Parasitic pest control agents comprising pyridone compounds as active ingredients and methods for using the same
A compound of formula (1) or a salt thereof, which is effective as a parasitic pest control agent, is provided. In the formula, R1 represents, for example an optionally substituted C1-C6 alkyl group, a C1-C6 haloalkyl group, R2 represents, for example a halogen atom, an optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 alkoxy group, R3 represents, for example a hydrogen atom, a halogen atom, an optionally substituted C1-C6 alkyl group, n represents an integer of 0 to 5, X represents an oxygen atom or sulfur atom, Y represents, for example phenyl substituted at an ortho position, pyridyl, and the bond with a broken line represents a double bond or a single bond.
1. A method for controlling parasitic pests, wherein the method comprises administering a parasitic pest control agent to an animal in need thereof, wherein the parasitic pest control agent comprises a compound of Formula (1) or a salt thereof as an active ingredient:
wherein
R1 represents a hydroxyl 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
a R10R11N— group wherein R10 and R11 each independently represents a hydrogen atom or a C1-C6 alkyl group;
R2 represents a halogen atom,
a hydroxyl 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,
a R20C(═O)—group 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 a R21R22N— group 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 together with the nitrogen atom to which they are bonded form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl,
a R20C(═O)O— group wherein R20 is the same as defined hereinabove,
a 3 to 6-membered ring group containing 1 to 2 oxygen atoms,
a R23-L2- group wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 represents S, SO or SO 2 ,
a R21R22N— group wherein R21 and R22 are the same as defined hereinabove, or
a R24C(═O)N(R25)—group 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 a R21R22N— group 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,
a R30-L3- group wherein R30 has the same definition as R23, and L3 has the same definition as L2,
a R31R32N— group wherein R31 and R32 have the same definition as R21 and R22 or
a R33C(═O)—group 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 represent independent substituents;
X represents an oxygen atom or a sulfur atom;
Y represents phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl or thiadiazolyl,
the phenyl is substituted with substituent D at an ortho position and is optionally further substituted with 0 to 4 independent substituents D1,
the pyridyl, the pyrazinyl, the pyrimidinyl, the pyridazinyl, the triazinyl or the tetrazinyl is substituted with substituent D at an ortho position and is optionally further substituted with 0 to 3 independent substituents D1,
the thienyl, the thiazolyl, the isothiazolyl or the thiadiazolyl is substituted with substituent D at an ortho position and is optionally further substituted with 0 to 2 independent substituents D1;
the bond with a broken line represents a double bond or a single bond,
the substituent A is at least one 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 R12R13N— group 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 together with the nitrogen atom to which they are bonded form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl, and a R14-L1- group 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 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-C6 alkoxyalkoxy group, a R21R22N— group wherein R21 and R22 are the same as defined hereinabove, a R23-L2- group wherein R23 and L2 are the same as defined hereinabove, a R26R27R28Si— group wherein R26, R27 and R28 each independently represents a C1-C6 alkyl group, a R26R27R28Si—(CH 2 )s—O—group wherein s represents an integer of 1 to 3, and R26, R27 and R28 are the same as defined hereinabove, a R20C(═O)—group 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 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 R31R32N— group wherein R31 and R32 have the same definition as R21 and R22 and a R30-L3- group 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 hydroxyl 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 method according to claim 1 , wherein the parasitic pest is an insect pest of the order Acarina or nematodes.
3. The method according to claim 1 , wherein the parasitic pest is animal parasitic nematodes.
4. The method according to claim 1 , wherein the parasitic pest is nematodes of the order Spirurida.
5. The method according to claim 1 , wherein the parasitic pest is a heartworm.
6. The method 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
a R10R11N— group wherein R10 and R11 each independently represents a hydrogen atom or a C1-C6 alkyl group;
R2 represents a halogen atom,
a hydroxyl 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,
a R20C(═O)O—group 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 a R21R22N— group 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 together with the nitrogen atom to which they are bonded form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl, or
a R23-L2- group 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
a R30-L3- group wherein R30 has the same definition as R23, and L3 has the same definition as L2;
Y represents phenyl or pyridyl,
the phenyl is substituted with substituent D at an ortho position and is optionally further substituted with 0 to 4 independent substituents D1, and
the pyridyl is substituted with substituent D at an ortho position and is optionally further substituted with 0 to 3 independent substituents D1.
7. The method according to claim 1 , 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.