JPH06247939A - Aminopyrimidine derivative, its production and test control agent - Google Patents

Abstract

PURPOSE:To obtain a novel aminopyrimidine derivative useful as a pest control agent having excellent effects such as insecticidal, acaricidal, bactericidal and nematicidal effects. CONSTITUTION:A compound of formula I (R<1> is halogen, OH, lower acyloxy, lower acylthio; R<2> is CF3, cycloalkyl; A is direct bond, lower alkylene), e.g. 6-(1-chloroethyl)-5-chloro-4-(2,2,2-trifluoroethylamino)pyrimidine. The compound is obtained by reacting a pyrimidine derivative of formula II (X is halogen) with an amine of formula III preferably in the presence of a base. Pests capable of being controlled with the compound include agricultural and horticultural insect pests (e.g. the order Hemiptera, Lepidoptera, or Acarina insect pests), sanitary insect pests (e.g. fly, mosquito), stored grain insect pests (e.g. Tribolium), Meloidogyne in soil, Bursaphelenchus xylophilus, and further agricultural and horticultural pathogenic fungi (e.g. rice blast, barley powdery mildew).

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel aminopyrimidine derivative useful as an insecticide, acaricide, fungicide, nematicide and the like.

[0002]

Description of the Prior Art Since the aminopyrimidine derivative of the present invention is a novel compound, it is not known to have its pest controlling activity.

[0003]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel aminopyrimidine derivative, a process for producing the same, and pest control useful as insecticides, acaricides, fungicides, nematicides, etc. containing the same as active ingredients. To provide the agent.

[0004]

Means for Solving the Problems As a result of studies to solve the above-mentioned problems, the present inventors have found that a novel aminopyrimidine derivative is useful as an insecticide, acaricide, fungicide, nematicide or the like. As a pest control agent, they have found to have remarkable control activity, and have completed the present invention.
That is, the present invention is as follows. The first invention is represented by the following formula (I):

[0005]

[Chemical 4]

(In the formula, R ¹ represents a halogen atom, a hydroxyl group, a lower acyloxy group or a lower acylthio group; R ² represents a trifluoromethyl or cycloalkyl group; A represents a direct bond or a lower alkylene group.) The present invention relates to an aminopyrimidine derivative represented by In the compound (I) of the present invention, the carbon atom marked with * and the carbon atom when A is a branched alkylene are asymmetric carbon atoms,
Any of the individual optical isomers, racemates, diastereomers or mixtures thereof are included in the present invention.
The second invention is the following formula (II):

[0007]

[Chemical 5]

(Wherein R ¹ has the same meaning as described above;
X represents a halogen atom. ) And the following formula (III):

[0009]

[Chemical 6]

A method for producing an aminopyrimidine derivative represented by the above formula (I), which comprises reacting with an amine represented by the formula (wherein R ² and A have the same meanings as described above). It is about.

A third invention relates to a pest control agent containing an aminopyrimidine derivative represented by the above-mentioned formula (I) as an active ingredient.

The present invention will be described in detail below. The novel aminopyrimidine derivative (I) [comprising compounds (I-1) to (I-4)] which is the above-mentioned target compound, and R ¹ and R ² in the compounds (II) to (VIII) which are raw materials for the production thereof , R
³ , R ⁴ , A, M and X are as follows.

Examples of R ¹ include a halogen atom, a hydroxyl group, a lower acyloxy group and a lower acylthio group. Examples of the halogen atom in R ¹ include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; preferably a chlorine atom and a fluorine atom.

The lower acyloxy group for R ¹ has a total of 2 to 9 carbon atoms having a linear or branched alkyl group (for example, acetyloxy group, propionyloxy group, n-butyroyloxy group, i -Butyroyloxy group, n-pentanoyloxy group, n-hexanoyloxy group, etc.), those having a cycloalkyl group and a total of 4 to 9 carbon atoms (for example, cyclopropanecarbonyloxy group, cyclopentanecarbonyloxy group, etc.) ) And the like; preferably those having a total of 2 to 5 carbon atoms having a linear or branched alkyl group, and those having a total of 4 to 7 carbon atoms having a cycloalkyl group. More preferably, an acetyloxy group, a propionyloxy group and the like can be mentioned.

The lower acylthio group for R ¹ is
Total number of carbon atoms having a linear or branched alkyl group 2
Up to 5 groups (for example, acetylthio group, propionylthio group, n-butyroylthio group, i-butyroylthio group, etc.) can be mentioned; preferably, acetylthio group is preferable. Examples of R ² include a trifluoromethyl group and a cycloalkyl group.

The cycloalkyl group for R ² is
Examples thereof include those having 3 to 10 carbon atoms (for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc.); preferably those having 3 to 8 carbon atoms; Preferably, it has 3 to 6 carbon atoms (eg, cyclopropyl group, cyclohexyl group, etc.).

Examples of A include a direct bond and a lower alkylene group. Examples of the lower alkylene group for A include linear or branched ones having 1 to 6 carbon atoms; preferably those having 1 to 4 carbon atoms; more preferably Having 1 to 3 carbon atoms (for example, methylene, ethylene, n-
Propylene, i-propylene, etc.) are preferable.

R ³ and X are halogen atoms (eg R
¹ and the like described above). R ⁴ is R
^{It represents} a lower acyloxy group (lower aliphatic carboxylic acid residue), a lower acylthio group (lower fatty acid thiocarboxylic acid residue), etc. corresponding to ¹ . M represents an alkali metal.

As can be understood from the compound (I) of the present invention, since the compound (I) has an amino group and can easily form an acid addition salt, such a salt is also included in the present invention. Included in the invention. Examples of acids that form acid addition salts include inorganic acids (hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.), carboxylic acids (formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid). , Aconitic acid, etc.), organic sulfonic acid (methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc.), saccharin and the like.

As a preferred embodiment for producing the aminopyrimidine derivative represented by the above formula (I),
In addition to the synthesis method 1 described as the second invention, the following four types of production methods (synthesis methods 2 to 5) can be mentioned. [Synthesis Method 2] The following formula (I-1):

[0021]

[Chemical 7]

(Wherein R ² and A have the same meanings as described above; R ³ represents a halogen atom) and an aminopyrimidine derivative represented by the following formula (IV):

[0023]

[Chemical 8]

(In the formula, R ⁴ represents a lower acyloxy group or a lower acylthio group.) In the above formula (I), R ¹ is lower The present invention relates to a method for producing an aminopyrimidine derivative represented by an acyloxy group or a lower acylthio group. [Synthesis Method 3] The following formula (I-2):

[0025]

[Chemical 9]

(In the formula, R ² , R ⁴ and A have the same meanings as described above.) And an aminopyrimidine derivative represented by the following formula (V):

[0027]

[Chemical 10]

A method for producing an aminopyrimidine derivative represented by the above formula (I), wherein R ¹ is a hydroxyl group, characterized by reacting with an inorganic base represented by the formula (wherein M represents an alkali metal). It is about. [Synthesis Method 4] The following formula (I-3):

[0029]

[Chemical 11]

(Wherein R ² and A have the same meanings as described above), and the aminopyrimidine derivative represented by the formula (I) is reacted with the fluorinating agent.
In R ¹ relates to a method for producing an aminopyrimidine derivative represented by a fluorine atom. [Synthesis Method 5] An aminopyrimidine derivative represented by the above formula (I-1) and the following formula (VI):

[0031]

[Chemical 12]

(In the formula, M has the same meaning as described above.)
The present invention relates to a method for producing an aminopyrimidine derivative represented by the above formula (I), wherein R ¹ is a fluorine atom, which is characterized by reacting with a fluorine compound represented by

The synthesis of the compound (I) of the present invention will be described in more detail by the following synthetic methods 1 to 5. (Synthesis Method 1) As shown below, the synthesis of the compound (I) of the present invention is usually carried out by reacting the starting compound (II) with the compound (III) in a solvent or without a solvent. However, it is preferable to react in the presence of a base in order to accelerate the reaction.

[0034]

[Chemical 13]

(In the formula, R ¹ , R ² , A and X have the same meanings as described above.) The solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, benzene,
Chlorinated or non-chlorinated aromatics, such as toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, cyclohexane, aliphatic , Alicyclic hydrocarbons; ethers such as diethyl ether, tetrahydrofuran, dioxane; ketones such as acetone, methyl ethyl ketone; alcohols such as methanol, ethanol, n-propanol, i-propanol; N , N-dimethylformamide, N, N-dimethylacetamide and the like amides; acetonitrile, propionitrile and the like nitriles; triethylamine, pyridine, N, N-
Organic bases such as dimethylaniline; 1,3-dimethyl-2-imidazolidinone; dimethyl sulfoxide;
Examples thereof include a mixture of the above solvents.

The amount of the solvent used is the compound (I
The compound (II) can be used in a concentration range of 5 to 80% by weight, and preferably the compound (II) is used in a concentration of 10 to 70% by weight.

The base is not particularly limited and includes, for example,
Organic bases (eg triethylamine, pyridine, N,
N-dimethylaniline, DBU, etc., alkali metal alkoxides (eg, sodium methoxide, sodium ethoxide, etc.), inorganic bases (eg, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, hydrogen carbonate) Sodium, potassium carbonate, etc.); but organic bases are preferred.

The amount of the base used is the compound (I
It can be used in an amount of 0.001 to 5 times the molar amount of I), but preferably 0.8 to 5 times the molar amount.
The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used or less, and preferably 80 to 110 ° C. Further, if the amine used has a low boiling point, it is preferable to react in a sealed tube (autoclave).

The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 0.3 to 2 hours. The amount of the raw material compound used is the amount of the compound (II
I) is 0.5 to 2 times mol, but preferably 0.8 to
It is preferably 1.5 times the molar amount.

The compound (II) used in the present invention (when R ¹ = X) is usually the starting compound (VII-
It can be produced by reacting 1) with compound (VIII-1) in a solvent.

[0041]

[Chemical 14]

(In the formula, when R ¹ = X, X has the same meaning as described above.) Examples of the solvent include those described above; It can be used such that the concentration of () is in the concentration range of 5 to 80% by weight. The reaction temperature is not particularly limited, but it can be carried out within a temperature range from room temperature to the boiling point of the solvent used or less. The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 2 to 10 hours.

The amount of the raw material compound used is 0.5 to 3 times mol, preferably 0.5 to 1.7 times mol of the compound (VIII-1) with respect to the compound (VII-1). Is good. Compound
(VII-3) is, for example, Journal of Chemical Society (JCS) 3478-3481 (195).
According to the method described in 5 years), it can be produced by carrying out as shown in the following formula.

[0044]

[Chemical 15]

(Wherein X has the same meaning as described above; R
Is optionally a lower alkyl group, hydrogen atom, hydroxyl group or halogen atom. ) The target compound (II) produced as described above is extracted, concentrated,
Perform normal post-treatment such as filtration, recrystallize if necessary,
It can be appropriately purified by a known means such as various chromatography. Examples of the compound (II) are shown in Table 1.
The compounds (II-1) to (II-7) shown therein can be mentioned.

The compound (III) used in the present invention is, for example,
J. Am. Chem. Soc. 72, 2786 (1950) or Org. Syn. Coll. , 2
In accordance with the method described in Vol., 318, it can be manufactured by carrying out as shown in the following formula.

[0047]

[Chemical 16]

(In the formula, R ² , A and X have the same meanings as described above; R ⁵ represents a hydrogen atom or a methyl group; A ′ represents a methylene group.) Examples of the compound (III) include: ,
Compounds (III) [compounds (III) ₁ to (I
II) _{Called 32} . For example, compound (III) ₁
In the formula represented by II), R ² is a trifluoromethyl group and A is a methylene group. ] Can be mentioned.

Examples of the compound (I) are shown in Tables 2-5.
Compounds 1 to 32 shown therein can be mentioned [Compound 1 is a compound represented by the formula (I) in which R ¹ is a chlorine atom, R ² is a trifluoromethyl group, and A is a methylene group. ].

(Synthesis Method 2) Compound (I-2) [Compound (I)
[Wherein R ¹ is a lower acyloxy group in] can be usually synthesized by reacting compound (I-1) with compound (IV) in a solvent or without a solvent, but the reaction is accelerated. Therefore, it is preferable to react in the presence of a base.

[0051]

[Chemical 17]

(In the formula, R ² , R ³ , R ⁴ and A have the same meanings as described above.) As the solvent, in addition to the solvent described in Synthesis Method 1, acetic acid, propionic acid or the like can be used. Aliphatic carboxylic acids, mixtures thereof, etc. can be mentioned;
The same aliphatic carboxylic acid as the N, N-dimethylformamide and the acyloxy group to be introduced is preferable.

The amount of the solvent used is the compound (I-
The compound (1) can be used in a concentration range of 5 to 80% by weight, but it is preferable to use the compound (I-1) in a concentration of 10 to 70% by weight. Good. Examples of the base include the bases described in Synthesis Method 1; inorganic bases are preferred.

The amount of the base used is the compound (I-
It can be used in a 1- to 5-fold molar quantity relative to 1),
It is preferably 2 to 5 times the molar amount. The reaction temperature is
Although not particularly limited, it is within a temperature range from room temperature to the boiling point of the solvent used or less, and preferably 80 to 120 ° C.

The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 10 to 50 hours. As the compound (IV), a commercially available product can be used. The desired compound (I-2) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after completion of the reaction, and if necessary, known crystals such as recrystallization and various chromatographies are used. It can be appropriately purified by means.

Examples of the compound (I-2) are shown in Tables 2 to 5
Compounds 3,7,10,14,18,22,2 shown in
It consists of each substituent type corresponding to 6, 27, 28, etc.
Compound (I-2) [Compound (I-2)₃， (I-2)₇， (I-2)_Ten，
(I-2)₁₄， (I-2)₁₈， (I-2) _{twenty two}， (I-2)₂₆， (I-2)₂₇，
(I-2)₂₈And so on. For example, compound (I-2)₃Is a compound
R in the formula represented by the formula (I)¹(To compound (I-2)
K R^Five) Is an acetyloxy group, R²Is trifluorome
A chill group and A is a methylene group. ]
It

(Synthesis Method 3) Compound (I-3) [Compound (I)
[Wherein R ¹ is a hydroxyl group]
It can be carried out by reacting compound (I-2) with compound (V) in the presence of a base in a solvent.

[0058]

[Chemical 18]

(In the formula, R ² , R ⁴ , A and M have the same meanings as described above.) As the solvent, in addition to the ethers, ketones, amides described in Synthesis Method 1, alcohols (For example, methanol, ethanol, propanol, butanol, etc.), water, and a mixture of the above solvents can be mentioned; preferably, a mixture of alcohols and water is preferable. The amount of the solvent used may be such that the concentration of the compound (I-2) is in the range of 5 to 80% by weight, but the concentration of the compound (I-2) is preferably 10. It is advisable to use it in an amount of up to 70% by weight.

Examples of the base include the inorganic bases described in Synthesis Method 1; sodium hydroxide and potassium hydroxide are preferred. The amount of the base used can be 1 to 5 times mol, preferably 2 to 5 times mol, of the compound (I-2).

The reaction temperature is not particularly limited, but it is within the temperature range from room temperature to the boiling point of the solvent used, and
50 ° C is preferred. The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 0.5 to 1 hour.

As the compound (V), commercially available products can be used. The target compound (I-
After the reaction, 3) is subjected to usual post-treatments such as extraction, concentration and filtration, and can be appropriately purified by known means such as recrystallization and various chromatographies if necessary.

Examples of the compound (I-3) are shown in Tables 2-5.
Compounds shown in 4,8,11,15,19,23,2
Each compound (I-
3) [Compound (I-3) ₄ , (I-3) ₈ , (I-3) ₁₁ , (I-3) ₁₅ ,, (I
-3) ₁₉ , (I-3) ₂₃ , (I-3) _29, etc. For example, the compound (I-3) ₄ is represented by R ^{1 in the} formula represented by the compound (I).
Is a hydroxyl group, R ² is a trifluoromethyl group, and A is a methylene group. ] Can be mentioned.

(Synthesis Method 4) Compound (I-4) [Compound (I)
[Wherein R ¹ is a fluorine atom] can be usually synthesized by reacting the compound (I-3) with a fluorinating agent in a solvent or without a solvent.

[0065]

[Chemical 19]

(In the formula, R ² and A have the same meanings as described above.) As the solvent, the chlorinated or non-chlorinated aromatic, aliphatic or alicyclic carbon as described in Synthesis Method 1 is used. Mention may be made of hydrogens, ethers, and mixtures of the solvents mentioned.

The amount of the solvent used is the compound (I-
The compound (3) can be used in a concentration range of 5 to 80% by weight, but it is preferable to use the compound (I-3) in a concentration of 10 to 70% by weight. Good. Examples of the fluorinating agent include alkylaminosulfur fluorinated compounds, for example, the following formulas;

[0068]

[Chemical 20]

Diethylaminosulfur trifluoride (DAST) represented by can be used. And, the amount used is 1 to the compound (I-3).
Although it can be used in a 5-fold molar amount, it is preferably in a 1- to 2-fold molar amount.

The reaction temperature is not particularly limited, but it is within the temperature range from the ice cooling temperature to the boiling point of the solvent used or less, and ice cooling to room temperature is preferable. The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.3 to 2 hours.

(Synthesis Method 5) Compound (I-4) [Compound (I)
[Wherein R ¹ is a fluorine atom in] is synthesized by reacting compound (I-1) with compound (VI) [fluorine compound] in a solvent or in the absence of solvent, in addition to the synthesis method 4. Can also be done.

[0072]

[Chemical 21]

(In the formula, R ² , R ³ , A and M have the same meanings as described above.) As the solvent, amides such as N, N-dimethylformamide and N, N-dimethylacetamide; 1 , 3-dimethyl-2-imidazoline; dimethyl sulfoxide; sulfolane; a mixture of the above solvents, and the like.

The amount of the solvent used is the compound (I-
The compound (1) can be used in a concentration range of 5 to 80% by weight, but it is preferable to use the compound (I-1) in a concentration of 10 to 70% by weight. Good. Examples of the compound (VI) include alkali metal fluorine compounds, preferably cesium fluoride,
Potassium fluoride is good.

The amount of the compound (I-1) used can be 1 to 5 times mol, but preferably 1.2 to 3 times mol to the compound (I-1). It should be The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used, or 100 to 140.
C is preferred.

The reaction time varies depending on the above-mentioned concentration and temperature, but it is usually 1 to 8 hours. After completion of the reaction, the target compound (I-4) produced by the synthetic methods 4 and 5 is subjected to usual post-treatments such as extraction, concentration and filtration, and if necessary, recrystallization, various chromatographies and the like known methods. It can be appropriately purified by the above method.

Examples of the compound (I-4) are shown in Tables 2-5.
Compounds 2,6,12,16,20,24,3 shown in
Compound (I-4) [compound (I-4) ₂ , (I-4) ₆ , (I-4) ₁₂ , (I-4) consisting of each substituent type corresponding to 0, 32, etc.
₁₆ , (I-4) ₂₀ , (I-4) ₂₄ , (I-4) ₃₀ , (I-4) _32, etc. For example, the compound (I-4) ₂ is a compound represented by the formula (I) wherein R ¹ is a fluorine atom, R ² is a trifluoromethyl group, and A is a methylene group. ] Can be mentioned.

The pests which can be controlled by the compound (I) of the present invention include agricultural and horticultural pests [eg, Hemiptera (Plants, leafhoppers, aphids, whiteflies, etc.), Lepidoptera (Beetle beetles). , Plutella xylostella, Pseudococcidae, Beetle moth, Singing beetle, Pieris rapae, Coleoptera (Galloridae, Weevil, Chrysomelidae, Scarabaeidae, etc.) )], Sanitary pests (for example, flies, mosquitoes, cockroaches, etc.), stored-grain pests (Beetle beetles, bean weevils, etc.), root-knot nematodes, pine wood nematodes, and ticks, and agro-horticultural pathogens ( For example, wheat leaf rust, barley powdery mildew, cucumber downy mildew, rice blast, toma Epidemics, etc.) can be mentioned.

The pest control agent of the present invention is a prominent insecticide.
It has acaricidal, bactericidal and nematicidal effects and contains one or more compounds (I) as active ingredients. Compound (I) can be used alone,
Usually, a carrier, a surfactant, a dispersant, an auxiliary agent, etc. are prepared by a conventional method (eg, a powder, an emulsion, a fine granule, a granule, a wettable powder, an oily suspension, a composition such as an aerosol). It is preferable to use.

Examples of the carrier include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonization. Hydrogen (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene) Liquid carriers such as glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection), and the like.

Examples of surfactants and dispersants that can be used to improve the performance of this agent, such as adhesion to animals and plants, absorption, dispersion of the drug, emulsification, spreading, and the like, include alcohol sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic or the like can be used as an auxiliary agent.

In the preparation of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in suitable combination according to the purpose.
The concentration of the active ingredient when the compound (I) of the present invention is formulated is usually 1 to 50% by weight in the case of emulsion and 0.3 in the case of powder.
25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, usually 0.1 to 5% by weight for aerosols. is there. These formulations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, water surface of paddy field or directly applied to various applications depending on the purpose.

[0083]

EXAMPLES The present invention will be specifically described below with reference to examples and examples. It should be noted that these examples do not limit the scope of the present invention. Reference Example 1 [Synthesis of Compound (II)] (1) Synthesis of 6- (1-chloroethyl) -4,5-dichloropyrimidine [Compound (II-1)] 4,5-Dichloro-6-ethylpyrimidine (270 g )
Dissolved in dichloromethane (750 ml), 30-35
Chlorine gas was blown in for 2 hours while being heated to ℃ and stirred. Nitrogen gas was blown into the reaction solution to remove dissolved excess chlorine gas. Then, the solvent was distilled off under reduced pressure, and the obtained residue was distilled under reduced pressure to obtain 240 g of a target product which was a pale yellow liquid.

(2) Synthesis of 4,5-dichloro-6- (1-fluoroethyl) pyrimidine [compound (II-4)] 6- (1-hydroxyethyl) -4,5-dichloropyrimidine (2.1 g Was dissolved in dichloromethane (15 ml), diethylaminosulfur trifluoride (2.0 g) was added dropwise with ice cooling and stirring, and the reaction was completed by stirring at room temperature for 1 hour. Cold water (20 ml) was added to the reaction solution, the dichloromethane layer was separated, washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure,
The obtained residue was purified by column chromatography (Wakogel C-200, eluted with chloroform) to obtain 1.3 g of the target product as a pale yellow oily liquid.

(Physical properties) b. p. ^{229~231 ℃ · 1 H-NMR (} CDCl 3, δppm) 1.64~1.81 (d-d, 3H), 5.84~6.
19 (dq, 1H), 8.92 (s, 1H)

(3) 5-chloro-4-fluoro-6- (1
Synthesis of -Fluoroethyl) pyrimidine [Compound (II-5)] 4,5-Dichloro-6- (1-fluoroethyl) pyrimidine (1.3 g) was mixed with N, N-dimethylformamide (1
0 ml) and dissolved in cesium fluoride (4.0 g)
Was added and stirred at room temperature for 1 hour and a half to complete the reaction. Cold water (10 ml) was added to the reaction solution, and the oily substance that separated was extracted with toluene, washed with water, and then dried over anhydrous sodium sulfate.
Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (Wakogel C-200, eluted with chloroform) to obtain 1.0 g of the desired product as a pale yellow oily liquid.

(Physical properties) b. p. 192-194 ° C ¹ H-NMR (CDCl ₃ , δppm) 1.66-1.82 (d-d, 3H), 5.85-6.
21 (dq, 1H), 8.83 (s, 1H)

(4) 6- (1-acetoxyethyl) -4,
Synthesis of 5-dichloropyrimidine [Compound (II-6)] 6- (1-chloroethyl) -4,5-dichloropyrimidine (10.2 g) was added to N, N-dimethylformamide (1
50 ml), potassium acetate (12.0 g) and potassium carbonate (3.0 g) were added, and the mixture was stirred at about 60 ° C. for 3 hours. Water (200 ml) was added to the reaction solution, and the separated oily substance was extracted with toluene, washed with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained residue was subjected to column chromatography (Wako Gel C-20
0, toluene: ethyl acetate = 10: 1 elution) to obtain 5.2 g of the desired product as a pale yellow liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.55 to 1.62 (d, 3H), 2.15 (s, 3)
H), 6.00 to 6.12 (q, 1H), 8.84
(S, 1H)

(5) Synthesis of 4,5-dichloro-6- (1-hydroxyethyl) pyrimidine [Compound (II-7)] 6- (1-acetoxyethyl) -4,5-dichloropyrimidine (4.0 g) ) To tetrahydrofuran (50 ml)
And 1N-sodium hydroxide aqueous solution (3
0 ml) was slowly added dropwise. After the dropping, the reaction was completed by further stirring for 1 hour at room temperature. Then, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 5: 1) to obtain 2.8 g of the desired product as a pale yellow liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.47 to 1.52 (d, 3H), 3.76 to 3.85
(D, 1H), 5.17 to 5.25 (m, 1H), 8.
88 (s, 1H) (6) Compound (II) was synthesized by the same method as in (1) to (5) above.

[0092]

[Table 1]

Example 1 [Synthesis of Compound (I)] The target compound (I) was synthesized using the compound (II) obtained in Reference Example 1. (1) 5-chloro-6- (1-chloroethyl) -4-
Synthesis of (2,2,2-trifluoroethylamino) pyrimidine (Compound 1) 2,2,2-trifluoroethylamine (3.0 g) and triethylamine (3.5 g) were combined with ethanol (30 m).
l) and 6- (1-chloroethyl)-
100 ml of 4,5-dichloropyrimidine (6.3 g)
It was charged in an autoclave and heated at 90 to 95 ° C. for 4 hours for reaction. After the reaction was completed, ethanol was distilled off under reduced pressure,
Water was added, the desired product was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) and then recrystallized from n-hexane to give the desired product as colorless plate crystals. 5.4 g was obtained.

(2) 5-chloro-6- (1-fluoroethyl) -4- (2,2,2-trifluoroethylamino)
Synthesis of pyrimidine (Compound 2) 5-chloro-6- (1-chloroethyl) -4- (2,
2,2-trifluoroethylamino) pyrimidine (1.
4 g) to N, N-dimethylformamide (DMF) (2
0 ml), cesium fluoride (1.4 g) was added, and the mixture was stirred at 100 to 120 ° C. for 6 hours. After the reaction was completed, water was added and the desired product was extracted with toluene. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by column chromatography (Wakogel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 0.4 g of the desired product as colorless powdery crystals.

(3) 6- (1-acetoxyethyl) -5-
Synthesis of Chloro-4- (2,2,2-trifluoroethylamino) pyrimidine (Compound 3) 5-Chloro-6- (1-chloroethyl) -4- (2,
2,2-trifluoroethylamino) pyrimidine (2.
7 g) was dissolved in DMF (30 ml), potassium acetate (1.6 g) and potassium carbonate (1.2 g) were added, and the mixture was stirred at 60 ° C. for 4 hr. After completion of the reaction, add water,
Then, the target substance was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
(8: 2 elution) to obtain 2.2 g of the desired product as colorless powdery crystals.

(4) Synthesis of 5-chloro-6- (1-hydroxyethyl) -4- (2,2,2-trifluoroethylamino) pyrimidine (Compound 4) 6- (1-acetoxyethyl) -5 -Chloro-4-
(2,2,2-Trifluoroethylamino) pyrimidine (2.0 g) was dissolved in a 1: 1 mixture (20 ml) of ethanol and 10% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-200, toluene: ethyl acetate = 8:
(1 elution) to obtain 1.6 g of the desired product as colorless powdery crystals.

(5) Synthesis of 5-chloro-6- (1-fluoroethyl) -4- (3,3,3-trifluoropropylamino) pyrimidine (Compound 6) 3,3,3-trifluoropropylamine (1.2g)
And triethylamine (2.5 g) with ethanol (30 m
l) and 6- (1-fluoroethyl)-
100 ml of 4,5-dichloropyrimidine (1.0 g)
The mixture was placed in an autoclave and stirred at 90 to 95 ° C for 4 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, water was added, and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, eluted with toluene) to obtain 0.6 g of the desired product as colorless powdery crystals.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.55 to 1.76 (multi, 5H), 4.00
4.12 (multi, 2H), 5.72 to 6.08
(Q-d, 1H), 6.62 to 6.76 (multi,
1H), 8.61 (s, 1H)

(6) 5-chloro-6- (1-chloroethyl) -4- (2-trifluoromethylpropylamino)
Synthesis of Pyrimidine (Compound 9) 2-Trifluoromethylpropylamine (1.5 g) and triethylamine (5.0 g) were combined with ethanol (30 m).
l) and 6- (1-chloroethyl)-
100 ml of 4,5-dichloropyrimidine (1.0 g)
It was charged in an autoclave and heated at 90 to 95 ° C. for 4 hours for reaction. After the reaction was completed, ethanol was distilled off under reduced pressure,
Water was added and the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was isolated by column chromatography (Wakogel C-200, eluted with toluene) to give 1.9 as a colorless oily liquid.
g was obtained.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.15 to 1.20 (d, 3H), 1.80 to 1.86
(D, 3H), 2.52 to 2.76 (multi, 1
H), 3.65 to 3.80 (multi, 2H), 5.
35 to 5.45 (q, 1H), 5.62 to 5.80 (b
road, 2H), 8.52 (s, 1H)

(7) 6- (1-acetoxyethyl) -5-
Synthesis of Chloro-4- (2-trifluoromethylpropylamino) pyrimidine (Compound 10) 5-Chloro-4- (2-trifluoromethylpropylamino) pyrimidine (1.8 g) was dissolved in DMF (20 ml), Then, potassium acetate (2.6 g) and potassium carbonate (2.0 g) were added, and the mixture was stirred at 60 ° C. for 4 hours.
After the reaction was completed, water was added, and then the target product was extracted with toluene. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by column chromatography (Wakogel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 1.8 g of the desired product as colorless powdery crystals.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.22 (d, 3H), 1.52 to 1.60
(Multi, 3H), 2.15 (s, 3H), 2.5
5 to 2.80 (multi, 1H), 3.58 to 3.8
5 (multi, 2H), 5.60 to 5.75 (bro
ad, 1H), 5.98 to 6.08 (q, 1H), 8.
50 (s, 1H)

(8) Synthesis of 5-chloro-6- (1-hydroxyethyl) -4- (2-trifluoromethylpropylamino) pyrimidine (Compound 11) 6- (1-acetoxyethyl) -5-chloro- 4- (2
-Trifluoromethylpropylamino) pyrimidine (1.8 g) was dissolved in a 1: 1 mixture (30 ml) of ethanol and 10% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ethanol was distilled off under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily matter was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate = 9:
(1 elution) to obtain 1.3 g of the desired product as colorless powdery crystals.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.22 (d, 3H), 1.40 to 1.44
(D, 3H), 2.52 to 2.76 (multi, 1
H), 3.64 to 3.82 (multi, 2H), 4.
08-4.12 (d, 1H), 4.92-5.08 (m
ulti, 1H), 5.58 to 5.72 (broad,
1H), 8.49 (s, 1H)

(9) 5-chloro-6- (1-fluoroethyl) -4- (2-trifluoromethylpropylamino)
Synthesis of pyrimidine (Compound 12) 6- (1-hydroxyethyl) -5-chloro-4- (2
-Trifluoromethylpropylamino) pyrimidine (1.0 g) dissolved in dichloromethane (30 ml),
Diethylaminosulfur trifluoride (0.9 g) was added dropwise with ice cooling and stirring, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water (20 ml) was added dropwise and the dichloromethane layer was separated. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-20
0, toluene: ethyl acetate = 20: 1 elution) to obtain 0.85 g of the target substance as colorless powdery crystals.
Obtained.

(Physical Properties) ¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.22 (d, 3H), 1.60 to 1.76
(D-d, 3H), 2.52 to 2.78 (multi,
1H), 3.62 to 3.86 (multi, 2H),
5.64 to 6.08 (multi, 2H), 8.57
(S, 1H)

(10) 6- (1-acetoxyethyl) -5
Synthesis of -Chloro-4- (cyclopropylmethylamino) pyrimidine (Compound 18) Cyclopropylmethylamine hydrochloride (1.1 g) and triethylamine (2.2 g) were dissolved in toluene (30 ml) and then with stirring. 6- (1-acetoxyethyl)
Add 4,5-dichloropyrimidine (2.4 g) and add 5
Heated to reflux for hours. After completion of the reaction, water was added, and then the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oil was purified by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 2.5 g of the desired product as a colorless oily liquid.

(11) Synthesis of 5-chloro-6- (1-hydroxyethyl) -4- (cyclopropylmethylamino) pyrimidine (Compound 19) Cyclopropylmethylamine hydrochloride (1.1 g) and triethylamine (2. 2 g) was dissolved in toluene (30 ml), 4,5-dichloro-6- (1-hydroxyethyl) pyrimidine (2.0 g) was added with stirring, and the mixture was heated under reflux for 5 hr. After completion of the reaction, water was added, and then the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C
-200, toluene: ethyl acetate = 9: 1 elution) to give 2.0 as a colorless oily liquid.
g was obtained.

(12) Synthesis of 5-chloro-6- (1-fluoroethyl) -4- (cyclopropylmethylamino) pyrimidine (Compound 20) Cyclopropylmethylamine hydrochloride (1.1 g) and triethylamine (2. 2 g) was dissolved in toluene (30 ml), 4,5-dichloro-6- (1-fluoroethyl) pyrimidine (2.0 g) was added with stirring, and the mixture was heated under reflux for 5 hr. After completion of the reaction, water was added, and then the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C-
200, toluene: ethyl acetate = 9: 1 elution) to isolate 2.1 g of the desired product as a colorless oily liquid.
Obtained.

(13) Synthesis of 5-chloro-6- (1-chloroethyl) -4- (1-cyclopropylethylamino) pyrimidine (Compound 21) 1-Cyclopropylethylamine hydrochloride (4.5 g) and triethylamine ( 10.0g) to ethanol (30m
l-) was dissolved in 6- (1-chloroethyl)-
Add 4,5-dichloropyrimidine (10.0 g) and add 6
The mixture was heated and stirred at 0 to 65 ° C for 4 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, water was added, and then the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C
(-200, eluted with toluene) to obtain 5.2 g of the desired product as a colorless oily liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 0.25 to 0.45 (multi, 2H), 0.45
0.65 (multi, 2H), 0.90 to 1.02
(Multi, 1H), 1.15 to 1.35 (multi
i, 3H), 1.80 to 1.85 (d, 1H), 3.6
0 to 3.70 (q, 2H), 5.38 to 5.45 (q,
1H), 5.45 to 5.58 (multi, 2H),
8.48 (s, 1H)

(14) 6- (1-acetoxyethyl) -5-
Synthesis of Chloro-4- (1-cyclopropylethylamino) pyrimidine (Compound 22) 5-Chloro-6- (1-chloroethyl) -4- (1-cyclopropylethylamino) pyrimidine (3.1 g) was added to DMF ( 30 ml), then potassium acetate (10.0 g) and potassium carbonate (3.0 g) were added, 6
The mixture was stirred at 0 ° C for 10 hours. After the reaction was completed, water was added, and then the target product was extracted with toluene. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily matter was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate = 9:
(1 elution) to obtain 2.5 g of the desired product as a colorless oily liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 0.25 to 0.45 (multi, 2H), 0.45
0.65 (multi, 2H), 0.90 to 1.02
(Multi, 1H), 1.20 to 1.35 (multi
i, 3H), 1.52 to 1.56 (d, 1H), 2.1
2 (s, 3H), 3.35 to 3.75 (multi, 1
H), 5.42 to 5.58 (d, 2H), 6.00
6.10 (q, 1H), 8.48 (s, 1H)

(15) Synthesis of 5-chloro-6- (1-hydroxyethyl) -4- (1-cyclopropylethylamino) pyrimidine (Compound 23) 6- (1-acetoxyethyl) -5-chloro-4 -(1
-Cyclopropylethylamino) pyrimidine (2.5
g) was dissolved in a 1: 1 mixture (30 ml) of ethanol and a 10% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ethanol was distilled off under reduced pressure, and the target product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oil was purified by column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 2.0 g of a target substance as a colorless oily liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 0.25 to 0.45 (multi, 2H), 0.45
0.65 (multi, 2H), 0.85 to 1.05
(Multi, 1H), 1.25 to 1.35 (dd,
3H), 1.42 to 1.48 (d, 3H), 3.60 to
3.78 (multi, 1H), 4.00 to 4.50
(Broad, 1H), 4.95 to 5.05 (q, 2
H), 5.42 to 5.60 (d, 1H), 8.42
(S, 1H)

(16) Synthesis of 5-chloro-6- (1-fluoroethyl) -4- (1-cyclopropylethylamino) pyrimidine (Compound 24) 5-chloro-6- (1-hydroxyethyl) -4 -(1
-Cyclopropylethylamino) pyrimidine (1.9
g) was dissolved in dichloromethane (30 ml), diethylaminosulfur trifluoride (1.5 g) was added dropwise under ice-cooling and stirring, and the mixture was stirred at room temperature for 1 hr. After completion of the reaction, water (20 ml) was added dropwise and the dichloromethane layer was separated. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by column chromatography (Wakogel C-200, toluene: ethyl acetate = 20: 1 elution) to obtain 0.90 g of the desired product as a colorless oily liquid.

(Physical properties) ¹ H-NMR (CDCl ₃ , δppm) 0.25 to 0.45 (multi, 2H), 0.45
0.65 (multi, 2H), 0.88 to 1.00
(Multi, 1H), 1.30 to 1.35 (d, 3
H), 1.60 to 1.72 (dd, 3H), 3.62
~ 3.78 (multi, 1H), 5.45-5.58
(D, 1H), 5.78 to 6.06 (q, 2H), 8.
50 (s, 1H)

(17) 6- (1-acetylthioethyl)-
Synthesis of 5-chloro-4- (cyclohexylmethylamino) pyrimidine (Compound 27) 5-Chloro-6- (1-chloroethyl) -4- (cyclohexylmethylamino) pyrimidine (1.4 g) in DM
Dissolve in F (20 ml), then thioacetic acid (0.5
g) and potassium carbonate (0.6 g) were added, and the mixture was stirred at 60 ° C for 6 hr. After completion of the reaction, water was added, and then the desired product was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to column chromatography (Wako Gel C
-200, toluene: ethyl acetate = 4: 1 elution) to obtain 1.0 g of the desired product as a pale yellow red oily liquid.

(18) Synthesis of Other Target Compound (I) in Tables 2-5 According to the method described in (1) to (17) above, other target compound (I) in Tables 2-5 Was synthesized. The compounds synthesized as described above are shown in Tables 2-5.

[0120]

[Table 2]

[0121]

[Table 3]

[0122]

[Table 4]

[0123]

[Table 5]

Example 2 [Preparation of preparation] (1) Preparation of granules 5 parts by weight of compound 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of neoperex powder (trade name; manufactured by Kao Corporation) And 2 parts by weight of sodium lignin sulfonate were uniformly mixed, and then a small amount of water was added and kneaded, and then granulated and dried to obtain granules.

(2) Preparation of Wettable Powder 10 parts by weight of compound 1, 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) and demol (product) Name; made by Kao Co., Ltd.) and 0.5 parts by weight, and
Then, it was pulverized to obtain a wettable powder.

(3) Preparation of emulsion To 20 parts by weight of compound 1 and 70 parts by weight of xylene, 10 parts by weight of toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) were added and uniformly mixed and dissolved to obtain an emulsion. .

(4) Preparation of Dust Preparation 5 parts by weight of compound 1, 50 parts by weight of talc and 4 parts of kaolin
A powder was obtained by uniformly mixing 5 parts by weight.

Example 3 [Efficacy test] (1) Efficacy test against diamondback moth A compound (I) shown in Tables 2 to 5 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
After diluting to 0 ppm, cabbage leaf pieces (5 × 5 cm) were dipped in each of these chemical solutions for 30 seconds, placed in each plastic cup one by one and air dried. Next, in each of these cups, 10 diamondback moths (third instar larvae) were released, and the cups were capped.
The cup was allowed to stand in a constant temperature room at 5 ° C., and two days later, the number of live and dead insects in each cup was counted to determine the mortality rate. The insecticidal effect is evaluated in four stages (A: 100%, B: 99-80 depending on the range of the mortality rate).
%, C: 79-60%, D: 59% or less). The results are shown in Table 6.

[0129]

[Table 6]

(2) Efficacy test against green leafhoppers Compounds (I) shown in Tables 2 to 5 prepared according to Example 2
Each of the wettable powders of 1 was diluted to 300 ppm with water containing a surfactant (0.01%), rice seedlings were dipped in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. did. Next, 10 green leafhoppers (4th instar larvae) were left in each cylinder, capped with a porous plug, allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the insecticidal rate. The results of the insecticidal effect evaluation are shown in Table 7 by the four-step evaluation method described in (1) above.

[0131]

[Table 7]

(3) Efficacy test against sweet potato root-knot nematode Compounds (I) shown in Tables 2 to 5 prepared according to Example 2
Each of the wettable powders in Table 1 was diluted with water to 20 ppm. 0.5 ml of this drug solution was placed in a test tube, and 0.5 ml of a solution containing 30 to 40 larvae of the second stage larva of Sweet potato Nematoda (within 24 hours of hatching) was further placed. Next, it was allowed to stand in a constant temperature room at 25 ° C., and two days later, the number of live and dead insects was counted with a microscope (40-fold field of view) to determine the nematicidal rate. The results of the evaluation of the nematicidal effect are divided into four levels (A: 1
00%, B: 99-80%, C: 79-60%, D: 5
9% or less). The results are shown in Table 8.

[0133]

[Table 8]

(4) Control efficacy test against barley powdery mildew (preventive effect) Ten barley (cultivar: black wheat) was grown in a plastic flower pot with a diameter of 6 cm, and seedlings at 1.5 leaf stage were grown. In addition, each wettable powder of the compound (I) shown in Tables 2 to 5 prepared according to Example 2 was mixed with a surfactant (0.01%).
Each of them was sprayed with 20 ml per one pot by diluting each to 500 ppm with water containing water. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated. The evaluation of the bactericidal effect was carried out in 6 stages (0: the entire diseased,
1: Lesion area is about 60%, 2: Lesion area is about 40%, 3: Lesion area is about 20%, 4: Lesion area is 10%
Hereinafter, 5: no lesions). The results are shown in Table 9.

[0135]

[Table 9]

(5) Control Efficacy Test for Wheat Leaf Rust (Preventive Effect) 10 wheats (cultivar: Kobushi-komugi) were cultivated in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were cultivated. A wettable powder of the compound (I) shown in Tables 2 to 5 prepared according to Example 2 was mixed with a surfactant (0.01
%) And dilute to 500 ppm with water containing 2% per pot.
Sprayed with 0 ml. After spraying, cultivate in a glass greenhouse for 2 days, and then spore suspension of wheat leaf rust (7 x 10
⁴ spores / ml) were uniformly spray-inoculated on the plants. After inoculation, the seedlings were grown in a glass greenhouse for 1 week, and the degree of wheat leaf rust lesions appearing on the first leaf was investigated. The result is
Table 6 shows the 6-step evaluation method described in (4).

[0137]

[Table 10]

[0138]

INDUSTRIAL APPLICABILITY The novel aminopyrimidine derivative of the present invention has excellent effects such as insecticidal, acaricidal, bactericidal and nematicidal.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yasushi Nakamoto 5 1978, Kogushi, Ube City, Yamaguchi Prefecture Ube Kosan Co., Ltd. Ube Laboratory

Claims (3)

[Claims] 1. The following formula: (Wherein R ¹ represents a halogen atom, a hydroxyl group, a lower acyloxy group or a lower acylthio group; R ² represents a trifluoromethyl group or a cycloalkyl group; A represents a direct bond or a lower alkylene group). Aminopyrimidine derivative. 2. The following formula: (Wherein R ¹ has the same meaning as described in claim 1; X represents a halogen atom) and a pyrimidine derivative represented by the following formula: (In the formula, R ² and A have the same meanings as described in claim 1.)
A method for producing an aminopyrimidine derivative represented by the formula (I) according to claim 1, which comprises reacting with an amine represented by: 3. A pest control agent comprising the aminopyrimidine derivative represented by the formula (I) according to claim 1 as an active ingredient.