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

A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or salts of these compounds, the N-pyridylpiperidine compound being represented by Formula (1)

• wherein R1 is a halogen atom, a C1-4 haloalkyl group, a cyano group, a nitro group, or a C1-4 alkoxycarbonyl group;
• R2, R3, R4, R5, R6, R7, R8, and R9 are each independently a hydrogen atom or a C1-4 alkyl group;
• each pair of R2 and R8, and R4 and R6 may join to form a C1-4 alkylene group;
• R10 is a hydrogen atom;
• a C1-20 alkyl group;
• a C3-8 cycloalkyl group;
• a C2-6 alkenyl group;
• a C2-6 alkynyl group;
• a C1-6 haloalkyl group;
• a C2-6 haloalkenyl group;
• a C1-6 alkylcarbonyl group;
• a C1-6 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, C1-4 alkyl, and C1-4 haloalkyl);
• a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C1-4 alkyl, C1-4 haloalkyl, and optionally substituted heterocyclic groups);
• or a C1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of optionally halogen-substituted C3-8 cycloalkyl, cyano, nitro, formyl, C1-6 alkoxy, C1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R12)(R13) (in which R12 and R13 are each independently a C1-4 alkyl group, or R12 and R13 may join to form a C2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and heterocyclic groups (optionally substituted on the heterocyclic ring with one or more C1-4 alkyl groups);
• R11 is a halogen atom, a C1-6 alkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group, a C1-4 alkoxycarbonyl group, a C1-4 alkylcarbonyl group, a mono or di(C1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R14)═NO(R15) (in which R14 is a hydrogen atom or a C1-4 alkyl group, and R15 is a hydrogen atom, a C1-4 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, C1-6 alkyl, C1-4 haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4 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, C1-4 alkyl, and C1-4 haloalkyl);
• X is an oxygen atom, a sulfur atom, or —SO2—;
• m is an integer of 1 to 4, and when m is two or more, the m R1's may be the same or different;
• n is an integer of 1 or 2, and when n is 2, the two R11's may be the same or different;
• the method comprising reacting a pyrazole compound represented by Formula (2)
• wherein R10, R11, and n are as defined above, X1 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 R1, R2, R3, R4, R5, R6, R7, R8, R9, and m are as defined above, and X2 is a hydroxy group or a mercapto group.

A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or salts of these compounds, the N-pyridylpiperidine compound being represented by Formula (1)

• wherein R1 is a halogen atom, a C1-4 haloalkyl group, a cyano group, a nitro group, or a C1-4 alkoxycarbonyl group;
• R2, R3, R4, R5, R6, R7, R8, and R9 are each independently a hydrogen atom or a C1-4 alkyl group;
• each pair of R2 and R8, and R4 and R6 may join to form a C1-4 alkylene group;
• R10 is a hydrogen atom;
• a C1-20 alkyl group;
• a C3-8 cycloalkyl group;
• a C2-6 alkenyl group;
• a C2-6 alkynyl group;
• a C1-6 haloalkyl group;
• a C2-6 haloalkenyl group;
• a C1-6 alkylcarbonyl group;
• a C1-6 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, C1-4 alkyl, and C1-4 haloalkyl);
• a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C1-4 alkyl, C1-4 haloalkyl, and optionally substituted heterocyclic groups);
• or a C1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of halogen-substituted C3-8 cycloalkyl, cyano, nitro, formyl, C1-6 alkoxy, C1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R12)(R13) (in which R12 and R13 are each independently a C1-4 alkyl group, or R12 and R13 may join to form a C2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and heterocyclic groups (optionally substituted on the heterocyclic ring with one or more C1-4 alkyl groups);
• R11 is a halogen atom, a C1-6 alkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group, a C1-4 alkoxycarbonyl group, a C1-4 alkylcarbonyl group, a mono or di(C1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R14)═NO(R15) (in which R14 is a hydrogen atom or a C1-4 alkyl group, and R15 is a hydrogen atom, a C1-4 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, C1-6 alkyl, C1-4 haloalkyl, C1-6 alkoxy, C1-4 haloalkoxy, C1-4 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, C1-4 alkyl, and C1-4 haloalkyl);
• X is an oxygen atom, a sulfur atom, or —SO2—;
• and
• m is an integer of 1 to 4, and when m is an integer of 2 or more, the m R1s may be the same or different;
• n is an integer of 1 or 2, and when n is 2, the two R11s may be the same or different;
• the method comprising reacting a pyrazole compound represented by Formula (4)
• wherein R10, R11, and n are as defined above, and X2 is a hydroxy group or a mercapto group
• with a piperidine compound represented by Formula (5)
• wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, and m are as defined above, and X3 is a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylthio group, or a methanesulfonyl group.

A method of producing an N-pyridylpiperidine compound, an N-oxide thereof, or salts of these compounds, the N-pyridylpiperidine compound being represented by Formula (1)

• wherein R1 is a halogen atom, a C1-4 haloalkyl group, a cyano group, a nitro group, or a C1-4 alkoxycarbonyl group;
• R2, R3, R4, R5, R6, R7, R8, and R9 are each independently a hydrogen atom or a C1-4 alkyl group;
• each pair of R2 and R8, and R4 and R6 may join to form a C1-4 alkylene group;
• R10 is a hydrogen atom;
• a C1-20 alkyl group;
• a C3-8 cycloalkyl group;
• a C2-6 alkenyl group;
• a C2-6 alkynyl group;
• a C1-6 haloalkyl group;
• a C2-6 haloalkenyl group;
• a C1-6 alkylcarbonyl group;
• a C1-6 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, C1-4 alkyl, and C1-4 haloalkyl);
• a heterocyclic group (optionally substituted on the heterocyclic ring with one or more substituents each independently selected from the group consisting of halogen, C1-4 alkyl, C1-4 haloalkyl, and optionally substituted heterocyclic groups);
• or a C1-4 alkyl group substituted with one or more substituents each independently selected from the group consisting of optionally halogen-substituted C3-8 cycloalkyl, cyano, nitro, formyl, C1-6 alkoxy, C1-4 haloalkoxy, benzyloxy, phenoxy, —CON(R12)(R13) (in which R12 and R13 are each independently a C1-4 alkyl group, or R12 and R13 may join to form a C2-7 alkylene group), phenyl (optionally substituted on the phenyl ring with one or more halogen atoms), and heterocyclic groups (optionally substituted on the heterocyclic ring with one or more C1-4 alkyl groups);
• R11 is a halogen atom, a C1-6 alkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group, a C1-4 alkoxycarbonyl group, a C1-4 alkylcarbonyl group, a mono or di(C1-4 alkyl)aminocarbonyl group, a nitro group, a cyano group, a formyl group, —C(R14)═NO(R15) (in which R14 is hydrogen or C1-4 alkyl, and R15 is hydrogen, C1-4 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, C1-6 alkyl, C1-4 haloalkyl, C1-6 alkoxy, C1-4 haloalkoxy, C1-4 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, C1-4 alkyl, and C1-4 haloalkyl);
• X is an oxygen atom, a sulfur atom, or —SO2—;
• m is an integer of 1 to 4, and when m is an integer of 2 or more, the m R1's may be the same or different;
• n is an integer of 1 or 2, and when n is 2, the two R11's may be the same or different;
• the method comprising reacting a piperidine compound represented by Formula (6)
• wherein R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, X, and n are as defined above
• with a pyridine compound represented by Formula (7)
• wherein R1 and m are as defined above, and X3 is a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylthio group, or a methanesulfonyl group.