Heterocyclic compound and harmful-arthropod-controlling agent containing same

Abstract

A compound represented by Formula (I) is provided. ##STR00001##
In Formula (I), Q represents a group represented by Formula Q1, Q2, or Q3, and T represents a chain hydrocarbon group, an alkoxyalkyl group, an alkylsulfanylalkyl group, an alkylsulfinylalkyl group, or an alkylsulfonylalkyl group, which has a halogen atom; a cycloalkylalkyl group or a cycloalkyl group, which has a substituent; OR.sup.1, S(O).sub.mR.sup.1, OS(O).sub.2R.sup.1, CH.sub.2OR.sup.1, NR.sup.1R.sup.29, C(O)R.sup.1, C(O)NR.sup.1R.sup.29, NR.sup.29C(O)R.sup.1, NCR.sup.1R.sup.30, or a group represented by any one of Formulas T-1 to T-12. ##STR00002## ##STR00003##

Claims

1. A compound represented by Formula (I): ##STR00237## in the formula, Q represents a group represented by Formula Q1, a group represented by Formula Q2, or a group represented by Formula Q3, ##STR00238## n represents 0, 1, or 2, G.sup.1 represents a nitrogen atom or CR.sup.3a, G.sup.2 represents a nitrogen atom or CR.sup.3b, G.sup.3 represents a nitrogen atom or CR.sup.3c, G.sup.4 represents a nitrogen atom or CR.sup.3d, R.sup.3a, R.sup.3b, R.sup.3c, and R.sup.3d each independently represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group E, a phenyl group optionally having one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group H, OR.sup.12x, NR.sup.11R.sup.12, NR.sup.11aR.sup.12a, NR.sup.29NR.sup.11R.sup.12, NR.sup.29OR.sup.11, NR.sup.11C(O)R.sup.13, NR.sup.29NR.sup.11C(O)R.sup.13, NR.sup.11C(O)OR.sup.14, NR.sup.29NR.sup.11C(O)OR.sup.14, NR.sup.11C(O)NR.sup.15xR.sup.16x, NR.sup.24NR.sup.11C(O)NR.sup.15xR.sup.16x, NCHNR.sup.15xR.sup.16x, NS(O).sub.xR.sup.15R.sup.16, C(O)OR.sup.17, C(O)R.sup.13, C(O)NR.sup.15xR.sup.16x, C(O)NR.sup.11S(O).sub.2R.sup.23, CR.sup.30NOR.sup.17, NR.sup.11CR.sup.24NOR.sup.17, a cyano group, a nitro group, a hydrogen atom, or a halogen atom, x represents 0 or 1, A.sup.1 represents NR.sup.5, an oxygen atom, or a sulfur atom, A.sup.2 represents a nitrogen atom or CR.sup.4a, A.sup.3 represents a nitrogen atom or CR.sup.4b, A.sup.4 represents a nitrogen atom or CR.sup.4c, R.sup.4a, R.sup.4b, and R.sup.4c each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a nitro group, OR.sup.18, NR.sup.18R.sup.19, a cyano group, or a halogen atom, T represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR.sup.1, S(O).sub.mR.sup.1, OS(O).sub.2R.sup.1, CH.sub.2OR.sup.1, NR.sup.1R.sup.29, C(O)R.sup.1, C(O)NR.sup.1R.sup.29, NR.sup.29C(O)R.sup.1, NCR.sup.1R.sup.30, 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, a group represented by Formula T-8, a group represented by Formula T-9, a group represented by Formula T-10, a group represented by Formula T-11, or a group represented by Formula T-12, ##STR00239## ##STR00240## X.sup.1 represents a nitrogen atom or CR.sup.1a, X.sup.2 represents a nitrogen atom or CR.sup.1b, X.sup.3 represents a nitrogen atom or CR.sup.1c, X.sup.4 represents a nitrogen atom or CR.sup.1d, X.sup.5 represents a nitrogen atom or CR.sup.1e, R.sup.1x represents OR.sup.7, OS(O).sub.2R.sup.7, S(O).sub.mR.sup.7, NR.sup.1R.sup.29, NR.sup.8S(O).sub.2R.sup.7, a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom, R.sup.1a, R.sup.1b, R.sup.1c, R.sup.1d, and R.sup.1e each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom, Y.sup.1 represents NR.sup.25, an oxygen atom, or a sulfur atom, Y.sup.2 represents a nitrogen atom or CR.sup.26, Y.sup.3 represents a nitrogen atom or CR.sup.27, Y.sup.4 represents a nitrogen atom or CR.sup.28, R.sup.5 and R.sup.25 each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, or a (C3-C7 cycloalkyl) C1-C6 alkyl group optionally having one or more halogen atoms, R.sup.26, R.sup.27, and R.sup.28 each independently represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom, R.sup.1y represents OR.sup.7, OS(O).sub.2R.sup.7, S(O).sub.mR.sup.7, NR.sup.8S(O).sub.2R.sup.7, a cyano group, a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom, R.sup.1ay and R.sup.7 each independently represents a C1-C6 chain hydrocarbon group having one or more halogen atoms, R.sup.8 represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, m represents 0, 1, or 2, R.sup.1 represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-05 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G, R.sup.2 represents a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6 alkyl group optionally having one or more halogen atoms, R.sup.11, R.sup.17, R.sup.19, R.sup.24, and R.sup.29 each independently represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.30 represents a hydrogen atom, a halogen atom, OR.sup.31, NR.sup.32R.sup.33, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.18 and R.sup.31 each independently represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.32 and R.sup.33 each independently represents a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.12 represents a hydrogen atom, S(O).sub.2R.sup.23, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a C1-C6 alkyl group having one substituent selected from Group F, R.sup.12x represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituents selected from Group J, a phenyl group, a 6-membered aromatic heterocyclic group, in which the phenyl group and the 6-membered aromatic heterocyclic group each independently optionally has one or more substituents selected from Group D, S(O).sub.2R.sup.23, or a hydrogen atom, R.sup.23 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D, R.sup.11a and R.sup.12a, together with the nitrogen atom to which R.sup.11a and R.sup.12a are bonded, represent a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group E, R.sup.13 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, R.sup.14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group, in which the phenyl moiety in the phenyl C1-C3 alkyl group optionally has one or more substituents selected from Group D, R.sup.15 and R.sup.16 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, R.sup.15x represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom, R.sup.16x represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, or a hydrogen atom, Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having 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 optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom, Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, NHR.sup.21, NR.sup.21R.sup.22, C(O)R.sup.21, OC(O)R.sup.21, C(O)OR.sup.21, a cyano group, a nitro group, and a halogen atom, in which R.sup.21 and R.sup.22 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having 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 optionally having one or more halogen atoms, an amino group, NHR.sup.21, NR.sup.21R.sup.22, a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group C, Group G: a group consisting of a halogen atom and a C1-C6 haloalkyl group, Group H: a group consisting of a halogen atom, a nitro group, a cyano group, an amino group, a 5- or 6-membered aromatic heterocyclic group, a C1-C6 alkyl group optionally having one or more halogen atoms, OR.sup.10, NR.sup.9R.sup.10, C(O)R.sup.10, C(O)NR.sup.9R.sup.10, OC(O)R.sup.9, OC(O)OR.sup.9, NR.sup.10C(O)R.sup.9, NR.sup.10C(O)OR.sup.9, and C(O)OR.sup.10, Group J: a group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a halogen atom, and a cyano group, R.sup.9 represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms, and R.sup.10 represents a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms.

2. The compound according to claim 1, which is represented by Formula (I): ##STR00241## in the formula, Q is a group represented by Formula Q1, a group represented by Formula Q2, or a group represented by Formula Q3, ##STR00242## n is 0, 1, or 2, G.sup.1 is a nitrogen atom or CR.sup.3a, G.sup.2 is a nitrogen atom or CR.sup.3b, G.sup.3 is a nitrogen atom or CR.sup.3c, G.sup.4 is a nitrogen atom or CR.sup.3d, R.sup.3a, R.sup.3b, R.sup.3c, and R.sup.3d are each independently a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group E, a phenyl group optionally having one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group H, OR.sup.12, NR.sup.11R.sup.12, NR.sup.11aR.sup.12a, NR.sup.29NR.sup.11R.sup.12, NR.sup.29OR.sup.11, NR.sup.11C(O)R.sup.13, NR.sup.29NR.sup.11C(O)R.sup.13, NR.sup.11C(O)OR.sup.14, NR.sup.29NR.sup.11C(O)OR.sup.14, NR.sup.11C(O)NR.sup.15R.sup.16, NR.sup.24NR.sup.11C(O)NR.sup.15R.sup.16, NCHNR.sup.15R.sup.16, NS(O).sub.xR.sup.15R.sup.16, C(O)OR.sup.17, a cyano group, a nitro group, a hydrogen atom, or a halogen atom, x is 0 or 1, A.sup.1 is NR.sup.5, an oxygen atom, or a sulfur atom, A.sup.2 is a nitrogen atom or CR.sup.4a, A.sup.3 is a nitrogen atom or CR.sup.4b, A.sup.4 is a nitrogen atom or CR.sup.4c, R.sup.4a, R.sup.4b, and R.sup.4c are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a nitro group, OR.sup.18, NR.sup.18R.sup.19, a cyano group, or a halogen atom, T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR.sup.1, S(O).sub.mR.sup.1, OS(O).sub.2R.sup.1, CH.sub.2OR.sup.1, NR.sup.1R.sup.29, C(O)R.sup.1, C(O)NR.sup.1R.sup.29, NR.sup.29C(O)R.sup.1, NCR.sup.1R.sup.30, 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, a group represented by Formula T-8, a group represented by Formula T-9, a group represented by Formula T-10, a group represented by Formula T-11, or a group represented by Formula T-12, ##STR00243## ##STR00244## X.sup.1 is a nitrogen atom or CR.sup.1a, X.sup.2 is a nitrogen atom or CR.sup.1b, X.sup.3 is a nitrogen atom or CR.sup.1c, X.sup.4 is a nitrogen atom or CR.sup.1d, X.sup.5 is a nitrogen atom or CR.sup.1e, R.sup.1x is OR.sup.7, OS(O).sub.2R.sup.7, S(O).sub.mR.sup.7, NR.sup.1R.sup.29, NR.sup.8S(O).sub.2R.sup.7, a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom, R.sup.1a, R.sup.1b, R.sup.1c, R.sup.1d, and R.sup.1e are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom, Y.sup.1 is NR.sup.25, an oxygen atom, or a sulfur atom, Y.sup.2 is a nitrogen atom or CR.sup.26, Y.sup.3 is a nitrogen atom or CR.sup.27, Y.sup.4 is a nitrogen atom or CR.sup.28, R.sup.5 and R.sup.25 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, or a (C3-C7 cycloalkyl) C1-C6 alkyl group optionally having one or more halogen atoms, R.sup.26, R.sup.27, and R.sup.28 are each independently a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a halogen atom, R.sup.1y is OR.sup.7, OS(O).sub.2R.sup.7, S(O).sub.mR.sup.7, NR.sup.8S(O).sub.2R.sup.7, a cyano group, a C1-C5 chain hydrocarbon group having one or more halogen atoms, or a halogen atom, R.sup.1ay and R.sup.7 are each independently a C1-C6 chain hydrocarbon group having one or more halogen atoms, R.sup.8 is a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, m is 0, 1, or 2, R.sup.1 is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G, R.sup.2 is a cyclopropyl group, a cyclopropylmethyl group, or a C1-C6 alkyl group optionally having one or more halogen atoms, R.sup.11, R.sup.17, R.sup.19, R.sup.24, and R.sup.29 are each independently a hydrogen atom, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.30 is a hydrogen atom, a halogen atom, OR.sup.31, NR.sup.32R.sup.33, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.18 and R.sup.31 are each independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.32 and R.sup.33 are each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R.sup.12 is a hydrogen atom, S(O).sub.2R.sup.23, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a C1-C6 alkyl group having one substituent selected from Group F, R.sup.23 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D, R.sup.11a and R.sup.12a, together with the nitrogen atom to which R.sup.11a and R.sup.12a are bonded, are a 3-to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group E, R.sup.13 is a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, R.sup.14 is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group, in which the phenyl moiety in the phenyl C1-C3 alkyl group optionally has one or more substituents selected from Group D, R.sup.15 and R.sup.16 are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having 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 optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, and a halogen atom, Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, an amino group, NHR.sup.21, NR.sup.21R.sup.22, C(O)R.sup.21, OC(O)R.sup.21, C(O)OR.sup.21, a cyano group, a nitro group, and a halogen atom, in which R.sup.21 and R.sup.22 each independently represents a C1-C6 alkyl group optionally having one or more halogen atoms, Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having 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 optionally having one or more halogen atoms, an amino group, NHR.sup.21, NR.sup.21R.sup.22, a cyano group, a phenyl group optionally having one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3- to 7-membered non-aromatic heterocyclic group optionally having one or more substituents selected from Group C, Group G: a group consisting of a halogen atom and a C1-C6 haloalkyl group, Group H: a group consisting of a halogen atom, a nitro group, a cyano group, an amino group, a 5- or 6-membered aromatic heterocyclic group, a C1-C6 alkyl group optionally having one or more halogen atoms, OR.sup.10, NR.sup.9R.sup.10, C(O)R.sup.10, C(O)NR.sup.9R.sup.10, OC(O)R.sup.9, OC(O)OR.sup.9, NR.sup.10C(O)R.sup.9, NR.sup.10C(O)OR.sup.9, and C(O)OR.sup.10, R.sup.9 is a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms, and R.sup.10 is a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a C3-C6 cycloalkyl group optionally having one or more halogen atoms.

3. The compound according to claim 1, wherein Q is a group represented by Formula Q1.

4. The compound according to claim 1, wherein A.sup.2 is CR.sup.4a and A.sup.4 is CR.sup.4c.

5. The compound according to claim 1, wherein A.sup.2 is CR.sup.4a, A.sup.3 is CR.sup.4b, and A.sup.4 is CR.sup.4c.

6. The compound according to claim 1, wherein A.sup.2 is CR.sup.4a, A.sup.3 is a nitrogen atom, and A.sup.4 is CR.sup.4c.

7. The compound according to claim 1, wherein T is a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, a C3-C7 cycloalkyl group having one or more substituents selected from Group G, OR.sup.1, S(O).sub.mR.sup.1, OS(O).sub.2R.sup.1, or NR.sup.1R.sup.29.

8. The compound according to claim 1, wherein T is OR.sup.1, and R.sup.1 is a C1-C5 alkyl group having three or more fluorine atoms.

9. The compound according to claim 1, wherein R.sup.3a, R.sup.3b, R.sup.3c, and R.sup.3d are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group, in which the phenyl group, the pyridyl group, the pyrimidinyl group, the pyrazolyl group, and the triazolyl group each independently optionally has one or more substituents selected from Group H, an amino group, NR.sup.11C(O)OR.sup.14, a hydrogen atom, or a halogen atom, and R.sup.4a and R.sup.4c are hydrogen atoms.

10. The compound according to claim 1, wherein G.sup.1 and G.sup.4 are CH's, G.sup.2 is CR.sup.3b, G.sup.3 is CR.sup.3c, R.sup.3b and R.sup.3c are each independently a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom, and R.sup.4a and R.sup.4c are hydrogen atoms.

11. The compound according to claim 1, wherein R.sup.2 is an ethyl group.

12. A harmful-arthropod-controlling composition, comprising: the compound according to claim 1; and an inactive carrier.

13. A method for controlling a harmful arthropod, comprising: applying an effective amount of the compound according to claim 1 to the harmful arthropod or a habitat of the harmful arthropod.

14. A composition comprising: one or more ingredients selected from the group consisting of Group (a), Group (b), Group (c), and Group (d); and the compound according to claim 1, Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients, Group (b): fungicidal active ingredients, Group (c): plant growth-regulating ingredients and Group (d): phytotoxicity-decreasing ingredients.

Description

EXAMPLES

(1) Hereinafter, the present invention will be described in more detail by way of production examples, formulation examples, test examples, and the like. However, the present invention is not limited to only these examples.

(2) First, production examples of the present compound are shown.

(3) LC-MS Analysis Conditions

(4) Measurement Condition A

(5) LCMS: ColumnZorbax Extend C18 (504.6 mm, 5 u, 80 A), (mobile phase: from 90% [10 mM NH.sub.4OAc in water] and 10% [CH.sub.3CN] to 70% [10 mM NH.sub.4OAc in water] and 30% [CH.sub.3CN] in 1.5 min, further to 10% [10 mM NH.sub.4OAc in water] and 90% [CH.sub.3CN] in 3.0 mm, held this mobile phase composition up to 4.0 min and finally back to initial condition in 5.0 min). Flow=1.2 ml/min

(6) Measurement Condition B

(7) ColumnX-Bridge C18 (504.6 mm, 5 u), (mobile phase: from 90% [10 mM NH.sub.4OAc in water] and 10% [CH.sub.3CN] to 70% [10 mM NH.sub.4OAc in water] and 30% [CH.sub.3CN] in 1.5 min, further to 10% [10 mM NH.sub.3OAc in water] and 90% [CH.sub.3CN] in 3.0 min, held this mobile phase composition up to 4.0 min and finally back to initial condition in 5.0 min). Flow=1.2 ml/min

(8) Measurement Condition C

(9) L-Column2 ODS (354.6 mm), (mobile phase: front 90% [0.1% HCOOH in water] and 10% [0.1% HCOOH in CH.sub.3CN] to 100% [0.1% HCOOH in CH.sub.3CN] in 2.0 min, held this mobile phase composition up to 4.0 min and finally back to initial condition in 5.0 min). Flow=1.0 ml/min

(10) Measurement Condition D

(11) LCMS: ColumnYMC-TRIART C18 (332.1 min, 3 u), (mobile phase: 98% [0.05% HCOOH in water] and 2% [CH.sub.3CN] held for 0.75 min, then to 90% [0.05% HCOOH in water] and 10% [CH.sub.3CN] in 1.0 min, further to 2% [0.05% HCOOH in water] and 98% [CH.sub.3CN] in 2.0 min, held this mobile phase composition up to 2.25 min and finally back to initial condition in 3.0 min). Flow=1.0 ml/min.

Reference Production Example 1

(12) To a mixture of 20 g of 2-cyano-5-(2,2,3,3-pentafluoropropoxy)pyridine and 200 mL of THF was added dropwise 87 mL of methylmagnesium bromide under ice-cooling, and the mixture was stirred for 30 minutes. To this mixture was added 50 mL of 1 N hydrochloric acid, and the mixture was stirred for 1 hour. The mixture was extracted with MTBE and the obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 20 g of Intermediate 2 represented by the following formula.

(13) ##STR00152##

(14) Intermediate 2: .sup.1H-NMR (CDCl.sub.3) : 8.39 (1H, d), 8.08 (1H, t), 7.34 (1H, dd), 4.55 (2H, td), 2.70 (3H, s).

Reference Production Example 2

(15) To a mixture of 17.5 g of intermediate 2 and 50 mL of acetic acid was added 3 mL of an acetic acid solution of 25% hydrogen bromide at room temperature, and then 3.6 mL of bromine was added thereto. The mixture was stirred at 100 C. for 1 hour. The mixture was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure, to obtain 14 g of Intermediate 3 represented by the following formula.

(16) ##STR00153##

(17) Intermediate 3: .sup.1H-NMR (CDCl.sub.3) : 8:40 (1H, d), 8.14 (1H, d), 7=37 (1H, dd), 4.80 (2H, s), 4.56 (2H, t).

Reference Production Example 3

(18) To a mixture of 2.2 g of Intermediate 3 and 5 mL of acetonitrile was added 0:9 g of 5-(trifluoromethyl)-2-aminopyridine at room temperature, and the mixture was refluxed for 3 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.43 g of Intermediate 4 represented by the following formula.

(19) ##STR00154##

(20) Intermediate 4: .sup.1H-NMR (CDCl.sub.3) : 8.52 (1H, t), 8.40 (1H, d), 8.27 (1H, d), 8.18 (1H, d), 7.73 (1H, dd), 2.38 (1H, dd), 7.37-7.33 (1H, dd), 4.53 (2H, td).

Reference Production Example 4

(21) Compounds produced according to the method described in Reference Production Example 3 and physical property values thereof are shown below.

(22) Compounds represented by Formula (A-1) in which a combination of T, G.sup.1, G.sup.2, G.sup.3 and G.sup.4 is any one of the combinations described in Table 16.

(23) ##STR00155##

(24) TABLE-US-00016 TABLE 16 Intermediate T G.sup.1 G.sup.2 G.sup.3 G.sup.4 5 OCH.sub.2CF.sub.2CF.sub.3 CH CH CCF.sub.3 CH 8 OCH.sub.2CF.sub.2CF.sub.3 CH CH CH CH 24 OCH.sub.2CF.sub.2CF.sub.3 N CCF.sub.3 CH CH 25 OCH.sub.2CF.sub.2CF.sub.3 CH CCF.sub.3 CH N 26 OCH.sub.2CF.sub.2CF.sub.3 CH CH CCF.sub.3 N 27 OCH.sub.2CF.sub.2CF.sub.3 CH CH CBr CH 62 OCH.sub.2CF.sub.2CF.sub.3 CH CBr CH CH 63 OCH.sub.2CF.sub.2CF.sub.3 CH CH CCl N

(25) Intermediate 5: .sup.1H-NMR (CDCl.sub.3) : 8.39 (1H, d), 8:29 (Hi s), 8.26 (1H, d), 8.20 (1H, d), 7.95 (1H, d), 7.39 (1H, dd), 6.99 (1H, dd), 4.53 (2a td).

(26) Intermediate 8: .sup.1H-NMR (CDCl.sub.3) : 8.37 (1H, d), 8.17 (3H, dt), 7.63 (1H, d), 7.36 (1H, td), 7.20 (1H, t), 6.81 (1H, t), 4:52 (2H, t).

(27) Intermediate 24: .sup.1H-NMR (CDCl.sub.3) : 4.52 (2H, t), 7.32-7.39 (2H, m), 8.08-8.19 (2H, m), 8.42 (1H, d), 8.64 (1H, s).

(28) Intermediate 25: .sup.1H-NMR (CDCl.sub.3) : 4.52 (2H, t), 7.37-7.39 (1H, m), 8.26 (1H, s), 8:33 (1H, d), 838 (1H, s), 8.71 (1H, s), 8.99 (1H, s).

(29) Intermediate 26-.sup.1H-NMR (CDCl.sub.3) : 4:52 (2111), 7.21 (ill s), 7.39 (1H, d), 8:314.38 (3H, m), 8.63 (1 Hid),

(30) Intermediate 27: .sup.1H-NMR (CDCl.sub.3) : 4.50 (2H, t), 6.90 (1H, d), 7.35 (1H, d), 7.79 (1H, s), 8.00 (1H, d), 8.11-8.13 (2H, m), 8.36 (1H, s).

(31) Intermediate 62: .sup.1H-NMR (CDCl.sub.3) : 4.43-4.79 (2H, m), 7.20-7.25 (1H, m), 7.35 (1H, dd), 7.48-7.52 (1H, m), 8.12 (2H, t), 8.29 (1H, s), 836 (1H, d).

(32) Intermediate 63: .sup.1H-NMR (CDCl.sub.3) : 4.51 (2H, f), 6.90 (1H, d), 7.36 (1H, d), 8.11 (1H, s), 8.26-8.28 (1H, m), 8.36-8.40 (2H, m).

Reference Production Example 5

(33) To a mixture of 0.79 g of Intermediate 4 and 7 mL of DMF was added 0.52 g of N-iodosuccinimide under, ice-cooling, and the mixture was stirred at room temperature for 12 hours. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.94 g of intermediate 6 represented by the following formula.

(34) ##STR00156##

(35) Intermediate 6: .sup.1H-NMR (CDCl.sub.3) : 8.67 (1H, d), 8.52 (1H, d), 8.24 (1H, d), 7.72 (1H, d), 7.43 (1H, t), 7.40 (1H, t), 4.55 (2H, t),

Reference Production Example 6

(36) Compounds produced according to foe method described in Reference Production Example 5 and physical property values thereof are shown below.

(37) ##STR00157##

(38) Compounds represented by Formula (A-2) in which a combination of T, X.sup.b, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 17.

(39) TABLE-US-00017 TABLE 17 Intermediate T X.sup.b G.sup.1 G.sup.2 G.sup.3 G.sup.4 7 OCH.sub.2CF.sub.2CF.sub.3 I CH CH CCF.sub.3 CH 9 OCH.sub.2CF.sub.2CF.sub.3 I CH CH CH CH 31 OCH.sub.2CF.sub.2CF.sub.3 I N CCF.sub.3 CH CH 32 OCH.sub.2CF.sub.2CF.sub.3 I CH CCF.sub.3 CH N 33 OCH.sub.2CF.sub.2CF.sub.3 I CH CH CCF.sub.3 N 34 OCH.sub.2CF.sub.2CF.sub.3 I CH CH CBr CH 35 OCH.sub.2CF.sub.2CF.sub.3 I CH CCH.sub.3 CH CH 36 OCH.sub.2CF.sub.2CF.sub.3 I CH CH CH 37 OCH.sub.2CF.sub.2CF.sub.3 I CH CH Cc-Pr CH 64 OCH.sub.2CF.sub.2CF.sub.3 I CH CH COCH.sub.3 N

(40) Intermediate 7: .sup.1H-NMR (CDCl.sub.3) :8.51 (1H, d), 8.43 (1H, d), 8.25 (1H, d), 7.93 (1H, d), 7.41 (1H, dd), 7.12 (1H, dd), 4.56 (2H, t).

(41) Intermediate 9: .sup.1H-NMR (CDCl.sub.3) : 8.50 (1H, d) 8.31 (1H, dd), 8.23 (1H, d), 7.62 (1H, t), 7.39 (1H, dd), 7.29 (1H, ddd), 6.96 (1H, td, J=6.8), 4.54 (2H, dd).

(42) Intermediate 31: .sup.1H-NMR (GDCl.sub.3) : 4.55 (2H, t), 7.39-7.42 (2H, m), 8.08 (1H, d), 8.28 (1H, d), 8.54 (1H, d).

(43) Intermediate 32: .sup.1H-NMR (CDCl.sub.3) : 4.54 (2H, t), 7.40 (1H, d) 8.40 (1H, d), 8.50 (1H, s), 8.71 (1H, s), 8.88 (1H, s).

(44) Intermediate 33: .sup.1H-NMR (CDCl.sub.3) : 5.07 (2H, t), 7.57 (1H, d) 7.73 (1H, d), 8.24 (1H, d), 8.59 (1H, s), 9.14 (1H, d).

(45) Intermediate 34: .sup.1H-NMR (CDCl.sub.3) : 4.53 (2H, t), 7.02 (1H, d), 7.35-7.38 (1H, m), 7.79 (1H, s), 8.15-8.20 (2H, m), 8.48 (1H, s).

(46) Intermediate 35: LCMS (measurement condition B): RT=3:39 min (260 nm), MS found: 548:3 [M+H].

(47) Intermediate 36: LCMS (measurement condition A): RT=3.76 min (260 nm), MS found: 483.8 [M+H].

(48) Intermediate 37: LCMS (measurement condition B): RT=3:93 min (260 nm) MS found: 509.6 [M+H].

(49) Intermediate 64: LCMS (measurement condition A): RT=3:50 min (260 nm), MS found: 500.8 [M+H],

(50) Intermediate 18 represented by tire following formula

(51) ##STR00159##

(52) Intermediate 18: .sup.1H-NMR (CDCl.sub.3) : 8.48 (1H, d), 8.44 (1H, d), 7.90-7.83 (2H, m), 7.49-7.38 (3H, m), 4.55 (2H, t).

(53) Intermediate 19 represented by die following formula

(54) ##STR00160##

(55) Intermediate 19: .sup.1H-NMR (CDCl.sub.3) : 8.99 (1H, d), 8.64 (1H, s), 8.35 (1H, d), 7.73 (1H, d), 7.43 (1H, dd), 4.04 (3H, s),

Reference Production Example 7

(56) To a mixture of 11.4 g of Intermediate 3, 15 g of potassium carbonate, and 130 mL of THF was added dropwise 3.2 mL of ethanethiol, and the mixture was stirred for 4.5 hours. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The Obtained residue was subjected to silica-gel column chromatography to obtain 9.57 g of Intermediate 10 represented by the following formula.

(57) ##STR00161##

(58) Intermediate 10: (CDCl.sub.3) : 8.39 (1H, d) 8.13 (1H, d), 7.36 (1H, dd), 4:55 (2H, td), 4.01 (2H, s) 2.60 (2H, q), 1.27 (3H, f).

Reference Production Example 8

(59) Compounds produced according to the method described in Reference Production Example 7 and physical property values thereof are shown below.

(60) Intermediate 11 represented by the following formula

(61) ##STR00162##

(62) Intermediate 11: .sup.1H-NMR (CDCl.sub.3) :8.73 (1H, t), 7.98 (2H, d), 4.00 (2H, t), 2.58 (2H, q), 1.27 (3H, t).

Reference Production Example 9

(63) To a mixture of 9.57 g of Intermediate 10, 4.5 mL of triethylamine, and 150 mL of chloroform was added dropwise 5.5 mL of trimethylsilyl triflate which had been cooled to 20 C., and the mixture was stirred at room temperature for 30 minutes. The mixture was brought to 20 C., 11.5 g of trimethylphenyl tribromide was added thereto and the mixture was stirred at room temperature for 2 hours. To this mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure, to obtain 14 g of intermediate 12 represented by the following formula.

(64) ##STR00163##

(65) Intermediate 12: .sup.1H-NMR (CDCl.sub.3) : 8.39 (1H, dd), 8.18 (1H, dd), 7.40-7.36 (1H, m), 6.15 (1H, s), 4.56 (2H, td), 2.71 (2H, dtt), 1.27 (3H, t).

Reference Production Example 10

(66) Compounds produced according to the method described in Reference Production Example 9 and physical property values thereof are shown below.

(67) Intermediate 13 represented by the following formula

(68) ##STR00164##

(69) Intermediate 13: .sup.1H-NMR (CDCl.sub.3) : 8.74 (1H, dd), 8.04 (2H, s), 7.19 (1H, s), 2.94-2.77 (2H, m), 1.35 (3H, t).

Reference Production Example 11

(70) Compounds produced according to the method described in Reference Production Example 3 and physical property val ties thereof are shown below.

(71) Intermediate 14 represented by the following formula

(72) ##STR00165##

(73) Intermediate 14: .sup.1H-NMR (CDCl.sub.3) : 8.90 (2H, % 8.31 (1H, d), 195 (1H, ddz), 7.78 (1H, d), 7.45 (1H, dd), 2.92 (2H, q), 1.16 (3H, t).

(74) Intermediate 15 represented by the following formula

(75) ##STR00166##

(76) Intermediate 15: .sup.1H-NMR (CDCl.sub.3) : 8.93 (1H, d), 8.52 (1H, s), 8.23 (2H, t), 7:74 (1H, d), 7.35 (1H, dd), 4.04 (3H, s).

Reference Production Example 12

(77) To a mixture of 0.8 g of Intermediate 14 and 8 mL of chloroform was added 1.03 g of 70% mCPBA under ice-cooling, and the mixture was stirred at room temperature for 6 hours. To the mixture were added a saturated sodium hydrogen carbonate aqueous solution and a sodium thiosulfate aqueous solution, and the mixture was extracted with chloroform. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.56 g of Intermediate 16 represented by the following formula.

(78) ##STR00167##

(79) Intermediate 16: .sup.1H-NMR (CDCl.sub.3) : 9.67 (1H, s), 8.78 (1H, t), 8.01 (2H, dd), 7.87 (1H, d), 7.63 (1H, dd), 3.99 (2H, q), 1.42 (3H, t),

Reference Production Example 13

(80) A mixture of 0.77 g of 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)pyridine, 0.2 g of [1,1-bis(diphenylphosphino)ferrocene]palladium (II) dichloride, 1.6 g of tripotassium phosphate, 0.67 g of benzo[b]thiophen-2-ylboronic acid, 0.5 ml of water, and 5 ml of DME was stirred under a nitrogen atmosphere at 85 C. for 3 hours. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over, sodium sulfate and concentrated under reduced pressure, the obtained residue was subjected to silica gel column chromatography to obtain 0.586 g of Intermediate 17 represented by the following formula.

(81) ##STR00168##

(82) Intermediate 17: .sup.1H-NMR (CDCl.sub.3) : 8.38 (1H, d), 7.86 (1H, dd), 7.79 (1H, q), 7.74 (1H, s), 7.38-7:32 (4H, m), 4.52 (2H, dd).

Reference Production Example 14

(83) A mixture of 3.0 g of Intermediate 19, 10 mL of 1,4-dioxane, 1:3 g of tris(dibenzylideneacetone)dipalladium (0), 1.7 g of xantphos, 3.7 mL of diisopropylethylamine, and 0.81 mL of ethanethiol was stirred, under reflux for 90 minutes. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate; and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.85 g of Intermediate 20 represented by the following formula.

(84) ##STR00169##

(85) Intermediate 20: .sup.1H-NMR (CDCl.sup.3) :9.17 (1H, d), 8.92 (1H, s), 8.41 (1H, d), 7.79 (1H, d), 7.45 (1H, dd), 4.06 (3H, s), 2.87 (2H, q), 1.18 (3H, t).

Reference Production Example 15

(86) A mixture of 0.85 g of Intermediate 20 and 20 ML of 12 N hydrochloric acid was stirred at 80 C. for 1 hour. The mixture was allowed to cool to room temperature, alkalified by adding a saturated sodium hydrogen carbonate aqueous solution, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain 1.28 g of crude product of intermediate 21 represented by the following formula.

(87) ##STR00170##

(88) Intermediate 21: .sup.1H-NMR (CDCl.sub.3) : 10.60 (1H, br s), 8.88 (1H, s), 8.43 (1H, s), 8.09 (1H, s), 7.74 (1H, d), 7.45 (1H, d), 2.86 (2H, d), 1.19 (3H, t),

Reference Production Example 16

(89) A mixture of 1.28 g of the crude product of Intermediate 21 obtained in Reference Production Example 15, 5 mL of phosphorus oxychloride, and 10 mL of toluene was stirred at 100 C. for 2 hours. The obtained mixture was allowed to cool to room temperature and concentrated under reduced pressure. To the obtained residue was added water, and the mixture was extracted with chloroform. The Obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain 0.74 g of Intermediate 22 represented by the following formula.

(90) ##STR00171##

(91) Intermediate 22: .sup.1H-NMR (CDCl.sub.3) : 9.42 (1H, d), 8.94 (1H, s), 8.76 (1H, d), 7.81 (1H, d), 7.49 (1H, dd), 2.92 (2H, q), 1.19 (3H, t).

Reference Production Example 17

(92) Intermediate 23 represented by the following formula was obtained according to the method described in Reference Production Example T2, using Intermediate 22 in place of intermediate 14.

(93) ##STR00172##

(94) Intermediate 23: .sup.1H-NMR (CDCl.sub.3) : 9.64 (1H, t), 9.13 (1H, t), 8.68 (1H, d), 7.91 (1H, d), 7.67 (1H, dd), 3.89 (2H, q), 1.43 (3H, t).

Reference Production Example 18

(95) Under a nitrogen atmosphere, a mixture of 509 mg of Intermediate 16, 400 mg of bis(pinacolato)diboron, 100 mg of [1,1-bis(diphenylphosphino)]palladium dichloride, 340 mg of potassium acetate, and 5 mL of dioxane was, stirred at 80 C. for 1 hour. The obtained mixture was allowed to cool to room temperature and concentrated under reduced pressure. To the obtained residue were added 5 mL of acetone and 2 mL of water, and 1.44 g of oxone was added thereto under ice-cooling. The obtained mixture was stirred at room temperature for 3 hours. To the obtained mixture was added saturated saline, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain 0.5 g of Intermediate 38 represented by the following formula, as a crude product.

(96) ##STR00173##

(97) Intermediate 38 LCMS (measurement condition C): RT+1:63 min (252 nm) MS found: 372.6 [M+H].

Reference Production Example 19

(98) A mixture of 1.0 g of Intermediate 62, 274 mg of tetrakis(triphenylphosphine)palladium, 753 mg of sodium carbonate, 437 mg of pyrimidin-5-ylboronic acid, 4 mL of water, and 16 mL of 1,4-dioxane was stirred at 100 C. for 16 hours under a nitrogen atmosphere. To the obtained mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to alumina column chromatography/to obtain 700 mg of Intermediate 28 represented by the following formula:

(99) ##STR00174##

(100) Intermediate 28: .sup.1H-NMR (CDCl.sub.3) : 5.02 (2H, t, J=13.6 Hz), 7.55-7.68 (2H, m, 7.76 (2H, S), 8.12 (1H, d, J=8.6 Hz), 8.43 (2H, d, J=17.2 Hz), 9.15-9.22 (3H, m).

Reference Production Example 20

(101) Compounds produced according to the method described in Reference Production Example 19 and physical property values thereof are shown below. Compounds represented by Formula (A-1) in which a combination of T, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 18.

(102) TABLE-US-00018 TABLE 18 Intermediate T G.sup.1 G.sup.2 G.sup.3 G.sup.4 29 OCH.sub.2CF.sub.2CF.sub.3 CH CCH.sub.3 CH CH 30 OCH.sub.2CF.sub.2CF.sub.3 CH CH Cc-Pr CH

(103) Intermediate 29: LCMS (measurement condition 8): RT=3:43 min (260 nm), MS found: 357.8 [M+H].

(104) Intermediate 30:1 CMS (measurement condition B): RT=3.57 min (260 nm). MS found: 383.7 [M+H],

Reference Production Example 21

(105) Compounds produced according to the method described in Reference Production Example 3 and physical property values thereof are shown below.

(106) Compounds represented by Formula (A-#) in which a combination of G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 19.

(107) ##STR00175##

(108) TABLE-US-00019 TABLE 19 Intermediate G.sup.1 G.sup.2 G.sup.3 G.sup.4 39 CH CH CH CH 40 CH CCF.sub.3 CH CH 66 N CCF.sub.3 CH CH

(109) Intermediate 39: .sup.1H-NMR (CDCl.sub.3) : 6.83 (1H, t), 7.20 (1H, t), 7.68 (1H, d), 8.14 (1H, d), 8.34 (1H, s), 8.84 (2H, s).

(110) Intermediate 40: .sup.1H-NMR (CDCl.sub.3) : 7.36 (1H, d), 7.80 (1H, d), 8.45 (1H, s), 8.53 (1H, s), 8.87 (2H, s).

(111) Intermediate 66: .sup.1H-NMR (CDCl.sub.3) : 7.38 (1H, d), 8.19 (1H, d), 8.82 (1H, s), 8.91 (2H, s).

Reference Production Example 22

(112) Compounds produced according to the method described in Reference Production Example 19 and physical property values thereof are shown, below.

(113) Compounds represented by Formula (A-9) in which a combination of T, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 20.

(114) ##STR00176##

(115) TABLE-US-00020 TABLE 20 Intermediate T G.sup.1 G.sup.2 G.sup.3 G.sup.4 41 CH CH CH CH 42 CH CH CH CH 43 CH CCF.sub.3 CH CH 44 0 CH CCF.sub.3 CH CH

(116) Intermediate 41: .sup.1H-NMR (CDCl.sub.3) : 7.31-7.34 (1H, m), 7.46-7.54 (4H, m), 7.61 (1H, d), 7.77 (1H, d), 8:48-8.53 (2H, m), 9.01 (2H, s).

(117) Intermediate 42: .sup.1H-NMR (CDCl.sub.3) : 7.36-7.40 (2H, m), 7.54-7.59 (2H, m), 8.53-8.56 (2H, m), 8.77 (2H, d), 9.09 (2H, s).

(118) Intermediate 43: .sup.1H-NMR(CDCl.sub.3) : 735-7.38 (1H, dd), 7.65-7.69 (1H, m), 7.72-7.74 (1H, m), 7.76-7.89 (3H, m), 8.52 (1H, s), 8.56 (1H, s), 9.05 (2H, s).

(119) Intermediate 44: .sup.1H-NMR (CDCl.sub.3) : 7.38 (1H, m), 7.54-7.59 (1H, m), 7:83 (1H, d), 8.15 (1H, s), 8.54-8.57 (2H, m), 8.99 (1H, s), 9.08 (2H, s).

Reference Production Example 23

(120) To a mixture of 900 mg of intermediate 39, 883 mg of 3-(trifluoromethyl)imidazole, and 10 mL of DMF were added sequentially 3.2 g of cesium carbonate, 0.1 mL of trans-N,N-dimethylcyclohexane-1,2-diamine, and 0.125 g of copper iodide, and the mixture was stirred at 140 C. for 24 hours. The mixture was cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to alumina chromatography (hexane:ethyl acetate=3:2) to obtain 700 mg of intermediate 45 represented by the following formula.

(121) ##STR00181##

(122) Intermediate 45: .sup.1H-NMR (CDCl.sub.3) : 6:83-6.87 (2H, m), 7.25 (1H, s) 7.71 (1H, d, J=9.2 Hz), 8.05 (1H, s), 8.17 (1H, d, J=6.4 Hz), 8.41 (1H, s), 9.18 (2H, s).

Reference Production Example 24

(123) Compounds produced according to the method described in Reference Production Example 23 and physical properly values thereof are shown below.

(124) Compounds represented by Formula (A-9) in which a combination off. G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 21,

(125) TABLE-US-00021 TABLE 21 Intermediate T G.sup.1 G.sup.2 G.sup.3 G.sup.4 46 CH CCF.sub.3 CH CH

(126) Intermediate 46: .sup.1H-NMR (CDCl.sub.3) :6.84 (1H, s), 7.38 (1H, d), 7.82 (1H, d), 8.07 (1H, s), 8.54 (2H, d), 9.22 (2H, s).

Reference Production Example 25

(127) A mixture of 2.5 g of Intermediate 40, 10=9 mL of 2,2,3,3,3-pentafluoropropanol, 692 mg of copper iodide, 1.3 g of 1,10-phenanthroline, 11.8 g of cesium carbonate, and 50 mL of xylene was stirred at 110 C. for 16 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.2 g of Intermediate 47 represented by the following formula.

(128) ##STR00183##

(129) Intermediate 47: .sup.1H-NMR (CDCl.sub.3) :4.58 (2H, t, J=11.6 Hz), 7.35 (1H, d, J=9.2 Hz), 7.80 (1H, d, J=9.3 Hz), 8:38 (1H, s), 853-8.56 (3H, m).

Reference Production Example 26

(130) Compounds produced according to the method described in Reference Production Example 25 and physical property values thereof are shown below.

(131) Compounds represented by Formula (A-9) in which a combination of T, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 22.

(132) TABLE-US-00022 TABLE 22 Intermediate T G.sup.1 G.sup.2 G.sup.3 G.sup.4 48 OCH.sub.2CF.sub.2CF.sub.3 N CCF.sub.3 CH CH

(133) Intermediate 48: .sup.1H-NMR (CDCl.sub.3) : 4.59 (2H, t), 7.36 (1H, d), 8.18 (1H, d). 8.59 (1H, s), 8.77 (2H, s).

Reference Production Example 27

(134) Compounds produced according to the method described in Reference Production Example 5 and physical property values thereof are shorn below.

(135) Compounds represented by Formula (A-10) in which a combination of T, X.sup.b, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 23.

(136) ##STR00184##

(137) TABLE-US-00023 TABLE 23 Intermediate T X.sup.b G.sup.1 G.sup.2 G.sup.3 G.sup.4 49 I CH CH CH CH 50 I CH CH CH CH 51 I CH CCF.sub.3 CH CH 52 I CH CCF.sub.3 CH CH 53 I CH CCF.sub.3 CH CH 54 0 I CH CCF.sub.3 CH CH 55 OCH.sub.2CF.sub.2CF.sub.3 I CH CCF.sub.3 CH CH 56 OCH.sub.2CF.sub.2CF.sub.3 I N CCF.sub.3 CH CH

(138) Intermediate 49: .sup.1H-NMR (CDCl.sub.3) : 7.43-7.56 (4H, m), 7.66 (2H, d), 7.82 (1H, d), 8.71 (1H, s), 9.14 (2H, s).

(139) Intermediate 50: .sup.1H-NMR (CDCl.sub.3) : 7.67 (1H, d), 7.91 (1H, d), 7.98 (2H, d), 8.74-8.79 (3H, m), 9.45 (2H, s).

(140) Intermediate 51: .sup.1H-NMR (CDCl.sub.3) : 7.45 (1H, d), 7:68-7.70 (1H, m), 7.73 (1H, s), 7.84 (2H, s), 7.89 (1H, s) 8.72 (1H, s), 9.15 (2H, s).

(141) Intermediate 52: .sup.1H-NMR (CDCl.sub.3) : 7.46-7.48 (1H, m), 7.83 (1H, s), 8.02 (1H, s), 8.18 (1H, s), 8.72 (1H, m), 9.01 (1 If, s)>9.12<1H, s), 9.17 (1H, s).

(142) Intermediate 53: .sup.1H-NMR (CDCl.sub.3) : 6.81-6.84 (1H, m), 6.99 (1H, t), 7.32 (1H, t), 7.72 (1H, d), 8.08 (1H, s), 835 (1H, d), 9.29 (2H, s).

(143) Intermediate 54: .sup.1H-NMR (CDCl.sub.3) : 6.85 (1H, s), 7.45-7.50 (1H, m), 7.82 (1H, d), 8.09 (1H, s), 8.71 (1H, s), 9.28-9.33 (2H, s).

(144) Intermediate 55: .sup.1H-NMR (CDCl.sub.3) : 4.60 (2H, t), 7.43 (1H, d), 7.79<1H, d), 8.67-8.68 (3H, m).

(145) Intermediate 56: .sup.1H-NMR (CDCl.sub.3) : 4.61 (2H, t), 7.43 (1H, d), 8.11 (1H, d), 8.67 (2H, s).

Reference Production Example 28

(146) Intermediate 57 represented by the following formula was obtained according to the method described in Reference Production Example 3, using 6-methoxypyridazin-3-amine in place of Intermediate 3.

(147) ##STR00191##

(148) Intermediate 57: .sup.1H-NMR (CDCl.sub.3) : 7.08 (1H, d), 736 (1H d), 7.73 (1H, d), 8.12 (1H, s), 8.16 (1H, d), 8.52 (1H, s), 10.93 (1H, brs).

Reference Production Example 29

(149) Intermediate 58 represented by die following formula was obtained according to the method described in Reference Production Example 5, using intermediate 57 in place of Intermediate 4.

(150) ##STR00192##

(151) Intermediate 58: .sup.1H-NMR (DMSO-d.sub.6) :1.94 (1H, d), 7.64 (1H, d), 7:86 (1H, d), 8.11 (1H, d), 8.70 (1H, br s), 13.38 (1H, brs).

Reference Production Example 30

(152) Intermediate 59 represented by the following formula was obtained according td the method described in Reference Production Example 14, using Intermediate 58 in place of Intermediate 19,

(153) ##STR00193##

(154) Intermediate 59: LCMS (measurement condition D): RT=1.64 min (260 nm), MS found: 341 [M+H],

(155) Intermediate 60 represented by the following formula was obtained according to the method described in Reference Production Example 16, using Intermediate 59 in place of Intermediate 21.

(156) ##STR00194##

(157) Intermediate 60: .sup.1H-NMR (DMSO-d.sub.6) : 1.07 (3H, t), 2.99-3.05 (2H, m), 7.74 (1H, d), 7.97 (1H, d), 8.07 (1H, d), 8.42 (1H, d), 9.05 (1H, br s).

Reference Production Example 32

(158) Intermediate 61 represented by the following formula was obtained according to the method described in Reference Production Example 12, using Intermediate 60 in place of Intermediate 14.

(159) ##STR00195##

(160) Intermediate 61: .sup.1H-NMR (DMSO-ds) : 1.31-1:38 (3H, m), 3:964.05 (2H, m), 7.97-7.99 (1H, m), 8:15 (2H, d), 8.30 (1H, d), 9.45 (1H, s).

Reference Production Example 33

(161) To a mixture of 0.50 g of Intermediate 63 and 5 mL of methanol was added dropwise 0.3 mL of sodium methoxide (25% methanol solution) under ice-cooling, and the mixture was stirred at room temperature for 16 hours. To the mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.38 g of Intermediate 65 represented by the following formula.

(162) ##STR00196##

(163) Intermediate 65: .sup.1H-NMR (CDCl.sub.3) :3.95 (3H, s), 5.00 (2H, t), 6.64 (1H, d), 7.65 (lit, d), 8.01 (1H, d), 8.12 (1H, s), 8.41 (1H, s), 8.75 (1H, d).

Production Example 1

(164) To a mixture of 0.84 g of Intermediate 4 and 6 mL of 1,4-dioxane were added 0.29 g of tris(dibenzylideneacetone)dipalladium (0), 0.36 g of xantphos 0.8 mL of diisopropylethylamine, and 0.2 mL of ethanethiol, and the mixture was refluxed for 90 minutes. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 0g of Compound 1 of the present invention represented by the following formula.

(165) ##STR00197##

(166) Compound of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8.93 (1H, s), 8.56 (1H, d), 8.40 (1H, d), 7.77 (1H, dd), 7.44 (1H, dd), 7.40 (1H, dd), 4.56 (2H, td), 2.90 (2H, q), 1.16 (3H, t).

Production Example 2

(167) Compounds produced according to die method described m Production Example 1 and physical property values thereof are shown below.

(168) Compounds represented by Formula (A-3) in which a combination, of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 24. In Tables 24 and 25, Comp means a compound of the present invention.

(169) ##STR00198##

(170) TABLE-US-00024 TABLE 24 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 2 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 CH 5 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CH CH 24 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CF CH CH 27 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH.sub.3 CH CH 30 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CH 32 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CBr N 34 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH Cc-Pr CH CH 39 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 N CCF.sub.3 CH CH 41 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH N 43 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 N 68 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH COCH.sub.3 N

(171) Compound 2 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8.68 (1H, d), 8.55 (1H, t), 8.39-8.37 (1H, m) 7.97 (1H, t), 7.40 (1H, dd), 7.11 (1H, dd), 4.56 (2H, td), 2.91 (2H, q), 1.15 (3H, t).

(172) Compound 5 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8:56 (2H, dq), 8.40 (1H, dd), 7.69 (1H, dt), 7.38 (1H, dd), 7.30 (1H, ddd), 6.94 (1H, td), 4.54 (2H, td), 2.84 (2H, q), 1.14 (3H, t).

(173) Compound 24 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8:54 (1H, d), 8.50 (1H, ddd), 8.37 (1H, dd) 7.66 (1H, ddd), 7.38 (1H, dd), 7.24-7.19 (1H, m), 4.54 (2H, td), 2.86 (2H, q), 1.15 (3H, t).

(174) Compound 27 of the present invention: LC-MS (measurement condition A): RT=3.72 min (260 nm), MS found: 417:8 [M+H].

(175) Compound 30 of the present invention: LC-MS (measurement condition B): RT=3.41 min (260 nm), MS found: 482.0 [M+H].

(176) Compound 32 of the present invention: LC-MS (measurement condition B): RT=2.17 min (260 nm), MS found: 484.1 [M+2H],

(177) Compound 34 of the present invention: LC-MS (measurement condition B): RT=3.97 min (260 nm), MS found: 443.8 [M+H].

(178) Compound 39 of foe present invention: .sup.1H-NMR (CDCl.sub.3) : 1.17 (3H, t), 3.00-3.06 (2H, m), 4.55 (2H, t), 7.38-7.43 (2H, m), 8.16 (1H, d), 8.44 (1H, d), 8.56 (1H, d).

(179) Compound 41 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.15 (3H, t), 3.01 (2H, q), 4.51 (2H, t), 7.41-7.43 (1H, m), 8.42 (1H, m), 8.54 (1H, m), 8.77 (1H, s), 9.15 (1H, s).

(180) Compound 43 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.16 (3H, t), 3.03-3.05 (2H, m), 4.54 (2H, t), 7.29-7.31 (1H, m), 7.40 (1H, d), 8.44 (1H, d), 8.53 (1H, s), 9.04 (1H, d).

(181) Compound 68 of foe present invention: LC-MS (measurement condition A): RT=3.52 min (260 nm), MS found: 434.7 [M+H].

(182) Compound 17 of the present invention represented by the following formula

(183) ##STR00200##

(184) Compound 17 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8.84 (1H, dd), 8.49 (1H, dd), 8.08-8:05 (1H, m), 7.90-7.81 (4H, m), 4.49 (2H, t), 2.80 (2H, q), 1.13 (3H, t).

Production Example 3

(185) To a mixture of 0.54 g of Compound it of the present invention and 6 mL of chloroform was added 0.6 g of 70% mCPBA under ice-cooling, and the mixture was stirred at room temperature for 6 hours. To the mixture was added a saturated sodium hydrogen carbonate aqueous solution, and then a sodium thiosulfate aqueous solution was added thereto. The mixture was extracted with chloroform. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 0.47 g of Compound 3 Of the present invention represented by the following formula.

(186) ##STR00201##

(187) Compound 3 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.67 (1H, d), 8.46 (1H, d), 8.12 (1H, d), 7.85 (1H, d), 7.62 (1H, dd), 7.43-7.40 (1H, m), 4.55 (2H, td), 4.00 (2H, q), 1.41 (3H, t).

Production Example 4

(188) Compounds produced according to the method described in Production Example 3 and physical property values thereof are shown below,

(189) Compounds represented by Formula (A-4) in which a combination of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 25,

(190) ##STR00202##

(191) TABLE-US-00025 TABLE 25 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 4 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 CH 6 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CH CH 14 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CBr CH CH 25 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CF CH CH 28 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCH.sub.3 CH CH 31 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH 03 CH CH 33 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CBr CH 35 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH Cc-Pr CH 40 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 N CCF.sub.3 CH CH 42 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH N 44 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 N 69 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH COCH.sub.3 N

(192) Compound 4 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.41 (1H, d), 8.46 (1H, d), 8.11 (1H, d), 8.05 (1H, s), 7.52-7.40 (1H, m), 7.20 (1H, dd), 4.55 (2H, t), 4.00 (2H, q), 1.40 (3H, t).

(193) Compound 6 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.25 (1H, d), 8.45 (1H, d), 8.07 (1H, d), 7.76 (1H, dd), 7.50-7.45 (1H, m), 7.40 (1H, dd), 7.05 (1H, td), 4.54 (2H, t), 3.92 (2H, q), 1.39 (3H, t).

(194) Compound 14 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.42 (1H, dd), 8.44 (1H, d), 8.07 (1H, d), 7.64 (1H, dd), 7.54 (1H, dd), 7:40 (1H, dd), 4.54 (2H, td), 3.95 (2H, q), 1.40 (3H, t).

(195) Compound 25 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.26 (1H+dd), 8.44 (1H, d), 8.07 (1H, d), 7.73 (1H, dd), 7.40 (2H, dq), 4.54 (2H, dd), 3.95 (2H, q), 1.39 (3H, t).

(196) Compound 28 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.37 (3H, t), 2.40 (3H, s), 3.87 (2H, q), 4.52 (2H, t), 7.30 (1H, d), 7.35-7.38 (1H, m), 7.63 (1H, d), 8.02 (1H, d), 8.42 (1H, d), 9.00 (1H, s).

(197) Compound 31 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.41 (3H, t), 3.99 (2H, q), 4.54 (2H, t), 7.40 (1H, d), 7.66 (1H, d), 7.90 (1H, d), 8.12 (1 K d), 8.45 (1H, s), 9.01 (2H, s), 9.30 (1H, s), 9.53 (1H, s).

(198) Compound 33 of the present invention: .sup.1H-NMR (CDCl.sub.3) :1.36 (3H, t), 3.93 (2H, q), 4.53 (2H, t), 7.12 (I K d), 7.38 (1H, d), 7.91 (1H, s), 8:05 (1H, ti), 8.43 (1H, s), 9.12 (1H, d).

(199) Compound 35 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 0.84 (2H, t), 1.12-1.14 (2H, m), 1.34 (3H, t), 1.98-2.03 (1H, m), 3.84-3.90 (2H, m) 4.52 (2H, t), 6.70 (1H, d), 7.36-7.37 (2H, m), 8.03 (1H, d), 8.41 (1H, d), 9.06 (1H, d).

(200) Compound 40 of the present invention: .sup.1H-NMR (CDCl.sub.3) :1.40 (3H, t), 3.70 (2H, q), 4.54 (2H, t), 7.37-7.39 (1H, m), 7.62 (1H, d), 7.96 (1H, d), 8.29 (1H, d), 8.50 (1H, d).

(201) Compound 42 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.41 (3H, z), 4.10 (2H, q), 4.55 (2H, t), 7.41-7-43 (1H, m), 8.32 (1H, d), 8.46-8.47 (1H, m), 8.92 (1H, s), 9.95 (1H, s).

(202) Compound 44 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.39 (3H, t), 4.10 (2H, q), 4.55 (2H, t), 7.39-7.44 (2H, m), 8.32 (1H, d), 8:46 (1H, d), 9.82 (1H, d).

(203) Compound 69 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.31-1.38 (3H, m), 3.98-4.03 (2H, m), 4.11 (3H, s), 4.52 (2H, z), 6.58 (1H, d), 7.33-7.54 (1H, m), 8.22 (1H d), 8.41 (1H, d), 9.28 (1H, d).

(204) Compound 18 of the present invention represented by the following formula

(205) ##STR00204##
Compound 18 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8.61 (1H, d), 8.43 (1H, d), 82-5 (1H, d), 7.90-7.67 (4H, m), 4:56 (2H, t), 3.39 (2H, q), 1:28 (3H, t).

Production Example 5

(206) A mixture of 0.26 g of Intermediate 16, 0.05 g of [1,1-bis(diphenylphosphino)ferrocene]palladium (II) dichloride, 0.38 g of tripotassium phosphate, 9.38 g of 4-fluorophenylboronic acid, 0.3 mL of water, and 3 mL of DME was stirred under a nitrogen atmosphere at 85 C. for 3 hours. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain 0.20 g of Compound 7 of the present invention represented, by the following formula.

(207) ##STR00205##

(208) Compound 7 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.72 (1H, s), 8.91 (1H, dd), 8:20 (1H, dd), 8.01 (1H, dd), 7.88 (1H, d), 7.65 7.62 (3H, m), 7.11 (2H, tt), 4.09 (2H, q), 1.44 (3H, t).

Production Example 6

(209) The compounds produced according to the method described in Production Example 5 and the physical property values thereof are shown below

(210) Compounds represented by Formula (A-5) in which a combination of R.sup.2, G.sup.1, G.sup.2, G.sup.3, G.sup.4, and G.sup.5 is any one of the combinations described in Table 26.

(211) ##STR00206##

(212) TABLE-US-00026 TABLE 26 Comp R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 G.sup.5 8 CH.sub.2CH.sub.3 CH CH CCF.sub.3 CH CH 9 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH CH 10 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CCF.sub.3 CH 11 CH.sub.2CH.sub.3 CH CH CCF.sub.3 N CH 12 CH.sub.2CH.sub.3 CH CCF.sub.3 CH N CH

(213) Compound 8 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.71 (1H, s), 8.96 (1H, dd), 8.24 (1H, dd), 8.07 (1H, dd), 7.89 (1 FI, d), 7.74-7.63 (1H, m), 7.27-7.22 (4H, m), 4.10 (2H, q), 1.47 (3H, t).

(214) Compound 9 of the present invention .sup.1H-NMR (CDCl.sub.3) : 9.72 (1H, s), 8.97 (1H, t), 8:25 (1H, d), 8.08 (1H, dd), 7:91-7.81 (3H, m), 7.72 (1H, t), 7:65 (2H, q), 4.10 (2H, q), 1.45 (3H, t).

(215) Compound 10 of the present invention: .sup.1H-NMR (CDCl.sub.3) :9.71 (0.1H, d), 8:99 (1H, dd), 8.29 (1H, dd), 8.12 (1H, s), 8.11 (2H, t), 7.96 (1H, s), 7.90 (1H, d), 7.65 (1H, dd), 4.09 (2H, q), 1.46 (3H, t),

(216) Compound 11 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.71 (1H, d), 9.04 (1H, d), 8.98 (1H, dd), 8.30 (2H, dd), 8.10 (1H, dd), 7.86 (2H, dd), 7.65 (1H, dd), 4.09 (2H, q), 1.46 (3H, t).

(217) Compound 12 of the present invention: .sup.1H-NMR (CDCl.sub.3) :9.71 (1H, s), 9.12 (1H, d), 8.98 (2H, dt), 8.30 (1H, dd), 8.20-8.19 (1H, m), 8.11 (1H, dd), 7:90 (1H, d), 7.65 (1H, dd), 4.09 (2H, q), 1.46 (3H, t).

Production Example 7

(218) Intermediate 13 was obtained according to the method described in Reference Production Example 3, using Intermediate 12 in place of intermediate 3 mid using 7.2 g of 5-bromo-2-aminopyridine in place of 5-(trifluoromethyl)-2-aminopyridine.

(219) ##STR00207##

(220) Compound 13 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 8.70 (1H, dd), 8.54 (1H, d), 8.37 (1H, d), 7:57 (1H, dd), 7.37 (2H, td), 4.54 (2H, dd), 2.87 (2H, q), 1.15 (3H, t).

Production Example 8

(221) Compound 15 of the present invention represented by the following formula was obtained according to the method described in Production Example 5, using Compound 14 of the present invention lit place of Intermediate 16.

(222) ##STR00208##

(223) Compound 15 of the present invention: .sup.1H-NMR (CDCl.sub.3) :9.41 (1H, dd), 8.46 (1H, d), 8.10 (1H, d), 7.81 (1H, dd), 1.15 (2H, dd), 7.69 (1H, dd), 7.60-7.57 (2H, m), 7.41 (1H, dd), 4.58-4.52 (2H, m), 3.95 (2H, q), 1.41 (3H, t).

Production Example 9

(224) Compounds produced according to the method described in Production Example 8 and physical property values, thereof are shown below.

(225) Compounds represented by Formula (A-6) in which a combination of R.sup.2. G.sup.1, R.sup.3b, R.sup.3c, and G.sup.4 is a combination described in Table 27.

(226) Formula (A-6):

(227) ##STR00209##

(228) TABLE-US-00027 TABLE 27 Comp R.sup.2 G.sup.1 R.sup.3b R.sup.3c G.sup.4 16 CH.sub.2CH.sub.3 CH 0 H CH 37 CH.sub.2CH.sub.3 CH H CH 38 CH.sub.2CH.sub.3 CH H CH

(229) Compound 16 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.03 (1H, d), 8:43 (1H, d), 8.04 (1H, d), 7.65 (1H, d), 7.38 (1H, dd), 7:17 (1H, dd), 4.54 (2H, t), 3.87 (2H, q), 2.03-1.96 (1H, m), 1.38 (3H, t), 1.08-1.03 (2H, m), 0.76 (2H, dd).

(230) Compound 37 of the present invention: .sup.1H-NMR (CDC.sub.3) :1.39 (3H, t), 3.93-3.95 (2H, m), 4.53 (2H, t), 7.19-7.24 (3H, m), 7.38-7.40 (1H, m), 7.65 (2H, s), 7.86 (1H, s), 8.08-8.10 (1H, m), 8.44 (1H, s), 9.25 (1H, d).

(231) Compound 38 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.40 (3H, t), 3.95-4.01 (2B, m), 4.54 (2H, t), 7.2-5 (1H, s), 7.40-7.41+(1H, m), 7.97 (1H, i>), 8.10 (1H, d), 8.46 (1H, s), 9.07. (2H, s), 9.31 (1H, s), 9.40 (1H, d).

Production Example 10

(232) A mixture of 200 mg of Intermediate 23,480 mg of cesium carbonate, 210 mg of 2,2,3,3-tetrafluoropropanol, and 4 mL of N-methylpyrrolidone (hereinafter referred to as NMP) was stirred at 70 C. for 2 hours. After codling the obtained mixture to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane:ethyl acetate=2:1) to obtain 200 mg of Compound 19 of the present invention as shown below.

(233) ##STR00213##

(234) Compound 19 of the present invention: .sup.1H-NMR (CDCl.sub.3) :9.62 (1H, s), 8.87 (1H, d), 8.40 (1H, d), 7.88 (1H, d), 7.65 (1H, dd), 6.02 (1H, tf) 4.85 (2H, t) 3.89 (2H, q), 1.42 (3H, t).

Production Example 11

(235) Compounds produced according to the method described in Production Example 10 and physical property values thereof are shown below.

(236) Compounds represented by Formula (A-7) in which a combination of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is a combination described in Table 28.

(237) ##STR00214##

(238) TABLE-US-00028 TABLE 28 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 20 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH

(239) Compound 20 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.63 (Hi, s), 8.87 (1H, d), 8.43 (1H, d), 7.89 (1H, d)#7.65 (1H, dd), 4:93 (2H, t), 3:90 (2H, d), 1.42 (3H, t).

Production Example 12

(240) To a mixture of 0.50 g of Intermediate 38# cesium carbonate 0.42 g, and 5 mL of DMF was added dropwise 0.34 g of 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the mixture was added water, and the mixture was extracted with MTBE. The obtained organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane:ethyl acetate=4:1) to obtain 0.39 g of Compound 21 of the present invention represented by tire following formula.

(241) ##STR00215##

(242) Compound 21 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.67 (1H, d), 8.45 (1H, dd), 8.11 (1H, dd), 7.85 (1H, d), 7.61 (1H, dd), 7.40 (1H, dd), 4.47 (2H, q), 4.00 (2H, q), 1.41 (411, q).

Production Example 13

(243) Compounds produced according to the method described in Production Example 12 and physical property values thereof are shown below. Compounds represented by Formula (A-4) in which a combination of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 29.

(244) TABLE-US-00029 TABLE 29 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 22 OCH.sub.2CF.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 CH 23 OCH.sub.2CF.sub.2CFHCF.sub.3 CH.sub.2CH.sub.3 CH CH CCF.sub.3 CH 26 OCH.sub.2CF.sub.2CF.sub.2H CH.sub.2CH.sub.3 CH CF CH CH

(245) Compound 22 of the present invention: .sup.1H-NMR (CDCl.sub.3): : 9.67 (1H, s), 8.47 (1H, d), 8.13 (1H, d), 7.85 (1H, d), 7:62 (1H, dd), 7.42 (1H, dd), 4.59 (2H, t), 4.00 (2H, q), 1.41 (3H, t).

(246) Compound 23 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 9.67 (1H, s), 8.45 (1H, d), 8.12 (1H, d), 7.85 (1H, d), 1.62 (1H, dd), 7.41 (1H, dd), 5.29-5.10 (1H, m), 4.58-4.39 (2H, m), 4.04-3.97 (2H, m), 1.42 (3H, t).

(247) Compound 26 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 926 (1H dd), 8.43 (1H, d), 8.06 (1H, d), 7.74-7.70 (1H, m), 739 (2H, ddd), 6.08 (1H, tt), 4.48 (2H, td), 3.95 (2H, q), 1.39 (3H, t).

Production Example 14

(248) Compounds produced according to the method described in Production Example 23 and physical property values thereof are shown below.

(249) Compounds represented by Formula (A-4) in which a combination of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 30,

(250) TABLE-US-00030 TABLE 30 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 29 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CH 36 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CH CH

(251) Compound 29 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.40 (3H, t), 3.98-4.00 (2H, m), 4.54 (2H, t), 6.80 (1H, d), 7.42 (1H, d), 7.86 (1H, m), 7.95-7.99 (2H m), 8.12 (1H, d), 8.45 (1H, s), 9.66 (1H, s).

(252) Compound 36 of the present invention: (CDCl.sub.3) : 1.3943H, t), 3.97 (2H, q), 4.54 (2E t)>6.82 (1H, d), 7.40 (1H, dd), 7.62 (1H, dd), 7.93-7.94 (1H, m) 8.08-8.11 (2H, m), 8.45 (1H, d), 9.36 (1H, d).

Production Example 15

(253) compounds produced according to the method described in Production Example 2 and physical property values thereof are shown below.

(254) Compounds represented by Formula (A-11) in which a combination of T, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 31.

(255) ##STR00218##

(256) TABLE-US-00031 TABLE 31 Comp T G.sup.1 G.sup.2 G.sup.3 G.sup.4 45 CH CH CH CH 47 0 CH CH CH CH 49 CH CH CH CH 51 OCH.sub.2CF.sub.2CF.sub.3 CH CCF.sub.3 CH CH 53 CH CCF.sub.3 CH CH 55 CH CCF.sub.3 CH CH 57 CH CCF.sub.3 CH CH 59 OCH.sub.2CF.sub.2CF.sub.3 N CCF.sub.3 CH CH

(257) Compound 45 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.18-1.24 (3H, m), 4.0$ (2H, q), 735-7:43 (1H, m % 7.43-7.49 (2H, m) 7.52-7.56 (2H, m % 1:63-7.67 (2H, m), 7.81-7.85 (1H, m), 9.00 (1H, s), 9.16 (1H, s).

(258) Compound 47 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) : 1.09 (3H, t), 3.04-3.09 (2H, m), 7.71: (1H, d), 7.94-7.99 (3H, m), 8.76 (2H, d), 9.04 (1H, s), 9.47 (2H, s).

(259) Compound 49 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.18 (3H, t), 3.00 (2H, q), 6.83-6.84 (1H m % 6.97-6.99 (1>1, m), 7.33 (lilt), 7.75 (1H, d), 8.08 (1H, s), 8.63 (Hid), 9.31 (2H, s).

(260) Compound 51 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1:17 (3H, t), 3.01 (2H, q), 4.60 (2H, t) 7.43 (1H, d), 7.81 (1H, d), 8.67 (2H, s), 8.97 (1H, s).

(261) Compound 53 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 119-1.24 (3H, m), 3.05 (2H, t), 6.85 (1H, s), 7.46 (1H, d), 7.85 (1H, d), 8.09 (1H, s), 9.00 (1H, s), 9.33 (2H, s).

(262) Compound 55 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.21 (3H, t), 3.10 (2H, t), 7.45 (1H, d), 7.68-7.74 (1H, m), 7.82-7.89 (3H, m), 8.54 (1H, d), 9.01-9.05 (1H, m), 9.17 (2H, s).

(263) Compound 57 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.15-1.28 (3H, m), 3.06-3.11 (2H, m), 133.7.50 (1H, m), 7.84 (1H, t), 8.15-8.18 (1H, m), 8.54-8.59 (1H, m), 8.99-9.01 (1H, m), 9.08-9.11 (2H, s), 9.19 (1H, s).

(264) Compound 59 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 118 (3H, t), 3:13 (2H, q), 4.61 (2H, t), 7.42 (1H, d), 8.20 (1H, d), 8.69 (2H, s).

Production Example 16

(265) Compounds produced according to the method described in Production Example 3 and physical property values thereof are shown below.

(266) Compounds represented by Formula (A-12) in which a combination of T. G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is any one of the combinations described in Table 32.

(267) ##STR00225##

(268) TABLE-US-00032 TABLE 32 Comp T G.sup.1 G.sup.2 G.sup.3 G.sup.4 46 CH CH CH CH 48 CH CH CH CH 50 CH CH CH CH 52 OCH.sub.2CF.sub.2CF.sub.3 CH CCF.sub.3 CH CH 54 CH CCF.sub.3 CH CH 56 0 CH CCF.sub.3 CH CH 58 CH CCF.sub.3 CH CH 60 OCH.sub.2CF.sub.2CF.sub.3 N CCF.sub.3 CH CH

(269) Compound 46 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.47 (3H, t), 4.07 (2H, q), 7.49-7.56 (3H, m), 7.62-7.67 (3H, m), 7.96 (1H, d), 9.13 (2H, s), 9.69 (1H, s).

(270) Compound 48 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) : 1.36 (3H, t), 4.05 (2H, q), 7.95-8.00 (31i m), 8.12 (1H, d), 8.77 (2H, d), 9.41 (1H, s), 9.49 (2H, s).

(271) Compound 50 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 144 (3H, t), 3:95 (2H, t).sub.5 6.85 (1H, s), 7.09-7.11 (1H, m), 7.49-7.53 (1H, d).sub.5 7-86 (1H, d), 8.10 (1H, s), 9.23-9.31 (3H, m).

(272) Compound 52 of the present invention: .sup.1H-NMR (CDCl.sub.3) :1.43 (3H, t), 3.96 (2H, q), 4.61 (2H, t), 7:62 (1H, d), 7.93 (1H, d), 8.65 (2H, s), 9.63 (1H, s).

(273) Compound 54 of the present invention: .sup.1H-NMR (CDCl.sub.3) :1.46 (3H, t).sub.3 4.00 (2H, q), 6.87 (1H, d), 7.65 (1H, dd), 7.96 (1H, d), 8.12 (1H d), 9.33 (2H, s), 9.65 (1H, s).

(274) Compound 56 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.46 (3H, t), 4.65 (2H, q), 7.63-7.71 (2H, m), 7.76-7.77 (1H, m), 7.85 (1H, d), 7.90 (1H, s), 7.97 (1H, d), 9.15 (2H, s), 9.68 (1H, s).

(275) Compound 58 of the present invention: .sup.1H-NMR (CDCl.sub.3) :1.47 (3H, t), 4.04 (2H, q), 7.65 (1H, d), 7.98 (1H, d), 7.19 (1H, s), 9.03 (1H, s), 9.12 (1H, s), 9.18 (2H, s), 9.67 (Ills).

(276) Compound 60 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.47 (3H, t), 3.73 (2H, q), 4.61 (2H, t), 7.63 (1H, d), 8.32 (1H, d), 8.64 (2H, s).

Production Example 17

(277) Compounds produced according to the method described in Production Example 10 and physical property values thereof are shown below.

(278) Compounds represented by Formula (A-13) in which a combination of T, R.sup.2, G.sup.1, G.sup.2, G.sup.3, and G.sup.4 is a combination described in Table 33.

(279) ##STR00232##

(280) TABLE-US-00033 TABLE 33 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 61 OCH.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH 62 OCH.sub.2CF.sub.2CF.sub.2H CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH 63 OCH.sub.2CF.sub.2CFHCF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH 64 OCH.sub.2CF.sub.2CF.sub.2CF.sub.3 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH

(281) Compound 61 of the present invention: H-NMR (CDCl.sub.3) : 1.32 (3H, t), 3.99 (2H, q), 5.40 (2H, t), 7-63 (1H, d), 7.96 (1H, d), 8.13 (1H, d), 8.25 (1H, d), 9.44 (1H, s).

(282) Compound 62 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) : 1.32 (3H, t), 4.00 (2H, q), 5.17 (2H, t), 6.60-6.89 (1H, m), 7.58 (1H, d), 7.96 (1H, dd), 8.13 (1H, d), 8.23 (1H, d), 944 (1H, s).

(283) Compound 63 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) : 1.33 (3H, t), 4.00 (2H, q), 5.14-5.1.8 (2H, m), 6.23-6.24 (1H, m), 7.58 (1H, d), 7.94 (1H, d), 8.13 (114, d), 8.25 (1H, d), 9.45 (1H, s).

(284) Compound 64 of the present invention: .sup.1H-NMR (DMSO-d.sub.6): : 1.32 (3H, t), 4.00 (2H, q), 5.43 (2H, t), 7.63 (1H, d), 7.96 (1H, d), 8.14 (1H, d), 8.25 (1H, d), 9.44 (1H, s).

Production Example 18

(285) Compounds produced according to the method described in Reference Production Example 15 and physical property values thereof are shown below.

(286) Compound 70 of the present invention represented by the following formula was obtained according to the method described in Reference Production Example 15, using Compound 69 Of the present invention in place of Intermediate 20.

(287) ##STR00233##

(288) Compound 70 of the present invention: LC-MS (measurement condition B): RT=2.78 min (260 nm), MS found: 453.2 [M+H],

Production Example 19

(289) Compounds produced according to the method described in Production Example 5 and physical property values thereof are shown below. Compounds represented by Formula (A-13) in which a combination of T, R, G.sup.1, G.sup.2. G.sup.3 and G.sup.4 is any one of the combinations described in Table 34.

(290) TABLE-US-00034 TABLE 34 Comp T R.sup.2 G.sup.1 G.sup.2 G.sup.3 G.sup.4 65 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH 66 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH 67 CH.sub.2CH.sub.3 CH CCF.sub.3 CH CH

(291) Compound 65 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) :1.37 (3H, t), 4.11 (2H, q), 7:86 (1H, t), 7.96-8.00 (2H, m), 8:12 (1H, d), 8.58-8.64 (3H, m), 9.48 (1H, s).

(292) Compound 66 of the present invention: .sup.1H-NMR (DMSO-d.sub.6) : 1.37 (3H, t), 4.09-4.11 (2H, m), 7.89 (1H, d), 8.17 (1H, d), 8.42 (1H, d), 8.73 (1H, d), 9.00 (1H, s), 9.19 (1H, s), 9.47 (1H, s), 9.73 (1H, s).

(293) Compound 67 of the present invention: .sup.1H-NMR (CDCl.sub.3) : 1.47 (3H, t), 4.04 (2H, q).sub.4 6.82 (1H+d), 7.67 (18, dd), 7.90 (1H, d), 8.40. (2H, qz), 8.90 (1H, d), 9.67 (1H, s).

(294) Next, formulation examples of the compounds of the present invention are shown. Parts represent parts by weight.

Formulation Example 1

(295) 10 parts of any one of Compounds 1 to 70 of the present invention are mixed with a mixture of 35 parts of xylene and 35 parts of DMR, and 14 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfohate are added thereto. The resultant is mixed to obtain each formulation.

Formulation Example 2

(296) 4 parts of sodium laurylsulfate, 2 parts of calcium ligninsulfonate, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaeecus earth are mixed, and 20 parts of any one of Compounds 1 to 70 of the present invention is, further added thereto. The resultant is mixed to obtain each formulation.

Formulation Example 3

(297) To 2 parts of any one of Compounds 1 to 70 of the present invention are added 1 part of synthetic hydrated silicon oxide fine powder, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay, and the resultant is mixed. Then, to the mixture is added an appropriate amount of water. The mixture is further stirred, granulated by a granulator, and air-dried to obtain each formulation.

(298) Formulation Example 4

(299) 1 part of any one of Compounds 1 to 70 of the present invention is mixed with an appropriate amount of acetone, and 5 parts of synthetic hydrated silicon oxide fine powder, 0.3 parts of isopropyl acid phosphate, and 93.7 parts of kaolin, clay are added thereto. The resultant is sufficiently stirred and mixed, and acetone is removed by evaporation to obtain each formulation.

Formulation Example 5

(300) 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1i 1), 20 parts of any one of Compounds 1 to 70 of the present invention, and 45 parts of water are thoroughly mixed to obtain a formulation.

Formulation Example 6

(301) 0.1 parts of any one of Compounds ho 70 of the present invention is mixed with a mixture of 5 parts of xylene and 5 parts of trichloroethane. The mixture is mixed with 89.9 parts of kerosene to obtain each formulation.

Formulation Example 7

(302) 10 mg of any one of Compounds 1 to 70 of the present invention is mixed with 0.5 nil of acetone. This solution is added dropwise to 5 g of solid feed powder for animals (Breeding Solid Feed Powder CE-2, manufactured by Japan Clea Co, Ltd.) and the resultant is mixed uniformly. Then, the acetone is dried by evaporation to obtain each poison bait.

Formulation Example 8

(303) 0.1 parts of any one of Compounds 1 to 70 of the present invention and 49.9 parts of NEO-CHIOZOL (manufactured by Chuo Kasei Co., Ltd.) are put in an aerosol can, and an aerosol valve is mounted thereon. Then the can is filled with 25 parts of dimethyl ether and 25 parts of LPG and shaken, and an actuator is mounted thereon to obtain an oily aerosol.

Formulation Example 9

(304) Ah aerosol container is filled with a mixture of 0.6 parts of any one of Compounds 1 to 70 of the present invention, 0.01 parts of 2,6-di-tert-butyl-4-methylphenol, 5 parts of xylene, 339 parts of kerosene, and 1 part of an emulsifier {RHEODOL MO-60 (manufactured by Kao Corporation)}, and 50 parts of distilled water, and a valve is mounted thereon. Then, the container is filled with 40 parts of a propellant (LPQ) under pressure through the valve to obtain an aqueous aerosol.

Formulation Example 10

(305) 0.1 g 6f any one of compounds 1 to 70 Of the present invention is mixed with 2 ml of propylene glycol, and the mixture is impregnated into a ceramic plate of 4.0 cm4.6 cm having a thickness of 1.2 cm, to obtain a heating type smoking agent.

Formulation Example 14

(306) 5 parts of any one of Compounds 1 to 70 Of the present invention and 95 parts of dm ethylene-methyl methacrylate copolymer (a proportion of methyl methacrylate relative to the total weight of the copolymer: 10% by weight, Acryft WD301, manufactured by Sumitomo Chemical Co., Ltd.) are melt-kneaded with a closed pressurizing kneader (manufactured by Moriyama Works), and the obtained kneaded matter is extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 12

(307) 5 parts of any one of Compounds 1 to 70 of the present invention and 95 parts, of a soft vinyl chloride resin are melt-kneaded with a closed pressurizing kneader (manufactured by Moriyama Works), and the obtained kneaded matter is extended from an extrusion molding machine through a molding die to obtain rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.

Formulation Example 13

(308) 100 mg of anyone of Compounds 1 to 70 of the present invention, 68.75 mg of lactose, 237.5 mg of corn starch, 43.75 mg of microcrystalline cellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodium carboxy methyl starch, and 2.5 mg of magnesium stearate are mixed, and the obtained mixture, is compressed to an appropriate size to obtain a tablet.

Formulation Example 14

(309) 25 mg of any one of Compounds 1 to 70 of the present invention 60-mg of lactose, 25 mg of corn starch, 6 mg of carmellose calcium an appropriate amount of 5% hydroxypropyl methylcellulose are mixed, and a hard shell gelatin capsule or a hydroxypropylmethyl cellulose capsule is filled with the obtained mixture to obtain an encapsulated formulation.

Formulation Example 15

(310) To 100 mg of any one of Compounds 1 to 70 of the present invention, 500 mg of fumaric acid, 2,000 mg of sodium chloride, 150 mg of methylparaben, 50 mg of propylparaben, 25,000 mg of granulated sugar, 13,000 mg of sorbitol (70% solution), 100 mg of Veegum K (Vanderbilt Co.), 35 mg of a perfume, and 500 mg of a colorant is added distilled water so as to make a final volume of 100 ml, and the resultant is mixed to obtain a suspension for oral administration,

Formulation Example 16

(311) 5% by weight of any one of Compounds 1 to 70 of the present invention is mixed with 5% by weight of an emulsifier, 3% by weight of benzyl alcohol, and 30%, by weight of propylene glycol, and a phosphate buffer is, added thereto so that a pH of the solution is 6.0 to 6.5. Then, water as a remaining portion is added thereto to obtain a liquid formulation for oral administration.

Formulation Example 17

(312) 5% by weight of aluminum distearate is added in 57% by weight of fractionated palm oil and 3% by weight of polysorbate 85, and dispersed therein by heating. 25% by weight of saccharin is dispersed in an oily vehicle obtained by cooling this dispersion to room temperature. To the resultant is dispensed 10% by weight of any one of Compounds 1 to 70, to obtain a pasty formulation for oral administration.

Formulation Example 18

(313) 5% by weight of any one of Compounds 1 to 70 Of the present invention is mixed with 95% by weight of limestone powder, and a wet granulation method is used to obtain a granule for oral administration.

Formulation Example 19

(314) 5 parts of any one of Compounds 1 to 70 of the present invention are mixed with 80 parts of diethylene glycol monoethyl ether, and the mixture is mixed with 15 parts of propylene carbonate to obtain a spot-on solution.

Formulation Example 20

(315) 10 parts of any one of Compounds 1 to 70 of the present invention are mixed with 70 parts of diethylene glycol monoethyl ether, and the mixture is mixed with 20 parts of 2-octyl dodecanol to obtain a pour-On solution.

Formulation Example 21

(316) To 0.5 parts of any one of Compounds 1 to 70 of the present invention are added 60 parts of NIKKOL TEALS-42 (Nikko Chemicals Co., Ltd., 42% aqueous solution of triethanolamine lauryl sulfate) and 20 parts of propylene glycol, and the mixture is sufficiently stirred and mixed until the mixture becomes a uniform solution. Then, 19.5 parts of water are added t hereto, and tire resultant is further sufficiently stirred and mixed to obtain a shampoo formulation as a uniform solution.

Formulation Example 22

(317) 0.15% by weight of any one of Compounds 1 to 70 of the present invention, 95% by weight of an animal feed, and 4-85% by weight of a mixture of dibasic calcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are thoroughly stirred and mixed to obtain a feed premix for animals.

Formulation Example 23

(318) 7.2 g of any one of Compounds 1 to 70 of the present invention is mixed with 92.8 g of VOSCO S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) at 100 C. poured into a suppository mold, and cooled and solidified to obtain a suppository.

(319) Next, the efficacy of the compound of the present invention against harmful arthropods is shown by test examples. In the following test examples, the test is earned put in a state in which escape of insects is prevented and at a temperature of 25Q.

Test Example 1

(320) A test compound is made into a formulation according to the method described in Formulation Example 5, and water containing 0:03% by volume of a spreading agent is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.

(321) Approximately 30 Aphis gossypii (all stages) are inoculated into cucumber (Cucumis sativiis) seedlings (at a second main leaf development stage) which has been planted in a container. One day later, the diluted solution is sprayed on the seedlings at a rate of 10 mL/seedling. After 5 additional days, the number of surviving insects is investigated and a controlling value is calculated according to the following expression,
Controlling value (%)={1(CbTai)/(CaiTb)}100
Symbols in the expression represent the following, meanings.

(322) Cb: Number of test insects in a non-treated section

(323) Cai: Number of surviving insects at the time of investigating anon-treated section

(324) Tb: Number of test insects in a treated section

(325) Tai: Number of surviving insects at the time of investigating a treated section

(326) Here, tire non-treated section means a section where the same operation as the treated section is performed except that the test compound is not used.

(327) As a result of carrying out the test according to Test Example f using the following compounds of tire present invention as test compounds at a predetermined concentration of 500 ppm, the following compounds of the present invention all showed a controlling value of 90% or more.

(328) Compounds of the present invention: 3, 4, 6, 10, 14, 15, 16, 18, 19, 20, 21 to 29, 31, 33, 35, 37, 40, 44, 50, 52, 60, 66, and 67

Test Example 2

(329) A test compound is made into a formulation according to the method described, in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.

(330) The diluted solution is sprayed at a rate of 10 mL/seedling to a rice (Oryza sativa) seedling (at a second leaf development stage) which has been planted in a container. Later, twenty 3-instar larvae of brown rice planthopper are released thereinto. After 6 days, the number of surviving insects is investigated and a mortality rate of insects is determined by the following expression.
Mortality rate of insects (%)={1number of surviving insects/20}100

(331) As a result of carrying out the test according to Test Example 2 using the following compounds of the present invention as test compounds at predetermined concentration of 500 ppm, the following compounds of the present invention all showed a mortality rate of insects of 90% or more.

(332) Compounds of the present invention: 10, 16, 19, and 21

Test Example 3

(333) A test compound is made into a formulation according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.

(334) 7.7 g of artificial feed (Insecta LF, manufactured by Nosan Corporation) is placed in a container, and 2 mL of the diluted solution is irrigated thereto. Five 4-instar larvae of tobacco cutworm are released onto the artificial feed. After 5 days, the number of surviving insects is counted, and a mortality rate of insects is calculated by the following expression,
Mortality rate of insects (%)=(1number of surviving insects/5)100

(335) As a result of carrying out the test according to Test Example 3 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, the following compounds of the present invention all showed a mortality rate of insects of 80% or more,

(336) Compounds of the present invention: 3, 4, 6, 7, 11, 14, 15, 16, 19, 20, 21 to 23, 25, 26, 28, 29, 31, 33, 35 to 37, 40, 44, 50, 52, 54, 58, and 60 to 64

Test Example 4

(337) A test compound is made into a formulation according to the method described in Formulation Example 5, and water containing 0.03% by volume of a spreading agent is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.

(338) The diluted solution is sprayed at a rate of 20 mL/seedling to a cabbage (Brassicae oleracea) seedling (at a second to third main leaf development stage) which has been planted in a container. Then, stem and leaf of this seedling are cut off and put in a container with after paper spread. Five Z-instar larvae of diamondback moths are released thereinto. After 5 days, the number of surviving insects is counted and a mortality rate of insects is calculated by the following expression.
Mortality rate of insects %=(1number of surviving insects/5)100

(339) As a result of carrying out the test according to Test Example 4 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, the following compounds of the present, invent ion all showed a mortality rate of insects of 80% or more.

(340) Compounds of the present invention: 3, 4, 6, 7, 8, 10, 11, 12, 14, 15, 16, 18, 19, 20 to 26, 28, 29, 31, 33, 35, 37, 40, 42 to 44, 50, 52, 56, 58, and 60 to 64

Test Example 5

(341) 1 mg of each test compound is dissolved in 50 L of a mixed solution of polyoxyethylene sorbitan monococoate:acetone=5.95 (volume ratio). To the resultant is added water containing 0.03% by volume of a spreading agent, to prepare a diluted solution containing a predetermined concentration of the test compound.

(342) Seeds of corn (Zea mays) are seeded onto a tray lined with wet Kimwipes, After the corn has grown for 5 days, die entire seedlings are immersed into the diluted solution for 30 seconds. Thereafter, two seedlings are put in a petri dish (diameter of 90 mm), and ten 2-instar larvae of western corn rootworm are released thereinto. Five days later, the number of dead insects is counted, and a mortality rate of insects is calculated by the following expression.
Mortality rate of insects (%)=(number of dead insects/10)100.

(343) As a result of carrying out the test according to Test Example 5 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, the following compounds of the present invention all showed a mortality rate of insects of 80% or more.

(344) Compounds of the present invention: 1, 2, 3, 4, 5, 6, 15, 16, 19, 20 to 26, 28, 33, 38, 44, 52, and 60 to 64

Test Example 6

(345) A test compound is made into a formulation according to the method described in Formulation Example 5, and water is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.

(346) A container is lined with a filter paper having a diameter of 5.5 cm. 30 mg of sucrose is put on the filter paper and then 0.7 mL of the diluted solution is added thereon. Ten female-adult housefly are released into the container. After 24 hours, the number of dead insects is counted, and a mortality rate of insects is calculated by the following expression.
Mortality rate of insects (%)=(number of dead insects/number of test insects)100

(347) As a result of carrying out the test according to Test Example 6 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, the following compounds of the present invention all showed a mortality rate of insects of 100,%.

(348) Compounds of the present invention: 3, 4, 21, 22, 24, 33, 35, 40, 52, 61, and 62

INDUSTRIAL APPLICABILITY

(349) The compound of the present invention exhibits excellent controlling effects against harmful arthropods.