WO2003022822A1

WO2003022822A1 - Aralkylaminopyrimidine, process for producing the same and agricultural/horticultural pesticides

Info

Publication number: WO2003022822A1
Application number: PCT/JP2002/009079
Authority: WO
Inventors: Katsutoshi Fujii; Eisuke Funaki
Original assignee: Ube Industries, Ltd.
Priority date: 2001-09-06
Filing date: 2002-09-06
Publication date: 2003-03-20

Abstract

Novel 5-chloro-6-[(R,S)-1-fluoroethyl]-4-[(S)-1-phenylethylamino]pyrimidine represented by the following formula (1) which is useful as a pesticide and has a high safety for warm-blooded animals and aquatic organisms: (1) wherein &ast; represents an asymmetric carbon atom; a process for producing the same; and pesticides containing the same as the active ingredient.

Description

Aralkylaminopyrimidine, its production method and pesticides for agricultural and horticultural use

Technical field

The present invention relates to a novel aralkylaaminopyrimidine (hereinafter referred to as 5_chloro-6-[(R, S) -1-fluoroethyl) useful as a pesticide for agricultural and horticultural use.

Light

_4_ [(S)-1_ phenylethylamino] pyrimidine), its production method and agricultural and horticultural pesticides. book

Background art

JP-A-5-201999 (corresponding US Pat. No. 5,280,025) discloses an aralkylaminopyrimidine represented by the following general formula (4).

In the formula, R ¹ represents a halogen atom, a lower alkoxy group, a lower alkyloxy group, a hydroxyl group, a lower alkoxy group or a lower alkylthio group, R ² represents a lower alkyl group, a hydrogen atom or a cycloalkyl group, and R ³ is equivalent Lower haloalkoxy group, hydrogen atom, lower alkyl group, lower alkoxy group, halogen atom, lower alkylthio group, nitro group, lower haloalkyl group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group Or represents a hydroxyl group, and n represents an integer of 1 to 5. Although these compounds have two asymmetric carbons (*), only the racemic form is disclosed and nothing is described about the optically active form.

Therefore, it is not known that certain optically active substances have excellent activity as pest control for agriculture and horticulture.

The aralkylaminopyrimidine derivative (4) described in JP-A-5-201999 has high activity as a pesticide for agriculture and horticulture, but is safe for warm-blooded animals and aquatic organisms. Is not enough. An object of the present invention is to provide a novel 5-chloro-6-[(R, S) -1-fluoro-ethyl] _4 _ [(S) -1-phenylethyla excellent in safety against warm-blooded animals and aquatic organisms. Mino] pyrimidine, its production method and an agricultural and horticultural pesticide containing the same as an active ingredient.

The inventors of the present invention have studied to solve the above-mentioned problems, and as a result, have found that a novel 5-chloro-amino- 6-[(R, S) —1-fluoroethyl] —4 -— [(S) -11-phenylethylamino It has been found that pyrimidine has remarkably improved the safety against warm-blooded animals and aquatic organisms and has insecticidal, acaricidal, nematicidal and fungicidal activities for agricultural and horticultural use, and completed the present invention.

That is, the present invention is as follows. Disclosure of the invention

The first invention is an aralkylaminobirimidine represented by the following formula (1), that is, 5- (1- (R, S) —1-fluoroethyl) —4-((S) -1 -Phenylethylamino] It relates to pyrimidine.

(1)

In the formula, “*” represents an asymmetric carbon atom.

The second invention has the following formula (2):

In the formula, “*” is as defined above,

4, 5-dicrochloride _ 6— [(R, S) — 1—fluoroethyl] pyrimidine and

The following equation (3):

(3)

(S) — 1-phenylenylamino represented by the following formula, characterized in that it reacts with 5- (1-, 6-)-[(R, S) — 1 _4_ [(S) 1-1-phenylethylamino] pertaining to the production of pyrimidine.

The third invention provides a compound represented by the formula (1), wherein the compound is represented by the formula: 5—black mouth _6 — [(R, S) -1—fluoroethyl] —4 — [(S) — 1—phenylethylamino] pyrimidine. The present invention relates to a pesticide for agricultural and horticultural use as an active ingredient. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

Since compound (1) of the present invention has an amino group, an acid addition salt derived therefrom is also included in the present invention.

Examples of the acid forming an acid addition salt include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, Examples thereof include carboxylic acids such as oleic acid and aconitic acid, sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid, and saccharin.

(Synthetic method)

The method for synthesizing the compound (1) will be described in more detail.

The synthesis method is a method of reacting compound (2) with compound (3) in a solvent in the presence of a base to obtain compound (1).

The type of the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, rigoin, hexane, chlorobenzene, and dichlorobenzene. Chlorinated or non-chlorinated aromatic, aliphatic and cycloaliphatic hydrocarbons, such as chloroform, dichloroethane, trichloroethylene, ethers such as tetrahydrofuran, sioxane, dimethyl ether, etc., acetonitrile, propio Nitriles such as nitrile, ketones such as acetone and methyl ethyl ketone, N, N-dimethylformamide, dimethyl sulfoxide, sulfolane, N, N-dimethylimidazolidinone, N-methylpiperidone, etc. A nonprotonic polar solvent such as And the like mixtures of serial solvents.

The amount of the solvent used can be such that the compound (2) is 5 to 80% by weight, but is preferably 10 to 70% by weight.

The type of base is not particularly limited, and organic and inorganic bases, for example, tertiary amines (triethylamine, etc.), organic bases such as DBU, alkali metal or alkaline earth metal hydrides, hydroxides, carbonates Inorganic bases such as salts and bicarbonates can be mentioned, but tertiary amines are preferred, and triethylamine is more preferred. The amount of the base to be used is 1 to 5 moles, preferably 1.2 to 2.0 moles, relative to Compound (2).

The reaction temperature is not particularly limited, but is in the range of from room temperature to the boiling point of the solvent to be used and is preferably from 60 to L10. The reaction time varies depending on the concentration and the temperature, but is usually 0.5 to 8 hours.

The compound (3) is used in an amount of 1.0 to 5 moles, preferably 1 to 1.1 moles, based on the compound (2).

The compound (2) used in the present invention can be produced by the method shown in the following formula according to the description in JP-A-11-335359 (corresponding US Pat. No. 6,340,757).

(7) (2) In the formula, “*” has the same meaning as described above.

Compound (5) can be produced, for example, by the method shown in the following formula according to the method described in JP-A-11-171834 or US Pat. No. 6,340,757.

(8) (5) As the compound (3), a commercially available product can be used.

After completion of the reaction, the target compound (1) produced as described above is extracted and concentrated. It can be subjected to ordinary post-treatments such as reduction and bubbling, and can be appropriately purified by known means such as various types of chromatography.

(Control effect)

The pests for agricultural and horticultural use which are effective in controlling the compound (1) of the present invention include agricultural and horticultural pests (for example, Hemiptera (Lepidoptera, Lepidoptera, Aphids, Whiteflies, etc.), Lepidoptera) (Coleoptera, Scarabaeidae, Coleoptera, Pests, Scarab beetles, Pieris beetle, etc.), Coleoptera (Tenebrion beetles, Lepidoptera, Chrysomelidae, Chrysomelidae, Scarabaeidae, etc.), Acaridae (Coleoptera, Tetranychidae) ), Nematodes (e.g., Nekosarecentiyu, cystocentiyu, Negusarecentiyu, Singarecentiyu, pine wood nematode), nematodes, sanitary pests (e.g., fly, power, cockroach, etc.) , Storage pests (e.g., Pterodactyla, Pseudocarabidae, etc.), wood pests (eg Examples include termites such as house termites, japonicus termites, and termites, terrestrial bark beetles, beetles, beetles, sink beetles, longhorn beetles, and long-spotted beetles. Also, agricultural and horticultural pathogens (for example, wheat rust) , Barley powdery mildew, cucumber downy mildew, rice blast, tomato late blight, etc.).

(Pest control agent) ''

The pesticidal composition for agricultural and horticultural use of the present invention has remarkable bactericidal, insecticidal, acaricidal and nematicidal effects, and contains the compound (1) as an active ingredient.

The compound (1) can be used alone, but is usually compounded with a carrier, a surfactant, a dispersant, an auxiliary agent, and the like (for example, powders, emulsions, fine granules, granules, water Prepared as a composition such as a wetting agent, an oily suspension, or an aerosol).

Examples of the carrier include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, calcium sand, ammonium sulfate, urea, hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonized hydrogen Toluene, xylene, etc., chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (acetic acid) Liquid carriers such as ethyl, ethylene glycol acetate, dibutyl maleate, etc., alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethyl formamide, dimethyl sulfoxide, etc.), liquid carriers such as water, air, nitrogen And gas carriers such as carbon dioxide and freon (in this case, mixed injection can be performed).

Examples of surfactants and dispersants that can be used to improve the performance of this agent, such as adhesion to animals and plants, absorption, and dispersion, emulsification, and spreading of drugs include alcohol sulfates and alkyl sulfones. Acid salt, lignin sulfonate, and polyoxyethylene glycol ether. In order to improve the properties of the preparation, for example, carboxymethylcellulose, polyethylene dalicol, gum arabic and the like can be used as adjuvants. In the production of the present agent, the above-mentioned carrier, surfactant, dispersant, and auxiliary can be used alone or in combination according to the respective purposes.

When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually 1 to 50% by weight for emulsions, usually 0.3 to 25% by weight for powders, and usually 1 to 90% by weight for wettable powders. % For granules, usually 0.5-5% by weight, oils usually 0.5-5% by weight, aerosols usually 0.1-5% by weight.

These preparations can be used for various purposes by diluting them to an appropriate concentration for each purpose and spraying them on the foliage of plants, soil, or the surface of paddy fields, or directly applying them. Example

Hereinafter, the present invention will be described specifically with reference examples and examples. These do not limit the scope of the present invention. Reference example 1

Synthesis of (R, S) -6- (1-Fluoroethyl) _4-pyrimidone (Compound (6))

93.3 g of methyl (R, S) -4-fluoro-3-oxopentanoate was dissolved in 1000 ml of methanol, and 365 g of 28% sodium methylate (methanol solution) and 98.4 g of formamidine acetate were dissolved. g were added in sequence, and the mixture was heated under reflux at 40 for 12 hours.

After the reaction was completed, the mixture was cooled to 10 or less, and a mixed solution of 95.lg of concentrated sulfuric acid and 85 g of water was added. Then, the mixture was stirred at 50 at 30 minutes, insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from isopropanol to give the target compound (58 g) as colorless crystals.

m.p. 1 70.0 ~: 1 71.5 in

Reference example 2

(R, S) —Synthesis of (1—Fluoroethyl) -1-5-chloro-41-pyrimidone

(R, S) -6- (1-Fluoroethyl) -4-pyrimidone A suspension of 16.O g in 16 Om 1 of dichloroethane was heated to 60, and 8.76 g of chlorine was added in 20 minutes. After blowing, the mixture was further stirred at 6 Ot: for 1 hour.

The reaction solution was cooled to 5, and the precipitated crystals were collected by filtration, washed with water and dried to obtain 17.6 g of the desired product as pale yellow crystals.

Further, the product was purified by recrystallization from isopropanol to obtain 15.4 g of the target compound as colorless powdery crystals.

m.p. 1 90〜 1 91

Reference example 3

Synthesis of (R, S) -4,5-Dichloro-6- (1-fluoroethyl) pyrimidine (Compound (2))

(R, S)-6-(1-fluoroethyl) 1 5 _ Chlor — 4 — Pyrimidone 8 8.3 g was added to 442 ml of ethyl acetate, 71.4 g of N, N-dimethylformamide was added dropwise, and the mixture was stirred for 3 hours to complete the reaction.

After cooling the reaction mixture to 5 or less, it was added to ice-cold water, adjusted to PH3 with 20% sodium hydroxide, the ethyl acetate layer was separated, washed with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the obtained residue was purified by distillation under reduced pressure to obtain 89.8 g of the desired product as a colorless liquid.

b.p.95V / 6.0 ~ 6.5mmHg

Example 1 (Synthesis method of compound (1))

6 — [(R, S) —1-Fluoroethyl] —4 — [(S) —1—Phenethylethylamino] Pyrimidine (Compound 1)

(S) _ 1-Phenylethylamine 15.7 g and triethylamine 16.7 g were dissolved in toluene 20 Om 1 to obtain (R, S) -4,5-dichloro-6- (1— Fluoroethyl) Pyrimidine 23.O g was added, and the mixture was heated and refluxed for 6 hours. After completion of the reaction, triethylamine hydrochloride was separated by filtration, the solvent was distilled off under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ヮ co-gel C-200, developing solvent: n-hexane: ethyl acetate). = 5: 32.0 g of the target product as a pale yellow viscous liquid was obtained by purification in 1). n ²⁸¹ 1. 5728

D

H-NMR (CDC 13, δ p pm)

1.60 to 2.04 (6H, m), 5 35 to 5.44 (1 H, m)

5.70 (1H, b), 5.77 to 600 (1H, d-q),

7.25-7.38 (5H, m), 851 (1H, s) Example 2 (Preparation of formulation)

(1) Preparation of granules

5 parts by weight of the 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 are mixed uniformly. After adding a small amount of water and kneading, Granulation and drying gave 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, Neobelex powder (trade name; manufactured by Kao Corporation) 1.5 parts by weight and Demol (trade name; manufactured by Kao Corporation) 0.5 parts by weight were uniformly mixed and then ground to obtain a wettable powder.

(3) Preparation of emulsion

To 20 parts by weight of the compound (1) and 70 parts by weight of xylene, 10 parts by weight of toxanone (trade name, manufactured by Sanyo Chemical Industries) was added and uniformly mixed to obtain an emulsion.

(4) Preparation of powder

Compound (1) was uniformly mixed with 5 parts by weight of powder, 50 parts by weight of talc and 45 parts by weight of kaolin to obtain a powder.

Example 3 (Efficacy test)

As a comparative compound, 5- (6-((R, S) —1-fluoroethyl) 1-4-((R, S) represented by the following formula (9) described in JP-A-5-201999 ) _1-Phenylethylamino) pyrimidine (Compound No. 19) was prepared and tested in the same manner as the compound of the present invention.

In the formula, “*” represents an asymmetric carbon atom.

(1) Efficacy test for sweet potatoes

Each wettable powder of compound (1) prepared according to Example 2 was diluted to 200 ppm with water, 0.1 ml of which was placed in a test tube, and a solution containing 500 heads of Saccharomyces cerevisiae was added. 9 ml were added. Next, these test tubes were left in a cold room at 25 and observed under a microscope two days later to determine the nematicidal rate. Evaluation of the nematicidal effect was shown in four stages (A: 100-90%, B: 89-80%, C: 79-60%, D: 59% or less), depending on the nematicidal rate range. . Table 1 shows the evaluation results of the nematicidal effect together with comparative compounds.

(2) Test for Nami eight mites

Each wettable powder of compound (1) prepared according to Example 2 was diluted to 300 ppm with water containing a surfactant (0.01%), and 15 N. spider mites were added to each of these solutions. After adult females were allowed to produce eggs for 24 hours, the kidney leaf pieces (diameter 20 mm) from which the adults were removed were immersed for 10 seconds.

Next, each leaf piece was left in a constant temperature room at 25, and three days later, the number of live and dead insects on each leaf piece was counted to determine the acaricidal rate. The acaricidal effect was evaluated in four stages (A: 100%, B: 99-80%, C: 79-60%, D: 59% or less) according to the range of the acaricidal rate. The results of the evaluation of the acaricidal effect are shown in Table 1 together with the comparative compounds:

(3) Potency test for Conaga

Each wettable powder of compound (1) prepared according to Example 2 was diluted to 50 ppm with water containing a surfactant (0.01%), and cabbage leaf fragments (5 cmX (5 cm) was immersed for 30 seconds, placed in each plastic cup, and air-dried.

Next, 10 moths (3rd instar larvae) were released into each of these cups, covered and left in a constant temperature room of 25. After 2 days, the number of live and dead insects in each cup was counted to determine the mortality. . The insecticidal effect was evaluated in four stages (A: 100%, B: 99-80%, C: 79-60%, D: 59% or less) according to the range of the insecticidal rate. Table 1 shows the results of evaluating the insecticidal effect together with comparative compounds.

(4) Efficacy test for Tobi-iron

Each wettable powder of compound (1) prepared according to Example 2 was diluted to 50 ppm with water containing a surfactant (0.01%), and rice seedlings were immersed in each of these drug solutions for 30 seconds. After soaking and air drying, they were inserted into each glass cylinder. Next, 10 glass bolls (4th instar larvae) were released into each of these glass cylinders, plugged with a porous stopper, and left in a constant temperature room at 25. After 4 days, the number of live and dead insects was counted to determine the mortality. Was. The insecticidal effect was evaluated in four stages (A: 100%; B: 99-80%, C: 79-60%, D: 59% or less) according to the range of the insecticidal rate. Table 1 shows the evaluation results of the insecticidal effect together with comparative compounds.

(5) Efficacy test for black leafhopper

Each wettable powder of compound (1) prepared according to Example 2 was diluted to 300 ppm with water containing a surfactant (0.01%), and rice seedlings were immersed in each of these solutions for 30 seconds. After immersion and air drying, they were inserted into each glass cylinder.

Next, ten glass leafhoppers (4th instar larvae) were released into each of these glass cylinders, plugged with a porous plug, and left in a constant temperature room at 25. After 4 days, the number of live and dead insects was counted to determine the mortality. Was. The insecticidal effect was evaluated in four stages (A: 100%, B: 99-80%, C: 79-60%, D: 59% or less) according to the range of the insecticidal rate. Table 1 shows the evaluation results of the insecticidal effect together with comparative compounds.

table 1

(6) Efficacy test for prevention of wheat leaf rust (prevention test)

10 wheat plants (cultivar: Kobushi wheat) are grown in plastic flower pots with a diameter of 6 cm per pot. 1. Hydration of compound (1) prepared according to Example 2 to seedlings at the 5-leaf stage The agent was diluted to 25 ppm with water containing a surfactant (0.01%) and sprayed at 20 ml per pot.

After spraying, cultivate in a glass greenhouse for 2 days, then suspend spores of wheat leaf rust The plant (7 × 10 ⁴ spores Zm 1) was uniformly inoculated by spraying on the plant.

After inoculation, they were grown in a glass greenhouse for one week, and the degree of wheat leaf rust spots on the first leaf was investigated. The evaluation of the bactericidal effect was performed on a 6-point scale compared to the extent of the lesion in the untreated plot.

(0: the whole disease, 1: the lesion area is about 60%, 2: the lesion area is about 40%, 3: the lesion area is about 20%, 4: the lesion area is less than 10%, 5: the disease area (No spots). Table 2 shows the evaluation results of the bactericidal effect together with comparative compounds.

(7) Efficacy test for prevention of powdery mildew of wheat (prophylactic test)

In a 6 cm diameter plastic flowerpot, 10 barley (cultivar: black wheat) are grown per pot, and 1.5 seedlings of the leaf stage are treated with water of the compound (1) prepared according to Example 2. The sum was diluted to 25 ppm with water containing a surfactant (0.01%) and sprayed at 20 ml per pot.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then sporulated spores of the odontic powdery mildew were collected from the diseased leaves and sprinkled evenly over the plants to inoculate them. Next, these were grown in a glass greenhouse for one week, and the degree of the disease spots of powdery mildew which appeared on each first leaf was examined. The evaluation of the bactericidal effect was performed in 6 stages compared to the degree of the lesions in the untreated plot (0: the whole disease, 1: the lesion area is about 60%, 2: the lesion area is about 40%, 3). : Lesion area is about 20%, 4: Lesion area is 10% or less, 5: No lesion). Table 2 shows the evaluation results of the bactericidal effect together with comparative compounds.

Table 2

Example 4 (Safety test) As in the potency test, as a comparative example, (R, S) -5-chloro-6- (1-fluoroethyl) -4- (1-phenylethylethyl) described in JP-A-5-201999 Mino) pyrimidine (Compound No. 19) was prepared and tested in the same manner as the compound of the present invention.

(1) Acute medaka acute toxicity test

Test chemical solution prepared by diluting compound (1) wettable powder prepared according to Example 2 to 0.05 ppm with breeding water (tap water was dechlorinated with activated carbon and made into 25 ^ with a constant temperature water circulator). Three 500 adult Oryzias latipes adult fish, 500 ml in a beaker, habitually reared in an indoor fish breeding aquarium (water temperature 25, light period 13 hours, 喑 period 11 hours) for at least one week, and visual observation to remove abnormal solids Released.

Next, they were reared for 72 hours at room temperature of 25 for 13 hours in the light period and 11 hours in the 期 period, and the number of deaths was examined. The test was performed in duplicate, and at the same time, a control plot with only breeding water was set up, and it was confirmed that there was no death in this plot.

The test results are shown in Table 3 together with comparative compounds.

(2) Daphnia acute toxicity test

Test chemical solution prepared by diluting the wettable powder of compound (1) prepared in accordance with Example 2 to 0.05 ppm with breeding water (tap water was dechlorinated with activated carbon and adjusted to 25 with a constant temperature water circulator) 100 ml was placed in a beaker, and daphnia pulex (Daphnia pulex) bred in an indoor fish breeding aquarium (water temperature: 25 hours, light period: 13 hours, 喑 period: 11 hours) was separated using a test sieve. Adults were separated after 24 hours. Ten larvae obtained within 24 hours after birth were released.

Next, the animals were reared for 48 hours at room temperature of 25 for 13 hours in the light period and 11 hours for the 喑 period, and the number of deaths was examined. The test was performed in duplicate, and at the same time, a control plot with only breeding water was set up, and it was confirmed that there was no death in this plot.

The test results are shown in Table 3 together with comparative compounds.

(3) Mouse acute toxicity test

ICR female mice arrived at the age of 5 weeks, ± 2 ^ at temperature 25, humidity 55 ± 1 0%, ventilation 15 times, lighting 12 hours, housed in a polycarbonate cage with floor bedding in an automatically controlled breeding room, quarantine for one week I chose. Animal chow (CLEA Japan) and tap water were available ad libitum, but they were fasted 4 hours before administration and used for the test.

Compound (1) is suspended in a 1% aqueous solution of CMC (Carboxy methyl eel lulose) at a concentration of 20 Omg / kg of body weight based on the weight at the time of administration, and 1 ml of 20 ml / kg of body weight is added. The stomach sonde was attached to the disposable syringe of No.1 and administered once by gavage.

After the administration, the animals were bred under the same conditions and observed every 24 hours for one week to investigate the number of deaths. At the same time, a control plot without drug was set up, and it was confirmed that there was no death in this plot.

The test results are shown in Table 3 together with comparative compounds.

Table 3

Industrial applicability

The novel 5-chloro-6 _ [(R, S) 1-1-fluoroethyl] 141-[(S) -1-11phenylethylamino] pyrimidine of the present invention is a known compound ((R, S) — Compared to 5- (1-fluoroethyl) -4-1 (1-phenylethylamino) pyrimidine), it has superior safety against warm-blooded animals and aquatic organisms, and has a pest control effect for agriculture and horticulture. Have

Claims

The scope of the claims

1. The following equation (1):

In the formula, “*” represents an asymmetric carbon atom,

An aralkylaminopyrimidine represented by

2. The aralkylaminopyrimidine according to claim 1, which is an acid addition salt.

3. The acid addition salt is hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, methanesulfonic acid, benzenesulfonic acid, p 3. The aralkylaminopyrimidine according to claim 2, which is an acid addition salt of a compound selected from the group consisting of toluenesulfonic acid and saccharin.

4. Equation (2):

In the formula, “*” represents an asymmetric carbon atom,

4,5-Dichloro-6-[(R, S) —1-Fluoroethyl] pyrimidine represented by

The following equation (3): H 2 ゥ N "(S) The following formula (1) characterized by reacting with (S) -phenylethylamino represented by (3):

In the formula, “*” is as defined above,

A method for producing aralkylaminopyrimidine represented by

5. The process for producing an aralkylaminopyrimidine according to claim 4, wherein the compound (3) is used in an amount of 1.0 to 5 times the mole of the compound (2).

6. The process for producing aralkylaminopyrimidine according to claim 4, wherein the reaction is carried out in the presence of a base.

7. The process for producing an aralkylaminopyrimidine according to claim 6, wherein the base is used in an amount of 1 to 5 moles per mole of the compound (2).

8. The process for producing aralkylaminovirimidine according to any one of claims 4 to 7, wherein the reaction is performed in the presence of a solvent.

9. The process for producing an aralkylaminopyrimidine according to claim 8, wherein the solvent is used in an amount such that the amount of the compound (2) is from 5 to 80% by weight.

10. The process for producing aralkylaminobirimidine according to claim 9, wherein the reaction is carried out at a temperature from room temperature to a temperature not higher than the boiling point of the solvent used.

11. The process for producing an aralkylaminopyrimidine according to claim 4, wherein the reaction is carried out at 60 to 11O.

12. The following equation (1):

In the formula, “*” is as defined above,

A pest control agent comprising an aralkylaminopyrimidine represented by the following formula as an active ingredient.