Amide derivative, pest control agent containing the amide derivative, and pest controlling method

1. A compound represented by the following Formula (1):

wherein:

A represents a carbon atom, a nitrogen atom, an oxidized nitrogen atom, or a sulfur atom;

K represents a non-metal atom group necessary for forming a cyclic linking group derived from benzene, pyridine, pyridine-N-oxide, or thiazole, in combination with A and two carbon atoms to which A bonds;

X represents a hydrogen atom, a halogen atom, a cyano group, or a nitro group, and when there are plural X's, each X may be the same as or different from each other;

n represents an integer of from 1 to 4;

T represents —C(═G 1 )-Q 1 ,

wherein G 1 represents an oxygen atom, and

Q 1 represents a phenyl group which may have a substituent, a naphthyl group which may have a substituent, or a heterocyclic group which may have a substituent, the substituent of a phenyl group which may have a substituent, a naphthyl group which may have a substituent, and a heterocyclic group which may have a substituent represents one or more substituents selected from a group consisting of:

a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a nitro group, and a cyano group, and when there are two or more substituents, the substituents may be the same as or different from each other,

the heterocyclic group in Q 1 represents a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, or a pyrazinyl group;

Q 2 represents a group represented by the following Formula (2) or a pyrazolyl group which may have a substituent;

the substituent of a pyrazolyl group which may have a substituent represents one or more substituents selected from a group consisting of:

a halogen atom, a C1-C6 alkyl group and a C1-C6 haloalkyl group, and when there are two or more substituents, the substituents may be the same as or different from each other;

wherein Y 1 and Y 5 each independently represent a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkylsulfonyl group;

Y 3 represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group; and

Y 2 and Y 4 each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group;

G 3 represents an oxygen atom;

R 1 and R 2 each independently represent a hydrogen atom, a C1-C4 alkyl group, or a group represented by -L-D, provided that at least either one of R 1 or R 2 represents a group represented by -L-D, wherein, L represents —C(M 1 )(M 2 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—, or —C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—C(M 7 )(M 8 )—;

M 1 to M 8 each independently represent a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a hydroxy group, a carbamoyl group, or a C1-C4 alkyl group which may have a substituent;

D represents

—C(═O)OU 1 , —C(═O)U 2 , —C(═O)NU 3 U 4 ,

—NU 5 C(═O)U 6 , —S—U 7 , —S(═O)U 8 , —S(═O)(═O)U 9 ,

—S(═O)(═O)NU 10 U 11 , —OU 12 , —NU 13 U 14 , —C(═NU 15 )U 16 , —NU 17 —C(═NU 18 )U 19 , or —C≡N;

U 1 to U 19 each independently represent

a hydrogen atom, a hydroxy group, an amino group, a cyano group, a nitro group,

a C1-C6 alkyl group which may have a substituent,

a C2-C7 alkoxycarbonyl group,

a C2-C7 haloalkoxycarbonyl group,

a C2-C7 alkylcarbonyl group,

a C1-C3 alkylamino group,

a phenyl group, or a heterocyclic group; and

U 3 and U 4 , U 5 and U 6 , U 10 and U 11 , U 12 and L, U 13 and U 14 , U 15 and U 16 , and U 17 to U 19 may be linked with each other to form a saturated heterocyclic group.

2. The compound according to claim 1 , wherein in the Formula (1):

R 1 represents a group represented by -L-D;

R 2 represents a hydrogen atom or a C1-C4 alkyl group;

D represents —C(═O)NU 3 U 4 , —S(═O)U 8 , —S(═O)(═O)U 9 , or —S(═O)(═O)NU 10 U 11 , and

U 3 , U 4 , U 8 , U 9 , U 10 , and U 11 each independently represent a hydrogen atom, a hydroxy group, a C1-C4 alkyl group, a C2-C7 alkoxycarbonyl group, or a C2-C7 haloalkoxycarbonyl group.

3. The compound according to claim 2 , wherein the compound represented by the Formula (1) is represented by the following Formula (4a):

wherein in the Formula (4a), Q 1 represents a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent; Y 1 and Y 5 each independently represent a halogen atom or a C1-C3 haloalkyl group; Y 2 and Y 4 represent a hydrogen atom; Y 3 represents a C3-C4 perfluoroalkyl group; and R 1 and R 2 have the same definitions as R 1 and R 2 , respectively, in the Formula (1).

4. The compound according to claim 2 , wherein D in the Formula (1) represents —C(═O)NU 3 U 4 , —S(═O)(═O)U 9 , or —S(═O)(═O)NU 10 U 11 .

5. The compound according to claim 4 , wherein the compound represented by the Formula (1) is represented by the following Formula (4b):

wherein in the Formula (4b), Q 1 represents a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent; Y 1 and Y 5 each independently represent a halogen atom or a C1-C3 haloalkyl group; Y 2 and Y 4 represent a hydrogen atom; and Y 3 represents a C3-C4 perfluoroalkyl group.

6. A compound represented by the following Formula (6d):

wherein Y 5d represents a C1-C3 haloalkyl group; Y 1d represents a hydrogen atom, a halogen atom, a C1-C4 haloalkyl group, a C1-C4 haloalkoxy group, or a C1-C4 haloalkylsulfinyl group;

Y 3d represents a C2-C6 haloalkyl group;

Y 2d and Y 4d each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group;

R 2a represents a group represented by -L-D;

wherein L represents —C(M 1 )(M 2 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—, or—C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—C(M 7 )(M 8 )—;

M 1 to M 8 each independently represent a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a hydroxy group, a carbamoyl group, or a C1-C4 alkyl group which may have a substituent;

D represents —C(═O)OU 1 , —C(═O)U 2 , —C(═O)NU 3 U 4 , —NU 5 C(═O)U 6 , —S(═O)U 8 , —S(═O)(═O)U 9 , —S(═O)(═O)N 10 U 11 , —OU 12 , —NU 13 U 14 , —C(═NU 15 )U 16 , —NU 17 —C(═NU 18 )U 19 , or —C≡N;

U 1 to U 19 each independently represent a hydrogen atom, a hydroxy group, an amino group, a cyano group, a nitro group, a C1-C6 alkyl group which may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C2-C7 alkylcarbonyl group, a C1-C3 alkylamino group, a phenyl group, or a heterocyclic group; and

U 3 and U 4 , U 5 and U 6 , U 10 and U 11 , U 12 and L, U 13 and U 14 , U 15 and U 16 , and U 17 to U 19 may be linked with each other to form a saturated heterocyclic group.

7. A compound represented by the following Formula (6a);

wherein

A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom or a sulfur atom;

K represents a non-metal atom group necessary for forming a cyclic linking group derived from benzene, pyridine, pyridine-N-oxide or thiazole, in combination with A and two carbon atoms to which A bonds;

X represents a hydrogen atom or a halogen atom, and when there are two or more X's each X may be the same as or different from each other;

n represents 4;

G 3 represents an oxygen atom or a sulfur atom;

R 2a represents a hydrogen atom, a C1-C4 alkyl group, or a group represented by -L-D;

wherein, L represents —C(M 1 )(M 2 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—, or—C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—C(M 7 )(M 8 )—;

M 1 to M 8 each independently represent a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a hydroxy group, a carbamoyl group, or a C1-C4 alkyl group which may have a substituent;

D representing —C(═O)OU 1 , —C(═O)U 2 , —C(═O)NU 3 U 4 , —NU 5 C(═O)U 6 , —S(═O)U 8 , —S(═O)(═O)U 9 , —S(═O)(═O)NU 10 U 11 , —OU 12 , —NU 13 U 14 , —C(═NU 15 )U 16 , —NU 17 —C(═NU 18 )U 19 , or —C≡N;

U 1 to U 19 each independently represent a hydrogen atom, a hydroxy group, an amino group, a cyano group, a nitro group, a C1-C6 alkyl group which may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C2-C7 alkylcarbonyl group, a C1-C3 alkylamino group, a phenyl group, or a heterocyclic group;

wherein U 3 and U 4 , U 5 and U 6 , U 10 and U 11 , U 12 and L, U 13 and U 14 , U 15 and U 16 , and from U 17 to U 19 may be linked with each other to form a saturated heterocyclic group;

W a represents a nitro group, an amino group, or —NH—R 1a ;

R 1a , represents a hydrogen atom, a C1-C4 alkyl group, or a group represented by -L-D, wherein L and D have the same definitions as L and D, respectively, in R 2a ;

at least one of R 1a and R 2a represents a group represented by -L-D;

Y 1a and Y 5a each independently represent a halogen atom, a C1-C6 haloalkoxy group, or a C1-C3 haloalkyl group;

in a case where K forms a benzene ring together with A and two carbon atoms to which A bonds, all X's represent hydrogen atoms, R 2a represents a hydrogen atom, Y 3a represents a C3 perfluoroalkyl group, and Y 5a represents a C1-C3 haloalkyl group;

Y 2a and Y 4a each independently represent a hydrogen atom, a halogen atom, or a C1-C4 alkyl group; and

Y 3a , represents a C2-C5 haloalkyl group.

8. A compound represented by the following Formula (6c):

wherein A represents a carbon atom, an oxygen atom, a nitrogen atom, an oxidized nitrogen atom or a sulfur atom;

K represents a non-metal atom group necessary for forming a cyclic linking group derived from benzene, pyridine, pyridine-N-oxide or thiazole, in combination with A and two carbon atoms to which A bonds;

X represents a hydrogen atom or a halogen atom, and when there are two or more X's, each X may be the same as or different from each other;

n represents 4;

G 3 represents an oxygen atom or a sulfur atom;

R 2 represents a hydrogen atom, a C1-C4 alkyl group, or a group represented by -L-D;

wherein L represents —C(M 1 )(M 2 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—, —C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—, or—C(M 1 )(M 2 )—C(M 3 )(M 4 )—C(M 5 )(M 6 )—C(M 7 )(M 8 )—;

M 1 to M 8 each independently represent a hydrogen atom, a halogen atom, a cyano group, a carboxy group, a hydroxy group, a carbamoyl group, or a C1-C4 alkyl group which may have a substituent;

D representing —C(═O)OU 1 , —C(═O)U 2 , —C(═O)NU 3 U 4 , —NU 5 C(═O)U 6 , —S(═O)U 8 , —S(═O)(═O)U 9 , —S(═O)(═O)NU 10 U 11 , —OU 12 , —NU 13 U 14 , —C(═NU 15 )U 16 , —NU 17 —C(═NU 18 )U 19 , or —C≡N; and

U 1 to U 19 each independently represent a hydrogen atom, a hydroxy group, an amino group, a cyano group, a nitro group, a C1-C6 alkyl group which may have a substituent, a C2-C7 alkoxycarbonyl group, a C2-C7 haloalkoxycarbonyl group, a C2-C7 alkylcarbonyl group, a C1-C3 alkylamino group, a phenyl group, or a heterocyclic group;

wherein U 3 and U 4 , U 5 and U 6 , U 10 and U 11 , U 12 and L, U 13 and U 14 , U 15 and U 16 , and U 17 to U 19 may be linked with each other to form a saturated heterocyclic group;

Q 2 represents a phenyl group which may have a substituent or a heterocyclic group which may have a substituent;

the substituent of a phenyl group which may have a substituent and a heterocyclic group which may have a substituent represents one or more substituents selected from a group consisting of:

a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, and a C1-C6 haloalkylsulfonyl group, and when there are two or more substituents, the substituents may be the same as or different from each other,

Wc represents —NH—C(M 1 )(M 2 )—C(M 3 )(M 4 )-D;

M 1 , M 2 , M 3 , M 4 , and D have the same definitions as M 1 , M 2 , M 3 , M 4 , and D, respectively, in R 2 .

9. A pest control agent comprising the compound according to any one of claims 1 and 2 to 5 as an active ingredient.

10. A pest controlling method comprising applying the pest control agent according to claim 9 to a pest.