Method for producing pest control agent

A method for producing a compound represented by the following formula (I):

• [where Ar represents a phenyl group which may be substituted or a 5- to 6-membered heterocycle which may be substituted, R1 represents a C1-6 alkyl group which may be substituted, and Y represents a hydrogen atom;
• a halogen atom;
• a hydroxyl group;
• a C1-6 alkyl group which may be substituted with a halogen atom;
• a C1-6 alkyloxy group which may be substituted with a halogen atom;
• a cyano group;
• a formyl group;
• or a nitro group],
• the method comprising, as shown in the following reaction formula:
• the steps of:
• acylating an amino group at position 2 of a compound represented by formula (A) (Y has the same meaning as that described above) by use of an acylating agent represented by R1COR2 (where R1 has the same meaning as that described above, and R2 represents (1) a trifluoroacetoxy group, (2) a C1-6 alkyloxy group which may be substituted with a halogen atom or a benzyloxy group whose phenyl group may be substituted with a halogen atom, a methyl group, a cyano group, a nitro group, or a methoxy group, (3) a C1-6 alkylcarbonyloxy group which may be substituted with a halogen atom (provided that a trifluoroacetoxy group is excluded) or a phenylcarbonyloxy group whose phenyl group may be substituted with a halogen atom, a methyl group, a cyano group, a nitro group, or a methoxy group, (4) a hydroxyl group, or (5) a halogen atom) in the presence or in the absence of a compound which is at least one compound selected from the group consisting of a condensation agent, phosphorus pentoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride, oxalyl dichloride, p-toluenesulfonic acid, boron trifluoride, and a halide, a sulfate, a nitrate, or an oxide of iron, cobalt, copper, nickel, zinc, aluminium, lithium, or magnesium to thereby produce a compound represented by formula (B);
• and
• further alkylating a nitrogen atom at position 1 of the compound represented by formula (B) by use of Ar—CH2—R4 (where Ar has the same meaning as that described above, and R4 represents a halogen atom, a C1-6 alkylsulfoxy group which may be substituted with a halogen atom, or a phenylsulfoxy group which may be substituted with a halogen atom or a methyl group),
• wherein the acylation is carried out in the presence of a base.

A method for producing a compound represented by the following formula (Ia):

• [where R3 represents a halogen atom, a cyano group, a nitro group, or a trifluoromethyl group, X represents a carbon atom or a nitrogen atom, and R1a represents a halogen-substituted C1-6 alkyl group],
• the method comprising, as shown in the following reaction formula:
• the steps of:
• alkylating a nitrogen atom at position 1 of a compound represented by formula (Aa) by use of a compound represented by formula (Ca) (where R3 and X have the same meanings as those described above and R4 represents a halogen atom, a C1-6 alkylsulfoxy group which may be substituted with a halogen atom, or a phenylsulfoxy group which may be substituted with a halogen atom or a methyl group), to thereby produce a compound represented by formula (Ba);
• and
• acylating an imino group of the compound represented by formula (Ba) by use of an acylating agent represented by R1aCOR2a (where R1a has the same meaning as that described above, and R2a represents (1) a trifluoroacetoxy group, (2) a C1-6 alkyloxy group which may be substituted with a halogen atom or a benzyloxy group whose phenyl group may be substituted with a halogen atom, a methyl group, a cyano group, a nitro group, or a methoxy group, (3) a C1-6 alkylcarbonyloxy group which may be substituted with a halogen atom (provided that a trifluoroacetoxy group is excluded) or a phenylcarbonyloxy group whose phenyl group may be substituted with a halogen atom, a methyl group, a cyano group, a nitro group, or a methoxy group, (4) a hydroxyl group, or (5) a halogen atom) in the presence or in the absence of a condensation agent, phosphorus pentoxide, sulfuric acid, polyphosphoric acid, thionyl chloride, phosphorus oxychloride, or oxalyl dichloride,
• wherein the acylation is carried out in the presence of a base.