JPH0426681A - Alkylaminopyrimidine derivative, production thereof and noxious organism controlling agent - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [R<1> is H, 1-4C alkyl or 3-6C cycloalkyl; R<2> and R<3> are 1-4C alkyl or halogen or R<2> and R<3>, together C to which they are linked, are condensed with the pyrimidine ring to form 5- to 6-membered ring which may have S; R<4> is H or 1-4C alkyl; R<5> is 3-5C alkenyl, 3-5C alkynyl, (substituted) phenyl, (substituted) aralkyl- or (substituted) 1-10C alkyl; m is 1-10; n is 0-21]. EXAMPLE:5-Chloro-6-ethyl-4-(8-methylthiooctylamino)pyrimidine. USE:A noxious organism controlling agent. PREPARATION:A compound expressed by formula II (X is leaving group) is reacted with a compound expressed by formula III, preferably in the presence of a base (e.g. triethylamine) in a solvent (e.g. benzene).

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a pest control agent containing a novel alkylaminopyrimidine derivative or an acid addition salt thereof as an active ingredient. [Prior Art] Since the alkylaminopyrimidine derivative of the present invention is a new compound, its biological activity is completely unknown. [Problems to be Solved by the Invention] An object of the present invention is to provide a novel alkylaminopyrimidine derivative or an acid addition salt thereof, a method for producing the same, and a pest control agent containing the same as an active ingredient. [Means for Solving the Problems] As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that a novel alkylaminopyrimidine derivative has remarkable pest control activity. The invention was completed. That is, the present invention provides (1) the following formula: (wherein R1 is a hydrogen atom, a C1 to C4 alkyl group,
or represents a 03-C6 cycloalkyl group; R2 and R
3 represents a Cl-C4 alkyl group or a halogen atom; or R2 and R3 may be fused together with the carbon atom to which they are bonded to a pyrimidine ring and have one sulfur atom. Represents a saturated or unsaturated 5- or 6-membered ring, on which there are 1 to 2 01-C4 alkyl groups,
or may be substituted with a halogen atom; R" represents a hydrogen atom or an alkyl group of 01 to C4, and R5 represents 03 to
C5 alkenyl group, C3-C5 alkynyl group, phenyl group which may have a substituent. Aralkyl group which may have a substituent, or 01-C
4 alkoxy group or 01~C4 alkylthio group or 1~
01 to CIO optionally substituted with 3 halogen atoms
represents an alkyl group; m represents an integer of 1 to 10; n represents 0.1 or 2; ) Alkylaminopyrimidine derivatives or acid addition salts thereof. (2) The compound represented by the following formula: (in the formula, R', R'' and R3; X represents a leaving group) and the following formula: R''' (in the formula, R4 , R5, m and n have the same meanings as described above. 3) A compound represented by the following formula: (wherein R1, R2, R3, R4 and m have the same meanings as above) and the following formula: R''-X (V)
(In the formula, R5 and X have the same meanings as above.) has the same meaning as above.) Method for producing an alkylaminopyrimidine derivative or an acid addition salt thereof (4) Reacting the alkylaminopyrimidine derivative represented by the above formula (I-1) with a peroxide. In the above formula (I), which is characterized by Method for producing aminopyrimidine derivatives or acid addition salts thereof (5) This invention relates to a pest control agent containing an alkylaminopyrimidine derivative represented by the above formula (1) or an acid addition salt thereof as an active ingredient. The present invention will be explained in detail below. Novel pyrimidine derivative (I) which is the above-mentioned target compound
In the compounds (If) to (V), which are raw materials for their production, R' is a hydrogen atom, a C1-C4 linear or branched alkyl group (e.g., methyl 5-ethyl, propyl, isopropyl, butyl , isobutyl, 5ec-butyl, L-butyl, etc.), C3-C6 cycloalkyl group (
For example, cyclopropyl, cyclopentyl, cyclohexyl, etc.), halogen atoms, etc. are preferred; hydrogen atoms and 01-C4 linear or branched alkyl groups are preferred; more preferred are 01-C4 straight-chain or branched alkyl groups.
As the alkyl group, a methyl group is preferable. R2 and R'' are C1 to C4 linear alkyl groups (for example, the lower alkyl groups described above), halogen atoms (for example, fluorine, chlorine, bromine, iodine, etc.). ); Preferably, in the 01-C4 alkyl group, C1-C
A linear alkyl group of 4 is preferable. Alternatively, R2 and R3 are fused to a pyrimidine ring together with the carbon atom to which they are bonded, and represent a saturated or unsaturated 5- or 6-membered ring that may have one sulfur atom, and The ring may be substituted with 1 to 2 alkyl groups having 1 to 4 carbon atoms or a halogen atom; however, as the ring condensed with a carbon atom to a pyrimidine ring, these are preferable. R4 is a hydrogen atom, a 01-C4 linear or branched alkyl group (for example, those described above),
Examples include a 03-C6 cycloalkyl group; preferably a hydrogen atom or a 01-C4 alkyl group; among the C1-C4 alkyl groups, an ethyl group is more preferred. R5 is an alkenyl group of 03 to C5 (e.g., allyl, 1-butenyl-52-butenyl, 1-methylallyl,
2-methylallyl, 2-pentenyl, isoprenyl, etc.), 03-C5 alkynyl groups (e.g., ■-propynyl, 2-propynyl, 2-butynyl, etc.), substituents (e.g., lower alkyl, halogen atom, halo-lower alkyl, etc.) ) (e.g. phenyl, 4-chlorophenyl, 4-fluorophenyl 4-
methylphenyl (4-trifluoromethylphenyl, etc.), aralkyl groups which may have substituents (e.g., lower alkyl, halogen atom, lower alkyl, etc.) (e.g., benzyl, 4-chlorobenzyl, 4-fluoro benzyl, 4-methylbenzyl, 3,4-dichlorobenzyl, α-methylbenzyl, α-ethylbenzyl), 01 to C4 alkoxy group (e.g., methoxyethyl, 9ethoxyethyl, propoxyethyl, etc.), or C1
-A C4 alkylthio group (eg, methylthiomethyl, etc.) or a C3-C6 cycloalkyl group (eg, cyclopropylmethyl, etc.). Examples include linear or branched alkyl groups of 01 to CIO which may be substituted with any one of 1 to 3 halogen atoms; preferably, in the alkenyl group of 03 to C5, allyl For the 03-C5 alkynyl group, a 210 vinyl group is preferred; for the aralkyl group which may have a substituent, a benzyl group or α-methylbenzyl group is preferred, and for the 01-C4 alkoxy group, , a C1 to C4 alkylthio group, a C3 to C6 cycloalkyl group, or a linear or branched alkyl group of 01 to CIO, which may be substituted with 1 to 3 halogen atoms, , a 01-C4 alkoxy group, a C1-C4 alkylthio group, or a 01-C10 linear alkyl group optionally substituted with 1-3 halogen atoms; C1-C4 Is it an alkoxy group? More preferred examples of the 01-C4 alkylthio group or the C1-C10 linear alkyl group optionally substituted with 1-3 halogen atoms include:
C1-C4 alkyl group, 01-C4 alkyl group substituted with 01-C4 alkoxy group, 01-C4 alkyl group substituted with C1-C4 alkylthio group, or 1-C4 alkyl group substituted with C1-C4 alkylthio group;
Examples include 01-C4 alkyl groups substituted with three halogen atoms. m represents an integer of 1 to 1O; preferably, an integer of 3 to 8. n represents 0.1 or 2. X is not particularly limited, and for example, a halogen atom (
chlorine, bromine, iodine, etc.), alkylthio groups (methylthio, ethylthio, propylthio, butylthio, etc.), alkanesulfonyloxy groups optionally substituted with halogen (methanesulfonyloxy,
Exensulfonyloxy, trifluoromethanesulfonyloxy, etc.), arylsulfonyloxy groups (henzensulfonyloxy, p-)luenesulfonyloxy, etc.), and hydroxyl groups. Since the compound (1) of the present invention has an amino group,
Its acid addition salts can be easily formed. Acids that can be used to form such acid addition salts include, for example, inorganic acids such as hydrobromic acid, nitric acid,
sulfuric acid, phosphoric acid, etc.), carboxylic acids (e.g., formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, etc.), organic sulfonic acids (e.g., methanesulfonic acid, benzenesulfonic acid, P- ) luenesulfonic acid, etc.). When the carbon atom marked with * in the starting compound is an asymmetric carbon atom, the obtained target compound (I) includes individual optical isomers, racemic compounds, or mixtures thereof. The object compound (1) of the present invention can be obtained, for example, by the production method (A-C) shown below. (Manufacturing method A) (n) (DI) 1111÷ (I) (wherein, R', R2, R3, R', R5, m, n and
is synonymous with the above description. ) To obtain the target compound (I), the starting compound (n) and the starting compound (I [ Preferably, it is produced by reacting with
It can be obtained by reacting without adding a base, or it can be obtained by heating and dissolving raw material compounds (n) and (III) without solvent. The solvent is not particularly limited as long as it is not directly involved in this reaction, and examples include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, and dichloroethane. chlorinated or non-chlorinated aromatic, aliphatic, cycloaliphatic hydrocarbons such as , trichlorethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; acetone, methyl ethyl ketone, etc. Ketones; alcohols such as methanol, ethanol, ethylene glycol, etc. or their hydrates, N, N
- amides such as dimethylformamide, N,N-dimethylacetamide, etc.; organic bases such as triethylamine, pyridine, N,N-diethylaniline, etc.;
Examples include 1<3>-dimethyl-2-imidazolidinone; dimethyl sulfoxide; and mixtures of the above solvents. Examples of the base include triethylamine, pyridine,
Organic bases such as N,N-diethylaniline, etc.; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc.; sodium amide, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, etc. Examples include inorganic bases. In order to increase the reaction rate, it is preferable to add 4-(N,N-dimethylamino)pyridine as a catalyst. The reaction temperature is not particularly limited, but is usually within a temperature range from room temperature to the boiling point of the solvent used, and the reaction time can be shortened by heating within the temperature range below the boiling point. (Hereinafter, blank spaces) (Manufacturing method B) In the above formula (I), the compound (■1) in which n is 0 can be manufactured by the following method. (IV) (V) (In the formula, R', R2, R', R', R5, m and X have the same meanings as described above.) The target compound (1-1) is the eliminated compound HX In order to make the reaction smooth by supplementing, it is usually preferable to produce by reacting starting compound (IV) and starting compound (V) in a solvent in the presence of a base. Examples of the solvent and base include those described in Production Method A. Similarly to Production Method A, the reaction temperature is not particularly limited, and is usually within the temperature range from room temperature to the boiling point of the solvent used,
The reaction time can be shortened by heating at a temperature below the boiling point. (Production method C) In the formula (1), a compound in which n is 1 or 2 (I-2
) can be produced by the following method. (In the formula, R', R2, R', R', R5, m and X are as defined above; n' represents 1 or 2.) The target compound (1-2) is a starting compound It can be produced by reacting (I-1) with peroxide (VI). As the solvent, those described in Production Method A can be mentioned. The peroxide is not particularly limited, and examples thereof include hydrogen peroxide, m-chloroperbenzoic acid, sodium metaperiodate, potassium permanganate, and sodium hypochlorite. The reaction temperature is not particularly limited as long as it is carried out within the temperature range from -10°C to the boiling point of the solvent used, but usually -1
0°C to room temperature is preferred. As described above, the target compound (1) produced by Production Methods A to C can be appropriately purified by known means such as recrystallization and various chromatography. The acid addition salt of the target compound (1) can be easily obtained, for example, by introducing an acid into the reaction solution after completion of the reaction and then removing the solvent. The raw material compound (II) used in the present invention can be obtained by, for example, the method described in Journal of Chemical Society (J. C05), 3478-3481 (1955) as shown in the following formula. ,
It can be easily manufactured. (In the formula, R', R" and R" have the same meanings as described above.) (Hereinafter, blank) The raw material compound (III) used in the present invention can be prepared by, for example, as shown in the following formula: It can be easily manufactured. X-CH-R6 l n and X are as defined above. The raw material compound (It/) used in the present invention can be easily produced, for example, by the following formula. (TV) (In the formula, R', R2, R3, R', m and Pests [e.g., Hemiptera (planthoppers,
leafhoppers, aphids, mealybugs, etc.), Lepidoptera (armhoppers, mealybugs, mealybugs, cabbage moths, etc.), Coleoptera (lepidoptera, mealworms, etc.)
Weevils, potato beetles, etc.), Acariformes (citrus spider mites,
(e.g., two-spotted spider mites, etc.), sanitary pests (e.g., flies, insects, cockroaches, etc.), stored grain pests, cat nematodes in the soil,
Examples include pine nematode and mites, and agricultural and horticultural pathogens (eg, wheat leaf rust, barley powdery mildew, cucumber mildew, rice blast, tomato late blight, etc.). The pest control agent of the present invention has remarkable insecticidal, acaricidal, nematicidal, and bactericidal effects, and contains one or more types of compound (I) as an active ingredient. The pest control agent of the present invention contains one or more compounds (1) as an active ingredient. Compound (I) can be used alone, but it is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent, etc. (e.g., powder, emulsion, fine granules, 1 granule, hydrated) by a conventional method. It is preferable to prepare a composition such as a drug, an oily suspension, an aerosol, etc.). Examples of carriers include talc and bentonite. Clay, kaolin, diatomaceous earth, white carbon, vermiculite slaked lime, silica sand, ammonium sulfate. Solid carriers such as urea; hydrocarbons (kerosene, mineral oil, etc.)
, aromatic hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters ( Ethyl acetate, ethylene glycol acetate-1, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethyl sulfoxide, etc.), liquid carriers such as water; air, Examples include gas carriers such as nitrogen, carbon dioxide, and freon (in this case, they can be mixed and injected). Examples of surfactants and dispersants that can be used to improve the adhesion and absorption of powders to animals and plants, as well as the dispersion, emulsification, and spreading of drugs, include alcohol sulfate esters and alkyl sulfonates. , lignin sulfonate,
Examples include polyoxyethylene glycol ether. In order to improve the properties of the preparation, for example,
Carboxymethyl cellulose, polyethylene glycol, gum arabic, etc. can be used as adjuvants. In the standard production, the above-mentioned carrier 5 surfactant 9 dispersant and auxiliary agent can be used individually or in an appropriate combination depending on the purpose. When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
-25% by weight for wettable powders, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for weight agents, usually 0.5 to 5% by weight for oils, and usually 0.1 to 5% by weight for aerosols. be. These preparations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, or the water surface of paddy fields, depending on the purpose.
Alternatively, it can be applied directly for various purposes. [Example] Hereinafter, the present invention will be illustrated by examples. Note that these Examples do not limit the scope of the present invention. Example 1 ■

[Synthesis of 5-chloro-6-nityl-4-(8-methylthiooctylamino)pyrimidine (Compound 1)] The target compound (1) was synthesized using Production Method A as described below.
) was able to be obtained. 4.0 g of 8-methylthiooctylamine, which is the starting compound (I [l)], and 4 ml of triethylamine were dissolved in 50 mL of toluene, and 4.0 g of 45-dichloropyrimidine, which was the starting compound (It), was added, and the mixture was stirred. The mixture was heated under reflux for 5 hours. After the reaction was completed, the produced triethylamine hydrochloride was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel (200, toluene:ethyl acetate-3:
1 elution) and is a colorless oil (shown as Compound 1 in Table 1 below).
5.7g of was obtained. ■

[Synthesis of 5-chloro-6-nityl-1-(El (1 phenylethylthio)octylaminocopyrimidine (Compound 57)] The target compound (1
) was able to be obtained. 5-chloro-6-nityl-4, which is the raw material compound (TV)
-(8-mercaptooctylamino)pyrimidine 0.8
0 g, 0.58 g of 1-phenylethyl bromide and 0.55 g of potassium carbonate were dissolved in dimethylformamide (DM
F) was added to 10 ml and heated at 100°C for 5 hours while stirring. After the reaction was completed, the product was extracted using ethyl acetate, and the extract was washed with water, dried over anhydrous sodium sulfate, and then ethyl acetate was distilled off under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, toluene:ethyl acetate-3:
0.85 g of the target compound (shown as Compound 57 in Table 1 below) was obtained as a colorless oil. ■

[Synthesis of 5-chloro-6-nityl-4-(8-methylsulfinyloctylamino)pyrimidine (compound 7)] The target compound H) was prepared as described below in Production Method C.
I was able to get 0.8 g of sodium metaperiodate was dissolved in 8 ml of water, cooled to 0°C, and mixed with 1.2 g of ethanol, which is the raw material compound (I-1) (Example 1-■), and 5 m of ethanol under stirring. The solution was added dropwise. After the dropwise addition was completed, the reaction was completed by stirring at the same temperature for 1 hour. After the reaction is complete, ethanol is distilled off from the reaction solution under reduced pressure, the product is extracted using ethyl acetate, the extract is washed with water, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure. did. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, ethanol:ethyl acetate-1).
:9 elution) to obtain 0.8 g of the target compound (shown as Compound 7 in Table 1 below) as colorless powdery crystals. ■

[Synthesis of 5-chloro-6-nityl-4-(8-methylsulfonyloctylamino)pyrimidine (Compound 8)] The target compound (I
) was able to be obtained. 2.0 g of raw material compound (r-1) (Example I-■)
was dissolved in 30 mfl of dichloromethane, cooled to below 5°C, 3°Og of m-chloroperbenzoic acid was added under stirring, and the mixture was stirred for 3 hours. After the reaction was completed, the reaction mixture was washed with an aqueous IN sodium hydroxide solution, then washed with water, dried over anhydrous sodium sulfate, and then dichloromethane was distilled off under reduced pressure. The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, toluene:ethyl acetate-1:
1 elution) to obtain 1.8 g of the target compound (shown as Compound 7 in Table 1 below) as colorless powdery crystals. ■ [Synthesis of compounds 2 to 6, 9 to 8o in Table 1] ■ to ■
The target compound (I) as shown in Table 1 (shown as Compounds 2-6, 9-56, 58-81 in Table 1 below) .) was able to be obtained. (The following is a blank space) Example 2 ■ [Preparation of granules] Compound 1 in 5N parts, 2 35 parts by weight of bentonite, 57 parts by weight of Kuruk, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Atlas), and lignin sulfonic acid. Two parts by weight of soda were uniformly mixed, then a small amount of water was added and kneaded, followed by granulation and drying to obtain granules. ■ [Preparation of wettable powder] 10 parts by weight of Compound 1, 7 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 Atlas Co., Ltd.) and 0.5 parts by weight of Demol (trade name; manufactured by Kao Atlas Co., Ltd.) are uniformly mixed, and then pulverized and hydrated. obtained the drug. ■ [Preparation of emulsion] To 20 parts by weight of Compound 1 and 70 parts by weight of xylene, add 10 parts by weight of toxanone (trade name; manufactured by Sanyo Chemical Industries, Ltd.), mix uniformly, and dissolve to obtain an emulsion. Preparation] 5 parts by weight of compound 1, 50 parts by weight of talc, and kaolin 4
A powder was obtained by uniformly mixing 5 parts by weight. Example 3 ■ [Efficacy test against diamondback moth] The target compound shown in Table 1 prepared according to Example 2 (1
) with water containing surfactant (0.01%).
00 ppm, and add cabbage leaf pieces (5 c
m x 5 cm) was immersed for 30 seconds, air-dried, and then placed in a plastic cup. Then, 10 3rd instar diamondback moth larvae were released into the container, the container was covered with a lid, and the container was left in a thermostatic chamber at 25° C. for 2 days.The number of live and dead larvae was counted to determine the mortality rate. Evaluation of drug effects is divided into four stages (A) depending on the range of mortality rate.
: 100%, B: 99-80%, C near 9-60%, D
:59% or less). The results are shown in Table 2. Table ■ [Efficacy test against brown planthopper] Each wettable powder of the target compound (I) shown in Table 1 prepared according to Example 2 was diluted to 300 ppm with water containing a surfactant (0.01%). Then, each rice seedling was immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. Then, after releasing 10 third instar brown planthopper larvae into each cylinder and sealing it with a porous plug, the cylinder was kept at 25°C for 4 days.
The cylinders were left in a constant temperature chamber, and the number of live and dead weights in each cylinder was counted to determine the mortality rate. The results were evaluated using the four-stage evaluation method described in ① above.
It is shown in Table 3. Table ■Efficacy test against female adult spider mite C] Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 3 was mixed with water containing a surfactant (0.01%) at a concentration of 300 ppm.
Each kidney bean leaf piece (diameter 20 mm) in which 10 female adult two-spotted spider mites were parasitized in each of these chemical solutions was diluted to 10
Dipped for seconds at a time. Next, each of these leaf pieces was left in a constant temperature room at 25°C for 3
Days later, the number of live and dead insects on each leaf was counted to determine the acaricidal rate. The results were evaluated using the four-stage evaluation method described in ① above.
It is shown in Table 4. Table 4 ■ [Efficacy test against sweet potato nematode] Target compound shown in Table 1 prepared according to Example 2 (I
) was diluted with water to 20 ppm. Then, put 0.5 d of the drug solution into the examiner, and add 30 to 40 d
0.57 of a liquid containing sweet potato nematode heads was added. Two days after being left in a constant temperature room at 25°C, the number of live and dead insects was counted under a microscope to determine the survival rate. Evaluation of drug effects is divided into four stages (A) depending on the range of mortality rate.
:100~90%, B:89~80%, C near 9~60
%, D=59% or less). The results are shown in Table 5. (Hereafter, blank space) Table ■ [Control efficacy test against wheat rust (preventive effect)
] Wheat (variety: Kobushi wheat) was grown in plastic flower pots with a diameter of 6 cm, 10 plants per pot, and the target compounds shown in Table 1 prepared according to Example 2 were added to the seedlings at the 1.5 leaf stage. The hydrating agent (1) was mixed with a surfactant (0,01
%) per pot to 500 ppm.
0mj2T: Sprayed. After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then a spore Q%i solution (7 x 10' spores/kai) of wheat rust (Puccinia dispersa) was sprayed uniformly onto the plants. After inoculation, the plants were grown in a glass greenhouse for one week, and the extent of wheat rust lesions that appeared on the first leaves was examined. The drug effect was evaluated by comparing the degree of lesions in the untreated area.
6 stages (0: whole disease affected, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, 5: No lesion). The results are shown in Table 6. Table ■ [Control efficacy test against rice blast disease (preventive effect)] Ten rice plants (variety: Nipponbare) were grown per pot in plastic flower pots with a diameter of 6 cm, and the test was conducted on seedlings at the 1.5 leaf stage. Each hydrating agent of the target compound (I) shown in Table 1 prepared according to Example 40 was diluted to 500 ppm with water containing a surfactant (0.01%), and 20 m2 per pot was prepared.
It was dispersed. After spraying, the rice blast fungus (Pyriculariao nigra) prepared from diseased leaves was cultivated in a glass greenhouse for 2 days.
ryzae) conidial suspension (7X10'spores/m
ff1) was uniformly spray-inoculated onto the leaves of the plants. After inoculation, the plants were grown in a humid room at 28°C for 5 days, and the extent of rice blast lesions that appeared on the leaves was examined. The results are evaluated using the 6-level evaluation method described in (■) above.
It is shown in Table 7. (Hereinafter, blank spaces) Table 1 [Effects of the Invention] The novel alkylaminopyrimidine derivatives and acid addition salts thereof of the present invention are agricultural chemicals useful as pest control agents.

Claims (5)

[Claims] (1) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 is a hydrogen atom, a C1 to C4 alkyl group,
or represents a C3-C6 cycloalkyl group; R^2 and R^3 represent a C1-C4 alkyl group or a halogen atom; or R^2 and R^3 are bonded together. saturated or unsaturated 5 or 6 fused to the pyrimidine ring with a carbon atom and optionally having one sulfur atom
Represents a membered ring, and 1 to 2 C1-C4 alkyl groups or halogen atoms may be substituted on the ring; R^
4 represents a hydrogen atom or a C1 to C4 alkyl group; R
^5 is a C3 to C5 alkenyl group, a C3 to C5 alkynyl group, a phenyl group which may have a substituent, an aralkyl group which may have a substituent, or a C1 to C4 alkoxy group or C1 ~ Represents a C4 alkylthio group or a C1 to C10 alkyl group optionally substituted with 1 to 3 halogen atoms; m represents an integer of 1 to 10; n is 0, 1
Or represents 2. ) Alkylaminopyrimidine derivatives or acid addition salts thereof. (2) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R^1, R^2 and R^3 have the same meanings as described in claim 1; X represents a leaving group. ) and the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the formula, R^4, R^5, m and n have the same meanings as in claim 1.) 2. A method for producing an alkylaminopyrimidine derivative represented by formula (I) or an acid addition salt thereof according to claim 1, characterized in that the alkylaminopyrimidine derivative represented by formula (I) is reacted with a compound represented by formula (I). (3) The following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) (In the formula, R^1, R^2, R^3, R^4 and m have the same meanings as in claim 1. ) and the compound represented by the following formula: R^5-X(V) (wherein R^5 and X have the same meanings as in claims 1 and 2). In the formula (I) according to claim 1, which is characterized by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼( I -1) (In the formula, R^1, R^2, R^3, R^4 and m has the same meaning as defined in claim 1.) A method for producing an alkylaminopyrimidine derivative or an acid addition salt thereof. (4) In the formula (I) according to claim 1, which is characterized by reacting the alkylaminopyrimidine derivative represented by formula (I-1) according to claim 3 with a peroxide, the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc.▼( I -2) (In the formula, R^1, R^2, R^3, R^4 and m have the same meaning as described in claim 1; n' is 1 or 2) or an acid addition salt thereof. (5) A pest control agent comprising an alkylaminopyrimidine derivative represented by formula (I) or an acid addition salt thereof according to claim 1 as an active ingredient.