Heterocyclic compound and harmful arthropod-controlling composition including same

1 . A compound represented by the following formula (I);

wherein:

R 2 represents a C1-C6 alkyl group optionally substituted with at least one halogen atom, a cyclopropyl group, or a cyclopropylmethyl group;

n represents 0, 1, or 2;

G 1 represents a nitrogen atom or CR 3a ;

G 2 represents a nitrogen atom or CR 3b ;

G 3 represents a nitrogen atom or CR 3c ;

G 4 represents a nitrogen atom or CR 3d ;

R 3a , R 3b , R 3c , and R 3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from Group B, a C3-C7 cycloalkyl group optionally substituted with at least one substituent selected from Group E, a phenyl group optionally substituted with at least one substituent selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with at least one substituent selected from Group H, OR 12 , NR 11 R 12 , NR 11a R 12a , NR 24 NR 11 R 12 , NR 24 OR 11 , NR 11 C(O)R 13 , NR 24 NR 11 C(O)R 13 , NR 11 C(O)OR 14 , NR 24 NR 11 C(O)OR 14 , NR 11 C(O)NR 31 R 32 , NR 24 NR 11 C(O)NR 31 R 32 , N═CHNR 31 R 32 , N=S(O) p R 15 R 16 , C(O)R 13 , C(O)OR 17 , C(O)NR 31 R 32 , C(O)NR 11 S(O) 2 R 23 , CR 30 ═NOR 17 , NR 11 CR 24 =NOR 17 , S(O) m R 23 , a cyano group, a nitro group, a hydrogen atom, or a halogen atom;

p represents 0 or 1;

m represents 0, 1, or 2;

R 30 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a halogen atom, OR 35 , NR 36 R 37 , or a hydrogen atom;

R 35 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom;

R 17 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a phenyl group optionally substituted with at least one substituent selected from Group D, or a hydrogen atom;

R 11 , R 24 , R 36 , and R 37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, or a hydrogen atom;

R 12 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from Group F, a C3-C7 cycloalkyl group optionally substituted with at least one substituent selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with at least one substituent selected from Group J, a phenyl group optionally substituted with at least one substituent selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with at least one halogen atom selected from Group D, a hydrogen atom, or S(O) 2 R 23 ;

R 23 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, or a phenyl group optionally substituted with at least one substituent selected from Group D;

R 11a and R 12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with at least one substituent selected from Group E;

R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C3-C7 cycloalkyl group optionally substituted with at least one halogen atom, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with at least one halogen atom, a phenyl group optionally substituted with at least one substituent selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with at least one substituent selected from Group D, or a hydrogen atom;

R 14 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C3-C7 cycloalkyl group optionally substituted with at least one halogen atom, a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with at least one halogen atom, or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group is optionally substituted with at least one substituent selected from Group D;

R 15 and R 16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with at least one halogen atom;

R 31 represents a C1-C6 alkyl group optionally substituted with at least one halogen atom, or a hydrogen atom;

R 32 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from Group F, a C3-C7 cycloalkyl group optionally substituted with at least one substituent selected from Group J, S(O) 2 R 23 , or a hydrogen atom;

Q represents a group represented by Q1, a group represented by Q2, a group represented by Q3, a group represented by Q4, or a group represented by Q5;

● represents the binding site to the rest of molecule;

Z represents an oxygen atom or a sulfur atom;

A 2 represents a nitrogen atom or CR 4a ;

A 3 represents a nitrogen atom or CR 4b ;

A 4 represents a nitrogen atom or CR 4c ;

A 5 represents a nitrogen atom or CR 4d ;

A 6 represents a nitrogen atom or CR 4e ;

A 7 represents a nitrogen atom or CR 4f ;

A 8 represents a nitrogen atom or CR 4g ;

A 9 represents a nitrogen atom or CR 4h ;

A 13 represents an oxygen atom, a sulfur atom, or NR 6 ;

the combination of B 1 , B 2 , B 3 , and B 4 represents:

a combination wherein B 1 represents CR 1 , B 2 represents a nitrogen atom or CR 6b , B 3 represents a nitrogen atom or CR 6c , and B 4 represents a nitrogen atom or CR 6d ;

a combination wherein B 1 represents a nitrogen atom or CR 6a , B 2 represents CR 1 , B 3 represents a nitrogen atom or CR 6c , and B 4 represents a nitrogen atom or CR 6d , provided that a combination wherein B 1 , B 2 , B 3 , and B 4 all represent CH is excluded;

a combination wherein B 1 represents a nitrogen atom or CR 6a , B 2 represents a nitrogen atom or CR 6b , B 3 represents CR 1 , and B 4 represents a nitrogen atom or CR 6 d provided that a combination wherein B 1 , B 2 , B 3 , and B 4 all represent CH is excluded;

a combination wherein B 1 represents a nitrogen atom or CR 6a , B 2 represents a nitrogen atom or CR 6b , B 3 represents CR 6c , and B 4 represents CR 1 provided that a combination wherein B 1 , B 2 , B 3 , and B 4 all represent CH is excluded; or

a combination wherein B 1 represents a nitrogen atom or CR 6a , B 2 represents CR 6b , B 3 represents a nitrogen atom, and B 4 represents CR 1 ;

R 1 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally substituted with at least one substituent selected from the group consisting of a cyano group and a halogen atom, S(O) k R 8 , OR 8 , a halogen atom, OS(O) 2 R 8 , or a hydrogen atom;

R 8 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from the group consisting of a cyano group and a halogen atom; or a C3-C4 cycloalkyl group optionally substituted with at least one substituent selected from the group consisting of a cyano group and a halogen atom;

k represents 0, 1, or 2;

R 4a , R 4b , R 4c , R 4d , R 4f , R 4g , and R 4h are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a nitro group, OR 18 , NR 18 R 19 , a cyano group, an amino group, a halogen atom, or a hydrogen atom;

R 4e represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a nitro group, OR 18 , NR 18 R 19 , a cyano group, an amino group, a halogen atom, a hydroxy group, or a hydrogen atom;

R 6a , R 6b , R 6c , and R 6d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C3-C7 cycloalkyl group optionally substituted with at least one halogen atom, a C1-C6 alkoxy group optionally substituted with at least one halogen atom, a halogen atom, or a hydrogen atom;

R 18 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom;

R 19 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, or a hydrogen atom; and

R 6 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one substituent selected from Group F, a C3-C6 cycloalkyl group optionally substituted with at least one substituent selected from Group J, a phenyl group optionally substituted with at least one substituent selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with at least one substituent selected from Group H, or a hydrogen atom;

Group B: a group consisting of a C1-C6 alkoxy group optionally substituted with at least one halogen atom, a C3-C6 alkenyloxy group optionally substituted with at least one halogen atom, a C3-C6 alkynyloxy group optionally substituted with at least one halogen atom, a C1-C6 alkylsulfanyl group optionally substituted with at least one halogen atom, a C1-C6 alkylsulfinyl group optionally substituted with at least halogen atom, a C1-C6 alkylsulfonyl group optionally substituted with at least one halogen atom, a C3-C6 cycloalkyl group optionally substituted with at least one halogen atom, 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 at least one halogen atom, a C1-C6 alkoxy group optionally substituted with at least one halogen atom, a C3-C6 alkenyloxy group optionally substituted with at least one halogen atom, a C3-C6 alkynyloxy group optionally substituted with at least one halogen atom, and a halogen atom;

Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a hydroxy group, a C1-C6 alkoxy group optionally substituted with at least one halogen atom, a C3-C6 alkenyloxy group optionally substituted with at least one halogen atom, a C3-C6 alkynyloxy group optionally substituted with at least one halogen atom, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with at least one halogen atom, a C1-C6 alkylsulfinyl group optionally substituted with at least one halogen atom, a C1-C6 alkylsulfonyl group optionally substituted with at least one halogen atom, an amino group, NHR 21 , NR 21 R 22 , C(O)R 21 , OC(O)R 21 , C(O)OR 21 , a cyano group, a nitro group, and a halogen atom;

R 21 and R 22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with at least one halogen atom;

Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C1-C6 alkoxy group optionally substituted with at least one halogen atom, a C3-C6 alkenyloxy group optionally substituted with at least one halogen atom, a C3-C6 alkynyloxy group optionally substituted with at least one halogen atom, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;

Group F: a group consisting of a CT-C6 alkoxy group optionally substituted with at least one halogen atom, a phenyl group optionally substituted with at least one substituent selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with at least one substituent selected from Group D, a C3-C7 cycloalkyl group optionally substituted with at least one halogen atom, a 3-7 membered nonaromatic heterocyclic group optionally substituted with at least one substituent selected from Group C, an amino group, NHR 21 , NR 21 R 22 , a halogen atom, and a cyano group;

Group H: a group consisting of a C1-C6 alkyl group optionally substituted with at least one halogen atom, a 5 or 6 membered aromatic heterocyclic group optionally substituted with at least one substituent selected from Group D, OR 10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 , OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , C(O)OR 10 , a halogen atom, a nitro group, a cyano group, and an amino group;

R 9 represents a C1-C6 alkyl group optionally substituted with at least one halogen atom, or a C3-C6 cycloalkyl group optionally substituted with at least one halogen atom;

R 10 represents a C1-C6 alkyl group optionally substituted with at least one halogen atom, a C3-C6 cycloalkyl group optionally substituted with at least one halogen atom, or a hydrogen atom;

Group J: a group consisting of a C1-C6 alkyl group optionally substituted with at least one halogen atom, a halogen atom, and a cyano group]

or an N-oxide thereof.

2 . The compound or an N-oxide thereof according to claim 1 , wherein

R 2 represents a C1-C6 alkyl group optionally substituted with at least one halogen atom;

G 1 represents CR 3a ;

G 2 represents CR 3b ;

G 3 represents CR 3c ;

G 4 represents CR 3d ;

R 3a , R 3b , R 3c , and R 3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C3-C7 cycloalkyl group, wherein said C3-C7 cycloalkyl group is optionally substituted with at least one substituent selected from the group consisting of a halogen atom and a cyano group, a hydrogen atom, or a halogen atom;

Q represents the group represented by Q2, the group represented by Q3, the group represented by Q4, or the group represented by Q5;

Z represents an oxygen atom;

A 4 represents a nitrogen atom;

A 5 represents CH;

A 6 represents CH;

A 7 represents a nitrogen atom;

A 8 represents CR 4g ;

the combination of B 1 , B 2 , B 3 , and B 4 represents:

a combination wherein B 1 represents a nitrogen atom or CR 6a , B 2 represents CR 1 , B 3 represents a nitrogen atom or CR 6c , and B 4 represents CR 6d ; or

a combination wherein B 1 represents CR 6a , B 2 represents CR 6b , B 3 represents CR 1 , and B 4 represents CR 6d ;

R 1 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a C3-C4 cycloalkyl group optionally substituted with at least one halogen atom, or a halogen atom; and

R 6a , R 6b , R 6c , and R 6d each represent a hydrogen atom.

3 . The compound or an N-oxide thereof according to claim 2 , wherein

Q represents the group represented by Q2 or the group represented by Q3;

the combination of B 1 , B 2 , B 3 , and B 4 represents:

a combination wherein B 1 represents CR 6a , B 2 represents CR 1 , B 3 represents CR 6c , and B 4 represents CR 6d ; or

a combination wherein B 1 represents CR 6a , B 2 represents CR 6b , B 3 represents CR 1 , and B 4 represents CR 6d ; and

R 1 represents a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, or a halogen atom.

4 . The compound or an N-oxide thereof according to claim 2 , wherein

R 3a , R 3b , R 3c , and R 3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with at least one halogen atom, a hydrogen atom, or a halogen atom.

5 . A composition for controlling a harmful arthropod comprising the compound or an N-oxide thereof of claim 1 .

6 . A composition comprising the compound or an N-oxide thereof of claim 1 , and at least one ingredient selected from the group consisting of Group (a), Group (b), Group (c), and Group (d):

Group (a): a group consisting of insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients;

Group (b): fungicidal active ingredients;

Group (c): plant growth regulatory ingredients; and

Group (d): repellent ingredients.

7 . A method for controlling a harmful arthropod, comprising applying an effective amount of the compound or an N-oxide thereof of claim 1 to a harmful arthropod or a habitat where a harmful arthropod lives.

8 . A seed or a vegetative reproductive organ comprising the compound or an N-oxide thereof claim 1 .

9 . A method for controlling a harmful arthropod, comprising applying an effective amount of the composition of claim 6 to a harmful arthropod or a habitat where a harmful arthropod lives.

10 . A seed or a vegetative reproductive organ comprising the composition of claim 6 .