N-pyridylpiperidine compound, method for producing the same, and pest control agent

1. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing, the N-pyridylpiperidine compound being represented by Formula (1)

wherein

R 1 is a halogen atom, a C 1-4 haloalkyl group, a cyano group, a nitro group, or a C 1-4 alkoxycarbonyl group;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently a hydrogen atom or a C 1-4 alkyl group;

each pair of R 2 and R 8 , and R 4 and R 6 may join to form a C 1-4 alkylene group;

R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 3-8 cycloalkyl group; a C 2-6 alkenyl group; a C 2-6 alkynyl group; a C 1-6 haloalkyl group; a C 2-6 haloalkenyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms); a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of optionally halogen-substituted C 3-8 cycloalkyl, cyano, nitro, formyl, C 1-6 alkoxy, C 1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R 12 )(R 13 ) (in which R 12 and R 13 are each independently a C 1-4 alkyl group or R 12 and R 13 may join to form a C 2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups);

R 11 is a halogen atom, a C 1-6 alkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group, a C 1-4 alkoxycarbonyl group, a C 1-4 alkylcarbonyl group, a mono or di(C 1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R 14 )═NO(R 15 ) (in which R 14 is a hydrogen atom or a C 1-4 alkyl group, and R 15 is a hydrogen atom, a C 1-4 alkyl group, or a benzyl group), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 alkoxy, C 1-4 haloalkoxy, C 1-4 alkylthio, cyano, and nitro), or a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl);

X is an oxygen atom, a sulfur atom, or —SO 2 —;

m is an integer of 1 to 4, and when m is an integer of 2 or more, the R 1 's may be the same or different; and

n is an integer of 1 or 2, and when n is 2, the two R 11 's may be the same or different.

2. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing according to claim 1 , wherein the N-pyridylpiperidine compound is represented by Formula (1) in which R 1 is a halogen atom, a C 1-4 haloalkyl group, a cyano group, or a nitro group.

3. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing according to claim 2 , wherein the N-pyridylpiperidine compound is represented by Formula (1) in which R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 2-6 alkenyl group; a C 1-6 haloalkyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms); a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of formyl, C 1-6 alkoxy, phenyl group (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups).

4. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing according to claim 1 , wherein the N-pyridylpiperidine compound is represented by Formula (1) in which R 11 is a halogen atom, a C 1-6 alkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group, a C 1-4 alkoxycarbonyl group, a formyl group, —C(R 14 )═NO(R 15 ) (in which R 14 is a hydrogen atom, and R 15 is a hydrogen atom or a C 1-4 alkyl group), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 alkoxy, C 1-4 haloalkoxy, C 1-4 alkylthio, cyano, and nitro) or a heterocyclic group (optionally substituted on the heterocyclic ring with one or more halogen atoms).

5. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing according to claim 1 , wherein N-pyridylpiperidine compound is represented by Formula (1) in which X is an oxygen atom.

6. A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing, the N-pyridylpiperidine compound being represented by Formula (1)

wherein

R 1 is a halogen atom, a C 1-4 haloalkyl group, a cyano group, a nitro group, or a C 1-4 alkoxycarbonyl group;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently a hydrogen atom or a C 1-4 alkyl group;

each pair of R 2 and R 5 , and R 4 and R 6 may join to form a C 1-4 alkylene group;

R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 3-8 cycloalkyl group; a C 2-6 alkenyl group; a C 2-6 alkynyl group; a C 1-6 haloalkyl group; a C 2-6 haloalkenyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms); a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of optionally halogen-substituted C 3-8 cycloalkyl, cyano, nitro, formyl, C 1-6 alkoxy, C 1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R 12 )(R 13 ) (in which R 12 and R 13 are each independently a C 1-4 alkyl group, or R 12 and R 13 may join to form a C 2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups);

R 11 is a halogen atom, a C 1-6 alkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group, a C 1-4 alkoxycarbonyl group, a C 1-4 alkylcarbonyl group, a mono or di(C 1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R 14 )═NO(R 15 ) (in which R 14 is a hydrogen atom or a C 1-4 alkyl group, and R 15 is a hydrogen atom, a C 1-4 alkyl group, or a benzyl group), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy, C 1-4 alkylthio, cyano, and nitro), or a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl);

X is an oxygen atom, a sulfur atom, or —SO 2 —;

m is an integer of 1 to 4, and when m is two or more, the m R 1 's may be the same or different;

n is an integer of 1 or 2, and when n is 2, the two R 11 's may be the same or different;

the method comprising reacting a pyrazole compound represented by Formula (2)

wherein R 10 , R 11 , and n are as defined above, X 1 is a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylthio group, a methanesulfonyl group, a hydroxy group, or a mercapto group with a piperidine compound represented by Formula (3)

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and m are as defined above, and X 2 is a hydroxy group or a mercapto group.

7. A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing, the N-pyridylpiperidine compound being represented by Formula (1)

wherein

R 1 is a halogen atom, a C 1-4 haloalkyl group, a cyano group, a nitro group, or a C 1-4 alkoxycarbonyl group;

R 2 , R 3 , R 4 , R 5 , R 6 , R 1 , R 8 , and R 9 are each independently a hydrogen atom or a C 1-4 alkyl group;

each pair of R 2 and R 8 , and R 4 and R 6 may join to form a C 1-4 alkylene group;

R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 3-8 cycloalkyl group; a C 2-6 alkenyl group; a C 2-6 alkynyl group; a C 1-6 haloalkyl group; a C 2-6 haloalkenyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of halogen-substituted C 3-8 cycloalkyl, cyano, nitro, formyl, C 1-6 alkoxy, C 1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R 12 )(R 13 ) (in which R 12 and R 13 are each independently a C 1-4 alkyl group, or R 12 and R 13 may join to form a C 2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups);

R 11 is a halogen atom, a C 1-6 alkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group, a C 1-4 alkoxycarbonyl group, a C 1-4 alkylcarbonyl group, a mono or di(C 1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R 14 )═NO(R 15 ) (in which R 14 is a hydrogen atom or a C 1-4 alkyl group, and R 15 is a hydrogen atom, a C 1-4 alkyl group, or a benzyl group), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 alkoxy, C 1-4 haloalkoxy, C 1-4 alkylthio, cyano, and nitro), or a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl);

X is an oxygen atom, a sulfur atom, or —SO 2 —; and

m is an integer of 1 to 4, and when m is an integer of 2 or more, the m R 1 s may be the same or different;

n is an integer of 1 or 2, and when n is 2, the two R 11 s may be the same or different;

the method comprising reacting a pyrazole compound represented by Formula (4)

wherein R 10 , R 11 , and n are as defined above, and X 2 is a hydroxy group or a mercapto group

with a piperidine compound represented by Formula (5)

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and m are as defined above, and X 3 is a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylthio group, or a methanesulfonyl group.

8. A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing, the N-pyridylpiperidine compound being represented by Formula (1)

wherein

R 1 is a halogen atom, a C haloalkyl group, a cyano group, a nitro group, or a C 1-4 alkoxycarbonyl group;

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are each independently a hydrogen atom or a C 1-4 alkyl group;

each pair of R 2 and R 8 , and R 4 and R 6 may join to form a C 1-4 alkylene group;

R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 3-8 , cycloalkyl group; a C 2-6 alkenyl group; a C 2-6 alkynyl group; a C 1-6 haloalkyl group; a C 2-6 haloalkenyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms), a phenyl group (optionally each independently substituted on the phenyl ring with one or more substituents selected from the group consisting of halogen atom, C 1-4 alkyl, and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of optionally halogen-substituted C 3-8 cycloalkyl, cyano, nitro, formyl, C 1-6 alkoxy, C 1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R 12 )(R 13 ) (in which R 12 and R 13 are each independently a C 1-4 alkyl group, or R 12 and R 13 may join to form a C 2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups);

R 11 is a halogen atom, a C 1-6 alkyl group, a C 1-4 haloalkyl group, a C 1-4 hydroxyalkyl group, a C 1-4 alkoxycarbonyl group, a C 1-4 alkylcarbonyl group, a mono or di(C 1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R 14 )═NO(R 15 ) (in which R 14 is hydrogen or C 1-4 alkyl, and R 15 is hydrogen, C 1-4 alkyl, or benzyl), a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen, C 1-6 alkyl, C 1-4 haloalkyl, C 1-6 alkoxy, C 1-4 haloalkoxy, C 1-4 alkylthio, cyano, and nitro), or a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, and C 1-4 haloalkyl);

X is an oxygen atom, a sulfur atom, or —SO 2 —;

m is an integer of 1 to 4, and when in is an integer of 2 or more, the in R 1 's may be the same or different;

n is an integer of 1 or 2, and when n is 2, the two R 11 's may be the same or different;

the method comprising reacting a piperidine compound represented by Formula (6)

wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , X, and n are as defined above

with a pyridine compound represented by Formula (7)

wherein R 1 and m are as defined above, and X 3 is a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylthio group, or a methanesulfonyl group.

9. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 1 .

10. An agricultural pest control agent according to claim 9 , which is a miticide.

11. An N-pyridylpiperidine compound, an N-oxide thereof, or a salt of either of the foregoing according to claim 1 , wherein the N-pyridylpiperidine compound is represented by Formula (1) in which R 10 is a hydrogen atom; a C 1-20 alkyl group; a C 2-6 alkenyl group; a C 1-6 haloalkyl group; a C 1-6 alkylcarbonyl group; a C 1-6 alkoxycarbonyl group; a benzoyl group (optionally substituted on the phenyl group with one to five halogen atoms); a phenyl group (optionally substituted on the phenyl ring with one or more substituents each independently selected from the group consisting of halogen and C 1-4 haloalkyl); a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 haloalkyl, and optionally substituted heterocyclic groups); or a C 1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of formyl, C 1-6 alkoxy, phenyl group (optionally substituted on the phenyl ring with one or more halogen atoms), and a heterocyclic group (optionally substituted on the heterocyclic ring with one or more C 1-4 alkyl groups).

12. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 11 .

13. An agricultural pest control agent according to claim 12 , which is a miticide.

14. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 2 .

15. An agricultural pest control agent according to claim 14 , which is a miticide.

16. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 3 .

17. An agricultural pest control agent according to claim 16 , which is a miticide.

18. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 4 .

19. An agricultural pest control agent according to claim 18 , which is a miticide.

20. An agricultural pest control agent comprising as an active ingredient the N-pyridylpiperidine compound, N-oxide thereof, or a salt of either of the foregoing of claim 5 .

21. An agricultural pest control agent according to claim 20 , which is a miticide.