Pyridone compounds and agricultural and horticultural fungicides containing said compounds as active ingredient
View Patent ↗A compound represented by Formula (1) or a salt thereof is provided. R1 represents a C1-C6 alkyl group optionally substituted, a C1-C6 haloalkyl group or the like, R2 represents a halogen atom, a C1-C6 alkyl group optionally substituted, a C1-C6 alkyloxy group optionally substituted or the like, R3 represents a hydrogen atom, a halgenatom, C1-C6 alkyl group optionally substituted or the like, n represents an integer of 0 to 5, X represents an oxygen atom or a sulfur atom, Y represents a phenyl group or a pyridyl group that is substituted with substituent at an ortho position, and the bond with a broken line indicates a double bond or a single bond.
1. A compound represented by Formula (1), or a salt thereof:
wherein R1 represents a hydroxy group,
a cyano group,
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, or
an R10R11N— (wherein R10 and R11 each independently represents a hydrogen atom or a C1-C6 alkyl group);
R2 represents a halogen atom,
a hydroxy group,
a cyano group,
a nitro group,
a C1-C6 alkyl group optionally substituted with substituent B,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent B,
a C2-C6 alkenyl group optionally substituted with substituent B,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent B,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with substituent B,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with substituent B,
a C2-C6 alkenyloxy group optionally substituted with substituent B,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with substituent B,
a C3-C6 haloalkynyloxy group,
an R20C(═O)— (wherein R20 represents a C1-C6 alkyl group, 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 R21R22N— (wherein R21 and R22 each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B1, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or R21 and R22 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 R20C(═O)O— (wherein R20 is the same as defined hereinabove),
a 3 to 6-membered ring group containing 1 to 2 oxygen atoms,
an R23-L2- (wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 is S, SO or SO 2 ),
an R21R22N— (wherein R21 and R22 are the same as defined hereinabove), or
an R24C(═O)N(R25)- (wherein R24 represents a hydrogen atom, a C1-C6 alkyl group, 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 R21R22N— (wherein R21 and R22 are the same as defined hereinabove), and R25 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B1, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
R3 represents a hydrogen atom,
a halogen atom,
a nitro group,
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 C1-C6 alkoxy group optionally substituted with substituent C,
a C1-C6 haloalkoxy group,
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,
an R30-L3- (wherein R30 has the same definition as R23, and L3 has the same definition as L2),
an R31R32N— (wherein R31 and R32 have the same definition as R21 and R22), or
an R33C(═O)— (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (with the proviso that when n is 2 or greater, the two or more R2's represent independent substituents);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group,
the phenyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 4 independent substituents D1 appropriately,
the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the triazinyl group or the tetrazinyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 3 independent substituents D1 appropriately,
the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 2 independent substituents D1 appropriately;
the bond with a broken line indicates a double bond or a single bond,
the substituent A is at least one selected from the group consisting of:
a hydroxy 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 R12R13N— (wherein R12 and R13 each independently represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or R12 and R13 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), and an R14-L1- (wherein R14 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L1 represents S, SO or SO 2 );
the substituent B is at least one selected from the group consisting of:
a hydroxy 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-C6 alkoxyalkoxy group, an R21R22N— (wherein R21 and R22 are the same as defined hereinabove), an R23-L2- (wherein R23 and L2 are the same as defined hereinabove), an R26R27R28Si— (wherein R26, R27 and R28 each independently represents a C1-C6 alkyl group), an R26R27R28Si—(CH 2 )s-O— (wherein s represents an integer of 1 to 3, and R26, R27 and R28 are the same as defined hereinabove), an R20C(═O)— (wherein R20 is the same as defined hereinabove) and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
the substituent B1 is at least one 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 selected from the group consisting of:
a hydroxy 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 R31R32N— (wherein R31 and R32 have the same definition as R21 and R22) and an R30-L3- (wherein R30 has the same definition as R14, and L3 has the same definition as L1);
the substituent D is at least one selected from the group consisting of:
a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group and a C1-C6 haloalkoxy group; and
the substituent D1 is at least one selected from the group consisting of:
a hydroxy group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
2. The compound or salt thereof according to claim 1 , wherein
R1 represents a cyano group,
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
an R10R11N— (wherein R10 and R11 each independently represents a hydrogen atom or a C1-C6 alkyl group);
R2 represents a halogen atom,
a hydroxy group,
a cyano group,
a C1-C6 alkyl group optionally substituted with substituent B,
a C1-C6 haloalkyl group,
a C1-C6 alkoxy group optionally substituted with substituent B,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with substituent B,
a C2-C6 alkenyloxy group optionally substituted with substituent B,
a C3-C6 alkynyloxy group optionally substituted with substituent B,
an R20C(═O)O— (wherein R20 represents a C1-C6 alkyl group, 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 R21R22N— (wherein R21 and R22 each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B1, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or R21 and R22 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), or
an R23-L2- (wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 represents S, SO or SO 2 );
R3 represents a hydrogen atom,
a halogen atom,
a C1-C6 alkyl group optionally substituted with substituent C,
a C3-C8 cycloalkyl group optionally substituted with substituent C,
a C1-C6 alkoxy group optionally substituted with substituent C,
a C2-C6 alkynyl group optionally substituted with substituent C, or
an R30-L3- (wherein R30 has the same definition as R23, and L3 has the same definition as L2);
Y represents a phenyl group or a pyridyl group,
the phenyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 4 independent substituents D1 appropriately, and
the pyridyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 3 independent substituents al appropriately.
3. The compound or salt thereof according to claim 2 , wherein
R1 represents a C1-C6 alkyl group optionally substituted with substituent A, or a C1-C6 haloalkyl group;
R2 represents a halogen atom, a C1-C6 alkyl group optionally substituted with substituent B, or a C1-C6 alkoxy group optionally substituted with substituent B; and
R3 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with substituent C.
4. A compound represented by Formula (2), or a salt thereof:
wherein R2 represents a halogen atom,
a hydroxy group,
a cyano group,
a nitro group,
a C1-C6 alkyl group optionally substituted with substituent B,
a C1-C6 haloalkyl group,
a C3-C8 cycloalkyl group optionally substituted with substituent B,
a C2-C6 alkenyl group optionally substituted with substituent B,
a C2-C6 haloalkenyl group,
a C2-C6 alkynyl group optionally substituted with substituent B,
a C2-C6 haloalkynyl group,
a C1-C6 alkoxy group optionally substituted with substituent B,
a C1-C6 haloalkoxy group,
a C3-C8 cycloalkoxy group optionally substituted with substituent B,
a C2-C6 alkenyloxy group optionally substituted with substituent B,
a C2-C6 haloalkenyloxy group,
a C3-C6 alkynyloxy group optionally substituted with substituent B,
a C3-C6 haloalkynyloxy group,
an R20C(═O)— (wherein R20 represents a C1-C6 alkyl group, 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 R21R22N— (wherein R21 and R22 each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B1, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or R21 and R22 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 R20C(═O)O— (wherein R20 is the same as defined hereinabove),
a 3 to 6-membered ring group containing 1 to 2 oxygen atoms,
an R23-L2- (wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 represents S, SO or SO 2 ),
an R21R22N— (wherein R21 and R22 are the same as defined hereinabove), or
an R24C(═O)N(R25)- (wherein R24 represents a hydrogen atom, a C1-C6 alkyl group, 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 R21R22N— (wherein R21 and R22 are the same as defined hereinabove), and R25 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B1, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
R3 represents a hydrogen atom,
a halogen atom,
a nitro group,
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 C1-C6 alkoxy group optionally substituted with substituent C,
a C1-C6 haloalkoxy group,
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,
an R30-L3- (wherein R30 has the same definition as R23, and L3 has the same definition as L2),
an R31R32N— (wherein R31 and R32 have the same definition as R21 and R22), or
an R33C(═O)— (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (with the proviso that when n is 2 or greater, the two or more R2's represent independent substituents);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group,
the phenyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 4 independent substituents D1 appropriately, the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the triazinyl group or the tetrazinyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 3 independent substituents D1 appropriately, and the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with substituent D at an ortho position and is further substituted with 0 to 2 independent substituents D1 appropriately,
the substituent B is at least one selected from the group consisting of:
a hydroxy 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-C6 alkoxyalkoxy group, an R21R22N— (wherein R21 and R22 are the same as defined hereinabove), an R23-L2- (wherein R23 and L2 are the same as defined hereinabove), an R26R27R28Si— (wherein R26, R27 and R28 each independently represents a C1-C6 alkyl group), an R26R27R28Si—(CH 2 )s-O— (wherein s represents an integer of 1 to 3, and R26, R27 and R28 are the same as defined hereinabove), an R20C(═O)— (wherein R20 is the same as defined hereinabove) and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
the substituent B1 is at least one 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 selected from the group consisting of:
a hydroxy 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 R31R32N— (wherein R31 and R32 have the same definition as R21 and R22) and an R30-L3- (wherein R30 has the same definition as R23, and L3 has the same definition as L2);
the substituent D is at least one selected from the group consisting of:
a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group and a C1-C6 haloalkoxy group; and
the substituent D1 is at least one selected from the group consisting of:
a hydroxy group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
5. An agricultural and horticultural pest control agent comprising the compound or salt thereof described in claim 1 as an active ingredient.
6. An agricultural and horticultural fungicide comprising the compound or salt thereof described in claim 1 as an active ingredient.
7. A method for treating or preventing a plant disease, comprising applying the agricultural and horticultural pest control agent described in claim 5 to a plant, a plant seed, or a soil for plant cultivation.