JP2006131529A - Pest control composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pest control composition having excellent efficiency for pest control. <P>SOLUTION: This pest control composition is characterized by containing (1) a pyrimidine compound, for example, represented by formula (I-1) or a 1,2,4-thiadiazole compound, for example, represented by formula (II-1) and (2) (E)-4,5-dihydro-6-methyl-4-(3-pyridylmethyleneamino)-1,2,4-triazin-3(2H)-one as active ingredients. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

The present invention relates to a pest control composition.

Conventionally, many compounds have been developed and put into practical use for pest control. However, since these compounds may not necessarily show sufficient efficacy for pest control, development of a pest control composition having an excellent effect for pest control has been desired.

The Pesticide Manual, Thirteenth Edition (edited by Clive Tomlin, published by The British Crop Protection Council and The Royal Society of Chemistry, 2003), 840-841

To provide a pest control composition having an excellent effect on pest control.

The present invention solves the above problems,
(1) General formula

〔式中、Ｒ^１は水素原子またはＣ１−Ｃ４アルキル基を表し、
Ｒ^２はＣ３−Ｃ７アルキニルオキシ基を表し、
Ｒ^３は水素原子、ハロゲン原子またはＣ１−Ｃ３アルキル基を表し、
Ｘ^１は（ハロゲン原子、トリフルオロメチル基及び／又はＣ１−Ｃ４アルキル基で置換されていてもよい）Ｃ４−Ｃ７ポリメチレン基を表す。〕
で示されるピリミジン化合物（以下、化合物（Ｉ）と記すこともある。）若しくは
一般式 化２

[Wherein R ¹ represents a hydrogen atom or a C1-C4 alkyl group,
R ² represents a C3-C7 alkynyloxy group,
R ³ represents a hydrogen atom, a halogen atom or a C1-C3 alkyl group,
X ¹ represents a C4-C7 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group). ]
A pyrimidine compound represented by the formula (hereinafter also referred to as compound (I)) or a general formula 2

〔式中、Ｒ^１はＣ３−Ｃ７アルキニル基を表し、
Ａは下記のＡ^１又はＡ^２を表し、

[Wherein R ¹ represents a C3-C7 alkynyl group,
A represents A ¹ or A ² below,

Ｘ^２はＣ４−Ｃ７アルカンジイル基又はＣ４−Ｃ７アルケンジイル基を表し、
Ｒ^５はハロゲン原子、トリフルオロメチル基又はＣ１−Ｃ４アルキル基を表し、
Ｒ^６はＣ１−Ｃ３アルキル基を表し、
ｌは０〜４までの整数を表し、ｎは０〜２の整数を表す。
ｌが２以上の整数である場合、Ｒ^５は同一又は相異なる基を表し、
ｎが２である場合、Ｒ^６は同一又は相異なる基を表す。〕
で示される１，２，４−チアジアゾール化合物（以下、化合物（II）と記すこともある。）と、
（２）ピメトロジン（以下、化合物（III）と記すこともある。）とを有効成分として含有することを特徴とする有害生物防除組成物（以下、本発明組成物と記すこともある。）及び本発明組成物を有害生物または有害生物の生息場所に施用することを特徴とする有害生物の防除方法
等を提供するものである。

X ² represents a C4-C7 alkanediyl group or a C4-C7 alkenediyl group,
R ⁵ represents a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group,
R ⁶ represents a C1-C3 alkyl group,
l represents an integer of 0 to 4, and n represents an integer of 0 to 2.
when l is an integer of 2 or more, R ⁵ represents the same or different groups;
When n is 2, R ⁶ represents the same or different groups. ]
A 1,2,4-thiadiazole compound (hereinafter also referred to as compound (II)),
(2) A pest control composition (hereinafter also referred to as the present invention composition) characterized by containing pymetrozine (hereinafter sometimes referred to as compound (III)) as an active ingredient; The present invention provides a method for controlling pests, which comprises applying the composition of the present invention to a pest or a habitat of pests.

The composition of the present invention has an excellent effect on pest control.

First, compound (I) will be described.
In general formula 1,
Examples of the C1-C4 alkyl group represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.

The C3-C7 alkynyloxy represented by R ^2, for example 2-position of C3-C7 alkynyloxy group bond is a triple bond between a carbon atom and 3-position carbon atom (hereinafter, (C3-C7) Specific examples include 2-propynyloxy group, 2-butynyloxy group, 1-methyl-2-butynyloxy group, 2-pentynyloxy group, and 4,4-dimethyl. -2-pentynyloxy group, 1-methyl-2-propynyloxy group and 1,1-dimethyl-2-propynyloxy group.

Examples of the halogen atom represented by R ³ include a fluorine atom and a chlorine atom, and examples of the C1-C3 alkyl group include a methyl group and an ethyl group.

In the C4-C7 polymethylene group represented by X ¹ (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group), examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atom. Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, and examples of the C4-C7 polymethylene group include a tetramethylene group. , A pentamethylene group, a hexamethylene group, and a heptamethylene group.

Examples of the C4-C7 polymethylene group represented by X ¹ (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group) include a tetramethylene group, a 1-methyltetramethylene group, 2 -Methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 2-ethyltetramethylene group, 1,4-dimethyl Tetramethylene group, 2,3-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2-fluorotetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group , Pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethyl Len group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 1-isopropylpentamethylene group Group, 2-isopropylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene group, 2- (tert-butyl) pentamethylene group, 3- (tert-butyl) pentamethylene group, 1 -(Sec-butyl) pentamethylene group, 2- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2, 4-dimethylpentamethylene group, 1,1-dimethylpentamethylene group, 2,2 Dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-ethyl-4-methylpentamethylene group, 2,4-diethylpentamethylene group, 1,2-dimethyl Pentamethylene group, 2,2,4-trimethylpentamethylene group, 1,2,4,5-tetramethylpentamethylene group, 2,2,4,4-tetramethylpentamethylene group, 2-fluoropentamethylene group, 2-chloropentamethylene group, 2-bromopentamethylene group, 3-fluoropentamethylene group, 3-chloropentamethylene group, 3-bromopentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropenta Methylene group, 2-fluoro-2-methylpentamethylene group, 1- (trifluoromethyl) pentamethyle Group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4 -Methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 2-propylhexamethylene group, 3-propylhexamethylene group, 1- Isopropylhexamethylene group, 2-isopropylhexamethylene group, 3-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1- (trifluoromethyl) hexamethylene group, 1, 4-dimethylhexamethylene group, 1,5-dimethyl Examples include a hexamethylene group, a 1,6-dimethylhexamethylene group, a 2,5-dimethylhexamethylene group, and a heptamethylene group.

Compound (I) in which X ¹ is a tetramethylene group has the following formula:

〔式中、Ｒ^１、Ｒ^２及びＲ^３は前記と同じ意味を表す。〕で示される。

[Wherein R ¹ , R ² and R ³ represent the same meaning as described above. ] Is shown.

Compound (I) in which X ¹ is a pentamethylene group has the following formula:

〔式中、Ｒ^１、Ｒ^２及びＲ^３は前記と同じ意味を表す。〕で示される。

[Wherein R ¹ , R ² and R ³ represent the same meaning as described above. ] Is shown.

Compound (I) wherein X ¹ is a hexamethylene group has the following formula:

〔式中、Ｒ^１、Ｒ^２及びＲ^３は前記と同じ意味を表す。〕で示される。

[Wherein R ¹ , R ² and R ³ represent the same meaning as described above. ] Is shown.

Compound (I) wherein X ¹ is a heptamethylene group has the following formula

〔式中、Ｒ^１、Ｒ^２及びＲ^３は前記と同じ意味を表す。〕で示される。

[Wherein R ¹ , R ² and R ³ represent the same meaning as described above. ] Is shown.

Examples of the compound (I) include the following pyrimidine compounds.
A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom;
A pyrimidine compound represented by the general formula 1, wherein R ² is a (C3-C7) 2-alkynyloxy group;
In the general formula 1, a pyrimidine compound in which R ² is a 2-butynyloxy group or a 2-pentynyloxy group;
A pyrimidine compound represented by the general formula 1, wherein R ³ is a hydrogen atom;
A pyrimidine compound represented by the general formula 1, wherein R ³ is a halogen atom;
A pyrimidine compound represented by the general formula 1, wherein R ³ is a fluorine atom;

A pyrimidine compound represented by the general formula 1, wherein X ¹ is a tetramethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group);
A pyrimidine compound represented by the general formula 1, wherein X ¹ is a pentamethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group);
A pyrimidine compound represented by the general formula 1, wherein X ¹ is a hexamethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group);

A pyrimidine compound represented by the general formula: wherein X ¹ is a C4-C7 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group);
A pyrimidine compound represented by the general formula 1, wherein X ¹ is a tetramethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group);
A pyrimidine compound represented by the general formula 1, wherein X ¹ is a pentamethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group);
In the general formula 1, a pyrimidine compound in which X ¹ is a hexamethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group);

In the general formula 1, a pyrimidine compound in which X ¹ is a tetramethylene group which may be substituted with a C1-C4 alkyl group;
In the general formula 1, a pyrimidine compound in which X ¹ is a pentamethylene group optionally substituted with a C1-C4 alkyl group;
A pyrimidine compound represented by the general formula 1, wherein X ¹ is a hexamethylene group optionally substituted by a C1-C4 alkyl group;

A pyrimidine compound represented by the general formula: wherein R ¹ is a hydrogen atom and R ³ is a hydrogen atom;
A pyrimidine compound represented by the general formula: wherein R ¹ is a hydrogen atom and R ³ is a halogen atom;
A pyrimidine compound in which R ¹ is a hydrogen atom and R ³ is a fluorine atom;

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, and R ³ is a hydrogen atom;
A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, and R ³ is a halogen atom;
A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, and R ³ is a fluorine atom;

In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a hydrogen atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a hexamethylene group optionally substituted with (/ C1-C4 alkyl group);
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a halogen atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a hexamethylene group optionally substituted with (/ C1-C4 alkyl group);
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C 3 -C 7) 2 -alkynyloxy group, R ³ is a fluorine atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a hexamethylene group optionally substituted with (/ C1-C4 alkyl group);

In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a hydrogen atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a pentamethylene group optionally substituted with a C / C4 alkyl group);
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a halogen atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a pentamethylene group optionally substituted with a C / C4 alkyl group);
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C 3 -C 7) 2 -alkynyloxy group, R ³ is a fluorine atom, and X ¹ is a (halogen atom, trifluoromethyl group and A pyrimidine compound which is a pentamethylene group optionally substituted with a C / C4 alkyl group);

In General Formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a hydrogen atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a hexamethylene group optionally substituted with a C1-C4 alkyl group;
In General Formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a halogen atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a hexamethylene group optionally substituted by a C1-C4 alkyl group;
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a fluorine atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a hexamethylene group optionally substituted with a C1-C4 alkyl group;

In General Formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a hydrogen atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a pentamethylene group optionally substituted with a C1-C4 alkyl group;
In General Formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a halogen atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a pentamethylene group optionally substituted with a C1-C4 alkyl group;
In the general formula 1, R ¹ is a hydrogen atom, R ² is a (C3-C7) 2-alkynyloxy group, R ³ is a fluorine atom, and X ¹ is a (halogen atom, trifluoromethyl group or A pyrimidine compound which is a pentamethylene group optionally substituted with a C1-C4 alkyl group;

Next, the manufacturing method of compound (I) is demonstrated.
Compound (I) can be produced, for example, by Production Process Example 1 or Production Process Example 2 described below.

Manufacturing process example 1
Compound (I) can be produced by reacting a compound represented by formula (IV) with a compound represented by formula (V) in the presence of a base.

〔式中、Ｒ^１、Ｒ^２、Ｒ^３及びＸ^１は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物があげられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、カリウムｔｅｒｔ−ブトキシド、ナトリウムｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド類があげられる。
反応に用いられる試剤の量は、式（IV）で示される化合物１モルに対して、式（Ｖ）で示される化合物が通常１〜２モルの割合であり、塩基が通常１〜２モルの割合である。
該反応の反応温度は通常０〜８０℃の範囲であり、反応時間は通常０．５〜１２時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、乾燥、濃縮する等の後処理操作を行うにより、化合物（Ｉ）を単離することができる。単離された化合物（Ｉ）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein R ¹ , R ² , R ³ and X ¹ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, ethers such as 1,4-dioxane, acid amides such as N, N-dimethylformamide, and nitriles such as acetonitrile. , Sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and alkali metal alkoxides such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the reagent used in the reaction is usually 1 to 2 mol of the compound represented by the formula (V) and 1 to 2 mol of the base based on 1 mol of the compound represented by the formula (IV). It is a ratio.
The reaction temperature of the reaction is usually in the range of 0 to 80 ° C., and the reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, the compound (I) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound (I) can be further purified by chromatography, recrystallization and the like.

Manufacturing process example 2
Compound (I) can also be produced by reacting a compound represented by formula (VI) with a compound represented by formula (VII) (or a salt such as a hydrochloride thereof).

〔式中、Ｒ^１、Ｒ^２、Ｒ^３及びＸ^１は前記と同じ意味を表す。〕
該反応は、溶媒の存在下または非存在下、塩基の存在下または非存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、アセトニトリル等のニトリル類、メタノール、エタノール等のアルコール類及びこれらの混合物があげられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、トリエチルアミン、エチルジイソプロピルアミン等の第３級アミン類があげられる。
反応に用いられる式（VII）で示される化合物の量は、式（VI）で示される化合物１モルに対して、通常１〜３モルの割合である。
塩基の存在下で反応が行われる場合、反応に用いられる塩基の量は、式（VI）で示される化合物１モルに対して、通常１〜４モルの割合である。
該反応の反応温度は、通常０〜１５０℃の範囲であり、反応時間は通常０．１〜４８時間である。
反応終了後は、例えば以下の方法により化合物（Ｉ）を単離することができる。
（i） 反応混合物を有機溶媒抽出し、乾燥、濃縮する方法。
（ii） 反応混合物をそのまま濃縮する方法。
（iii） 反応混合物そのものを化合物（Ｉ）として単離する方法。
単離された化合物（Ｉ）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein R ¹ , R ² , R ³ and X ¹ represent the same meaning as described above. ]
The reaction is performed in the presence or absence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, ethers such as 1,4-dioxane, acid amides such as N, N-dimethylformamide, and nitriles such as acetonitrile. Alcohols such as methanol and ethanol, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and tertiary amines such as triethylamine and ethyldiisopropylamine.
The amount of the compound represented by the formula (VII) used in the reaction is usually 1 to 3 mol relative to 1 mol of the compound represented by the formula (VI).
When the reaction is performed in the presence of a base, the amount of the base used in the reaction is usually 1 to 4 moles relative to 1 mole of the compound represented by the formula (VI).
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C., and the reaction time is usually 0.1 to 48 hours.
After completion of the reaction, for example, compound (I) can be isolated by the following method.
(I) A method in which the reaction mixture is extracted with an organic solvent, dried and concentrated.
(Ii) A method of concentrating the reaction mixture as it is.
(Iii) A method of isolating the reaction mixture itself as compound (I).
The isolated compound (I) can be further purified by chromatography, recrystallization and the like.

  Next, the manufacturing method of the manufacturing intermediate of compound (I) is demonstrated.

Reference manufacturing process example 1
The compound represented by the formula (IV) can be produced by reacting the compound represented by the formula (VIII) with the compound represented by the formula (VII) (or a salt such as a hydrochloride thereof).

〔式中、Ｒ^１、Ｒ^３及びＸ^１は前記と同じ意味を表す。〕
該反応は、溶媒の存在下または非存在下、塩基の存在下または非存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、アセトニトリル等のニトリル類、メタノール、エタノール等のアルコール類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物があげられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、カリウムｔｅｒｔ−ブトキシド、ナトリウムｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド類があげられる。
反応に用いられる式（VII）で示される化合物の量は、式（VIII）で示される化合物１モルに対して、通常１〜３モルの割合である。
塩基の存在下で反応が行われる場合、反応に用いられる塩基の量は、式（VII）で示される化合物１モルに対して、通常１〜４モルの割合である。
該反応の反応温度は通常０〜１５０℃の範囲であり、反応時間は通常０．１〜４８時間の範囲である。
反応終了後は、例えば以下の方法により式（IV）で示される化合物を単離することができる。
（i） 反応混合物を有機溶媒抽出し、乾燥、濃縮する方法。
（ii） 反応混合物をそのまま濃縮する方法。
（iii） 反応混合物そのものを式（IV）で示される化合物として単離する方法。
単離された式（IV）で示される化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein R ¹ , R ³ and X ¹ represent the same meaning as described above. ]
The reaction is performed in the presence or absence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, ethers such as 1,4-dioxane, nitriles such as acetonitrile, alcohols such as methanol and ethanol, N, Examples thereof include acid amides such as N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and alkali metal alkoxides such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the compound represented by the formula (VII) used in the reaction is usually 1 to 3 mol relative to 1 mol of the compound represented by the formula (VIII).
When the reaction is performed in the presence of a base, the amount of the base used in the reaction is usually 1 to 4 moles relative to 1 mole of the compound represented by the formula (VII).
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C., and the reaction time is usually in the range of 0.1 to 48 hours.
After completion of the reaction, for example, the compound represented by the formula (IV) can be isolated by the following method.
(I) A method in which the reaction mixture is extracted with an organic solvent, dried and concentrated.
(Ii) A method of concentrating the reaction mixture as it is.
(Iii) A method of isolating the reaction mixture itself as a compound represented by the formula (IV).
The isolated compound represented by the formula (IV) can be further purified by chromatography, recrystallization and the like.

Reference manufacturing process example 2
The compound represented by the formula (VI) can be produced by reacting the compound represented by the formula (VIII) with the compound represented by the formula (V) in the presence of a base.

〔式中、Ｒ^１、Ｒ^２及びＲ^３は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、ｔｅｒｔ−ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物があげられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、カリウムｔｅｒｔ−ブトキシド、ナトリウムｔｅｒｔ−ブトキシド等のアルカリ金属アルコキシド類があげられる。
反応に用いられる試剤の量は、式（VIII）で示される化合物１モルに対して、式（Ｖ）で示される化合物が通常１〜２モルの割合であり、塩基が通常１〜２モルの割合である。
該反応の反応温度は通常０〜８０℃の範囲であり、反応時間は通常０．５〜１２時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、乾燥、濃縮する等の操作を行うことにより、式（VI）で示される化合物を単離することができる。単離された式（VI）で示される化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein R ¹ , R ² and R ³ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane, acid amides such as N, N-dimethylformamide, and nitriles such as acetonitrile. , Sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and alkali metal alkoxides such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the reagent used in the reaction is usually 1 to 2 mol of the compound represented by the formula (V) and 1 to 2 mol of the base based on 1 mol of the compound represented by the formula (VIII). It is a ratio.
The reaction temperature of the reaction is usually in the range of 0 to 80 ° C., and the reaction time is usually in the range of 0.5 to 12 hours.
After completion of the reaction, the compound represented by the formula (VI) can be isolated by performing operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound represented by the formula (VI) can be further purified by chromatography, recrystallization and the like.

Reference manufacturing process example 3
The compound represented by the formula (VII) can be produced, for example, from the compound represented by the formula (IX) according to the following scheme.

〔式中、Ｘ’は（ハロゲン原子、トリフルオロメチル基若しくはＣ１−Ｃ４アルキル基で置換されていてもよい）Ｃ３−Ｃ６ポリメチレン基を表し、Ｘ^１は前記と同じ意味を表す。〕

[Wherein, X ′ represents a C3-C6 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group), and X ¹ represents the same meaning as described above. ]

Step (3-1)
The compound represented by the formula (X) can be produced by reacting the compound represented by the formula (IX) with hydroxylamine (or a salt such as a hydrochloride thereof) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran and diethyl ether, acid amides such as dimethylformamide, alcohols such as methanol and ethanol, water, and a mixture thereof.
Examples of the base used in the reaction include inorganic bases such as sodium hydroxide and potassium hydroxide, tertiary amines such as triethylamine, and nitrogen-containing aromatics such as pyridine.
The amount of the reagent used in the reaction is usually 1 to 3 moles of hydroxylamine (or a salt thereof) and 1 to 5 moles of base to 1 mole of the compound represented by formula (IX). It is.
The reaction temperature is usually in the range of 0 to 80 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound represented by the formula (X) can be isolated by performing operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound represented by the formula (X) can be further purified by chromatography or the like.

The compound represented by the formula (XI) is exemplified by Synthesis, (1980), p. 222-223 or J.H. Am. Chem. Soc. , (1983), 105, p. The compound described in 2381-2843 or can be prepared, for example, by the method described below.
Step (3-2)
The compound represented by the formula (XI) can be produced by reacting the compound represented by the formula (X) in the presence of a rearrangement reaction agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include acid amides such as dimethylformamide, aromatic hydrocarbons such as toluene and benzene, and mixtures thereof.
Examples of the rearrangement reagent used in the reaction include phosphorus chlorides such as phosphorus oxychloride, sulfur chlorides such as thionyl chloride, and acids such as polyphosphoric acid and sulfuric acid.
The amount of the rearrangement reaction agent used in the reaction is usually in a ratio of 0.1 mol to excess with respect to 1 mol of the compound represented by the formula (X).
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound represented by the formula (XI) can be isolated by performing operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound represented by the formula (XI) can be further purified by chromatography or the like.

The compound represented by the formula (VII) is, for example, J. Am. Chem. Soc. , (1983), 105, p. 238-12843 or J.H. Heterocyclic. Chem. , (1980) 17, p. Or a compound described in the following, for example.
Step (3-3)
The compound represented by the formula (VII) can be produced by reducing the compound represented by the formula (XI).
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran and diethyl ether.
Examples of the reducing agent used in the reaction include aluminum hydrides such as lithium aluminum hydride.
The amount of the reducing agent used in the reaction is usually 0.5 to 6 mol with respect to 1 mol of the compound represented by the formula (XI).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, for example, the compound represented by the formula (VII) can be isolated by the following method.
(I) A method in which water, a 15% aqueous sodium hydroxide solution, and water are sequentially added to the reaction mixture, stirred, dried and then concentrated and distilled if necessary.
(Ii) Water, 15% aqueous sodium hydroxide and water are sequentially added to the reaction mixture and stirred, dried, stirred in the presence or absence of a solvent and in the presence of hydrogen chloride (or a solution thereof), A method of concentrating to a hydrochloride of the compound represented by formula (VII).

Reference manufacturing process example 4
The compound represented by the formula (VII) can be produced from the compound represented by the formula (XII) according to the following scheme.

〔式中、X"は（ハロゲン原子、トリフルオロメチル基若しくはＣ１−Ｃ４アルキル基で置換されていてもよい）Ｃ２−Ｃ５ポリメチレン基を表し、Ｘ^１は前記と同じ意味を表す。〕

[Wherein, X ″ represents a C2-C5 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group), and X ¹ represents the same meaning as described above.]

Step (4-1)
The compound represented by the formula (XIII) can be produced by reacting the compound represented by the formula (XII) with urea.
The reaction is usually performed in the absence of a solvent.
The amount of urea used in the reaction is usually in a ratio of 10 mol to excess with respect to 1 mol of the compound represented by the formula (XII).
The reaction temperature of the reaction is usually in the range of 50 to 170 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound represented by the formula (XIII) can be isolated by performing operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound represented by the formula (XIII) can be further purified by chromatography or the like.

Step (4-2)
The compound represented by the formula (VII) can be produced by reducing the compound represented by the formula (XIII).
The reaction can be usually produced in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran and diethyl ether.
Examples of the reducing agent used in the reaction include aluminum hydrides such as lithium aluminum hydride.
The amount of the reducing agent used in the reaction is usually 1 to 6 moles per mole of the compound represented by the formula (XIII).
The reaction temperature of the reaction is usually in the range of 0 to 120 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, for example, the compound represented by the formula (VII) can be isolated by the following method.
(I) A method in which water, a 15% aqueous sodium hydroxide solution, and water are sequentially added to the reaction mixture, stirred, dried and then concentrated and distilled if necessary.
(Ii) Water, 15% aqueous sodium hydroxide and water are sequentially added to the reaction mixture and stirred, dried, stirred in the presence or absence of a solvent and in the presence of hydrogen chloride (or a solution thereof), A method of concentrating to a hydrochloride of the compound represented by formula (VII).

Next, specific examples of compound (I) are shown below.
A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-propynyloxy group, R ³ is a hydrogen atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-butynyloxy group, R ³ is a methyl group, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, penta Methylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1,5-dimethylpentamethylene group, 1,3 -Dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 1- (trifluoromethyl ) Pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoro) (Romethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group Groups, 3-ethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-propynyloxy group, R ³ is a fluorine atom, and X ¹ is any of the following:
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-propynyloxy group, R ³ is a chlorine atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, penta Methylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1,5-dimethylpentamethylene group, 1,3 -Dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 1- (trifluoromethyl ) Pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoro) (Romethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group Groups, 3-ethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 1-methyl-2-propynyloxy group, R ³ is a chlorine atom, and X ¹ is any of the following: ;
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, penta Methylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1,5-dimethylpentamethylene group, 1,3 -Dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 1- (trifluoromethyl ) Pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoro) (Romethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group Groups, 3-ethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-pentynyloxy group, R ³ is a hydrogen atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 2-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2-fluorotetramethylene group, 2- (trifluoromethyl) tetramethylene Group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group Group, 1-propylpentamethylene group, 2-propylpentamethyl Group, 3-propylpentamethylene group, 1-isopropylpentamethylene group, 2-isopropylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene group, 2- (tert-butyl) penta Methylene group, 3- (tert-butyl) pentamethylene group, 1- (sec-butyl) pentamethylene group, 2- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethyl Pentamethylene group, 1,4-dimethylpentamethylene group, 2,4-dimethylpentamethylene group, 1,1-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2 -Ethyl-4-methylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2 4-diethylpentamethylene group, 2-fluoropentamethylene group, 2-chloropentamethylene group, 2-bromopentamethylene group, 3-fluoropentamethylene group, 3-chloropentamethylene group, 3-bromopentamethylene group, 2 , 2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 2-fluoro-2-methylpentamethylene group, 1- (trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1- Propylhexamethylene group, 2-propylhexamethylene group, 3-propylhexamethylene group, 1-isopropylhexamethylene group, 2-isopropylhexamethylene group, 3-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group 1-isobutylhexamethylene group, 1,4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl ) Hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-pentynyloxy group, R ³ is a methyl group, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, penta Methylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1,5-dimethylpentamethylene group, 1,3 -Dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 1- (trifluoromethyl ) Pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoro) (Romethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group Group, 3-ethylhexamethylene group, 1,4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoro Methyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-pentynyloxy group, R ³ is a fluorine atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 2-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2-fluorotetramethylene group, 2- (trifluoromethyl) tetramethylene Group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group Group, 1-propylpentamethylene group, 2-propylpentamethyl Group, 3-propylpentamethylene group, 1-isopropylpentamethylene group, 2-isopropylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene group, 2- (tert-butyl) penta Methylene group, 3- (tert-butyl) pentamethylene group, 1- (sec-butyl) pentamethylene group, 2- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethyl Pentamethylene group, 1,4-dimethylpentamethylene group, 2,4-dimethylpentamethylene group, 1,1-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2 -Ethyl-4-methylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2 4-diethylpentamethylene group, 2-fluoropentamethylene group, 2-chloropentamethylene group, 2-bromopentamethylene group, 3-fluoropentamethylene group, 3-chloropentamethylene group, 3-bromopentamethylene group, 2 , 2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 2-fluoro-2-methylpentamethylene group, 1- (trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1- Propylhexamethylene group, 2-propylhexamethylene group, 3-propylhexamethylene group, 1-isopropylhexamethylene group, 2-isopropylhexamethylene group, 3-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group 1-isobutylhexamethylene group, 1,4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl ) Hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-pentynyloxy group, R ³ is a chlorine atom, and X ¹ is any of the following:
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 2,4 -Dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3 , 3-Difluoropentamethylene group, 1- (trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene Group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexene Methylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1 -Isobutylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-butynyloxy group, R ³ is a hydrogen atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 2-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2-fluorotetramethylene group, 2- (trifluoromethyl) tetramethylene Group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group Group, 1-propylpentamethylene group, 2-propylpentamethyl Group, 3-propylpentamethylene group, 1-isopropylpentamethylene group, 2-isopropylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene group, 2- (tert-butyl) penta Methylene group, 3- (tert-butyl) pentamethylene group, 1- (sec-butyl) pentamethylene group, 2- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethyl Pentamethylene group, 1,4-dimethylpentamethylene group, 2,4-dimethylpentamethylene group, 1,1-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2 -Ethyl-4-methylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2 4-diethylpentamethylene group, 2-fluoropentamethylene group, 2-chloropentamethylene group, 2-bromopentamethylene group, 3-fluoropentamethylene group, 3-chloropentamethylene group, 3-bromopentamethylene group, 2 , 2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 2-fluoro-2-methylpentamethylene group, 1- (trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1- Propylhexamethylene group, 2-propylhexamethylene group, 3-propylhexamethylene group, 1-isopropylhexamethylene group, 2-isopropylhexamethylene group, 3-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group 1-isobutylhexamethylene group, 1,4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl ) Hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-butynyloxy group, R ³ is a fluorine atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltetramethylene group, 1-propyltetramethylene group, 1-isopropyltetramethylene group, 1- (tert-butyl) tetramethylene group, 2-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2,3-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 2-fluorotetramethylene group, 2- (trifluoromethyl) tetramethylene Group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group Group, 1-propylpentamethylene group, 2-propylpentamethyl Group, 3-propylpentamethylene group, 1-isopropylpentamethylene group, 2-isopropylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene group, 2- (tert-butyl) penta Methylene group, 3- (tert-butyl) pentamethylene group, 1- (sec-butyl) pentamethylene group, 2- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethyl Pentamethylene group, 1,4-dimethylpentamethylene group, 2,4-dimethylpentamethylene group, 1,1-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2 -Ethyl-4-methylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2 4-diethylpentamethylene group, 2-fluoropentamethylene group, 2-chloropentamethylene group, 2-bromopentamethylene group, 3-fluoropentamethylene group, 3-chloropentamethylene group, 3-bromopentamethylene group, 2 , 2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 2-fluoro-2-methylpentamethylene group, 1- (trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1- Propylhexamethylene group, 2-propylhexamethylene group, 3-propylhexamethylene group, 1-isopropylhexamethylene group, 2-isopropylhexamethylene group, 3-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group 1-isobutylhexamethylene group, 1,4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl ) Hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 2-butynyloxy group, R ³ is a chlorine atom, and X ¹ is any of the following:
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound in which R ¹ is a hydrogen atom, R ² is a 1-methyl-2-propynyloxy group, R ³ is a hydrogen atom, and X ¹ is any of the following: ;
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound in which R ¹ is a hydrogen atom, R ² is a 1-methyl-2-propynyloxy group, R ³ is a fluorine atom, and X ¹ is any of the following: ;
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 1-methyl-2-butynyloxy group, R ³ is a hydrogen atom, and X ¹ is any of the following:
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound in which R ¹ is a hydrogen atom, R ² is a 1-methyl-2-butynyloxy group, R ³ is a fluorine atom, and X ¹ is any of the following:
Tetramethylene, 1-methyltetramethylene, 1-ethyltetramethylene, 1-propyltetramethylene, 1-isopropyltetramethylene, 1- (tert-butyl) tetramethylene, 1,4-dimethyltetramethylene Group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, pentamethylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1 -Ethylpentamethylene group, 2-ethylpentamethylene group, 1-propylpentamethylene group, 2-propylpentamethylene group, 3-propylpentamethylene group, 3-isopropylpentamethylene group, 1- (tert-butyl) pentamethylene Group, 3- (tert-butyl) pentamethylene group 1- (sec-butyl) pentamethylene group, 1,5-dimethylpentamethylene group, 1,3-dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3 -Dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 2-fluoropentamethylene group, 3-fluoropentamethylene group, 2,2-difluoropentamethylene group, 3,3-difluoropentamethylene group, 1 -(Trifluoromethyl) pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoromethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethyl Group, 2-ethylhexamethylene group, 3-ethylhexamethylene group, 1-propylhexamethylene group, 1-isopropylhexamethylene group, 1- (tert-butyl) hexamethylene group, 1-isobutylhexamethylene group, 1 , 4-dimethylhexamethylene group, 1,5-dimethylhexamethylene group, 1,6-dimethylhexamethylene group, 2,5-dimethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

A pyrimidine compound represented by the general formula 1, wherein R ¹ is a hydrogen atom, R ² is a 1-methyl-2-butynyloxy group, R ³ is a chlorine atom, and X ¹ is any of the following:
Tetramethylene group, 1-methyltetramethylene group, 1-ethyltetramethylene group, 1,4-dimethyltetramethylene group, 2- (trifluoromethyl) tetramethylene group, 3- (trifluoromethyl) tetramethylene group, penta Methylene group, 1-methylpentamethylene group, 2-methylpentamethylene group, 3-methylpentamethylene group, 1-ethylpentamethylene group, 2-ethylpentamethylene group, 1,5-dimethylpentamethylene group, 1,3 -Dimethylpentamethylene group, 1,4-dimethylpentamethylene group, 2,2-dimethylpentamethylene group, 3,3-dimethylpentamethylene group, 2-ethyl-5-methylpentamethylene group, 1- (trifluoromethyl ) Pentamethylene group, 2- (trifluoromethyl) pentamethylene group, 3- (trifluoro) (Romethyl) pentamethylene group, hexamethylene group, 1-methylhexamethylene group, 2-methylhexamethylene group, 3-methylhexamethylene group, 4-methylhexamethylene group, 1-ethylhexamethylene group, 2-ethylhexamethylene group Groups, 3-ethylhexamethylene group, 1- (trifluoromethyl) hexamethylene group and heptamethylene group.

Hereinafter, although the manufacture example of compound (I) used in this invention composition is demonstrated in more detail, this invention is not limited only to these examples.
Specific production examples of the compound (I) used in the composition of the present invention produced according to the description of the production steps (Chemical Formula 8), (Chemical Formula 9) and reaction conditions in each step are shown. . In the production examples and reference production examples, ¹ H-NMR indicates data obtained by measuring tetramethylsilane as an internal standard in a deuterated chloroform solvent, except for special cases.

Production Example 1 [Production Example of Compound (I-1)]
To 4 ml of N, N-dimethylformamide was added 0.36 g of 4- (2-butynyloxy) -6-chloro-5-fluoropyrimidine, 0.62 g of potassium carbonate and 0.25 g of 3,3-dimethylpyrrolidine hydrochloride. Stir at 6 ° C. for 6 hours. Thereafter, a saturated aqueous ammonium chloride solution was poured into the reaction mixture which was allowed to cool to near room temperature, and extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 4- (2-butynyloxy) -5-fluoro-6- (3,3-dimethylpyrrolidin-1-yl) pyrimidine (hereinafter referred to as compound (I-1)). 0.15 g was obtained.
Compound (I-1)

¹Ｈ−ＮＭＲ：１．１３（ｓ，６Ｈ），１．７３（ｔ，２Ｈ），１．８７（ｔ，３Ｈ），３．４２(ｄ，２Ｈ)，３．７６（ｔｄ，２Ｈ），４．９７(ｑ，２H，)， ８．０２(ｓ，１Ｈ)

¹ H-NMR: 1.13 (s, 6H), 1.73 (t, 2H), 1.87 (t, 3H), 3.42 (d, 2H), 3.76 (td, 2H), 4.97 (q, 2H,), 8.02 (s, 1H)

Production Example 2 [Production Example of Compound (I-2)]
4-Chloro-5-fluoro-6- (2-pentynyloxy) pyrimidine (0.2 g) and hexamethyleneimine (0.28 g) were mixed and allowed to stand at room temperature for 3 hours. Thereafter, the reaction mixture was subjected to silica gel column chromatography, and hexahydro-1- {5-fluoro-6- (2-pentynyloxy) -4-pyrimidinyl} azepine (hereinafter referred to as compound (I-2)). 0.26 g was obtained.
Compound (I-2)

^１Ｈ−ＮＭＲ：１．１５（ｔ，３Ｈ），１．５２〜１．６１（ｍ，４Ｈ），１．７２〜１．７９（ｍ，４Ｈ），２．２４（ｑｔ，２Ｈ），３．６５〜３．７４（ｍ，４Ｈ），４．９９（ｔ，２Ｈ），８．０１（ｓ，１Ｈ）

¹ H-NMR: 1.15 (t, 3H), 1.52 to 1.61 (m, 4H), 1.72 to 1.79 (m, 4H), 2.24 (qt, 2H), 3 .65 to 3.74 (m, 4H), 4.99 (t, 2H), 8.01 (s, 1H)

Production Example 3 [Production Example of Compound (I-3)]
4-Chloro-6- (2-butynyloxy) pyrimidine (0.3 g) and 3-trifluoromethylpiperidine (0.25 g) were mixed and allowed to stand at room temperature for 10 hours. The reaction mixture allowed to cool to about room temperature was subjected to silica gel column chromatography, and described as 4- (2-butynyloxy) -6- (3-trifluoromethylpiperidino) pyrimidine (hereinafter referred to as compound (I-3)). ) 0.30 g was obtained.
Compound (I-3)

^１Ｈ−ＮＭＲ：１．３６〜１．６０（ｍ，２Ｈ），１．７２〜１．８３（ｍ，４Ｈ，involving a triplet at 1.87），１．９５〜２．１４（ｍ，１Ｈ），２．１９〜２．２４（ｍ，１Ｈ），２．７５〜２．８４（ｍ，２Ｈ），４．１３（ｂｒｄ，１Ｈ），４．５３（ｂｒｄ，１Ｈ），４．８４（ｑ，２Ｈ），５．８２（ｓ，１Ｈ），８．２４（ｓ，１Ｈ）

¹ H-NMR: 1.36 to 1.60 (m, 2H), 1.72 to 1.83 (m, 4H, involving a triplet at 1.87), 1.95 to 2.14 (m, 1H), 2.19-2.24 (m, 1H), 2.75-2.84 (m, 2H), 4.13 (brd, 1H), 4.53 (brd, 1H), 4.84 (q, 2H), 5.82 (s, 1H), 8.24 (s, 1H)

Production Example 4 [Production Example of Compound (I-4)]
To a solution of 0.3 g of 4- (2-butynyloxy) -6-chloro-5-fluoropyrimidine in 3 ml of ethanol, 0.51 g of 3,5-dimethylpiperidine (cis: trans = about 8: 2) was added. And stirred for 8 hours under reflux. Then, after concentrating the reaction mixture allowed to cool to near room temperature, a saturated aqueous ammonium chloride solution was poured, and the mixture was extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography, and described as 4- (2-butynyloxy) -5-fluoro-6- (3,5-dimethylpiperidino) pyrimidine (hereinafter referred to as compound (I-4)). ) 0.40 g was obtained.
In the compound of the present invention, there exist cis-trans isomers related to two methyl groups on the piperidine ring. In the production example, a product of cis: trans = about 8: 2 was obtained.
Compound (I-4)

^１Ｈ−ＮＭＲ：０．８０（ｄｄ，１Ｈ），０．９１（ｄ，６Ｈ），１．６０〜１．７２（ｍ，２Ｈ），１．８１〜１．８９（ｍ，４Ｈ，involving a triplet at １．８７），２．３５〜２．４３（ｍ，２Ｈ），４．３５〜４．４１（ｍ，２Ｈ），４．９７（ｑ，２Ｈ），８．０３（ｓ，１Ｈ）；
０．９４（ｓ），１．４６〜１．４９（ｍ），３．３１（ｄｄ），３．７５（ｄｄ），８．０１（ｓ）

¹ H-NMR: 0.80 (dd, 1H), 0.91 (d, 6H), 1.60 to 1.72 (m, 2H), 1.81 to 1.89 (m, 4H, involving a triplet at 1.87), 2.35 to 2.43 (m, 2H), 4.35 to 4.41 (m, 2H), 4.97 (q, 2H), 8.03 (s, 1H) ;
0.94 (s), 1.46 to 1.49 (m), 3.31 (dd), 3.75 (dd), 8.01 (s)

Production Example 5 [Production Example of Compound (I-5)]
To a suspension of 0.07 g of sodium hydride (60% oily) in 3 ml of tetrahydrofuran, a solution of 0.11 g of 2-butyn-1-ol dissolved in 0.5 ml of tetrahydrofuran was added dropwise at room temperature and stirred for 10 minutes. To this mixed solution was added dropwise a solution prepared by dissolving 0.30 g of 1- (6-chloropyrimidin-4-yl) -cis-2,6-dimethylhexahydroazepine in 0.5 ml of tetrahydrofuran at room temperature, and at 60 ° C. for 8 hours. Stir. Thereafter, the reaction mixture was allowed to cool to near room temperature, poured into a saturated aqueous ammonium chloride solution, and extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give 1- (6- (2-butynyloxy) -pyrimidin-4-yl) -cis-2,6-dimethylhexahydroazepine (hereinafter, compound (I-5)). 0.25 g was obtained.
Compound (I-5)

ＧＣ−ＭＳ：２７３（Ｍ＋）

GC-MS: 273 (M +)

Next, reference production examples are shown for production of production intermediates of compounds (I-1) to (I-5).

Reference production example 1
A solution obtained by suspending 0.61 g of sodium hydride (60% oily) in 20 ml of tetrahydrofuran and dissolving 0.73 g of 2-butyn-1-ol in 1 ml of tetrahydrofuran was added dropwise at 0 ° C. and stirred for 10 minutes. A solution prepared by dissolving 1.75 g of 4,6-dichloro-5-fluoropyrimidine in 5 ml of tetrahydrofuran was added dropwise to this mixed solution, followed by stirring at 0 ° C. for 90 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1.8 g of 4- (2-butynyloxy) -6-chloro-5-fluoropyrimidine.
4- (2-butynyloxy) -6-chloro-5-fluoropyrimidine

¹Ｈ−ＮＭＲ：１．７９（ｔ，３Ｈ），５．００（ｑ，２Ｈ），８．２９（ｓ，１Ｈ）

¹ H-NMR: 1.79 (t, 3H), 5.00 (q, 2H), 8.29 (s, 1H)

Reference production example 2
In 24 ml of tetrahydrofuran, 1.05 g of sodium hydride (60% oily) was suspended. A solution of 1.42 g of 2-butyn-1-ol dissolved in 8 ml of tetrahydrofuran was slowly added dropwise at room temperature and stirred for 20 minutes. A solution prepared by dissolving 3 g of 4,6-dichloropyrimidine in 8 ml of tetrahydrofuran was slowly added dropwise to this mixed solution at 0 ° C. and stirred for 4 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 3.16 g of 4-chloro-6- (2-butynyloxy) pyrimidine.
4-Chloro-6- (2-butynyloxy) pyrimidine

融点：４３．５℃

Melting point: 43.5 ° C

Reference production example 3
A solution obtained by suspending 0.58 g of sodium hydride (60% oily) in 20 ml of tetrahydrofuran and dissolving 0.88 g of 2-pentyn-1-ol in 1 ml of tetrahydrofuran was added dropwise at 0 ° C. and stirred for 10 minutes. A solution prepared by dissolving 2 g of 4,6-dichloro-5-fluoropyrimidine in 5 ml of tetrahydrofuran was added dropwise to this mixture at 0 ° C. and stirred for 70 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 2.31 g of 4-chloro-5-fluoro-6- (2-pentynyloxy) pyrimidine.
4-chloro-5-fluoro-6- (2-pentynyloxy) pyrimidine

¹Ｈ−ＮＭＲ：１．１５（ｔ，３Ｈ），２．２４（ｑｔ，２Ｈ），５．０９（ｔ，２Ｈ），８．３６（ｓ，１Ｈ）

¹ H-NMR: 1.15 (t, 3H), 2.24 (qt, 2H), 5.09 (t, 2H), 8.36 (s, 1H)

Reference production example 4
To 4 ml of acetonitrile, 0.3 g of 4,6-dichloropyrimidine, 0.83 g of potassium carbonate and 0.43 g of cis-2,6-dimethylhexahydroazepine hydrochloride were added and stirred at 60 ° C. for 4 hours. Thereafter, a saturated aqueous ammonium chloride solution was poured into the reaction mixture which was allowed to cool to near room temperature, and extracted three times with tert-butyl methyl ether. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.3 g of 1- (6-chloropyrimidin-4-yl) -cis-2,6-dimethylhexahydroazepine.
1- (6-Chloropyrimidin-4-yl) -cis-2,6-dimethylhexahydroazepine

¹Ｈ−ＮＭＲ：０．９２〜２．１３（ｍ，１３Ｈ），２．７１（ｄｄ，０．４Ｈ），２．９８〜３．０９（ｍ，１．２Ｈ），３．６０〜３．６９（ｍ，０．４Ｈ），４．０６（ｄ，０．４Ｈ），４．７４〜４．８５（ｍ，０．６Ｈ），６．２５（ｓ，０．６Ｈ），６．４０（ｓ，０．４Ｈ），８．３５（ｓ，１Ｈ）
ＧＣ−ＭＳ：２３９（Ｍ＋）

¹ H-NMR: 0.92 to 2.13 (m, 13H), 2.71 (dd, 0.4H), 2.98 to 3.09 (m, 1.2H), 3.60 to 3. 69 (m, 0.4H), 4.06 (d, 0.4H), 4.74 to 4.85 (m, 0.6H), 6.25 (s, 0.6H), 6.40 ( s, 0.4H), 8.35 (s, 1H)
GC-MS: 239 (M +)

Reference production example 5
0.54 g of lithium aluminum hydride was suspended in 20 ml of tetrahydrofuran, 1 g of hexahydro-cis-3,7-dimethylazepin-2-one was added little by little at 0 ° C., and the mixture was heated to reflux for 10 hours. After cooling to 0 ° C., 0.54 ml of water, 0.54 ml of 15% aqueous sodium hydroxide solution and 1.62 ml of water were added in this order, and after stirring for 30 minutes, anhydrous magnesium sulfate was added and the mixture was filtered through Celite. To the obtained filtrate, 8.4 ml of hydrogen chloride-diethyl ether solution (1 mol / L) was added at 0 ° C., stirred for 1 hour, and concentrated to obtain 1 g of cis-2,6-dimethylhexahydroazepine hydrochloride. .
Cis-2,6-dimethylhexahydroazepine hydrochloride

¹Ｈ−ＮＭＲ：１．０１（ｄ，３Ｈ），１．２１〜１．３３（ｍ，１Ｈ），１．４８（ｄ，３Ｈ），１．６０〜１．７２（ｍ，２Ｈ），１．７９〜２．０１（ｍ，３Ｈ），２．１２〜２．２１（ｍ，１Ｈ），２．７７〜２．８８（ｍ，１Ｈ），３．２２（ｂｒｄ，１Ｈ），３．５４（ｂｒｓ，１Ｈ），９．４４（ｂｒ，２Ｈ）

¹ H-NMR: 1.01 (d, 3H), 1.21-1.33 (m, 1H), 1.48 (d, 3H), 1.60 to 1.72 (m, 2H), 1 .79 to 2.01 (m, 3H), 2.12 to 2.21 (m, 1H), 2.77 to 2.88 (m, 1H), 3.22 (brd, 1H), 3.54 (Brs, 1H), 9.44 (br, 2H)

Reference production example 6
In 80 ml of ethanol, 5 g of 2,6-dimethylcyclohexanone and 5.51 g of hydroxylamine hydrochloride were suspended, and 9.4 g of pyridine was added dropwise at 0 ° C. After stirring at room temperature for 4 hours, the reaction mixture was concentrated. Water was added to the residue and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 3.1 g of cis-2,6-dimethylcyclohexanone oxime and 1.3 g of trans-2,6-dimethylcyclohexanone oxime.
Cis-2,6-dimethylcyclohexanone oxime

¹Ｈ−ＮＭＲ：１．１９（ｄ，３Ｈ），１．２１（ｄ，３Ｈ），１．４２〜１．５１（ｍ，１Ｈ），１．５３〜１．８５（ｍ，５Ｈ），２．５８〜２．６７（ｍ，１Ｈ），３．３９〜３．４８（ｍ，１Ｈ），８．５８（ｂｒｓ，１Ｈ）
トランス−２，６−ジメチルシクロヘキサノンオキシム

¹ H-NMR: 1.19 (d, 3H), 1.21 (d, 3H), 1.42 to 1.51 (m, 1H), 1.53 to 1.85 (m, 5H), 2 .58-2.67 (m, 1H), 3.39-3.48 (m, 1H), 8.58 (brs, 1H)
Trans-2,6-dimethylcyclohexanone oxime

¹Ｈ−ＮＭＲ：１．０８（ｄ，３Ｈ），１．１２（ｄ，３Ｈ），１．１４〜１．２５（ｍ，１Ｈ），１．５２〜１．７２（ｍ，４Ｈ），１．８３〜１．９１（ｍ，１Ｈ），２．３２〜２．４６（ｍ，１Ｈ），３．６４〜３．６９（ｍ，１Ｈ），８．８１（ｓ，１Ｈ）

¹ H-NMR: 1.08 (d, 3H), 1.12 (d, 3H), 1.14 to 1.25 (m, 1H), 1.52 to 1.72 (m, 4H), 1 .83 to 1.91 (m, 1H), 2.32 to 2.46 (m, 1H), 3.64 to 3.69 (m, 1H), 8.81 (s, 1H)

Reference production example 7
To 40 ml of xylene, 3.1 g of cis-2,6-dimethylcyclohexanone oxime and 12 g of polyphosphoric acid were added and stirred at 100 ° C. for 10 hours. Thereafter, ice water was poured into the reaction mixture which was allowed to cool to near room temperature, potassium carbonate was added, and the mixture was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.5 g of hexahydro-cis-3,7-dimethylazepin-2-one.
Hexahydro-cis-3,7-dimethylazepin-2-one

¹Ｈ−ＮＭＲ：１．３１（ｄ，３Ｈ），１．９１（ｄ，３Ｈ），１．２６〜１．３６（ｍ，１Ｈ），１．４０〜１．５１（ｍ，１Ｈ），１．６０〜１．７６（３Ｈ），１．９１〜１．９７（ｍ，１Ｈ），２．４８〜２．５６（ｍ，１Ｈ），３．４９〜３．５８（ｍ，１Ｈ），５．３６（ｂｒｓ，１Ｈ）

¹ H-NMR: 1.31 (d, 3H), 1.91 (d, 3H), 1.26 to 1.36 (m, 1H), 1.40 to 1.51 (m, 1H), 1 .60 to 1.76 (3H), 1.91 to 1.97 (m, 1H), 2.48 to 2.56 (m, 1H), 3.49 to 3.58 (m, 1H), 5 .36 (brs, 1H)

Reference production example 8
In 15 ml of tetrahydrofuran, 0.96 g of lithium aluminum hydride was suspended. To this, 1 g of 3,3-dimethyl-2,5-pyrrolidinedione was added little by little at 0 ° C., and the mixture was heated to reflux for 12 hours. After cooling to 0 ° C., 0.96 ml of water, 0.96 ml of 15% aqueous sodium hydroxide solution and 2.88 ml of water were added in this order, and after stirring for 30 minutes, anhydrous magnesium sulfate was added and filtered through Celite. To the obtained filtrate, 15.74 ml of hydrogen chloride-diethyl ether solution (1 mol / L) was added at 0 ° C., stirred for 1 hour, and concentrated to obtain 0.45 g of 3,3-dimethylpyrrolidine hydrochloride.
3,3-dimethylpyrrolidine hydrochloride

¹Ｈ−ＮＭＲ：１．１９（ｓ，６Ｈ），１．７９〜１．８４（ｍ，２Ｈ），３．０１〜３．０７（ｍ，２Ｈ），３．４３〜３．５１（ｍ，２Ｈ），９．３７（ｂｒ，２Ｈ）

¹ H-NMR: 1.19 (s, 6H), 1.79 to 1.84 (m, 2H), 3.01 to 3.07 (m, 2H), 3.43 to 3.51 (m, 2H), 9.37 (br, 2H)

Reference production example 9
10 g of 3,3-dimethylsuccinic acid and 102.7 g of urea were stirred at 160 ° C. for 10 hours. Thereafter, water was added to the reaction mixture that had been allowed to cool to about 100 ° C., the mixture was allowed to cool to about room temperature, and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 7.8 g of 3,3-dimethyl-2,5-pyrrolidinedione.
3,3-dimethyl-2,5-pyrrolidinedione

¹Ｈ−ＮＭＲ：１．３５（ｓ，６Ｈ），２．６０（ｓ，２Ｈ），８．３６（ｂｒ，１Ｈ）

¹ H-NMR: 1.35 (s, 6H), 2.60 (s, 2H), 8.36 (br, 1H)

Next, compound (II) will be described.
In general formula 2
Examples of the C3-C7 alkynyl group represented by R ⁴ include a 2-propynyl group, 2-butynyl group, 1-methyl-2-butynyl group, 2-pentynyl group, 4,4-dimethyl-2-pentynyl group, 1 -Methyl-2-propynyl group and 1,1-dimethyl-2-propynyl group,
Examples of the C4-C7 alkanediyl group represented by X ² include butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group. Named,
Examples of the C4-C7 alkenediyl group include 2-butene-1,4-diyl group, 2-pentene-1,5-diyl group, 2-hexene-1,6-diyl group, and 3-hexene-1,6- A diyl group, etc.
Examples of the halogen atom represented by R ⁵ include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a sec-propyl group, and a tert-propyl group. A butyl group is mentioned.
Examples of the C1-C3 alkyl group represented by R ⁶ include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
Examples of the group represented by A include A ¹ and A ² described above,
Examples of A ¹ include pyrrolidino group, 2-methylpyrrolidino group, 2-ethylpyrrolidino group, 2-n-propylpyrrolidino group, 2-isopropylpyrrolidino group, 2-tert-butylpyrrolidino group, 2- Fluoropyrrolidino group, 2-trifluoromethylpyrrolidino group, 3-methylpyrrolidino group, 3-ethylpyrrolidino group, 3-trifluoromethylpyrrolidino group, 2,5-dimethylpyrrolidino group, 3,4- Dimethylpyrrolidino group, 3,3-dimethylpyrrolidino group, piperidino group, 2-methylpiperidino group, 2-ethylpiperidino group, 2-n-propylpiperidino group, 2-isopropylpiperidino group, 2-tert-butylpiperidino group Group, 2-sec-butylpiperidino group, 2-fluoropiperidino group, 2-bromopiperidino group, 2-trifluoromethylpiperidino group Group, 3-methylpiperidino group, 3-ethylpiperidino group, 3-n-propylpiperidino group, 3-isopropylpiperidino group, 3-tert-butylpiperidino group, 3-sec-butylpiperidino group, 3-fluoropiperidino group Group, 3-bromopiperidino group, 3-trifluoromethylpiperidino group, 4-methylpiperidino group, 4-ethylpiperidino group, 4-n-propylpiperidino group, 4-isopropylpiperidino group, 4-tert-butylpiperidino group Group, 4-trifluoromethylpiperidino group, 2,6-dimethylpiperidino group, 2,4-dimethylpiperidino group, 2,5-dimethylpiperidino group, 3,5-dimethylpiperidino group Group, 2,2, -dimethylpiperidino group, 3,3-dimethylpiperidino group, 4,4-dimethylpiperidino group, 3-ethyl-6-methylpiperidino group 3-ethyl-5-methylpiperidino group, 3,5-diethylpiperidino group, 3,5-di-n-propylpiperidino group, 3,5-diisopropylpiperidino group, 2,3-dimethylpiperidino group Group, 3,3,5-trimethylpiperidino group, 2,3,5,6-tetramethylpiperidino group, 3,3,5,5-tetramethylpiperidino group, 3,3-difluoro Piperidino group, 4,4-difluoropiperidino group, 3-fluoro-3-methylpiperidino group, hexameleimino group, 2-methylhexamerenimino group, 2-ethylhexamerenimino group, 2-n-propyl Hexamelenimino group, 2-Isopropylhexamelenimino group, 2-tert-Butylhexamelenimino group, 3-Methylhexameleneimino group, 3-Ethylhexamyleneimino group, 3-n-propyl Xameleneimino group, 3-isopropylhexameneimino group, 4-methylhexameneimino group, 4-ethylhexamyleneimino group, 4-n-propylhexamyleneimino group, 4-isopropylhexamyleneimino group, 5-methylhexamylene Imino group, heptamethyleneimino group, 3-pyrrolino group, 3-methyl-3-pyrrolino group, 3,4-dimethyl-3-pyrrolino group, 2,5-dimethyl-3-pyrrolino group, 1,2,3 6-tetrahydropyridino group, 6-methyl-1,2,3,6-tetrahydropyridino group, 5-methyl-1,2,3,6-tetrahydropyridino group, 4-methyl-1,2,3 , 6-tetrahydropyridino group, 3-methyl-1,2,3,6-tetrahydropyridino group, 2-methyl-1,2,3,6-tetrahydropyridino group, 2,6-dimethyl-1,2,3,6-tetrahydropyridino group, 1,2,3,4,7-pentahydroazepino group, 1,2,3,6,7-pentahydroazepino group Are mentioned,
Examples of A ² include morpholino group, 2-methylmorpholino group, 2-ethylmorpholino group, 3-methylmorpholino group, 3-ethylmorpholino group, 2,6-dimethylmorpholino group, and 2,6-diethylmorpholino group. It is done.

As an aspect of compound (II), the following 1,2,4-thiadiazole compounds are mentioned, for example.
A thiadiazole compound represented by the general formula 2 wherein R ⁴ is a (C3-C7) 2-alkynyl group;
A thiadiazole compound in which R ⁴ is a 2-butynyl group in the general formula 2;
A thiadiazole compound in which R ⁴ is a 2-pentynyl group in the general formula 2;
A thiadiazole compound in which A is A ¹ in the general formula 2;
In the general formula of 2, thiadiazole compound A is represented by A ^2;

A thiadiazole compound represented by the general formula: wherein A is A ¹ and l is 0;
A thiadiazole compound in which A is A ¹ and 1 is 1 or 2 in the general formula 2;
A thiadiazole compound represented by the general formula 2, wherein A is A ¹ , R ⁵ is a C1-C4 alkyl group, and 1 is 1 or 2;
A thiadiazole compound represented by the general formula 2, wherein A is A ¹ , R ⁵ is a methyl group, and 1 is 1 or 2;
A thiadiazole compound in which A is A ¹ and X ² is a butane-1,4-diyl group in the general formula 2;
A thiadiazole compound represented by the general formula: wherein A is A ¹ and X ² is a pentane-1,5-diyl group;
A thiadiazole compound in which A is A ¹ and X ² is a hexane-1,6-diyl group in the general formula 2;

A thiadiazole compound represented by the general formula: wherein A is A ¹ and R ⁵ is a C1-C4 alkyl group;
A thiadiazole compound represented by the general formula: wherein A is A ¹ and R ⁵ is a methyl group;
A thiadiazole compound in which A is A ¹ and X ² is a butane-1,4-diyl group in the general formula 2;
A thiadiazole compound represented by the general formula: wherein A is A ¹ and X ² is a pentane-1,5-diyl group;

A thiadiazole compound represented by the general formula: wherein A is A ² and n is 0;
A thiadiazole compound represented by the general formula: wherein A is A ² and R ⁶ is a methyl group;
In the general formula of 2, A is ^{A 2,} n is 1 or 2, thiadiazole compounds in ^{which R 6} is C1-C3 alkyl group;
A thiadiazole compound represented by the formula: wherein R ⁴ is a (C 3 -C 7) 2 -alkynyl group, A is A ² , and n is 0;
A thiadiazole compound represented by the formula: wherein R ⁴ is a (C3-C7) 2-alkynyl group, A is A ² and R ⁶ is a methyl group;
A thiadiazole compound in which R ⁴ is a (C 3 -C 7) 2 -alkynyl group, A is A ² , n is 1 or 2, and R ⁶ is a C 1 -C 3 alkyl group;

Next, a method for producing compound (II) will be described.
Compound (II) can be produced, for example, according to Production Process Example 1 described below.

Manufacturing process example 3
Compound (II) can be produced by reacting a compound represented by formula (XIV) with a compound represented by formula (XV) in the presence of a base.

〔式中、Ｒ^４及びＡは前記と同じ意味を表し、ｑは１又は２を表す。〕
該反応は通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、tert-ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、カリウムtert-ブトキシド、ナトリウムtert-ブトキシド等のアルカリ金属アルコキシド類が挙げられる。
反応に用いられる試剤の量は、式（XIV）で示される化合物１モルに対して、式（XV）で示される化合物が通常１〜２モルの割合であり、塩基が通常１〜２モルの割合である。
該反応の反応温度は、通常０〜８０℃の範囲であり、反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、乾燥、濃縮する等の後処理操作を行うことにより、化合物（II）を単離することができる。単離された化合物（II）はクロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein, R ⁴ and A represent the same meaning as described above, and q represents 1 or 2. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N, N-dimethylformamide, and nitriles such as acetonitrile. , Sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and alkali metal alkoxides such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the reagent used in the reaction is such that the compound represented by the formula (XV) is usually 1 to 2 mol and the base is usually 1 to 2 mol relative to 1 mol of the compound represented by the formula (XIV). It is a ratio.
The reaction temperature is usually in the range of 0 to 80 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound (II) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound (II) can be further purified by chromatography, recrystallization and the like.

  Next, the manufacturing method of the manufacturing intermediate of compound (II) is demonstrated.

Reference manufacturing process example 5

〔式中、Ａ及びｑは前記と同じ意味を表す。〕
（工程１）
式（XVI）で示される化合物は、３−メチルチオ−５−クロロ−１，２，４−チアジアゾールと式（XV）で示される化合物とを反応させることにより製造することができる。
該反応は溶媒の存在下又は非存在下、塩基の存在下又は非存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、ジエチルエーテル、tert-ブチルメチルエーテル、エチレングリコールジメチルエーテル、１，４−ジオキサン等のエーテル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド等のスルホキシド類、メタノール、エタノール等のアルコール類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては例えば水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物類、炭酸カリウム等の炭酸塩類、カリウムtert-ブトキシド、ナトリウムtert-ブトキシド等のアルカリ金属アルコキシド類が挙げられる。
反応に用いられる試剤の量は、３−メチルチオ−５−クロロ−１，２，４−チアジアゾール１モルに対して、式（XV）で示される化合物が通常１〜２モルの割合であり、塩基が通常１〜２モルの割合である。
該反応の反応温度は、通常０〜８０℃の範囲であり、反応時間は通常０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、乾燥、濃縮する等の後処理操作により、式（XVI）で示される化合物を単離することができる。単離された式（XVI）で示される化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。
（工程２）
式（XIV）で示される化合物は、式（XVI）で示される化合物を酸化剤の存在下で反応させることにより製造することができる。
該反応は通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等の脂肪族ハロゲン化炭化水素類及び水が挙げられる。
反応に用いられる酸化剤としては、例えば３−クロロ過安息香酸、過酸化水素水等の過酸化物が挙げられる。
反応に用いられる試剤の量は、式（XVI）で示される化合物１モルに対して、通常１モル〜過剰量の割合である。
該反応の反応温度は、通常−２０〜３０℃の範囲であり、反応時間は通常瞬時〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、得られた有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、乾燥、濃縮する等の後処理操作を行うことにより、式（XIV）で示される化合物を単離することができる。単離された式（XIV）で示される化合物はクロマトグラフィー、再結晶等によりさらに精製することもできる。

[Wherein, A and q represent the same meaning as described above. ]
(Process 1)
The compound represented by the formula (XVI) can be produced by reacting 3-methylthio-5-chloro-1,2,4-thiadiazole with a compound represented by the formula (XV).
The reaction is carried out in the presence or absence of a solvent, in the presence or absence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane, acid amides such as N, N-dimethylformamide, and nitriles such as acetonitrile. , Sulfoxides such as dimethyl sulfoxide, alcohols such as methanol and ethanol, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, carbonates such as potassium carbonate, and alkali metal alkoxides such as potassium tert-butoxide and sodium tert-butoxide.
The amount of the reagent used in the reaction is usually 1 to 2 mol of the compound represented by the formula (XV) with respect to 1 mol of 3-methylthio-5-chloro-1,2,4-thiadiazole, Is usually a ratio of 1 to 2 mol.
The reaction temperature is usually in the range of 0 to 80 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound represented by the formula (XVI) can be isolated by post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration. The isolated compound represented by the formula (XVI) can be further purified by chromatography, recrystallization and the like.
(Process 2)
The compound represented by the formula (XIV) can be produced by reacting the compound represented by the formula (XVI) in the presence of an oxidizing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform, and water.
Examples of the oxidizing agent used in the reaction include peroxides such as 3-chloroperbenzoic acid and hydrogen peroxide.
The amount of the reagent used in the reaction is usually 1 mol to excess with respect to 1 mol of the compound represented by the formula (XVI).
The reaction temperature of the reaction is usually in the range of −20 to 30 ° C., and the reaction time is usually in the range of instantaneous to 24 hours.
After completion of the reaction, the reaction mixture is extracted with an organic solvent, and the obtained organic layer is washed with an aqueous solution of a reducing agent (for example, sodium sulfite or sodium thiosulfate) or an aqueous solution of a base (for example, sodium bicarbonate) as necessary By performing post-treatment operations such as drying and concentration, the compound represented by the formula (XIV) can be isolated. The isolated compound represented by the formula (XIV) can be further purified by chromatography, recrystallization and the like.

Next, specific examples of compound (II) are shown below.
A thiadiazole compound in which R ⁴ is a 2-propynyl group and A is any of the groups shown below:
Pyrrolidino group, 2-methylpyrrolidino group, 2-ethylpyrrolidino group, 2-n-propylpyrrolidino group, 2-isopropylpyrrolidino group, 2-tert-butylpyrrolidino group, 2-fluoropyrrolidino group, 2 -Trifluoromethylpyrrolidino group, 3-methylpyrrolidino group, 3-ethylpyrrolidino group, 3-trifluoromethylpyrrolidino group, 2,5-dimethylpyrrolidino group, 3,4-dimethylpyrrolidino group, 3 , 3-dimethylpyrrolidino group,
Piperidino group, 2-methylpiperidino group, 2-ethylpiperidino group, 2-n-propylpiperidino group, 2-isopropylpiperidino group, 2-tert-butylpiperidino group, 2-sec-butylpiperidino group, 2-fluoropiperidino group Group, 2-bromopiperidino group, 2-trifluoromethylpiperidino group, 3-methylpiperidino group, 3-ethylpiperidino group, 3-n-propylpiperidino group, 3-isopropylpiperidino group, 3-tert- Butylpiperidino group, 3-sec-butylpiperidino group, 3-fluoropiperidino group, 3-bromopiperidino group, 3-trifluoromethylpiperidino group, 4-methylpiperidino group, 4-ethylpiperidino group, 4-n-propylpiperidino group Group, 4-isopropylpiperidino group, 4-tert-butylpiperidino group, 4-trifluoromethyl Lupiperidino group, 2,6-dimethylpiperidino group, 2,4-dimethylpiperidino group, 2,5-dimethylpiperidino group, 3,5-dimethylpiperidino group, 2,2, -dimethylpi Peridino group, 3,3-dimethylpiperidino group, 4,4-dimethylpiperidino group, 3-ethyl-6-methylpiperidino group, 3-ethyl-5-methylpiperidino group, 3,5-diethylpiperidino group Group, 3,5-di-n-propylpiperidino group, 3,5-diisopropylpiperidino group, 2,3-dimethylpiperidino group, 3,3,5-trimethylpiperidino group, 2,3 , 5,6-tetramethylpiperidino group, 3,3,5,5-tetramethylpiperidino group, 3,3-difluoropiperidino group, 4,4-difluoropiperidino group, 3-fluoro -3-methylpiperidino group,
Hexamelenimino group, 2-methylhexameleneimino group, 2-ethylhexameleneimino group, 2-n-propylhexameleneimino group, 2-isopropylhexameleminomino group, 2-tert-butylhexameleminomino group, 3 -Methylhexameleneimino group, 3-ethylhexameleneimino group, 3-n-propylhexameleneimino group, 3-isopropylhexameleneimino group, 4-methylhexameleneimino group, 4-ethylhexameleneimino group, 4 -N-propylhexamelelimino group, 4-isopropylhexamelelimino group, 5-methylhexameleminino group,
Heptamethyleneimino group,
Morpholino group, 2-methylmorpholino group, 2-ethylmorpholino group, 3-methylmorpholino group, 3-ethylmorpholino group, 2,6-dimethylmorpholino group and 2,6-diethylmorpholino group.

A thiadiazole compound in which R ⁴ is a 2-butynyl group and A is any of the groups shown below:
Pyrrolidino group, 2-methylpyrrolidino group, 2-ethylpyrrolidino group, 2-n-propylpyrrolidino group, 2-isopropylpyrrolidino group, 2-tert-butylpyrrolidino group, 2-fluoropyrrolidino group, 2 -Trifluoromethylpyrrolidino group, 3-methylpyrrolidino group, 3-ethylpyrrolidino group, 3-trifluoromethylpyrrolidino group, 2,5-dimethylpyrrolidino group, 3,4-dimethylpyrrolidino group, 3 , 3-dimethylpyrrolidino group,
Piperidino group, 2-methylpiperidino group, 2-ethylpiperidino group, 2-n-propylpiperidino group, 2-isopropylpiperidino group, 2-tert-butylpiperidino group, 2-sec-butylpiperidino group, 2-fluoropiperidino group Group, 2-bromopiperidino group, 2-trifluoromethylpiperidino group, 3-methylpiperidino group, 3-ethylpiperidino group, 3-n-propylpiperidino group, 3-isopropylpiperidino group, 3-tert- Butylpiperidino group, 3-sec-butylpiperidino group, 3-fluoropiperidino group, 3-bromopiperidino group, 3-trifluoromethylpiperidino group, 4-methylpiperidino group, 4-ethylpiperidino group, 4-n-propylpiperidino group Group, 4-isopropylpiperidino group, 4-tert-butylpiperidino group, 4-trifluoromethyl Lupiperidino group, 2,6-dimethylpiperidino group, 2,4-dimethylpiperidino group, 2,5-dimethylpiperidino group, 3,5-dimethylpiperidino group, 2,2, -dimethylpi Peridino group, 3,3-dimethylpiperidino group, 4,4-dimethylpiperidino group, 3-ethyl-6-methylpiperidino group, 3-ethyl-5-methylpiperidino group, 3,5-diethylpiperidino group Group, 3,5-di-n-propylpiperidino group, 3,5-diisopropylpiperidino group, 2,3-dimethylpiperidino group, 3,3,5-trimethylpiperidino group, 2,3 , 5,6-tetramethylpiperidino group, 3,3,5,5-tetramethylpiperidino group, 3,3-difluoropiperidino group, 4,4-difluoropiperidino group, 3-fluoro -3-methylpiperidino group,
Hexamelenimino group, 2-methylhexameleneimino group, 2-ethylhexameleneimino group, 2-n-propylhexameleneimino group, 2-isopropylhexameleminomino group, 2-tert-butylhexameleminomino group, 3 -Methylhexameleneimino group, 3-ethylhexameleneimino group, 3-n-propylhexameleneimino group, 3-isopropylhexameleneimino group, 4-methylhexameleneimino group, 4-ethylhexameleneimino group, 4 -N-propylhexamelelimino group, 4-isopropylhexamelelimino group, 5-methylhexameleminino group,
Heptamethyleneimino group,
Morpholino group, 2-methylmorpholino group, 2-ethylmorpholino group, 3-methylmorpholino group, 3-ethylmorpholino group, 2,6-dimethylmorpholino group and 2,6-diethylmorpholino group.

A thiadiazole compound in which R ⁴ is a 1-methyl-2-butynyl group and A is any of the groups shown below:
Pyrrolidino group, 2-methylpyrrolidino group, 2-ethylpyrrolidino group, 2-n-propylpyrrolidino group, 2-isopropylpyrrolidino group, 2-tert-butylpyrrolidino group, 2-fluoropyrrolidino group, 2 -Trifluoromethylpyrrolidino group, 3-methylpyrrolidino group, 3-ethylpyrrolidino group, 3-trifluoromethylpyrrolidino group, 2,5-dimethylpyrrolidino group, 3,4-dimethylpyrrolidino group, 3 , 3-dimethylpyrrolidino group,
Piperidino group, 2-methylpiperidino group, 2-ethylpiperidino group, 2-n-propylpiperidino group, 2-isopropylpiperidino group, 2-tert-butylpiperidino group, 2-sec-butylpiperidino group, 2-fluoropiperidino group Group, 2-bromopiperidino group, 2-trifluoromethylpiperidino group, 3-methylpiperidino group, 3-ethylpiperidino group, 3-n-propylpiperidino group, 3-isopropylpiperidino group, 3-tert- Butylpiperidino group, 3-sec-butylpiperidino group, 3-fluoropiperidino group, 3-bromopiperidino group, 3-trifluoromethylpiperidino group, 4-methylpiperidino group, 4-ethylpiperidino group, 4-n-propylpiperidino group Group, 4-isopropylpiperidino group, 4-tert-butylpiperidino group, 4-trifluoromethyl Lupiperidino group, 2,6-dimethylpiperidino group, 2,4-dimethylpiperidino group, 2,5-dimethylpiperidino group, 3,5-dimethylpiperidino group, 2,2, -dimethylpi Peridino group, 3,3-dimethylpiperidino group, 4,4-dimethylpiperidino group, 3-ethyl-6-methylpiperidino group, 3-ethyl-5-methylpiperidino group, 3,5-diethylpiperidino group Group, 3,5-di-n-propylpiperidino group, 3,5-diisopropylpiperidino group, 2,3-dimethylpiperidino group, 3,3,5-trimethylpiperidino group, 2,3 , 5,6-tetramethylpiperidino group, 3,3,5,5-tetramethylpiperidino group, 3,3-difluoropiperidino group, 4,4-difluoropiperidino group, 3-fluoro -3-methylpiperidino group,
Hexamelenimino group, 2-methylhexameleneimino group, 2-ethylhexameleneimino group, 2-n-propylhexameleneimino group, 2-isopropylhexameleminomino group, 2-tert-butylhexameleminomino group, 3 -Methylhexameleneimino group, 3-ethylhexameleneimino group, 3-n-propylhexameleneimino group, 3-isopropylhexameleneimino group, 4-methylhexameleneimino group, 4-ethylhexameleneimino group, 4 -N-propylhexamelelimino group, 4-isopropylhexamelelimino group, 5-methylhexameleminino group,
Heptamethyleneimino group,
Morpholino group, 2-methylmorpholino group, 2-ethylmorpholino group, 3-methylmorpholino group, 3-ethylmorpholino group, 2,6-dimethylmorpholino group and 2,6-diethylmorpholino group.

A thiadiazole compound in which R ⁴ is a 2-pentynyl group and A is any of the groups shown below:
Pyrrolidino group, 2-methylpyrrolidino group, 2-ethylpyrrolidino group, 2-n-propylpyrrolidino group, 2-isopropylpyrrolidino group, 2-tert-butylpyrrolidino group, 2-fluoropyrrolidino group, 2 -Trifluoromethylpyrrolidino group, 3-methylpyrrolidino group, 3-ethylpyrrolidino group, 3-trifluoromethylpyrrolidino group, 2,5-dimethylpyrrolidino group, 3,4-dimethylpyrrolidino group, 3 , 3-dimethylpyrrolidino group,
Piperidino group, 2-methylpiperidino group, 2-ethylpiperidino group, 2-n-propylpiperidino group, 2-isopropylpiperidino group, 2-tert-butylpiperidino group, 2-sec-butylpiperidino group, 2-fluoropiperidino group Group, 2-bromopiperidino group, 2-trifluoromethylpiperidino group, 3-methylpiperidino group, 3-ethylpiperidino group, 3-n-propylpiperidino group, 3-isopropylpiperidino group, 3-tert- Butylpiperidino group, 3-sec-butylpiperidino group, 3-fluoropiperidino group, 3-bromopiperidino group, 3-trifluoromethylpiperidino group, 4-methylpiperidino group, 4-ethylpiperidino group, 4-n-propylpiperidino group Group, 4-isopropylpiperidino group, 4-tert-butylpiperidino group, 4-trifluoromethyl Lupiperidino group, 2,6-dimethylpiperidino group, 2,4-dimethylpiperidino group, 2,5-dimethylpiperidino group, 3,5-dimethylpiperidino group, 2,2, -dimethylpi Peridino group, 3,3-dimethylpiperidino group, 4,4-dimethylpiperidino group, 3-ethyl-6-methylpiperidino group, 3-ethyl-5-methylpiperidino group, 3,5-diethylpiperidino group Group, 3,5-di-n-propylpiperidino group, 3,5-diisopropylpiperidino group, 2,3-dimethylpiperidino group, 3,3,5-trimethylpiperidino group, 2,3 , 5,6-tetramethylpiperidino group, 3,3,5,5-tetramethylpiperidino group, 3,3-difluoropiperidino group, 4,4-difluoropiperidino group, 3-fluoro -3-methylpiperidino group,
Hexamelenimino group, 2-methylhexameleneimino group, 2-ethylhexameleneimino group, 2-n-propylhexameleneimino group, 2-isopropylhexameleminomino group, 2-tert-butylhexameleminomino group, 3 -Methylhexameleneimino group, 3-ethylhexameleneimino group, 3-n-propylhexameleneimino group, 3-isopropylhexameleneimino group, 4-methylhexameleneimino group, 4-ethylhexameleneimino group, 4 -N-propylhexamelelimino group, 4-isopropylhexamelelimino group, 5-methylhexameleminino group,
Heptamethyleneimino group,
Morpholino group, 2-methylmorpholino group, 2-ethylmorpholino group, 3-methylmorpholino group, 3-ethylmorpholino group, 2,6-dimethylmorpholino group and 2,6-diethylmorpholino group.

Hereinafter, although the manufacture example of compound (II) used in this invention composition is demonstrated in more detail, this invention is not limited only to these examples.
Specific production examples of the compound (II) used in the composition of the present invention produced according to the description of the production steps (Chemical 29), (Chemical 30) and reaction conditions in each step are shown. . In the production examples and reference production examples, ¹ H-NMR indicates data obtained by measuring tetramethylsilane as an internal standard in a deuterated chloroform solvent, except for special cases.

Production Example 6 [Production Example of Compound (II-1)]
533 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole was dissolved in 4 ml of N, N-dimethylformamide, and 198 mg of 3-methylpiperidine was added dropwise thereto at room temperature, followed by stirring for 6 hours. The reaction mixture was diluted with tert-butyl methyl ether, 10% hydrochloric acid was added, and the mixture was extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and 4 ml of chloroform was mixed with the resulting residue. 1.52 g of 3-chloroperbenzoic acid (content: 65% by weight) was added to the mixture under ice cooling, and the mixture was stirred at room temperature for 6 hours. The reaction mixture was washed with 10% aqueous sodium sulfite and saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and 4 ml of N, N-dimethylformamide and 168 mg of 2-pentyn-1-ol were mixed with the resulting residue. 120 mg of sodium hydride (oil, content: 60% by weight) was added thereto under ice-cooling, and the mixture was stirred for 15 minutes and further stirred at room temperature for 6 hours. To the reaction mixture was added saturated brine, and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 145 mg of 3- (2-pentynyloxy) -5- (3-methylpiperidino) -1,2,4-thiadiazole (hereinafter referred to as compound (II-1)). It was.
Compound (II-1)

^１Ｈ−ＮＭＲ（ＣＤＣｌ_３、ＴＭＳ）、δ（ｐｐｍ）：４．９１（ｓ、２H），３．７３（ｂｒ、２H），３．０５（ｔ、１H），２．７２（ｔ、１H），２．２２（ｍ、２H），１．８９−１．５４（ｍ、４H），１．２１−１．０６（ｍ、４H），０．９４（ｄ、３H）
EI-EI-Mass：m/e＝２６５（Ｍ^＋）

¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 4.91 (s, 2H), 3.73 (br, 2H), 3.05 (t, 1H), 2.72 (t, 1H ), 2.22 (m, 2H), 1.89-1.54 (m, 4H), 1.21-1.06 (m, 4H), 0.94 (d, 3H)
EI-EI-Mass: m / e = 265 (M ⁺ )

Production Example 7 [Production Example of Compound (II-2)]
Production Example except that 226 mg of 3,5-dimethylpiperidine (8: 2 isomer mixture) was used instead of 3-methylpiperidine, and 2-butyn-1-ol was used instead of 2-pentyn-1-ol 6 was carried out, and silica gel thin layer chromatography of 3- (2-butynyloxy) -5- (3,5-dimethylpiperidino) -1,2,4-thiadiazole (developing solvent; hexane / ethyl acetate) ) 55 mg of a low polar component compound (hereinafter referred to as compound (II-2a)) and 22 mg of a high polar component compound (hereinafter referred to as compound (II-2b)) were obtained.

化合物（II−２ａ）
融点 １０４．４℃
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３、ＴＭＳ）、δ（ｐｐｍ）：４．８９（ｓ、２H），３．７４（ｂｒ、２H），２．５７（ｔ、２H），１．９２−１．７０（ｍ、６H），０．９２（ｄ、６H），０．８１（ｑ、１H）
EI-Mass：m/e＝２６５（Ｍ^＋）
化合物（II−２ｂ）
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３、ＴＭＳ）、δ（ｐｐｍ）：４．８８（ｓ、２Ｈ），３．５０（ｂｒ、２Ｈ），３．０６（ｂｒ、２Ｈ），２．０３（ｍ、２Ｈ），１．８６（ｓ、３Ｈ），１．４８（ｍ、２Ｈ），０．９５（ｍ、６Ｈ）
EI-Mass：m/e＝２６５（Ｍ^＋）

Compound (II-2a)
Melting point 104.4 ° C
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 4.89 (s, 2H), 3.74 (br, 2H), 2.57 (t, 2H), 1.92-1.70 (M, 6H), 0.92 (d, 6H), 0.81 (q, 1H)
EI-Mass: m / e = 265 (M ⁺ )
Compound (II-2b)
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 4.88 (s, 2H), 3.50 (br, 2H), 3.06 (br, 2H), 2.03 (m, 2H) ), 1.86 (s, 3H), 1.48 (m, 2H), 0.95 (m, 6H)
EI-Mass: m / e = 265 (M ⁺ )

Production Example 8 [Production Example of Compound (II-3)]
The same operation as in Production Example 6 was performed except that 235 mg of 2,6-dimethylmorpholine (isomer mixture) was used instead of 3-methylpiperidine, and 3- (2-pentynyloxy) -5- (2,6 -Dimethylmorpholino) -1,2,4-thiadiazole compound having a low polarity (hereinafter referred to as Compound (II-3a)) 172 mg and compound having a high polarity component (hereinafter referred to as Compound (II-3b)). ) 66 mg was obtained.

化合物（II−３ａ）
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３、ＴＭＳ）、δ（ｐｐｍ）：４．９１（ｄ、２H），３．７７−３．４４（ｍ、４H），２．８５（ｔ、２H），２．２１（ｍ、２H），１．２３（ｍ、６H），１．１２（ｔ、３H）
EI-Mass：m/e＝２８１（Ｍ^＋）
化合物（II−３ｂ）
^１Ｈ−ＮＭＲ（ＣＤＣｌ_３、ＴＭＳ）、δ（ｐｐｍ）：４．９１（ｔ、２H），４．１２（ｍ、２H），３．５６（ｍ、２H），３．１７（ｍ、２H），２．２４（ｍ、２H），１．２５（ｄ、６H），１．１４（ｔ、３H）
EI-Mass：m/e＝２８１（Ｍ^＋）

Compound (II-3a)
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 4.91 (d, 2H), 3.77-3.44 (m, 4H), 2.85 (t, 2H), 2.21 (M, 2H), 1.23 (m, 6H), 1.12 (t, 3H)
EI-Mass: m / e = 281 (M ⁺ )
Compound (II-3b)
¹ H-NMR (CDCl ₃ , TMS), δ (ppm): 4.91 (t, 2H), 4.12 (m, 2H), 3.56 (m, 2H), 3.17 (m, 2H) ), 2.24 (m, 2H), 1.25 (d, 6H), 1.14 (t, 3H)
EI-Mass: m / e = 281 (M ⁺ )

  Next, compound (III) will be described. In the following, each page described after the compound name means a page described in The Pesticide Manual, Thirteenth Edition (edited by Clive Tomlin, published by The British Crop Protection Council and The Royal Society of Chemistry, 2003). ing. In the composition of the present invention, pymetrozine (generic name) means (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one. (Pages 840 to 841).

Pests for which the composition of the present invention is effective include, for example, arthropods such as insects and mites, and linear animals such as nematodes, and specific examples thereof include the following.

Hemiptera: Insects such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Nephotettix cincticeps, EkioaAphi gossypii), Aphids such as Myzus persicae, Stink bugs, Trialeurodes vaporariorum, Bemisia tabaci, Silverleaf whiteflies (Bemisia argentifolii), Whitefly, Etc .;

Lepidopterous pests: Chilo suppressalis, Cnaphalocrocis medinalis, European corn borer (Ostrinia nubilalis), Japanese moths (Parapediasia teterrella) and other species, Spodoptera pod, Spodoptera pod ), Mamestra brassicae, Agrotis ipsilon, Trichoplusia spp., Heliothis spp., Helicoverpa spp., Earias spp. , White butterflies such as Pieris rapae crucivora, Adoxophyes orana fasciata, Grapholita molesta, Cydia pomonella, etc., Carposina niponensis Lyonetia clerkella) Subfraction such as apple leaf miner (Phyllonorycter ringoniella), Kohamoguriga such as oranges leafminer (Phyllocnistis citrella), Suga such as diamondback moth (Plutela xylostella), Kibaga such as pink bollworm (Pectinophora gossypiella), Tiger Moth class, Hirozukoga, and the like;

Diptera: Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus, etc., Adeses aegypti, Aedes albopictus, etc. , Chironomidae, Musca domestica, Muscina stabulans, and other houseflies, fly flies, sarcophaga, flies flies, Delia platura, onion flies, flies, flies , Butterflies, flyfish, fly, sand flies, leafhoppers, etc .;

  Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), corn root worms such as Southern corn root worm (Diabrotica undecimpunctata howardi); Weevil such as Sitophilus zeamais, rice weevil (Lissorhoptrus oryzophilus), weevil (Callosobruchuys chienensis), weevil (A), euphorus oleum (Tribo) femoralis, horned beetle (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata), etc., horn beetles, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), etc. Na compound, Hirata beetles such, Naga Shinkuimushi acids, Cerambycidae such, Aoba ants backlash Staphylinidae (Paederus fuscipes), etc.;

Thripidae pests: Thrips palmi and other Thrips palmi, Frankliniella occidentalis and other Frankliniella genus, Stiltothrips dorsalis and other thrips etc;

Hymenoptera: bees, ants, wasps, etc .;
Reticulate pests: cockroaches, German cockroaches, etc .;
Direct insect pests: grasshoppers, vignetting, etc .;
Lepidoptera: insect fleas;
Lice pests: human lice etc .;
Termite pests: termites, etc .;

Acarina: Tetranychus urticae, Kanzawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), spider mites (Aculops pelekt), ali Dust mites, Dust mites (Polyphagotarsonemus latus), Dustma mites (Haemaphysalis longicornis), Dick tick (Haemaphysalis flava), Dermacentor taxodes (Dermacentor taxodes) ), Tick such as Boophilus microplus, Mite such as Tyrophagus putrescentiae, Dermatophagoides farinae, Leopard such as Dermatophagoides ptrenyssnus Crawfish ticks (Cheyletus eruditus), crawfish ticks (Cheyletus malaccensis), crested ticks (Cheyletus moorei), etc .;

Nematodes: Southern nematode nematode (Pratylenchus coffeae), Red beetle nematode (Pratylenchus fallax), Soy bean nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), Red beetle nematode (Meloidogyne moth) etc.

  In the composition of the present invention, the mixing ratio of the compound (I) or the compound (II) and the compound (III) is not particularly limited, but is usually a ratio of 200: 1 to 1:30 by weight, preferably 125: The ratio is 1-5: 1.

  Next, formulation examples of the composition of the present invention are shown.

  The composition of the present invention can be used only by mixing the compound (I) or the compound (II) and the compound (III). Usually, the compound (I) or the compound (II) and the compound (III) are combined. Mix, mix with solid carrier, liquid carrier and / or gaseous carrier, add adjuvant for formulation such as surfactant, sticking agent, dispersant, stabilizer, etc. if necessary, wettable powder, suspension Or granules, dry flowables, emulsions, aqueous solutions, oils, smoke agents, aerosols, microcapsules, etc., or compound (I) or compound (II) and compound (III) Are formulated as described above, and optionally further diluted with water, and then the respective preparations are mixed and used. In these preparations, the active ingredient compounds are generally contained in a total amount of 0.05 to 95% by weight.

  Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fusami clay, acidic clay), talc, ceramics, other inorganic minerals (sericite, quartz, Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and the like. (Methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.) , Esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyroni Ril, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), Examples include dimethyl sulfoxide and vegetable oils (soybean oil, cottonseed oil, etc.).

  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

  Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. can give.

  Other formulation adjuvants include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides. , Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-ditertiarybutyl-4-methylphenol), BHA (2-tersia) And mixtures thereof, vegetable oils, mineral oils, and fatty acids or esters thereof.

  Base materials for poisonous baits include, for example, bait ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and children such as pepper powder And anti-fouling agents for pets, cheese flavors, onion flavors, and pest-attracting flavors such as peanut oil.

  The pest control method of the present invention is usually performed by applying the composition of the present invention to a pest or a pest habitat.

When the composition of the present invention is used for agriculture and forestry, the application amount is usually 0.1 to 1000 g, preferably 10 to 500 g, in the amount of the compound of the present invention per 1000 m ² . When the composition of the present invention is formulated into an emulsion, wettable powder, flowable agent, microcapsule, etc., the active ingredient concentration is usually 1 to 10,000 ppm, preferably 10 to 500 ppm. When the composition of the present invention is formulated into granules, powders or the like, it is usually applied as it is.

  The composition of the present invention can be used by foliar treatment for plants such as crops to be protected from pests, and treated in a nursery or planting plant before planting a crop seedling. Can also be used. Further, it may be used by treating the soil for the purpose of controlling pests that inhabit the soil of the cultivated land. Moreover, it can also be used by the method of wrapping the resin formulation processed into the sheet form, the string form, etc. around the crop, stretching it around the crop, and / or laying it on the soil surface of the plant stock.

  Hereinafter, although the present invention will be described in more detail with formulation examples and test examples, the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified. First, formulation examples are shown.

Formulation Example 1 Emulsion (1: 1)
9 parts of the compound (I-1) to (I-5) or any of the compounds (II-1) to (II-3) and 9 parts of the compound (III) are mixed with 33.5 parts of xylene and dimethylformamide 33. Dissolve in 5 parts, add 10 parts of polyoxyethylene styryl phenyl ether and 5 parts of calcium dodecylbenzenesulfonate and mix well with stirring to obtain an emulsion.
Formulation Example 2 Wetting agent (1: 2)
3 parts of any one of compounds (I-1) to (I-5) or (II-1) to (II-3) and 6 parts of compound (III), 4 parts of sodium lauryl sulfate, and lignin sulfonic acid A mixture of 2 parts of calcium, 20 parts of synthetic hydrous silicon oxide fine powder and 65 parts of silicon earth is mixed and stirred well to obtain a wettable powder.

Formulation Example 3 Powder (8: 1)
4 parts of any of compounds (I-1) to (I-5) or compounds (II-1) to (II-3), 0.5 parts of compound (III), 1 part of synthetic silicon hydroxide-containing fine powder Then, 1 part of Doreles B (manufactured by Sankyo Co., Ltd.) as a flocculant and 7 parts of clay are mixed well in a mortar, and then stirred and mixed in a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed thoroughly with stirring to obtain a powder.
Formulation Example 4 Flowable Agent (4: 1)
Polyoxyethylene styryl phenyl ether sulfate salt 5 parts, 1% xanthan gum aqueous solution 20 parts, smectite mineral 3 parts and water 62 parts are uniformly dissolved, and compounds (I-1) to (I-5) or compound (II- Add 8 parts of the compound of any one of 1) to (II-3) and 2 parts of the compound (III), stir well, and wet pulverize with a sand mill to obtain a flowable agent.

Formulation Example 5 Microcapsule (2: 1)
6 parts of any one of compounds (I-1) to (I-5) or compounds (II-1) to (II-3), 3 parts of compound (III), 10 parts of phenylxylethane and Sumidur L- After mixing 0.5 parts of 75 (tolylene diisocyanate manufactured by Sumitomo Bayer Urethane Co., Ltd.), the mixture is added to 20 parts of a 10% aqueous solution of gum arabic and stirred with a homomixer to obtain an emulsion having an average particle size of 20 μm. Next, 2 parts of ethylene glycol is added thereto and further reacted in a warm bath at 60 ° C. for 24 hours to obtain a microcapsule slurry. On the other hand, 0.2 parts of Xanthan gum and 1 part of Bee gum R (aluminum magnesium silicate manufactured by Sanyo Chemical Co., Ltd.) are dispersed in 57.3 parts of ion-exchanged water to obtain a thickener solution.
42.5 parts of the microcapsule slurry and 57.5 parts of the thickener solution are mixed to obtain a 10% microcapsule.
Formulation Example 6 Oil (3: 1)
0.6 parts of any one of compounds (I-1) to (I-5) or compounds (II-1) to (II-3) and 0.2 parts of compound (III) are added to 5 parts of xylene and trichloroethane 5 And dissolved in 89.2 parts of deodorized kerosene to obtain a hot water.

Formulation Example 7 Granules (2: 1)
Compound (I-1) to (I-5) or Compound (II-1) to (II-3) 2 parts of compound, Compound (III) 1 part, Synthetic silicon hydroxide fine powder 5 parts, Dodecyl Add 5 parts of sodium benzenesulfonate, 30 parts of bentonite and 57 parts of clay, and mix well with stirring. Get a granule.

  Next, it is shown as a test example that the composition of the present invention is effective for pest control.

Test example 1
10 parts of compound (I-1) was dissolved in 40 parts of xylene and 40 parts of dimethylformamide, and 10 parts of Solpol 3005X (manufactured by Toho Chemical Industry Co., Ltd.) was added thereto and mixed well to prepare a preparation.
To a dilute solution obtained by adding a wettable powder of the compound (III) (trade name Chess wettable powder: manufactured by Syngenta Japan Co., Ltd.) to a predetermined concentration in an aqueous dilute solution of the compound (I-1) preparation A spreading agent for testing was prepared by adding a spreading agent (new Reno: manufactured by Nippon Agricultural Chemical Co., Ltd.) so that the amount of the spreading agent was 1/5000 in volume.
In addition, a predetermined concentration of water dilution of the preparation of compound (I-1) and a predetermined concentration of water dilution of compound (III) wettable powder (trade name Chess wettable powder: manufactured by Syngenta Japan Co., Ltd.) A spreading agent (new Reno: manufactured by Nippon Agricultural Chemicals Co., Ltd.) was added so that the amount of the spreading agent added was 1/5000 in volume to prepare a comparative spray solution for testing.
The active ingredient treatment concentration of each spray liquid is as shown below.

On the other hand, a cucumber was planted in a polyethylene cup and allowed to grow until the first true leaf developed, and about 20 cotton aphids were infested there. One day later, the spray solution was sprayed onto the cucumber at a rate of 20 ml / cup. Six days after spraying, the number of cotton aphids was investigated, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: number of insects before treatment in the untreated section Cai: number of insects at the time of observation of the untreated section Tb: number of insects before treatment of the treated section Tai: number of insects at the time of observation of the treated section As a result, the spray liquid 1 is Comparative spraying liquids 1 and 3 showed control values above that shown, and spraying liquid 2 showed comparative spraying liquids 2 and 4 or more.

Test Examples 2-8
Test Example 1 except that compounds (I-2) to (I-5), (II-1), (II-2a) and (II-3a) were used instead of compound (I-1) As a result of performing the same operation, in any of the compounds (I-2) to (I-5), (II-1), (II-2a) and (II-3a), the spray liquid 1 is Comparative spraying liquids 1 and 3 showed control values above that shown, and spraying liquid 2 showed comparative spraying liquids 2 and 4 or more.

Test Example 9
Except changing the concentration of compound (I-1) and compound (III) to the following Table 2, when the same operation as in Test Example 1 is performed, the spray liquid 1 shows a control value of almost 100%, comparative spray liquid 1 and 2 also show a control value of almost 100%.

In general, the control effect expected when two kinds of given active ingredient compounds are mixed and processed can be obtained by the Colby calculation formula shown by the following equation (1).

X: Control value (%) when active ingredient compound A is treated with m ppm
Y: Control value (%) when active ingredient compound B is treated with n ppm
E: Control value (%) expected when active ingredient compound A is treated with m ppm and B with n ppm (hereinafter referred to as expected value of control value)
In general, if the control value (%) actually mixed and processed is not smaller than the expected control value (%), it can be said that there is no antagonistic action in the combination and there is a mixed effect by spectrum complementation. As mentioned above, it can also confirm easily that the composition of this invention has the effect excellent in pest control by implementing the said test.

Test Examples 10 to 16
Similar to Test Example 9 except that compounds (I-2) to (I-5), (II-1), (II-2a) and (II-3a) are used instead of compound (I-1) In the case of performing the above operation, the spray liquid 1 is almost 100% in any of the compounds (I-2) to (I-5), (II-1), (II-2a) and (II-3a). The comparative control liquids 1 and 2 also show a control value of almost 100%.

The composition of the present invention exhibits excellent efficacy for controlling pests.

Claims (5)

(1) Formula (I)

[Wherein R ¹ represents a hydrogen atom or a C1-C4 alkyl group,
R ² represents a C3-C7 alkynyloxy group,
R ³ represents a hydrogen atom, a halogen atom or a C1-C3 alkyl group,
X represents a C4-C7 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group). ]
Or a pyrimidine compound represented by formula (II)

[Wherein R ¹ represents a C3-C7 alkynyl group,
A represents A ¹ or A ² below,

X ² represents a C4-C7 alkanediyl group or a C4-C7 alkenediyl group,
R ⁵ represents a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group,
R ⁶ represents a C1-C3 alkyl group,
l represents an integer of 0 to 4, and n represents an integer of 0 to 2.
when l is an integer of 2 or more, R ⁵ represents the same or different groups;
When n is 2, R ⁶ represents the same or different groups. ]
A 1,2,4-thiadiazole compound represented by:
(2) It contains (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one as an active ingredient. A pest control composition. The compound represented by formula (I) or formula (II) is any one of compounds (I-1) to (I-5), (II-1), (II-2a) and (II-3a) The pest control composition according to claim 1.

(1) Pyrimidine compound represented by formula (I) or 1,2,4-thiadiazole compound represented by formula (II) and (2) (E) -4,5-dihydro-6-methyl-4- (3- The pest control composition according to claim 1 or 2, wherein the weight ratio of pyridylmethyleneamino) -1,2,4-triazin-3 (2H) -one ranges from 200: 1 to 1:30.   A pest control method comprising applying the pest control composition according to any one of claims 1 to 3 to a pest or a habitat of the pest. (1) Formula (I)

[Wherein R ¹ represents a hydrogen atom or a C1-C4 alkyl group,
R ² represents a C3-C7 alkynyloxy group,
R ³ represents a hydrogen atom, a halogen atom or a C1-C3 alkyl group,
X represents a C4-C7 polymethylene group (which may be substituted with a halogen atom, a trifluoromethyl group and / or a C1-C4 alkyl group). ]
Or a pyrimidine compound represented by formula (II)

[Wherein R ¹ represents a C3-C7 alkynyl group,
A represents A ¹ or A ² below,

X ² represents a C4-C7 alkanediyl group or a C4-C7 alkenediyl group,
R ⁵ represents a halogen atom, a trifluoromethyl group or a C1-C4 alkyl group,
R ⁶ represents a C1-C3 alkyl group,
l represents an integer of 0 to 4, and n represents an integer of 0 to 2.
when l is an integer of 2 or more, R ⁵ represents the same or different groups;
When n is 2, R ⁶ represents the same or different groups. ]
And a 1,2,4-thiadiazole compound represented by (2) (E) -4,5-dihydro-6-methyl-4- (3-pyridylmethyleneamino) -1,2,4-triazine-3 (2H)- A method for controlling pests, which is characterized by applying ON to pests or habitats of pests.