Method for producing (alkylsulfonyl)pyridine derivative

Abstract

According to the present invention, by reacting an (alkylsulfonyl)pyridinecarbonitrile derivative with an aminopyridine derivative in the presence of a Lewis acid to directly produce the amidine derivative and converting the same into an N-substituted amidine derivative, and by further producing a diazole heterocyclic compound therefrom, the compound having a pest-controlling action can be produced with a small number of steps.

Description

Method for producing (alkylsulfonyl)pyridine derivatives

[0001] The present invention relates to a method for producing (alkylsulfonyl)pyridine derivatives that have pest control effects.

[0002] Heterocyclic compounds having sulfur-containing substituents that have pest control effects are known. For example, amidine compounds having sulfur-containing substituents are disclosed in Patent Documents 1 to 4. Patent Document 5 discloses diazole heterocyclic compounds having sulfur-containing substituents. The usefulness of these (alkylsulfonyl)pyridine derivatives has been recognized.

[0003] In obtaining (alkylsulfonyl)pyridine derivatives that have pest control effects, the production of amidine compounds containing (alkylsulfonyl)pyridine is important. Patent documents 1 to 4 describe methods for synthesizing N-substituted amidine heterocyclic compounds having alkylsulfonyl groups. Patent document 5 describes a method for synthesizing diazole heterocyclic compounds having alkylsulfonyl groups by cyclizing N-substituted amidine heterocyclic compounds with a carbonylating agent. In all of these patents, synthesizing N-substituted amidine heterocyclic compounds having alkylsulfonyl groups from pyridine carbonitride derivatives requires several steps, including hydrolysis, oxidation, and amide condensation reactions, starting from 3-(alkylthio)pyridine carbonitride derivatives. In addition, oxidation after the synthesis of N-substituted amidine heterocyclic compounds reduces the yield due to the formation of pyridine N-oxide, a byproduct.

[0004] As a method for synthesizing amidine heterocyclic compounds from amine derivatives and nitrile derivatives, for example, Patent Document 1, Non-Patent Document 1, and Non-Patent Document 3 describe a method for synthesizing amidine heterocyclic compounds by reacting an amine derivative and a nitrile derivative with a base in the presence of an inert solvent. On the other hand, Patent Document 1 and Non-Patent Documents 1 to 3 describe a method for synthesizing amidine compounds by reacting an amine derivative and a nitrile derivative in the presence of a Lewis acid. For example, Patent Document 1 describes a method for producing an amidine derivative using trimethylaluminum from an alkylthio)pyridinecarbonitrile derivative.

[0005] Furthermore, in obtaining a diazole heterocyclic compound having a sulfur-containing substituent, there is a method that involves producing an amide oxime compound containing (alkylsulfonyl)pyridine. As a method for producing an amide oxime heterocyclic compound, Patent Document 2 describes a method in which an amide compound containing (alkylsulfonyl)pyridine is chlorinated using carbon tetrachloride and triphenylphosphine, and then reacted with an aqueous solution of hydroxylamine. In this method, synthesizing the amide oxime heterocyclic compound required a lengthy process involving hydrolysis, oxidation, amide condensation, chlorination, and oximation from a pyridine carbonitride derivative. Patent Document 5 also describes a method for synthesizing a diazole heterocyclic compound having an alkylsulfonyl group by cyclizing the amide oxime heterocyclic compound with a carbonylating agent.

[0006] Regarding methods for synthesizing amidooxime heterocyclic compounds from amine derivatives and amidine derivatives, for example, Patent Document 6 describes a method in which a salt of the amine derivative and an amidine derivative are reacted in aqueous methanol. Non-Patent Document 4 describes a method in which a salt of the amine derivative and an amidine derivative are reacted in water. Furthermore, Non-Patent Document 5 describes a method in which a salt of the amine derivative and an amidine derivative are reacted in acetonitrile in the presence of triethylamine.

[0007] Furthermore, heterocyclic compounds having sulfur-containing substituents that function as pest control agents for harmful arthropods are known. Patent Document 5 discloses a 1,2,4-oxadiazole-5(4H)-one derivative having a heterocyclic group with a sulfur-containing substituent. Patent Document 5 discloses a method for producing the 1,2,4-oxadiazole-5(4H)-one derivative by reacting a hydroxyimidamide derivative with carbonyldiimidazole in tetrahydrofuran. Non-Patent Documents 6 and 7 describe a method for synthesizing the 1,2,4-oxadiazole-5(4H)-one derivative by reacting a hydroxyimidamide derivative with ethyl chloroformate in xylene in the presence of triethylamine.

[0008] International Publication No. 2020 / 054712, International Publication No. 2021 / 177410, International Publication No. 2022 / 259985, Japanese Patent Publication No. 2023-031268, International Publication No. 2023 / 190286, U.S. Patent No. 6787294

[0009] J. Org. Chem. , 2014, 79, 4687-4693. J. Med. Chem. , 2002, 45, 4655-4668J. Org. Chem. , 2020, 85, 4687-4693J. Org. Chem. , 2016, 128, 745-752 Chemistry Select. , 2019, 4, 8791-8796 Phosphorus, Sulfur and Silicon and the Related Elements (2007), 182 (2), 299-313 Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2015), 149, 920-927

[0010] The object of the present invention is to provide a novel method for producing (alkylsulfonyl)pyridine-N-substituted amidine derivatives represented by formula (1) or (alkylsulfonyl)pyridine-oxadiazole heterocyclic derivatives represented by formula (6).

[0011] The present invention relates to, but is not limited to, the following Inventions 1 to 17. [Invention 1] A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (1), comprising: [In formula (1), R ２ , R ３ , R ４ and R ５ are each independently a hydrogen atom, a halogen atom, a C １～６ alkyl group which may have a substituent, a C ２～６ alkenyl group which may have a substituent, a C ２～６ alkynyl group which may have a substituent, a C ３～６ cycloalkyl group which may have a substituent, a C １～６ alkoxy group which may have a substituent, a C ２～６ alkenyloxy group which may have a substituent, a C ２～６ alkynyloxy group which may have a substituent, a C ３～６ cycloalkoxy group which may have a substituent, a C １～６ alkylcarbonyl group which may have a substituent, a C ３～６ cycloalkylcarbonyl group which may have a substituent, a C １～６ alkoxycarbonyl group which may have a substituent, a C ２～６ alkenyloxycarbonyl group which may have a substituent, a C ２～６ alkynyloxycarbonyl group which may have a substituent, a C １～６ alkylcarbonyloxy group which may have a substituent, a C ２～６ alkenylcarbonyloxy group which may have a substituent, a C ２～６ alkynylcarbonyloxy group which may have a substituent, a C １～６ alkylthio group, a C １～６ alkylsulfinyl group which may have a substituent, a C １～６ alkylsulfonyl group which may have a substituent, a C １～６Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２(This is synonymous with the above), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ R represents a group selected from the group consisting of cycloalkylcarbonyl groups. ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６An alkynylcarbonyloxy group, a C which may have a substituent １～６ An alkylthio group, a C which may have a substituent １～６ An alkylsulfinyl group, a C which may have a substituent １～６ An alkylsulfonyl group, a C which may have a substituent １～６ An alkylsulfonyloxy group, a phenyl group which may have a substituent, a heterocyclic group which may have a substituent, a phenoxy group which may have a substituent, a pyridyloxy group which may have a substituent, NY １ Y ２ Group, C(O)NY １ Y ２ Group, C(=NY ２ )Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxy group, trimethylsilyl group, C(O)NH ２ Group and SF ５ Group selected from the group consisting of (Y １ , Y ２ , and Y ３ is as defined above)] The following steps: [Step A] An aminopyridine derivative represented by formula (2) [In formula (2), R ２ , R ３ , R ４ and R ５ are as defined above] and an (alkylsulfonyl)pyridinecarbonitrile derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ are as defined above] are reacted in the presence of a Lewis acid to obtain an amidine derivative represented by formula (4) [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄStep A includes obtaining the amidine derivative represented by formula (4) and the amine compound represented by formula (5). [In formula (5), R ６ By reacting with [which is synonymous with the above], the (alkylsulfonyl)pyridine derivative represented by formula (1) is obtained. [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and also, R ａ , R ｂ , R ｃ and R ｄ Step B, which includes obtaining [which is the same as above]; a manufacturing method comprising: [Invention 2] A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (6), [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents１～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents.２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step A] Aminopyridine derivative represented by formula (2) [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ [This is synonymous with the above] is reacted in the presence of a Lewis acid to obtain an amidine derivative represented by formula (4). [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄStep A, which includes obtaining [the same as above]; and Step B, which includes obtaining an amidine derivative represented by formula (4) and an amine compound represented by formula (5). [In formula (5), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ By reacting with a group selected from the group consisting of cycloalkylcarbonyl groups, a (alkylsulfonyl)pyridine derivative represented by formula (1) is obtained. [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and R ａ , R ｂ , R ｃ and R ｄ Step B includes obtaining [which is the same as above]; and [Step C] reacting a (alkylsulfonyl)pyridine derivative represented by formula (1) with a carbonylating agent to obtain a (alkylsulfonyl)pyridine derivative represented by formula (6). [In formula (6), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ A manufacturing method comprising step C to obtain (i) an aminopyridine derivative represented by formula (2). [Invention 3] Step A is (i) an aminopyridine derivative represented by formula (2). [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and Rｄ The method for producing an aminopyridine derivative represented by formula (2) is the same as above, comprising the steps of: (ii-a) reacting in solution in the presence of a Lewis acid; and (ii-a) mixing the reaction solution with an alcohol-containing basic aqueous solution after the reaction is complete. [Invention 4] Step A is (i) an aminopyridine derivative represented by formula (2) [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ The method for producing an amidine derivative represented by formula (4), comprising the steps of: (ii-b) reacting in a solution in the presence of a Lewis acid (which is the same as above); and mixing the reaction solution with an alcohol-containing acidic aqueous solution after the reaction is complete. [Invention 5] A method for producing an amidine derivative represented by formula (4), [In formula (4), R ２ , R ３ , R ４ , and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ , and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (i) an aminopyridine derivative represented by formula (2) and [In formula (2), R ２ , R ３ , R ４ , and R ５ [This is synonymous with the above] (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄA method for producing an amide oxime derivative represented by formula (1), wherein step B is a reaction carried out using a solvent containing one or more selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol. [Invention 6] A method for producing an amide oxime derivative represented by formula (1), wherein step B is a reaction carried out using a solvent containing one or more selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol. [Invention 9] A method for producing an amide oxime derivative represented by formula (1), [In formula (1), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R6 is a hydrogen atom, and C may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ R represents a group selected from the group consisting of cycloalkylcarbonyl groups. ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step B] In the presence of a solvent, the amidine derivative represented by formula (4) and [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above. Amine compound represented by formula (5) [In formula (5), R６ A manufacturing method comprising step A, in which [ is synonymous with the above] reacts; [Invention 10] A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (6), [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２(This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step B] In the presence of a solvent, the amidine derivative represented by formula (4) and [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above. Amine compound represented by formula (5) [In formula (5), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ A group selected from the group consisting of cycloalkylcarbonyl groups is reacted to form an amide oxime derivative represented by formula (1). [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and R ａ , R ｂ , R ｃ and R ｄStep A, which includes obtaining [the same as above]; and Step C, which includes reacting an amide oxime derivative represented by formula (1) with a carbonylating agent to obtain a (alkylsulfonyl)pyridine derivative represented by formula (6). [In formula (6), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ A manufacturing method comprising step B to obtain [which is the same as above]. [Invention 11] The manufacturing method according to Invention 9 or 10, wherein the solvent in [Step A] is a solvent comprising one or more selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol. [Invention 12] In [Step C], the carbonylating agent is a halogenated carbamate compound represented by formula (7): [In the formula R Ｘ C may have substituents. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６[Invention 13] The manufacturing method according to Invention 12, wherein the reaction in [Step C] is carried out in a solvent containing water. [Invention 14] The manufacturing method according to Invention 13, wherein the reaction solvent in [Step C] is a mixed solvent containing an amide solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone, and an aromatic hydrocarbon or a halogenated aliphatic hydrocarbon. [Invention 15] A method for producing a 1,2,4-oxadiazole-5(4H)-one derivative of formula (6), which is: [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The hydroxyimidamide derivative represented by formula (1a): [In formula (8), R ２ , R ３ , R ４ , R ５ , R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above, and the halogenated carbamate compound represented by formula (7): [In the formula R Ｘ C may have substituents. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent.２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ A method for producing a product, wherein X represents a group selected from the group consisting of an alkynyloxycarbonyl group, an optionally substituted phenyl group, and an optionally substituted heterocyclic group, and X represents one of fluorine, chlorine, bromine, and iodine, in the presence of a base selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonides, alkaline earth metal carbonides, alkali metal alkoxides, alkaline earth metal alkoxides, alkali metal metal hydrides, and alkaline earth metal hydrides. [Invention 16] The production method according to Invention 15, wherein the reaction is carried out in a solvent containing water. [Invention 17] The production method according to Invention 15 or 16, wherein the reaction solvent is a mixed solvent containing an amide solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, and an aromatic hydrocarbon or a halogenated aliphatic hydrocarbon.

[0012] The present invention provides a method for producing a (alkylsulfonyl)pyridine-N-substituted amidine derivative represented by formula (1) or a (alkylsulfonyl)pyridine-oxadiazole heterocyclic derivative represented by formula (6) that has pest control activity. In particular, since the amidine derivative represented by formula (4) can be directly produced using the (alkylsulfonyl)pyridine derivative represented by formula (3) as a reaction substrate, an amidine derivative or oxadiazole derivative having an alkylsulfonyl group that has pest control activity can be produced in a short number of steps. In this specification, "to directly produce (synthesize)..." means that the production (synthesis) is carried out without the recovery of an intermediate. Furthermore, an amide oxime derivative having an alkylsulfonyl group that has pest control activity can be directly produced from the corresponding amidine derivative, and the amide oxime derivative having pest control activity, and the oxadiazole derivative produced therefrom, can be produced in a short number of steps. Moreover, oxadiazole derivatives can be obtained in high yield from the amide oxime derivative having an alkylsulfonyl group.

[0013] Next, the present invention will be described. One aspect of the present invention is a method for producing a (alkylsulfonyl)pyridine-N-substituted amidine derivative represented by formula (1) (hereinafter also referred to as compound (1)) or a (alkylsulfonyl)pyridine-oxadiazole derivative represented by formula (6) (hereinafter also referred to as compound (6)).

[0014] Another embodiment includes a method for producing a (alkylsulfonyl)pyridine-amidine derivative represented by formula (4) (hereinafter also referred to as compound (4)), which is a precursor of compound (1) and compound (6).

[0015] The substituents in compound (1), compound (6), and compound (4) will be described below. ２ , R ３ , R ４ and R ５ Each of these may independently contain a hydrogen atom, a halogen atom, or a substituent.１～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ２～６ C, which may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C, which may have an alkynyloxy group or substituent. ３～６ C may have a cycloalkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. ３～６ A cycloalkylcarbonyl group, which may have substituents. １～６ C may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ C may have an alkynylcarbonyloxy group or substituent. １～６ C may have an alkylthio group or substituent. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５Represents a group selected from the group consisting of the above Y. １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ The Y represents a group selected from the group consisting of alkyl groups. ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group consisting of (Y １ and Y ２ (This is equivalent to the above.) The substituents that may be present include halogen atoms and C １～６ Alkoxy group, Halo C １～６ Alkoxy group, C ３～６ Cycloalkoxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF５ A group can be mentioned. When there are two or more substituents, each substituent may be the same or different from the others.

[0016] Preferably, R ２ , R ３ , R ４ and R ５ Each of these may independently contain a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ３～６ C may have a cycloalkoxy group or substituent. １～６ C may have an alkylthio group or substituent. １～６ C which may have an alkylsulfinyl group and substituents. １～６ This represents a group selected from the group consisting of alkylsulfonyl groups. In this case, the substituents that may be present are halogen atoms, C １～６ Alkoxy group, Halo C １～６ Alkoxy group, cyano group, nitro group, hydroxy group, mercapto group, amino group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF ５ Examples include R. ２ and R ５ is a hydrogen atom, R ３ and R ４ Each of these may independently have a hydrogen atom, a halogen atom, and a substituent. １～６ A group selected from the group consisting of alkyl groups. Particularly preferred is R ２ and R ５ is a hydrogen atom, R ３ and R ４ C may have a substituent on either side. １～６ It is an alkyl group, and the other is a hydrogen atom. In this case, the substituents that may be present are halogen atoms, C １～６ Alkoxy group, Halo C １～６Alkoxy group, cyano group, nitro group, hydroxy group, mercapto group, amino group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF ５ The basis is cited.

[0017] The aforementioned R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ A group selected from the group consisting of cycloalkyl groups. Optional substituents include halogen atoms and C １～６ Alkoxy group, Halo C １～６ Alkoxy group, C ３～６ Cycloalkoxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF ５ Examples include groups. When there are two or more substituents, each substituent may be the same or different from the others. Preferably, R ａ C may have substituents. １～６ It is an alkyl group. More preferably, R ａ C may be substituted with halogen atoms. １～３ It is an alkyl group, and more preferably a methyl group or an ethyl group.

[0018] R ｂ , R ｃ and R ｄ Each of these may independently contain a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ２～６ C, which may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６C may have an alkenyloxy group or substituent. ２～６ C, which may have an alkynyloxy group or substituent. ３～６ C may have a cycloalkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. ３～６ A cycloalkylcarbonyl group, which may have substituents. １～６ C may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ C may have an alkynylcarbonyloxy group or substituent. １～６ C may have an alkylthio group or substituent. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ and Y ３ (This is the same as above.) The substituents that may be present are halogen atoms, C １～６ Alkoxy group, Halo C １～６ Alkoxy group, C ３～６ Cycloalkoxy group, NY １ Y２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF ５ A group can be mentioned. When there are two or more substituents, each substituent may be the same or different from the others.

[0019] Preferably, R ｂ , R ｃ and R ｄ Each of these may independently contain a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ３～６ C may have a cycloalkoxy group or substituent. １～６ C may have an alkylthio group or substituent. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ This represents a group selected from the group consisting of an alkylsulfonyl group, an optionally substituted phenyl group, an optionally substituted heterocyclic group, an optionally substituted phenoxy group, and an optionally substituted pyridyloxy group. In this case, the optionally substituted atoms are halogen atoms, C １～６ Alkoxy group, Halo C １～６ Alkoxy group, cyano group, nitro group, hydroxy group, mercapto group, amino group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ Examples include R. ｂ and R ｄ is a hydrogen atom, R ｃ C may have halogen atoms and substituents. １～６ C may have alkyl groups or substituents. ３～６ Cycloalkyl groups, C which may have substituents １～６C may have an alkoxy group or substituent. ３～６ The group is selected from the group consisting of a cycloalkoxy group, an optionally substituted phenyl group, and an optionally substituted heterocyclic group. In this case, the optionally substituted groups are a halogen atom, a cyano group, a nitro group, a hydroxyl group, a mercapto group, an amino group, a carboxyl group, a trimethylsilyl group, and C(O)NH ２ Base, and SF ５ A base is mentioned. More preferably, R ｂ and R ｄ is a hydrogen atom, R ｃ C may have substituents. ３～６ The group is selected from the group consisting of cycloalkyl groups, optionally substituted phenyl groups, and optionally substituted heterocyclic groups. In this case, the optionally substituted groups are halogen atoms, C １～６ Alkoxy group, Halo C １～６ Alkoxy group, cyano group, nitro group, hydroxy group, mercapto group, amino group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, SF ５ The basis is cited.

[0020] R ２ , R ３ , R ４ and R ５ , and R ｂ , R ｃ and R ｄ Preferred forms of the "phenyl group which may have substituents" in this context include 3-fluorophenyl group, 3-chlorophenyl group, 3-bromophenyl group, 3-iodophenyl group, 3-cyanophenyl group, 3-(trifluoromethyl)phenyl group, 3-(trifluoromethoxy)phenyl group, 4-fluorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4-iodophenyl group, 4-cyanophenyl group, 4-(trifluoromethyl)phenyl group, 4-(trifluoromethoxy)phenyl group, 4-cyclopropylphenyl group, 4-(1-cyanocyclopropyl)phenyl group, 2,4-difluorophenyl group, 2,4,6-trifluorophenyl group, and 3,5-difluorophenyl group.

[0021] R ２ , R ３ , R ４ and R ５ , and R ｂ , R ｃ and R ｄExamples of "heterocyclic groups" in this context include thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazole-2-yl, oxazole-4-yl, oxazole-5-yl, isoxazole-3-yl, isoxazole-4-yl, isoxazole-5-yl, isoxazolin-3-yl, isoxazolin-4-yl, isoxazolin-5-yl, thiazole-2-yl, thiazole-4-yl, thiazole-5-yl, isothiazo Isothiazol-3-yl, isothiazole-4-yl, isothiazole-5-yl, pyrazole-1-yl, pyrazole-3-yl, pyrazole-4-yl, pyrazole-5-yl, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, 1,3,4-oxadiazole-2-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl, 1,3,4-thiadiazole-2-yl, 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl, 1,2,4-triazole-1-yl 1,2,4-triazole-3-yl, 1,2,4-triazole-5-yl, 1,2,3-thiadiazole-4-yl, 1,2,3-thiadiazole-5-yl, 1,2,3-triazole-1-yl, 1,2,3-triazole-2-yl, 1,2,3-triazole-4-yl, 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl, 1,2,3,4-tetrazol-5-yl, pyridine-2-yl, pyridine-3-yl, pyridine-4-yl, pyrimidine-2-yl, pyrimidine-4-yl, pyrimidine-5 -yl, pyrazine-2-yl, pyridazine-3-yl, pyridazine-4-yl, 1,3,5-triazine-2-yl, 1,2,4-triazine-3-yl, 1,2,4-triazine-5-yl, 1,2,4-triazine-6-yl, benzothiophene-2-yl, benzothiophene-3-yl, benzothiophene-4-yl, benzothiophene-5-yl, benzothiophene-6-yl, benzothiophene-7-yl, benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl,Benzofuran-7-yl, indole-1-yl, indole-2-yl, indole-3-yl, indole-4-yl, indole-5-yl, indole-6-yl, indole-7-yl, benzothiazole-2-yl, benzothiazole-4-yl, benzothiazole-5-yl, benzothiazole-6-yl, benzothiazole-7-yl, benzimidazole-1-yl, benzimidazole-2-yl, benzimidazole-4-yl, benzimidazole-5-yl, benzimidazole-6-yl, benzimidazole-7-yl, Benzoisoxazole-3-yl, Benzoisoxazole-4-yl, Benzoisoxazole-5-yl, Benzoisoxazole-6-yl, Benzoisoxazole-7-yl, Benzoisothiazol-3-yl, Benzoisothiazol-4-yl, Benzoisothiazol-5-yl, Benzoisothiazol-6-yl, Benzoisothiazol-7-yl, Indazole-1-yl, Indazole-3-yl, Indazole-4-yl, Indazole-5-yl, Indazole-6-yl, Indazole-7-yl, Benzoisoxazole-2-yl Benzoxazole-4-yl, Benzoxazole-5-yl, Benzoxazole-6-yl, Benzoxazole-7-yl, Quinoline-2-yl, Quinoline-3-yl, Quinoline-4-yl, Quinoline-5-yl, Quinoline-6-yl, Quinoline-7-yl, Quinoline-8-yl, Isoquinoline-1-yl, Isoquinoline-3-yl, Isoquinoline-4-yl, Isoquinoline-5-yl, Isoquinoline-6-yl, Isoquinoline-7-yl, Isoquinoline-8-yl, Quinoxaline-2-yl, Quinoxaline-3-yl, Quinoxaline-5-yl Examples include quinoxaline-6-yl, quinoxaline-7-yl, quinoxaline-8-yl, phthalazine-1-yl, phthalazine-4-yl, phthalazine-5-yl, phthalazine-6-yl, phthalazine-7-yl, phthalazine-8-yl, cinnoline-3-yl, cinnoline-4-yl, cinnoline-5-yl, cinnoline-6-yl, cinnoline-7-yl, cinnoline-8-yl, quinazolin-2-yl, quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl, or quinazolin-8-yl.

[0022] The above-mentioned R ６ is a group selected from the group consisting of a hydrogen atom, a C １～６ alkyl group which may have a substituent, a C ３～６ cycloalkyl group which may have a substituent, a C １～６ alkylcarbonyl group, and a C ３～６ cycloalkylcarbonyl group which may have a substituent. Note that the substituent which may be present includes a halogen atom, a C １～６ alkoxy group, a halo C １～６ alkoxy group, a C ３～６ cycloalkoxy group, a NY １ Y ２ group, a C(O)NY １ Y ２ group, a C(=NY ２ )Y ３ group, a cyano group, a nitro group, a hydroxy group, a mercapto group, an amino group, a formyl group, a carboxy group, a trimethylsilyl group, a C(O)NH ２ group, and a SF ５ group. When two or more substituents are present, the respective substituents may be the same as or different from each other. Preferably, R ６ is a hydrogen atom or a C １～６ alkylcarbonyl group which may have a substituent. More preferably, R ６ is a hydrogen atom, a C １～６ alkylcarbonyl group or a halo C １～６ alkylcarbonyl group.

[0023] In the compounds represented by formula (2), formula (3), and formula (5) described later, R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ , and R ６ have the same meanings as described above.

[0024] A first aspect of the present invention relates to a method for producing compound (1) or compound (6), comprising a production step of directly synthesizing compound (4) by reacting an aminopyridine derivative represented by formula (2) (also referred to as compound (2)) with an (alkylsulfonyl)pyridinecarbonitrile derivative represented by formula (3) (also referred to as compound (3)). Specifically, the production method comprises: [Step A]: a step of directly synthesizing compound (4) by reacting compound (2) and compound (3); and then [Step B]: a step of synthesizing compound (1) by reacting compound (4) with an amine compound represented by formula (5) (also referred to as compound (5)). Furthermore, the production method comprises [Step C]: a step of synthesizing compound (6) by reacting compound (1) with a carbonylating agent, following [Step B]. The production method is described below.

[0025] [Step A] By reacting an aminopyridine derivative represented by formula (2) (compound (2)) with an (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) (compound (3)) in the presence of a Lewis acid, an amidine derivative represented by formula (4) (compound (4)) can be produced.

[0026] The Lewis acid used in [Step A] of this invention, and the method for producing it, will be described below. As the Lewis acid, Ti(Y ４ ) ４ Ni(Y ４ ) ２ , Zn(Y ４ ) ２ , Cu(Y ４ ) ２ , Co(Y ４ ) ２ , Al(Y ４ ) ３ , Sn(Y ４ ) ４ , Si(Y ４ ) ４ , and B(Y ４ ) ３ One or more compounds selected from the group consisting of [Y ４ Each of these elements may independently contain a hydrogen atom, a halogen atom, a hydroxyl group, or a substituent. １～６ C may have alkyl groups or substituents.１～６ Examples include groups selected from the group consisting of alkoxy groups. ４ C may have hydrogen atoms, halogen atoms, and substituents. １～６ It is preferable to select from the group consisting of alkyl groups, and more preferably to include at least a halogen atom—preferably a chlorine atom. A more specific Lewis acid is TiCl. ４ NiCl ２ ZnCl ２ CuCl ２ CoCl ２ Transition metal compounds such as the following—preferably transition metal halides—AlCl ３ AlEt ２ Cl, SnCl ４ Typical metal compounds such as typical metal compounds—preferably typical metal halides—SiHCl ３ BF ３ Examples of nonmetallic compounds include metalloid compounds, more preferably nonmetallic or metalloid halides, and preferably those in which the oxidation state of the central metal is 4, but are not limited to this. Preferred Lewis acids include titanium tetrachloride (TiCl). ４ ), dichlorotitanium diisopropoxide (Ti(O ｉ Pr) ２ Cl ２ ), Titanium (IV) Tetraisopropoxide (Ti(O ｉ Pr) ４ Titanium compounds such as ) and SnCl ４ It is one or more compounds selected from the group consisting of tin compounds such as the following. More preferably, titanium tetrachloride (TiCl ４ The amount of Lewis acid used is usually 0.1 to 10 moles, preferably 0.5 to 5 moles, and more preferably 1.0 to 2 moles, per mole of compound (2).

[0027] The reaction between compound (2) and compound (3) may be carried out in the presence of a solvent. Examples of solvents include, but are not limited to, water; aromatic hydrocarbon solvents such as benzene, chlorobenzene, and toluene; halogenated aliphatic hydrocarbon solvents such as chloroform, dichloromethane, and 1,2-dichloroethane; alcohol solvents such as methanol, ethanol, and 1-butanol; nitrile solvents such as acetonitrile and propylnitrile; aromatic heterocyclic solvents such as pyridine; sulfoxide solvents such as dimethyl sulfoxide and sulfolane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether solvents such as tetrahydrofuran, diethyl ether, and 1,4-dioxane; or mixed solvents thereof. Preferably, the solvent is a halogenated aliphatic hydrocarbon solvent or an aromatic hydrocarbon solvent. The amount of solvent used is usually 1 to 100 parts by mass, preferably 1 to 20 parts by mass, relative to compound (3). A more preferred amount of solvent is 2 to 10 parts by mass. This is usually done by mixing compound (2) and compound (3) with a Lewis acid.

[0028] The reaction temperature for the reaction between compound (2), compound (3), and the reactant is usually 10 to 200°C, preferably 20 to 150°C. The reaction is preferably carried out under a nitrogen atmosphere. The reaction time is usually 0.1 to 100 hours, preferably 0.1 to 24 hours.

[0029] The reaction between compound (2), compound (3), and Lewis acid may be carried out in the presence of a base. Examples of bases include, but are not limited to, pyridine compounds such as pyridine and 4-dimethylaminopyridine; tertiary amine compounds such as triethylamine and ethyldiisopropylamine; and carbonates such as sodium bicarbonate, sodium carbonate, and potassium carbonate. Preferably, the base is a tertiary amine compound or a pyridine compound. The amount of base used is usually 0.1 to 20 moles, preferably 0.1 to 10 moles, per mole of compound (3).

[0030] A preferred method for introducing the Lewis acid is to introduce it into an inert solvent containing compound (2) and compound (3). A more preferred method for introducing the Lewis acid is to introduce it when compound (2) and compound (3) are completely dissolved in the inert solvent.

[0031] As a post-reaction treatment method for [Step A], after the reaction between compound (2), compound (3), and Lewis acid is complete, the reaction is stopped by mixing the resulting reaction mixture with an alcohol-containing basic aqueous solution. The alcohol is C １～６ It is preferable that the alcohol is a lower alcohol. The alcohol may be one type or a mixture of two or more miscible types. Examples of alcohols include methanol, ethanol, 1-propanol, isopropanol, 1-butanol, isobutanol, t-butanol, etc., but are not limited to these. Preferably, it is a lower alcohol selected from methanol, ethanol, 1-propanol, and isopropanol. The amount of lower alcohol used is usually 1 to 50 moles, preferably 1 to 20 moles, per mole of compound (3). Examples of the base in the basic aqueous solution include pyridine compounds such as pyridine and 4-dimethylaminopyridine; tertiary amine compounds such as triethylamine and ethyldiisopropylamine; carbonates such as sodium bicarbonate, sodium carbonate, and potassium carbonate; hydroxide salts such as lithium hydroxide and sodium hydroxide, etc., but are not limited to these. Preferably, the base is a bicarbonate, a carbonate, or a hydroxide. The amount of base used in the basic aqueous solution is usually 0.1 to 20 moles, preferably 1 to 10 moles, per mole of compound (3).

[0032] Another method for post-reaction treatment in [Step A] is to stop the reaction by mixing the resulting reaction mixture with an alcohol-containing acidic aqueous solution after the reaction between compound (2), compound (3), and Lewis acid is complete. The alcohol is C １～６It is preferable that the alcohol is a lower alcohol. The lower alcohol may be one type or a mixture of two or more miscible types. Examples of alcohols include methanol, ethanol, 1-propanol, isopropanol, 1-butanol, isobutanol, t-butanol, etc., but are not limited to these. Preferably, the alcohol is selected from methanol, ethanol, 1-propanol, and isopropanol. The amount of alcohol used is usually 1 to 50 moles, preferably 1 to 20 moles, per mole of compound (3). Examples of the acid in the acidic aqueous solution include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid; and organic acids such as acetic acid, methanesulfonic acid, and p-toluenesulfonic acid, but are not limited to these. Alternatively, an alcohol-containing acidic aqueous solution may be prepared by using an acid such as hydrogen chloride generated in the reaction solution by the Lewis acid used, and adding the reaction solution to aqueous alcohol.

[0033] One method for extracting compound (4) from the reaction mixture is to concentrate the mixture after the reaction is complete, for example, to extract compound (4) from the resulting reaction mixture. The extracted reaction mixture may be used directly in [Step B], or it may be purified by liquid-liquid separation, filtration, etc. Alternatively, compound (4) may be isolated from the reaction mixture by conventional purification methods such as washing, filtration, column chromatography, and recrystallization.

[0034] [Step B] Compound (4) can be reacted with an amine compound represented by formula (5) (compound (5)) to produce compound (1) which has pest control properties.

[0035]

[0036] The reagent in [Step B] of the present invention and the method of production will be described below. Compound (5) is a hydroxylamine or O-substituted hydroxylamine derivative represented by formula (5) [R ６ The above is true. Compound (5) may be an elemental amine compound, a solution dissolved in water, or a salt. Examples of salts include hydrochloride salts and sulfate salts.

[0037] The reaction between compound (5) and compound (4) may be carried out in the presence of a solvent. Examples of solvents include, but are not limited to, water; aromatic hydrocarbon solvents such as benzene, chlorobenzene, and toluene; halogen-containing aliphatic hydrocarbon solvents such as chloroform, dichloromethane, and 1,2-dichloroethane; alcohol solvents such as methanol, ethanol, isopropanol, and 1-butanol; nitrile solvents such as acetonitrile and propylnitrile; aromatic heterocyclic solvents such as pyridine; sulfoxide solvents such as dimethyl sulfoxide and sulfolane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether solvents such as tetrahydrofuran, diethyl ether, and 1,4-dioxane; or mixed solvents thereof. The amount of solvent used is usually 1 to 100 parts by mass, preferably 1 to 20 parts by mass, relative to compound (4). A more preferred amount of solvent is 2 to 10 parts by mass. The reaction is usually carried out by mixing compound (4) and compound (5).

[0038] Preferably, an alcohol solvent is used, and it is preferable to use a solvent containing one or more alcohols selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol. More preferably, the solvent contains one or more alcohols selected from methanol, ethanol, isopropanol, and 1-butanol. When an alcohol solvent is used, it may be a mixed solvent with another solvent that is miscible with the alcohol. In that case, the mixing ratio (volume) of the alcohol solvent and the other solvent is preferably 1:9 to 9:1, and more preferably 1:5 to 5:1.

[0039] The reaction temperature for the reaction between compound (4) and compound (5) is usually 10 to 200°C, preferably 20 to 150°C. The reaction is preferably carried out under a nitrogen atmosphere. The reaction time is usually 0.1 to 100 hours, preferably 0.1 to 24 hours.

[0040] The reaction between compound (4) and compound (5) may be carried out in the presence of a base. Examples of bases include, but are not limited to, pyridine compounds such as pyridine and 4-dimethylaminopyridine; tertiary amine compounds such as triethylamine and ethyldiisopropylamine; and carbonates such as sodium bicarbonate, sodium carbonate, and potassium carbonate. The amount of base used is usually 1 to 20 moles, preferably 1 to 10 moles, per mole of compound (4).

[0041] As a method for separating compound (1) from the reaction mixture, after the reaction is complete, compound (1) can be separated from the resulting reaction mixture by, for example, concentration. Alternatively, compound (1) may be isolated from the reaction mixture by conventional purification methods such as washing, filtration, column chromatography, and recrystallization. When producing compound (6), the separated reaction mixture may be used directly in [Step C], or it may be purified by liquid-liquid separation, filtration, chromatography, recrystallization, etc., before being subjected to [Step C] described later.

[0042] [Step C] A (alkylsulfonyl)pyridine derivative represented by formula (6) (hereinafter referred to as compound (6)) can be produced from compound (1).

[0043] The carbonylating agent in step C of the present invention and the method of production will be described below. Step C involves compound (1) and R ６ Compound (6) can be produced by reacting an N-hydroxyamidine derivative (compound 1a), in which the atom is a hydrogen atom, with a carbonylating agent. Therefore, when applying the present invention to the production of compound (6), compound 5 represented by formula (5) is R ６ It is preferable to use hydroxylamine, which has a hydrogen atom, to produce an N-hydroxyamidine derivative (compound 1a) and apply it to step C. ６ If compound (1) is used, which is an alkyl group or acyl group, it is necessary to convert it to an N-hydroxyamidine derivative (compound 1a) by an appropriate method.

[0044] Examples of carbonylating agents include, but are not limited to, 1,1-carbonyldiimidazole and halogenated carbamate compounds such as methyl chloroformate, ethyl chloroformate, phenyl chloroformate, and 4-nitrophenyl chloroformate. The amount of carbonylating agent used is usually 1 to 20 moles, preferably 1 to 5 moles, per mole of compound (1a).

[0045] The reaction between compound (1a) and the carbonylating agent may be carried out in the presence of a solvent. Examples of solvents include, but are not limited to, water; aromatic hydrocarbon solvents such as benzene, chlorobenzene, and toluene; halogen-containing aliphatic hydrocarbon solvents such as chloroform, dichloromethane, and 1,2-dichloroethane; alcohol solvents such as methanol, ethanol, and 1-butanol; nitrile solvents such as acetonitrile and propylnitrile; aromatic heterocyclic solvents such as pyridine; sulfoxide solvents such as dimethyl sulfoxide and sulfolane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether solvents such as tetrahydrofuran, diethyl ether, and 1,4-dioxane; or mixed solvents thereof. The amount of solvent used is usually 1 to 100 parts by mass, preferably 1 to 20 parts by mass, relative to compound (1a). A more preferred amount of solvent is 2 to 10 parts by mass. The reaction is usually carried out by mixing compound (1) and the reactant.

[0046] The reaction temperature for the reaction between compound (1a) and the carbonylating agent is usually -20 to 100°C, preferably -10 to 50°C. The reaction is preferably carried out under a nitrogen atmosphere. The reaction time is usually 0.1 to 100 hours, preferably 0.1 to 24 hours.

[0047] The reaction of the compound (1a) with a carbonylating agent may be carried out in the presence of a base. Examples of the base include pyridine compounds such as pyridine and 4-dimethylaminopyridine; tertiary amine compounds such as triethylamine and ethyldiisopropylamine; carbonates such as sodium hydrogen carbonate, sodium carbonate, and potassium carbonate; hydroxide salts such as lithium hydroxide and sodium hydroxide, but are not limited thereto. The amount of the base used is usually 1 to 20 moles, preferably 1 to 10 moles, per 1 mole of the compound (1a).

[0048] As another aspect of the method for producing the compound (6), [Step C-b]: The 1,2,4-oxadiazol-5(4H)-one derivative (compound (6)) can be produced by reacting the compound (1a) with a carbamate halide compound (7) in the presence of a base. That is, it is a step of using a carbamate halide compound (7) as a carbonylating agent in the presence of a base.

[0049]

[0050] In formula (7), R Ｘ represents an optionally substituted C １～６ alkyl group, an optionally substituted C ２～６ alkenyl group, an optionally substituted C ２～６ alkynyl group, an optionally substituted C ３～６ cycloalkyl group, an optionally substituted C １～６ alkylcarbonyl group, an optionally substituted C ３～６ cycloalkylcarbonyl group, an optionally substituted C １～６ alkoxycarbonyl group, an optionally substituted C ２～６ alkenyloxycarbonyl group, an optionally substituted C ２～６ alkynyloxycarbonyl group, an optionally substituted phenyl group, or an optionally substituted heterocyclic group. X represents a halogen atom and represents any one of fluorine, chlorine, bromine, and iodine. Preferably, R Ｘ represents an optionally substituted C １～６ alkyl group, an optionally substituted C２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group and a substituent. ３～６ Represents a group selected from the group consisting of cycloalkyl groups. Ｘ The substituents that may be present in include halogen atoms and NY １ Y ２ Base, C(O)NY １ Y ２ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, C(O)NH ２ group, trimethylsilyl group, SF ５ Group (Y １ and Y ２ (This is synonymous with the above.) When there are two or more substituents, each substituent may be the same or different from the others. Preferably, a halogen atom, C １～６ Alkoxy groups, and halo C １～６ It is a group selected from the group consisting of alkoxy groups.

[0051] Specific examples of halogenated carbamate compounds represented by general formula (7) include methyl formate halide, ethyl formate halide, isopropyl formate halide, butyl formate halide, octyl formate halide, phenyl formate halide, 4-chlorophenyl formate halide, and 4-nitrophenyl formate halide. As the halide or halogenated product, chlorides and bromides are preferred, with chlorides being particularly preferred due to the ease of preparation and availability of raw materials.

[0052] The amount of the halogenated carbamate compound represented by general formula (7) used is usually 1 to 20 moles, preferably 1 to 5 moles, per mole of compound (1a).

[0053] In [Step C-b], the bases include inorganic bases such as alkali metal or alkaline earth metal carbonides and alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal alkoxides, and alkali metal or alkaline earth metal metal hydrides. Examples of alkali metal or alkaline earth metal carbonides include potassium carbonate, sodium carbonate, calcium carbonate, sodium bicarbonate, potassium bicarbonate, magnesium carbonate, calcium carbonate, etc. Examples of alkali metal or alkaline earth metal hydroxides include sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, etc. Examples of alkali metal or alkaline earth metal alkoxides include sodium methoxide, sodium ethoxide, sodium-t-butoxide, potassium-t-butoxide, etc. Examples of alkali metal or alkaline earth metal metal hydrides include sodium hydride, potassium hydride, etc. The base is preferably selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonides, alkaline earth metal carbonides, alkali metal alkoxides, and alkaline earth metal alkoxides. More preferably, it is an alkali metal or alkaline earth metal hydroxide, or an alkali metal or alkaline earth metal carbonide. Inorganic bases such as alkali metal or alkaline earth metal carbonides, or their hydroxides, are advantageous in industrial production because they are low in risk, easy to handle, readily available, and inexpensive. From this viewpoint, sodium carbonate, potassium carbonate, or sodium hydroxide, potassium hydroxide are preferred as bases to be used, and sodium hydroxide or potassium hydroxide are more preferred.

[0054] The base is preferably prepared as an aqueous solution and used in the reaction. Suitable bases for the aqueous solution are hydroxides of alkali metals or alkaline earth metals, or carbonides of alkali metals or alkaline earth metals. Specifically, a 1-50% by weight aqueous solution of the base is more preferably used, and even more preferably a 5-30% by weight aqueous solution. Particularly preferred forms of the base include 5-30% by weight aqueous solutions of sodium hydroxide or potassium hydroxide, or aqueous solutions of sodium carbonate or potassium carbonate. The amount of the base used is preferably 0.1-10.0 moles, and more preferably 0.5-5.0 moles, per mole of compound (1a).

[0055] On the other hand, it is preferable that the aqueous solution of the base satisfy the above weight percentage and is added in an amount of 0.01 to 0.5 times the mass of the solvent for dissolving compound (1a).

[0056] The manufacturing method of the present invention can typically be carried out in the presence of a solvent that dissolves compound (1a). The solvent used is not particularly limited as long as it does not inhibit the reaction. Examples include, but are not limited to, water; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and mesitylene; halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene; alcohol solvents such as methanol, ethanol, and 1-butanol; nitrile solvents such as acetonitrile and propylnitrile; halogenated aliphatic hydrocarbon solvents such as methylene chloride, chloroform, and dichloroethane; aliphatic hydrocarbon solvents such as peptane, hexane, heptane, 2-methylbutane, 2-methylpentane, 2-methylhexane, cyclopentane, cyclohexane, and cycloheptane; aprotic polar solvents such as dimethyl sulfoxide and sulfolane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; ether solvents such as tetrahydrofuran, diethyl ether, 1,4-dioxane, and diisopropyl ether; and ketone solvents such as 2-butanone, or mixtures thereof. These solvents may be used as a single system or in combination as a mixed solvent system, with the mixed solvent system being more preferable. As a mixed solvent system, it is preferable to use a mixture of water and an organic solvent. Even more preferable is the mixture of water and two or more organic solvents.

[0057] Preferably, aromatic hydrocarbon solvents such as benzene, toluene, xylene, and mesitylene; halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene; halogenated aliphatic hydrocarbon solvents such as methylene chloride, chloroform, and dichloroethane; aliphatic hydrocarbon solvents such as peptane, hexane, heptane, 2-methylbutane, 2-methylpentane, 2-methylhexane, cyclopentane, cyclohexane, and cycloheptane; aprotic polar solvents such as dimethyl sulfoxide and sulfolane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; or mixed solvents thereof. More preferably, aprotic polar solvents such as dimethyl sulfoxide and sulfolane; and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone are used. The amount of solvent used should be an appropriate amount that can dissolve compound (1a), preferably 1 to 50 times the mass of compound (1a), and more preferably 2 to 30 times the mass.

[0058] More preferably, a mixed solvent comprising a water-immiscible organic solvent selected from the group consisting of aromatic hydrocarbon solvents such as benzene, toluene, xylene, and mesitylene; halogenated aromatic hydrocarbon solvents such as chlorobenzene and dichlorobenzene; halogenated aliphatic hydrocarbon solvents such as methylene chloride, chloroform, and dichloroethane; and aliphatic hydrocarbon solvents such as peptane, hexane, heptane, 2-methylbutane, 2-methylpentane, 2-methylhexane, cyclopentane, cyclohexane, and cycloheptane, and a water-miscible solvent selected from the group consisting of aprotic polar solvents such as dimethyl sulfoxide and sulfolane, and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, is preferred. As the mixed solvent, a mixed solvent of the hydrocarbon solvent, which is the aromatic hydrocarbon solvent and / or halogenated aliphatic hydrocarbon solvent, and the amide solvent is more preferred. As the aromatic hydrocarbon solvent or halogenated aliphatic hydrocarbon solvent, toluene, xylene, and methylene chloride are particularly preferred, and a mixed solvent of these with an amide solvent selected from N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone is preferred.

[0059] In the mixed solvent system, the mixing ratio is preferably such that 1 part by mass of a water-miscible solvent, such as the aprotic polar solvent or amide solvent, is mixed with 3 to 30 parts by mass of a water-immiscible solvent, such as the aromatic hydrocarbon solvent. Preferably, it is a mixed solvent of a hydrocarbon solvent, such as an aromatic hydrocarbon solvent and / or a halogenated aliphatic hydrocarbon solvent, and the amide solvent, with a mixing ratio of 1 part by mass of the amide solvent to 3 to 30 parts by mass of the hydrocarbon solvent, such as the aromatic hydrocarbon and / or a halogenated aliphatic hydrocarbon, and more preferably 1 part by mass of the amide solvent to 3 to 20 parts by mass of the hydrocarbon solvent.

[0060] In the manufacturing method of the present invention, it is preferable to contact compound (1a) and the halogenated carbamate compound (7) together in the liquid phase in the presence of the base. For example, the condensation reaction is carried out by adding the halogen compound (7) dropwise to compound (1a) and the base under an inert gas atmosphere while stirring and mixing the solvent. The dropwise addition time is preferably 0.1 to 10 hours, more preferably 0.5 to 3 hours. The reaction time after the addition is 0.1 to 5 hours, more preferably 0.5 to 2 hours. The reaction temperature is preferably -50 to 100°C, more preferably -10 to 50°C. The condensation reaction is carried out under normal pressure, under pressure, or under reduced pressure. Compound (1a) may be used in a state in which it has formed a salt with the base.

[0061] One method for extracting compound (6) from the reaction mixture is to concentrate the mixture after the reaction is complete, for example, to isolate compound (6). Alternatively, compound (6) may be isolated from the reaction mixture by conventional purification methods such as washing, filtration, column chromatography, and recrystallization.

[0062] Example 1: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (50 mg, 0.14 mmol) and 4-(trifluoromethyl)pyridine-2-amine (23.9 mg, 0.15 mmol) were dissolved in toluene (1 mL) and heated to 80°C. Various reagents (0.21 mmol) were added, and the mixture was stirred at 90°C for 3 hours. The reaction mixture after 3 hours was analyzed by high-performance liquid chromatography. The reagents used and the content (area %) of the title compound are summarized in Table 1. The high-performance liquid chromatography analysis conditions in Table 1 are described in Table 2.

[0063] Example 2: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide using isopropanol at the end of the reaction 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (60.0 g, 168.39 mmol) and 4-(trifluoromethyl)pyridine-2-amine (28.66 g, 176.81 mmol) were dissolved in toluene (381 mL) and the temperature was raised to 80°C. Titanium tetrachloride (25.85 mL, 44.71 g, 253.74 mmol) was added and the mixture was stirred at 90-100°C for 3 hours. The reaction was terminated by adding the reaction mixture dropwise to a mixed solution of isopropanol (101 mL) and sodium bicarbonate aqueous solution (water: 420 mL, sodium bicarbonate: 110 g, 1.31 mol) prepared in a separate flask. Subsequently, the residue remaining in the reaction flask was dissolved in saturated sodium bicarbonate aqueous solution (100 mL) and ethyl acetate (100 mL), and added dropwise in the same manner. Further addition of ethyl acetate (300 mL) was made, the mixture was thoroughly stirred, and then allowed to stand before liquid-liquid separation. The resulting organic layer was washed with 400 mL of water, and the resulting aqueous layer was subjected to two extractions with ethyl acetate (200 mL). The resulting organic layers were filtered together using Kiriyama filter paper (a type of suction filtration) to remove the insoluble titanium residue (titanium residue: 8.73 g). Subsequently, solvent removal and crystallization were performed to obtain 63.48 g of the target product (purity: 95.23%, yield: 69.20%). 1 H NMR(CDCl3) δ9.01(1H, d, J=2.1Hz), 8.68(1H, d, J=2.1Hz), 8.57(1H, d, J=5.4Hz), 7.74-7.69(2H, m), 7.41(2H, d, J=8.1Hz), 7.30(1H, s), 7.21(1H, dd, J=1.2, 5.3Hz), 4.07(2H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)

[0064] Example 3: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide without using isopropanol at the end of the reaction 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (60.0 g, 168.39 mmol) and 4-(trifluoromethyl)pyridine-2-amine (28.66 g, 176.81 mmol) were dissolved in toluene (381 mL) and the temperature was raised to 80°C. Titanium tetrachloride (25.85 mL, 44.71 g, 253.74 mmol) was added, and the mixture was stirred at 90-100°C for 3 hours. The reaction was terminated by dropping the reaction solution into an aqueous sodium bicarbonate solution (water: 420 mL, sodium bicarbonate: 110 g, 1.31 mol) prepared in a separate flask. Subsequently, the residue remaining in the reaction flask was dissolved in saturated sodium bicarbonate aqueous solution (100 mL) and ethyl acetate (200 mL), and added dropwise in the same manner. Another 300 mL of ethyl acetate was added, the mixture was stirred well, and then allowed to stand before liquid-liquid separation. The resulting organic layer was washed with 400 mL of water, and the resulting aqueous layer was extracted twice with ethyl acetate (200 mL). The resulting organic layer was filtered together through Kiriyama filter paper to remove the insoluble titanium residue (titanium residue: 13.14 g). After solvent removal and crystallization, 51.85 g of the target product (purity: 97.44%, yield: 57.90%) was obtained.

[0065] Example 4: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (122.0 g, 0.34 mol) and 4-(trifluoromethyl)pyridine-2-amine (58.0 g, 0.36 mol) were dissolved in toluene (760 mL) and the mixture was heated to 60°C. Titanium tetrachloride (49.0 mL, 0.45 mol) was added, and the mixture was stirred at 90°C for 4 hours. In a separate flask, an aqueous solution of sodium bicarbonate (water: 840 mL, sodium bicarbonate: 220 g) and isopropanol (200 mL) were added, and after cooling to 0-10°C, the reaction was terminated by adding the reaction solution dropwise. The residue remaining in the reaction flask was dissolved in isopropanol (220 mL) and toluene (77 mL) and added dropwise in the same manner. The mixture was stirred at room temperature for 10 minutes, then heated to 70°C, and the solution was separated. The obtained organic layer was washed with water (680 mL), and N,N-dimethylacetamide (680 mL) was added to dissolve the target solid. The insoluble titanium residue was then removed by filtration through Kiriyama filter paper. Subsequently, solvent removal and crystallization were performed to obtain 155.76 g of the target product (purity: 98.3%, yield: 87.7%).

[0066] Reference Example 1: Method for producing 3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylthio)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (30.0 g, 92.5 mmol) and 4-(trifluoromethyl)pyridine-2-amine (15.3 g, 94.35 mmol) were dissolved in toluene (345 mL) and the mixture was heated to 85°C. Titanium tetrachloride (15.2 mL, 138.75 mmol) was added, and the mixture was stirred at 85°C for 3 hours. The reaction was terminated by adding the reaction mixture dropwise to water (300 mL) prepared in a separate flask. The residue remaining in the reaction flask was then dissolved in toluene (100 mL) and added dropwise in the same manner. Another 200 mL of water was added, the mixture was stirred for 20 minutes, allowed to stand for 10 minutes, and then separated. The resulting organic layer was filtered, the filtrate was washed with water and saturated brine, separated, dried over anhydrous magnesium sulfate, and filtered. After filtration, the solution was concentrated under reduced pressure using a rotary evaporator to obtain 40.34 g of the target product (yield: 89.7%).1 H NMR(CDCl3) δ10.01(1H, br), 8.53-8.51(2H, m), 7.85(1H, br), 7.81(1H, d, J=2.1Hz), 7.67-7.62(2H, m), 7.57(1H, s), 7.37(2H, d, J=8.1Hz), 7.14(1H, dd, J=1.2, 5.3Hz), 2.98(2H, q, J=7.2Hz), 1.47(3H, t, J=7.5Hz)

[0067] Example 5: Method for producing 5-(4-chlorophenyl)-3-(ethylsulfonyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 5-(4-chlorophenyl)-3-(ethylsulfonyl)picolinonitrile (860.7 g, 2.81 mmol) and 4-(trifluoromethyl)pyridine-2-amine (478 mg, 2.95 mmol) were dissolved in toluene (8.5 mL) and the mixture was heated to 85°C. Titanium tetrachloride (25.85 mL, 44.71 g, 253.74 mmol) and toluene (1.5 mL) were added, and the mixture was stirred at 90-100°C for 4 hours. The mixture was then post-processed in the same manner as in Example 3 to obtain 1.19 g of the target product (yield: 90.3%). 1 H NMR(CDCl3) δ9.00(1H, d, J=2.1Hz), 8.67(1H, d, J=2.1Hz), 8.57(1H, d, J=5.4Hz), 7.64-7.52(4H, m), 7.30(1H, s), 7.20(1H, dd, J=0.9, 5.1Hz), 4.05(2H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)

[0068] Example 6: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (15.0 g, 42.10 mmol) and 4-(trifluoromethyl)pyridine-2-amine (7.17 g, 44.20 mmol) were dissolved in dichloromethane (95 mL). Titanium tetrachloride (6.0 mL, 54.73 mmol) was added at room temperature, and the mixture was stirred at 40°C for 4 hours. In a separate flask, 3N hydrochloric acid (63 mL) and isopropanol (42 mL) were added, and after cooling to 0-10°C, the reaction was terminated by adding the reaction mixture dropwise. The residue remaining in the reaction flask was dissolved in isopropanol (13 mL) and added dropwise in the same manner. After stirring at room temperature for 30 minutes, the mixture was separated. The aqueous layer was extracted twice with dichloromethane (20 mL), and the resulting organic layer was neutralized with water (42 mL) and 30% sodium hydroxide aqueous solution, then heated to 40°C and separated. N,N-dimethylacetamide (84 mL) was added to the obtained organic layer to dissolve the target solid, and the insoluble titanium residue was removed by filtration with Kiriyama filter paper. Subsequently, solvent removal and crystallization were performed to obtain 20.36 g of the target product (purity: 97.85%, yield: 91.28%).

[0069] Example 7: Method for producing 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)picolinonitrile (25.0 g, 70.16 mmol) and 4-(trifluoromethyl)pyridine-2-amine (11.94 g, 73.67 mmol) were dissolved in toluene (159 mL) and heated to 60°C. Titanium tetrachloride (10.0 mL, 91.21 mmol) was added, and the mixture was stirred at 90°C for 3 hours. In a separate flask, water (95 mL) and isopropanol (35 mL) were added, and the reaction was terminated by adding the reaction mixture dropwise. The residue remaining in the reaction flask was dissolved in isopropanol (35 mL) and added dropwise in the same manner. After stirring at room temperature for 30 minutes, the mixture was separated. The resulting organic layer was washed with a mixed solvent of water (70 mL) and isopropanol (35 mL) and separated. Subsequently, the obtained organic layer was neutralized with water (70 mL) and a 30% sodium hydroxide aqueous solution, and the mixture was heated to 80°C and stirred for 30 minutes. After cooling to room temperature, the obtained slurry was filtered, and the residue was washed with water (70 mL) to obtain 32.33 g of the target product (purity: 96.05%, yield: 90.53%).

[0070] Example 8: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide (38.34 g, 78.8 mmol) and hydroxylamine hydrochloride (21.90 g, 315 mmol) were dissolved in acetonitrile (500 mL). The mixture was stirred under reflux conditions for 4 hours and then filtered. Subsequently, 100 mL of the solvent was removed from the filtrate using a rotary evaporator, and 400 mL of water was added. The mixture was then filtered again, and the residue was washed three times with water (50 mL) to obtain 37.18 g of the target product. 1H NMR(CDCl3) δ8.96(1H, d, J=2.1Hz), 8.56(1H, d, J=2.1Hz), 8.17(1H, br), 7.99(1H, d, J=5.1Hz), 7.71(2H, d, J=8.4Hz), 7.40(2H, d, J=8.4Hz), 7.35(1H, br), 6.93(1H, d, J=4.8Hz), 6.75(1H, s), 3.58(2H, q, J=7.5Hz), 1.35(3H, t, J=7.5Hz)

[0071] Example 9: Method for producing 3-(5-(4-chlorophenyl)-3-(ethylsulfonyl)-pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one 5-(4-chlorophenyl)-3-(ethylsulfonyl)-N'-hydroxy-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide (35.9 g, 74.1 mol), obtained by the same method as in Example 8, was dissolved in tetrahydrofuran (300 mL) and cooled to 0°C. 1,1'-carbonyldiimidazole (17.84 g, 110 mmol) was added, and the mixture was heated to room temperature and stirred overnight. After concentration under reduced pressure, the reaction mixture was diluted with water and dichloromethane and separated. The obtained organic layer was washed with saturated ammonium chloride aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, it was concentrated under reduced pressure using a rotary evaporator. The obtained residue was suspended in n-hexane and filtered to obtain 45.15 g of the target product. 1 H NMR(CDCl3) δ9.01(1H, d, J=2.1Hz), 8.57(1H, d, J=2.1Hz), 8.34(1H, br), 8.16(1H, d, J=5.1Hz), 7.66-7.54(4H, m), 7.38(1H, dd, J=0.6, 5.1Hz), 3.51(2H, q, J=7.5Hz), 1.39(3H, t, J=7.5Hz)

[0072] Example 10: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one 39.6 g, 74.1 mmol of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picolineimidamide (39.6 g, 74.1 mmol) was dissolved in tetrahydrofuran (300 mL) and cooled to 0°C. 1,1'-carbonyldiimidazole (18.0 g, 111 mmol) was added, and the mixture was heated to room temperature and stirred overnight. After concentration under reduced pressure, the reaction mixture was diluted with water and dichloromethane and separated. The resulting organic layer was washed with saturated ammonium chloride aqueous solution and saturated brine, and dried over anhydrous magnesium sulfate. After filtration, it was concentrated under reduced pressure using a rotary evaporator. The resulting residue was purified by silica gel chromatography to obtain 35.15 g of the target product. 1 H NMR(CDCl3) δ9.02(1H, d, J=2.1Hz), 8.58(1H, d, J=2.1Hz), 8.34(1H, s), 8.15(1H, d, J=5.1Hz), 7.75-7.71(2H, m), 7.43(2H, d, J=8.1Hz), 7.38(1H, d, J=5.1Hz), 3.52(2H, q, J=7.5Hz), 1.39(3H, t, J=7.5Hz)

[0073] Example 11: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide (500 mg, 0.96 mmol) was dissolved in methanol (10 mL). Hydroxylamine hydrochloride (335 mg, 4.82 mmol) was added, and the mixture was stirred under reflux conditions for 4 hours. The compounds in the reaction system after 4 hours were analyzed by high-performance liquid chromatography, and the results are summarized in Table 3.

[0074] Examples 12-18: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide The title compound was produced by changing the solvent in the method of production in Example 12 to the solvent listed in Table 3. The compounds in the reaction system after 4 hours of reaction were analyzed by high-performance liquid chromatography, and the results are summarized in Table 3.

[0075] The high-performance liquid chromatography analysis conditions for Examples 11 to 18 are shown in Table 4.

[0076] Example 19: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 23.05 g, 44.47 mmol of 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide was dissolved in a mixed solvent of toluene (89 mL) and methanol (45 mL). Hydroxylamine hydrochloride (4.63 g, 66.71 mmol) was added, and the mixture was stirred at 70°C for 5 hours. After 5 hours of reaction, the compounds in the reaction system were analyzed by high-performance liquid chromatography under the conditions shown in Table 4. The area% of the starting material was 0.49%, and the area% of the target product was 98.63%.

[0077] Example 20: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 10.61 g, 20.45 mmol of 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide was dissolved in a mixed solvent of toluene (40 mL) and isopropanol (20 mL). Hydroxylamine hydrochloride (2.13 g, 30.68 mmol) was added, and the mixture was stirred at 85°C for 7 hours. After 7 hours of reaction, the compounds in the reaction system were analyzed by high-performance liquid chromatography under the conditions shown in Table 2. The area% of the starting material was 0.10%, and the area% of the target product was 99.59%.

[0078] Example 21: Method for producing 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide 10.0 g, 19.3 mmol of 3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide was dissolved in 58 mL of 1-butanol. Hydroxylamine hydrochloride (2.01 g, 29.0 mmol) was added, and the mixture was stirred at 85°C for 8 hours. The mixture was then cooled to 60°C, water (19 mL) was added, and the mixture was allowed to stand before being separated. Again, water (19 mL) was added at 60°C, and the pH of the aqueous layer was adjusted to 7 with a 12% NaOH aqueous solution, and the mixture was separated. N,N-dimethylacetamide (12 mL) was added to the obtained organic layer, and after concentration under reduced pressure, crystallization was performed to obtain 10.10 g of the target product (purity: 94.4%, yield: 92.4%). 1H NMR(CDCl3) δ8.96(1H, d, J=2.1Hz), 8.56(1H, d, J=2.1Hz), 8.17(1H, br), 7.99(1H, d, J=5.1Hz), 7.71(2H, d, J=8.4Hz), 7.40(2H, d, J=8.4Hz), 7.35(1H, br), 6.93(1H, d, J=4.8Hz), 6.75(1H, s), 3.58(2H, q, J=7.5Hz), 1.35(3H, t, J=7.5Hz)

[0079] Example 22: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one Under a nitrogen atmosphere, 230.01 g, 0.43 mol of 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picoline imidamide was dissolved in a mixed solvent of 775 mL of toluene and 129 mL of N,N-dimethylacetamide and cooled to 0°C to 10°C in an ice bath. 287 g, 0.86 mol of 12% aqueous sodium hydroxide solution was added within the range of 0°C to 10°C, followed by the addition of 61 g, 0.65 mol of methyl chloroformate within the range of 0°C to 10°C, and the mixture was reacted at 0°C to 10°C for 1 hour. The organic layer was then washed with water and separated. The resulting aqueous layer was extracted with toluene. The obtained organic layers were mixed, washed with water adjusted to pH=4, and separated again. The resulting organic layers were concentrated under reduced pressure using a rotary evaporator. The resulting residue was dissolved in methanol, and water was added to precipitate crystals. The mixture was then filtered to obtain 231.05 g of the target product (yield: 98.4%). １ Based on the 1H-NMR measurement results, it was confirmed that the obtained compound is compound No. 47 described in International Publication No. 2023 / 190286 (Patent Document 1). 1H-NMR (CDCl3): δ 9.02(1H, d, J=2.1Hz), 8.58(1H, d, J=2.1Hz), 8.34(1H, s), 8.15(1H, d, J=5.1Hz), 7.75-7.71(2H, m), 7.43(2H, d, J=8.1Hz), 7.38(1H, d, J=5.1), 3.52(2H, q, J=7.5Hz), 1.39(3H, t, J=7.5Hz)

[0080] Example 23: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one Under a nitrogen atmosphere, 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picolineimidamide (0.97 g, 1.82 mmol) was dissolved in a mixed solvent of toluene (3.27 mL) and N-methylpyrrolidone (0.54 mL) and cooled to 0°C to 10°C in an ice bath. 12% aqueous sodium hydroxide solution (1.21 g, 3.63 mmol) was added dropwise, followed by methyl chloroformate (0.26 g, 2.72 mmol), and the mixture was reacted at 0°C to 10°C for 1 hour. Subsequently, water and ethyl acetate were added, and the organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate. After filtration through Kiriyama filter paper, the resulting filtrate was concentrated under reduced pressure using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography to obtain 0.98 g of the target product as amorphous material (yield 96.3%). １ Based on the 1H-NMR measurement results, it was confirmed that the obtained compound is compound No. 47 described in International Publication No. 2023 / 190286 (Patent Document 1). 1H-NMR (CDCl3): δ 9.02(1H, d, J=2.1Hz), 8.58(1H, d, J=2.1Hz), 8.34(1H, s), 8.15(1H, d, J=5.1Hz), 7.75-7.71(2H, m), 7.43(2H, d, J=8.1Hz), 7.38(1H, d, J=5.1), 3.52(2H, q, J=7.5Hz), 1.39(3H, t, J=7.5Hz)

[0081] Example 24: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one Under a nitrogen atmosphere, 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picolineimidamide (0.97 g, 1.82 mmol) was dissolved in a mixed solvent of methylene chloride (3.27 mL) and N,N-dimethylacetamide (0.54 mL), and cooled to 0°C to 10°C in an ice bath. A 12% sodium hydroxide aqueous solution (1.21 g, 3.63 mmol) was added dropwise, followed by methyl chloroformate (0.26 g, 2.72 mmol), and the mixture was reacted at 0°C to 10°C for 1 hour. After that, water and ethyl acetate were added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After filtration through Kiriyama filter paper, the obtained filtrate was concentrated under reduced pressure using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography to obtain 0.96 g of the target product as amorphous material (yield 94.4%). １ Based on the 1H-NMR measurement results, it was confirmed that the obtained compound is compound No. 47 described in International Publication No. 2023 / 190286 (Patent Document 1). 1H-NMR (CDCl3): δ 9.02(1H, d, J=2.1Hz), 8.58(1H, d, J=2.1Hz), 8.34(1H, s), 8.15(1H, d, J=5.1Hz), 7.75-7.71(2H, m), 7.43(2H, d, J=8.1Hz), 7.38(1H, d, J=5.1), 3.52(2H, q, J=7.5Hz), 1.39(3H, t, J=7.5Hz)

[0082] Example 25: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one Under a nitrogen atmosphere, 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picolineimidamide (0.27 g, 0.50 mmol) was dissolved in N,N-dimethylacetamide (4.2 mL) and cooled to 0°C to 10°C in an ice bath. Sodium t-butoxide (96.02 mg, 1.00 mmol) was slowly added thereto, followed by methyl chloroformate (0.26 g, 2.72 mmol) being added dropwise, and the mixture was reacted at 0°C to 10°C for 1 hour. Analysis of the reaction mixture by high-performance liquid chromatography (HPLC) revealed that the HPLC area percentage of the target substance was 92.6%.

[0083] Comparative Examples 1-3: Method for producing 3-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridine-2-yl)-4-(4-(trifluoromethyl)pyridine-2-yl)-1,2,4-oxadiazole-5(4H)-one Under a nitrogen atmosphere, 3-(ethylsulfonyl)-N'-hydroxy-5-(4-(trifluoromethoxy)phenyl)-N-(4-(trifluoromethyl)pyridine-2-yl)picolineimidamide was dissolved in solvent 1 or a mixed solvent of solvent 1 and solvent 2 as described in Table 5, and cooled to 0°C to 10°C in an ice bath. A base as described in Table 5 was added within the range of 0°C to 10°C, and then methyl chloroformate, triphosgene, or carbonyldiimidazole was added as a reactant within the range of 0°C to 10°C. The reaction mixture one hour after the completion of dropwise addition was analyzed by high-performance liquid chromatography (HPLC).

[0084] Table 5 summarizes the solvents, bases, and reaction reagents used, as well as the HPLC area percentages of the raw materials and target products. The HPLC analysis conditions for the examples and comparative examples are as described in Table 4.

Claims

1. A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (1), [In formula (1), R １～６ , １～６ , １～６ , R ３ , R ４ and R ５ are each independently a hydrogen atom, a halogen atom, a C １～６ alkyl group which may have a substituent, a C ２～６ alkenyl group which may have a substituent, a C ２～６ alkynyl group which may have a substituent, a C ３～６ cycloalkyl group which may have a substituent, a C １～６ alkoxy group which may have a substituent, a C ２～６ alkenyloxy group which may have a substituent, a C ２～６ alkynyloxy group which may have a substituent, a C ３～６ cycloalkoxy group which may have a substituent, a C １～６ alkylcarbonyl group which may have a substituent, a C ３～６ cycloalkylcarbonyl group which may have a substituent, a C １～６ alkoxycarbonyl group which may have a substituent, a C ２～６ alkenyloxycarbonyl group which may have a substituent, a C ２～６ alkynyloxycarbonyl group which may have a substituent, a C １～６ alkylcarbonyloxy group which may have a substituent, a C ２～６ alkenylcarbonyloxy group which may have a substituent, a C ２～６ alkynylcarbonyloxy group which may have a substituent, a C １～６ alkylthio group, a phenyl group which may have a substituent, a heterocyclic group which may have a substituent, a phenoxy group which may have a substituent, a pyridyloxy group which may have a substituent, NY​​​​​​ １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ R represents a group selected from the group consisting of cycloalkylcarbonyl groups. ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ An alkylsulfonyl group, a C which may have a substituent １～６ An alkylsulfonyloxy group, a phenyl group which may have a substituent, a heterocyclic group which may have a substituent, a phenoxy group which may have a substituent, a pyridyloxy group which may have a substituent, NY １ Y ２ Group, C(O)NY １ Y ２ Group, C(=NY ２ )Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxy group, trimethylsilyl group, C(O)NH ２ Group and SF ５ Group selected from the group consisting of (Y １ , Y ２ , and Y ３ is as defined above) The following steps: [Step A] An aminopyridine derivative represented by the formula (2) [In the formula (2), R ２ , R ３ , R ４ and R ５ are as defined above] and an (alkylsulfonyl)pyridinecarbonitrile derivative represented by the formula (3) [In the formula (3), R ａ , R ｂ , R ｃ and R ｄ are as defined above] are reacted in the presence of a Lewis acid to obtain an amidine derivative represented by the formula (4) [In the formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ are as defined above] Step A; and [Step B] The amidine derivative represented by the formula (4) and an amine compound represented by the formula (5) [In the formula (5), R ６ is as defined above] are reacted to obtain the (alkylsulfonyl)pyridine derivative represented by the formula (1) [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and also, R ａ , R ｂ , R ｃ and R ｄ A manufacturing method comprising step B, which includes obtaining [which is synonymous with the above]; 2. A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (6), [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step A] Aminopyridine derivative represented by formula (2) [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ [This is synonymous with the above] is reacted in the presence of a Lewis acid to obtain an amidine derivative represented by formula (4). [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ Step A, which includes obtaining [the same as above]; and Step B, which includes obtaining an amidine derivative represented by formula (4) and an amine compound represented by formula (5). [In formula (5), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ By reacting with a group selected from the group consisting of cycloalkylcarbonyl groups, a (alkylsulfonyl)pyridine derivative represented by formula (1) is obtained. [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and R ａ , R ｂ , R ｃ and R ｄ Step B includes obtaining [which is the same as above]; and [Step C] reacting a (alkylsulfonyl)pyridine derivative represented by formula (1) with a carbonylating agent to obtain a (alkylsulfonyl)pyridine derivative represented by formula (6). [In formula (6), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ A manufacturing method comprising step C to obtain [which is synonymous with the above].

3. Step A is (i) an aminopyridine derivative represented by formula (2). [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ The manufacturing method according to claim 1 or 2, comprising the steps of: (ii-a) reacting in solution in the presence of a Lewis acid (which is the same as above); and mixing the reaction solution with an alcohol-containing basic aqueous solution after the reaction is complete.

4. Step A is (i) an aminopyridine derivative represented by formula (2). [In formula (2), R ２ , R ３ , R ４ and R ５ This is synonymous with the above, and the (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ The manufacturing method according to claim 1 or 2, comprising the steps of: (ii-b) reacting in solution in the presence of a Lewis acid (which is equivalent to the above); and mixing the reaction solution with an alcohol-containing acidic aqueous solution after the reaction is complete.

5. A method for producing an amidine derivative represented by formula (4), [In formula (4), R ２ , R ３ , R ４ , and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ , and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (i) an aminopyridine derivative represented by formula (2) and [In formula (2), R ２ , R ３ , R ４ , and R ５ [This is synonymous with the above] (alkylsulfonyl)pyridinecarbonitric derivative represented by formula (3) [In formula (3), R ａ , R ｂ , R ｃ and R ｄ A method for producing [which is synonymous with the above] comprising the step of reacting in solution in the presence of a Lewis acid.

6. The manufacturing method according to claim 5, further comprising the step of mixing the reaction solution with an alcohol-containing basic aqueous solution after the reaction is complete.

7. The manufacturing method according to claim 5, further comprising the step of mixing the reaction solution with an alcohol-containing acidic aqueous solution after the reaction is complete.

8. The manufacturing method according to claim 1 or 2, wherein step B is a reaction carried out using a solvent containing one or more selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol.

9. A method for producing an amidooxime derivative represented by formula (1), [In formula (1), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R6 is a hydrogen atom, and C may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ R represents a group selected from the group consisting of cycloalkylcarbonyl groups. ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base, and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step B] In the presence of a solvent, the amidine derivative represented by formula (4) and [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above. Amine compound represented by formula (5) [In formula (5), R ６ A manufacturing method comprising step A, in which [ is synonymous with the above] reacts.

10. A method for producing an (alkylsulfonyl)pyridine derivative represented by formula (6), [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The following steps: [Step B] In the presence of a solvent, the amidine derivative represented by formula (4) and [In formula (4), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above. Amine compound represented by formula (5) [In formula (5), R ６ This is a hydrogen atom, and C which may have substituents. １～６ C, which may have alkyl groups or substituents ３～６ Cycloalkyl groups, C which may have substituents １～６ C which may have an alkylcarbonyl group and substituents. ３～６ A group selected from the group consisting of cycloalkylcarbonyl groups is reacted to form an amide oxime derivative represented by formula (1). [In formula (1), R ２ , R ３ , R ４ , R ５ and R ６ , and R ａ , R ｂ , R ｃ and R ｄ Step A includes obtaining [which is the same as above]; and [Step C] reacting an amidooxime derivative represented by formula (1) with a carbonylating agent to obtain a (alkylsulfonyl)pyridine derivative represented by formula (6). [In formula (6), R ２ , R ３ , R ４ and R ５ , and R ａ , R ｂ , R ｃ and R ｄ A manufacturing method comprising step B to obtain [which is synonymous with the above].

11. The manufacturing method according to claim 9 or 10, wherein the solvent in [Step A] is a solvent comprising one or more selected from the group consisting of methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, isopentanol, 1-hexanol, and 2-hexanol.

12. In [Step C], the carbonylating agent is a halogenated carbamate compound represented by formula (7): [In the formula R Ｘ C may have substituents. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ The method for producing carbonylating agents according to claim 2 or 10, wherein X represents a group selected from the group consisting of an alkynyloxycarbonyl group, an optionally substituted phenyl group, and an optionally substituted heterocyclic group, and X represents one of fluorine, chlorine, bromine, and iodine, and the carbonylating agent is reacted in the presence of a base selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonides, alkaline earth metal carbonides, alkali metal alkoxides, alkaline earth metal alkoxides, alkali metal metal hydrides, and alkaline earth metal hydrides.

13. The manufacturing method according to claim 12, wherein the reaction in [Step C] is carried out in a solvent containing water.

14. The manufacturing method according to claim 13, wherein the reaction solvent in [Step C] is a mixed solvent containing an amide solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, and an aromatic hydrocarbon or a halogenated aliphatic hydrocarbon.

15. A method for producing the 1,2,4-oxadiazole-5(4H)-one derivative of formula (6), which is: [In formula (6), R ２ , R ３ , R ４ and R ５ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ Represents a group selected from a group consisting of groups, Y １ If multiple C atoms exist, each may independently have a hydrogen atom and a substituent. １～６ Represents a group selected from the group consisting of alkyl groups, Y ２ If multiple C atoms exist, each may independently have a hydrogen atom or a substituent. １～６ C may have alkyl groups or substituents. ２～６ C may have an alkenyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylcarbonyl group or substituent. １～６ The term Y represents a group selected from the group consisting of an alkoxycarbonyl group, a optionally substituted phenyl group, an optionally substituted heterocyclic group, a cyano group, and a hydroxyl group. ３ If multiple C atoms exist, each may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C may have alkyl groups or substituents. １～６ C may have an alkoxy group or substituent. １～６ C may have an alkylthio group or substituent. ３～６ Cycloalkyl groups, optionally substituted phenyl groups, and NY １ Y ２ Represents a group selected from a group of groups (Y １ and Y ２ (This is synonymous with the above), R ａ C may have substituents. １～６ C, which may have alkyl groups and substituents. ３～６ R represents a group selected from the group consisting of cycloalkyl groups. ｂ , R ｃ and R ｄ Each of these may independently have a hydrogen atom, a halogen atom, or a substituent. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C may have an alkoxy group or substituent. ２～６ C may have an alkenyloxy group or substituent. ２～６ C may have an alkynyloxy group or substituents. ３～６ C may have a cycloalkoxy group or substituent. １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ Alkynyloxycarbonyl group, C which may have substituents １～６ C, which may have an alkylcarbonyloxy group or substituents. ２～６ C may have an alkenylcarbonyloxy group or substituent. ２～６ Alkynylcarbonyloxy group, C which may have substituents １～６ C may have alkylthio groups or substituents. １～６ C, which may have an alkylsulfinyl group or substituents. １～６ C, which may have an alkylsulfonyl group or substituents. １～６ Alkyl sulfonyloxy group, optionally substituted phenyl group, optionally substituted heterocyclic group, optionally substituted phenoxy group, optionally substituted pyridyloxy group, NY １ Y ２ Base, C(O)NY １ Y ２ Base, C (=NY ２ ) Y ３ Group, cyano group, nitro group, hydroxy group, mercapto group, amino group, formyl group, carboxyl group, trimethylsilyl group, C(O)NH ２ Base and SF ５ A group selected from the group consisting of (Y １ , Y ２ , and Y ３ (This is synonymous with the above) The hydroxyimidamide derivative represented by formula (1a): [In formula (8), R ２ , R ３ , R ４ , R ５ , R ａ , R ｂ , R ｃ and R ｄ This is synonymous with the above, and the halogenated carbamate compound represented by formula (7): [In the formula R Ｘ C may have substituents. １～６ C, which may have alkyl groups or substituents ２～６ C may have an alkenyl group or substituent. ２～６ C may have an alkynyl group or substituent. ３～６ Cycloalkyl groups, C which may have substituents １～６ C, which may have an alkylcarbonyl group or substituent. ３～６ Cycloalkylcarbonyl group, C which may have substituents １～６ C, which may have an alkoxycarbonyl group or substituent. ２～６ C may have an alkenyloxycarbonyl group or substituent. ２～６ A method for producing a product, comprising reacting a group selected from the group consisting of an alkynyloxycarbonyl group, an optionally substituted phenyl group, and an optionally substituted heterocyclic group, where X represents one of fluorine, chlorine, bromine, and iodine, in the presence of a base selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonides, alkaline earth metal carbonides, alkali metal alkoxides, alkaline earth metal alkoxides, alkali metal metal hydrides, and alkaline earth metal hydrides.

16. The manufacturing method according to claim 15, wherein the reaction is carried out in a solvent containing water.

17. The production method according to claim 15 or 16, wherein a mixed solvent containing an amide solvent selected from the group consisting of N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, and an aromatic hydrocarbon or a halogenated aliphatic hydrocarbon is used as the reaction solvent.

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