JP2649119B2 - Alkylaminopyrimidine compounds, their preparation and pest control agents - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel alkylaminopyrimidine compound which is useful as a pesticide such as an insecticide, an acaricide, a nematicide, a fungicide and the like, and a process for producing the same.

[0002]

2. Description of the Prior Art Since the alkylaminopyrimidine compound of the present invention is a novel compound, its pest control activity is not known.

[0003]

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a novel alkylaminopyrimidine compound, a method for producing the same, and a pesticidal composition containing the compound as an active ingredient.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a novel alkylaminopyrimidine compound has a remarkable activity for controlling pests. Thus, the present invention has been completed. That is, the present invention is as follows. A first invention provides a compound (I) of the following formula:

[0005]

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(Wherein R ¹ and R ² independently represent an alkyl group having 1 to 6 carbon atoms or a halogen atom; R ³ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms) A haloalkyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkylsulfinyl group having 1 to 6 carbon atoms; R ₄ is an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, or an alkenyl having 2 to 6 carbon atoms. A alkynyl group having 2 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, or a cycloamino group having 2 to 10 carbon atoms; m represents an integer of 1 to 20; n is 0-2
Represents an integer. )). The second invention is based on the following formula (I
I):

[0007]

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(Wherein R ¹ , R ² and m are as defined above) and the following formula (III):

[0009]

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Wherein R ⁴ and n have the same meanings as described above; and X represents a leaving group. R
³ relates to a method for producing an alkylaminopyrimidine compound represented by a hydrogen atom. The third invention is based on the following formula (I
V):

[0011]

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(Wherein R ¹ , R ² and X are as defined above) and the following formula (V):

[0013]

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Wherein R ³ , R ⁴ , m and n have the same meanings as described above, and reacting with a compound represented by the formula (I). The present invention relates to a method for producing an aminopyrimidine compound. The fourth invention relates to a pesticidal composition containing an alkylaminopyrimidine compound represented by the above formula (I) as an active ingredient.

Hereinafter, the present invention will be described in detail. Novel alkylaminopyrimidine compounds [compound (I), compound (I-1), compound (I
-2)] and the compound of the production raw material [compound (II),
(III), (III ′), (IV), (V)], R ¹ , R ² , R ³ , R ⁴ , R ⁵ , m, n, n ′ and X are as follows.

Examples of R ¹ include a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.). An alkyl group having preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms (for example, methyl group, ethyl group, n-propyl group, i-propyl group, etc.); The halogen atom is preferably a chlorine atom.

Examples of R ² include a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.). An alkyl group having preferably 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms (for example, methyl group, ethyl group, n-propyl group, i-propyl group, etc.); The halogen atom is preferably a chlorine atom or a fluorine atom.

R ³ is a hydrogen atom or a group having 1 to 1 carbon atoms.
6 alkyl groups, haloalkyl group having 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, alkylsulfinyl having 1 to 6 carbon atoms And the like.

As the alkyl group having 1 to 6 carbon atoms for R ³ , a straight-chain or branched alkyl group can be mentioned; preferably, an alkyl group having 1 to 4 carbon atoms is preferable. More preferably, one to three (eg, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, etc.) are preferable.

Examples of the haloalkyl group having 1 to 6 carbon atoms for R ³ include a linear or branched alkyl group,
Examples include those having a halogen atom (eg, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.) as a substituent; the alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 4 carbon atoms. 3 (for example, methyl group, ethyl group, n-propyl group, i-propyl group, etc.)
The halogen atom is preferably a fluorine atom. The most preferable haloalkyl group includes, for example, a difluoromethyl group.

Examples of the alkylsulfonyl group having 1 to 6 carbon atoms for R ³ include those having a linear or branched alkyl group; the alkyl group preferably has 1 to 6 carbon atoms. 4, more preferably 1 to
Three (for example, a methyl group, an ethyl group, an n-propyl group,
and an i-propyl group. The most preferable alkylsulfonyl group includes, for example, a methylsulfonyl group.

Examples of the alkylthio group having 1 to 6 carbon atoms for R ³ include those having a linear or branched alkyl group; the alkyl group preferably has 1 to 4 carbon atoms. , More preferably 1 to 3 (eg, methyl group, ethyl group, n-propyl group, i-
Propyl group). The most preferred alkylthio group includes, for example, a methylthio group.

Examples of the alkylsulfinyl group having 1 to 6 carbon atoms for R ³ include those having a linear or branched alkyl group; the alkyl group preferably has 1 to 6 carbon atoms. 4 pieces, more preferably 1
〜3 (eg, methyl, ethyl, n-propyl, i-propyl) are preferred. The most preferred alkylsulfinyl group includes, for example, a methylsulfinyl group.

R ⁴ is an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a phenyl group, a pyridyl group, an alkenyl group having 2 to 6 carbon atoms, 2 to 6 alkynyl groups, 1 carbon atom
And 6 alkylamino groups, and cycloalkylamino groups having 2 to 10 carbon atoms.

The alkyl group having 1 to 6 carbon atoms for R ⁴ includes a linear or branched alkyl group; the alkyl group preferably has 1 to 4 carbon atoms (for example, Methyl group, ethyl group, n-propyl group, i-
Propyl, n-butyl, i-butyl, t-butyl, etc.).

The haloalkyl group having 1 to 6 carbon atoms for R ⁴ includes a linear or branched alkyl group,
Examples include those having a halogen atom (eg, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.) as a substituent; the alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 4 carbon atoms. 3 (for example, methyl group, ethyl group, n-propyl group, i-propyl group, etc.)
The halogen atom is preferably a chlorine atom or a fluorine atom. And as the most preferred haloalkyl group,
For example, a trifluoromethyl group, a chloromethyl group, a fluoromethyl group and the like can be mentioned.

The phenyl group for R ⁴ may be a substituted or unsubstituted phenyl group;
A nitro group and a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like can be mentioned, but a chlorine atom is preferred) is preferred; the position of the substituent is preferably at the 6-position. .

The pyridyl group in ^{R 4} (e.g., 2-pyridyl group, 3-pyridyl group and the like) as may have can be mentioned substituted or unsubstituted; as the substituent, ^{R 4}
And the same haloalkyl group having 1 to 6 carbon atoms (preferably a trifluoromethyl group) described above, and the position of the substituent is preferably the 2-position.

As the alkenyl group having 2 to 6 carbon atoms for R ⁴ , a linear or branched alkenyl group may be mentioned; the number of carbon atoms is preferably 2 to 3; Is preferably a propenyl group (for example, an allyl group).

Examples of the alkynyl group having 2 to 6 carbon atoms for R ⁴ include straight-chain or branched ones; the number of carbon atoms is preferably 2 to 3; More preferably, a propynyl group (for example, a propargyl group, etc.) is preferred.

The alkylamino group having 1 to 6 carbon atoms for R ⁴ has 1 or 2 linear or branched alkyl groups (for example, monoalkylamino group, dialkylamino group and the like). The alkyl group preferably has 1 to 3 carbon atoms (eg, a methyl group, an ethyl group, an n-propyl group,
i-propyl, n-butyl, i-butyl, t-butyl, etc.). The most preferred alkylamino group includes a dialkylamino group (for example, a dimethylamino group).

The cycloamino group having 2 to 10 carbon atoms for R ⁴ preferably has 2 to 7 carbon atoms; more preferably 2 to 5 carbon atoms (for example, a piperazyl group). Good. Examples of R ⁵ include the same alkyl group having 1 to 6 carbon atoms as described for R ⁴ .

[0033] As X is (as described in the R ⁴⁾ a halogen atom, arylsulfonyloxy group (benzenesulfonyloxy, p- Torr en sulfonyloxy, etc.)
And the like; a halogen atom is preferred. m represents an integer of 1 to 20. n and n ′ represent an integer of 0 to 2.

(Production Method 1) The compound (I-1) in which R ³ in the compound (I) is represented by a hydrogen atom is usually synthesized as shown below, using the compound (II) as a raw material and the compound (II)
The reaction with I) is carried out in a solvent, but can also be carried out by heating and reacting without a solvent. Since the compound XH is eliminated in this reaction, the reaction is preferably performed in the presence of a base in order to capture and smoothly react the compound XH.

[0035]

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Wherein R ¹ , R ² , R ⁴ , m, n and X
Has the same meaning as described above. The solvent is not particularly limited as long as it does not directly participate in the reaction.
Benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene,
Chlorinated or unchlorinated aromatic, aliphatic and alicyclic hydrocarbons such as dichlorobenzene, methylene chloride, chloroform, dichloromethane, dichloroethane, trichloroethylene, cyclohexane; diethyl ether, tetrahydrofuran, dioxane, etc. Ethers; ketones such as acetone, methyl ethyl ketone; alcohols such as methanol, ethanol, ethylene glycol and the like; and hydrates thereof; amides such as N, N-dimethylformamide, N, N-dimethylacetamide , Triethylamine, pyridine,
Organic bases such as N, N-dimethylaniline and the like;
3-dimethyl-2-imidazolidinone; dimethyl sulfoxide; a mixture of the above-mentioned solvents, and the like.

The amount of the solvent used depends on the amount of the compound (I
The compound (II) can be used in such a manner that the concentration of I) is in the range of 5 to 80% by weight.
Is preferably used in such a manner that the concentration thereof becomes 10 to 70% by weight.

Examples of the base include organic bases such as triethylamine, pyridine, N, N-dimethylaniline; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; sodium amide, sodium hydroxide, water Examples thereof include inorganic bases such as potassium oxide, potassium carbonate, sodium carbonate, and sodium hydride.

The amount of the base used is determined by the amount of the compound (I
It can be used in an amount of 0.001 to 5 times the molar amount of I). The reaction temperature is not particularly limited, but is usually -20.
It is in the temperature range below the boiling point of the solvent to be used.
Preferably, it is -20 to 20 ° C. The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be carried out for 0.3 to 24 hours.

The amount of compound (III) to be used is
The compound (III) is used in an amount of 0.5 to 2 moles, preferably 0.8 to 1.5 times the mole of the compound (I). Compound (II) used in the present invention can be prepared, for example, according to the method described in JP-A-2-85263, and the like.
It can be produced using 5-dichloro-6-ethylpyrimidine and the like, and diamine and the like.

As the compound (II), for example,
Compounds (II) [Compounds (II) ₁ to (II) ₁₆ , Compounds (II), each consisting of a substituent corresponding to Compounds 1 to 16, Compounds 21 to 34, and Compounds 42 to 50 shown in 7 ₂₁ to (II) ₃₄ , compound (II) ₄₂ to
(II) designated as ₅₀ . For example, the compound (II) ₁
Means that R ^{1 in the} formula represented by the compound (II) is C ₂
H ₅ and R ² are Cl and m is 8. ].

Compound (III) used in the present invention is described, for example, in Org. Synth. , V, p. 709 (1973)
) Can be produced using dialkyl sulfide or the like and chlorine.

As the compound (III), for example, Table 1
Compounds (III) [Compounds (III) ₁ to (II) comprising the types of substituents corresponding to Compounds 1 to 16, Compounds 21 to 34 and Compounds 42 to 50 shown in
I) ₁₆ , compounds (III) ₂₁ to (III) ₃₄ , and compounds (III) ₄₂ to (III) ₅₀ . For example, the compound (III) ₁ means that in the formula represented by the compound (III), X is a leaving group, R ⁴ is CH ₃ , and n is 2
Means that ].

(Production Method 2) The synthesis of compound (I) is usually carried out in the same manner as in Production Method 1, except that compound (IV) is used in place of compound (II) as a starting material and compound (I) The reaction is carried out in a solvent using compound (V) instead of III), but the reaction can also be carried out by heating without solvent. In this reaction, the compound XH is also eliminated. In order to capture the compound XH and make it react smoothly,
The reaction is preferably performed in the presence of a base.

[0045]

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(Where R ¹ , R ² , R ³ , R ⁴ , m, n
And X are as defined above. ) As the solvent and base used in this reaction, those described in Production method 1 can be mentioned.

The amount of the solvent used depends on the amount of the compound (I
The compound (IV) can be used such that the concentration of V) is in the range of 5 to 80% by weight.
Is preferably used in such a manner that the concentration thereof becomes 10 to 70% by weight. The amount of the base used is the same as that of the compound (IV)
Can be used in an amount of 0.001 to 5 times the molar amount of

The reaction temperature is not particularly limited.
The temperature is within the temperature range from room temperature to the boiling point of the solvent to be used, but it is preferable to heat at a temperature not higher than the boiling point of the solvent in order to shorten the reaction time. The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be carried out for 0.3 to 24 hours.

The amount of compound (V) used is the same as that of compound (IV)
The compound (V) is 0.5 to 2 moles, and preferably 0.8 to 1.5 moles relative to the compound (V).

Compound (IV) used in the present invention is described, for example, in J. Am. Am. Chem. Soc. , 77, 3478
4,5- according to the method described on page (1955) and the like.
It can be produced using dihydroxy-6-ethylpyrimidine and the like and phosphorus oxychloride.

As the compound (IV), for example,
7, each compound (IV) [compound (IV) _1- (I
V) _{Called 50} . For example, the compound (IV) ₁ is a compound represented by the formula (IV) wherein R ¹ is C ₂ H
_5, ^{R 2} means that Cl, X is a leaving group. ]
Can be mentioned.

The compound (V) used in the present invention is, for example,
It can be produced using an alkylsulfonyl chloride or the like and a diamine.

As the compound (V), for example, Tables 1 to 7
Each compound (V) [compound (V) ₁ to (V) _50] consisting of each type of substituent corresponding to compounds 1 to 50 shown therein. For example, the compound (V) ₁ means that R ^{3 in the} formula represented by the compound (V) is H, R ⁴ is CH ₃ ,
It means that m is 8 and n is 2. ] Can be mentioned.

(Production Method 3) In compound (I), R ³ is an alkylsulfonyl group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, or an alkylsulfinyl having 1 to 6 carbon atoms. (I-2) represented by a group
Is synthesized in the same manner as in Production Method 1, as shown below, usually using compound (I-1) instead of compound (II) as a raw material.
And using compound (II) instead of compound (III)
The reaction is carried out in a solvent using I '), but it can also be carried out by heating and reacting without a solvent. Since the compound XH is also eliminated in this reaction, it is preferable to react in the presence of a base in order to capture and react smoothly.

[0055]

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Wherein R ¹ , R ² , R ⁴ , R ⁵ , m,
n, n 'and X are as defined above. ) As the solvent and base used in this reaction, those described in Production method 1 can be mentioned.

The amount of the solvent used depends on the amount of the compound (I
The compound (I-) can be used in such a manner that the concentration of -1) is in the range of 5 to 80% by weight.
It is preferred that the concentration of 1) is 10 to 70% by weight. The amount of the base used is determined by the amount of the compound (I
It can be used in an amount of 0.001 to 5 times the molar amount of -1).

The reaction temperature is not particularly limited.
The temperature is in the range of -20 ° C to the boiling point of the solvent used or lower, but preferably -20 to 20 ° C. The reaction time is
It varies depending on the concentration and temperature, but is usually 0.3 to 2
It can be done in 4 hours.

Compound (III ') is used in an amount of 0.5 to 2 moles, preferably 0.8 to 1.5 moles, relative to Compound (I-1). It is good.

The compound (I-1) used in the present invention can be obtained, for example, by the above-mentioned production method 1. Compound (I-
As 1), for example, compound 17 shown in Tables 1 to 7
To each of the compounds (I-1) [compounds (I-1) ₁₇ to (I-
1) ₂₀ and compounds (I-1) ₃₅ to (I-1) ₄₁ . For example, the compound (I-1) ₃₅ is a compound represented by the formula (I-1) wherein R ¹ is C ₂ H ₅ , R ²
Means Cl, R ⁴ is CH ₃ , m is 8, and n is 2. ].

Compound (III ') used in the present invention is described, for example, in J. Am. Am. Chem. Soc. , 90, 207
According to the method described on page 5 (1968) and the like, it can be produced using dialkyl sulfide and the like and sulfuryl chloride.

As the compound (III ′), for example, each compound (III ′) [compound (III ′) consisting of each substituent type corresponding to compounds 17 to 20, 35 to 41 shown in Tables 1 to 7 ) _17- (III ′) ₂₀ , compound (I)
II ′) ₃₅ to (III ′) ₄₁ . For example, the compound (III ′) ₁ means that R ^{5 in the} formula represented by the compound (III ′) is CH ₃ , n ′ is 2, and X is a leaving group. ].

After completion of the reaction, the target compound (I) produced as described above is subjected to ordinary post-treatments such as extraction, concentration and filtration, and if necessary, recrystallization and various chromatographic techniques. Can be appropriately purified by the above-mentioned means.

As the compound (I) synthesized by the above-mentioned production methods 1 to 3, for example, compounds 1 to 50 shown in Tables 1 to 7 [for example, compound 1 is a compound represented by the formula shown by compound (I) R ¹ is C ₂ H ₅ , R ² is Cl, R ³ is H,
It means that R ⁴ is CH ₃ . ].

Examples of pests that are effective in controlling compound (I) include agricultural and horticultural pests (eg, Hemiptera (hoppers, leafhoppers, aphids, whiteflies, etc.),
Lepidoptera (Coleoptera, Scarabaeidae, Coleoptera, Pests, Scarab beetles, Pieris beetle, etc.), Coleoptera (Tenebrionidae, Weevil, Chrysomelidae, Scarabaeidae, etc.) Family pests), sanitary pests (e.g., flies, mosquitoes, cockroaches, etc.), stored pests (e. G. And agricultural and horticultural pathogens (for example, wheat rust, barley powdery mildew, cucumber downy mildew, rice blast, tomato late blight, etc.).

The pesticidal composition of the present invention has a remarkable insecticidal property.
Compound (I) having acaricidal, bactericidal and nematicidal effects
As an active ingredient. The compound (I) can be used alone, but it is usually compounded with a carrier, a surfactant, a dispersant, an auxiliary agent and the like (for example, powder, emulsion, fine granule, granule, hydrate) by an ordinary method. Prepared as a composition such as an agent, an oily suspension, or an aerosol)
It is preferable to use them.

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 hydrocarbons 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, dimethyl sulfoxide, etc.), water, etc .; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection) out and the like.

Examples of surfactants and dispersants which can be used to improve the performance of this agent, such as adhesion to animals and plants, improvement in absorption, dispersion, emulsification, and spreading of drugs, include, for example, alcohol sulfates and alkyls. Sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like can be mentioned. In order to improve the properties of the preparation, for example, carboxymethylcellulose, polyethylene glycol, gum arabic and the like can be used as an auxiliary agent.

In the preparation of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary can be used alone or in appropriate combination, respectively, according to the respective purposes.
When the compound (I) of the present invention is formulated, the concentration of the active ingredient is usually from 1 to 50% by weight in the emulsion, and usually from 0.3 to 0.3 in the powder.
25 to 25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, 0.5 to 5% by weight for oils and 0.1 to 5% by weight for aerosols. is there.

These preparations can be used for various purposes by diluting them to an appropriate concentration and spraying them on the foliage of plants, soil, or the water surface of paddy fields according to the respective purposes.

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the present invention will be specifically described below.
Note that these examples do not limit the scope of the present invention. Example 1 [Synthesis of Compound (I)]

(1) 5-chloro-6-ethyl-4- (8
Synthesis of -Methanesulfonylamino-octylamino) pyrimidine (Compound 1) The target compound was synthesized by Production Method 1. 5-chloro-
6-ethyl-4- (8-aminooctylamino) pyrimidine (2.8 g) and triethylamine (1.5 ml)
Was dissolved in tetrahydrofuran (40 ml), cooled to 0 ° C., and stirred with methanesulfonyl chloride (1.3).
g) was added dropwise. After the dropwise addition, the mixture was stirred at the same temperature for 1 hour.

After the reaction was completed, tetrahydrofuran was distilled off under reduced pressure, and then the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained oil was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
(2: 1 elution) to obtain 3.2 g of the target compound as a colorless powder.

(2) 5-chloro-6-ethyl-4- (1
Synthesis of 0-methanesulfonylamino-decylamino) pyrimidine (Compound 4) The target compound was synthesized by Production Method 2. 10-methanesulfonylamino-decylamine (2.8 g) and triethylamine (1.7 ml) were added to acetonitrile (50 m).
l) and 4,5-dichloro-6-ethylpyrimidine (1.8 g) was added dropwise with stirring. After the completion of the dropwise addition, the mixture was heated under reflux for 2 hours.

After completion of the reaction, acetonitrile was distilled off from the reaction solution under reduced pressure, and the target compound was extracted with ethyl acetate. The obtained oil was purified by column chromatography (Wakogel C-200, toluene: ethyl acetate = 2: 1 elution) to obtain 3.6 g of a colorless powdery target compound.

(3) 5-chloro-6-ethyl-4-
Synthesis of {(8-N, N-dimethylsulfonylamino) -octylamino} pyrimidine (Compound 35) The target compound was synthesized by Production Method 3. The compound (1.8 g) synthesized in the above (1) was added to tetrahydrofuran (5
0 ml), 60% sodium hydride (0.42 g) was added with stirring, and the mixture was stirred at room temperature for 30 minutes. Next, methanesulfonyl chloride (1.2 g) was added dropwise, and the mixture was heated under reflux for 2 hours.

After completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, then the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. The obtained oil was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
(3: 1 elution) to give 1.9 g of the target compound as a colorless oil.

(4) Synthesis of Other Target Compounds in Tables 1 to 7 Other target compounds shown in Tables 1 to 7 were synthesized according to the production methods of the above (1) to (3).

[0078]

[Table 1]

[0079]

[Table 2]

[0080]

[Table 3]

[0081]

[Table 4]

[0082]

[Table 5]

[0083]

[Table 6]

[0084]

[Table 7]

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 ligninsulfonate were uniformly mixed, then kneaded by adding a small amount of water, 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 (trade name) Name; manufactured by Kao Corporation)
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 Chemical Industries) was added, mixed uniformly, and dissolved to obtain an emulsion. .

(4) Preparation of powder 5 parts by weight of compound 1, 50 parts by weight of talc and kaolin 4
5 parts by weight were uniformly mixed to obtain a powder.

Example 3 [Efficacy test] (1) Efficacy test on adult female spider mites: Compound (I) shown in Tables 1 to 7 prepared according to Example 2
Each wettable powder in water containing a surfactant (0.01%)
Each bean leaf (20 m in diameter) diluted to 00 ppm and infested with 10 adult female spider mites in each of these chemicals.
m) for 15 seconds. Next, each leaf piece was left in a constant temperature room at 25 ° C., and after 3 days, the number of live and dead insects in each leaf piece was counted to determine the acaricidal rate. Evaluation of the acaricidal effect
Four stages (A: 100%, B:
99-80%, C: 79-60%, D: 59% or less). Table 8 shows the results.

[0090]

[Table 8]

(2) Efficacy test against sweet potato nematode Compound (I) prepared according to Example 2 and shown in Tables 1 to 7
Each wettable powder in water containing a surfactant (0.01%)
ppm and the second stage larvae of 100 sweet potato nematodes in each of these chemicals (within 24 hours of hatching)
Released. Next, it was left in a constant temperature room at 25 ° C., and two days later, the number of live and dead insects was counted under a microscope (40-fold visual field) to determine the nematicidal rate. The nematicidal effect was evaluated in four stages (A: 100%, B: 99 to 8) depending on the range of the nematicidal rate.
0%, C: 79 to 60%, D: 59% or less).
Table 9 shows the results.

[0092]

[Table 9]

(3) Wheat Rust Control Efficacy Test (Preventive Effect) Wheat (cultivar: Kobushi wheat) was grown 10 per pot in a plastic flower pot having a diameter of 6 cm. Each wettable powder of the compound (I) shown in Tables 1 to 7 prepared according to Example 2 was added to a surfactant (0.01
%), And diluted with water to 500 ppm, and these chemicals were sprayed at 20 ml per pot. These were cultivated in a glass greenhouse for 2 days, and then a spore suspension of wheat leaf rust (7 × 10 ⁴ spores / ml) was uniformly spray-inoculated on the plant. Next, these were grown in a glass greenhouse for one week, and the degree of wheat rust spots appearing on each first leaf was investigated.

The evaluation of the bactericidal effect was carried out in six stages (0: the whole diseased, 1: the lesion area was about 60%, 2: the lesion area was about 40%, as compared with the degree of the lesion in the untreated plot. 3: The lesion area is about 20%, 4: The lesion area is 10% or less, 5: No lesion). Table 10 shows the results.

[0095]

[Table 10]

(4) Test for controlling efficacy against barley powdery mildew (preventive effect) 10 barleys (cultivar: black wheat) were grown in plastic flower pots having a diameter of 6 cm per pot, and seedlings at the 1.5 leaf stage were produced. Each of the wettable powders of the compounds (I) shown in Tables 1 to 7 prepared according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%). The chemical was sprayed at a rate of 20 ml per pot. These were cultivated in a glass greenhouse for 2 days, and then barley powdery mildew spores were collected from the diseased leaves and sprinkled evenly over each plant for inoculation. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew spots that appeared on each first leaf was investigated. These results are shown in Table 11 by the six-step evaluation method described in the above (3).

[0097]

[Table 11]

(5) Test for controlling efficacy against rice blast (preventive effect) Ten rice plants (variety: Nipponbare) were grown per pot in a plastic flower pot having a diameter of 6 cm. Each wettable powder of the compound (I) shown in Tables 1 to 7 prepared according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%), and 20 ml per pot was diluted. Sprayed. After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then the leaves of the conidia of rice blast prepared from the diseased leaves were uniformly spray-inoculated onto the plant leaves. 28 days after inoculation for 5 days
The plants were grown in a humidity chamber at ℃ and the degree of rice blast lesions on the leaves was investigated. The results are shown in Table 12 using the six-step evaluation method described in (3) above.

[0099]

[Table 12]

(6) Test for controlling efficacy against cucumber downy mildew One cucumber (cultivar: Sagami Hanshiro) per pot was grown in a plastic flower pot having a diameter of 6 cm, and the seedlings were grown on a 1.5-leaf seedling. A wettable powder prepared according to Example 2 from the target compound (I) shown in Examples 1 to 7 was treated with a surfactant (0.01
%) To 40 ppm with water containing
ml. After spraying, grow in a glass greenhouse for 2 days,
Next, the cucumber downy mildew (Pseudoperon)
Ospora cubensis) zoospores were prepared from diseased leaves and sprayed evenly on the underside of plant leaves. After inoculation, keep in the dark at 20 ° C for 2 days, then 5
The plants were grown in a glass greenhouse for days and the degree of cucumber downy spots on the first leaf was investigated. These results are shown in Table 13 by the six-step evaluation method described in the above (3).

[0101]

[Table 13]

[0102]

The novel alkylaminopyrimidine compounds of the present invention are useful agricultural chemicals as pesticides.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code Agency reference number FI Technical indication location C07D 239: 00) (72) Inventor Hirohito Tokunaga 5 Ube Kosan, 1978 Kogushi, Oji, Ube City, Yamaguchi Prefecture Shinichi Naito, Examiner at Ube Research Institute, Inc.

Claims (4)

(57) [Claims] (1) The following formula: (Wherein, R ¹ and R ² independently represent 1 to 6 carbon atoms.
R ³ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
To six haloalkyl group, an alkylsulfonyl group having 1 to 6 carbon atoms, 1-6 alkylthio group carbon atoms, or represents a C 1 -C 6 alkylsulfinyl group; R ₄ is a carbon atom An alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, an alkenyl group having 2 to 6 carbon atoms, and a carbon atom number Represents an alkynyl group having 2 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, or a cycloamino group having 2 to 10 carbon atoms; m represents an integer of 1 to 20; Represents an integer. ) An alkylaminopyrimidine compound represented by the formula: 2. The following formula: (Wherein R ¹ , R ² and m are as defined in claim 1) and a compound represented by the following formula: (Wherein R ⁴ and n are as defined in claim 1; X
Represents a leaving group. The method for producing an alkylaminopyrimidine compound represented by the formula (I), wherein R ³ is a hydrogen atom. 3. The following formula: (Wherein R ¹ and R ² are as defined in claim 1;
X has the same meaning as in claim 2. And a compound represented by the following formula: (Wherein R ³ , R ⁴ , m and n have the same meanings as in claim 1), and are reacted with the compound represented by the formula (I). A method for producing an alkylaminopyrimidine compound. 4. A pesticidal composition comprising an alkylaminopyrimidine compound represented by the formula (I) according to claim 1 as an active ingredient.