Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients
A pyridone compound represented by Formula (1): wherein R1, R2, X, Y and Z are defined. The pyridone compound can control plant diseases.
1. A compound represented by Formula (1), or a salt thereof:
wherein R1 represents
a cyano group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent A,
a C2-C6 alkenyl group optionally substituted with substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with substituent A,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with substituent A,
a C2-C6 alkenyloxy group optionally substituted with substituent A,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with substituent A,
a C3-C6 haloalkynyloxy group,
an Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 ), or
an RgC(═O)— (wherein Rg represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
R2 represents
a cyano group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent A,
a C2-C6 alkenyl group optionally substituted with substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent A,
a C2-C6 haloalkynyl group,
an Rc-L- (wherein Rc and L are the same as defined above), or
an RgC(═O)— (wherein Rg is the same as defined above);
X represents an oxygen atom or a sulfur atom;
Y represents
a phenyl group optionally substituted with 0 to 5 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyridazinyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyrimidinyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyrazinyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a triazinyl group optionally substituted with 0 to 2 R3 (with the proviso that when there are two substituents R3, they are independent to each other),
a tetrazinyl group optionally substituted with R3,
a thienyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a thiazolyl group optionally substituted with 0 to 2 R3 (with the proviso that when there are two substituents R3, they are independent to each other),
an isothiazolyl group optionally substituted with 0 to 2 R3 (with the proviso that when there are two substituents R3, they are independent to each other),
a thiadiazolyl group optionally substituted with R3,
a furanyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
an oxazolyl group optionally substituted with 0 to 2 R3 (with the proviso that when there are two substituents R3, they are independent to each other),
an isoxazolyl group optionally substituted with 0 to 2 R3 (with the proviso that when there are two substituents R3, they are independent to each other), or
an oxadiazolyl group optionally substituted with R3,
R3 represents
a hydroxyl group,
a cyano group,
a nitro group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent C,
a C2-C6 alkenyl group optionally substituted with substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent C,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with substituent C,
a C2-C6 alkenyloxy group optionally substituted with substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with substituent C,
a C3-C6 haloalkynyloxy group,
an RdC(═O)— (wherein Rd represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group)),
an RdC(═O)O— (wherein Rd is the same as defined above),
a group of a 3-6 membered ring containing 1-2 oxygen atoms,
an Rc-L- (wherein Rc and L are the same as defined above),
an RaRbN— (wherein Ra and Rb are the same as defined above), or
an ReC(═O)N(Rf)— (wherein Re and Rf are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are the same as defined above));
Z represents
a C1-C9 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent D,
a C2-C6 alkenyl group optionally substituted with substituent C,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent C,
a C2-C6 haloalkynyl group,
a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyridazinyl group optionally substituted with 0 to 3 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyrimidinyl group optionally substituted with 0 to 3 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyrazinyl group optionally substituted with 0 to 3 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a triazinyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
a tetrazinyl group optionally substituted with R4,
a thienyl group optionally substituted with 0 to 3 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a thiazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
an isothiazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
a thiadiazolyl group optionally substituted with R4,
an oxazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
an isoxazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
an oxadiazolyl group optionally substituted with R4, or
a pyrazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
R4 has the same meaning as R3; and
the substituent A is at least one member selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, an RaRbN— (wherein Ra and Rb are the same as defined above) and an Rc-L- (wherein Rc and L are the same as defined above);
the substituent B is at least one member selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
the substituent C is at least one member selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C5 alkoxyalkoxy group, an RaRbN— (wherein Ra and Rb are the same as defined above), an Rc-L- (wherein Rc and L are the same as defined above), an RdC(═O)— (wherein Rd is the same as defined above) and a group of a 3-6 membered ring containing 1-2 oxygen atoms; and
the substituent D is at least one member selected from the group consisting of a cyano group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
2. The compound, or a salt thereof according to claim 1 , wherein:
R1 represents
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent A,
a C2-C6 alkenyl group optionally substituted with substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent A,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with substituent A,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with substituent A,
a C3-C6 alkynyloxy group optionally substituted with substituent A, or
an RgC(═O)— (wherein Rg represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
R2 represents
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent A,
a C2-C6 alkenyl group optionally substituted with substituent A,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent A, or
a C2-C6 haloalkynyl group;
Y represents
a phenyl group optionally substituted with 0 to 5 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other), or
a furanyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
R3 represents
a hydroxyl group,
a cyano group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with substituent C,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with substituent C,
a C3-C6 haloalkynyloxy group,
an RdC(═O)— (wherein Rd represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group)),
an RdC(═O)O— (wherein Rd is the same as defined above), or
an Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 );
Z represents
a C1-C9 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent D,
a C2-C6 alkenyl group optionally substituted with substituent C,
a C2-C6 alkynyl group optionally substituted with substituent C,
a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
an oxazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
an isoxazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
or an oxadiazolyl group optionally substituted with R4,
R4 represents
a hydroxyl group,
a cyano group,
a nitro group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with substituent C,
a C2-C6 alkynyl group optionally substituted with substituent C,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C1-C6 haloalkoxy group,
a C2-C6 alkenyloxy group optionally substituted with substituent C,
a C3-C6 alkynyloxy group optionally substituted with substituent C,
an RdC(═O)O— (wherein Rd is the same as defined above),
an RaRbN— (wherein Ra and Rb are the same as defined above), or
an ReC(═O)N(Rf)— (wherein Re and Rf are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are the same as defined above)).
3. The compound, or a salt thereof according to claim 2 , wherein:
R1 represents
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A,
a C1-C6 haloalkyl group,
a C2-C6 alkenyl group optionally substituted with substituent A,
a C2-C6 alkynyl group optionally substituted with substituent A,
or an RgC(═O)— (wherein Rg represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
R2 represents
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent A, or
a C1-C6 haloalkyl group;
Y represents
a phenyl group optionally substituted with 0 to 5 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other), or
a furanyl group optionally substituted with 0 to 3 R3 (with the proviso that when there are two or more substituents R3, they are independent to each other),
R3 represents
a hydroxyl group,
a cyano group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C2-C6 alkenyloxy group optionally substituted with substituent C,
a C3-C6 alkynyloxy group optionally substituted with substituent C,
an RdC(═O)— (wherein Rd represents a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group)),
an RdC(═O)O— (wherein Rd is the same as defined above), or
an Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 );
Z represents
a C1-C9 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent D,
a C2-C6 alkenyl group optionally substituted with substituent C,
a C2-C6 alkynyl group optionally substituted with substituent C,
a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other),
a pyridyl group optionally substituted with 0 to 4 R4 (with the proviso that when there are two or more substituents R4, they are independent to each other), or
an isoxazolyl group optionally substituted with 0 to 2 R4 (with the proviso that when there are two substituents R4, they are independent to each other),
R4 represents
a hydroxyl group,
a cyano group,
a nitro group,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C2-C6 alkenyloxy group optionally substituted with substituent C,
a C3-C6 alkynyloxy group optionally substituted with substituent C,
an RaRbN— (wherein Ra and Rb are the same as defined above) or
an ReC(═O)N(Rf)— (wherein Re and Rf are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or an RaRbN— (wherein Ra and Rb are the same as defined above)).
4. An agricultural and horticultural pest control agent comprising the compound or a salt thereof according to claim 1 as an active ingredient.
5. An agricultural and horticultural fungicide comprising the compound or a salt thereof according to claim 1 as an active ingredient.
6. A method for controlling a plant disease, comprising applying the agricultural and horticultural pest control agent of claim 4 .
7. A method for controlling a plant disease, comprising applying the agricultural and horticultural fungicide of claim 5 .