (3H, s), 1.06 (3H, s), 0.98 (3H, s), 0.96 (3H, s).

[0418] Intermediate 32:1 1H-NMR (CDCl3) δ: 7.51 (1H, s), 7.35 - 7.29 (3H, m), 7.27 - 7.24 (2H, m), 6.38 (1H, t), 4.11 (2H, s), 3.33 (2H, d), 2.92 - 2.85 (1H, m), 1.70 - 1.53 (8H, m), 1.07 (3H, s), 1.05 (3H, s).

[0419] Intermediate 33: 1 1H-NMR (CDCl3) δ: 8.70 - 8.68 (1H, m), 7.98 - 7.95 (2H, m), 7.78 - 7.70 (2H, m), 7.52 (1H, s), 7.38 - 7.35 (2H, m), 7.25 - 7.21 (1H, m), 6.43 (1H, t), 4.17 (2H, s), 3.33 (2H, d), 2.92 - 2.85 (1H, m), 1.70 - 1.53 (8H, m), 1.07 (3H, s), 1.05 (3H, s).

[0420] Intermediate 34: 1 1H-NMR (CDCl3) δ: 7.52 - 7.49 (3H, m), 7.29 - 7.27 (1H, m), 6.99 (1H, s), 6.75 (1H, t), 6.39 (1H, s), 4.21 (2H, s), 3.33 (2H, d), 2.91 - 2.85 (1H, m), 1.69 - 1.54 (8H, m), 1.07 (3H, s), 1.05 (3H, s).

[0421] Intermediate 35: 1 1H-NMR (CDCl3) δ: 7.62 (1H, s), 7.48 - 7.45 (2H, m), 7.38 (1H, s), 7.24 - 7.22 (1H, m), 6.95 - 6.92 (2H, m), 6.82 (1H, s), 6.72 - 6.68 (1H, m), 5.24 (2H, s), 3.36 (2H, d), 2.93 - 2.87 (1H, m), 1.71 - 1.56 (8H, m), 1.09 (3H, s), 1.07 (3H, s).

[0422] Intermediate 36: 11H-NMR (CDCl3) δ: 7.59 (1H, s), 6.88 - 6.86 (2H, m), 6.79 (1H, s), 6.71 - 6.67 (1H, m), 5.17 (2H, s), 3.35 (2H, d), 3.11 (1H, s), 2.93 - 2.86 (1H, m), 1.72 - 1.56 (8H, m), 1.08 (3H, s), 1.07 (3H, s).

[0423] Intermediate 37: 1 1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.45 - 7.42 (2H, m), 7.19 - 7.16 (1H, m), 6.73 (1H, s), 4.67 (2H, s), 4.55 (2H, s), 3.35 (2H, d), 2.93 - 2.87 (1H, m), 1.71 - 1.55 (8H, m), 1.08 (3H, s), 1.07 (3H, s).

[0424] Reference Production Example 9

[0425] To 0.56 g of Intermediate 12 was added 0.59 g of 1-[(1-methylethyl)amino]cyclopentanemethanamine, and the mixture was stirred at 130 °C for 2 hours. After cooling to room temperature, the resulting mixture was concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (chloroform:methanol = 10:1) to obtain 0.58 g of Intermediate 38 represented by the following formula.

[0426]

[0427] Intermediate 38: 1 1H-NMR (CDCl3) δ: 8.54 (1H, d), 8.33 (1H, d), 7.97 (1H, d), 7.74 (1H, d), 7.72 (1H, dd), 7.58 - 7.50 (1H, m), 6.47 (1H, s), 6.46 (1H, s), 4.16 (2H, s), 3.33 (2H, d), 2.94 - 2.83 (1H, m), 1.74 - 1.48 (9H, m), 1.07 (6H, d).

[0428] Reference Production Example 9-1

[0429] The compounds produced according to Reference Production Example 9 and their physical property values are shown below.

[0430]

[0431] In the compound represented by formula (A-4), R 1 and (CH2) pThe combination of -Y-Q is a compound of any combination recorded in [Table A-4].

[0432] [Table A-4]

[0433] Intermediate <![CDATA[(CH2) p -Y-Q]]> <![CDATA[R 1 > 39 <![CDATA[CH2-4-Ph-Ph]]> i-Pr 4O <![CDATA[CH2-4-OCF3-Ph]]> i-Pr 41 <![CDATA[CH2-[6-(3,5-Dimethyl-pyrazol-1-yl)-Py3]]]> i-Pr 42 <![CDATA[CH2-[6-(3,5-Dimethyl-pyrazol-1-yl)-Py3]]]> Et 43 <![CDATA[CH2-[6-(3,5-Dimethyl-pyrazol-1-yl)-Py3]]]> Me

[0434] Intermediate 39: 1 H-NMR(CDCl3)δ: 7.59 - 7.50(5H, m), 7.47 - 7.41(2H, m), 7.37 - 7.30(3H, m), 6.43(1H, s), 4.15(2H, s), 3.33(2H, d), 2.92 - 2.85(1H, m), 1.70 - 1.53(8H, m), 1.07(3H, s), 1.05(3H, s).

[0435] Intermediate 40: 1 H-NMR(CDCl3)δ: 7.53(1H, s), 7.28(2H, d), 7.19(2H, d), 6.41(1H, s), 4.12(2H, s), 3.33(2H, d), 2.92 - 2.85(1H, m), 1.70 - 1.55(8H, m), 1.07(3H, s), 1.06(3H, s).

[0436] Intermediate 41: 1 H-NMR(CDCl3)δ: 8.33(1H, d), 7.83(1H, d), 7.67(1H, dd), 7.57 - 7.49(1H, m), 6.45(1H, s), 5.99(1H, s), 4.13(2H, s), 3.33(2H, d), 2.93 - 2.83(1H, m), 2.62(3H, s), 2.29(3H, s), 1.75 - 1.52(9H, m), 1.06(6H, d).

[0437] Intermediate 42: 1 H-NMR(CDCl3)δ: 8.32(1H, s), 7.83(1H, d), 7.66(1H, d), 7.49 - 7.39(1H, m), 6.45(1H, s), 5.99(1H, s), 4.14(2H, s), 3.36(2H, d), 2.62(3H, s), 2.54(2H, q), 2.29(3H, s), 1.76 - 1.47(9H, m), 1.09(3H, t).

[0438] Intermediate 43: 11H-NMR (CDCl3) δ: 8.32 (1H, d), 7.83 (1H, d), 7.66 (1H, dd), 7.40 - 7.30 (1H, m), 6.45 (1H, s), 5.99 (1H, s), 4.14 (2H, s), 3.38 (2H, d), 2.62 (3H, s), 2.30 (3H, s), 2.29 (3H, s), 1.74 - 1.40 (9H, m).

[0439] Production Example 1

[0440] To a mixture of 0.50 g of 5-butyl-N-[2-methyl-2-(methylamino)propyl]-3-isoxazolecarboxamide prepared by the method described in International Publication No. 2016 / 017467 and 22 mL of THF was added 0.59 g of paraformaldehyde, and the mixture was stirred under heating under reflux for 2 hours. The resulting mixture was filtered and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate = 1:1) to obtain 0.36 g of Compound 1 of the present invention represented by the following formula.

[0441]

[0442] Compound 1 of the present invention: 1 1H-NMR (CDCl3) δ: 6.43 (1H, d), 4.60 (1H, s), 4.40 (1H, s), 3.81 (1H, s), 3.54 (1H, s), 2.79 (2H, t), 2.29 (3H, d), 1.72 - 1.66 (2H, m), 1.45 - 1.36 (2H, m), 1.14 (3H, s), 1.12 (3H, s), 0.95 (3H, t).

[0443] Production Example 1-1

[0444] The compounds produced according to Production Example 1 and their physical property values are shown below.

[0445]

[0446] In the compound represented by the formula (B-1), R 1 , R 4 , R 5 , R 8 , R 9 and the combination of (CH2) p -Y-Q are compounds having any combination described in [Table B-1], [Table B-2], [Table B-3] and [Table B-4].

[0447] [Table B-1]

[0448]

[0449] [Table B-2]

[0450]

[0451] [Table B-3]

[0452]

[0453] [Table B-4]

[0454]

[0455] Compound 2 of the present invention: 1 H-NMR(CDCl3)δ:6.43(1H,d),4.86(1H,s),4.67(1H,s),3.65(1H,s),3.41(1H,s),2.79(2H,t),1.74-1.66(2H,m),1.45-1.36(2H,m),1.30(3H,s),1.28(3H,s),0.95(3H,t).

[0456] Compound 3 of the present invention: 1 H-NMR(CDCl3)δ:6.36(1H,d),4.50(1H,d),3.95(1H,d),3.40(1H,d),2.78(2H,t),2.29(3H,s),2.27-2.20(1H,m),1.74-1.66(2H,m),1.46-1.36(2H,m),1.14(3H,s),1.01(3H,d),0.99(3H,d),0.95(3H,t),0.90(3H,s).

[0457] Compound 4 of the present invention: 1 H-NMR(CDCl3)δ:6.38(1H,s),3.81(2H,s),2.78(2H,t),1.73(6H,s),1.72-1.64(2H,m),1.46-1.35(2H,m),1.31(6H,s),1.26(1H,s),0.95(3H,t).

[0458] Compound 5 of the present invention: 1 H-NMR(CDCl3)δ:7.53(1H,s),7.30(1H,s),6.43(1H,s),3.43(2H,d),2.78(2H,t),1.73-1.65(2H,m),1.46-1.35(2H,m),1.15(6H,s),1.06(9H,s),0.94(3H,t).

[0459] Compound 6 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, s), 7.31 (1H, s), 6.55 (1H, t), 3.42 (2H, d), 2.68 (2H, d), 1.15 (6H, s), 1.06 (10H, s), 0.63 - 0.59 (2H, m), 0.27 - 0.23 (2H, m).

[0460] Compound 7 of the present invention: 1 H-NMR (CDCl3) δ: 7.52 (1H, s), 7.36 - 7.24 (6H, m), 6.38 (1H, t), 4.10 (2H, s), 3.40 (2H, d), 1.13 (6H, s), 1.05 (9H, s).

[0461] Compound 8 of the present invention: 1 H-NMR (CDCl3) δ: 7.52 (1H, s), 7.33 - 7.29 (2H, m), 7.04 - 7.02 (1H, m), 7.01 - 6.94 (2H, m), 6.42 (1H, t), 4.11 (2H, s), 3.40 (2H, d), 1.14 (6H, s), 1.05 (9H, s).

[0462] Compound 9 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, s), 7.33 - 7.29 (3H, m), 6.97 - 6.94 (3H, m), 6.78 (1H, t), 5.18 (2H, s), 3.42 (2H, d), 1.15 (6H, s), 1.06 (9H, s).

[0463] Compound 10 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, s), 7.30 (1H, s), 6.42 (1H, t), 3.41 (2H, d), 2.77 (2H, t), 1.70 (2H, t), 1.32 - 1.26 (10H, m), 1.15 (6H, s), 1.06 (9H, s), 0.88 (3H, t).

[0464] Compound 11 of the present invention: 1 H-NMR (CDCl3) δ: 7.53 (1H, s), 7.34 (1H, s), 6.53 (1H, t), 3.42 (2H, d), 3.10 - 3.06 (2H, m), 2.60 - 2.48 (2H, m), 1.15 (6H, s), 1.06 (9H, s).

[0465] Compound 12 of the present invention: 1 H-NMR(CDCl3)δ: 7.53(1H, s), 7.35(1H, s), 6.85(1H, s), 6.79(2H, m), 6.70(1H, s), 5.97(2H, s), 4.64(2H, s), 4.50(2H, s), 3.42(2H, d), 1.15(6H, s), 1.06(9H, s).

[0466] Compound 13 of the present invention: 1 H-NMR(CDCl3)δ: 7.53(1H, s), 7.30(1H, s), 6.43(1H, t), 3.41(2H, d), 2.79(2H, t), 1.82 - 1.50(11H, m), 1.15(6H, s), 1.06(9H, s).

[0467] Compound 14 of the present invention: 8.14(1H, d), 7.92(1H, d), 7.54 - 7.49(2H, m), 6.95(1H, d), 6.88(1H, d), 5.38(2H, s), 4.63(1H, s), 4.41(1H, s), 3.83(1H, s), 3.56(1H, s), 2.30(3H, d), 1.14(6H, d).

[0468] Compound 15 of the present invention: 1 H-NMR(CDCl3)δ: 7.26(1H, s), 7.21(1H, s), 6.53(1H, s), 6.48(1H, s), 4.27(2H, s), 3.82(2H, s), 2.34(3H, s), 2.32(3H, s), 1.87 - 1.56(12H, m), 1.36 - 1.19(3H, m).

[0469] Compound 16 of the present invention: 1 H-NMR(CDCl3)δ: 7.26(1H, s), 7.21(1H, s), 6.58(1H, s), 6.48(1H, s), 4.61(1H, s), 4.41(1H, s), 4.27(2H, s), 3.82(1H, s), 3.57(1H, s), 2.54(2H, q), 2.34(3H, s), 2.32(3H, s), 1.83 - 1.49(8H, m), 1.15(3H, t).

[0470] Compound 17 of the present invention: 11H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.58 (1H, s), 6.47 (1H, s), 4.91 (1H, s), 4.27 (2H, s), 4.24 (2H, q), 4.09 (1H, d), 3.90 (1H, d), 2.88 - 2.60 (2H, m), 2.34 (3H, s), 2.31 (3H, s), 1.86 - 1.43 (8H, m), 1.29 (3H, t), 1.14 (3H, t).

[0471] Compound 18 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.54 (1H, s), 6.48 (1H, s), 5.03 (1H, q), 4.27 (2H, s), 3.86 (1H, d), 3.59 (1H, d), 3.21 - 3.07 (1H, m), 2.34 (3H, s), 2.32 (3H, s), 1.84 - 1.51 (6H, m), 1.50 - 1.29 (2H, m), 1.44 (3H, d), 1.15 (3H, d), 1.07 (3H, d).

[0472] Compound 19 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.54 (1H, s), 6.48 (1H, s), 4.66 (1H, q), 4.27 (2H, s), 3.94 (1H, d), 3.64 (1H, d), 2.77 - 2.65 (1H, m), 2.56 - 2.43 (1H, m), 2.34 (3H, s), 2.32 (3H, s), 1.83 - 1.48 (8H, m), 1.46 (3H, d), 1.15 (3H, t).

[0473] Compound 20 of the present invention: 1 1H-NMR (CDCl3) δ: 7.51 - 7.44 (1H, m), 7.17 (1H, s), 6.59 (1H, s), 6.53 (1H, s), 4.29 (2H, s), 3.37 (2H, d), 3.29 - 3.18 (1H, m), 2.49 (3H, s), 2.46 (3H, s), 2.21 (3H, s), 1.88 - 1.79 (2H, m), 1.72 - 1.56 (4H, m), 1.48 - 1.38 (2H, m), 1.04 (6H, d).

[0474] Compound 21 of the present invention: 11H-NMR (CDCl3) δ: 7.17 (1H, s), 6.60 (1H, s), 6.55 (1H, s), 4.77 (1H, s), 4.57 (1H, s), 4.29 (2H, s), 3.73 (1H, s), 3.49 (1H, s), 3.21 - 3.09 (1H, m), 2.49 (3H, s), 2.46 (3H, s), 1.85 - 1.69 (4H, m), 1.68 - 1.55 (4H, m), 1.08 (3H, d), 1.06 (3H, d).

[0475] Compound 22 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.57 (1H, s), 6.48 (1H, s), 4.77 (1H, s), 4.56 (1H, s), 4.27 (2H, s), 3.72 (1H, s), 3.48 (1H, s), 3.22 - 3.10 (1H, m), 2.34 (3H, s), 2.31 (3H, s), 1.85 - 1.55 (8H, m), 1.08 (3H, d), 1.05 (3H, d).

[0476] Compound 23 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.53 (1H, s), 6.48 (1H, s), 4.27 (1H, d), 4.27 (2H, s), 3.82 (1H, d), 3.68 (1H, d), 3.24 - 3.11 (1H, m), 2.34 (3H, s), 2.32 (3H, s), 1.92 - 1.37 (8H, m), 1.17 - 0.85 (8H, m), 0.58 - 0.22 (3H, m).

[0477] Compound 24 of the present invention: 1 1H-NMR (CDCl3) δ: 7.17 (1H, s), 6.56 (1H, s), 6.55 (1H, s), 4.62 (1H, d), 4.28 (2H, s), 3.83 (1H, d), 3.69 (1H, d), 3.25 - 3.10 (1H, m), 2.49 (3H, s), 2.46 (3H, s), 1.97 - 0.85 (16H, m), 0.58 - 0.22 (3H, m).

[0478] Compound 25 of the present invention: 1H-NMR(CDCl3) δ: 7.26(1H, s), 7.21(1H, s), 6.52(1H, s), 6.48(1H, s), 4.31(1H, d), 4.27(2H, s), 3.91(1H, d), 3.65(1H, d), 2.89 - 2.78(1H, m), 2.58 - 2.46(1H, m), 2.34(3H, s), 2.32(3H, s), 1.86 - 1.60(5H, m), 1.58 - 1.41(2H, m), 1.35 - 1.24(1H, m), 1.16(3H, t), 1.08 - 0.85(2H, m), 0.60 - 0.09(3H, m).

[0479] Compound 26 of the present invention: 1 H-NMR(CDCl3) δ: 7.17(1H, s), 6.55(2H, s), 4.31(1H, d), 4.28(2H, s), 3.92(1H, d), 3.66(1H, d), 2.90 - 2.78(1H, m), 2.58 - 2.50(1H, m), 2.49(3H, s), 2.46(3H, s), 1.88 - 1.60(5H, m), 1.58 - 1.43(2H, m), 1.37 - 1.23(1H, m), 1.16(3H, t), 1.09 - 0.85(2H, m), 0.63 - 0.21(3H, m).

[0480] Compound 27 of the present invention: 1 H-NMR(CDCl3) δ: 7.17(1H, s), 6.60(1H, s), 6.55(1H, s), 4.62(1H, s), 4.41(1H, s), 4.29(2H, s), 3.82(1H, s), 3.57(1H, s), 2.54(2H, q), 2.49(3H, s), 2.46(3H, s), 1.84 - 1.50(8H, m), 1.15(3H, t).

[0481] Compound 28 of the present invention: 1 H-NMR(CDCl3) δ: 7.26(1H, s), 7.21(1H, s), 6.54(1H, s), 6.48(1H, s), 5.04(1H, dd), 4.27(2H, s), 3.81(1H, d), 3.55(1H, d), 3.25 - 3.05(1H, m), 2.34(3H, s), 2.31(3H, s), 2.04 - 1.92(1H, m), 1.83 - 1.42(9H, m), 1.11(3H, d), 1.03(3H, d), 0.93(3H, t).

[0482] Compound 29 of the present invention: 1 H-NMR(CDCl3)δ: 7.17(1H, s), 6.55(1H, s), 6.52(1H, s), 4.72(1H, d), 4.29(2H, s), 3.97(1H, d), 3.43(1H, d), 2.95 - 2.74(1H, m), 2.66 - 2.51(1H, m), 2.49(3H, s), 2.46(3H, s), 2.14 - 2.02(1H, m), 1.94 - 1.36(6H, m), 1.21 - 0.77(11H, m).

[0483] Compound 30 of the present invention: 1 H-NMR(CDCl3)δ: 7.25(1H, s), 7.20(1H, s), 6.56(1H, s), 6.47(1H, s), 5.92 - 5.57(1H, m), 5.47 - 5.16(2H, m), 4.26(2H, s), 3.89(1H, d), 3.60(1H, d), 3.21 - 3.12(1H, m), 2.34(3H, s), 2.31(3H, s), 1.85 - 1.31(11H, m), 1.14 - 1.00(6H, m).

[0484] Compound 31 of the present invention: 1 H-NMR(CDCl3)δ: 7.26(1H, s), 7.21(1H, s), 6.50(1H, s), 6.49(1H, s), 4.71(1H, d), 4.27(2H, s), 3.96(1H, d), 3.42(1H, d), 2.8 - 2.73(1H, m), 2.57 - 2.46(1H, m), 2.34(3H, s), 2.32(3H, s), 2.13 - 2.02(1H, m), 1.83 - 1.40(8H, m), 1.11(3H, t), 1.02(3H, d), 0.99(3H, t).

[0485] Compound 32 of the present invention: 1 H-NMR(CDCl3)δ: 7.26(1H, s), 7.21(1H, s), 6.54(1H, s), 6.48(1H, s), 5.06(1H, dd), 4.27(2H, s), 3.79(1H, d), 3.56(1H, d), 3.27 - 3.09(1H, m), 2.34(3H, s), 2.32(3H, s), 1.96 - 1.19(12H, m), 1.14 - 0.80(9H, m).

[0486] Compound 33 of the present invention:1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.54 (1H, s), 6.48 (1H, s), 5.06 (1H, dd), 4.27 (2H, s), 3.78 (1H, d), 3.57 (1H, d), 3.27 - 3.09 (1H, m), 2.34 (3H, s), 2.32 (3H, s), 1.98 - 1.19 (14H, m), 1.13 - 0.80 (9H, m).

[0487] Compound 34 of the present invention: 1 1H-NMR (CDCl3) δ: 7.52 (1H, s), 7.44 (1H, s), 7.27 (1H, t), 7.21 (1H, t), 6.60 (1H, s), 6.58 (1H, s), 5.03 (1H, q), 4.31 (2H, s), 3.87 (1H, d), 3.60 (1H, d), 3.21 - 3.08 (1H, m), 1.83 - 1.37 (11H, m), 1.15 (3H, d), 1.07 (3H, d).

[0488] Compound 35 of the present invention: 1 1H-NMR (CDCl3) δ: 7.31 (1H, d), 7.30 (1H, s), 7.07 (1H, d), 6.57 (1H, s), 6.52 (1H, s), 5.03 (1H, q), 4.31 (2H, s), 3.87 (1H, d), 3.60 (1H, d), 3.21 - 3.08 (1H, m), 2.42 (3H, s), 1.83 - 1.37 (11H, m), 1.15 (3H, d), 1.07 (3H, d).

[0489] Compound 36 of the present invention: 1 1H-NMR (CDCl3) δ: 7.34 (1H, d), 7.32 (1H, s), 7.10 (1H, d), 6.56 (1H, s), 6.54 (1H, s), 5.03 (1H, q), 4.31 (2H, s), 3.86 (1H, d), 3.60 (1H, d), 3.21 - 3.08 (1H, m), 2.72 (2H, q), 1.83 - 1.40 (11H, m), 1.26 (3H, t), 1.15 (3H, d), 1.07 (3H, d).

[0490] Compound 37 of the present invention: 1H-NMR(CDCl3) δ: 7.36(1H, s), 7.35(1H, d), 7.14(1H, d), 6.56(1H, s), 6.55(1H, s), 5.03(1H, q), 4.29(2H, s), 3.86(1H, d), 3.59(1H, d), 3.21 - 3.08(1H, m), 3.05 - 2.93(1H, m), 1.82 - 1.37(11H, m), 1.28(6H, d), 1.15(3H, d), 1.07(3H, d).

[0491] Compound 38 of the present invention: 1 H-NMR(CDCl3) δ: 7.43(1H, dd), 7.16(1H, dd), 6.99(1H, td), 6.57(2H, s), 5.04(1H, q), 4.29(2H, s), 3.87(1H, d), 3.60(1H, d), 3.21 - 3.08(1H, m), 1.84 - 1.30(11H, m), 1.15(3H, d), 1.07(3H, d).

[0492] Compound 39 of the present invention: 1 H-NMR(CDCl3) δ: 7.49(1H, d), 7.35(1H, d), 7.23(1H, dd), 6.59(1H, s), 6.55(1H, s), 5.04(1H, q), 4.30(2H, s), 3.88(1H, d), 3.60(1H, d), 3.21 - 3.08(1H, m), 1.83 - 1.28(11H, m), 1.15(3H, d), 1.07(3H, d).

[0493] Compound 40 of the present invention: 1 H-NMR(CDCl3) δ: 7.37(1H, d), 6.98(1H, d), 6.85(1H, dd), 6.56(1H, s), 6.52(1H, s), 5.03(1H, q), 4.27(2H, s), 3.87(1H, d), 3.84(3H, s), 3.60(1H, d), 3.20 - 3.09(1H, m), 1.82 - 1.29(11H, m), 1.15(3H, d), 1.07(3H, d).

[0494] Compound 41 of the present invention: 1H-NMR(CDCl3) δ: 7.23(1H, s), 6.93(1H, s), 6.55(1H, s), 6.47(1H, s), 5.03(1H, q), 4.26(2H, s), 3.87(1H, d), 3.85(3H, s), 3.59(1H, d), 3.21 - 3.07(1H, m), 2.27(3H, s), 1.82 - 1.24(11H, m), 1.14(3H, d), 1.07(3H, d).

[0495] Compound 42 of the present invention: 1 H-NMR(CDCl3) δ: 7.38(1H, d), 7.24(1H, s), 7.04(1H, d), 6.56(1H, s), 6.54(1H, s), 5.03(1H, q), 4.28(2H, s), 3.87(1H, d), 3.60(1H, d), 3.21 - 3.09(1H, m), 2.46(3H, s), 1.82 - 1.30(11H, m), 1.15(3H, d), 1.07(3H, d).

[0496] Compound 43 of the present invention: 1 H-NMR(CDCl3) δ: 7.53(1H, s), 7.47(1H, s), 7.05(1H, s), 6.52(1H, s), 5.03(1H, q), 4.36(2H, s), 3.86(1H, d), 3.59(1H, d), 3.21 - 3.08(1H, m), 2.35(3H, s), 2.34(3H, s), 1.82 - 1.24(11H, m), 1.14(3H, d), 1.06(3H, d).

[0497] Compound 44 of the present invention: 1 H-NMR(CDCl3) δ: 7.51(1H, d), 7.23(1H, s), 7.12(1H, d), 6.53(1H, s), 5.03(1H, q), 4.39(2H, s), 3.86(1H, d), 3.59(1H, d), 3.22 - 3.08(1H, m), 2.47(3H, s), 2.38(3H, s), 1.85 - 1.25(11H, m), 1.14(3H, d), 1.06(3H, d).

[0498] Compound 45 of the present invention: 11H-NMR (CDCl3) δ: 7.10 (1H, s), 6.55 (1H, s), 6.54 (1H, s), 5.03 (1H, q), 4.27 (2H, s), 3.86 (1H, d), 3.59 (1H, d), 3.21 - 3.07 (1H, m), 2.39 (3H, s), 2.37 (3H, s), 2.23 (3H, s), 1.84 - 1.24 (11H, m), 1.14 (3H, d), 1.06 (3H, d).

[0499] Compound 46 of the present invention: 1 1H-NMR (CDCl3) δ: 7.07 (1H, s), 6.85 (1H, s), 6.56 (1H, s), 6.55 (1H, s), 5.03 (1H, q), 4.28 (2H, s), 3.87 (1H, d), 3.60 (1H, d), 3.23 - 3.08 (1H, m), 2.43 (3H, s), 2.41 (3H, s), 1.85 - 1.28 (11H, m), 1.15 (3H, d), 1.07 (3H, d).

[0500] Compound 47 of the present invention: 1 1H-NMR (CDCl3) δ: 7.49 (1H, s), 7.30 (1H, s), 6.57 (1H, s), 6.50 (1H, s), 5.03 (1H, q), 4.28 (2H, s), 3.87 (1H, d), 3.60 (1H, d), 3.22 - 3.08 (1H, m), 2.45 (3H, s), 1.84 - 1.28 (11H, m), 1.14 (3H, d), 1.07 (3H, d).

[0501] Compound 48 of the present invention: 1 1H-NMR (CDCl3) δ: 7.36 (1H, dd), 7.17 (1H, dd), 6.98 (1H, td), 6.58 (1H, s), 6.57 (1H, s), 5.03 (1H, q), 4.30 (2H, s), 3.88 (1H, d), 3.60 (1H, d), 3.21 - 3.08 (1H, m), 1.87 - 1.29 (11H, m), 1.15 (3H, d), 1.07 (3H, d).

[0502] Compound 49 of the present invention: 11H-NMR (CDCl3) δ: 7.48 (1H, s), 7.38 (1H, d), 7.24 (1H, m), 7.03 (1H, d), 6.58 (1H, t), 6.52 (1H, q), 4.28 (2H, s), 3.49 (2H, d), 2.45 (3H, s), 1.74 - 1.25 (8H, m), 1.06 (9H, s).

[0503] Compound 50 of the present invention: 1 1H-NMR (CDCl3) δ: 7.49 (1H, s), 7.48 - 7.46 (2H, m), 7.38 (1H, s), 7.33 (1H, s), 7.26 - 7.23 (1H, m), 6.96 - 6.92 (2H, m), 6.81 (1H, s), 6.72 - 6.68 (1H, m), 5.23 (2H, s), 3.50 (2H, d), 1.73 - 1.26 (8H, m), 1.07 (9H, s).

[0504] Compound 51 of the present invention: 1 1H-NMR (CDCl3) δ: 7.48 (1H, s), 7.28 - 7.22 (2H, m), 7.21 (1H, s), 6.57 (1H, t), 6.46 (1H, s), 4.26 (2H, s), 3.48 (2H, d), 2.34 (3H, s), 2.31 (3H, s), 1.75 - 1.55 (8H, m), 1.06 (9H, s).

[0505] Compound 52 of the present invention: 1 1H-NMR (CDCl3) δ: 7.17 (1H, s), 6.55 (1H, s), 6.52 (1H, s), 5.04 (1H, d), 4.28 (2H, s), 3.78 (1H, d), 3.58 (1H, d), 3.20 - 3.09 (1H, m), 2.66 - 2.52 (1H, m), 2.49 (3H, s), 2.46 (3H, s), 1.99 - 0.68 (20H, m).

[0506] Compound 53 of the present invention: 1 1H-NMR (CDCl3) δ: 7.17 (1H, s), 6.59 (1H, s), 6.55 (1H, s), 5.19 (1H, dd), 4.29 (2H, s), 3.87 (1H, d), 3.79 - 3.06 (7H, m), 2.49 (3H, s), 2.46 (3H, s), 1.84 - 1.41 (8H, m), 1.16 (3H, d), 1.02 (3H, d).

[0507] Compound 54 of the present invention: 1 H-NMR(CDCl3)δ: 7.33 - 7.09(6H, m), 6.57(1H, s), 6.56(1H, s), 5.23(1H, dd), 4.29(2H, s), 3.63(1H, d), 3.33 - 2.88(4H, m), 2.50(3H, s), 2.46(3H, s), 1.95 - 1.40(8H, m), 0.97(3H, d), 0.78(3H, d).

[0508] Compound 55 of the present invention: 1 H-NMR(CDCl3)δ: 8.16(1H, d), 7.93(1H, d), 7.53(1H, t), 7.51(1H, d), 6.96(1H, dd), 6.89(1H, d), 5.39(2H, s), 4.64(1H, s), 4.41(1H, s), 3.86(1H, s), 3.60(1H, s), 2.36(3H, s), 1.86 - 1.47(8H, m).

[0509] Compound 56 of the present invention: 1 H-NMR(CDCl3)δ: 6.36(1H, t), 4.44(1H, d), 4.02(1H, d), 3.40(1H, d), 2.78(2H, t), 2.31(3H, s), 2.27 - 2.19(1H, m), 1.74 - 1.38(12H, m), 1.02(6H, d), 0.95(3H, t).

[0510] Compound 57 of the present invention: 1 H-NMR(CDCl3)δ: 7.17 - 7.13(4H, m), 6.29(1H, s), 4.70(1H, d), 4.06(2H, s), 3.96(1H, d), 3.41(1H, d), 2.82 - 2.74(1H, m), 2.56 - 2.49(1H, m), 2.34(3H, s), 2.11 - 2.03(1H, m), 1.78 - 1.43(8H, m), 1.10(3H, t), 0.99(6H, d).

[0511] Compound 58 of the present invention: 1 H-NMR(CDCl3)δ: 7.49(1H, s), 7.28(1H, s), 7.17(1H, s), 6.59(1H, t), 6.53(1H, d), 4.28(2H, s), 3.49(2H, d), 2.49(3H, s), 2.46(3H, s), 1.69 - 1.61(8H, m), 1.06(9H, s).

[0512] Compound 59 of the present invention: 1 H-NMR(CDCl3)δ: 7.17(1H, s), 6.60(1H, d), 6.55(1H, t), 4.82(1H, s), 4.61(1H, s), 4.29(2H, s), 3.75(1H, s), 3.51(1H, s), 2.49(3H, s), 2.46(3H, s), 1.73 - 1.63(8H, m).

[0513] Compound 60 of the present invention: 1 H-NMR(CDCl3)δ: 7.17(1H, s), 6.56(1H, d), 6.53(1H, t), 4.43(1H, d), 4.29(2H, s), 4.02(1H, d), 3.41(1H, d), 2.49(3H, s), 2.46(3H, s), 2.31(3H, s), 2.25 - 2.21(1H, m), 1.76 - 1.26(8H, m), 1.02(3H, s), 1.00(3H, s).

[0514] Compound 61 of the present invention: 1 H-NMR(CDCl3)δ: 7.17(1H, s), 6.60(1H, d), 6.55(1H, dd), 4.61(1H, s), 4.39(1H, s), 4.29(2H, s), 3.83(1H, s), 3.58(1H, s), 2.49(3H, s), 2.46(3H, s), 2.33(3H, d), 1.79 - 1.53(8H, m).

[0515] Compound 62 of the present invention: 1 H-NMR(CDCl3)δ: 8.15(1H, d), 7.92(1H, d), 7.52(1H, t), 7.50(1H, d), 6.96(1H, d), 6.83(1H, s), 5.38(2H, s), 4.45(1H, d), 4.05(1H, d), 3.44(1H, d), 2.32(3H, s), 2.28 - 2.21(1H, m), 1.78 - 1.26(8H, m), 1.03(3H, s), 1.02(3H, s).

[0516] Compound 63 of the present invention: 1H-NMR(CDCl3) δ: 7.92(1H, d), 7.73(1H, d), 7.67(2H, m), 7.36(2H, m), 6.47(1H, m), 6.36(1H, s), 4.42(1H, d), 4.15(2H, s), 4.01(1H, d), 3.40(1H, d), 2.30(3H, s), 2.26 - 2.18(1H, m), 1.75 - 1.24(8H, m), 1.01(3H, s), 0.99(3H, s).

[0517] Compound 64 of the present invention: 1 H-NMR(CDCl3) δ: 8.45(1H, d), 6.80(1H, d), 5.06(1H, q), 3.88(1H, d), 3.63(1H, d), 3.23 - 3.09(1H, m), 1.86 - 1.53(6H, m), 1.51 - 1.41(5H, m), 1.16(3H, d), 1.08(3H, d).

[0518] Compound 65 of the present invention: 1 H-NMR(CDCl3) δ: 7.92(1H, d), 7.73(1H, d), 7.67(2H, d), 7.36(2H, d), 6.47(1H, t), 6.40(1H, s), 5.03(1H, q), 4.15(2H, s), 3.86(1H, d), 3.59(1H, d), 3.22 - 3.07(1H, m), 1.88 - 1.35(11H, m), 1.14(3H, d), 1.06(3H, d).

[0519] Compound 66 of the present invention: 1 H-NMR(CDCl3) δ: 8.55(1H, d), 8.34(1H, d), 7.97(1H, d), 7.77 - 7.67(2H, m), 6.47(1H, t), 6.44(1H, s), 5.03(1H, q), 4.15(2H, s), 3.86(1H, d), 3.59(1H, d), 3.22 - 3.07(1H, m), 1.86 - 1.28(11H, m), 1.14(3H, d), 1.06(3H, d).

[0520] Compound 67 of the present invention: 11H-NMR (CDCl3) δ: 8.16 (1H, d), 7.92 (1H, d), 7.55 - 7.49 (2H, m), 6.96 (1H, d), 6.86 (1H, s), 5.38 (2H, s), 5.06 (1H, q), 3.90 (1H, d), 3.63 (1H, d), 3.19 - 3.12 (1H, m), 1.76 - 1.56 (8H, m), 1.46 (3H, d), 1.16 (3H, d), 1.08 (3H, d).

[0521] Compound 68 of the present invention: 1 1H-NMR (CDCl3) δ: 7.58 - 7.54 (5H, m), 7.45 - 7.41 (2H, m), 7.35 - 7.33 (2H, m), 6.41 (1H, s), 5.03 (1H, q), 4.15 (2H, s), 3.88 (1H, d), 3.60 (1H, d), 3.18 - 3.09 (1H, m), 1.78 - 1.45 (8H, m), 1.44 (3H, d), 1.14 (3H, d), 1.06 (3H, d).

[0522] Compound 69 of the present invention: 1 1H-NMR (CDCl3) δ: 7.30 (2H, d), 7.19 (2H, d), 6.39 (1H, s), 5.03 (1H, q), 4.12 (2H, s), 3.87 (1H, d), 3.59 (1H, d), 3.17 - 3.10 (1H, m), 1.79 - 1.56 (8H, m), 1.44 (3H, d), 1.14 (3H, d), 1.06 (3H, d).

[0523] Compound 70 of the present invention: 1 1H-NMR (CDCl3) δ: 7.15 (4H, m), 6.34 (1H, s), 5.02 (1H, q), 4.06 (2H, s), 3.86 (1H, d), 3.58 (1H, d), 3.16 - 3.09 (1H, m), 2.34 (3H, s), 1.78 - 1.54 (8H, m), 1.43 (3H, d), 1.14 (3H, d), 1.06 (3H, d).

[0524] Compound 71 of the present invention: 1H-NMR(CDCl3) δ: 7.26(1H, s), 7.21(1H, s), 6.55(1H, s), 6.48(1H, s), 5.14(1H, t), 4.26(2H, s), 3.75(1H, d), 3.67(1H, d), 3.28 - 3.13(1H, m), 2.34(3H, s), 2.32(3H, s), 2.28 - 2.17(1H, m), 1.97 - 1.21(10H, m), 1.15 - 0.80(12H, m).

[0525] Compound 72 of the present invention: 1 H-NMR(CDCl3) δ: 7.18(2H, d), 6.97(2H, d), 6.78(1H, s), 5.18(2H, s), 5.05(1H, q), 3.87(1H, d), 3.61(1H, d), 3.18 - 3.11(1H, m), 1.83 - 1.56(8H, m), 1.46(3H, d), 1.15(3H, d), 1.08(3H, d).

[0526] Compound 73 of the present invention: 1 H-NMR(CDCl3) δ: 7.26(1H, s), 7.21(1H, s), 6.52(1H, s), 6.49(1H, s), 5.07(1H, d), 4.27(2H, s), 4.05(1H, d), 3.58(1H, dd), 3.48(1H, dd), 3.43(1H, d), 2.34(3H, s), 2.32(3H, s), 2.28 - 2.15(2H, m), 1.95 - 1.40(7H, m), 1.32 - 1.25(1H, m), 1.02(3H, d), 1.00(3H, d).

[0527] Compound 74 of the present invention: 1 H-NMR(CDCl3) δ: 7.32 - 7.28(2H, m), 7.23 - 7.18(3H, m), 6.42(1H, s), 5.04(1H, q), 3.87(1H, d), 3.60(1H, d), 3.17 - 3.10(1H, m), 2.80(2H, t), 2.71(2H, t), 2.10 - 2.02(2H, m), 1.82 - 1.55(8H, m), 1.45(3H, d), 1.15(3H, d), 1.08(3H, d).

[0528] Compound 75 of the present invention: 11H-NMR (CDCl3) δ: 7.15 (1H, s), 7.11 - 7.06 (2H, m), 6.52 - 6.45 (2H, m), 6.25 - 6.18 (1H, m), 5.04 (1H, q), 3.86 (1H, d), 3.67 (2H, d), 3.60 (1H, d), 3.17 - 3.10 (1H, m), 2.25 (6H, d), 1.76 - 1.55 (8H, m), 1.45 (3H, d), 1.15 (3H, d), 1.07 (3H, d).

[0529] Compound 76 of the present invention: 1 1H-NMR (CDCl3) δ: 6.41 (1H, s), 5.05 (1H, q), 3.89 (1H, d), 3.61 (1H, d), 3.17 - 3.10 (1H, m), 2.67 (2H, d), 2.10 - 2.03 (1H, m), 1.78 - 1.56 (8H, m), 1.45 (3H, d), 1.15 (3H, d), 1.08 (3H, d), 0.99 (3H, s), 0.97 (3H, s).

[0530] Compound 77 of the present invention: 1 1H-NMR (CDCl3) δ: 7.37 - 7.26 (5H, m), 6.36 (1H, t), 5.02 (1H, q), 4.11 (2H, s), 3.87 (1H, d), 3.59 (1H, d), 3.16 - 3.10 (1H, m), 1.78 - 1.54 (8H, m), 1.42 (3H, d), 1.14 (3H, d), 1.06 (3H, d).

[0531] Compound 78 of the present invention: 1 1H-NMR (CDCl3) δ: 8.70 - 8.68 (1H, m), 7.98 - 7.96 (2H, m), 7.78 - 7.70 (2H, m), 7.38 (2H, d), 7.24 - 7.22 (1H, m), 6.40 (1H, s), 5.03 (1H, q), 4.17 (2H, s), 3.86 (1H, d), 3.59 (1H, d), 3.18 - 3.10 (1H, m), 1.81 - 1.45 (8H, m), 1.44 (3H, d), 1.14 (3H, d), 1.06 (3H, d).

[0532] Compound 79 of the present invention: 1H-NMR(CDCl3) δ: 7.55(1H, s), 7.51(1H, d), 7.30(1H, d,), 6.99(1H, s), 6.88 - 6.61(1H, t), 6.37(1H, s), 5.02(1H, q), 4.20(2H, s), 3.86(1H, d), 3.59(1H, d), 3.16 - 3.09(1H, m), 1.78 - 1.54(8H, m), 1.43(3H, d), 1.14(3H, d), 1.06(3H, d).

[0533] Compound 80 of the present invention: 1 H-NMR(CDCl3) δ: 7.26(1H, s), 7.21(1H, s), 6.60(1H, s), 6.47(1H, s), 5.24(1H, s), 4.27(2H, s), 4.22(2H, q), 3.96(1H, d), 3.87(1H, d), 3.37 - 3.20(1H, m), 2.34(3H, s), 2.31(3H, s), 1.92 - 1.48(8H, m), 1.28(3H, t), 1.15(3H, d), 1.09(3H, d).

[0534] Compound 81 of the present invention: 1 H-NMR(CDCl3) δ: 7.17(1H, s), 6.62(1H, s), 6.54(1H, s), 5.24(1H, s), 4.29(2H, s), 4.22(2H, q), 3.97(1H, d), 3.88(1H, d), 3.37 - 3.21(1H, m), 2.49(3H, s), 2.46(3H, s), 1.92 - 1.47(8H, m), 1.29(3H, t), 1.15(3H, d), 1.09(3H, d).

[0535] Compound 82 of the present invention: 1 H-NMR(CDCl3) δ: 7.48 - 7.46(2H, m), 7.38(1H, s), 7.26 - 7.23(1H, m), 6.96 - 6.93(2H, m), 6.81(1H, s), 6.73 - 6.69(1H, m), 5.24(2H, s), 5.05(1H, q), 3.88(1H, d), 3.62(1H, d), 3.18 - 3.11(1H, m), 1.83 - 1.58(8H, m), 1.46(3H, d), 1.15(3H, d), 1.08(3H, d).

[0536] Compound 83 of the present invention: 1H-NMR(CDCl3) δ: 6.88 - 6.87 (2H, m), 6.78 (1H, s), 6.72 - 6.68 (1H, m), 5.17 (2H, s), 5.05 (1H, q), 3.87 (1H, d), 3.61 (1H, d), 3.19 - 3.12 (1H, m), 3.12 (1H, s), 1.82 - 1.56 (8H, m), 1.46 (3H, d), 1.15 (3H, d), 1.08 (3H, d).

[0537] Compound 84 of the present invention: 1 H-NMR(CDCl3) δ: 7.39 - 7.17 (7H, m), 6.52 (1H, s), 6.50 (1H, s), 4.79 (1H, d), 4.28 (2H, s), 4.07 (1H, d), 4.00 (1H, d), 3.61 (1H, d), 3.50 (1H, d), 2.35 (3H, s), 2.32 (3H, s), 1.81 - 1.15 (9H, m), 0.90 (3H, d), 0.86 (3H, d).

[0538] Compound 85 of the present invention: 1 H-NMR(CDCl3) δ: 7.46 - 7.42 (2H, m), 7.19 - 7.13 (1H, m), 6.70 (1H, s), 5.05 (1H, q), 4.66 (2H, s), 4.56 (2H, s), 3.87 (1H, d), 3.61 (1H, d), 3.18 - 3.11 (1H, m), 1.77 - 1.56 (8H, m), 1.46 (3H, d), 1.16 (3H, d), 1.08 (3H, d).

[0539] Compound 86 of the present invention: 1 H-NMR(CDCl3) δ: 7.41 - 7.18 (7H, m), 6.54 (1H, s), 6.49 (1H, s), 4.64 (1H, q), 4.27 (2H, s), 4.02 (1H, d), 3.93 (1H, d), 3.69 (1H, d), 3.53 (1H, d), 2.34 (3H, s), 2.32 (3H, s), 1.82 - 1.36 (8H, m), 1.17 (3H, d).

[0540] Compound 87 of the present invention: 11H-NMR (CDCl3) δ: 7.37 - 7.18 (7H, m), 6.55 (1H, s), 6.47 (1H, s), 4.49 (1H, s), 4.27 (2H, s), 4.22 (1H, s), 3.88 (1H, s), 3.65 (2H, s), 3.63 (1H, s), 2.34 (3H, s), 2.31 (3H, s), 1.93 - 1.54 (8H, m).

[0541] Compound 88 of the present invention: 1 1H-NMR (CDCl3) δ: 7.37 - 7.16 (7H, m), 6.58 (1H, s), 6.47 (1H, s), 4.80 (1H, s), 4.27 (1H, d), 4.27 (2H, s), 3.97 (2H, m), 3.91 - 3.80 (1H, m), 3.73 (1H, d), 3.64 - 3.47 (1H, d), 2.34 (3H, s), 2.31 (3H, s), 1.88 - 1.50 (8H, m), 0.97 (3H, t).

[0542] Compound 89 of the present invention: 1 1H-NMR (CDCl3) δ: 7.37 (1H, d), 7.25 (1H, s), 7.19 (1H, s), 6.53 (1H, s), 6.46 (1H, s), 6.32 (1H, dd), 6.08 - 5.96 (1H, m), 5.52 (1H, s), 4.25 (2H, s), 4.14 (1H, d), 3.86 (1H, d), 2.76 - 58 (1H, m), 2.57 - 2.43 (1H, m), 2.34 (3H, s), 2.31 (3H, s), 1.85 - 1.36 (8H, m), 0.86 (3H, t).

[0543] Compound 90 of the present invention: 1 1H-NMR (CDCl3) δ: 7.51 (2H, d), 7.24 (1H, s), 7.18 (1H, s), 6.84 (2H, d), 6.49 (1H, s), 6.44 (1H, s), 5.24 (1H, s), 4.23 (2H, s), 4.17 (1H, d), 3.79 (1H, d), 3.78 (3H, s), 2.78 - 2.61 (1H, m), 2.53 - 2.36 (1H, m), 2.33 (3H, s), 2.31 (3H, s), 1.90 - 1.57 (8H, m), 0.69 (3H, t).

[0544] Compound 91 of the present invention: 11H-NMR (CDCl3) δ: 7.58 (2H, d), 7.33 - 6.98 (5H, m), 6.49 (1H, s), 6.44 (1H, s), 5.29 (1H, s), 4.23 (2H, s), 4.19 (1H, d), 3.81 (1H, d), 2.80 - 2.62 (1H, m), 2.56 - 2.38 (1H, m), 2.33 (3H, s), 2.30 (3H, s), 1.89 - 1.22 (8H, m), 0.67 (3H, t).

[0545] Compound 92 of the present invention: 1 1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.32 (1H, t), 7.25 (1H, s), 7.20 (1H, s), 6.54 (1H, d), 6.52 (1H, s), 6.46 (1H, s), 5.45 (1H, s), 4.25 (2H, s), 4.12 (1H, d), 3.67 (1H, d), 2.80 - 2.63 (1H, m), 2.57 - 2.39 (1H, m), 2.34 (3H, s), 2.31 (3H, s), 1.87 - 1.47 (8H, m), 0.92 (3H, t).

[0546] Compound 93 of the present invention: 1 1H-NMR (CDCl3) δ: 8.33 (1H, d), 7.83 (1H, d), 7.69 (1H, dd), 6.43 (1H, s), 5.99 (1H, s), 5.03 (1H, q), 4.13 (2H, s), 3.86 (1H, d), 3.59 (1H, d), 3.19 - 3.08 (1H, m), 2.62 (3H, s), 2.29 (3H, s), 1.89 - 1.50 (8H, m), 1.44 (3H, s), 1.14 (3H, d), 1.07 (3H, d).

[0547] Compound 94 of the present invention: 1 1H-NMR (CDCl3) δ: 7.71 (2H, d), 7.56 (2H, d), 7.24 (1H, s), 7.18 (1H, s), 6.48 (1H, s), 6.44 (1H, s), 5.34 (1H, s), 4.24 (2H, s), 4.22 (1H, d), 3.80 (1H, d), 2.82 - 2.69 (1H, m), 2.55 - 2.41 (1H, m), 2.33 (3H, s), 2.31 (3H, s), 1.90 - 1.57 (7H, m), 1.44 - 1.36 (1H, m), 0.67 (3H, t).

[0548] Compound 95 of the present invention: 1 H-NMR(CDCl3)δ: 7.31(1H,dd), 7.24(1H,s), 7.21(1H,dd), 7.19(1H,s), 6.92(1H,dd), 6.52(1H,s), 6.45(1H,s), 5.75(1H,s), 4.24(2H,s), 4.22(1H,d), 3.70(1H,d), 2.86 - 2.68(1H,m), 2.65 - 2.46(1H,m), 2.34(3H,s), 2.31(3H,s), 1.91 - 1.50(7H,m), 1.38 - 1.24(1H,m), 0.92(3H,t).

[0549] Compound 96 of the present invention: 1 H-NMR(CDCl3)δ: 7.35(1H,dd), 7.25(1H,s), 7.20(1H,s), 6.55(1H,s), 6.46(1H,s), 6.37(1H,t), 6.30(1H,t), 6.00(1H,s), 4.25(2H,s), 4.10(1H,d), 3.76(1H,d), 3.28 - 3.17(1H,m), 2.34(3H,s), 2.31(3H,s), 1.81 - 1.44(8H,m), 1.12(3H,d), 0.88(3H,d).

[0550] Compound 97 of the present invention: 1 H-NMR(CDCl3)δ: 8.29(1H,d), 7.80(1H,dd), 7.62(1H,dd), 7.58(2H,d), 7.33 - 7.03(3H,m), 6.37(1H,s), 5.98(1H,s), 5.29(1H,s), 4.19(1H,d), 4.09(2H,s), 3.81(1H,d), 2.83 - 2.66(1H,m), 2.60(3H,s), 2.56 - 2.35(1H,m), 2.28(3H,s), 1.90 - 1.49(7H,m), 1.42 - 1.34(1H,m), 0.67(3H,t).

[0551] Compound 98 of the present invention: 11H-NMR (CDCl3) δ: 7.26 (1H, s), 7.22 (1H, s), 6.48 (2H, s), 4.78 (1H, s), 4.27 (2H, s), 4.05 (1H, d), 3.42 (1H, d), 3.01 - 2.90 (1H, m), 2.78 - 2.66 (1H, m), 2.34 (3H, s), 2.32 (3H, s), 1.92 - 1.21 (8H, m), 1.09 (3H, t), 0.98 (9H, s).

[0552] Compound 99 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.22 (1H, s), 6.49 (1H, s), 6.48 (1H, s), 4.56 (1H, s), 4.27 (2H, s), 4.03 (1H, d), 3.39 (1H, d), 2.38 (3H, s), 2.35 (3H, s), 2.32 (3H, s), 1.80 - 1.35 (8H, m), 0.98 (9H, s).

[0553] Compound 100 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.22 (1H, s), 6.49 (1H, s), 6.47 (1H, s), 4.59 (1H, s), 4.27 (2H, s), 3.93 (1H, d), 3.42 (1H, d), 2.35 (3H, s), 2.34 (3H, s), 2.32 (3H, s), 1.13 (3H, s), 0.97 (9H, s), 0.89 (3H, s).

[0554] Compound 101 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.58 (1H, s), 6.48 (1H, s), 4.60 (1H, s), 4.34 - 4.08 (5H, m), 3.77 (1H, d), 2.39 (3H, s), 2.34 (3H, s), 2.31 (3H, s), 1.85 - 1.57 (7H, m), 1.39 - 1.30 (1H, m), 1.28 (3H, t).

[0555] Compound 102 of the present invention: 11H-NMR (CDCl3) δ: 7.49 (1H, s), 7.29 (1H, s), 6.60 (1H, s), 6.50 (1H, s), 4.61 (1H, s), 4.34 - 4.06 (5H, m), 3.78 (1H, d), 2.45 (3H, s), 2.40 (3H, s), 1.86 - 1.54 (7H, m), 1.40 - 1.32 (1H, m), 1.29 (3H, t).

[0556] Compound 103 of the present invention: 1 1H-NMR (CDCl3) δ: 7.49 (1H, s), 7.30 (1H, s), 6.51 (2H, s), 4.57 (1H, s), 4.28 (2H, s), 4.05 (1H, d), 3.40 (1H, d), 2.46 (3H, s), 2.39 (3H, s), 1.88 - 1.35 (8H, m), 0.98 (9H, s).

[0557] Compound 104 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.51 (1H, s), 6.49 (1H, s), 5.18 (1H, s), 4.27 (2H, s), 4.11 (1H, d), 3.64 (1H, dd), 3.47 (1H, dd), 3.40 (1H, d), 2.34 (3H, s), 2.32 (3H, s), 2.28 (1H, t), 1.94 - 1.34 (8H, m), 0.99 (9H, s).

[0558] Compound 105 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.60 (1H, s), 6.48 (1H, s), 5.22 (1H, s), 4.43 - 4.05 (5H, m), 3.98 - 3.50 (3H, m), 2.34 (3H, s), 2.32 (3H, s), 2.26 (1H, t), 2.20 - 1.91 (1H, m), 1.85 - 1.49 (7H, m), 1.30 (3H, t).

[0559] Compound 106 of the present invention: 11H-NMR (CDCl3) δ: 8.34 (1H, d), 7.84 (1H, d), 7.69 (1H, dd), 6.36 (1H, s), 5.99 (1H, s), 4.56 (1H, s), 4.14 (2H, s), 4.02 (1H, d), 3.39 (1H, d), 2.62 (3H, s), 2.39 (3H, s), 2.29 (3H, s), 1.80 - 1.35 (8H, m), 0.98 (9H, s).

[0560] Compound 107 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.22 (1H, s), 6.51 (1H, s), 6.49 (1H, s), 4.42 (1H, d), 4.27 (2H, s), 4.01 (1H, d), 3.40 (1H, d), 2.35 (3H, s), 2.32 (3H, s), 2.31 (3H, s), 2.28 - 2.13 (1H, m), 1.80 - 1.42 (8H, m), 1.00 (6H, d).

[0561] Compound 108 of the present invention: 1 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.21 (1H, s), 6.58 (1H, s), 6.48 (1H, s), 4.60 (1H, s), 4.39 (1H, s), 4.27 (2H, s), 3.82 (1H, s), 3.58 (1H, s), 2.34 (6H, s), 2.32 (3H, s), 1.85 - 1.48 (8H, m).

[0562] Next, examples of the compounds of the present invention produced according to any one of the production examples described in the Examples and the production methods described in this specification are shown below.

[0563]

[0564] In the compound represented by formula (L-1) (hereinafter referred to as compound (L-1)), Y is an oxygen atom, p is 1, Q is a phenyl group, and the combinations of R 1 , R 4 , R 5 , R 8 and R 9 are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX1).

[0565] [Table L1]

[0566]

[0567] [Table L2]

[0568]

[0569] [Table L3]

[0570]

[0571] [Table L4]

[0572]

[0573] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX2).

[0574] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX3).

[0575] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX4).

[0576] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-chlorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX5).

[0577] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-chlorophenyl, R 1 , R 4 , R 5 , R 8 and R 9The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group SX6).

[0578] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-chlorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group SX7).

[0579] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-bromophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group SX8).

[0580] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-bromophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group SX9).

[0581] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-bromophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group SX10).

[0582] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-iodophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination recorded in [Table L1] to [Table L4] (hereinafter referred to as compound group S11).

[0583] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-iodophenyl, R 1 , R 4 , R 5 , R 8and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX12).

[0584] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-iodophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX13).

[0585] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX14).

[0586] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX15).

[0587] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX16).

[0588] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-methoxyphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX17).

[0589] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-methoxyphenyl, R 1 、R 4 、R5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX18).

[0590] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-methoxyphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX19).

[0591] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-trifluoromethylphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX20).

[0592] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-trifluoromethylphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX21).

[0593] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-trifluoromethylphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX22).

[0594] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-trifluoromethoxyphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group S23).

[0595] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-trifluoromethoxyphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX24).

[0596] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-trifluoromethoxyphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX25).

[0597] In compound (L-1), Y is an oxygen atom, p is 1, Q is benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX26).

[0598] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-fluorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX27).

[0599] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX28).

[0600] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-fluorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX29).

[0601] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-chlorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX30).

[0602] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-chlorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX31).

[0603] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-chlorobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX32).

[0604] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-bromobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX33).

[0605] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-bromobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX34).

[0606] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-bromobenzyl, R 1 , R 4 , R 5 , R 8 and R 9The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX35).

[0607] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-iodobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group S36).

[0608] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-iodobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX37).

[0609] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-iodobenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX38).

[0610] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-methylbenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX39).

[0611] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-methylbenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX40).

[0612] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-methylbenzyl, R 1 , R 4 , R 5 , R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX41).

[0613] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-methoxybenzyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX42).

[0614] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-methoxybenzyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX43).

[0615] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-methoxybenzyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX44).

[0616] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-trifluoromethylbenzyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX45).

[0617] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-trifluoromethylbenzyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX46).

[0618] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-trifluoromethylbenzyl, R 1, R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX47).

[0619] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-trifluoromethoxybenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group S48).

[0620] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-trifluoromethoxybenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX49).

[0621] In compound (L-1), Y is an oxygen atom, p is 1, Q is 4-trifluoromethoxybenzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX50).

[0622] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX51).

[0623] In compound (L-1), Y is an oxygen atom, p is 1, Q is 2-naphthylmethyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX52).

[0624] In compound (L-1), Y is an oxygen atom, p is 1, Q is 5-chloro-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX53).

[0625] In compound (L-1), Y is an oxygen atom, p is 1, Q is 6-chloro-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX54).

[0626] In compound (L-1), Y is an oxygen atom, p is 1, Q is 5,6-dichloro-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX55).

[0627] In compound (L-1), Y is an oxygen atom, p is 1, Q is 5-methyl-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX56).

[0628] In compound (L-1), Y is an oxygen atom, p is 1, Q is 6-methyl-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX57).

[0629] In compound (L-1), Y is an oxygen atom, p is 1, Q is 5,6-dimethyl-1-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX58).

[0630] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-phenyl-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX59).

[0631] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-fluorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX60).

[0632] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-fluorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX61).

[0633] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(4-fluorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX62).

[0634] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-chlorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX63).

[0635] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-chlorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX64).

[0636] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(4-chlorophenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX65).

[0637] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-methylphenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX66).

[0638] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-methylphenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX67).

[0639] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(4-methylphenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX68).

[0640] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-methoxyphenyl)-4-fluorophenyl, R 1 , R 4 , R 5 , R 8and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX69).

[0641] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-methoxyphenyl)-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX70).

[0642] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(4-methoxyphenyl)-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX71).

[0643] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-trifluoromethylphenyl)-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX72).

[0644] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-trifluoromethylphenyl)-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX73).

[0645] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(4-trifluoromethylphenyl)-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX74).

[0646] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(2-trifluoromethoxyphenyl)-4-fluorophenyl, R 1 and R 4 and R 5 and R 8 and R 9 and the combination of R

[0647] is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX75). 1 and R 4 and R 5 and R 8 and R 9 is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX76).

[0648] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-(3-trifluoromethoxyphenyl)-4-fluorophenyl, R 1 and R 4 and R 5 and R 8 and R 9 is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX77).

[0649] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-phenylphenyl, R 1 and R 4 and R 5 and R 8 and R 9 is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX78).

[0650] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-fluorophenyl)phenyl, R 1 and R 4 and R 5 and R 8 and R 9 is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX79).

[0651] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-fluorophenyl)phenyl, R 1 and R 4 and R 5 and R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX80).

[0652] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-fluorophenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX81).

[0653] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-chlorophenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX82).

[0654] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-chlorophenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX83).

[0655] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-chlorophenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX84).

[0656] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-methylphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX85).

[0657] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-methylphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX86).

[0658] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-methylphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX87).

[0659] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-methoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX88).

[0660] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-methoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX89).

[0661] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-methoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX90).

[0662] In the compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-trifluoromethylphenyl)phenyl, R 1 、R 4 、R 5 、R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX91).

[0663] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-trifluoromethylphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX92).

[0664] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-trifluoromethylphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX93).

[0665] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(2-trifluoromethoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX94).

[0666] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(3-trifluoromethoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX95).

[0667] In compound (L-1), Y is an oxygen atom, p is 1, Q is 3-fluoro-5-(4-trifluoromethoxyphenyl)phenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX96).

[0668] In compound (L-1), Y is a single bond, p is 0, Q is benzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX97).

[0669] In compound (L-1), Y is a single bond, p is 0, Q is 2-fluorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX98).

[0670] In compound (L-1), Y is a single bond, p is 0, Q is 3-fluorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX99).

[0671] In compound (L-1), Y is a single bond, p is 0, Q is 4-fluorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX100).

[0672] In compound (L-1), Y is a single bond, p is 0, Q is 2-chlorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX101).

[0673] In compound (L-1), Y is a single bond, p is 0, Q is 3-chlorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 form any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX102).

[0674] In compound (L-1), Y is a single bond, p is 0, Q is 4-chlorobenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX103).

[0675] In compound (L-1), Y is a single bond, p is 0, Q is 2-methylbenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group 104).

[0676] In compound (L-1), Y is a single bond, p is 0, Q is 3-methylbenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX105).

[0677] In compound (L-1), Y is a single bond, p is 0, Q is 4-methylbenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX106).

[0678] In compound (L-1), Y is a single bond, p is 0, Q is 2-methoxybenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX107).

[0679] In compound (L-1), Y is a single bond, p is 0, Q is 3-methoxybenzyl, and R 1 , R 4 , R 5 , R 8 and R 9The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX108).

[0680] In compound (L-1), Y is a single bond, p is 0, Q is 4-methoxybenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX109).

[0681] In compound (L-1), Y is a single bond, p is 0, Q is 4-phenylbenzyl, and R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX110).

[0682] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-fluorophenyl)benzyl, and R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX111).

[0683] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-fluorophenyl)benzyl, and R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX112).

[0684] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-fluorophenyl)benzyl, and R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX113).

[0685] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-chlorophenyl)benzyl, and R 1 , R 4, R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX114).

[0686] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-chlorophenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX115).

[0687] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-chlorophenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX116).

[0688] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-methylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX117).

[0689] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-methylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX118).

[0690] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-methylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 in the combination of are compounds of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX119).

[0691] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-methoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX120).

[0692] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-methoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX121).

[0693] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-methoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX122).

[0694] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-trifluoromethylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX123).

[0695] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-trifluoromethylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX124).

[0696] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-trifluoromethylphenyl)benzyl, R 1 , R 4 , R 5 , R 8 , and R 9The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX125).

[0697] In compound (L-1), Y is a single bond, p is 0, Q is 4-(2-trifluoromethoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX126).

[0698] In compound (L-1), Y is a single bond, p is 0, Q is 4-(3-trifluoromethoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX127).

[0699] In compound (L-1), Y is a single bond, p is 0, Q is 4-(4-trifluoromethoxyphenyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX128).

[0700] In compound (L-1), Y is a single bond, p is 0, Q is 4-(1-pyrrolyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX129).

[0701] In compound (L-1), Y is a single bond, p is 0, Q is 4-(1-pyrazolyl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX130).

[0702] In compound (L-1), Y is a single bond, p is 0, Q is 4-(1-imidazolyl)benzyl, R1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX131).

[0703] In compound (L-1), Y is a single bond, p is 0, Q is 4-(1,2,3-triazol-1-yl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX132).

[0704] In compound (L-1), Y is a single bond, p is 0, Q is 4-(1,2,3-triazol-2-yl)benzyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX133).

[0705] In compound (L-1), Y is a single bond, p is 0, Q is a hydrogen atom, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX134).

[0706] In compound (L-1), Y is a single bond, p is 0, Q is a methyl group, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX135).

[0707] In compound (L-1), Y is a single bond, p is 0, Q is an ethyl group, R 1 , R 4 , R 5 , R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX136).

[0708] In compound (L-1), Y is a single bond, p is 0, Q is propyl, R 1 , R 4 , R 5 , R 8 and R 9 and the combination of R

[0709] is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX137). 1 , R 4 , R 5 , R 8 and R 9 is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX138).

[0710] In compound (L-1), Y is a single bond, p is 0, Q is a C5H 11 group, R 1 , R 4 , R 5 , R 8 and R 9 is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX139).

[0711] In compound (L-1), Y is a single bond, p is 0, Q is a C6H 13 group, R 1 , R 4 , R 5 , R 8 and R 9 is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX140).

[0712] In compound (L-1), Y is a single bond, p is 0, Q is a C7H 15 group, R 1 , R 4 , R 5 , R 8 and R 9 is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX141).

[0713] In compound (L-1), Y is a single bond, p is 0, Q is a C8H 17 group, R 1 , R 4 , R 5 , R 8 and R9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX142).

[0714] In compound (L-1), Y is a single bond, p is 0, Q is CH2-benzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX143).

[0715] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-methylbenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX144).

[0716] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-methylbenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX145).

[0717] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-methylbenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX146).

[0718] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-methylbenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX147).

[0719] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-methylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX148).

[0720] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-fluorobenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX149).

[0721] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-fluorobenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX150).

[0722] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-fluorobenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX151).

[0723] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-fluorobenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX152).

[0724] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-fluorobenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX153).

[0725] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-chlorobenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX154).

[0726] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-chlorobenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX155).

[0727] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-chlorobenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX156).

[0728] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-chlorobenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX157).

[0729] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-chlorobenzofuran-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 The combination of is any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX158).

[0730] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-methoxybenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX159).

[0731] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-methoxybenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX160).

[0732] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-methoxybenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX161).

[0733] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-methoxybenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX162).

[0734] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-methoxybenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX163).

[0735] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4,5-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX164).

[0736] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4,6-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX165).

[0737] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4,7-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX166).

[0738] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5,6-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX167).

[0739] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5,7-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX168).

[0740] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6,7-dimethylbenzofuran-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX169).

[0741] In compound (L-1), Y is a single bond, p is 0, Q is CH2-benzothiophen-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX170).

[0742] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-methylbenzothiophen-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX171).

[0743] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-methylbenzothiophen-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX172).

[0744] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-methylbenzothiophen-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX173).

[0745] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-methylbenzothiophen-2-yl, R 1 , R 4 , R 5 , R 8 and R 9 are any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX174).

[0746] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-methylbenzothiophen-2-yl, R 1 , R 4 , R 5 , R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX175).

[0747] In compound (L-1), Y is a single bond, p is 0, Q is CH2-3-fluorobenzo[b]thiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX176).

[0748] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-fluorobenzo[b]thiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX177).

[0749] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-fluorobenzo[b]thiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX178).

[0750] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-fluorobenzo[b]thiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX179).

[0751] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-fluorobenzo[b]thiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX180).

[0752] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-3-chlorobenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX181).

[0753] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-4-chlorobenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX182).

[0754] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-5-chlorobenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX183).

[0755] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-6-chlorobenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX184).

[0756] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-7-chlorobenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX185).

[0757] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-3-methoxybenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX186).

[0758] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4-methoxybenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX187).

[0759] In compound (L-1), Y is a single bond, p is 0, Q is CH2-5-methoxybenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX188).

[0760] In compound (L-1), Y is a single bond, p is 0, Q is CH2-6-methoxybenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX189).

[0761] In compound (L-1), Y is a single bond, p is 0, Q is CH2-7-methoxybenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX190).

[0762] In compound (L-1), Y is a single bond, p is 0, Q is CH2-4,5-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX191).

[0763] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-4,6-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX192).

[0764] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-4,7-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX193).

[0765] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-5,6-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX194).

[0766] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-5,7-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX195).

[0767] In the compound (L-1), Y is a single bond, p is 0, Q is CH2-6,7-dimethylbenzothiophen-2-yl, R 1 、R 4 、R 5 、R 8 and R 9 are any combination of compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX196).

[0768] In the compound (L-1), Y is a single bond, p is 0, Q is (CH2)3phenyl, R 1 、R 4 、R 5 、R8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX197).

[0769] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-2-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX198).

[0770] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-3-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX199).

[0771] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-4-fluorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX200).

[0772] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-2-chlorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX201).

[0773] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-3-chlorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of and R is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX202).

[0774] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-4-chlorophenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX203).

[0775] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-2-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX204).

[0776] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-3-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX205).

[0777] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-4-methylphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX206).

[0778] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-2-methoxyphenyl, R 1 、R 4 、R 5 、R 8 and R 9 The combination of is any combination of the compounds described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX207).

[0779] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-3-methoxyphenyl, R 1 、R 4 、R 5 、R 8 and R 9The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX208).

[0780] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-4-methoxyphenyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX209).

[0781] In compound (L-1), Y is a single bond, p is 0, Q is (CH2)3-2-naphthyl, R 1 , R 4 , R 5 , R 8 and R 9 The combination is a compound of any combination described in [Table L1] to [Table L4] (hereinafter referred to as compound group SX210).

[0782] Next, formulation examples of the compounds of the present invention are shown. It should be noted that "parts" means parts by weight. In addition, compound S of the present invention means a compound described in compound groups SX1 to SX210 or any one of compounds 1 to 108 of the present invention.

[0783] Formulation Example 1

[0784] 35 parts of a mixture of ammonium polyoxyethylene alkyl ether sulfate and silica (weight ratio 1:1), 10 parts of any one of compound S of the present invention, and 55 parts of water are mixed and micronized by a wet grinding method to obtain a formulation.

[0785] Formulation Example 2

[0786] 50 parts of any one of compound S of the present invention, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are pulverized and mixed to obtain a formulation.

[0787] Formulation Example 3

[0788] 5 parts of any one of compound S of the present invention, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (ethylene oxide addition number: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed to obtain a formulation.

[0789] Formulation Example 4

[0790] Two parts of any one of the compounds S of the present invention, one part of silica, two parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, an appropriate amount of water is added, kneaded, granulated using a granulator, and then dried to obtain a preparation.

[0791] Formulation Example 5

[0792] Ten parts of any one of the compounds S of the present invention are mixed into a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ, and 54 parts of solvent naphtha are added thereto, and mixed to obtain a preparation.

[0793] Formulation Example 6

[0794] Zero point one part of any one of the compounds S of the present invention and 39.9 parts of kerosene are mixed and dissolved, filled into an aerosol container, and 60 parts of liquefied petroleum gas (a mixture of propane, butane, and isobutane; saturated vapor pressure: 0.47 MPa (25 °C)) are filled therein to obtain a preparation.

[0795] Formulation Example 7

[0796] Zero point two part of any one of the compounds S of the present invention, 50 parts of pyrethrum extract meal powder, 30 parts of Machilus thunbergii powder, and 19.8 parts of wood powder are mixed, an appropriate amount of water is added, kneaded, and then fed to an extruder to form a plate-shaped sheet, and formed into a spiral shape using a punching machine to obtain a preparation.

[0797] Next, Test Examples are used to show the efficacy of the compounds of the present invention against harmful arthropods. In the following Test Examples, the tests were carried out at 25 °C.

[0798] Test Method 1

[0799] The test compound is formulated into a preparation according to the method described in Formulation Example 1, and water containing 0.03% by volume of Shindain (registered trademark) is added thereto to prepare a dilution containing a specified concentration of the test compound.

[0800] About 30 cotton aphids (all stages) are inoculated onto cucumber (Cucumis sativus) seedlings (at the stage when the second true leaf unfolds) planted in a container. One day later, the dilution is sprayed onto the seedlings at a ratio of 10 mL / seedling. Further, after 5 days, the number of surviving insects is investigated, and the control value is calculated from the following formula.

[0801] Control value (%) = {1 - (Cb × Tai) / (Cai × Tb)} × 100

[0802] It should be noted that the letters in the formula represent the following meanings.

[0803] Cb: Number of test insects in the untreated area

[0804] Cai: Number of surviving insects at the time of investigation in the untreated area

[0805] Tb: Number of test insects in the treated area

[0806] Tai: Number of surviving insects at the time of investigation in the treated area

[0807] Here, the untreated area refers to the area where the same operations as the treated area are carried out except for not using the test compound.

[0808] Test Example 1-1

[0809] The specified concentration was set at 500 ppm, and the following compounds of the present invention were used as test compounds. Tests were carried out according to Test Method 1. As a result, all of the following compounds of the present invention showed a control value of 90% or more.

[0810] Compounds of the present invention: 29, 91

[0811] Test Method 2

[0812] The test compound was formulated according to the method described in Formulation Example 1, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0813] The dilution was sprayed onto cabbage (Brassicae oleracea) seedlings (at the stage where the second to third true leaves were unfolded) planted in containers at a ratio of 20 mL / seedling. Then, the stem and leaf parts of the seedlings were cut and placed in a container lined with filter paper. Five second-instar larvae of Spodoptera litura were placed therein. After 5 days, the number of surviving insects was counted, and the mortality rate was calculated from the following formula.

[0814] Mortality rate (%) = (1 - number of surviving insects / 5) × 100

[0815] Test Example 2-1

[0816] The specified concentration was set at 500 ppm, and the following compounds of the present invention were used as test compounds. Tests were carried out according to Test Method 2. As a result, all of the following compounds of the present invention showed a mortality rate of 80% or more.

[0817] Compounds of the present invention: 14, 16, 18, 20, 21, 22, 24, 25, 26, 28, 29, 30, 31, 32, 34, 36, 37, 38, 39, 41, 43, 44, 45, 46, 47, 49, 50, 51, 52, 53, 54, 55, 58, 59, 60, 61, 62, 63, 67, 68, 69, 71, 73, 75, 78, 79, 82, 85, 86, 89, 91, 92, 93, 95, 99, 100, 103, 104

[0818] Test method 3

[0819] Prepare a preparation of the test compound according to the method described in Preparation Example 1, add water containing 0.03% by volume of Shindain (registered trademark) thereto, and prepare a dilution containing a specified concentration of the test compound.

[0820] Spray the dilution on the cabbage (Brassicae oleracea) seedlings (at the stage when the second to third true leaves are unfolded) planted in a container at a ratio of 20 mL / seedling. Then, cut the stem and leaf parts of the seedlings, put them into a container lined with filter paper. Put 5 second-instar larvae of Plutella xylostella into it. After 5 days, count the number of surviving insects, and calculate the mortality rate of dead insects from the following formula.

[0821] Mortality rate (%) = (1 - number of surviving insects / 5) × 100

[0822] Test Example 3-1

[0823] Set the specified concentration to 500 ppm, use the following compounds of the present invention as test compounds, and conduct tests according to Test Method 3. As a result, the following compounds of the present invention all showed a mortality rate of more than 80%.

[0824] Compounds of the present invention: 6, 14, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 32, 34, 35, 36, 37, 38, 39, 41, 46, 47, 48, 49, 50, 51, 52, 55, 57, 58, 59, 60, 61, 62, 63, 65, 66, 67, 68, 69, 73, 74, 75, 77, 78, 79, 80, 82, 83, 84, 85, 86, 89, 90, 91, 92, 93, 95, 96, 97, 99, 100, 101, 102, 103, 104, 105, 106

[0825] Test method 4

[0826] Dissolve 1 mg of the test compound in 50 μL of a mixed solution of polyoxyethylene sorbitan monolaurate:acetone = 5:95 (by volume). Add water containing 0.03% by volume of Shindain (registered trademark) thereto to prepare a dilution containing the test compound at a specified concentration.

[0827] Immerse the seedlings of Zea mays in the dilution for 30 seconds. Then, place 2 of the seedlings in a petri dish (90 mm in diameter) and put 10 second-instar larvae of the western corn rootworm therein. After 5 days, count the number of dead insects and calculate the mortality rate from the following formula.

[0828] Mortality rate (%) = (number of dead insects / 10) × 100

[0829] Test Example 4-1

[0830] Set the specified concentration to 200 ppm, use the compound of the present invention as the test compound, and conduct the test according to Test Method 4. Thus, the control effect can be confirmed.

[0831] Compound of the present invention:

[0832] Test Method 5

[0833] Inject an acetone solution prepared such that the test compound is 800 ppm into a container with an internal volume of 50 mL, and uniformly coat the inner surface of the container such that the test compound is 40 mg / m 2 and then dry it.

[0834] Put 5 male adults of Blattella germanica into the container, close the lid. After a specified time, investigate the state of Blattella germanica and calculate the mortality rate. The mortality rate is calculated from the following formula.

[0835] Mortality rate (%) = (number of dead insects / number of test insects) × 100

[0836] Test Example 5-1

[0837] Set the specified time to 1 hour, use the following compound of the present invention as the test compound, and conduct the test according to Test Method 5. As a result, all of the following compounds of the present invention showed a mortality rate of 80% or more.

[0838] Compounds of the present invention: 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 49, 50, 51, 56, 58, 65, 93

[0839] Test Example 5-2

[0840] The specified time was set to 1 day, and the following compounds of the present invention were used as test compounds. The test was conducted according to Test Method 5. As a result, all of the following compounds of the present invention showed a dead insect rate of 80% or more.

[0841] Compounds of the present invention: 4, 5, 6, 7, 8, 9, 11, 12, 15, 16, 18, 19, 20, 21, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 52, 56, 57, 58, 60, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 83, 85, 86, 89, 92, 93, 95, 96, 99, 104, 105, 106, 107, 108

[0842] Test Example 5-3

[0843] The specified time was set to 3 days, and the following compounds of the present invention were used as test compounds. The test was conducted according to Test Method 5. As a result, all of the following compounds of the present invention showed a dead insect rate of 80% or more.

[0844] Compounds of the present invention: 3, 4, 5, 6, 7, 8, 9, 11, 12, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 59, 60, 61, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 83, 85, 86, 89, 91, 92, 93, 95, 96, 97, 98, 99, 100, 104, 105, 106, 107, 108

[0845] Test Method 6

[0846] An acetone solution prepared such that the test compound was 2000 ppm was injected into a container with an internal volume of 20 mL, and uniformly coated on the inner surface of the container such that the test compound was 100 mg / m 2 and then dried.

[0847] Five larvae of Haemaphysalis longicornis were placed in the container and the lid was closed. After a specified time, the state of Haemaphysalis longicornis was investigated and the dead insect rate was determined. The dead insect rate was calculated by the following formula.

[0848] Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0849] Test Example 6-1

[0850] With the specified time set to 2 days, using the following compounds of the present invention as test compounds, and conducting tests according to Test Method 6, as a result, all of the following compounds of the present invention showed a mortality rate of 80% or more.

[0851] Compounds of the present invention: 1, 2, 3, 5, 6, 16, 18, 20, 21, 23, 25, 26, 27, 28, 29, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 42, 45, 46, 47, 49, 50, 51, 56, 57, 58, 59, 60, 61, 62

[0852] Test Method 7

[0853] Inject an acetone solution prepared such that the test compound is 800 ppm into a container with an internal volume of 20 mL, and uniformly coat the inner surface of the container such that the test compound is 40 mg / m 2 and then allow it to dry.

[0854] Place 5 female adult houseflies into this container, close the lid. After the specified time, investigate the state of the houseflies and calculate the mortality rate. The mortality rate is calculated by the following formula.

[0855] Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0856] Test Example 7-1

[0857] With the specified time set to 1 hour, using the following compounds of the present invention as test compounds, and conducting tests according to Test Method 7, as a result, all of the following compounds of the present invention showed a mortality rate of 80% or more.

[0858] Compounds of the present invention: 3, 4, 5, 6, 7, 8, 9, 10, 12, 15, 18, 19, 20, 23, 24, 25, 26, 28, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 56, 57, 58, 60, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 85, 89, 92, 93, 98, 99, 100, 105, 107

[0859] Test Example 7-2

[0860] Set the specified time to 1 day, use the following compounds of the present invention as test compounds, and conduct tests according to Test Method 7. As a result, all the following compounds of the present invention showed a dead bug rate of 80% or more.

[0861] Compounds of the present invention: 3, 4, 5, 6, 7, 8, 10, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 83, 85, 86, 89, 92, 93, 96, 98, 99, 100, 103, 104, 105, 106, 107, 108

[0862] Test Method 8

[0863] Inject an acetone solution prepared such that the test compound is 200 ppm into a container with an internal volume of 20 mL, and uniformly coat the inner surface of the container such that the test compound is 10 mg / m 2 and then dry it.

[0864] Place 5 female adult Culex pipiens pallens into this container and close the lid. After the specified time, investigate the state of Culex pipiens pallens and calculate the dead bug rate. The dead bug rate is calculated by the following formula.

[0865] Dead bug rate (%) = (Number of dead bugs / Number of test bugs) × 100

[0866] Test Example 8-1

[0867] Set the specified time to 1 hour, use the following compounds of the present invention as test compounds, and conduct tests according to Test Method 8. As a result, all the following compounds of the present invention showed a dead bug rate of 80% or more.

[0868] Compounds of the present invention: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 19, 25, 26, 28, 30, 31, 34, 35, 36, 38, 39, 40, 41, 42, 44, 47, 48, 49, 50, 51, 56, 57, 58, 60, 63, 64, 65, 66, 67, 68, 69, 70, 71, 75, 76, 77, 78, 79, 82, 83, 86, 92, 93, 100, 106, 107

[0869] Test Example 8-2

[0870] The specified time was set to 1 day, and the compounds of the present invention described below were used as test compounds, and the test was carried out according to Test Method 8. As a result, all the compounds of the present invention described below showed a dead insect rate of 80% or more.

[0871] Compounds of the present invention: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 83, 84, 85, 86, 89, 91, 92, 93, 96, 97, 98, 99, 100, 103, 104, 105, 106, 107, 108

[0872] Test Method 9

[0873] An acetone solution prepared so that the test compound was 50 ppm was injected into a container with an internal volume of 20 mL, and uniformly coated on the inner surface of the container in such a way that the test compound was 2.5 mg / m 2 and then dried.

[0874] Ten female adult Monomorium pharaonis were placed into this container, and the lid was closed. After the specified time, the state of Monomorium pharaonis was investigated, and the dead insect rate was determined. The dead insect rate was calculated by the following formula.

[0875] Dead insect rate (%) = (number of dead insects / number of test insects) × 100

[0876] Test Example 9-1

[0877] The specified time was set to 1 hour, and the compounds of the present invention described below were used as test compounds, and the test was carried out according to Test Method 9. As a result, all the compounds of the present invention described below showed a dead insect rate of 70% or more.

[0878] Compounds of the present invention: 4, 5, 6, 8, 11, 12, 15, 18, 19, 20, 21, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 49, 51, 53, 58, 60, 63, 65, 66, 68, 69, 70, 71, 73, 75, 78, 79, 82, 85, 86, 89, 91, 92, 93, 95, 96, 97, 98, 99, 100, 103, 104, 105, 106, 107

[0879] Test Example 9-2

[0880] The specified time was set to 1 day, and the following compounds of the present invention were used as test compounds. Tests were conducted according to Test Method 9. As a result, the following compounds of the present invention all showed a dead insect rate of more than 70%.

[0881] Compounds of the present invention: 4, 5, 6, 7, 8, 9, 11, 12, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 78, 79, 82, 83, 85, 86, 89, 90, 91, 92, 93, 95, 96, 97, 98, 99, 100101, 103, 104, 105, 106, 107, 108

[0882] Test Method 10

[0883] The test compounds were formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0884] The dilution was sprayed onto cucumber (Cucumis sativus) seedlings (at the stage when the second leaf was unfolded) planted in containers at a rate of 10 mL / seedling. Then, the first true leaf was cut and placed in a container, and about 20 larvae of Frankliniella occidentalis were put into it. After 7 days, the number of surviving insects was investigated, and the dead insect rate was calculated by the following formula.

[0885] Dead insect rate (%) = {1 - number of surviving insects / 20} × 100

[0886] Test Example 10-1

[0887] The specified concentration was set at 200 ppm, and the following compounds of the present invention were used as test compounds. Tests were conducted according to Test Method 10. As a result, all of the following compounds of the present invention showed a dead insect rate of 90% or more.

[0888] Compounds of the present invention: 18, 20, 21, 22, 25, 29, 30, 31, 37, 38, 39, 43, 45, 47, 57, 58, 60, 62, 63, 65, 66, 67, 68, 69, 70, 72, 78, 79, 82, 89, 93, 97, 99, 106

[0889] Test Method 11

[0890] The test compounds were formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0891] The dilution was sprayed onto cabbage (Brassicae oleracea) seedlings (at the stage where the 3rd to 4th true leaves were unfolded) planted in containers at a rate of 20 mL / seedling. Then, 10 third-instar larvae of Spodoptera litura were placed therein. After 6 days, the number of surviving insects was counted, and the dead insect rate was calculated by the following formula.

[0892] Dead insect rate (%) = (1 - number of surviving insects / 10) × 100

[0893] Test Example 11-1

[0894] The specified concentration was set at 200 ppm, and the following compounds of the present invention were used as test compounds. Tests were conducted according to Test Method 11. As a result, all of the following compounds of the present invention showed a dead insect rate of 80% or more.

[0895] Compounds of the present invention: 14, 16, 18, 20, 21, 22, 25, 28, 29, 30, 31, 32, 34, 36, 37, 38, 39, 41, 43, 45, 46, 47, 49, 50, 51, 55, 58, 60, 61, 62, 67, 68, 69, 71, 73, 75, 79, 85, 89, 91, 92, 93, 95, 99, 100, 103

[0896] Test Method 12

[0897] The test compounds were formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0898] To the cabbage (Brassicae oleracea) seedlings (at the stage where the 3rd to 4th true leaves are unfolded) planted in containers, the dilution was sprayed at a rate of 20 mL / seedling. Then, 10 third-instar larvae of Plutella xylostella were introduced. After 5 days, the number of surviving insects was counted, and the mortality rate was calculated using the following formula.

[0899] Mortality rate (%) = (1 - number of surviving insects / 10) × 100

[0900] Test Example 12-1

[0901] With the specified concentration set at 200 ppm, the following compounds of the present invention were used as test compounds, and tests were conducted according to Test Method 12. As a result, all of the following compounds of the present invention showed a mortality rate of 80% or more.

[0902] Compounds of the present invention: 14, 16, 17, 18, 20, 21, 22, 23, 28, 29, 32, 34, 35, 36, 37, 38, 39, 41, 46, 47, 49, 50, 51, 55, 60, 61, 62, 63, 65, 67, 68, 69, 73, 74, 75, 78, 79, 82, 83, 84, 90, 95, 96, 97, 99, 100, 103, 105, 106

[0903] Test Method 13

[0904] The test compounds were formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0905] Approximately 30 cotton aphids (all stages) were inoculated onto cucumber (Cucumis sativus) seedlings (at the stage where the 2nd true leaf is unfolded) planted in containers. After 1 day, the dilution was sprayed onto the seedlings at a rate of 10 mL / seedling. Furthermore, after 5 days, the number of surviving insects was investigated, and the control value was calculated using the following formula.

[0906] Control value (%) = {1 - (Cb × Tai) / (Cai × Tb)} × 100

[0907] It should be noted that the letters in the formula have the following meanings.

[0908] Cb: Number of test insects in the untreated area

[0909] Cai: Number of surviving insects at the time of investigation in the untreated area

[0910] Tb: Number of test insects in the treated area

[0911] Tai: Number of surviving insects at the time of investigation in the treated area

[0912] Here, the untreated area refers to the area where the same operations as the treated area are carried out except for not using the test compound.

[0913] Test Example 13-1

[0914] The specified concentration was set to 200 ppm, and the compound of the present invention was used as the test compound. The test was carried out according to Test Method 13, whereby the control effect could be confirmed.

[0915] Compound of the present invention:

[0916] Test Method 14

[0917] The test compound was formulated into a preparation according to the method described in Formulation Example 1, and water was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0918] Thirty last-instar larvae of Culex pipiens pallens were placed in this dilution, and the state of the Culex pipiens pallens larvae was investigated after 1 day, and the mortality rate was calculated. The mortality rate was calculated by the following formula.

[0919] Mortality rate (%) = (Number of dead insects / Number of test insects) × 100

[0920] Test Example 14-1

[0921] The specified concentration was set to 3.5 ppm, and the following compounds of the present invention were used as the test compounds. The test was carried out according to Test Method 14. As a result, all of the following compounds of the present invention showed a mortality rate of 91% or more.

[0922] Compounds of the present invention: 11, 14, 16, 18, 20, 21, 22, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 46, 47, 48, 49, 50, 51, 53, 55, 58, 59, 60, 61, 62, 65, 66, 67, 68, 69, 70, 71, 72, 73, 75, 77, 78, 79, 81, 82, 83, 85, 89, 93, 97, 102, 104

[0923] Test Method 15

[0924] The test compound was formulated into a preparation according to the method described in Formulation Example 1, and water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a dilution containing the test compound at a specified concentration.

[0925] The diluted solution was sprayed at a rate of 10 mL per seedling onto rice (Oryza sativa) seedlings (at the stage when the second leaf was unfolded) planted in containers. Then, 20 third-instar larvae of the brown planthopper were introduced. After 6 days, the number of surviving insects was counted, and the mortality rate of dead insects was calculated using the following formula.

[0926] Mortality rate (%) = {1 - number of surviving insects / 20} × 100

[0927] Test Example 15-1

[0928] The specified concentration was set at 500 ppm, and the following compounds of the present invention were used as test compounds. Tests were conducted according to Test Method 15. As a result, all of the following compounds of the present invention showed a mortality rate of 90% or more.

[0929] Compounds of the present invention: 18, 20, 25, 26, 29, 34, 35, 36, 38, 42, 45, 46, 48, 50, 51, 52, 57, 58, 60, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 82, 83, 85, 106

[0930] Test Method 16

[0931] The test compounds were formulated according to the method described in Formulation Example 5. Water containing 0.03% by volume of Shindain (registered trademark) was added thereto to prepare a diluted solution containing the test compounds at a specified concentration.

[0932] The diluted solution was sprayed at a rate of 10 mL per seedling onto rice (Oryza sativa) seedlings (at the stage when the second leaf was unfolded) planted in containers. Then, 20 third-instar larvae of the brown planthopper were introduced. After 6 days, the number of surviving insects was counted, and the mortality rate of dead insects was calculated using the following formula.

[0933] Mortality rate (%) = {1 - number of surviving insects / 20} × 100

[0934] Test Example 16-1

[0935] The specified concentration was set at 200 ppm, and the following compounds of the present invention were used as test compounds. Tests were conducted according to Test Method 16. As a result, all of the following compounds of the present invention showed a mortality rate of 90% or more.

[0936] Compounds of the present invention: 18, 20, 29, 31, 34, 35, 38, 39, 43, 45, 46, 47, 49, 50, 51, 58, 60, 62, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 78, 79, 82, 83, 106

[0937] Test Method 17

[0938] Dissolve 1 mg of the compound of the present invention in 10 μL of a mixed solution of xylene:DMF:surfactant = 4:4:1 (volume ratio), and dilute with water containing 0.02% by volume of a spreading agent to prepare a dilution A containing a specified concentration of the compound of the present invention.

[0939] Dissolve 1 mg of this ingredient in 10 μL of a mixed solution of xylene:DMF:surfactant = 4:4:1 (volume ratio), and dilute with water containing 0.02% by volume of a spreading agent to prepare a dilution B containing a specified concentration of this ingredient.

[0940] Mix dilution A and dilution B to obtain dilution C.

[0941] Place the cucumber cotyledon leaves (1.5 cm in length) in each well of a 24-well microplate. Put 2 wingless adult aphids and 8 larvae in each well, and spread 20 μL of dilution C in each well. This is used as the treatment area.

[0942] It should be noted that the wells where 20 μL of water containing 0.02% by volume of a spreading agent is spread instead of dilution C are used as the untreated area.

[0943] After dilution C dries, cover the upper part of the microplate with a membrane. After 5 days, investigate the number of surviving insects in each well.

[0944] Calculate the control value from the following formula.

[0945] Control value (%) = {1 - (Tai) / (Cai)} × 100

[0946] It should be noted that the symbols in the formula represent the following meanings.

[0947] Cai: The number of surviving insects at the time of investigation in the untreated area

[0948] Tai: The number of surviving insects at the time of investigation in the treatment area

[0949] Regarding the specific dilution C for which the effect can be confirmed by Test Method 17, it is shown in the following 1) to 5).

[0950] 1) Among the combinations recorded in List A, dilution C in which the concentration of the compound of the present invention is 200 ppm and the concentration of this ingredient is 2000 ppm. It should be noted that in List A, Comp X refers to any one compound selected from the compound groups SX1 to SX210 and the compounds 1 to 108 of the present invention.

[0951] List A:

[0952] Comp X + clothianidin; Comp X + thiamethoxam; Comp X + imidacloprid; Comp X + thiacloprid; Comp X + flupyradifurone; Comp X + sulfoxaflor; Comp X + triflumezopyrim; Comp X + dichlorothiazopyrim; Comp X + beta-cyfluthrin; Comp X + tefluthrin; Comp X + fipronil; Comp X + chlorantraniliprole; Comp X + cyantraniliprole; Comp X + tetramicarbamide; Comp X + thiodicarb; Comp X + carbofuran; Comp X + fluxametamide; Comp X + afoxolaner; Comp X + fluralaner; Comp X + broflanilide; Comp X + abamectin; Comp X + fluxapyroxad; CompX + flumorph; Comp X + triflumizole; Comp X + thiophene; Comp X + fluoropyrimidine; Comp X + mycorrhizal fungi; Comp X + Bradyrhizobium japonicum TA-11 strain; Comp X + Bacillus firmus; Comp X + Bacillus firmus I-1582 strain; Comp X + Bacillus amyloliquefaciens; Comp X + Bacillus amyloliquefaciens FZB42 strain; Comp X + Pasteuria; Comp X + Pasteuria Pn1 strain; Comp X + Bacillus badius; Comp X + tebuconazole; Comp X + prothioconazole; Comp X + metconazole; Comp X + ipconazole; Comp X + triazolone; Comp X + difenoconazole; Comp X + imazalil; Comp X + triadimenol; Comp X + fluquinconazole; Comp X + difenoconazole; Comp X + mandestrobin; Comp X + azoxystrobin; Comp X + pyraclostrobin; Comp X + trifloxystrobin; Comp X + fluoxastrobin; Comp X + picoxystrobin; Comp X + fenamidone; Comp X + metalaxyl; Comp X + metalaxyl-M; Comp X + fludioxonil; Comp X + sedaxane; Comp X + fluxapyroxad; Comp X + bixafen; Comp X + benzovindiflupyr; Comp X + boscalid; Comp X + pyrisoxazole; Comp X + captan; Comp X + thiram; Comp X + tolclofos-methyl; Comp X + thiabendazole; Comp X + ethaboxam; Comp X + mancozeb; Comp X + tetraconazole; Comp X + oxathiapiprolin; Comp X + silthiofam; Comp X + inpyrfluxam.

[0953] 2) In the combinations described in List A, Diluent C in which the concentration of the compound of the present invention is 200 ppm and the concentration of this component is 200 ppm.

[0954] 3) In the combinations described in List A, Diluent C in which the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 50 ppm.

[0955] 4) In the combinations described in List A, Diluent C in which the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 5 ppm.

[0956] 5) In the combinations described in List A, Diluent C in which the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 0.5 ppm.

[0957] Industrial Applicability

[0958] The compound of the present invention exhibits excellent control effects against harmful arthropods.

Claims

1. A compound of formula (I) or a salt thereof, In formula (I), R 1 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, a C1-C3 alkylcarbonyl group which may have one or more halogen atoms, a C1-C3 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C3 alkylsulfonyl group which may have one or more halogen atoms, or a hydrogen atom. R 2 、R 3 、R 5 、R 6 and R 7 are the same as or different from each other, and represent a C1-C6 chain hydrocarbon group that may have one or more substituents selected from group A, a C3-C6 alicyclic hydrocarbon group that may have one or more substituents selected from group A, a C1-C3 alkoxy group that may have one or more halogen atoms, or a hydrogen atom. R 4 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a C1-C3 alkoxy group which may have one or more halogen atoms R 8 and R 9 which are the same as or different from each other, represent a C1-C20 chain hydrocarbon group which may have one or more substituents selected from group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from group A, a phenyl group, a pyridyl group, a furyl group, a tetrahydrofuryl group, a thienyl group, a tetrahydrothienyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group {the phenyl group, the pyridyl group, the furyl group, the tetrahydrofuryl group, the thienyl group, the tetrahydrothienyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group may have one or more substituents selected from group B}, or a hydrogen atom, m represents 0, 1, 2 or 3, When m is 2 or 3, the 2 or 3 Rs 2 and R 3 can each independently be the same or different, n represents 1, 2, 3 or 4, In the case where n is 2, 3 or 4, two, three or four Rs 6 and R 7 can each independently be the same or different, R 2 and R 3 can together form -(CR 13 R 14 )-(CR 15 R 16 ) a -(CR 17 R 18 )- or -(CR 19 R 20 ) b -Z 1 -(CR 21 R 22 ) c -, R 4 and R 5 can together form -(CR 23 R 24 )-(CR 25 R 26 ) d -(CR 27 R 28 )- or -(CR 29 R 30 ) e -Z 2 -(CR 31 R 32 ) f -, R 6 and R 7 can together form -(CR 33 R 34 )-(CR 35 R 36 ) g -(CR 37 R 38 )- or -(CR 39 R 40 ) h -Z 3 -(CR 41 R 42 ) i -, R 8 and R 9 can together form -(CR 43 R 44 )-(CR 45 R 46 ) j -(CR 47 R 48 )- or -(CR 49 R 50 ) k -Z 4 -(CR 51 R 52 ) r -, a, d, g and j each independently represent 0, 1, 2 or 3, b, c, e, f, h, i, k and r each independently represent 1 or 2, Z 1 , Z 2 , Z 3 and Z 4 The same or different from each other, representing an oxygen atom, a sulfur atom or NR 53 , R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 、R 22 、R 23 、R 24 、R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、R 34 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 、R 42 、R 43 、R 44 、R 45 、R 46 、R 47 、R 48 、R 49 、R 50 、R 51 、R 52 and R 53 are the same as or different from each other, and represent a C1-C4 alkyl group that may have one or more halogen atoms, or a hydrogen atom. In the case where a, d, g or j is 2 or 3, the two or three Rs 15 , R 16 , R 25 , R 26 , R 35 , R 36 , R 45 , and R 46 may each independently be the same or different, When b, c, e, f, h, i, k, or r is 2, the two Rs 19 , R 20 , R 21 , R 22 , R 29 , R 30 , R 31 , R 32 , R 39 , R 40 , R 41 , R 42 , R 49 , R 50 , R 51 and R 52 may each independently be the same or different, Multiple Rs 53 Each independently may be the same or different, R 10 represents a C1-C3 chain hydrocarbon group which may have one or more substituents selected from group D, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a cyano group, a formyl group, a carboxyl group, a carbamoyl group, a halogen atom or a hydrogen atom, Y represents a single bond, an oxygen atom or -S(O)- u -, When Y is a single bond, p represents 0, Q represents a C1-C8 chain hydrocarbon group which may have one or more substituents selected from group F, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from group H, or a hydrogen atom, where Y is an oxygen atom or -S(O) u -, p represents 0, 1, 2, 3, 4, 5, 6 or 7, and Q represents a C1-C8 chain hydrocarbon group which may have one or more substituents selected from group H, or a group selected from group G u represents 0, 1 or 2, R 11 and R 12 which are the same as or different from each other, represent a C1-C4 alkyl group which may have one or more halogen atoms, a halogen atom or a hydrogen atom, When p is 1, 2, 3, 4, 5, 6 or 7, 1, 2, 3, 4, 5, 6 or 7 Rs 11 and R 12 each independently may be the same or different, Group A: a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group E, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylcarbonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, phenyl, pyridyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl {the phenyl, the pyridyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the pyridazinyl, the pyrimidinyl and the pyrazinyl may have one or more substituents selected from Group B}, a halogen atom, a hydroxyl group, a cyano group and CONR 54 R 55 consisting of R 54 and R 55 which are the same as or different from each other, represent a C1-C4 alkyl group which may have one or more halogen atoms, or a hydrogen atom, Group B: a C1-C4 chain hydrocarbon group which may have one or more halogen atoms, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylthio group which may have one or more halogen atoms, a C1-C4 alkylsulfinyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a phenyl group which may have one or more halogen atoms, a phenoxy group which may have one or more halogen atoms, a cyano group, a nitro group, a carboxyl group, a hydroxyl group, a halogen atom and CONR 54 R 55 composed of the group, Group C: a C1-C4 chain hydrocarbon group which may have one or more halogen atoms, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group E, a C1-C4 alkoxy group which may have one or more halogen atoms, a C1-C4 alkylcarbonyl group which may have one or more halogen atoms, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a C1-C4 alkylsulfonyl group which may have one or more halogen atoms, phenyl, pyridyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl {the phenyl, the pyridyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the pyridazinyl, the pyrimidinyl and the pyrazinyl may have one or more substituents selected from Group B}, a halogen atom, a hydroxyl group, a cyano group and CONR 54 R 55 composed group, Group D: a group consisting of a hydroxyl group and a halogen atom, Group E: a group consisting of a C1-C4 alkoxy group which may have one or more halogen atoms, a cyano group, a hydroxyl group and a halogen atom, Group F: a C3-C8 alicyclic hydrocarbon group, an indanyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a naphthyl group, a pyridyl group, a quinolinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a furyl group, a thienyl group, a pyrrolidinyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuryl group, a benzothienyl group, a 1,3-benzodioxolyl group, a 1,4-benzodioxanyl group {the C3-C8 alicyclic hydrocarbon group, the indanyl group, the 1,2,3,4-tetrahydronaphthyl group, the phenyl group, the naphthyl group, the pyridyl group, the quinolinyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the furyl group, the thienyl group, the pyrrolidinyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the oxadiazolyl group, the thiadiazolyl group, the benzofuryl group, the benzothienyl group, the 1,3-benzodioxolyl group and the 1,4-benzodioxanyl group may have one or more substituents selected from Group C}, a C1-C4 alkoxycarbonyl group which may have one or more halogen atoms, a halogen atom, a cyano group, a nitro group, a carboxyl group, a hydroxyl group and CONR 54 R 55 comprising the group, Group G: a group consisting of a C3-C8 alicyclic hydrocarbon group, an indanyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a naphthyl group, a pyridyl group, a quinolinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a furyl group, a thienyl group, a pyrrolidinyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuryl group and a benzothienyl group {the C3-C8 alicyclic hydrocarbon group, the indanyl group, the 1,2,3,4-tetrahydronaphthyl group, the phenyl group, the naphthyl group, the pyridyl group, the quinolinyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the furyl group, the thienyl group, the pyrrolidinyl group, the pyrazolyl group, the imidazolyl group, the triazolyl group, the oxazolyl group, the isoxazolyl group, the thiazolyl group, the isothiazolyl group, the oxadiazolyl group, the thiadiazolyl group, the benzofuryl group and the benzothienyl group may have one or more substituents selected from group A}, Group H: C3-C8 cycloalkyl, indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, phenoxy, naphthyl, pyridyl, quinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolidinyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuryl, benzothienyl, 1,3-benzodioxolyl, 1,4-benzodioxanyl {the C3-C8 cycloalkyl, the indanyl, the 1,2,3,4-tetrahydronaphthyl, the phenyl, the phenoxy, the naphthyl, the pyridyl, the quinolinyl, the pyridazinyl, the pyrimidinyl, the pyrazinyl, the furyl, the thienyl, the pyrrolidinyl, the pyrazolyl, the imidazolyl, the triazolyl, the oxazolyl, the isoxazolyl, the thiazolyl, the isothiazolyl, the oxadiazolyl, the thiadiazolyl, the benzofuryl, the benzothienyl, the 1,3-benzodioxolyl and the 1,4-benzodioxanyl may have one or more substituents selected from Group C}, C1-C4 alkoxycarbonyl which may have one or more halogen atoms, halogen atom, cyano group, nitro group, carboxyl group, hydroxyl group and CONR 54 R 55 and the group consisting of.

2. The compound or its salt according to claim 1, wherein R 1 is a C1-C6 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

3. The compound or its salt according to claim 1 or claim 2, wherein, R 8 and R 9 are the same as or different from each other, and are a C1-C20 chain hydrocarbon group which may have one or more substituents selected from Group A, a C3-C6 alicyclic hydrocarbon group which may have one or more substituents selected from Group A, or a hydrogen atom.

4. The compound or its salt according to any one of claims 1 to 3, wherein, R 10 is a C1-C3 chain hydrocarbon group that may have one or more substituents selected from group D, or a hydrogen atom.

5. The compound or its salt according to any one of claims 1 to 4, wherein, n is 1.

6. The compound or its salt according to any one of claims 1 to 5, wherein, m is 0 or 1.

7. The compound or its salt according to any one of claims 1 to 5, wherein m is 0.

8. A pest arthropod control composition which contains an inert carrier and the compound or its salt according to any one of claims 1 to 7.

9. A composition which contains one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound or its salt according to any one of claims 1 to 7, Group (a): a group consisting of an insecticidal active ingredient, a miticidal active ingredient and a nematicidal active ingredient; Group (b): a bactericidal active ingredient; Group (c): a plant growth regulating ingredient; Group (d): a repellent ingredient.

10. A method for controlling harmful arthropods, wherein, Applying an effective amount of the compound or its salt according to any one of claims 1 to 7 or an effective amount of the composition according to claim 9 to a pest arthropod or the habitat of a pest arthropod.

11. A seed or vegetative propagation organ which retains an effective amount of the compound or its salt according to any one of claims 1 to 7 or an effective amount of the composition according to claim 9.

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