Heterocyclic compound and arthropod pest control composition containing the same

Description

TECHNICAL FIELD

[0001] The present invention relates to a certain class of heterocyclic compounds and a composition for controlling harmful arthropods comprising the compound, and to a method for controlling a harmful arthropod which comprises applying the compound or the composition.BACKGROUND ART

[0002] To date, in order to control harmful arthropods, some compounds have been studied. For example, it is described that a certain class of compound has an effect on controlling pests in Patent Documents 1 and 2.CITATION LISTPATENT DOCUMENT

[0003] Patent Document 1: WO 2013 / 191113 Patent Document 2: WO 2009 / 137651 SUMMARY OF THE INVENTION(PROBLEMS TO BE SOLVED BY INVENTION)

[0004] An object of the present invention is to provide a compound having an excellent efficacy for controlling harmful arthropods.(MEANS TO SOLVE PROBLEMS)

[0005] The present invention relates to the subject-matter as defined in the claims. In particular:

[0006] In an aspect, the present invention provides a compound represented by formula (I): wherein Q represents a group represented by formula Q1, n is 0, 1 or 2, R 2< represents an ethyl group, Y a< represents an oxygen atom, a sulfur atom, or NR 3a< , G 1< represents a nitrogen atom, or CR 5a< , G 2< represents a nitrogen atom, or CR 5b< , R 3a< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, R 5a< and R5 b< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR 12< , a halogen atom, or a hydrogen atom, A 2< represents CH, A 3< represents CH, A 4< represents CH, T represents OR 1< , R 1< represents a C1-C6 alkyl group which has one or more halogen atoms, R 12< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, S(O) 2 R 23< , or a hydrogen atom, R 23< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a phenyl group which may optionally have one or more substituents selected from Group D, Group C: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, and a halogen atom, Group D: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfonyl group which may optionally have one or more halogen atoms, an amino group, NHR 21< , NR 21< R 22< , C(O)R 21< , OC(O)R 21< , C(O)OR 21< , a cyano group, a nitro group, and a halogen atom, R 21< and R 22< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, Group F: a group consisting of a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a phenyl group which may optionally have one or more substituents selected from Group D, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a 3 to 7 membered nonaromatic heterocyclic group which may optionally have one or more substituents selected from Group C, an amino group, NHR 21< , NR 21< R 22< , and a cyano group, Group H: a group consisting of a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR 10< , NR 9< R 10< , C(O)R 10< , C(O)NR 9< R 10< , OC(O)R 9< , OC(O)OR 9< , NR 10< C(O)R 9< , NR 10< C(O)OR 9< , C(O)OR 10< , a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6- membered aromatic heterocyclic group, R 9< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, and R 10< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, or a hydrogen atom.

[0007] In another aspect, the present invention provides a composition for use in controlling a harmful arthropod comprising the above inventive compound and an inert carrier.

[0008] In another aspect, the present invention provides a method for controlling a harmful arthropod which comprises applying an effective amount of the above inventive compound to a harmful arthropod or a habitat where a harmful arthropod lives, wherein a method for the treatment of the human or animal body by therapy is excluded.

[0009] In still another aspect, the present invention provides a composition comprising one or more ingredients selected from Group (a) and Group (b), and the above inventive compound: Group (a): a group consisting of insecticidal ingredients, miticide ingredients, and nematicidal ingredients; and Group (b): fungicidal ingredient.

[0010] In still another aspect, the present invention provides a method for controlling a harmful arthropod which comprises applying an effective amount of the above inventive composition to a harmful arthropod or a habitat where a harmful arthropod lives, wherein a method for the treatment of the human or animal body by therapy is excluded.

[0011] In still another aspect, the present invention provides a seed or vegetative reproductive organ carrying an effective amount of the above inventive compound or an effective amount of the above inventive composition.

[0012] Generally, herein disclosed is a compound represented by formula (I): wherein Q represents a group represented by formula Q1, a group represented by formula Q2, or a group represented by formula Q3, n is 0, 1 or 2, R 2< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, a cyclopropyl group, or a cyclopropylmethyl group, Y a< represents an oxygen atom, a sulfur atom, or NR 3a< , Y b< represents an oxygen atom, a sulfur atom, or NR 3b< , Y c< represents an oxygen atom, a sulfur atom, or NR 3c< , G 1< represents a nitrogen atom, or CR 5a< , G 2< represents a nitrogen atom, or CR 5b< , G 3< represents a nitrogen atom, or CR 5c< , R 3a< , R 3b< , and R 3c< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group B, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group E, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, C(O)R 13< , C (O)OR 17< , C(O)NR 15a< R 16a< , C(O)NR 11< S(O) 2 R 23< , or a hydrogen atom, R 5a< , R 5b< , and R 5c< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group B, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group E, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, OR 12< , NR 11< R 12< , NR 11a< R 12a< , NR 24< NR 11< R 12< , NR 24< OR 11< , NR 11< C(O)R 13< , NR 24< NR 11< C(O)R 13< , NR 11< C(O)OR 14< , NR 24< NR 11< C(O)OR 14< , NR 11< C(O)NR 15a< R 16a< , NR 24< NR 11< C(O)NR 15a< R 16a< , N=CHNR 15a< R 16a< , N=S (O) x R 15< R 16< , C(O)R 13< , C(O)OR 17< , C(O)NR 15a< R 16a< , C(O)NR 11< S(O) 2 R 23< , CR 24< =NOR 17< , NR 11< CR 24< =NOR 17< , a cyano group, a nitro group, a halogen atom, or a hydrogen atom, x is 0 or 1, A 2< represents a nitrogen atom or CR 4a< , A 3< represents a nitrogen atom or CR 4b< , A 4< represents a nitrogen atom or CR 4c< , R 4a< , R 4b< , and R 4c< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a nitro group, OR 13< , NR 18< R 19< , a cyano group, a halogen atom, or a hydrogen atom, R 18< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, R 19< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a hydrogen atom, T represents a C1-C10 chain hydrocarbon group which have one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfinyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfonyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group which may optionally have one or more substituents selected from Group G, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group G, OR 1< , S(O) m R 1< , OS (O) 2 R 1< , CH 2 OR 1< , NR 1< R 29< , C(O)R 1< , C(O)NR 1< R 29< , NR 29< C (O)R 1< , N=CR 1< R 30< , a group represented by the following formula T-1, a group represented by the following formula T-2, a group represented by the following formula T-3, a group represented by the following formula T-4, a group represented by the following formula T-5, a group represented by the following formula T-6, a group represented by the following formula T-7, a group represented by the following formula T-8, a group represented by the following formula T-9, a group represented by the following formula T-10, a group represented by the following formula T-11, or a group represented by the following formula T-12, X 1< represents a nitrogen atom, or CR 1a< , X 2< represents a nitrogen atom or CR 1b< , X 3< represents a nitrogen atom or CR 1c< , X 4< represents a nitrogen atom or CR 1d< , X 3< represents a nitrogen atom or CR 1e< , R 1a< , R 1b< , R 1c< , R 1d< , and R 1e< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, a halogen atom, or a hydrogen atom, Y 1< represents NR 25< , an oxygen atom, or a sulfur atom, Y 2< represents a nitrogen atom, or CR 26< , Y 3< represents a nitrogen atom, or CR 27< , Y 4< represents a nitrogen atom, or CR 28< , R 25< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, R 26< , R 27< , and R 28< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, a halogen atom, or a hydrogen atom, R 1×< represents OR 7< , OS(O) 2 R 7< , S(O) m R 7< , NR 8< S(O) 2 R 7< , a C1-C5 chain hydrocarbon group which have one or more halogen atoms, a cyano group, or a halogen atom, R 1y< represents OR 7< , OS(O) 2 R 7< , S(O) m R 7< , NR 8< S(O) 2 R 7< , a cyano group, a C1-C5 chain hydrocarbon group which have one or more halogen atoms, or a halogen atom, R 1ay< and R 7< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which have one or more halogen atoms, R 8< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a hydrogen atom, m is 0, 1, or 2, R 1< represents a C1-C10 chain hydrocarbon group which have one or more halogen atoms, a (C1-C5 alkoxy)C2-CS alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfinyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfonyl)C2-C5 alkyl group which have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group which have one or more substituents selected from Group G, or a C3-C7 cycloalkyl group which have one or more substituents selected from Group G, R 11< , R 17< , R 24< , and R 29< are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a hydrogen atom, R 30< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a hydrogen atom, R 12< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, S(O) 2 R 23< , or a hydrogen atom, R 23< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a phenyl group which may optionally have one or more substituents selected from Group D, R 11a< and R 12a< combined together with a nitrogen atom to which they are attached to form a 3 to 7 membered nonaromatic heterocyclic group which may optionally have one or more substituents selected from Group E, R 13< represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may optionally have one or more halogen atoms, a phenyl group which may optionally have one or more substituents selected from Group D, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group D, or a hydrogen atom, R 14< represent a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may optionally have one or more halogen atom, or a (phenyl which may optionally have one or more substituents selected from Group D)C1-C3 alkyl group, R 15< and R 16< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, R 15a< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, and R 16a< represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group F, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group J, or a hydrogen atom, Group B: a group consisting of a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfanyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfonyl group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom, Group C: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, and a halogen atom, Group D: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfonyl group which may optionally have one or more halogen atoms, an amino group, NHR 21< , NR 21< R 22< , C(O)R 21< , OC(O)R 21< , C(O)OR 21< , a cyano group, a nitro group, and a halogen atom, R 21< and R 22< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, Group E: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group, Group F: a group consisting of a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a phenyl group which may optionally have one or more substituents selected from Group D, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a 3 to 7 membered nonaromatic heterocyclic group which may optionally have one or more substituents selected from Group C, an amino group, NHR 21< , NR 21< R 22< , and a cyano group, Group G: a group consisting of a C1-C6 alkyl group which have one or more halogen atoms, and a halogen atom, Group H: a group consisting of a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR 10< , NR 9< R 10< , C(O)R 10< , C(O)NR 9< R 10< , OC(O)R 9< , OC(O)OR 9< , NR 10< C(O)R 9< , NR 10< C(O)OR 9< , C(O)OR 10< , a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6- membered aromatic heterocyclic group, R 9< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, R 10< represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, Group J: a group consisting of a C1-C6 alkyl group which may optionally have one or more halogen atoms, a halogen atom, and a cyano group. [EFFECT OF INVENTION]

[0013] The present invention can control harmful arthropod.

[0014] The substituent(s) as described herein is / are explained. The term "halogen atom" represents fluorine atom, chlorine atom, bromine atom, or iodine atom.

[0015] When the substituents have two or more halogen atoms, these halogen atoms may be identical to or different from each other.

[0016] The expression of "CX-CY" as used herein represents that the number of carbon atom is from X to Y. For example, the expression of "C1-C6" represents that the number of carbon atom is from 1 to 6.

[0017] The term of "chain hydrocarbon group" represents an alkyl group, an alkenyl group, or an alkynyl group.

[0018] Examples of the term of "alkyl group" include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, and decyl group. Examples of the term of "alkenyl group" include vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group. 6-heptenyl group, 7-octenyl group, nonenyl group, and decenyl group.

[0019] Examples of the term of "alkynyl group" include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, 5-hexynyl group, 6-heptynyl group, 7-octynyl group, nonynyl group, and decynyl group.

[0020] Examples of the term of "cycloalkyl group" include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group.

[0021] The term of "alkoxy group" represents a group wherein the alkyl group as defied above is attached to an oxygen atom, and examples thereof include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, pentyloxy group, and hexyloxy group.

[0022] The term of "alkenyloxy group" represents a group wherein one hydrogen atom on the alkenyl group as defined above is replaced with an oxygen atom, and examples thereof include vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, isopropenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-isobutenyloxy group, 2-isobutenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, and 4-pentenyloxy group.

[0023] The term of "alkynyloxy group" represents a group wherein one hydrogen atom on the alkynyl group as defined above is replaced with an oxygen atom, and examples thereof include ethynyloxy group, 1-propynyloxy group, 2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-hexynyloxy group, 2-hexynyloxy group, and 3-hexynyloxy group.

[0024] Examples of "three(3)- to seven(7)- membered nonaromatic heterocyclic group" include aziridine ring, azetidine ring, pyrrolidine ring, imidazoline ring, imidazolidine ring, piperidine ring, tetrahydropyrimidine ring, hexahydropyrimidine ring, piperazine ring, azepane ring, oxazolidine ring, isoxazolidine ring, 1,3-oxazinane ring, morpholine ring, 1,4-oxazepane ring, thiazolidine ring, isothiazolidine ring, 1,3-thiazinane ring, thiomorpholine ring, and 1,4-thiazepane ring. Examples of the 3- to 7- membered nonaromatic heterocyclic ring which may optionally have one or more substituents selected from Group E include the below-mentioned group.

[0025] Examples of "C1-C10 chain hydrocarbon group which may optionally have one or more halogen atoms" include a C1-C10 chain hydrocarbon group which have one or more halogen atoms in addition to groups as exemplified above as "alkyl group", "alkenyl group" and "alkynyl group". Specific examples of "C1-C6 chain hydrocarbon group" and "C1-C5 chain hydrocarbon group" are encompassed by the "C1-C10 chain hydrocarbon group".

[0026] Examples of "C1-C5 alkyl group having three or more fluorine atoms" encompasses a perfluoroalkyl group, and examples thereof include trifluoromethyl group, 1,1,1-trifluoroethyl group, and trifluoroethyl group.

[0027] Examples of "C1-C6 alkoxy group which may optionally have one or more halogen atoms" include a C1-C6 alkoxy group which have one or more halogen atoms, in addition to the groups as exemplified above as "alkoxy group".

[0028] Examples of "C3-C7 cycloalkyl group which may optionally have one or more halogen atoms" include a C3-C7 cycloalkyl group which have one or more halogen atoms, in addition to the groups as exemplified above as "cycloalkyl group". Specific examples of "C3-C6 cycloalkyl group" are encompassed by the "C3-C7 cycloalkyl group".

[0029] The term of "(C1-C5 alkoxy)C2-C5 alkyl group which have one or more halogen atoms" represents a group wherein the (C1-C5 alkoxy) and / or (C2-C5 alkyl) has / have one or more halogen atoms, and examples thereof are a 2-(trifluoromethoxy)ethyl group, 2,2-difluoro-3-methoxypropyl group, 2,2-difluro-3-(2,2,2-trifluoroethoxy)propyl group, and 3-(2-chloroethoxy)propyl group.

[0030] The term of "(C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms" represents a group wherein (C1-C5 alkylsulfanyl group) and / or (C2-C5 alkyl) has / have one or more halogen atoms, and examples thereof include 2,2-difluoro-2-(trifluoromethylthio) ethyl group.

[0031] The term of "(C1-C5 alkylsulfinyl group)C2-C5 alkyl group which have one or more halogen atoms" represents a group wherein (C1-C5 alkylsulfinyl group) and / or (C2-C5 alkyl) has / have one or more halogen atoms, and examples thereof include 2,2-difluoro-2-(trifluoromethansulfinyl)ethyl group.

[0032] The term of "(C1-C5 alkylsulfonyl group)C2-C5 alkyl group which have one or more halogen atoms" represents a group wherein (C1-C5 alkylsulfonyl group) and / or (C2-C5 alkyl) has / have one or more halogen atoms, and examples of thereof include 2,2-difluoro-2-(trifluoromethansulfonyl) ethyl group.

[0033] The term of "(C3-C7 cycloalkyl)C1-C6 alkyl group which may optionally have one or more halogen atom" represents a group wherein (C3-C7 cycloalkyl) and / or (C1-C6 alkyl) may optionally have one or more halogen atoms, and examples thereof include (2,2-difluorocyclopropyl)methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, 2-(2,2-difluorocyclopropyl)-1,1,2,2,-tetrafluoroethyl group, (2,2-difluorocyclopropyl)propyl group, (2,2-difluorocyclopropyl)butyl group, (2,2-difluorocyclopropyl)pentyl group, and (2,2-difluorocyclopropyl)pentyl group. Specific examples of "(C3-C6 cycloalkyl)C1-C3 alkyl group" are encompassed by the term of "(C3-C7 cycloalkyl)C1-C6 alkyl group".

[0034] The term of "(C3-C7 cycloalkyl)C1-C3 alkyl group which may optionally have one or more substituents selected from Group G" represents a group wherein (C3-C7 cycloalkyl) and / or (C1-C3 alkyl) may optionally have one or more substituents selected from Group G, and examples thereof include (2,2-difluorocyclopropyl)methyl group, [1-(trifluoromethyl)cyclopropyl)}methyl group, [2-(trifluoromethyl)cyclopropyl]methyl group, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, 2-cyclopropyl-3,3,3-trifluoropropyl group, and 1,1,2,2-tetrafluoro-2-[2-(trifluoromethyl)cyclopropyl]ethyl group.

[0035] Examples of "phenyl which may optionally have one or more substituents selected from Group D)C1-C3 alkyl group" include benzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 4-(trifluoromethyl)benzyl group, and 2-[4-(trifluromethyl)phenyl]ethyl group.

[0036] The term of "a five(5)- or six(6)- membered aromatic heterocyclic group" represents a five(5) membered aromatic heterocyclic group or a six(6) membered aromatic heterocyclic group, and examples of the five(5) membered aromatic heterocyclic group include pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, and thiadiazolyl group. Examples of the six(6) membered aromatic heterocyclic group include pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, and tetrazinyl group.

[0037] The terms of "alkylsulfanyl group", "alkylsulfinyl group", and "alkylsulfonyl group" represent an alkyl group containing a S(O) y moiety, which represents an alkylsulfanyl group, an alkylsulfinyl group, or an alkylsulfonyl group, when y is 0, 1 or 2 respectively.

[0038] The term of "alkylsulfanyl group" represents a sulfanyl group containing the above-mentioned alkyl group, and examples thereof include a methyl sulfanyl group, an ethyl sulfanyl group, a propyl sulfanyl group, and an isopropyl sulfanyl group.

[0039] The term of "alkylsulfinyl group" represents a sulfinyl group containing the above-mentioned alkyl group, and examples thereof include a methyl sulfinyl group, an ethyl sulfinyl group, a propyl sulfinyl group, and an isopropyl sulfinyl group.

[0040] The term of "alkylsulfonyl group" represents a sulfonyl group containing the above-mentioned alkyl group, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group.

[0041] The compound of the present invention (the inventive compound) may exist as one or more stereoisomers. Examples of the stereoisomer include enantiomer, diastereoisomer, and geometric isomer. Each stereoisomer, and stereoisomer mixture(s) in an arbitrary ratio thereof are included in the present invention.

[0042] The inventive compound may form acid addition salts. Examples of the acid to form the acid addition salt include 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. The acid addition salt may be obtained by mixing the compound with an acid.

[0043] The following Embodiments disclose compounds described herein. Compounds of the claimed invention are those as defined in the claims. Compounds not within the claims are disclosed only for illustrative purposes.

[0044] [Embodiment 1] The compound wherein R 3a< , R 3b< and R 3c< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may optionally have one or more substituents selected from Group H} or a hydrogen atom, R 5a< , R 5b< and R 5c< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group may optionally have one or more substituents selected from Group H}, OR 12< , NR 11< R 12< , NR 11< C(O)OR 14< , a halogen atom, or a hydrogen atom. [Embodiment 2] The compound wherein R 3a< , R 3b< and R 3c< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, R 5a< , R 5b< and R 5c< are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR 12< , a halogen atom, or a hydrogen atom. [Embodiment 3] The compound according to Embodiment 1 wherein R 2< represents C1-C6 alkyl group. [Embodiment 4] The compound wherein R 2< represents an ethyl group. [Embodiment 5] The compound according to Embodiment 1 wherein R 2< represents an ethyl group. [Embodiment 6] The compound according to Embodiment 2 wherein R 2< represents an ethyl group. [Embodiment 7] The compound according to Embodiment 3 wherein Q represents a group represented by formula Q1, or a group represented by formula Q3. [Embodiment 8] The compound according to Embodiment 4 wherein Q represents a group represented by formula Q1, or a group represented by formula Q3. [Embodiment 9] The compound according to Embodiment 5 wherein Q represents a group represented by formula Q1, or a group represented by formula Q3. [Embodiment 10] The compound according to Embodiment 6 wherein Q represents a group represented by formula Q1, or a group represented by formula Q3. [Embodiment 11] The compound according to Embodiment 8 wherein Y c< represents an oxygen atom or sulfur atom. [Embodiment 12] The compound according to Embodiment 7 wherein Y a< represents an oxygen atom or a sulfur atom, Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 13] The compound according to Embodiment 8 wherein Y a< represents an oxygen atom or a sulfur atom, Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 14] The compound according to Embodiment 9 wherein Y a< represents an oxygen atom or a sulfur atom, Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 15] The compound according to Embodiment 10 wherein Y a< represents an oxygen atom or a sulfur atom, Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 16] The compound according to Embodiment 7 wherein Y a< and Y c< represent a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 17] The compound according to Embodiment 8 wherein Y a< and Y c< represent a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 18] The compound according to Embodiment 9 wherein Y a< and Y c< represent a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 19] The compound according to Embodiment 10 wherein Y a< and Y c< represent a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 20] The compound according to Embodiment 4 wherein Q represents a group represented by formula Q1. [Embodiment 21] The compound according to Embodiment 5 wherein Q represents a group represented by formula Q1. [Embodiment 22] The compound according to Embodiment 6 wherein Q represents a group represented by formula Q1. [Embodiment 23] The compound according to Embodiment 20 wherein G 2< represents CR 5b< . [Embodiment 24] The compound according to Embodiment 21 wherein G 2< represents CR 5b< . [Embodiment 25] The compound according to Embodiment 22 wherein G 2< represents CR 5b< . [Embodiment 26] The compound according to Embodiment 20 wherein Y a< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 27] The compound according to Embodiment 21 wherein Y a< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 28] The compound according to Embodiment 22 wherein Y a< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 29] The compound according to Embodiment 4 wherein Q represents a group represented by formula Q2. [Embodiment 30] The compound according to Embodiment 5 wherein Q represents a group represented by formula Q2. [Embodiment 31] The compound according to Embodiment 6 wherein Q represents a group represented by formula Q2. [Embodiment 32] The compound according to Embodiment 29 wherein Y b< represents NR 3b< , G 1< represents CR 5a< , and G 3< represents a nitrogen atom. [Embodiment 33] The compound according to Embodiment 30 wherein Y b< represents NR 3b< , G 1< represents CR 5a< , and G 3< represents a nitrogen atom. [Embodiment 34] The compound according to Embodiment 31 wherein Y b< represents NR 3b< , G 1< represents CR 5a< , and G 3< represents a nitrogen atom. [Embodiment 35] The compound according to Embodiment 4 wherein Q represents a group represented by formula Q3. [Embodiment 36] The compound according to Embodiment 5 wherein Q represents a group represented by formula Q3. [Embodiment 37] The compound according to Embodiment 6 wherein Q represents a group represented by formula Q3. [Embodiment 38] The compound according to Embodiment 35 wherein Y c< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 39] The compound according to Embodiment 36 wherein Y c< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 40] The compound according to Embodiment 37 wherein Y c< represents an oxygen atom or a sulfur atom, and G 2< represents CR 5b< . [Embodiment 41] The compound according to Embodiment 35 wherein Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 42] The compound according to Embodiment 36 wherein Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 43] The compound according to Embodiment 37 wherein Y c< represents a sulfur atom, G 2< represents CR 5b< , and G 3< represents a nitrogen atom. [Embodiment 44] The compound according to Embodiment 3 wherein A 2< represents CR 4a< , A 4< represents CR 4c< , and R 4a< , R 4b< , and R 4c< are identical to or different from each other, and each represents a hydrogen atom or a halogen atom. [Embodiment 45] The compound according to Embodiment 12 A 2< represents CR 4a< , A 4< represents CR 4c< , and R 4a< , R 4b< , and R 4c< are identical to or different from each other, and each represents a hydrogen atom or a halogen atom. [Embodiment 46] The compound according to Embodiment 16 A 2< represents CR 4a< , A 4< represents CR 4c< , and R 4a< , R 4b< , and R 4c< are identical to or different from each other, and each represents a hydrogen atom or a halogen atom. [Embodiment 47] The compound according to Embodiment 20 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 48] The compound according to Embodiment 21 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 49] The compound according to Embodiment 22 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 50] The compound according to Embodiment 23 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 51] The compound according to Embodiment 24 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 52] The compound according to Embodiment 25 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 53] The compound according to Embodiment 26 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 54] The compound according to Embodiment 27 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 55] The compound according to Embodiment 28 A 2< and A 4< represent CH, and A 3< represents a nitrogen atom or CH. [Embodiment 56] The compound according to Embodiment 20 A 2< , A 3< , and A 4< represent CH. [Embodiment 57] The compound according to Embodiment 21 A 2< , A 3< , and A 4< represent CH. [Embodiment 58] The compound according to Embodiment 22 A 2< , A 3< , and A 4< represent CH. [Embodiment 59] The compound according to Embodiment 23 A 2< , A 3< , and A 4< represent CH. [Embodiment 60] The compound according to Embodiment 24 A 2< , A 3< , and A 4< represent CH. [Embodiment 61] The compound according to Embodiment 25 A 2< , A 3< , and A 4< represent CH. [Embodiment 62] The compound according to Embodiment 26 A 2< , A 3< , and A 4< represent CH. [Embodiment 63] The compound according to Embodiment 27 A 2< , A 3< , and A 4< represent CH. [Embodiment 64] The compound according to Embodiment 28 A 2< , A 3< , and A 4< represent CH. [Embodiment 65] The compound according to any one of Embodiment 1 to Embodiment 64 wherein T represents a C1-C10 chain hydrocarbon group which have one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfinyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfonyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group which have one or more substituents selected from Group G, a C3-C7 cycloalkyl group which have one or more substituents selected from Group G, OR 1< , S (O) m R 1< , OS(O) 2 R 1< , NR 1< R 29< , a group represented by formula T-1, a group represented by formula T-2, a group represented by formula T-3, a group represented by formula T-4, a group represented by formula T-5, a group represented by formula T-6, a group represented by formula T-7, or a group represented by formula T-8. [Embodiment 66] The compound according to any one of Embodiment 1 to Embodiment 64 wherein T represents a C1-C10 chain hydrocarbon group which have one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfinyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfonyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group which have one or more substituents selected from Group G, a C3-C7 cycloalkyl group which have one or more substituents selected from Group G, OR 1< , S(O) m R 1< , OS(O) 2 R 1< , or NR 1< R 29< . [Embodiment 67] The compound according to any one of Embodiment 1 to Embodiment 64 wherein T represents OR 1< . [Embodiment 68] The compound according to any one of Embodiment 1 to Embodiment 64 wherein T represents OR 1< , and R 1< represents a C1-C6 alkyl group which have one or more halogen atoms.

[0045] Next, a process for preparing a compound as described herein is disclosed. Compounds according to the claimed invention are those as defined in the claims.Process 1

[0046] A compound represented by formula (A-1a) (hereinafter, referred to as "Compound (A-1a)", a compound represented by formula (A-1b) (hereinafter, referred to as "Compound (A-1b)", and a compound represented by formula (A-1c) "hereinafter, referred to as "Compound (A-1c)" can be prepared according to the below-mentioned scheme. [wherein X represents a chlorine atom, a bromine atom, or an iodine atom, and the other symbols are the same as those defined above.]

[0047] The compound (A-1a) can be prepared by reacting a compound represented by formula (M-2) (hereinafter, referred to as "Compound (M-2)" with a compound represented by formula (R-1) "hereinafter, referred to as "Compound (R-1)" in the presence of a catalyst and a base.

[0048] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include alcohols (such as methanol and ethanol) (hereinafter, collectively referred to as "alcohols"); nitriles (such as acetonitrile) (hereinafter, collectively referred to as "nitriles") ; ethers (such as methyl tert-butyl ether (hereinafter, referred to as "MTBE"), tetrahydrofuran "hereinafter, referred to as "THF") and dimethoxyethane (hereinafter, collectively "ethers"); aromatic hydrocarbons (such as toluene and xylene) (hereinafter, collectively referred to as "aromatic hydrocarbons"); apromatic polar solvents (such as N,N-dimethylformamide (hereinafter, referred to as "DMF"), and N-methylpyrrolidone and dimethylsulfoxide (hereinafter, referred to as "DMSO") (hereinafter, collectively referred to as "aprotic polar solvents"); water; and mixed solvents of these two or more solvents.

[0049] Examples of the catalyst to be used in the reaction include palladium catalysts (such as tetrakis(triphenylphosphine) palladium (0), 1,1'-bis(diphenylphosphino) ferrocene palladium (II) dichloride, tris (dibenzylideneacetone) dipalladium (0), and palladium (II) acetate); nickel catalysts (such as bis(cyclooctadiene) nickel(0) and nickel(II) chloride); and copper catalysts (such as copper (I) iodide and copper (I) chloride).

[0050] Examples of the base to be used in the reaction include alkali metal hydrides (such as sodium hydride) (hereinafter, collectively referred to as "alkali metal hydrides"); alkali metal carbonates (such as potassium carbonate and sodium carbonate) (hereinafter, collectively referred to as "alkali metal carbonates"); and organic bases (such as pyridine and triethylamine) (hereinafter, collectively referred to as "organic bases").

[0051] In the reaction, the compound (R-1) is usually used within a range of 1 to 20 molar ratio(s), the metal catalyst is usually used within a range of 0.01 to 0.5 molar ratios, and the base is usually used within a range of 0.1 to 5 molar ratio (s), as opposed to 1 mole of the compound (M-2).

[0052] A ligand may be used in the reaction. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenlnyl, 1,2-bis (diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyqunoline, and 1,10-phenanthroline, and the others. When a ligand is used in the reaction, the ligand is usually used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (M-2).

[0053] The reaction temperature in the reaction is usually within a range of -20 to 200°C. The reaction period in the reaction is usually within a range of 0.1 to 72 hours.

[0054] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (A-1a).

[0055] The compound (R-1) is a commercially available compound, or can be prepared by using a known method.

[0056] The compound (A-b) can be prepared by reacting the compound (A-1a) with an oxidizing agent.

[0057] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include halogenated hydrocarbons (such as dichloromethane and chloroform) (hereinafter, collectively referred to as "halogenated hydrocarbons"); nitriles; alcohols; acetic acid; water; and mixed solvents of two or more of these solvents.

[0058] Examples of the oxidizing agent to be used in the reaction include sodium periodate, m-chloroperoxybenzoic acid (hereinafter, referred to as "mCPBA") and hydrogen peroxide.

[0059] When hydrogen peroxide is used as an oxidizing agent, a base or a catalyst may be used as needed.

[0060] Examples of the base include sodium carbonate. When the base is used in the reaction, the base is usually used within a range of 0.01 to 1 molar ratio(s), as opposed to 1 mole of the compound (A-1a).

[0061] Examples of the catalyst include tungstic acid, and sodium tungstate. When the catalyst is used in the reaction, the catalyst is usually used within a range of 0.01 to 0.5 molar ratios as opposed to 1 mole of the compound (A-1a).

[0062] In the reaction, the oxidizing agent is usually used within a range of 1 to 1.2 molar ratio(s), as opposed to 1 mole of the compound (A-1a).

[0063] The reaction temperature in the reaction is usually within a range of -20 to 80°C. The reaction period in the reaction is usually within a range of 0.1 to 12 hours.

[0064] When the reaction is completed, water is added to reaction mixtures, and the mixtures are extracted with organic solvent(s), and if necessary, the organic layers are washed with an aqueous solution of a reducing agent (such as sodium sulfite, and sodium thiosulfate) and an aqueous solution of a base (such as sodium hydrogen carbonate). The resulting organic layers are dried and concentrated to obtain the compound (A-1b).

[0065] The compound (A-1c) can be prepared by reacting the compound (A-1b) with the oxidizing agent.

[0066] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixed solvents of two or more of these solvents.

[0067] Examples of the oxidizing agent to be used in the reaction include mCPBA and hydrogen peroxide.

[0068] When hydrogen peroxide is used as an oxidizing agent, a base or a catalyst may be used as needed.

[0069] Examples of the base include sodium carbonate. When a base is used in the reaction, the base is usually used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (A-1b).

[0070] Examples of the catalyst include sodium tungstate. When the catalyst is used in the reaction, the catalyst is usually used within a range of 0.01 to 0.5 molar ratios as opposed to 1 mole of the compound (A-1b).

[0071] In the reaction, the oxidizing agent is usually used within a range of 1 to 2 molar ratio(s) as opposed to 1 mole of the compound (A-1b).

[0072] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction is usually within a range of 0.1 to 12 hours.

[0073] When the reaction is completed, water is added to reaction mixtures, and the mixtures are extracted with organic solvent(s), and if necessary, the organic layers are washed with an aqueous solution of a reducing agent (such as sodium sulfite, and sodium thiosulfate) and an aqueous solution of a base (such as sodium hydrogen carbonate). The resulting organic layers are dried and concentrated to obtain the compound (A-1c).

[0074] Also the compound (A-1c) can be prepared by reacting the compound (A-1a) with an oxidizing agent in one step (one-spot)

[0075] The reaction can be carried out by using the oxidizing agent in 2 to 5 molar ratios as opposed to 1 mole of the compound (A-1a) according to a similar method to that described in the method for preparing the compound (A-1c) from the compound (A-1b).Process 2

[0076] A compound represented by formula (A-2a) (hereinafter, referred to as "Compound (A-2a)") can be prepared by reacting a compound represented by formula (M-3) (hereinafter, referred to as "Compound (M-3)") with the compound (R-1) in the presence of a catalyst and a base. A compound represented by formula (A-2b) (hereinafter, referred to as "Compound (A-2b)") or a compound represented by formula (A-2c) (hereinafter, referred to as "Compound (A-2c)") can be prepared by reacting the compound (A-2a) with an oxidizing agent. The compound (A-2c) can be prepared by reacting the compound (A-2b) with an oxidizing agent. [wherein the symbols are the same as those defined above.]

[0077] These reactions can be carried out according to the Process 1.Process 3

[0078] A compound represented by formula (A-3a) (hereinafter, referred to as "Compound (A-3a)") can be prepared by reacting a compound represented by formula (M-5) (hereinafter, referred to as "Compound (M-5)") with the compound (R-1) in the presence of a catalyst and a base. A compound represented by formula (A-3b) (hereinafter, referred to as "Compound (A-3b)") or a compound represented by formula (A-3c) (hereinafter, referred to as "Compound (A-3c)") can be prepared by reacting the compound (A-3a) with an oxidizing agent. The compound (A-3c) can be also prepared by reacting the compound (A-3b) with an oxidizing agent. [wherein the symbols are the same as those defined above]

[0079] These reactions can be carried out according to the Process 1.Process 4

[0080] A compound represented by formula (A-4) (hereinafter, referred to as "Compound (A-4)") can be prepared according to the below-mentioned scheme. [wherein X b< represents a chlorine atom or a bromine atom, and the other symbols are the same as those defined above.]

[0081] A compound represented by formula (M-6) (hereinafter, referred to as "Compound (M-6)") can be prepared by reacting a compound represented by formula (M-16) (hereinafter, referred to as "Compound (M-16)") with a compound represented by formula (R-2) (hereinafter, referred to as "Compound (R-2)") in the presence of a base.

[0082] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0083] Examples of the bases to be used in the reaction include alkali metal carbonates, and alkali metal hydrides.

[0084] In the reaction, the compound (R-2) is usually used within a range of 1 to 2 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-16).

[0085] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0086] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (M-6).

[0087] The compound (M-16) is a known compound, or can be prepared according to a similar method to those described in WO 2016 / 121969 or WO 2017 / 065228 and so on.

[0088] The compound (R-2) is a commercially available compound, or can be prepared by using a known method.

[0089] A compound represented by formula (M-7) (hereinafter, referred to as "Compound (M-7)") can be prepared by reacting the compound (M-6) with an ozone, followed by reacting Lhe resulting ozonide with a reducing agent.

[0090] The reaction between the compound (M-6) and an ozone is usually carried out in a solvent. Examples of the solvents to be used in the reaction include aromatic hydrocarbons, halogenated hydrocarbons, nitriles, aprotic polar solvents, alcohols, water, and mixed solvents of two or more of these solvents.

[0091] In the reaction between the compound (M-6) and an ozone, the ozone is usually used within a range of 1 to 100 molar ratio(s) as opposed to 1 mole of the compound (M-6).

[0092] The reaction temperature of the reaction between the compound (M-6) and an ozone is usually within a range of - 78 to 30°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0093] When the reaction between the compound (M-6) and an ozone is completed, the reaction mixture containing an ozonide are reacted with a reducing agent, and water is added to reaction mixtures, and the mixtures are extracted with organic solvents, and the organic layers are worked up (for example, drying and concentration) to obtain the compound (M-7). Examples of the reducing agent include zinc and dimethyl sulfide.

[0094] The ozone can be prepared by using a known method.

[0095] A compound represented by formula (A-4) (hereinafter, referred to as "Compound (A-4)") can be prepared by reacting the compound (M-7), a compound represented by formula (R-3) (hereinafter, referred to as "Compound (R-3)") and a compound represented by formula (R-4) (hereinafter, referred to as "Compound (R-4)").

[0096] The reaction can be usually in a solvent. Examples of the solvents to be used in the reactions include aromatic hydrocarbons, nitriles, and mixed solvents of two or more of these solvents.

[0097] In the reaction, the compound (R-3) is usually used within a range of 1 to 10 molar ratio(s), and the compound (R-4) is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-7).

[0098] The reaction temperature in the reaction is usually within a range of 0 to 120°C. The reaction period in the reaction is usually within a range of 0.1 to 48 hours.

[0099] When the reaction is completed, the reaction mixtures are worked up as usual to obtain the compound (A-4).

[0100] The compound (R-3) and the compound (R-4) are commercially available compounds or can be prepared by using the known method.Process 5

[0101] A compound represented by formula (A-5) (hereinafter, referred to as "Compound (A-5)") can be prepared by reacting the compound (M-7) with an acid. [wherein the symbols are the same as those defined above.]

[0102] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0103] Examples of the acid to be used in the reaction include polyphosphoric acid, 10-camphorsulfonic acid, and pyridinium p-toluene sulfonate, and the others.

[0104] In the reaction, the acid is usually within a range of 0.1 to 2 molar ratios, as opposed to 1 mole of the compound (M-7).

[0105] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0106] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (M-5).Process 6

[0107] A compound represented by formula (A-6) (hereinafter, referred to as "Compound (A-6)") can be prepared by reacting the compound (M-7) with a sulfurizing agent. [wherein the symbols are the same as those defined above]

[0108] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, and mixed solvents of two or more of these solvents.

[0109] Examples of the sulfurizing agents to be used in the reaction include 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide (hereinafter, referred to as "Lawesson's reagent") and phosphorus pentasulfide.

[0110] In the reaction, the sulfurizing agent is usually used within a range of 1 to 2 molar ratio(s), as opposed to 1 mole of the compound (M-7).

[0111] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0112] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (A-6).Process 7

[0113] A compound represented by formula (A-7) (hereinafter, referred to as "Compound (A-7)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above.]

[0114] A compound represented by formula (M-9) (hereinafter, referred to as "Compound (M-9)") can be prepared by reacting a compound represented by formula (M-4) (hereinafter, referred to as "Compound (M-4)") with a compound represented by formula (R-5) (hereinafter, referred to as "Compound (R-5)") in the presence of a base.

[0115] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0116] Examples of the base to be used in the reaction include alkali metal carbonates and alkali metal hydrides.

[0117] In the reaction, the Compound (R-5) is usually used wthin a range of 1 to 2 molar ratio(s), and the base is usually within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-4).

[0118] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0119] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (M-9).

[0120] The compound (R-5) is a commercially available compound, or can be prepared according to a known method.

[0121] The compound (A-7) can be prepared by reacting the compound (M-9) with the compound (R-3) in the presence of an acid.

[0122] The reaction can be carried out by using the compound (M-9) in place of the compound (M-7) according to the Process 5.Process 8

[0123] A compound represented by formula (A-8) (hereinafter, referred to as "Compound (A-8)") can be prepared by reacting the compound (M-9) with a halogenating agent. [Wherein the symbols are the same as those defined above]

[0124] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, halogenated hydrocarbons, and mixed solvents of two or more of these solvents.

[0125] Examples of the halogenating agent to be used in the reaction include phosphoryl chloride and phosphoryl bromide, and the others.

[0126] In the reaction, the halogenating agent is usually within a range of 1 to 10 molar ratio(s) as opposed to 1 mole of the compound (M-9).

[0127] The reaction temperature in the reaction is usually within a range of 20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0128] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (A-8).Process 9

[0129] A compound represented by formula (A-9) (hereinafter, referred to as "Compound (A-9)") can be prepared by reacting the compound (M-9) with a sulfurizing agent. [Wherein the symbols are the same as those defined above]

[0130] The compound (A-9) can be prepared by using the compound (M-9) in place of the compound (M-7) according to a similar method to that for preparing the compound (A-6) from the compound (M-7), said method being described in the process 6.Process 10

[0131] A compound represented by formula (A-10) (hereinafter, referred to as "Compound (A-10)") and a compound represented by formula (A-11) (hereinafter, referred to as "Compound (A-11)") can be prepared according to the below-mentioned scheme. [wherein T X< represents a C1-C3 alkyl group, R 3< represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group B, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group E, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, C(O)R 13< , C(O)R 17< , C(O)NR 15a< R 16a< , C(O)NR 11< S(O) 2 R 23< , or a hydrogen atom, R 5< represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group B, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group E, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, OR 12< , NR 11< R 12< , NR 11a< R 12a< , NR 24< NR 11< R 12< , NR 24< OR 11< , NR 11< C(O)R 13< , NR 24< NR 11< C(O)R 13< , NR 11< C(O)OR 14< , NR 24< NR 11< C(O)OR 14< , NR 11< C(O)NR 15a< R 16a< , NR 24< NR 11< C(O)NR 15a< R 16a< , N=CHNR 15a< R1 6a< , N=S(O) x R 15< R 16< , C(O)R 13< , C(O)R 17< , C(O)NR 15a< R 16a< , C(O)NR 11< S(O) 2 R 23< , CR 24< =NOR 17< , NR 11< CR 24< =NOR 17< , a cyano group, a nitro group, a halogen atom, or a hydrogen atom, and the other symbols are the same as those defined above.]

[0132] A compound represented by formula (M-10) (hereinafter, referred to as "Compound (M-10)") can be prepared by reacting the compound (M-16) with a compound represented by formula (R24) (hereinafter, referred to as "Compound (R24)").

[0133] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0134] In the reaction, the compound (R24) is usually used within a range of 1 to 100 molar ratio(s) as opposed to 1 mole of the compound (M-16).

[0135] The reaction temperature in the reaction is usually within a range of 0 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0136] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (M-10).

[0137] The compound (R24) is a commercially available compound, or can be prepared according to a similar method to that described in WO 2013 / 185928.

[0138] The compound (A-10) and the compound (A-11) can be prepared by reacting the compound (M-10) with a compound represented by formula (R-6) (hereinafter, referred to as "Compound (R-6)").

[0139] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixed solvents of two or more of these solvents.

[0140] In the reaction, the compound (R-6) is usually used within a range of 1 to 5 molar ratio(s) as opposed to 1 mole of the compound (M-10).

[0141] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usualy within a range of 0.1 to 24 hours.

[0142] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (M-10) and the compound (M-11).

[0143] The compound (R-6) is a commercially available compound, or can be prepared by using a known method.Process 11

[0144] A compound represented by formula (A-12) (hereinafter, referred to as "Compound (A-12)") and a Compound represented by formula (A-13) (hereinafter, referred to as "Compound (A-13)") can be prepared by reacting the compound (M-10) with hydroxylamine. [wherein the symbols are the same as those defined above]

[0145] The reaction can be carried out by using hydroxylamine in place of the compound (R-6) according to the Process 10. Examples of hydroxylamine include anhydrous hydroxylamine, hydroxylamine hydrochloride salt, and hydroxylamine hydrate, and the others.Process 12

[0146] A compound represented by formula (A-14) (hereinafter, referred to as "Compound (A-14)"), a compound represented by formula (A-15) (hereinafter, referred to as "Compound (A-15)"), a compound represented by formula (A-16) (hereinafter, referred to as "Compound (A-16)"), and a compound represented by formula (A-17) (hereinafter, referred to as "Compound (A-17)") can be prepared according the below-mentioned scheme. [wherein R 3a< represents a C1-C6 chain hydrocarbon group which may optionally have one or more substituents selected from Group B, a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group E, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, C(O)R 13< , C(O)R 17< , C(O)NR 15a< R 16a< , or C(O)NR 11< S(O) 2 R 23< , and the other symbols are the same as those defined above.]

[0147] A compound represented by formula (M-29) (hereinafter, referred to as "Compound (M-29)") can be prepared by reacting a compound represented by formula (M-8) (hereinafter, referred to as "Compound (M-8)"), a palladium catalyst (such as [1, 1'-bis(diphenylphoshino)ferrocene] palladium (II) dichloride), carbon monooxide, and triethyl silane. The reaction can be conducted according to a similar method to that described in Organic Process Research & Development, 11 (1) , 39-43, 2007.

[0148] A compound represented by formula (M-30) (hereinafter, referred to as "Compound (M-30)") can be prepared by reacting the compound (M-29), nitromethane and triethylamine. The reaction can be carried out according to a similar method to that described in Journal of Medicinal Chemistry (2014), 57, (10), 4382.

[0149] A compound represented by formula (M-31) (hereinafter, referred to as "Compound (M-31)") can be prepared by reacting the compound (M-30), sodium azide, and aluminium chloride. The reaction can be conducted according to a similar method to that described in Advanced Synthesis & Catalysis (2016), 358, (10), 1689.

[0150] A compound represented by formula (M-32) (hereinafter, referred to as "Compound (M-32)") can be prepared by reacting the compound (M-31) with N-chlorosuccinimide, N-bromosuccinimide, or N-iodosuccinimide. The reaction can be conducted according to a similar method to that described in Organic Letters (2009), 11, (23), 5490.

[0151] The compound (A-14) can be prepared by using the compound (M-32) in place of the compound (M-3) according to the method for preparing the compound (A-2a) from the compound (M-3) which is described in the process 2.

[0152] The compound (A-15), the compound (A-16), and the compound (A-17) can be prepared by reacting the compound (A-14) with a compound represented by formula (R-7) (hereinafter, referred to as "Compound (R-7)") in the presence of a base.

[0153] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0154] Examples of the bases to be used in the reaction include organic bases, alkali metal hydrides, and alkali metal carbonates.

[0155] In the reaction, the compound (R-7) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 0.1 to 5 molar ratios, as opposed to 1 mole of the compound (A-14).

[0156] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0157] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (A-15), the compound (A-16) and the compound (A-17).

[0158] The compound (R-7) is a commercially available Compound, or can be prepared by using a known method.Process 13

[0159] A compound represented by formula (A-18) (hereinafter, referred to as "Compound (A-18)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0160] A compound represented by formula (M-33) (hereinafter, referred to as "Compound (M-33)") can be prepared by reacting a compound represented by formula (M-14) (hereinafter, referred to as "Compound (M-14)"), a compound represented by formula (R8) (hereinafter, referred to as "Compound (R8)"), and a base (such as butyl lithium). The reaction can be carried out according to a similar method to that described in Journal of the American Chemical Society (2008), 130, (30), 9942.

[0161] The compound (R) is a commercially available compound, or can be prepared by using the known method.

[0162] A compound represented by formula (M-34) (hereinafter, referred to as "Compound (M-34)") can be prepared by reacting the compound (M-33) with O-methyl hydroxylamine. The reaction can be carried out according to a similar method to that described in Journal of Organic Chemistry (2007), 72, (25), 9643.

[0163] A compound represented by formula (M-35) (hereinafter, referred to as "Compound (M-35)") can be prepared by reacting the compound (M-34) with N-chlorosuccinimide, N-bromosuccinimide, or N-iodosuccinimide. The reaction can be carried out according to a similar method to that described in Journal of Organic Chemistry (2007), 72, (25), 9643.

[0164] The compound (A-18) can be prepared by using the compound (M-35) in place of the compound (M-3) according to a similar method to that for preparing the Compound (A-2a) from the Compound (M-3), said method being described in the Process 2.Process 14

[0165] A compound represented by formula (A-19) (hereinafter, referred to as "Compound (A-19)") and a compound represented by formula (A-20) (hereinafter, referred to as "Compound (A-20)") can be prepared according to the below-mentioned scheme. [wherein TIPS represents a triisopropylsilyl group, and the other symbols are the same as those defined above]

[0166] A compound represented by formula (M-36) (hereinafter, referred to as "Compound (M-36)") can be prepared by reacting a compound represented by formula (M-1) (hereinafter, referred to as "Compound (M-1)") with hexamethylenetetramine. The reaction is carried out according to a method described in Medicinal Chemistry (2014), 57, (5), 2058.

[0167] A compound represented by formula (M-37) (hereinafter, referred to as "Compound (M-37)") can be prepared by reacting the compound (M-36) with the compound (R-8). The reaction can be carried out according to a similar method to that described in Journal of Organic Chemistry (2016), 81, (9), 3688.

[0168] A compound represented by formula (M-38) (hereinafter, referred to as "Compound (M-38)") can be prepared by reacting the compound (M-37) with triisopropylsilylchloride. The reaction can be carried out according to a similar method to that described in RSC Advances (2016), 6, (41), 3, 4428.

[0169] A compound represented by formula (M-39) (hereinafter, referred to as "Compound (M-39)") can be prepared by reacting the compound (M-38) with N-bromosuccinimide. The reaction can be carried out according to a similar method to that described in WO 2010 / 135530.

[0170] A compound represented by formula (M-40) (hereinafter, referred to as "Compound (M-40)") can be prepared by using the compound (M-39) in place of the compound (M-3) according to a similar method that for preparing the compound (A-2a) from the compound (M-3).

[0171] The compound (A-19) can be prepared by reacting the compound (M-40) with tetrabutyl ammonium fluoride.

[0172] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0173] In the reaction, tetrabutyl ammonium fluoride is usually used within a range of 1 to 2 molar ratio(s) as opposed to 1 mole of the compound (M-40).

[0174] The reaction temperature in the reaction is usually within a range of -20 to 100°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0175] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (A-19).

[0176] The compound (A-20) can be prepared by reacting the compound (A-19) with the compound (R-7). The reaction can be carried out by using the compound (A-19) in place of the compound (A-14) according to a similar method to that for preparing the compound (A-15) from the compound (A-14), said method being described in the Process 12.Process 15

[0177] A compound represented by formula (A-21) (hereinafter, referred to as "Compound (A-21)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above.]

[0178] A compound represented by formula (AM-42) (hereinafter, referred to as "Compound (M-42)") can be prepared by reacting a compound represented by formula (M-41) (hereinafter, referred to as "Compound (M-41)") with the compound (R-5). The reaction can be carried out according to a similar method to that described in WO 2008 / 051493.

[0179] A compound represented by formula (M-43) (hereinafter, referred to as "Compound (M-43)") can be prepared by reacting the compound (M-42) with lithium bis(trimethylsilyl)amide, and followed by reacting with bromine. The reaction can be carried out according to a similar method to that described in Journal of Organic Chemistry, (2008), 73(8), 3303.

[0180] The compound (A-21) can be prepared by using the compound (M-43) in place of the compound (M-2) according to a similar method to that for preparing the compound (A-1a) from the compound (M-2), said method being described in the Process 1.Process 17

[0181] A compound represented by formula (A-22) (hereinafter, referred to as "Compound (A-22)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0182] A compound represented by formula (M-45) (hereinafter, referred to as "Compound (M-45)") can be prepared by reacting a compound represented by formula (M-44) (hereinafter, referred to as "Compound (M-44)") with the compound (R-24). The reaction can be carried out according to a similar method to that described in US Publication No. 2016 / 0185785.

[0183] The compound (M-44) is a commercially available compound, or can be prepared by using the known method.

[0184] A compound represented by formula (M-46) (hereinafter, referred to as "Compound (M-46)") can be prepared by reacting the compound (M-45) with the compound (R-6). The reaction can be carried out according to a similar method to that described in WO 2014 / 160810.

[0185] A compound represented by formula (M-47) (hereinafter, referred to as "Compound (M-47)" can be prepared by reacting the compound (M-46) with phosphorus oxybromide. The reaction can be carried out according to a similar method to that described in WO 2002 / 030907.

[0186] A compound (A-22) can be prepared by using the compound (M-47) in place of the compound (M-5) according to a similar method to that for preparing the compound (A-3a) from the compound (M-5), said method being described in the Process 3.Process 18

[0187] A compound represented by formula (A-23) (hereinafter, referred to as "Compound (A-23)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0188] A compound represented by formula (M-49) (hereinafter, referred to as "Compound (M-49)") can be prepared by using a compound represented by formula (M-48) (hereinafter, referred to as "Compound (M-48)") in place of the Compound (A-19) according to a similar method to that for preparing the compound (A-20) from the compound (A-19), said method being described in the Process 14.

[0189] The compound (A-23) can be prepared by using the compound (M-49) in place of the compound (M-3) according to a similar method to that for preparing the compound (A-2a) from the compound (M-3), said method being described in the Process 2.Process 19

[0190] A compound represented by formula (A-24) (hereinafter, referred to as "Compound (A-24)") can be prepared according to the below-mentioned scheme. [wherein M represents a C1-C3 alkoxyboranyl group, a 4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl group, a tributylsutannyl group, ZnCl, MgCl, or MgBr, and the other symbols are the same as those defined above.]

[0191] A compound represented by formula (M-52) (hereinafter, referred to "Compound (M-52)") can be prepared by reacting the Compound (M-5) with the compound (M-8) in the presence of a catalyst.

[0192] The reaction can be usually carried out is a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixed solvents of two or more of these solvents.

[0193] Examples of the catalyst to be used in the reaction include palladium catalysts (such as tetrakis(triphenylphosphine) palladium (0), 1,1'-bis(diphenylphosphino)ferrocene palladium (II) dichloride, tris(dibenzylideneacetone) dipalladium (0), and palladium (II) acetate); nickel catalysts (such as bis(cyclooctadiene) nickel (0) and nickel(II) chloride); and copper catalysts (such as copper (I) iodide and copper (I) chloride).

[0194] A ligand, a base, and / or an alkali metal halide may be used in the reaction as needed.

[0195] Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybipheninyl, 1,2-bis (diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyqunoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (M-51).

[0196] Examples of the base include alkali metal hydrides, alkali metal carbonates, and organic bases. When the base is used in the reaction, the base is usually used within a range of 0.1 to 4 molar ratios as opposed to 1 mole of the compound (M-51).

[0197] Examples of the alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, and sodium chloride. When the alkali metal halide is used in the reaction, the alkali metal halide is usualy used within a range of 0.1 to 5 molar ratios as opposed to 1 mole of the compound (M-51).

[0198] In the reaction, the compound (M-8) is usually used within a range of 1 to 10 molar ratio(s), and the catalyst is usually used within a range of 0.01 to 0.5 molar ratios as opposed to 1 mole of the compound (M-51).

[0199] The reaction temperature in the reaction is usually within a range of -20 to 200°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0200] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (M-52).

[0201] The compound (A-24) can be prepared by reacting the compound (M-52) in place of the compound (M-2) according to a similar method to that for preparing the compound (A-1a) from the Compound (M-2), said method being described in the Process 1.Process 20

[0202] A compound represented by formula (A-25) (hereinafter, referred to as "Compound (A-25)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0203] A compound represented by formula (M-54) (hereinafter, referred to as "Compound (M-54)") can be prepared by reacting a compound represented by formula (M-53) (hereinafter, referred to as "Compound (M-53)" with a compound represented by formula (M-55) (hereinafter, referred to as "Compound (M-55)") in the presence of a catalyst. The reaction can be carried out by using the compound (M-53) in place of the compound (M-51) and the compound (M-55) in place of the compound (M-8) according to a similar method to that for preparing the compound (M-52) from the compound (M-51).

[0204] The compound (M-53) is a commercially available compound, or can be prepared according to the method described in or Journal of Organic Chemistry, (2015), 80 (4), 2413.

[0205] The compound (M-55) is a commercially available compound, or can be prepared according to a similar method to those described in Angewandte Chemie, International Edition, 2018, 57 (4), 1108, European Journal of Inorganic Chemistry, 2017, (34), 4020, WO 2017 / 17902, or Chemical Science, 2017, 8 (11), 7492.

[0206] The compound (A-25) can be prepared by using the compound (M-54) in place of the compound (M-3) according to a similar method to that for preparing the compound (A-2a) from the Compound (M-3), said method being described in the Process 2.Process 21

[0207] A compound represented by formula (A-26) (hereinafter, referred to as "Compound (A-26)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above.]

[0208] A compound represented by formula (M-56) (hereinafter, referred to as "Compound (M-56)") can be prepared by reacting the compound (M-8) with acetonitrile in the presence of a base. The reaction can be carried out according to a similar method to that described in Synlett, 2000, (10), 1488.

[0209] A compound represented by formula (M-57) (hereinafter, referred to as "Compound (M-57)") can be prepared by reacting the compound (M-56) with a compound presented by formula (R11) (hereinafter, referred to as "Compound (R11)") in the presence of a base. The reaction can be carried out according to a similar method to that described in Journal of the American Chemical Society (2011), 133, (37), 14785.

[0210] The compound (R11) is a commercially available compound, or can be prepared by using the known method.

[0211] A compound represented by formula (M-58) (hereinafter, referred to as "Compound (M-58)") can be prepared by reacting the Compound (M-57) with hydroxylamine in the presence of a base. The reaction can be carried out according to a similar method to that described in Bioorganic & Medicinal Chemistry (2017), 25, (6), 1914.

[0212] A compound represented by formula (M-59) (hereinafter, referred to as "Compound (M-59)") can be prepared by reacting the compound (M-58), tetrabutylammonium nitrite and trimethylsilyl chloride. The reaction can be carried out according to a similar method to that described in WO 2008 / 017361.

[0213] The compound (A-26) can be prepared by using the compound (M-59) in place of the compound (M-5) according to a similar method to that for preparing the compound (A-3a) from the compound (A-5), said method being described in the Process 3.Process 22

[0214] A compound represented by formula (A-27) (hereinafter, referred to as "Compound (A-27)") can be prepared according the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0215] A compound represented by formula (M-60) (hereinafter, referred to as "Compound (M-60)") can be prepared by reacting the compound (M-8) with propyne in the presence of a catalyst. The reaction can be carried out according to a similar method to that described in Journal of Medicinal Chemistry, 2014, 57 (17), 7412.

[0216] A compound represented by formula (M-61) (hereinafter, referred to as "Compound (M-61)") can be prepared by reacting the compound (M-60) with butyl lithium. The reaction can be carried out according to the method described in Journal of Organic Chemistry, 1990, 55(2), 695.

[0217] A compound represented by formula (M-62) (hereinafter, referred to as "Compound (M-62)") can be prepared by reacting the compound (M-61) with a compound represented by formula (R-12) (hereinafter, referred to as "Compound (R-12)") in the presence of a butyl lithium, followed by reacting with a compound represented by formula (R13) (hereinafter, referred to as "Compound (R13)"). The reaction can be carried out according to a similar method to that described in Tetrahedron Letters, 2004, 45, (30), 5881.

[0218] The compound (R-12) and the compound (R-13) are commercially available compounds, or can be prepared by using a known method.

[0219] The compound (A-27) can be prepared by reacting the compound (M-62) with a catalyst (such as copper bromide). The reaction can be carried out according to a similar method to that described in Russian Journal of Organic Chemistry, 2010, 46, (7), 1038.Process 23

[0220] A compound represented by formula (A-28) (hereinafter, referred to as "Compound (A-28)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0221] A compound represented by formula (A-63) (hereinafter, referred to as "Compound (A-63)") can be prepared by reacting the compound (M-41) with a compound represented by formula (R14) (hereinafter, referred to as "Compound (R14)"). The reaction can be carried out according to a similar method to that described in WO 2009 / 152025.

[0222] The compound (R14) is a commercially available compound, or can be prepared by using a known method.

[0223] A compound represented by formula (M-64) (hereinafter, referred to as "Compound (M-64)") can be prepared by reacting the compound (M-63) with formamide in the presence of a base. The reaction can be carried out according to a similar method to that described in WO 2009 / 152025.

[0224] A compound represented by formula (M-65) (hereinafter, referred to as "Compound (M-65)" can be prepared by reacting the compound (M-64) with N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide. The reaction can be carried out according to a similar method to that described in ACS Medicinal Chemistry Letters, 2013, 4 (6), 509.

[0225] The compound (A-28) can be prepared by using the compound (M-65) in place of the compound (M-5) according to a similar method to that for preparing the compound (A-3a) from the compound (M-5), said method being described in the Process 3.

[0226] Hereinafter, a process for preparing a production intermediate compound is described.Reference Process 1

[0227] The compound (M-4) can be prepared by reacting the compound (M-16) with a brominating agent. [wherein the symbols are the same as those defined above]

[0228] The reaction can be conducted according to a similar method to that described in WO 2013 / 191113.Reference Process 2

[0229] The compound (M-14) and the compound (M-41) can be prepared according to the below-mentioned scheme. [wherein Ra represents a methyl group or an ethyl group, and the other symbols are the same as defied above]

[0230] The compound (M-14) can be prepared by hydrolyzing a compound represented by formula (M-12) (hereinafter, referred to as "Compound (M-12)"), followed by reacting with N,O-dimethyl hydroxyl amine. These reactions can be conducted according to a similar method to that described in Journal of Medicinal Chemistry, 56, 3980 (2013).

[0231] A compound represented by formula (M-15) (hereinafter, referred to as "Compound (M-15)") can be prepared by reacting the compound represented by formula (M-14) with methyl magnesium chloride. The reaction can be carried out according to a similar method to that described in WO 2008 / 116665.

[0232] The compound (M-41) can be prepared by reacting the compound (M-15) with a brominating agent. The reaction can be prepared according to a similar method to that described in WO 2013 / 191113.Reference Process 3

[0233] A compound represented by formula (M-12a) (hereinafter, referred to as "Compound (M-12a)") can be prepared by reacting a compound represented by formula (M-18a) (hereinafter, referred to as "Compound (M-12a)") with a compound represented by formula (R15) (hereinafter, referred to as "Compound (R15)" in the presence of a base. [wherein X a< represents a fluorine atom or a chlorine atom, T 2< represents OR 1< , NR 1< R 29< , a group represented by formula T-5, a group represented by formula T-6, a group represented by formula T-7 or a group represented by formula T-8, and the other symbols are the same as those defined above]

[0234] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0235] Examples of the base to be used in the reaction include alkali metal carbonates, and alkali metal hydrides.

[0236] In the reaction, the compound (R15) is usualy used within a range of 1 to 2 molar ratio (s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-18a).

[0237] The reaction temperature in the reaction is usually within a range of -20 to 150°C. The reaction period in the reaction is usually within a range of 0.5 to 24 hours.

[0238] When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with an organic solvent, and the organic layers are worked up (for example, drying and concentration) to obtain the compound (M-12a).

[0239] The compound (R15) and the compound (M-18a) are commercially available compounds, or can be prepared by using a known method.Reference Process 4

[0240] A compound represented by formula (M-12b) can be prepared by reacting a compound represented by formula (M-18b) (hereinafter, referred to as "Compound (M-18b)") with a compound represented by formula (R16) (hereinafter, referred to as "Compound (R16)"). [wherein T 3< represents a group represented by the above-mentioned formula T-1, a group represented by the above-mentioned formula T-2, a group represented by the above-mentioned formula T-3, a group represented by the above-mentioned formula T-4, a group represented by the above-mentioned formula T-9, a group represented by the above-mentioned formula T-10, a group represented by the above-mentioned formula T-11 or a group represented by the above-mentioned formula T-12, and the other symbols are the same as those defined above]

[0241] The reaction can be conducted according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0242] The compound (R16) and the compound (M-18b) are commercially available compounds, or can be prepared by using a known method.Reference Process 5

[0243] The compound represented by formula (M-12c) can be prepared by reacting a compound represented by formula (M-18c) (hereinafter, referred to as "Compound (M-18c)") with a compound represented by formula (R17) (hereinafter, referred to as "Compound (R17)"). [wherein the symbols are the same as those defined above]

[0244] The reaction can be conducted according to a similar method to that described in WO 2016 / 121969.

[0245] The compound (R17) and the compound (M-18c) are commercially available compounds, or can be prepared according to known method.Reference Process 6

[0246] A compound represented by formula (M-12d) (hereinafter, referred to as "Compound (M-12d)") can be prepared by reacting the compound (M-18b) with a compound represented by formula (R18) (hereinafter, referred to as "Compound (R18)") in the presence of a copper. [wherein T 4< represents a C1-C10 chain hydrocarbon group which have one or more halogen atoms, a (C1-C5 alkoxy)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfanyl)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfinyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C1-C5 alkylsulfonyl group)C2-C5 alkyl group which have one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C3 alkyl group which may optionally have one or more substituents selected from Group G, or a C3-C7 cycloalkyl group which may optionally have one or more substituents selected from Group G, and the other symbols are the same as those defined above]

[0247] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0248] In the reaction, the compound (R18) is usually used within a range of 1 to 18 molar ratio(s), and the copper is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-18b).

[0249] The reaction temperature in the reaction is usually within a range of 40 to 200°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0250] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12d).

[0251] The compound (R18) is a commercially available compound, or can be prepared by using a known method.Reference Process 7

[0252] A compound represented by formula (M-12e) (hereinafter, referred to as "Compound (M-12e)") can be prepared by reacting a compound represented by formula (M-18d) (hereinafter, referred to as "Compound (M-18d)") with a compound represented by formula (R19) (hereinafter, referred to as "Compound (R19)") [wherein the symbols are the same as those defined above]

[0253] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0254] A base may be used in the reaction as needed, and examples of the base include organic bases. When the base is used in the reaction, the base is used within a range of 0.1 to 10 molar ratios(s) as opposed to 1 mole of the compound (M-18d).

[0255] In the reaction, the compound (R19) is usually carried out within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-18d).

[0256] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction include 0.1 to 24 hours.

[0257] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12e).

[0258] The compound (M-18d) and the compound (R19) are commercially available compounds, or can be prepared by using a known method.Reference Process 8

[0259] A compound represented by formula (M-12f) (hereinafter referred to as "Compound (M-12f)") can be prepared by the compound (M-18b) with a compound represented by formula (R-20) (hereinafter, referred to as "Compound (R-20)") in the presence of a base. (wherein R 40< represents an ethoxy group, an ethoxy group, a phenoxy group, N(CH 3 )OCH 3 , and the other symbols are the same as those defined above]

[0260] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, and aromatic hydrocarbons.

[0261] Examples of the bases to be used in the reaction include butyl lithium, lithium diisopropylamide, lithium tetramethylpiperidide, lithium bis(trimethylsilyl)amide and the others.

[0262] In the reaction, the compound (R-20) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1.0 to 2.0 molar ratio(s), as opposed to 1 mole of the compound (M-18b).

[0263] The reaction temperature in the reaction is usually within a range of -100 to 60°C. The reaction period in the reaction include 0.1 to 24 hours.

[0264] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12f).

[0265] The compound (R-20) is a commercially available compound, or can be prepared by using a known method.Reference Process 9

[0266] A compound represented by formula (M-12g) (hereinafter, referred to as "Compound (M-12g)") can be prepared by reacting a compound represented by formula (M-18e) (hereinafter, referred to as "Compound (M-18e)") with a compound represented by formula (R21) (hereinafter, referred to as "Compound (R21)") in the presence of a condensing agent. [wherein the symbols are the same as those defined above]

[0267] The reaction is usually carried out is a solvent. Examples of the solvents to be used in the reaction include ethers, aliphatic halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0268] Examples of the condensing agents to be used in the reaction include 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride salt.

[0269] A base may be used in the reaction as needed. Examples of the base include organic bases. When the base is used in the reaction, the base is usually used within a range of 0.1 to 10 molar ratios as opposed to 1 mole of the compound (M-18e).

[0270] In the reaction, the compound (R21) is usualy used within a range of 1 to 10 molar ratio(s), and the condensing agent is usually used within a range of 1 to 5 molar ratio(s), as opposed to 1 mole of the compound (M-18e).

[0271] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction include 0.1 to 24 hours.

[0272] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12g).

[0273] The compound (R-21) and the compound (M-18e) are commercially available compounds, or can be prepared by using a known method.Reference Process 10

[0274] A compound represented by formula (M-12h) (hereinafter, referred to as "Compound (M-12h)") can be prepared by reacting a compound represented by formula (M-18f) (hereinafter, referred to as "Compound (M-18f)") with a compound represented by formula (R-22) (hereinafter, referred to as "Compound (R22)"). [wherein the symbols are the same as those defined above]

[0275] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aliphatic halogenated hydrocarbons, aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0276] An acid may be used in the reaction as needed, and examples of the acid include p-toluenesulfonic acid, and camphor sulfonic acid, and the others. When the acid is used in the reaction, the acid is usually used within a range of 0.1 to 10 molar ratios, as opposed to 1 mole of the compound (M-18f).

[0277] In the reaction, the compound (R22) is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (M-18f).

[0278] The reaction temperature in the reaction is usually within a range of -20 to 180°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0279] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12h).

[0280] The compound (R22) and the compound (M-18f) are commercially available compounds, or can be prepared by using a known method.Reference Process 11

[0281] A compound represented by formula (M-12i) (hereinafter, referred to as "Compound (M-12i)") can be prepared by reacting a compound represented by formula (M-18g) (hereinafter, referred to as "Compound (M-18g)") with a compound represented by formula (R23) (hereinafter, referred to as "Compound (R23)") in the presence of a base. [wherein the symbols are the same as those defined above]

[0282] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixed solvents of two or more of these solvents.

[0283] Examples of the base to be used in the reaction include organic bases, alkali metal hydrides, and alkali metal carbonates.

[0284] In the reaction, the compound (R23) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 0.1 to 5 molar ratios, as opposed to 1 mole of the compound (M-18g).

[0285] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0286] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-12i).

[0287] The compound (R23) and the compound (M-18g) are commercially available compounds, or can be prepared by using a known method.Reference Process 12

[0288] A compound represented by formula (M-12j) (hereinafter, referred to as "Compound (M-12j)"), a compound represented by formula (M-12j-1) (hereinafter, referred to as "Compound (M-12j-1)"), and a compound represented by formula (M-12j-2) (hereinafter, referred to as "Compound (M-12j-2)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0289] A compound represented by formula (M-20) (hereinafter, referred to as "Compound (M-20)") can be prepared by reacting the compound (M-18b) with thiobenzoic acid in the presence of a copper catalyst and a base.

[0290] The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, water and mixed solvents of two or more of these solvents.

[0291] Examples of the copper catalysts to be used in the reaction include copper chloride, copper bromide, and copper iodide.

[0292] Examples of the bases to be used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0293] A ligand may be used in the reaction as needed. Examples of the ligand include 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyqunoline, and 1,10-phenanthroline and the others.

[0294] When a ligand is used in the reaction, the ligand is used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (M-18b).

[0295] In the reaction, thiobenzoic acid is usually used within a range of 1 to 10 molar ratio(s), the copper catalyst is usually used within a range of 0.01 to 0.5 molar ratios, and the base is usually used within a range of 0.1 to 5 molar ratios, as opposed to 1 mole of the compound (M-18b).

[0296] The reaction temperature in the reaction is usually within a range of -20 to 120°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0297] When the reaction is completed, water is added to the reaction mixture, and the reaction mixture is extracted with an organic solvent, and the organic layer is worked up (for example, drying and concentration) to obtain the compound (M-20).

[0298] A compound represented by formula (M-21) (hereinafter, referred to as "Compound (M-21)") can be prepared by hydrolyzing the compound (M-20). The reaction can be carried out according to a similar method to those described in WO 2011 / 068171, or Journal of Organic Chemistry, 1978, 43 (6), 1190-1192.

[0299] The compound (M-12j) can be prepared by using the compound (M-21) in place of the compound (M-18g) according to the method described in the Reference Process 11.

[0300] The compound (M-12-1) can be prepared by using the compound (M-12j) in place of the compound (A-1a) according to a similar method to that for preparing the compound (A-1b) from the compound (A-1a), said method being described in the Process 1.

[0301] The compound (M-12j-2) can be prepared by using the compound (M-12j-1) in place of the compound (A-1b) according to a similar method to that for preparing the compound (A-1c) from the compound (A-1b), said method being described in the Process 1.Reference Process 13

[0302] A compound represented by formula (M-8a) (hereinafter, referred to as "Compound (M-8a)") can be prepared by reacting a compound represented by formula (M-19a) (hereinafter, referred to as "Compound (M-19a)") with the compound (R15). [wherein the symbols are the same as those defined above]

[0303] The reaction can be carried out according to the Reference Process 3.

[0304] The compound (M-19a) is a commercially available compound, or can be prepared by using a known method.Reference Process 14

[0305] A compound represented by formula (M-8b) can be prepared by reacting a compound represented by formula (M-19b) (hereinafter, referred to as "Compound (M-19b)") with the compound (R16). [wherein the symbols are the same as those defined above]

[0306] The reaction can be carried out according to the Reference Process 4.

[0307] The compound (M-19b) is a commercially available compound, or prepared by using a known method.Reference Process 15

[0308] A compound represented by formula (M-8c) (hereinafter, referred to as "Compound (M-8c)") can be prepared by reacting a compound represented by formula (M-19c) (hereinafter, referred to as "Compound (M-19c)") with the compound (R17). [wherein the symbols are the same as those defined above]

[0309] The reaction can be carried out according to the Reference Process 5.

[0310] The compound (M-19c) is a commercially available compound, or can be prepared by using a known method.Reference Process 16

[0311] A compound represented by formula (M-8d) (hereinafter, referred to as "Compound (M-8d)") can be prepared by reacting the compound (M-19b) with the compound (R18). [wherein the symbols are the same as those defined above]

[0312] The reaction can be carried out according to the Reference Process 6.Reference Process 17

[0313] A compound represented by formula (M-8e) (hereinafter, referred to as "Compound (M-8e)") can be prepared by reacting a compound represented by formula (M-19d) (hereinafter, referred to as "Compound (M-19d)") with the compound (R19). [wherein the symbols are the same as those defined above]

[0314] The reaction can be carried out according to the Reference Process 7.

[0315] The compound (M-19d) is a commercially available compound, or can be prepared by using a known method.Reference Process 18

[0316] A compound represented by formula (M-8f) (hereinafter, referred to as "Compound (M-8f)") can be prepared by reacting the compound (M-19b) with the compound (R-20). [wherein the symbols are the same as those defined above]

[0317] The reaction can be carried out according to the Reference Process 8.Reference Process 19

[0318] A compound represented by formula (M-8g) (hereinafter, referred to as "Compound (M-8g)") can be prepared by reacting a compound represented by formula (M-19e) (hereinafter, referred to as "Compound (M-19e)") with the compound (R21). [wherein the symbols are the same as those defined above]

[0319] The reaction can be carried out according to the Reference Process 9.

[0320] The compound (M-19e) is a commercially available compound, or can be prepared by using a known method.Reference Process 20

[0321] A compound represented by formula (M-8h) (hereinafter, referred to as "Compound (M-8h)") can be prepared by reacting a compound represented by formula (M-19f) (hereinafter, referred to as "Compound (M-19f)") with the compound (R22). [wherein the symbols are the same as those defined above]

[0322] The reaction can be carried out according to the Reference Process 10.

[0323] The compound (M-19f) is a commercially available compound, or can be prepared by using a known method.Reference Process 21

[0324] A compound represented by formula (M-8i) (hereinafter, referred to as "Compound (M-8i)") can be prepared by reacting a compound represented by formula (M-19g) (hereinafter, referred to as "Compound (M-19g)") with the compound (R23). [wherein the symbols are the same as those defined above]

[0325] The reaction can be carried out according to the Reference process 11.

[0326] The compound (M-19g) is a commercially available compound, or can be prepared by a known method.Reference Process 22

[0327] A compound represented by formula (M-8j) (hereinafter, referred to as "Compound (M-8j)"), a compound represented by formula (M-8j-1) (hereinafter, referred to as "Compound (M-8j-1)"), and a compound represented by formula (M-8j-2) (hereinafter, referred to as "Compound (M-8j-2)") can be prepared according to the below-mentioned scheme. [wherein the symbols are the same as those defined above]

[0328] These reactions can be carried out according to the Reference Process 12.Reference Process 23

[0329] The compound (M-2) can be prepared by reacting the compound (M-8) with a compound represented by formula (M-66) (hereinafter, referred to as "Compound (M-66)") in the presence of a catalyst. [wherein the symbols are the same as those defined above]

[0330] The reaction can be carried out by using the compound (M-66) in place of the compound (M-51) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0331] The compound (M-66) is a commercially available compound, or can be prepared according to a similar method to that described in WO 2016 / 168914.Reference Process 24

[0332] The compound (M-3) can be prepared by reacting the compound (M-8) with a compound represented by formula (M-67) (hereinafter, referred to as "Compound (M-67)") in the presence of a catalyst. [wherein the symbols are the same as those defined above]

[0333] The reaction can be carried out by using the compound (M-67) in place of the compound (M-51) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0334] The compound (M-67) is a commercially available compound, or can be prepared according to a similar method to that described in WO 2013 / 052394.Reference Process 25

[0335] The compound (M-5) can be prepared by reacting the compound (M-8) with a compound represented by formula (M-68) (hereinafter, referred to as "Compound (M-68)") in the presence of a catalyst. [wherein the symbols are the same as those defined above]

[0336] The reaction can be carried out by using the compound (M-68) in place of the compound (M-51) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0337] The compound (M-68) is a commercially available compound, or can be prepared according to a similar method to that described in Chemistry - A European Journal, 2015, 21 (25), 9236.Reference Process 26

[0338] The compound (M-2) can be prepared by reacting the compound (M-55) with a compound represented by formula (M-69) (hereinafter, referred to as "Compound (M-69)") in the presence of a catalyst. [wherein X c< represents a bromine atom or an iodine atom, and the other symbols are the same as those defined above]

[0339] The reaction can be carried out by using the compound (M-55) in place of the compound (M-51) and using the compound (M-69) in place of the compound (M-8) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0340] The compound (M-69) is a commercially available compound, or can be prepared by using a known method.Reference Process 27

[0341] The compound (M-3) can be prepared by reacting the compound (M-55) with a compound represented by formula (M-70) (hereinafter, referred to as "Compound (M-70)") in the presence of a catalyst. [wherein the symbols are the same as those defined above]

[0342] The reaction can be carried out by using the compound (M-55) in place of the compound (M-51) and using the compound (M-70) in place of the compound (M-8) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0343] The compound (M-70) is a commercially available compound, or can be prepared according to a similar method to those described in Journal of Medicinal Chemistry, 2015, 58 (17), 6766, WO 2009 / 123695, Journal of Organic Chemistry, 1981, 46 (11), 2221, JP 2011-098956 A, Synlett, 2010, (19), 2875, Journal of Organic Chemistry, 2015, 80 (4), 2413.Reference Process 28

[0344] The compound (M-5) can be prepared by reacting the compound (M-55) with a compound represented by formula (M-71) (hereinafter, referred to as "Compound (M-71)") in the presence of a catalyst. [wherein the symbols are the same as those defined above]

[0345] The reaction can be carried out by using the compound (M-55) in place of the compound (M-51) and using the compound (M-71) in place of the compound (M-8) according to a similar method to that for preparing the compound (M-52) from the compound (M-51), said method being described in the Process 19.

[0346] The compound (M-71) is a commercially available compound, or can be prepared according to a similar method to those described in Angewandte Chemie, International Edition, 2018, 57 (4), 1039, European Journal of Inorganic Chemistry, 2017, (33), 3878, WO 2017 / 100819, WO 2017 / 087837, Journal of Agricultural and Food Chemistry, 2017, 65 (26), 5397, WO 2017 / 027312, or Journal of Organic Chemistry, 82 (11), 2017, 5947 and so on.Reference Process 29

[0347] A compound represented by formula (M-51Z) (hereinafter, referred to as "Compound (M-51Z)") can be prepared by reacting the compound (M-50) with a compound represented by formula (R9) (hereinafter, referred to as "Compound (R9)") in the presence of a base. [wherein M z< represents a tributylstannyl group, ZnCl, MgCl, or MgBr, X x< represents a halogen atom, and the other symbols are the same as those defined above]

[0348] The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include ethers, aromatic hydrocarbons, and mixed solvents of two or more of these solvents.

[0349] Examples of the base to be used in the reaction include lithium diisopropylamide, lithium bis(triethylsilyl)amide, and potassium bis(trimethylsilyl)amide.

[0350] Examples of the compound (R9) include zinc chloride, magnesium bromide, tributyl stannyl chloride.

[0351] In the reaction, the compound (R9) is usually used within a range of 1 to 2 molar ratio (s), and the base is usually used within a range of 1 to 2 molar ratio(s), as opposed to 1 mole of the compound (M-50).

[0352] The reaction temperature in the reaction is usually within a range of -100 to 0°C. The reaction period in the reaction is usually within a range of 0.1 to 24 hours.

[0353] When the reaction is completed, water is added to reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers re worked up (for example, drying and concentration) to obtain the compound (M-51Z). After the completion of the reaction, a mixture containing the compound (M-51A) may be used as itself to a next reaction.

[0354] The compound (R9) is a commercially available compound, or can be prepared by using a known method.

[0355] The compound (M-50) is a commercially available compound, or can be prepared by using a known method.Reference Process 30

[0356] A compound represented by formula (M-51B) (hereinafter, referred to as "Compound (M-51B)") can be prepared by reacting the compound (M-50) with a compound represented by formula (R10) (hereinafter, referred to as "Compound (R10)") in the presence of a base. represents a C1-C3 alkoxy group, and the other symbols are the same as those defined above]

[0357] The reaction can be carried out by using the compound (R10) in place of the compound (R9) according to the Reference process 29.

[0358] The compound (R10) is a commercially available compound, or can be prepared by using a known method.

[0359] The compound can be mixed or combined with one or more ingredients selected from the group consisting of the following Group (a), Group (b), Group (c), Group (d), Group (e), Group (f), Group (g), and Group (h) (hereinafter, referred to as "present ingredient").

[0360] The mixing or combining represents that the compound and the present ingredient are used concurrently, separately, or at an interval.

[0361] When the compound and the present ingredient are concurrently used, the compound and the present ingredient may be incorporated as a separate formulation or one formulation.

[0362] One aspect described herein relates to a composition comprising one or more ingredients selected from the group consisting of the Group (a) and the Group (b), and the compound (hereinafter, referred to as "Composition A"). An aspect of the present invention relates to a composition comprising one or more ingredients selected from Group (a) and Group (b), and an inventive compound, as defined in the claims.

[0363] The Group (a) represents insecticidal ingredients, miticidal ingredients and nematicidal ingredients that are a group consisting of acetylcholinesterase inhibitors (for example, carbamate insecticides and organophosphate insecticides), GABA-gated chloride ion channel antagonists (for example, phenylpyrazole insecticides), sodium channel modulators (for example, pyrethroid insecticides), nicotinic acetylcholine receptor antagonist modulators (for example, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators (for example, macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mites growth regulators, mitochondrial ATP synthase inhibitors, uncouplers of oxidative phosphorylation, nicotinic acetylcholine receptor channel blockers (for example, nereistoxin insecticides), inhibitors of chitin biosynthesis, moulting disruptors, ecdysone receptor agonists, octopamine receptor agonists, Inhibitors of mitochondrial electron transport chain complex I, II, III, and IV, voltage-dependent sodium channel blockers, Inhibitors of acetyl CoA carboxylase, ryanodine receptor modulators (for example, diamide insecticides), chordotonal organ modulators, each active ingredient of microbial fungicides, and other insecticidal ingredients, miticidal ingredients and nematicidal ingredients. These agents are described in the classification based on the IRAC mode of action.

[0364] The Group (b) represents fungicidal ingredients that are a group consisting of nucleic acid synthesis inhibitors (for example, phenylamide fungicides and acylamino acid fungicides), cytostatic and cytoskeletal inhibitors (for example, MBC fungicides), respiration inhibitors (for example, QoI fungicides and QiI fungicides), amino-acid synthesis and protein synthesis inhibitors (for example, anilinopyridine fungicides), signal-transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (for example, DMI fungicides such as triazoles), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducer, multisite fungicides, microbial fungicides, and other fungicidal ingredients. These agents are described in the classification based on the FRAC mode of action.

[0365] The Group (c) represents a group of plant growth modulating ingredients including mycorrhizal fungus and rhizobia.

[0366] The Group (d) represents a group of phytotoxicity mitigation ingredients.

[0367] The Group (e) represents a group of synergists.

[0368] The Group (f) represents a group of repellent ingredients consisting of bird repellent ingredients, insect repellent ingredients, and animal repellent ingredients.

[0369] The Group (g) represents a group of molluscicide ingredients.

[0370] The Group (h) represents a group of insect pheromones.

[0371] Examples of combinations of the present ingredient and the compound are recited as follows. For example, the "alanycarb + SX" indicates a combination of alanycarb and SX.

[0372] The abbreviation "SX" means any one of the compounds selected from the compound classes SX(number) described in the following. Further, any of the present ingredients as described below are a known ingredient, and can be obtained as a commercially available drug or prepared according to a known method. When the present ingredient represents a microorganism, the present ingredient can be obtained from a microorganism depositary authority. The number in parentheses represents CAS RN (registered trademark).

[0373] A combination of the present ingredient in the above-mentioned Group (a) and the compound: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + 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, Celastrus angulatus (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 phosphide + 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, concanamycin A + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cycloniliprole + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + 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, dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of Dryopteris filix-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 Cassia nigricans + SX, extract of clitoria ternatea + SX, extract of Symphytum officinale + SX, extracts or simulated blend 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, fenbutatin oxide + SX, fenitrothion + 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, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupyradifurone + SX, flupyrimin + 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 of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imiprothrin + SX, indoxacarb + 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, lepimectin + SX, lime sulfur + 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, milbemycin oxime + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, neem oil + 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, potassium cyanide + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + 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, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spinetoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of chenopodium ambrosioides near ambrosioides (Brand name: Terpenoid blend QRD 460) + 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, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, vamidothion + SX, wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropanesulfinyl)propanamide (1477923-37-7) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietane-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}indan-1-yl)propanamide (1118626-57-5) + SX, N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluropropan-2-yl)phenyl]-3-{ethyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1429513-53-0) + SX, N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-(ethyl(4-cyanobenzoyl)amino]-2-methoxybenzamide (1609007-65-9) + SX, N-[2-bromo-6-difluoromethoxy-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-{methyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1630969-78-6) + SX, 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine (885026-50-6) + SX, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein CrylFa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX, BT crop protein Cry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulosis virus BV-0001 + SX, Anticarsia gemmatalis mNPV + SX, Autographa californica mNPV + SX, Cydia pomonella GV V15 + SX, Cydia pomonella GV V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera NPV BV-0003 + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + 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 GB-126 + SX, Bacillus firmus I-1582 + SX, Bacillus megaterium + SX, Bacillus sp.AQ175 + SX, Bacillus sp.AQ177 + SX, Bacillus sp.AQ178 + SX, Bacillus sphaericus 2362 + SX, Bacillus sphaericus ABTS1743 + SX, Bacillus sphaericus Serotype H5a5b + SX, Bacillus thuringiensis AQ52 + SX, Bacillus thuringiensis BD#32 + SX, Bacillus thuringiensis CR-371 + SX, Bacillus thuringiensis subsp. Aizawai ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai GC-91 + SX, Bacillus thuringiensis subsp. Aizawai Serotype H-7 + SX, Bacillus thuringiensis subsp. Kurstaki ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki EG234 + SX, Bacillus thuringiensis subsp. Kurstaki EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki F810 + SX, Bacillus thuringiensis subsp. Kurstaki HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki PB54 + SX, Bacillus thuringiensis subsp. Kurstaki SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis MPPL002 + SX, Bacillus thuringiensis subsp.morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis BMP144 + SX, Bacillus thuringiensis var. israelensis serotype H-14 + SX, Bacillus thuringiensis var. japonensis buibui + SX, Bacillus thuringiensis var. san diego M-7 + SX, Bacillus thuringiensis var.7216 + SX, Bacillus thuringiensis var.aegypti + SX, Bacillus thuringiensis var.T36 + SX, Beauveria bassiana ANT-03 + SX, Beauveria bassiana ATCC74040 + SX, Beauveria bassiana GHA + SX, Beauveria brongniartii + SX, Burkholderia rinojensis A396 + SX, Chromobacterium subtsugae PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis) + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Metarhizium anisopliae F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka97 + SX, Paecilomyces lilacinus 251 + SX, Paecilomyces tenuipes T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thoynei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani NCIM1312 + SX, lenoremycin + SX, concanamycin A + SX, acetoprole) + SX, lotilaner + SX, sarolaner + SX, isocycloseram + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Lecanicillium muscarium Ve6 + SX, N-ethyl-5-methyl-1-(3-methylbutan-2-yl)-N-(pyridazin-4-yl)-1H-pyrazole-4-carboxamide (1403615-77-9) + SX, and imidaclothiz + SX.

[0374] A combination of the present ingredient in the above-mentioned Group (b) and the compound: 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, benthivalicarb-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, chloroneb + SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + 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 from Melaleuca alternifolia + SX, extract from Reynoutria sachalinensis + SX, extract from the cotyledons of lupine plantlets ("BLAD") + SX, extract of Allium sativum + SX, extract of Equisetum arvense + SX, extract of Tropaeolum majus + SX, famoxadone + 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, fentin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, fludioxonil + SX, flufenoxystrobin + SX, fluindapyr + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxastrobin + 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, ipfentrifluconazole + 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, metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, mineral oils + 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, 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, 3-(difluorodifluoromethyl)-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide (1639015-48-7) + SX, 3-(difluorodifluoromethyl)-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide (1639015-49-8) + SX, 3-(difluorodifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (141573-94-6) + SX, 3-(difluorodifluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethylindan-4-yl]-1-methylpyrazole-4-carboxamide (1513466-73-3) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethaneimidamide (1202781-91-6) + SX, 2-{3-[2-(1-{[3,5-bis(difluorodifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-y1]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl=methanesulfonate (1360819-11-9) + SX, 4-(2-bromo4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, 5-fluoro-2-[(4-methylphenyl)methoxy]-4-pyrimidinamine (1174376-25-0) + SX, 5-fluoro-4-imino-3-methyl-1H-tosyl-3,4-dihydropyrimidin-2(1H)-one (1616664-98-2) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxyl-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine (1446247-98-8) + SX, α-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol (1229605-96-2) + SX, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol (1229606-46-5) + SX, (αR) - [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol (1229606-02-3) + SX, 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione (1342260~19-8) + SX, 2-{ [(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-70-7) + SX, 2-{[(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-71-8) + SX, 2-{[(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-72-9) + SX, 2-{[(2S,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-73-0) + SX, 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanato (1342260-26-7) + SX, 1-{[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1638897-82-1) + SX, 1-{[(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1638897-84-3) + SX, 1-{[(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl)methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1638897-86-5) + SX, 1-{ [(2S,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (1638897-89-8) + SX, 5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1394057-11-4) + SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801930-06-2) + SX, (1S,2R,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801930-07-3) + SX, (1R,2R,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-53-8) + SX, (1S,2S,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-54-9) + SX, (1R,2R,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-55-0) + SX, (1S,2S,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-56-1) + SX, (1R,2S,5R)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-57-2) + SX, (1S,2R,5S)-5-(4-chlorobenzyl)-2-chloromethyl-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801919-58-3) + SX, methyl=3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (1791398-02-1) + SX, methyl=(1R,2S,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-90-2) + SX, methyl=(1S,2R,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-91-3) + SX, methyl=(1R,2R, 3R}-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-92-4) + SX, methyl=(1S,2S,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-93-5) + SX, methyl=(1R,2R,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-94-6) + SX, methyl=(1S,2S,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2080743-95-7) + SX, methyl=(1R,2S,3R)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2081061-22-3) + SX, methyl=(1S,2R,3S)-3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (2081061-23-4) + SX, 2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1394057-13-6) + SX, (1R,2S,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801930-08-4) + SX, (1S,2R,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1801930-09-5) + SX, (1R,2R,5R}-2-chloromethyl-5-{4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-08-4) + SX, (1S,2S,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-10-8) + SX, (1R,2R,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-13-1) + SX, (1S,2S,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-16-4) + SX, (1R,2S,5R)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-20-0) + SX, (1S,2R,5S)-2-chloromethyl-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (1638898-24-4) + SX, (R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-in-2-ol (1801919-59-4) + SX, (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)pheny1]-1-(1,2,4-triazol-1-yl)propan-2-ol (1616236-94-2) + SX, (R)-1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol (1801919-60-7) + SX, (R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol (1801919-61-8) + SX, 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolin-3-yl]pyridine (847749-37-5) + SX, Agrobacterium radiobactor K1026 + SX, Agrobacterium radiobactor K84 + SX, Bacillus amyloliquefaciens AT332 + SX, Bacillus amyloliquefaciens B3 + SX, Bacillus amyloliquefaciens D747 + SX, Bacillus amyloliquefaciens DB101 + SX, Bacillus amyloliquefaciens DB102 + SX, Bacillus amyloliquefaciens GB03 + SX, Bacillus amyloliquefaciens FZB24 + SX, Bacillus amyloliquefaciens FZB42 + SX, Bacillus amyloliquefaciens IN937a + SX, Bacillus amyloliquefaciens MBI600 + SX, Bacillus amyloliquefaciens QST713 + SX, Bacillus amyloliquefaciens isolate B246 + SX, Bacillus amyloliquefaciens F727 + SX, Bacillus licheniformis HB-2 + SX, Bacillus licheniformis SB3086) + SX, Bacillus pumilus AQ717 + SX, Bacillus pumilus BUF-33 + SX, Bacillus pumilus GB34 + SX, Bacillus pumilus QST2808 + SX, Bacillus simplex CGF2856 + SX, Bacillus subtilis AQ153 + SX, Bacillus subtilis AQ743 + SX, Bacillus subtilis BU1814 + SX, Bacillus subtilis D747 + SX, Bacillus subtilis DB101 + SX, Bacillus subtilis FZB24 + SX, Bacillus subtilis GB03 + SX, Bacillus subtilis HAI0404 + SX, Bacillus subtilis IAB / BS03 + SX, Bacillus subtilis MBI600 + SX, Bacillus subtilis QST30002 / AQ30002 + SX, Bacillus subtilis QST30004 / AQ30004 + SX, Bacillus subtilis QST713 + SX, Bacillus subtilis QST714 + SX, Bacillus subtilis var. Amyloliquefaciens FZB24 + SX, Bacillus subtilis Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin J82 + SX, Burkholderia cepacia type Wisconsin M54 + SX, Candida oleophila O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans CGMCC8325 + SX, Coniothyrium minitans CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp.carotovora CGE234M403 + SX, Fusarium oxysporum Fo47 + SX, Gliocladium catenulatum J1446 + SX, Paenibacillus polymyxa AC-1 + SX, Paenibacillus polymyxa BS-0105 + SX, Pantoea agglomerans E325 + SX, Phlebiopsis gigantea VRA1992 + SX, Pseudomonas aureofaciens TX-1 + SX, Pseudomonas chlororaphis 63-28 + SX, Pseudomonas chlororaphis MA342 + SX, Pseudomonas fluorescens 1629RS + SX, Pseudomonas fluorescens A506 + SX, Pseudomonas fluorescens CL145A + SX, Pseudomonas fluorescens G7090 + SX, Pseudomonas sp. CAB-02 + SX, Pseudomonas syringae 742RS + SX, Pseudomonas syringae MA-4 + SX, Pseudozyma flocculosa PF-A22UL + SX, Pseudomonas rhodesiae HAI-0804 + SX, Pythium oligand Rum DV74 + SX, Streptomyces griseoviridis K61 + SX, Streptomyces lydicus WYCD108US + SX, Streptomyces lydicus WYEC108 + SX, Talaromyces flavus SAY-Y-94-01 + SX, Talaromyces flavus V117b + SX, Trichoderma asperellum ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum T34 + SX, Trichoderma atroviride CNCM 1-1237 + SX, Trichoderma atroviride LC52 + SX, Trichoderma atroviride SC1 + SX, Trichoderma atroviride SKT-1 + SX, Trichoderma gamsii ICC080 + SX, Trichoderma harzianum 21 + SX, Trichoderma harzianum DB104 + SX, Trichoderma harzianum DSM 14944 + SX, Trichoderma harzianum ESALQ-1303 + SX, Trichoderma harzianum ESALQ-1306 + SX, Trichoderma harzianum IIHR-Th-2 + SX, Trichoderma harzianum kd + SX, Trichoderma harzianum M01 + SX, Trichoderma harzianum SF + SX, Trichoderma harzianum T22 + SX, Trichoderma harzianum T39 + SX, Trichoderma harzianum TEM908 + SX, Trichoderma harzianum TH35 + SX, Trichoderma polysporum IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens G-41 + SX, Trichoderma virens GL-21 + SX, Trichoderma viride) + SX, Variovorax paradoxus CGF4526 + SX, Harpin protein + SX, Trichoderma harzianum ITEM908 + SX, Trichoderma harzianum T78 + 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, Bacillus amyloliquefaciens subsp. plantarum D747 + SX, Pythium oligandrum M1 + SX, Trichoderma asperellum T25 + SX, richoderma asperellum TV1 + SX, Trichoderma atroviride IMI 206040 + SX, Trichoderma atroviride T11 + SX, Bacillus amyloliquefaciens (Aveo(trademark) EZ Nematicide) + SX.

[0375] A combination of the present ingredient in the above-mentioned Group (c) and the compound: 1-methylcyclopropene + 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, 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, choline chloride + 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, Gibberellin A + SX, Gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione + SX, pacrobutrazol + SX, pendimethalin + SX, prohexandione-calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, streptmycin + 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]butylate + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]-1-propanol + SX, formononetin + SX, Claroideoglomus etunicatum + 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 RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX, Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + 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 tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, lipochitooligosaccharide SP104 + SX, Zucchini Yellow Mosaik Virus weak strain + SX ∘

[0376] A combination of the present ingredient in the above-mentioned Group (d) and the compound: allidochlor + SX, benoxacor + SX, cloquintocet + SX, cloquintocet-mexyl + SX, cyometrinil + SX, cyprosulfamide + SX, dichlormid + SX, dicyclonone + SX, dimepiperate + SX, disulfoton + SX, dymron + SX, fenchlorazole + SX, fenchlorazole-ethyl + SX, fenclorim + SX, flurazole + SX, furilazole + SX, fluxofenim + SX, Hexim + SX, isoxadifen + SX, isoxadifen-ethyl + SX, mecoprop + SX, mefenpyr + SX, mefenpyr-ethyl + SX, mefenpyr-diethyl + SX, mephenate + SX, metcamifen + SX, oxabetrinil + SX, 1,8-naphthalic anhydride + SX, 1,8-octamethylene diamine + SX, AD-67 (4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane) + SX, CL-304415 (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) + SX, CSB (1-bromo-4-[(chloromethyl)sulfonyl]benzene) + SX, DKA-24 (2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-(2-propenyl)acetamide) + SX, MG191 (2-(dichloromethyl)-2-methyl-1,3-dioxolane) + SX, MG-838 (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) + SX, PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide) + SX, R-28725 (3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine) + SX, R-29148 (3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine) + SX, TI-35 (1-(dichloroacetyl)azepane) + SX.

[0377] A combination of the present ingredient in the above-mentioned Group (e) and the compound: 1-dodecyl-1H-imidazole + SX, N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide + SX, bucarpolate + SX, N,N-dibutyl-4-chlorobenzenesulfonamide + SX, dietholate + SX, diethylmaleate + SX, piperonyl butoxide + SX, piperonyl cyclonene + SX, piprotal + SX, propyl isome + SX, safroxan + SX, sesamex + SX, sesamolin + SX, sulfoxide + SX, Verbutin + SX, DMC (1,1-bis(4-chlorophenyl)ethanol) + SX, FDMC (1,1-bis(4-chlorophenyl)-2,2,2-trifluoroethanol) + SX, ETN (1,2-epoxy-1,2,3,4-tetrahydronaphthalene) + SX, ETP (1,1,1-trichloro-2,3-expoxypropane) + SX, PSCP (phenylsaligenin cyclic phosphate) + SX, TBPT (S,S,S-tributyl phosphorotrithioate)SX, TPP (triphenyl phosphate) + SX.

[0378] A combination of the present ingredient in the above-mentioned Group (f) and the compound: anthraquinone + SX, chloralose + SX, acrep + SX, butopyronoxyl + SX, camphor + SX, d-camphor + SX, carboxide + SX, dibutyl phthalate + SX, deet + SX, dimethyl carbate + SX, dimethyl phthalate + SX, dibutyl succinate + SX, dibutyl adipate + SX, ethohexadiol + SX, hexamide + SX, icaridin + SX, methoquin-butyl + SX, methylneodecanamide + SX, 2-(octylthio)ethanol + SX, butoxypolypropylene glycol + SX, oxamate + SX, quwenzhi + SX, quyingding + SX, zengxiaon + SX, rcbemide + SX, copper naphthenate + SX, zinc naphthenate + SX.

[0379] A combination of the present ingredient in the above-mentioned Group (g) and the compound: bis(tributyltin) oxide + SX, allicin + SX, bromoacetamide + SX, cloethocarb + SX, copper sulfate + SX, fentin + SX, ferric phosphate + SX, metaldehyde + SX, niclosamide + SX, pentachlorophenol + SX, sodium pentachlorophenoxide + SX, tazimcarb + SX, tralopyril + SX, trifenmorph + SX.

[0380] A combination of the present ingredient in the above-mentioned Group (h) and the compound: (E)-2-hexenal + SX, (E)-2-octadecenal + SX, (E)-4-tridecen-1-yl acetate + SX, (E)-5-decen-1-yl acetate + SX, (E)-5-decen-1-ol + SX, (E)-3,3-dimethylcyclohexylideneacetaldehyde + SX, (E)-7-dodecen-1-yl acetate + SX, (E)-8-dodecen-1-yl acetate + SX, (E)-9-dodecen-1-yl acetate + SX, (E)-10-hexadecenal + SX, (E)-11-hexadecen-1-yl acetate + SX, (E)-11-tetradecen-1-yl acetate + SX, (E)-11-tetradecen-1-ol + SX, (E)-4-tridecen-1-yl acetate + SX, (E)-6-methylhept-2-en-4-ol + SX, (Z)-2-(3,3-dimethylcyclohexylidene)ethanol + SX, (Z)-4-decen-1-yl acetate + SX, (Z)-4-tridecen-1-yl acetate + SX, (Z)-5-decen-1-yl acetate + SX, (Z)-5-decen-1-ol + SX, (Z)-7-tetradecenal + SX, (Z)-7-dodecen-1-yl acetate + SX, (Z)-8-dodecen-1-yl acetate + SX, (Z)-9-dodecen-1-yl acetate + SX, (Z)-8-dodecen-1-ol + SX, (Z)-9-hexadecenal + SX, (Z)-10-hexadecen-1-yl acetate + SX, (Z)-11-hexadecen-1-ol + SX, (Z)-11-hexadecenal + SX, (Z)-11-hexadecen-1-yl acetate + SX, (Z)-11-octadecenal + SX, (Z)-13-octadecenal + SX, (Z)-hexadec-13-en-11-yn-1-yl acetate + SX, (Z)-13-octadecenal + SX, (Z)-icos-13-en-10-one + SX, (Z)-7-tetradecenal + SX, (Z)-tetradec-9-en-1-ol + SX, (Z)-9-tetradecen-1-yl acetate + SX, (Z)-11-tetradecen-1-yl acetate + SX, (Z)-13-icosen-10-one + SX, (Z,E)-7,11-hexadecadien-1-yl acetate + SX, (Z,E)-9,12-tetradecadien-1-yl acetate + SX, (E,Z)-4,10-tetradecadien-1-yl acetate + SX, (E,E)-8,10-dodecadien-1-ol + SX, (E,E)-10,12-hexadecadienal + SX, (E,E)-9,11-tetradecadien-1-yl acetate + SX, (E,Z)-2,13-octadecadien-1-ol + SX, (E,Z) -3,13-octadecadien-1-ol + SX, (E,Z)-2,13-octadecadien-1-yl acetate + SX, (E,Z)-3,13-octadecadien-1-yl acetate + SX, (E, Z) -7, 9-dodecadien-1-yl acetate + SX, (E,E)-7,9-dodecadien-1-yl acetate + SX, (Z,E)-9,12-tetradecadien-1-yl acetate + SX, (Z,E)-9,11-tetradecadien-1-yl acetate + SX, (Z,E)-7,11-hexadecadien-1-yl acetate + SX, (Z,Z)-3,13-octadecadien-1-ol + SX, (Z,Z)-4,7-decadien-1-yl acetate + SX, (Z,Z)-3,13-octadecadien-1-yl acetate + SX, (Z, Z)-7,11-hexadecadien-1-yl acetate + SX, (Z,Z,E)-7,11,13-hexadecatrienal + SX, (5R)-5-[(1Z)-1-decen-1-yl]dihydro-2(3H)-furanone + SX, (2R,5R)-ethyl-1,6-dioxaspiro[4,4]nonane + SX, (2R,5S)-ethyl-1,6-dioxaspiro[4,4]nonane + SX, (4R,8R)-4,8-dimethyldecanal + SX, (4R,8S)-4,8-dimethyldecanal + SX, 2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3,2,1]octane + SX, (-)-4-methyl-3-heptanol + SX, 1,7-dioxaspiro[5,5]undecane + SX, 3-carene + SX, 3-methylcyclohex-2-en-1-one + SX, 14-methyloctadec-1-ene + SX, 4-methylnonan-5-ol + SX, 4-methylnonan-5-one + SX, 4-(3-oxobutyl)phenyl acetate + SX, dodecyl acetate + SX, dodeca-8,10-dien-1-yl acetate + SX, ethyl (2E,4Z)-decadienoate + SX, ethyl 4-methyloctanoate + SX, methyl 2,6,10-trimethyldodecanoate + SX, tetradecan-1-ol + SX, tetradec-11-en-1-ol + SX, tetradec-11-en-1-yl acetate + SX, tridec-4-en-1-yl acetate + SX, (3S,6R)-3-methyl-6-isopropenyl-9-decen-1-yl acetate + SX, (3S,6S)-3-methyl-6-isopropenyl-9-decen-1-yl acetate + SX, alpha-multistriatin + SX, alpha-pinene + SX, endo-brevicomin + SX, exo-brevicomin + SX, camphene + SX, codlelure + SX, codlemone + SX, cuelure + SX, disparlure + SX, dominicalure + SX, eugenol + SX, farnesol + SX, ferrolure + SX, frontalin + SX, gossyplure + SX, grandlure + SX, grandlure I + SX, grandlure II + SX, grandlure III + SX, grandlure IV + SX, hexalure + SX, ipsdienol + SX, ipsenol + SX, japonilure + SX, lineatin + SX, litlue + SX, looplure + SX, medlure + SX, megatomoic acid + SX, methyl eugenol + SX, muscalure + SX, nerolidol + SX, orfralure + SX, oryctalure + SX, ostramone + SX, rhyncolure + SX, siglure + SX, sordidin + SX, sulcatol + SX, trimedlure + SX, trimedlure A + SX, trimedlure B1 + SX, trimedlure B2 + SX, trimedlure C + SX, trunc-call + SX, (E)-verbenol + SX, (Z)-verbenol + SX, trans-verbenol + SX, (S)-verbenone + SX.

[0381] Examples of a ratio of the compound to the present ingredient include, but are not particularly limited to 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, and 1 : 50 in the weight ratio (the compound X: the present ingredient).

[0382] The compound has control effect on harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Accordingly, the claimed invention includes a method for controlling a harmful arthropod, comprising applying an effective amount of the inventive compound to a harmful arthropod or a habitat where a harmful arthropod lives. Examples of the harmful arthropods, harmful nematodes, and harmfullmollusks include the followings. Hemiptera : from the family Delphacidae, small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), cereal leafhopper (Javesella pellucida), sugarcane leafhopper (Perkinsiella saccharicida), Tagosodes orizicolus, and the like; from the family Cicadellidae, green rice leafhopper (Nephotettix cincticeps), green paddy leafhopper (Nephotettix virescens), rice leafhopper (Nephotettix nigropictus), zigzag-striped leafhopper (Recilia dorsalis), tea green leafhopper (Empoasca onukii), potato leafhopper (Empoasca fabae), corn leafhopper (Dalbulus maidis), rice leafhopper (Cofana spectra), and the like; from the family Cercopidae, Mahanarva posticata, Mahanarva fimbriolata, and the like; from the family Aphididae, bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), green apple aphid (Aphis pomi), apple aphid (Aphis spiraecola), green peach aphid (Myzus persicae), leaf-curling plum aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false cabbage aphid (Lipaphis erysimi), potato aphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), grain aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), brown citrus aphid (Toxoptera citricida), mealy plum aphid (Hyalopterus pruni), cane aphid (Melanaphis sacchari), black rice root aphid (Tetraneura nigriabdominalis), sugarcane cottony aphid (Ceratovacuna lanigera), apple woolly aphid (Eriosoma lanigerum), and the like; from the family Phylloxeridae, grapevine phylloxera (Daktulosphaira vitifoliae), Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae), and the like; from the family Adelgidae, hemlock woolly aphid (Adelges tsugae), Adelges piceae, Aphrastasia pectinatae, and the like; from the family Pentatomidae, black rice bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), common green stink bug (Nezara antennata), white-spotted spined bug (Eysarcoris aeneus), lewis spined bug (Eysarcoris lewisi), white-spotted bug (Eysarcoris ventralis), Eysarcoris annamita, brown marmorated stink bug (Halyomorpha halys), green plant bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, and the like; from the family Cydnidae, Burrower brown bug (Scaptocoris castanea); from the family Alydidae, for example, bean bug (Riptortus pedestris), corbett rice bug (Leptocorisa chinensis), rice bug (Leptocorisa acuta), and the like; from the family Coreidae, Cletus punctiger, Australian leaf-footed bug (Leptoglossus australis), and the like; from the family Lygaeidae, oriental chinch bug (Caverelius saccharivorus), seed bug (Togo hemipterus), chinch bug (Blissus leucopterus), and the like; from the family Miridae, rice leaf bug (Trigonotylus caelestialium), sorghum plant bug (Stenotus rubrovittatus), wheat leaf bug (Stenodema calcarata), American tarnished plant bug (Lygus lineolaris), and the like; from the family Aleyrodidae, greenhouse whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus spiny whitefly (Aleurocanthus spiniferus), tea spiny whitefly (Aleurocanthus camelliae), Pealius euryae, and the like; from the family Diaspididae, Abgrallaspis cyanophylli, red scale (Aonidiella aurantii), San José scale (Diaspidiotus perniciosus), white peach scale (Pseudaulacaspis pentagona), arrowhead scale (Unaspis yanonensis), citrus snow scale (Unaspis citri), and the like; from the family Coccidae, pink wax scale (Ceroplastes rubens); from the family Margarodidae, fluted scale (Icerya purchasi) seychelles fluted scale (Icerya seychellarum), and the like; from the family Pseudococcidae, solanum mealybug (Phenacoccus solani), cotton mealybug (Phenacoccus solenopsis), Japanese mealybug (Planococcus kraunhiae), white peach scale (Pseudococcus comstocki), citrus mealybug (Planococcus citri), currant mealybug (Pseudococcus calceolariae), long-tailed mealybug (Pseudococcus longispinus), tuttle mealybug (Brevennia rehi), and the like; from the family Psyllidae, citrus psylla (Diaphorina citri), two-spotted citrus psyllid (Trioza erytreae), pear sucker (Cacopsylla pyrisuga), Cacopsylla chinensis, potato psyllid (Bactericera cockerelli), Pear psylla (Cacopsylla pyricola), and the like; from the family Tingidae, sycamore lace bug (Corythucha ciliata), aster tingid (Corythucha marmorata), Japanese pear lace bug (Stephanitis nashi), azalea lace bug (Stephanitis pyrioides), and the like; from the family Cimicidae, common bed bug (Cimex lectularius), tropical bed bug (Cimex lectularius), and the like; from the family Cicadidae, Giant Cicada (Quesada gigas), and the like; from the family Reduviidae, Triatoma infestans, Rhodonius prolixus, and the like, Triatoma spp. Lepidoptera: from the family Crambidae, rice stem borer (Chilo suppressalis), Dark-headed stem borer (Chilo polychrysus), white stem borer (Scirpophaga innotata), yellow paddy borer (Scirpophaga incertulas), Rupela albina, rice leaf roller (Cnaphalocrocis medinalis), Marasmia patnalis, rice leaf roller (Marasmia exigua), cotton leaf roller (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), cabbage webworm (Hellula undalis), grape leafroller (Herpetogramma luctuosale), bluegrass webworm (Pediasia teterrellus), rice case-worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), and the like; from the family Pyralidae, lesser cornstalk borer (Elasmopalpus lignosellus), mealworm moth (Plodia interpunctella), persimmon bark borer (Euzophera batangensis), fig moth (Cadra cautella) and the like; from the family Noctuidae, cotton worm (Spodoptera litura), beet armyworm (Spodoptera exigua), rice armyworm (Mythimna separata), cabbage moth (Mamestra brassicae), pink borer (Sesamia inferens), grass armyworm (Spodoptera mauritia), green rice caterpillar (Naranga aenescens), Spodoptera frugiperda, true armyworm (Spodoptera exempta), black cutworm (Agrotis ipsilon), beet worm (Autographa nigrisigna), rice looper (Plusia festucae), soybean looper (Chrysodeixis includens), Trichoplusia spp., Heliothis spp. (such as tobacco budworm (Heliothis virescens)), Helicoverpa spp. (such as tobacco budworm (Helicoverpa armigera), corn earworm (Helicoverpa zea)), Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), and the like; from the family Pieridae, common cabbage worm (Pieris rapae), and the like; from the family Tortricidae, oriental fruit moth (Grapholita molesta), Grapholita dimorpha, soybean moth (Leguminivora glycinivorella), Matsumuraeses azukivora, summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai), Japanese tea tortrix (Homona magnanima), apple tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), sugarcane shoot borer (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), and the like; from the family Gracillariidae, tea leaf roller (Caloptilia theivora), Asiatic apple leaf miner (Phyllonorycter ringoniella), and the like; from the family Carposinidae, peach fruit moth (Carposina sasakii), and the like; from the family Lyonetiidae, Coffee Leaf miner (Leucoptera coffeella), peach leaf miner (Lyonetia clerkella), Lyonetia prunifoliella, and the like; from the family Lymantriidae, Lymantria spp. (such as gypsy moth (Lymantria dispar)), Euproctis spp. (such as tea lymantriid (Euproctis pseudoconspersa)), and the like; from the family Plutellidae, diamondback moth (Plutella xylostella), and the like; from the family Gelechiidae, peach worm (Anarsia lineatella), sweetpotato leaf folder (Helcystogramma triannulella), pink bollworm (Pectinophora gossypiella), potato moth (Phthorimaea operculella), Tuta absoluta, and the like; from the family Arctiidae, American white moth (Hyphantria cunea), and the like; from the family Castniidae, Giant Sugarcane borer (Telchin licus), and the like; from the family Cossidae, Cossus insularis, and the like; from the family Geometridae, Ascotis selenaria, and the like; from the family Limacodidae, blue-striped nettle grub (Parasa lepida), and the like; from the family Stathmopodidae, persimmon fruit moth (Stathmopoda masinissa), and the like; from the family Sphingidae, tobacco hornworm (Acherontia lachesis), and the like; from the family Sesiidae, Nokona feralis, cherry borer (Synanthedon hector), Synanthedon tenuis, and the like: from the family Hesperiidae, rice skipper (Parnara guttata), and the like; from the family Tineidae, casemaking clothes moth (Tinea translucens), common clothes moth (Tineola bisselliella), and the like. Thysanoptera: from the family Thripidae, western flower thrips (Frankliniella occidentalis), oriental thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), onion thrips (Thrips tabaci), eastern flower thrips (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis), Echinothrips americanus, and the like; from the family Phlaeothripidae, aculeated rice thrips (Haplothrips aculeatus), and the like. Diptera: from the family Anthomyiidae, seedcorn maggot (Delia platura), onion maggot (Delia antiqua), beet leaf miner (Pegomya cunicularia), and the like; from the family Ulidiidae, sugarbeet root maggot (Tetanops myopaeformis), and the like; from the family Agromyzidae, rice leaf miner (Agromyza oryzae), tomato leaf miner (Liriomyza sativae), chrysanthemum leaf miner (Liriomyza trifolii), pea leafminer (Chromatomyia horticola), and the like; from the family Chloropidae, rice stem maggot (Chlorops oryzae), and the like; from the family Tephritidae, melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), Malaysian fruit fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), Queensland fruit fly (Bactrocera tryoni), Mediterranean fruit fly (Ceratitis capitata), apple maggot (Rhagoletis pomonella), Japanese cherry fruit fly (Rhacochlaena japonica), and the like; from the family Ephydridae, smaller rice leaf miner (Hydrellia griseola), whorl maggot (Hydrellia philippina), paddy stem maggot (Hydrellia sasakii), and the like; from the family Drosophilidae, cherry drosophila (Drosophila suzukii), and the like; from the family Phoridae, Megaselia spiracularis, and the like; from the family Psychodidae, Clogmia albipunctata, and the like; from the family Sciaridae, Bradysia difformis, and the like; from the family Cecidomyiidae, hessian fly (Mayetiola destructor), paddy gall fly (Orseolia oryzae), and the like; from the family Diopsidae, Diopsis macrophthalma, and the like; from the family Tipulidae, rice crane fly (Tipula aino), Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa), and the like; from the family Culicidae, southern house mosquito (Culex pipiens pallens), Culex tritaeniorhynchus Culex pipiens f. molestus, brown house mosquito (Culex quinquefasciatus), northern house mosquito (Culex pipiens pipiens), Culex vishnui, Asian tiger mosquito (Aedes albopictus), dengue mosquito (Aedes aegypti), Chinese malaria mosquito (Anopheles sinensis), Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus, and the like; from the family Simulidae, Prosimulium yezoensis, Simulium ornatum, and the like; from the family Tabanidae, Tabanus trigonus, and the like; from the family Muscidae, house fly (Musca domestica), false stable fly (Muscina stabulans), biting house fly (Stomoxys calcitrans), buffalo fly (Haematobia irritans), and the like; from the family Calliphoridae; from the family Sarcophagidae; from the family Chironomidae, Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai, and the like; from the family Fannidae. Coleoptera: from the family Chrysomelidae, western corn rootworm (Diabrotica virgifera virgifera), southern corn rootworm (Diabrotica undecimpunctata howardi), northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), banded cucumber beetle (Diabrotica balteata), Cucurbit Beetle(Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), barley leaf beetle (Oulema melanopus), cucurbit leaf beetle (Aulacophora femoralis), striped flea beetle (Phyllotreta striolata), Cabbage flea beetle (Phyllotreta cruciferae), Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flea beetle (Chaetocnema pulicaria), sweet-potato flea beetle (Chaetocnema confinis), potato flea beetle (Epitrix cucumeris), rice leaf beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), Laccoptera quadrimaculata, tobacco flea beetle (Epitrix hirtipennis), and the like; from the family Carabidae, Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons), and the like; from the family Scarabaeidae, cupreus chafer (Anomala cuprea), soybean beetle (Anomala rufocuprea), Anomala albopilosa, Japanese beetle (Popillia japonica), yellowish elongate chafer (Heptophylla picea), European Chafer (Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., Phyllophaga spp. (such as June beetle (Phyllophaga crinita)), and Diloboderus spp. (such as Diloboderus abderus), and the like; from the family Curculionidae, coffee bean weevil (Araecerus coffeae), sweet-potato weevil (Cylas formicarius), West Indian sweet-potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize wevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), grain weevil (Sitophilus granarius), rice plant weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), Rhabdoscelus lineatocollis, boll weevil (Anthonomus grandis), nunting billbug (Sphenophorus venatus), Southern Corn Billbug(Sphenophorus callosus), Soybean stalk weevil(Sternechus subsignatus), Sugarcane weevil(Sphenophorus levis), rusty gourd-shaped weevil (Scepticus griseus), brown gourd-shaped weevil (Scepticus uniformis), Mexican bean weevil (Zabrotes subfasciatus), pine beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus spp. (such as Aracanthus mourei), cotton root borer (Eutinobothrus brasiliensis), and the like; from the family Tenebrionidae, red meal beetle (Tribolium castaneum), mason beetle (Tribolium confusum), lesser mealworm (Alphitobius diaperinus), and the like; from the family Coccinellidae, twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), and the like; from the family Bostrychidae, common powder-post beetle (Lyctus brunneus), lesser grain borer (Rhizopertha dominica), and the like; from the family Ptinidae; from the family Cerambycidae, citrus long-horned beetle (Anoplophora malasiaca), Migdolus fryanus, and the like; from the family Elateridae, Melanotus okinawensis, barley wireworm (Agriotes fuscicollis), Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., and the like; from the family Staphylinidae, Paederus fuscipes, and the like; from the family Dermestidae, varied carpet beetle (Anthrenus verbasci), hide beetle (Dermestes maculates), khapra beetle (Trogoderma granarium), and the like; from the family Anobidae, tobacco beetle (Lasioderma serricorne) and biscuit beetle (Stegobium paniceum), and the like; from the family Laemophloeidae, flat grain beetle (Cryptolestes ferrugineus), and the like; from the family Silvanidae, saw-toothed grain beetle (Oryzaephilus surinamensis), and the like. Orthoptera: from the family Acrididae, oriental migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian plague locust (Chortoicetes terminifera), red locust (Nomadacris septemfasciata), Brown Locust (Locustana pardalina), Tree Locust (Anacridium melanorhodon), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida), desert locust (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa) Japanese grasshopper (Oxya yezoensis), rice grasshopper (Oxya japonica), Bombay locust (Patanga succincta), and the like; from the family Gryllotalpidae, oriental mole cricket (Gryllotalpa orientalis), and the like; from the family Gryllidae, house cricket (Acheta domestica),emma field cricket (Teleogryllus emma), and the like; from the family Tettigoniidae, for example, Mormon cricket (Anabrus simplex), and the like. Hymenoptera : from the family Tenthredinidae, beet sawfly (Athalia rosae), nippon cabbage sawfly (Athalia japonica), and the like; from the family Formicidae, Solenopsis spp. (such as red imported fire ant (Solenopsis invicta), tropical fire ant (Solenopsis geminata)), Atta spp. (such as Brown leaf-cutting ant (Atta capiguara)), Acromyrmex spp., Paraponera clavata, black house ant (Ochetellus glaber), little red ant (Monomorium pharaonis), Argentine ant (Linepithema humile), Formica fusca japonica, Pristomyrmex punctutus, Pheidole noda, big-headed ant (Pheidole megacephala), Camponotus spp. (such as Camponotus japonicus, Camponotus obscuripes), Pogonomyrmex spp. (such as western harvester ant (Pogonomyrmex occidentalis)), Wasmania spp. (such as Wasmania auropunctata), long-legged ant (Anoplolepis gracilipes), and the like; from the family Vespidae, Asian giant hornet (Vespa mandarinia japonica), Vespa simillima, Vespa analis Fabriciusi, Asian hornet (Vespa velutina), Polistes jokahamae, and the like; from the family Siricidae, pine wood wasp (Urocerus gigas), and the like; from the family Bethylidae. Blattodea: from the family Blattellidae, German cockroach (Blattella germanica), and the like; from the family Blattidae, smoky-brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), brown cockroach (Periplaneta brunnea), black cockroach (Blatta orientalis), and the like; from the family Termitidae, Japanese termite (Reticulitermes speratus), Formosan termite (Coptotermes formosanus), western drywood termite (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, and the like. Siphonaptera: Pulex spp. (such as human flea (Pulex irritans)), Ctenocephalides spp. (such as cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis)), Xenopsylla spp. (such as oriental rat flea (Xenopsylla cheopis)), Tunga spp. (such as chigoe flea (Tunga penetrans)), Echidnophaga spp. (such as chicken flea (Echidnophaga gallinacea)), Nosopsyllus spp. (such as European rat flea (Nosopsyllus fasciatus)). Psocodae: Pediculus spp. (such as head louse (Pediculus humanus capitis)); Phtirus spp. (such as crab louse (Pthirus pubis)); Haematopinus spp. (such as short-nosed cattle louse (Haematopinus eurysternus), pig louse (Haematopinus suis)); Damalinia spp. (such as Dalmalinia ovis, Damalinia bovis); Linognathus spp. (such as blue cattle louse (Linognathus vituli), sheep face louse (Linognathus ovillus)); Solenopotes spp. (such as capillate louse (Solenopotes capillatus)); Menopon spp. (such as common chicken louse (Menopon gallinae)); Trimenopon spp.; Trinoton spp.; Trichodectes spp. (such as dog biting louse (Trichodectes canis)); Felicola spp. (such as cat louse (Felicola subrostratus)); Bovicola spp. (such as cattle biting louse (Bovicola bovis)); Menacanthus spp. (such as chicken body louse (Menacanthus stramineus)); Werneckiella spp.; Lepikentron spp.; from the family Liposcelididae, book louse (Liposcelis subfuscas), Liposcelis bostrychophilus, Liposcelis simulans, Liposcelis divinatorius, Liposcelis entomophila, and the like. Thysanura: from the family Lepismatidae, oriental silverfish (Ctenolepisma villosa), moth fish (Lepisma saccharina), and the like. Acari: from the family Tetranychidae, common red spider mite (Tetranychus urticae), kanzawa spider mite (Tetranychus kanzawai), red spider mite (Tetranychus evansi), citrus red mite (Panonychus citri), fruit-tree red spider mite (Panonychus ulmi), Oligonychus spp., and the like; from the family Eriophyidae, Japanese citrus rust mite (Aculops pelekassi), Phyllocoptruta citri, tomato mite (Aculops lycopersici), purple mite (Calacarus carinatus), tea rust mite (Acaphylla theavagrans), Eriophyes chibaensis, apple bud mite (Aculus schlechtendali), Aceria diospyri, Aceria tosichella, Shevtchenkella sp., and the like; from the family Tarsonemidae, broad mite (Polyphagotarsonemus latus), and the like; from the family Tenuipalpidae, Brevipalpus phoenicis, and the like; from the family Tuckerellidae; from the family Ixodidae, for example, Haemaphysalis spp. (such as Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata), Dermacentor spp. (such as American dog tick (Dermacentor variabilis), Dermacentor taiwanicus, Rocky Mountain wood tick (Dermacentor andersoni)), Ixodes spp. (such as Ixodes ovatus, Ixodes persulcatus, black-legged tick (Ixodes scapularis), Ixodes pacificus, Ixodes holocyclus), Amblyomma spp. (such as lone star tick (Amblyomma americanum), gulf coast tick (Amblyomma maculatum)), Boophilus spp. (such as Rhipicephalus (Boophilus) microplus, Boophilus annulatus), and Rhipicephalus spp. (such as brown dog tick (Rhipicephalus sanguineus), Rhipicephalus appendiculatus); from the family Acaridae, cereal mite (Tyrophagus putrescentiae), grassland mite (Tyrophagus similis), and the like; from the family Pyroglyphidae, American house dust mite (Dermatophagoides farinae), European house dust mite (Dermatophagoides pteronyssinus), and the like; from the family Cheyletidae, Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella yasguri, and the like; Argas spp. (such as fowl tick (Argas persicus)), Ornithodorus spp. (such as Ornithodorus hermsi, Ornithodorus turicata), Psoroptes spp. (such as sheep scab mite (Psoroptes ovis), horse psoroptic mange mite (Psoroptes equi)), Knemidocoptes spp. (such as Knemidocoptes mutans), Notoedres spp. (such as Notoedres cati, Notoedres muris), Sarcoptes spp. (such as itch mite (Sarcoptes scabiei)), Otodectes spp. (such as ear mange mite (Otodectes cynotis)), Listrophorus spp. (such as Listrophorus gibbus), Chorioptes spp., Hypodectes spp., Pterolichus spp., Cytodites spp., Laminosioptes spp., Dermanyssus spp. (such as bird mite (Dermanyssus gallinae)), Ornithonyssus spp. (such as feather mite (Ornithonyssus sylviarum), tropical rat mite (Ornithonyssus bacoti)), Varroa spp. (such as Varroa jacobsoni), Cheyletiella spp. (such as Cheyletiella yasguri, Cheyletiella blakei), Ornithocheyletia spp., Demodex spp. (such as dog follicle mite (Demodex canis), cat follicle mite (Demodex cati)), Myobia spp., Psorergates spp., Trombicula spp. (such as Trombicula akamushi, Trombicula pallida, Trombicula scutellaris) . Araneae: from the family Eutichuridae, Cheiracanthium japonicum, and the like; from the family Theridiidae, red-back spider (Latrodectus hasseltii), and the like. Polydesmida: from the family Paradoxosomatidae, flat-backed millipede (Oxidus gracilis), Nedyopus tambanus, and the like; Isopoda: from the family Armadillidiidae, common pill bug (Armadillidium vulgare), and the like; Chilopoda: from the family Scutigeridae, Thereuonema hilgendorfi, and the like; from the family Scolopendridae, giant tropical centipede (Scolopendra subspinipes) , and the like; from the family Ethopolyidae, Bothropolys rugosus, and the like; Gastropoda: from the family Limacidae, tree slug (Limax marginatus), garden tawny slug (Limax flavus), and the like; from the family Philomycidae, Meghimatium bilineatum, and the like; from the family Ampullariidae, golden apple snail (Pomacea canaliculata), and the like; from the family Lymnaeidae, Austropeplea ollula, and the like. Nematoda: from the family Aphelenchoididae, rice white-tip nematode (Aphelenchoides besseyi), and the like; from the family Pratylenchidae, root lesion nematode (Pratylenchus coffeae), Pratylenchus brachyurus, California meadow nematode (Pratylenchus neglectus), Radopholus similis, and the like; from the family Heteroderidae, javanese root-knot nematode (Meloidogyne javanica), southern root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera rostochiensis), white potato cyst nematode (Globodera pallida), and the like; from the family Hoplolaimidae, Rotylenchulus reniformis, and the like; from the family Anguinidae, strawberry bud nematode (Nothotylenchus acris), stem nematode (Ditylenchus dipsaci), and the like; from the family Tylenchulidae, citrus nematode (Tylenchulus semipenetrans), and the like; from the family Longidoridae, dagger nematode (Xiphinema index), and the like; from the family Trichodoridae; from the family Parasitaphelenchidae, pine wilt disease (Bursaphelenchus xylophilus), and the like.

[0383] The compound may be also applied to harmuful arthropods such as harmful insects and harmful mites, harmful mollusks, and harmful nematodes which have a reduced agent-sensitivity to or a developed agent-resistance to an insecticide or a miticide, a molluscicide or a nematicide.

[0384] The compound may be also used to protect a plant from a plant disease caused by insect-borne viruses or insect-borne bacteria.

[0385] Examples of the insect-borne viruses are recited as follows.

[0386] Rice tungro spherical virus, Rice tungro bacilliform virus, Rice grassy stunt virus, Rice ragged stunt virus, Rice stripe virus, Rice black streaked dwarf virus, Southern rice black-streaked dwarf virus, Rice gall dwarf virus, Rice hoja blanca virus, Rice yellow stunt virus, Rice yellow mottle virus, Rice dwarf virus, Northern cereal mosaic virus, Barley yellow dwarf virus, Barley mild mosaic virus, Barley yellow dwarf virus-PAV, Cereal yellow dwarf virus-RPS, Wheat yellow leaf virus, Oat sterile dwarf virus, Wheat streak mosaic virus, Maize dwarf mosaic virus, Maize stripe virus, Maize chlorotic mottle virus, Maize chlorotic dwarf virus, Maize rayado fino virus, Sugarcane mosaic virus, Fiji disease virus , Sugarcane yellow leaf virus, Soybean mild mosaic virus, Cycas necrotic stunt virus, Soybean dwarf virus, Milk vetch dwarf virus, Soybean mosaic virus, Alfalfa mosaic virus, Bean yellow mosaic virus, Bean common mosaic virus, Southern bean mosaic virus, Peanut stunt virus, Broad bean wilt virus 1, Broad bean wilt virus 2, Broad bean necrosis virus, Broad bean yellow vein virus, Clover yellow vein virus, Peanut mottle virus, Tobacco streak virus, Bean pod mottle virus, Cowpea chlorotic mottle virus, Mung bean yellow mosaic virus, Soybean crinkle leaf virus, Tomato chlorosis virus, Tomato spotted wilt virus, Tomato yellow leaf curl virus, Tomato aspermy virus, Tomato infectious chlorosis virus, Potato leafroll virus, Potato virus Y, Melon yellow spot virus, Melon necrotic spot virus, Watermelon mosaic virus, Cucumber mosaic virus, Zucchini yellow mosaic virus, Turnip mosaic virus, Turnip yellow mosaic virus, Cauliflower mosaic virus, Lettuce mosaic virus, Celery mosaic virus, Beet mosaic virus, Cucurbit chlorotic yellows virus, Capsicum chlorosis virus, Beet pseudo yellows virus, Leak yellow stripe virus, Onion yellow dwarf virus, Sweet potato feathery mottle virus, Sweet potato shukuyo mosaic virus, Strawberry mottle virus, Strawberry mild yellow edge virus, Strawberry pseudo mild yellow edge virus, Strawberry crinkle virus, Strawberry vein banding virus, plum pox virus, Chrysanthemum stem necrosis virus, Impatiens necrotic spot virus, Iris yellow spot virus, Lily mottle virus, Lilly symptomless virus, Tulip mosaic virus, and the others.

[0387] Examples of the insect-borne bacteria are recited as follows.

[0388] Candidatus Phytoplasma oryzae, Candidatus Phytoplasma asteris, Maize bushy stunt phytoplasma, Candidatus Liberbacter asiaticus, Candidatus Liberbacter africanus, Candidatus Liberbacter americanus.

[0389] The composition for controlling harmful arthropods of the present invention comprises the inventive compound and an inert carrier. The composition for controlling harmful arthropods of the present invention is usually prepared by mixing the inventive compound with an inert carrier such as solid carrier, liquid carrier or gaseous carrier, and if necessary, adding surfactants and the other auxiliary agents for formulation, to formulate into emulsifiable concentrates, oil solutions, dust formulations, granules, wettable powders, flowables, microcapsules, aerosols, smoking agents, poison baits, resin formulations, shampoo formulations, paste-like formulations, foams, carbon dioxide formulations, and tablets and the others. Such formulations may be processed into mosquito repellent coils, electric mosquito repellent mats, liquid mosquito formulations, smoking agents, fumigants, sheet formulations, spot-on formulations or formulations for oral treatment. The composition for controlling harmful arthropods of the present invention comprises usually 0.01 to 95 % by weight of the inventive compound.

[0390] Examples of the solid carrier to be used in the formulation include fine powders or granules of clays (for example, kaolin clay, diatomaceous earth, bentonite, Fubasami clay, or acid white clay), dry silica, wet silica, hydrated silica, talcs, ceramics, other inorganic minerals (for example, sericite, quartz, sulfur, active carbon, or calcium carbonate) or chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, or ammonium chloride) and the others; as well as synthetic resins (for example, polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate or polyethylene terephthalate; nylon resins (for example, nylon-6, nylon-11, or nylon-66); polyamide resins; polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, and the others).

[0391] Examples of the liquid carriers include water; alcohols (for example, methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxy ethanol); ketones (for example, acetone, methyl ethyl ketone, or cyclohexanone); aromatic hydrocarbons (for example, toluene, xylene, ethyl benzene, dodecyl benzene, phenyl xylyl ethane, or methylnaphthalene); aliphatic hydrocarbons (for example, hexane, cyclohexane, kerosene, or light oil); esters (for example, ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, or propylene glycol monomethyl ether acetate); nitriles (for example, acetonitrile, or isobutyronitrile); ethers (for example, diisopropyl etheR14-dioxane, 1,2-dimethoxyethane, diethyleneglycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl-1-butanol); amides (for example, N,N-dimethylformamide (hereinafter, referred to as "DMF") or N,N-dimethylacetamide); sulfoxides (for example, dimethyl sulfoxide); propylene carbonate; and vegetable oils (for example, soybean oil or cottonseed oil).

[0392] Examples of gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

[0393] Examples of the surfactants include nonionic surfactants such as polyoxyethylenated alkyl ethers, polyoxyethylenated alkyl aryl ethers, and polyethylene glycol fatty acid esters; and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates and alkyl sulfates.

[0394] Examples of the other auxiliary agents for formulation include a binder, a dispersant, a colorant and a stabilizer. Specific examples include casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives and alginic acid), lignin derivatives, bentonite, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone and polyacrylic acids), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, and a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol.

[0395] Examples of a base material of the resin formulation include polyvinyl chloride polymers, polyurethane, and the others, and a plasticizer such as phthalate esters (for example, dimethyl phthalate, and dioctyl phthalate), adipic acid esters and stearic acid may be added to the base material, if necessary. The resin formulation can be prepared by kneading the compound in the base material with a conventional kneading machine, and then molding it by injection molding, extrusion molding, or pressure molding and the like. The resultant resin formulation can be subjected to further molding or cutting procedure, if necessary, to be processed into shapes such as a plate, film, tape, net and string shape. The resin formulation can be processed into animal collars, animal ear tags, sheet products, trap strings, gardening supports, and other products.

[0396] Examples of a base material for the poison bait include bait ingredients such as grain powder, vegetable oil, saccharide and crystalline cellulose, and if necessary, with an addition of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, accidental ingestion inhibitors for children and pets such as a chili powder, and insect attraction fragrances such as cheese flavor, onion flavor and peanut oil.

[0397] The method for controlling harmful arthropods of the present invention is conducted by applying an effective amount of the inventive compound, or the inventive composition, to a harmful arthropod directly and / or a habitat where the harmful arthropod lives (for example, plant bodies, soil, an interior of a house, and animal bodies). Further, the effective amount of the same can be applied to seeds. Examples of a method for controlling harmful arthropods of the present invention include foliar application, soil application, root application, shower application, smoking application, water-surface application, and seed application.

[0398] As used herein, examples of the plant include whole plant, stem and leaf, flower, ear, fruit, tree stem, branch, crown, seed, vegetative reproductive organ, and seedling.

[0399] The vegetative reproductive organ represents a part of plant such as root, stem and leaf, which has a growth capacity if the part is cut off from its plant and then placed in the soil. Examples of the vegetative reproductive organ include tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. The "stolon" is often referred to as "runner", and the "propagule" is often referred to as "brood bud", which is divided into broad bud and bulbil. The vine cutting represents a shoot (which is a generic name of leaf and stem) of sweet potato (Ipomoea batatas) and Japanese yam (Dioscorea japonica), etc. The bulb, corm or solid bulb, tuber, rhizome, cane cuttings, rhizophore, and tuberous root are also collectively referred to as "bulb". For example, when the cultivation of potato starts with planting tubers in the soil, the used tuber is generally referred to as "seed potato".

[0400] Examples of a method for controlling harmful arthropods by applying an effective amount of the inventive compound or the inventive composition to soils include a method of applying an effective amount of the inventive compound or the inventive composition to soils before planting plants or after planting plants, a method of applying an effective amount of the inventive compound or the inventive composition to a root part of a crop to be protected from damage such as ingestion by harmful arthropods, and a method of controlling harmful arthropods that ingest a plant by permeating and transferring an effective amount of the inventive compound or the inventive composition from a root into the interior of the plant body. More specifically, examples of the application method include planting hole treatment (spraying into planting holes, soil mixing after planting hole treatment), plant foot treatment (plant foot spraying, soil mixing after plant foot treatment, irrigation at plant foot, plant foot treatment at a later seeding raising stage), planting furrow treatment (planting furrow spraying, soil mixing after planting furrow treatment), planting row treatment (planting row spraying, soil mixing after planting row treatment, planting row spraying at a growing stage), planting row treatment at the time of sowing (planting row spraying at the time of sowing, soil mixing after planting row treatment at the time of sowing), broadcast treatment (overall soil surface spraying, soil mixing after broadcast treatment), side-article treatment, treatment of water surface (application to water surface, application to water surface after flooding), other soil spraying treatment (spraying of a granular formulation on leaves at a growing stage, spraying under a canopy or around a tree stem, spraying on the soil surface, mixing with surface soil, spraying into seed holes, spraying on the ground surfaces of furrows, spraying between plants), other irrigation treatment (soil irrigation, irrigation at a seedling raising stage, drug solution injection treatment, irrigation of a plant part just above the ground, drug solution drip irrigation, chemigation), seedling raising box treatment (spraying into a seedling raising box, irrigation of a seedling raising box, flooding into a seedling raising box with drug solution), seedling raising tray treatment (spraying on a seedling raising tray, irrigation of a seedling raising tray, flooding into a seedling raising tray with drug solution), seedbed treatment (spraying on a seedbed, irrigation of a seedbed, spraying on a lowland rice nursery, immersion of seedlings), seedbed soil incorporation treatment (mixing with seedbed soil, mixing with seedbed soil before sowing, spraying at sowing before covering with soils, spraying at sowing after covering with soils, mixing with covering with soils), and other treatment (mixing with culture soil, plowing under, mixing with surface soil, mixing with soil at the place where raindrops fall from a canopy, treatment at a planting position, spraying of a granule formulation on flower clusters, mixing with a paste fertilizer).

[0401] When the composition for controlling harmful arthropod of the present invention is used for controlling pests in an agricultural field, an applied dose as an amount of the inventive compound is usually within a range from 1 to 10,000 g per 10,000 m 2< . When the inventive composition is applied to seeds, an applied dose as an amount of the inventive compound is usually within a range from 0.001 to 100 g relative to 1 kg of the seeds. When the composition for controlling harmful arthropod of the present invention is formulated into the emulsifiable concentrate, the wettable powder, or the flowable formulation etc., the inventive composition is usually applied by diluting it with water in such a way that a concentration of the active ingredient of the inventive composition is usually within a range from 0.01 to 10,000 ppm. The granular formulation, or the powder formulation etc., is usually applied as itself.

[0402] These formulations and diluents of the formulations with water may be directly sprayed to a harmful arthropod or a plant such as a crop to be protected from the harmful arthropod, or applied to a soil in a cultivated area to control the pests that inhabits the soil.

[0403] Also, the resin formulation processed into a sheet shape or string shape may be wrapped around a crop, stretched near a crop, spread on a foot soil of a plant, or the like.

[0404] When the composition for controlling harmful arthropod of the present invention is used to control harmful arthropods that live inside a house, an applied dose as an amount of the inventive compound is usually within a range from 0.001 to 1,000 mg per 1 m 2< of an area to be treated, in the case of using it on a planar area. In the case of using it spatially, the applied dose as an amount of the inventive compound is usually within a range from 0.001 to 500 mg per 1 m 3< of the space to be treated. When the composition for controlling harmful arthropod of the present invention is formulated into emulsifiable concentrates, wettable powders, flowables or the others, the formulation is usually applied after diluting it with water in such a way that a concentration of the active ingredient is usually within a range from 0.1 to 10,000 ppm, and then sparging it. In the case of being formulated into oil solutions, aerosols, smoking agents, poison baits and the others, the formulation is used as itself.

[0405] When the composition for controlling harmful arthropod of the present invention is used for controlling external parasites of livestock such as cows, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, the inventive composition can be applied to the animal by a known method in the veterinary field. Specifically, when systemic control is intended, the inventive composition is administered to the animal as a tablet, a mixture with feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injections). On the other hand, when non-systemic control is intended, the inventive composition is applied to the animal by means of spraying of the oil solution or aqueous solution, pour-on or spot-on treatment, or washing of the animal with a shampoo formulation, or by putting a collar or ear tag made of the resin formulation to the animal. In the case of administering to an animal body, the dose of the inventive compound is usually within a range from 0.1 to 1,000 mg per 1 kg of a body weight of the animal.

[0406] Also the inventive compound or the composition can be used as an agent for controlling harmful arthropods in the agricultural land such as field, paddy, lawn and orchard. The inventive compound can control harmful arthropods in an agricultural land in which the below-mentioned plants are cultivated. Crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugarcane, tobacco, and the others; Vegetables: solanaceous vegetables (for example, eggplant, tomato, green pepper, hot pepper, and potato), cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, water melon, and melon), cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, and cauliflower), asteraceous vegetables (for example, burdock, crown daisy, artichoke, and lettuce), liliaceous vegetables (for example, green onion, onion, garlic, and asparagus), ammiaceous vegetables (for example, carrot, parsley, celery, and parsnip), chenopodiaceous vegetables (for example, spinach and Swiss chard), lamiaceous vegetables (for example, perilla frutescens, mint, and basil), strawberry, sweet potato, dioscorea japonica, colocasia, flowering plants, foliage plants, and the others; Fruits: pomaceous fruits (for example, apple, pear, Japanese pear, Chinese quince, and quince), stone fleshy fruits (for example, peach, plum, nectarine, Prunus mume, cherry fruit, apricot, and prune), citrus fruits (for example, citrus unshiu, orange, lemon, lime, and grapefruit), nuts (for example, chestnut, walnuts, hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts), berry fruits (for example, blueberry, cranberry, blackberry, and raspberry), grape, kaki persimmon, olive, Japanese plum, banana, coffee, date palm, coconuts, and the others; Trees other than fruits tea, mulberry, flowering plants, roadside trees (for example, ash, birch, dogwood, eucalyptus, Ginkgo biloba, lilac, maple, Quercus, poplar, Judas tree, Liquidambar formosana, plane tree, zelkova, Japanese arborvitae, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidate),

[0407] The above plants also include a plant that can be generated by a natural crossbreeding, a plant that can be generated by mutations, an F1 hybrid plant, and a genetically modified crop. Examples of the genetically modified crop include a plant modified to have the resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvoylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, or herbicides such as bromoxynil and dicamba; a plant modified to synthesize a selective toxin known to be produced in Bacillus such as Bacillus thuringiensis; and a plant modified to have a specific insecticidal activity by synthesizing a gene fragment partially corresponding to an endogenous gene derived from a harmful insect to induce the gene silencing (RNAi; RNA interference) in the target harmful insect.

[0408] The above-mentioned plants may be genetically modified crops.EXAMPLES

[0409] Hereinafter, the present invention is explained in more detail by using the Preparation Example, the Reference Preparation Example, the Formulation Example, and the Test Example, however, the present invention should not be limited to these examples.Preparation Example 1

[0410] A mixture of 2,4-dibromothiazole 15 g, 4-fluorophenyl boronic acid 9.5 g, palladium (II) acetate 690 mg, 4,5'-bis(diphenylphoshino)-9,9'-dimethyl xanthene 1.8 g, tripotassium phosphate 39 g, and THF 300 mL was stirred at 60°C for 10 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain an intermediate compound 1 represented by the below-mentioned formula 12 g. Intermediate compound 1: 1< H-NMR (CDCl 3 ) δ: 7.95-7.91 (2H, m), 7.21 (1H, s), 7.16-7.11 (2H, m).Preparation Example 2

[0411] To a mixture of diisopropyl amine 1.2 mL and THF 5 mL was added butyl lithium (1.6 M hexane solution) 5.7 mL at - 50°C, and the mixture was stirred for 20 minutes. To the resulting mixture was added a mixture of the intermediate compound 1 1.5 g and THF 7 mL, and the mixture was stirred for 1 hour. To the resulting mixture was added zinc chloride (1.0 M diethyl ether solution) 15 mL. The resulting mixture was raised gradually from -50°C to room temperature, and the mixture was stirred at room temperature for 2 hours. To the resulting mixture were added 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyridine 0.59 g, which was prepared according to the method described in WO 2016 / 121969, tetrakis(triphenylphosphine)palladium (0) 340 mg, and THF 5 mL, and the mixture was stirred at 50°C for 3 hours. To the resulting mixture was added 2N hydrochloric acid, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain an intermediate compound 2 represented by the below-mentioned formula 920 mg. Intermediate compound 2: 1< H-NMR (CDCl 3 ) δ: 8.39 (1H, d), 8.37 (1H, d), 7.97 (2H, dd), 7.38 (1H, dd), 7.15 (2H, t), 4.53 (2H, t).Preparation Example 3

[0412] To a mixture of the intermediate compound 2 920 mg, sodium hydride (60 %, oily) 76 mg, and DMF 5 mL was added ethanethiol 0.14 mL, and the mixture was stirred at room temperature for 8 hours. To the resulting mixture was added saturated aqueous sodium hydrocarbonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 1 represented by the below-mentioned formula 270 mg. Compound 1: 1< H-NMR (CDCl 3 ) δ: 8.38-8.36 (2H, m), 8.00-7.93 (2H, m), 7.38-7.33 (1H, m), 7.17-7.12 (2H, m), 4.53 (2H, t), 3.02 (2H, q), 1.37 (3H, t); (not within the claims).Preparation Example 4

[0413] To a mixture of the compound 1 270 mg, and ethyl acetate 5 mL was added m-chloroperbenzoic acid (74%) 320 mg under ice-cooling, and the mixture was raised to room temperature, and thereafter, the mixture was stirred for 4 hours. To the resulting mixture were added saturated aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 2 represented by the below-mentioned formula 150 mg. Compound 2: 1< H-NMR (CDCl 3 ) δ: 8.38 (1H, d), 8.26 (1H, d), 7.98-7.94 (2H, m), 7.35 (1H, dd), 7.20-7.14 (2H, m), 4.53 (2H, t), 3.62 (2H, q), 1.42 (3H, t); (not within the claims).Preparation Example 5

[0414] An intermediate compound 3 was obtained by using cyclopropyl boronic acid in place of 4-fluorophenyl boronic acid according to the method described in the Preparation Example 1. Intermediate compound 3: 1< H-NMR (CDCl 3 ) δ: 6.96 (1H, s), 2.34-2.24 (1H, m), 1.18-1.07 (4H, m).Preparation Exmaple 6

[0415] An intermediate compound 4 was obtained by using the intermediate compound 3 in place of the intermediate compound 1 according to the method described in the Preparation Example 2. Intermediate compound 4: 1< H-NMR (CDCl 3 ) δ: 8.32 (1H, dd), 8.28 (1H, dd), 7.34 (1H, dd), 4.56-4.43 (2H, m), 2.34-2.26 (1H, m), 1.23-1.08 (4H, m).Preparation Example 7

[0416] A mixture of the intermediate compound 705 mg, ethanethiol 190 µL, tris(benzylideneacetone)palladium (0) 300 mg, 4,5'-bis(diphenylphoshino)-9,9'-dimethylxanthene 380 mg, diisopropylethylamine 840 µL, and cyclopently methyl ether 5 mL was stirred at 100°C for 8 hours. The resulting mixture was allowed to cool, and thereafter, thereto was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 3 represented by the below-mentioned formula 490 mg. Compound 3: 1< H-NMR (CDCl 3 ) δ: 8.31 (1H, d), 8.03 (1H, dd), 7.42-7.28 (1H, m), 4.53-4.45 (2H, m), 3.32-3.11 (2H, m), 2.40-2.24 (1H, m), 1.33 (3H, t), 1.18-1.09 (4H, m); (not within the claims).Preparation Example 8

[0417] The compound 4 was obtained by using compound 3 in place of compound 1 according to the method described in the Preparation Example 4. Compound 4: 1< H-NMR (CDCl 3 ) δ: 8.33 (1H, dd), 8.12 (1H, dd), 7.31 (1H, dd), 4.50 (2H, d), 3.48 (2H, q), 2.36-2.28 (1H, m), 1.34 (3H, t), 1.25-1.18 (2H, m), 1.14-1.10 (2H, m); (not within the claims).Preparation Example 9

[0418] A mixture of ethyl chloro(hydroxyimimo) acetate 0.15 g, which was prepared according to the method described in WO 2012 / 117421, 2-ethanesulfonyl-1-[5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl]ethanone (hereinafter, referred to as "Intermediate compound 5"), which was prepared according to the method described in WO 2016 / 121969, 0.38 g, trimethylamine 0.22 g, and ethanol 3 mL was stirred at room temperature for 12 hours. To the resulting mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 5 represented by the below-mentioned formula 100 mg. Compound 5: 1< H-NMR (CDCl 3 ) δ: 8.54 (1H, d), 7.97 (1H, d), 7.42 (1H, dd), 4.57 (2H, t), 4.51 (2H, q), 3.77 (2H, q), 1.47-1.28 (6H, m); (not within the claims).Preparation Example 10

[0419] A mixture of the compound 5 400 mg, 1N aqueous lithium hydroxide solution 1 mL, and THF 3 mL was stirred at room temperature for 5 hours. To the resulting mixture was added water 5 mL, and the mixture was extracted with MTBE. To the resulting aqueous layer was added 2N hydrochloric acid to adjust pH to 4, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was added to a mixture of triethylamine 222 mg, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt 0.38 g, and isobutyl amine 141 mg under ice-cooling. The resulting mixture was raised to room temperature, and stirred for 8 hours. To the resulting mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 6 represented by the below-mentioned formula 260 mg. Compound 6: 1< H-NMR (CDCl 3 ) δ: 8.52 (1H, d), 7.90 (1H, d), 7.40 (1H, dd), 6.63 (1H, br s), 4.56 (2H, t), 3.80 (2H, q), 3.33 (2H, t), 1.98-1.91 (1H, m), 1.45 (3H, t), 1.01 (6H, d); (not within the claims).Preparation Example 11

[0420] The compound 7 and the compound 8 each represented by the below-mentioned formula were obtained according to the Preparation Example 9. Compound 7: 1< H-NMR (CDCl 3 ) δ: 8.56 (1H, t), 8.13 (2H, s), 8.07-8.03 (2H, m), 7.47 (1H, dd), 4.60 (2H, t), 3.77 (2H, q), 1.37 (3H, t); (not within the claims).

[0421] Compound 8: 1< H-NMR (CDCl 3 ) δ: 8.54 (1H, dd), 7.99 (1H, dd), 7.72-7.66 (2H, m), 7.44 (1H, dd), 7.23-7.15 (2H, m), 4.58 (2H, t), 3.55 (2H, q), 1.29 (3H, t); (not within the claims).Preparation Example 12

[0422] To a mixture of the intermediate compound 5 1.7 g, and ally bromide 320 mg, and DMSO 10 mL was added potassium hydroxide 320 mg at room temperature under nitrogen atmosphere, and the mixture was stirred at 80°C for 30 minutes. To the resulting mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the resulting residue was added methanol 10 mL, and ozone was bubbled to the resulting mixture at room temperature for 10 minutes. To the resulting mixture was added dimethyl sulfide 530 µL at -78°C, and the mixture was stirred at room temperature for 1 day. The resulting mixture was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain an intermediate compound 6 represented by the below-mentioned formula 1.2 g. Intermediate compound 6: 1< H-NMR (CDCl 3 ) δ: 9.77 (1H, s), 8.49 (1H, d), 8.18 (1H, d), 7.41 (1H, dd), 6.39 (1H, dd), 4.59 (2H, t), 3.62-3.53 (2H, m), 3.30-3.07 (2H, m), 1.40 (3H, t).Preparation Example 13

[0423] To a mixture of the intermediate compound 6 250 mg and ethanol 2 mL was added ammonium acetate 53 mg at room temperature under nitrogen atmosphere, and the mixture was stirred at 80°C for 1 hour. To the resulting mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the inventive compound 9 represented by the below-mentioned formula 31 mg. Inventive compound 9: 1< H-NMR (CDCl 3 ) δ: 10.13 (1H, s), 8.55 (1H, dd), 8.32 (1H, d), 7.32 (1H, dd), 6.90 (1H, t), 6.74 (1H, t), 4.51 (2H, t), 3.14 (2H, q), 1.26 (3H, t).Preparation Example 14

[0424] To a mixture of the inventive compound 9 200 mg, methyl iodide 160 µL and DMF 2 mL was added sodium hydride (60 %, oily) 23 mg at room temperature, and the mixture was stirred for 30 minutes. To the resulting mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the inventive compound 10 represented by the below-mentioned formula 120 mg. Inventive compound 10: 1< H-NMR (CDCl 3 ) δ: 8.44 (1H, dd), 7.74 (1H, dd), 7.35 (1H, dd), 6.73 (1H, d), 6.63 (1H, d), 4.53 (2H, t), 3.58 (3H, s), 2.92 (2H, q), 1.14 (3H, t).Preparation Example 15

[0425] The inventive compound 11 was obtained by using isopropyl iodide in place of methyl iodide according to the Preparation Example 14. Inventive compound 11: 1< H-NMR (CDCl 3 ) δ: 8.44 (1H, dd), 7.67 (1H, dd), 7.35 (1H, dd), 6.88 (1H, d), 6.67 (1H, d), 4.53 (2H, t), 4.31-4.24 (1H, m), 2.91 (2H, q), 1.37 (6H, d), 1.15 (3H, t).Preparation Example 16

[0426] To a mixture of the intermediate compound 6 240 mg and toluene 10 mL was added lowesson reagent 630 mg at room temperature, and the mixture was stirred at 80°C for 1 hour. To the resulting mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the inventive compound 12 represented by the below-mentioned formula 190 mg. Inventive compound 12: 1< H-NMR (CDCl 3 ) δ: 8.44 (1H, d), 7.94 (1H, d), 7.53 (1H, d), 7.42 (1H, d), 7.36 (1H, dd), 4.54 (2H, t), 3.34 (2H, q), 1.27 (3H, t).Preparation Example 17

[0427] To a mixture of the intermediate compound 5 10 g and chloroform 40 mL were added N-chlorosuccinimide 4.1 g and p-toluenesulfonic acid 530 mg successively, and the mixture was stirred at 60°C for 2 hours. The resulting mixture was allowed to cool to room temperature, and thereto was added aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting reside was subjected to a silica gel column chromatography to obtain the intermediate compound 7 represented by the below-mentioned formula 2.1 g. Intermediate compound 7: 1< H-NMR (CDCl 3 ) δ: 8.46 (1H, d), 8.19 (1H, d), 7.41 (1H, dd), 4.59 (2H, t), 3.61-3.47 (1H, m), 3.43-3.28 (2H, m), 1.46 (3H, t).Preparation Example 18

[0428] To a mixture of the intermediate compound 7 1.0 g and ethanol 40 mL were added thiourea 580 mg and pyridine 400 mg successively at room temperature, and the mixture was stirred under reflux for 2 hours. The resulting mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 13 represented by the below-mentioned formula 200 mg. Compound 13: 1< H-NMR (CDCl 3 ) δ: 8.40 (1H, dd), 7.93 (1H, dd), 7.32 (1H, dd), 5.40 (2H, s), 4.52 (2H, t), 3.87 (2H, q), 1.41 (3H, t); (not within the claims).Preparation Example 19

[0429] To a mixture of the intermediate compound 7 500 mg and ethanol 5 mL was added thiobenzamide 520 mg at room temperature, and the mixture was stirred at 100°C for 30 minutes. The resulting mixture was allowed to cool to room temperature, and water was added thereto, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain the compound 14 represented by the below-mentioned formula 74 mg. Compound 14: 1< H-NMR (CDCl 3 ) δ: 8. 45 (1H, d), 8.23 (1H, d), 8.02 (2H, dd), 7.56-7.48 (3H, m), 7.40 (1H, dd), 4.56 (2H, t), 4.05 (2H, q), 1.46 (3H, t); (not within the claims).Preparation Example 20

[0430] To a mixture of the compound 13 230 mg and DMF 2 mL was added t-butyl nitrite 80 µL at 60°C, and the mixture was stirred under reflux for 30 minutes. The resulting mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 15 represented by the below-mentioned formula 73 mg. Compound 15: 1< H-NMR (CDCl 3 ) δ: 8.99 (1H, s), 8.44 (1H, d), 8.14 (1H, d), 7.39 (1H, dd), 4.55 (2H, t), 4.04 (2H, q), 1.42 (3H, t) ; (not within the claims).Preparation Example 21

[0431] A mixture of the intermediate compound 5 30 g and N,N-dimethylformamide dimethyl acetal 120 mL was stirred at room temperature for 12 hours. The precipitated out-solids were filtered, and washed with MTBE. The resulting solids were dried under reduced pressure to obtain the intermediate compound 8 represented by the below-mentioned formula 24 g. Intermediate compound 8: 1< H-NMR (CDCl 3 ) δ: 8.30 (1H, dd), 7.96 (1H, dd), 7.84 (1H, s), 7.34 (1H, dd), 4.52 (2H, t), 3.47 (2H, q), 3.26 (3H, s), 2.70 (3H, s), 1.33 (3H, t).Preparation Example 22

[0432] To a mixture of the intermediate compound 8 0.5 mg, sodium hydrogen carbonate 0.2 g, and ethanol 3 mL was added 4-fluorophenyl hydrazine hydrochloride salt 0.3 mg, and the mixture was stirred under reflux for 5 hours. The resulting mixture was allowed to cool to room temperature, water was added thereto, and the mixture was extracted with MTBE. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the compound 16 represented by the below-mentioned formula 0.53 g. Compound 16: 1< H-NMR (CDCl 3 ) δ: 8.38 (1H, d), 8.13 (1H, d), 7.36-7.33 (1H, m), 7.25-7.22 (3H, m), 7.07-7.00 (2H, m), 4.49 (2H, t), 3.29 (2H, q), 1.31 (3H, t); (not within the claims).

[0433] Next, examples of the compounds which are prepared by either the Preparation Examples described in Examples or the Process described herein are shown below.

[0434] As used herein, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, "i-Pr" represents an isopropyl group, "c-Pr" represents a cyclopropyl group, "Ph" represents a phenyl group, "Py2" represents a 2-pyridyl group, "Py3" represents a 3-pyridyl group, "Py4" represents a 4-pyridyl group, and "Bn" represents a benzyl group. When c-Pr, Ph, Py2, Py3, and Py4 have a substituent, the substituent is written with its substituted position before the symbol. For example, "1-CN-c-Pr" represents a 1-cyanocyclopropyl group, "3,4-F 2 -Ph" represents a 3,4-difluorophenyl group, "4-CF 3 -Py2" represents a 4-(trifluoromethyl)-2-pyridyl group, and "5-OCH 2 CF 2 CF 3 -Py2" represents a 5-(2,2,3,3,3-pentafluoropropoxy)-2-pyridyl group.

[0435] Here Q10 to Q28 represents the following groups respectively (Q18 to Q22 represent above-mentioned formula Q2 and Q23 to Q28 represent above-mentioned formula Q3 and are not within the claims).

[0436] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q10, and R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX1") wherein in Tables 1A to 6A the inventive compounds are designated by *). [Table 1][Table 1A]CF 3 CHF 2 CH 2 CF 3 CF 2 CF 3 CH 2 CF 2 CF 3 CF 2 CF 2 CF 3 CF 2 CF 2 CF 2 CF 3 CF 2 CF 2 CF 2 CF 2 CF 3 OCF 3 *)OCHF 2 *)OCH 2 CF 3 *)OCH 2 CHF 2 *)OCF 2 CF 3 *)OCH(CH 3 )CF 3 *)OCH 2 CF 2 CHF 2 *)OCH 2 CF 2 CF 3 *)OCF 2 CF 2 CF 3 *)OCH 2 CF 2 CHFCF 3 *)OCH 2 CF 2 CF 2 CF 3 *)OCF 2 CF 2 CF 2 CF 3 *)OCH 2 CF 2 CF 2 CF 2 CF 3 *)[Table 2A]SCF 3 SCH 2 CF 3 SCF 2 CF 3 SCH 2 CF 2 CF 3 SCF 2 CF 2 CF 3 SCH 2 CF 2 CF 2 CF 3 SCF 2 CF 2 CF 2 CF 3 S(O)CF 3 S(O)CH 2 CF 3 S(O)CF 2 CF 3 S(O)CH 2 CF 2 CF 3 S(O)CF 2 CF 2 CF 3 S(O)CH 2 CF 2 CF 2 CF 3 S(O)CF 2 CF 2 CF 2 CF 3 S(O) 2 CF 3 S(O) 2 CH 2 CF 3 S(O) 2 CF 2 CF 3 S(O) 2 CH 2 CF 2 CF 3 S(O) 2 CF 2 CF 2 CF 3 S(O) 2 CH 2 CF 2 CF 2 CF 3 S(O) 2 CF 2 CF 2 CF 2 CF 3 [Table 3A]NHCH 2 CF 3 NHCH 2 CF 2 CF 3 NHCH 2 CF 2 CF 2 CF 3 NMeCH 2 CF 3 NMeCH 2 CF 2C F 3 NMeCH 2 CF 2 CF 2 CF 3 NEtCH 2 CF 3 NEtCH 2 CF 2 CF 3 NEtCH 2 CF 2 CF 2 CF 3 OS(O) 2 CF 3 OS(O) 2 CF 2 CF 3 OS(O) 2 CF 2 CF 2 CF 3 CH 2 OCF 3 CH 2 OCH 2 CF 3 CH 2 OCF 2 CF 3 C (O)CF 3 C(O)CF 2 CF 3 C(O)CF 2 CF 2 CF 3 C(O)NMeCH 2 CF 3 NMeC(O)CF 3 N=CEtCH 2 CF 3

[0437] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX2") (not within the claims).

[0438] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX3") (not within the claims). The following compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0439] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< and R 5b< represent a hydrogen atom, and 'T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX4").

[0440] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX5").

[0441] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX6").

[0442] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX7").

[0443] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX8").

[0444] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX9").

[0445] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, and R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX10").

[0446] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX9").

[0447] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, and R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX12").

[0448] A compound wherein A 2< A 3< and A 4< represent CH, Q represents a group represented by Q11, and R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX13") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0449] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX14") (not within the claims).

[0450] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX15") (not within the claims). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0451] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX16").

[0452] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX17").

[0453] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX18").

[0454] A compound wherein A 3< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in (Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX19").

[0455] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX20").

[0456] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX21").

[0457] A compound wherein A 4< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX21").

[0458] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX22").

[0459] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX23").

[0460] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX24").

[0461] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< , R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX25") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0462] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX26") (not within the claims).

[0463] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX27") (not within the claims). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0464] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< , R 5a< and R 5b< represent a hydrogen atom and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX28").

[0465] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX29").

[0466] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX30").

[0467] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< , R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX31").

[0468] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX32").

[0469] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX33").

[0470] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< , R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX34").

[0471] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represent a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX35").

[0472] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represent a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX36").

[0473] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX37") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0474] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX38") (not within the claims).

[0475] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX39") (not within the claims).

[0476] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX40").

[0477] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX41").

[0478] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A} to [Table 6A] (hereinafter, referred to as "Compound class SX42").

[0479] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< and R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX43").

[0480] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX44").

[0481] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX45").

[0482] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX46").

[0483] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX47").

[0484] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX48").

[0485] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q13, R 3< and R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX49") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0486] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q13, R 3< and R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX50") (not within the claims). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0487] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q13, R 3< and R 5a< represents a hydrogen atom, and T represents any one substituent indicated in (Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX51").

[0488] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q13, R 3< and R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX52").

[0489] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q13, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX53") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0490] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q13, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX54").

[0491] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q13, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX55").

[0492] A compound wherein A 4< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q13, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX56").

[0493] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q14, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX57") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0494] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q14, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX58").

[0495] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q14, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX59").

[0496] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q14, R 5a< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX60").

[0497] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX61") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0498] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX62") (not within the claims).

[0499] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX63") (not within the claims).

[0500] A compound wherein A 4< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX64").

[0501] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX65").

[0502] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX66").

[0503] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX67").

[0504] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX68").

[0505] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX69").

[0506] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX70").

[0507] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX71").

[0508] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, R 5b< represents a fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX72").

[0509] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX73") wherein in Tables 1A to 6A the inventive compoundds are designated by *).

[0510] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX74") (not within the claims).

[0511] A compound wherein A 2< , A 3< , and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX75") (not within the claims). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0512] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX76").

[0513] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX77").

[0514] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX78").

[0515] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX79").

[0516] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX80").

[0517] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX81").

[0518] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX82") .

[0519] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX83").

[0520] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX84").

[0521] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX85") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0522] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX86") (not within the claims).

[0523] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX87 (not within the claims).

[0524] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX88").

[0525] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX89").

[0526] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX90)).

[0527] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX91").

[0528] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX92").

[0529] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX93").

[0530] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< and R 5b< represent a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX94").

[0531] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represent a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX95").

[0532] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represent a 4-fluorophenyl group, and T represents any one substituent indicated in [Table to [Table 6A] (hereinafter, referred to as "Compound class SX96").

[0533] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX97") wherein in Tables 1A to 6A the inventive compounds are designated by *).

[0534] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX98") (not within the claims).

[0535] A compound wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX99") (not within the claims).

[0536] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX100").

[0537] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX101").

[0538] A compound wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX102").

[0539] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX103").

[0540] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX104").

[0541] A compound wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX105").

[0542] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a hydrogen atom, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX106").

[0543] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a cyclopropyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX107").

[0544] A compound wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents a 4-fluorophenyl group, and T represents any one substituent indicated in [Table 1A] to [Table 6A] (hereinafter, referred to as "Compound class SX108").

[0545] A compound represented by formula (L-1): (hereinafter, referred to as "Compound (L-1)") wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX257") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0546] [Table 3] [Table 6][Table 14A]F *)Cl *)Br *)Me *)CF 3 *)OMe *)OEt *)OPr *)Oi-Pr *)NH2NHCH 2 CF 3 CNNHC(O)c-PrNMeC(O)c-PrCH=N-OHCH=N-OMeOPh *)O-2-F-Ph *)OPy2 *)OPy3 *)

[0547] The following compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0548] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX258").

[0549] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX259").

[0550] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX260").

[0551] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX261") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0552] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX262").

[0553] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX263").

[0554] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX264").

[0555] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 53< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX265") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0556] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 30< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX266").

[0557] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX267").

[0558] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX268").

[0559] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX269") wherein in Tables 7A to 14A the inventive compounds are designated by *). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0560] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX270").

[0561] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX271").

[0562] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX272").

[0563] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX273") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0564] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX274").

[0565] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX275").

[0566] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX276").

[0567] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX277") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0568] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX278").

[0569] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX279").

[0570] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX280").

[0571] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX281") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0572] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX282").

[0573] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX283") .

[0574] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX284"}.

[0575] The compound (L-1) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX285") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0576] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX286").

[0577] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX287").

[0578] The compound (L-1) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX288").

[0579] A compound represented by formula (L-2): (hereinafter, referred to as "Compound (L-23") wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX345") wherein in Tables 7Ato 14A the inventive compounds are designated by *). The following compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0580] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX346").

[0581] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX347").

[0582] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX348") .

[0583] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX349") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0584] The compound (L-1) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX350").

[0585] The compound (L-1) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX351") .

[0586] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX352").

[0587] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX353") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0588] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX354").

[0589] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX355").

[0590] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX356").

[0591] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX357") wherein in Tables 7A to 14A the inventive compounds are designated by *). As mentioned above, compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0592] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX358").

[0593] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX359").

[0594] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX360").

[0595] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX361") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0596] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX362").

[0597] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX363").

[0598] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX364").

[0599] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX365") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0600] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX366").

[0601] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX367").

[0602] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX368").

[0603] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX369") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0604] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX370") .

[0605] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX371").

[0606] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX372").

[0607] The compound (L-2) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX373") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0608] The compound (L-2) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX374") .

[0609] The compound (L-2) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX375").

[0610] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX376").

[0611] A compound represented by formula (L-3): (hereinafter, referred to as "Compound (L-3)") wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX433") wherein in Tables 7A to 14A the inventive compounds are designated by *). The following compounds wherein A 2< , A 3< , or A 4< is a nitrogen atom are not within the claims.

[0612] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX434").

[0613] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX435").

[0614] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX436").

[0615] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX437") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0616] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in (Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX438") .

[0617] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX439").

[0618] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q11, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX440").

[0619] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX441") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0620] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX442").

[0621] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX443").

[0622] The compound (L-2) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< and R 5a< represent a hydrogen atom, R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX444").

[0623] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX44 5") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0624] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX446").

[0625] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX447").

[0626] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q12, R 3< represents a methyl group, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX448").

[0627] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX449") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0628] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX450").

[0629] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX451").

[0630] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q15, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX452").

[0631] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX453") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0632] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX454").

[0633] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX455").

[0634] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q16, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX456").

[0635] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX457") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0636] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX458").

[0637] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX459") .

[0638] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a hydrogen atom, R 5< " represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX460") .

[0639] The compound (L-3) wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX461") wherein in Tables 7A to 14A the inventive compounds are designated by *).

[0640] The compound (L-3) wherein A 2< represents a nitrogen atom, A 3< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX462") .

[0641] The compound (L-3) wherein A 3< represents a nitrogen atom, A 2< and A 4< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX463") .

[0642] The compound (L-3) wherein A 4< represents a nitrogen atom, A 2< and A 3< represent CH, Q represents a group represented by Q17, R 3< represents a methyl group, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX464") .

[0643] A compound represented by formula (L-4): (hereinafter, referred to as "Compound (L-4)") wherein A 2< , A 3< and A 4< represent CH, Q represents a group represented by Q10, R 5a< represents a hydrogen atom, and R 5b< represents any one substituent indicated in [Table 7A] to [Table 14A] (hereinafter, referred to as "Compound class SX521") wherein in Tables 7A to 14A the inventive compounds are designated by *). The following compounds wherein A...

Claims

1. A compound represented by formula (I): wherein Q represents a group represented by formula Q1, n is 0, 1 or 2, R2 represents an ethyl group, Ya represents an oxygen atom, a sulfur atom, or NR3a, G1 represents a nitrogen atom, or CR5a, G2 represents a nitrogen atom, or CR5b, R3a represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a hydrogen atom, R5a and R5b are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR12, a halogen atom, or a hydrogen atom, A2 represents CH, A3 represents CH, A4 represents CH, T represents OR1, R1 represents a C1-C6 alkyl group which has one or more halogen atoms, R12 represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, a phenyl group which may optionally have one or more substituents selected from Group H, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group H, S(O)2R23, or a hydrogen atom, R23 represents a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, or a phenyl group which may optionally have one or more substituents selected from Group D, Group C: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, and a halogen atom, Group D: a group consisting of a C1-C6 chain hydrocarbon group which may optionally have one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a C3-C6 alkenyloxy group which may optionally have one or more halogen atoms, a C3-C6 alkynyloxy group which may optionally have one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfinyl group which may optionally have one or more halogen atoms, a C1-C6 alkylsulfonyl group which may optionally have one or more halogen atoms, an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom, R21 and R22 are identical to or different from each other, and each represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, Group F: a group consisting of a C1-C6 alkoxy group which may optionally have one or more halogen atoms, a phenyl group which may optionally have one or more substituents selected from Group D, a 5- or 6- membered aromatic heterocyclic group which may optionally have one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may optionally have one or more halogen atoms, a 3 to 7 membered nonaromatic heterocyclic group which may optionally have one or more substituents selected from Group C, an amino group, NHR21, NR21R22, and a cyano group, Group H: a group consisting of a C1-C6 alkyl group which may optionally have one or more halogen atoms, OR10, NR9R10, C(O)R10, C(O)NR9R10, OC(O)R9, OC(O)OR9, NR10C(O)R9, NR10C(O)OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6- membered aromatic heterocyclic group, R9 represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, or a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, and R10 represents a C1-C6 alkyl group which may optionally have one or more halogen atoms, a C3-C6 cycloalkyl group which may optionally have one or more halogen atoms, or a hydrogen atom.

2. The compound according to claim 1, wherein R1 represents a C1-C5 alkyl group having three or more fluorine atoms.

3. A composition for use in controlling a harmful arthropod comprising the compound according to claim 1 or 2 and an inert carrier.

4. A method for controlling a harmful arthropod which comprises applying an effective amount of the compound according to claim 1 or 2 to a harmful arthropod or a habitat where a harmful arthropod lives, wherein a method for the treatment of the human or animal body by therapy is excluded.

5. A composition comprising one or more ingredients selected from Group (a) and Group (b), and the compound according to claim 1 or 2: Group (a): a group consisting of insecticidal ingredients, miticide ingredients, and nematicidal ingredients; and Group (b): fungicidal ingredient.

6. A method for controlling a harmful arthropod which comprises applying an effective amount of the composition according to claim 5 to a harmful arthropod or a habitat where a harmful arthropod lives, wherein a method for the treatment of the human or animal body by therapy is excluded.

7. A seed or vegetative reproductive organ carrying an effective amount of the compound according to claim 1 or 2 or an effective amount of the composition according to claim 5.