Heterocyclic compound and harmful arthropod-controlling composition containing same

A compound represented by formula (I)

• wherein:
• Z represents an oxygen atom or a sulfur atom;
• R1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group U, a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, C(O)R51C(O)OR51, or C(O)NR51R52,
• R51 and R52 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group V, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group V, or a hydrogen atom;
• R2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;
• n represents 0, 1, or 2;
• G1 represents a nitrogen atom or CR3a:
• G2 represents a nitrogen atom or CR3b;
• G3 represents a nitrogen atom or CR3e;
• G4 represents a nitrogen atom or CR3d;
• R3a, R3b, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group E, a phenyl group optionally substituted with one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group H, OR12, NR11R12, NR11aR12a NR24NR11R12, NR24OR11, NR11C(O)R13, NR24NR11C(O)R13, NR11C(O)OR14, NR24NR11C(O)OR14, NR11C(O)NR31R32, NR24NR11C(O)NR31R32, N═CHNR31R32, N═S(O)pR15R16, C(O)R13, C(O)OR17, C(O)NR31R32, C(O)NR11S(O)2R23, CR30═NOR17 NR11CR24═NOR17, S(O)mR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom;
• p represents 0 or 1;
• m represents 0, 1, or 2;
• R30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a halogen atom, OR35, NR36R37, or a hydrogen atom;
• R35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);
• R17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;
• R11, R24, R36, and R37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
• R12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group J, a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a hydrogen atom, or S(O)2R23;
• R23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s) or a phenyl group optionally substituted with one or more substituent(s) selected from Group D;
• RH11a and R12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E;
• R13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;
• R14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), or a phenyl C1-C3 alkyl wherein, the phenyl moiety in said phenyl C1-C3 alkyl group optionally being substituted with one or more substituent(s) selected from Group D;
• R15 and R16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);
• R31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
• R32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, S(O)2R23, or a hydrogen atom;
• A1 represents a nitrogen atom or CR4a;
• A2 represents a nitrogen atom or CR4b;
• A3 represents a nitrogen atom or CR4c;
• A4 represents a nitrogen atom or CR4d;
• A5 represents a nitrogen atom or CR4e:
• provided that not all of A2, A3, and A4 represent nitrogen atoms;
• R4a and R4e are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O), R41, S(O)2NR41R42, NR41R43 NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;
• when A5 represents CR4c, R4e and R1 are optionally combined with each other to form-NR45—CR41R42 representing the binding position to the nitrogen atom to which R1 is bound;
• R4b, R4c, and R4d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group X, a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, OR44, S(O), R41, S(O)2NR41R42, NR41R42 NR41C(O)R42, NR41C(O)OR42, NR41S(O)2R43, C(O)R41, C(O)OR41, C(O)NR41R42, CR42═NOR41, a hydroxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;
• provided that not all of present R4a, R4b, R4c, R4d, and R4e represent hydrogen atoms;
• k represents 0, 1, or 2;
• q represents 0, 1, or 2;
• R41 and R42 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;
• R43 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, or a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z;
• R44 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);
• R45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group W2, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group Y, a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, C(O)R46, C(O)OR46, C(O)NR46R47, or a hydrogen atom;
• and
• R46 and R47 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, or a hydrogen atom;
• Group B:
• a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a cyano group, a hydroxy group, and a halogen atom;
• Group C:
• a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), and a halogen atom;
• Group D:
• a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom;
• R21 and R22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);
• Group E:
• a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), 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 substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group C, an amino group, NHR21, NR21R22, a halogen atom, and a cyano group;
• Group H:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, OR10, NR9R10, C(O)R10, C(O)NR10R10 OC(O)R9, OC(O)OR9, NR10C(O)R9, NR10C(O)OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, and an amino group;
• R9 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s) or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s);
• R10 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
• Group J:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, and a cyano group;
• Group U:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;
• Group V:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;
• Group W:
• a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a cyano group, and a halogen atom;
• Group X:
• a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom;
• Group Y:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), and a halogen atom;
• Group Z:
• a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylamino group optionally substituted with one or more halogen atom(s), a di(C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom;
• Group W2:
• a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group Z, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group Z, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom,
• or an N-oxide thereof.