JP3511729B2 - 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative, its production method and pesticide for agricultural and horticultural use - Google Patents

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino which is a pesticide for agricultural and horticultural use which is useful as an insecticide, acaricide, fungicide and the like. ] It relates to a pyrimidine derivative.

[0002]

Description of the Prior Art As a 4-aminopyrimidine derivative similar to the present invention, WO92 / 08704 (P.
The following formula disclosed in CT)

[0003]

[Chemical 13]

[In the formula, Q represents a substituent shown in Table 1. A
Is R¹C optionally substituted with₁To C_FiveArche of
Group or C₃~ C_FiveRepresents a cycloalkylene group of
Represents O or S; X represents Si or Ge; R¹Is C₁
Or C₂Haloalkyl group, CN group, C (O) R⁸, C
O₂R⁸, C (O) N (R⁸) R⁹, N₃, NO₂, N
(R⁸) R⁹, N (R⁸) C (O) R⁹, N (R⁸) C
(O) N (R^Ten) R⁹, N (R⁸) S (O)₂R^Ten, O
R⁸, OC (O) R⁸, OCO₂R⁸, OC (O) N
(R⁸) R⁹, OS (O)₂R⁸, SR⁸, S (O) R
⁸, S (O)₂R⁸And SCN; R²Is H, halo
Gen atom, C₁~ C_FourAlkyl group or C₁~ C_FourHa
Represents a lower alkyl group; R₃Is H, halogen atom, C₁~
C₆Alkyl group of C₁~ C₆Haloalkyl group, C₂
~ C₆Alkoxyalkyl group or C ₂~ C₆The archi
Represents a ruthioalkyl group; R^FourIs a halogen atom, C₁~
C₆Alkyl group of C₁~ C₆Haloalkyl group, C₂
~ C₆Alkoxyalkyl group or C₂~ C₆The archi
Represents a ruthioalkyl group; R^FiveIs H, HCO, C₂~ C
₆An alkoxyalkyl group of C₂~ C₆Alkylcal
Bonyl group, C₂~ C₆Alkoxycarbonyl group of C₂
~ C₆Haloalkoxycarbonyl group, COR¹⁵, R¹¹
OC (O) N (R¹²) S-, R¹¹(R¹²) NS- or S
R⁸Represents; R⁶Is H, C₁~ C₆Alkyl group of C₁
~ C₆Alkoxy group of C₂~ C₆The alkoxy alk
Lu group, C₂~ C₆Alkenyl group of C₂~ C₆Halo a
Lucenyl group, C₂~ C₆An alkynyl group of C₂~ C₆of
Alkenyloxy group, C₂~ C₆Alkynyloxy
Base, C₃~ C₆Cycloalkyl group, C₃~ C₆Shiku
Lower alkyl group, C₁~ C₆An alkylthio group of
C₁~ C₆An alkylsulfinyl group of C₁~ C₆The al
Killsulfonyl group, C₁~ C₆A haloalkylthio group of
C₁~ C₆A haloalkylsulfini group, C₁~ C₆of
Even if it is substituted with a haloalkylsulfonyl group and a substituent W
Represents a good phenyl group; R⁷Is H, halogen, CN, N
O₂, C₁Or C₂Alkyl group, C₁Or C₂Arcoki
Si group or CF₃Represents; R⁸And R^TenAre independent of each other
C₁~ C₆Alkyl group of C₁~ C₆The halo archi
Lu group, C₂~ C₆Alkenyl group of C₂~ C₆Halo a
Lucenyl group, C₂~ C₆An alkynyl group of C₃~ C₆of
Haloalkynyl group, C₂~ C₆Alkoxyalkyl
Base, C₂~ C₆An alkylthioalkyl group of C₂~ C₆
Nitroalkyl group, C₂~ C₆A cyanoalkyl group of
C₃~ C₆An alkoxycarbonylalkyl group of C₃~
C₆Cycloalkyl group, C₃~ C₆Halo cycloal
Kill group, a phenyl group which may be substituted with a substituent W or a group
Represents a benzyl group which may be substituted with a substituent W; R⁹Is H
Or C₁~ C_FourRepresents an alkyl group of R;⁸And R⁹And with-
(CH₂)_Four-,-(CH₂)_Five-Or-CH₂CH₂
OCH₂CH₂Represents-; R¹¹And R¹²Independent of
And then C₁~ C_FourRepresents an alkyl group of R;¹³Is C₁~ C
_FourAlkyl group of C₁~ C_FourAlkoxyalkyl group of
Represents a phenyl group which may be substituted with a substituent W; R¹⁴
Is C₁~ C₆Alkyl group of C₁~ C ₆The alkoxy
Base, C₁~ C₆Haloalkoxy groups or 1 to 3 substitutions
Substituted with a phenyl group which may be substituted with a group W or a substituent W
Represents an optionally substituted benzyl group; R¹⁵Is imidazole
1-yl group, pyrazol-1-yl group, 1,2,3-to
Lyazol-1-yl group and 1,2,4-triazole
Represents a -1-yl group; W is a halogen atom, CN, N
O₂, C₁Or C₂Alkyl group of C₁Or C₂The halo
Alkyl group, C₁Or C₂Alkoxy group of C₁Or C
₂Haloalkoxy group, C₁Or C₂Alkylthio
Base, C₁Or C₂Haloalkylthio group, C₁Or C₂
Alkylsulfonyl group or C₁Or C₂The halo archi
Represents a sulfonyl group. It should be noted that the various devices defined by this formula
The symbol of the substituent is limited to this formula only. )

[0005]

[Table 1]

It is described that the compound represented by the formula (1) is effective as an insecticide, acaricide and fungicide. However, the disclosure of a 4-aminopyrimidine derivative having a 2,2,2-trifluoroethoxy group or a trifluoromethoxy group as a substituent of the 2-phenethylamino group moiety as in the present invention is not recognized. Therefore, the 4- [2 of the present invention
Since the-(trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative is a novel compound, it is also known to have pest control activity for agricultural and horticultural use which is useful as an insecticide, acaricide, fungicide, etc. Absent.

[0007]

The object of the present invention is to provide a novel 4-
To provide a [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative, a process for producing the same, and a pesticide for agricultural and horticultural use which is useful as an insecticide, acaricide, bactericide, etc., containing the same as an active ingredient. Is.

[0008]

Means for Solving the Problems As a result of investigations for solving the above problems, the present inventors have found that a novel 4-aminopyrimidine derivative is useful as an insecticide, acaricide, fungicide, etc. in agriculture and horticulture. The inventors have found that the pest control agent has a remarkable control activity as a pest control agent, and have completed the present invention. That is, the present invention is as follows. The first invention is represented by the following formula (1):

[0009]

[Chemical 14]

(Wherein R ¹ represents a halogen atom, a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R ³ represents hydrogen. An atom, an alkyl group having 1 to 4 carbon atoms, an aliphatic acyl group having 2 to 5 carbon atoms, an imidazolecarbonyl group or a pyrazolecarbonyl group, m represents 0 or 1, and n represents 1
Or represents 2. ) Is a 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative. The second invention is the following formula (2):

[0011]

[Chemical 15]

(Wherein R ¹ has the same meaning as defined above) and a pyrimidine derivative represented by the following formula (3-1):

[0013]

[Chemical 16]

(Wherein R ² , m and n have the same meanings as defined above), and 2-phenethylamines represented by the formula (4) are represented by the above formula (1).
An aminopyrimidine derivative represented by the following formula (1-1) in which R ³ is a hydrogen atom:

[0015]

[Chemical 17]

The present invention relates to a process for producing a pyrimidine derivative represented by the formula (wherein R ¹ , R ² , m and n are as defined above). A third invention is a compound represented by the above formula (1-1) and the following formula (4):

[0017]

[Chemical 18]

(Wherein R ⁴ represents an alkyl group having 1 to ⁴ carbon atoms) is reacted with a lower aliphatic carboxylic acid chloride compound represented by the above formula (1)
A 4-aminopyrimidine derivative represented by the following formula (1-2) in which R ³ is an aliphatic acyl group having 2 to 5 carbon atoms:

[0019]

[Chemical 19]

(Wherein R ¹ , R ² , R ⁴ , m and n are
It is synonymous with the above. ) Concerning the manufacturing method of the pyrimidine derivative shown by these. The fourth invention is the above formula (1-1).
And a pyrimidine derivative represented by the following formula (5):

[0021]

[Chemical 20]

By reacting with trichloromethyl formate represented by the following formula (6):

[0023]

[Chemical 21]

An intermediate represented by the formula (wherein R ¹ , R ² , m and n have the same meanings as described above) is prepared, and then the following formula (7):

[0025]

[Chemical formula 22]

A 4-aminopyrimidine derivative represented by the above formula (1), wherein R ⁵ represents an imidazole group or a pyrazole group, is reacted, and R ³ Is an imidazole group or a pyrazole group, represented by the following formula (1-3):

[0027]

[Chemical formula 23]

(Wherein R ¹ , R ² , m, n and R ⁵ are
It is synonymous with the above. ) Concerning the manufacturing method of the pyrimidine derivative shown by these. The fifth invention is the above-mentioned formula (1-1).
And a pyrimidine derivative represented by the following formula (3-2):

[0029]

[Chemical formula 24]

(In the formula, R ⁶ represents an alkyl group having 1 to 4 carbon atoms; R ² , m and n are as defined above.)
A 4-aminopyrimidine derivative represented by the above formula (1), characterized in that R ³ has 1 to 1 carbon atoms.
The following formula (1-4), which is four alkyl groups:

[0031]

[Chemical 25]

(Wherein R ⁶ , R ¹ , R ² , m and n are
It is synonymous with the above. ) Concerning the manufacturing method of the pyrimidine derivative shown by these. A sixth invention is the above-mentioned formula (1).
The present invention relates to a pest control agent for agricultural and horticultural use containing the 4-aminopyrimidine derivative represented by

The present invention will be described in detail below. Regarding the target compound and the starting material compound A novel 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative [compound (1)], which is the target compound, and its manufacturing raw material [compound (2),
R ^{1 to} R ³ represented by the compound (3-1), the compound (3-2), the compound (4), and the compound (7)] are as follows.

[R ¹ ] Examples of R ¹ include a halogen atom, a hydrogen atom, and an alkoxy group having 1 to 4 carbon atoms. Examples of the halogen atom include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom, and a chlorine atom and an iodine atom are preferable. The alkoxy group, there may be mentioned a straight or branched; preferably a -OCH _3.

[R ² ] Examples of R ² include a hydrogen atom and an alkyl group having 1 to 4 carbon atoms. The alkyl group may be a linear or branched alkyl group; CH ₃ is preferable. n is 1 or 2. If (R ²⁾ R ² is the n alkyl group, n is 1 are preferred; but the substitution position is not particularly limited, it is preferably 3-position.

[R ³ ] Examples of R ³ include a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aliphatic acyl group having 2 to 5 carbon atoms, an imidazolecarbonyl group, and a pyrazolecarbonyl group. The alkyl group may be a linear or branched alkyl group; CH ₃ is preferable. Examples of the acyl group include an acetyl group, a propionyl group, an n-butyryl group, an i-butyryl group, an n-valeroyl group, an i-valeroyl group, a trimethylacetyl group and the like; and an acetyl group is preferable. The imidazolecarbonyl group is preferably an imidazol-1-yl-carbonyl group. The pyrazole carbonyl group is preferably pyrazole-1-
It is an yl-carbonyl group. m is 0 or 1, but is preferably 1.

The compound (1) may be a combination of the above-mentioned various substituents, and preferable compounds from the viewpoint of efficacy are as follows. (a) A compound in which R ¹ is a halogen atom, (R ² ) n and R ³ are hydrogen atoms, and m is 1. (b) A compound in which R ¹ is a halogen atom, (R ² ) n is a hydrogen atom, R ³ is an acyl group having 2 to 5 carbon atoms, and m is 1. (c) A compound in which R ¹ is a halogen atom, (R ² ) n is a hydrogen atom, R ³ is an imidazolecarbonyl group, and m is 1. (d) R ¹ is a halogen atom, (R ² ) n is a hydrogen atom, R ³ is a pyrazole carbonyl group, and m is 1
Is a compound. (e) R ¹ is a halogen atom, (R ² ) n is a hydrogen atom, R ³ is an alkyl group having 1 to 4 carbon atoms, and m
Wherein the compound is 1.

(A) consisting of these preferred combinations
As R ¹ , R ² , m and n of the compound (1) represented by (e) to (e), the preferable ones and more preferable ones shown in the above-mentioned explanation can be exemplified. Specific examples of these compounds (1) include compounds 1 to 6, 9 and 13 described in Tables 2 and 3 below.

Since the compound (1) of the present invention has an amino group, acid addition salts derived from them are also included in the present invention. Examples of acids forming acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid; formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, aconitic acid, etc. Carboxylic acids; organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid; and saccharin.

Compound (1) is prepared by the following synthetic method 1,
It can be synthesized by 2, 3 or 4. [Synthesis Method 1] Compound (1-1) [compound (1) in which R ³ is a hydrogen atom] is prepared by reacting compound (2) and compound (3-1) in a solvent as shown below. It can be produced by reacting. The reaction between the compound (2) and the compound (3-1) can be promoted in the presence of a base.

[0041]

[Chemical formula 26]

(In the formula, R ¹ , R ² , m and n have the same meanings as described above.) The kind of the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include benzene and toluene. Aromatic, aliphatic, alicyclic, chlorinated, such as, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloroethane, trichloroethylene, cyclohexane Hydrocarbons of the formula; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc .; ketones such as acetone, methyl ethyl ketone, etc .; N, N-dimethylformamide,
Amides such as N, N-dimethylacetamide;
Nitriles such as acetonitrile and propionitrile; organic bases such as triethylamine, pyridine, N, N-dimethylaniline; 1,3-dimethyl-2
-Imidazolidone; dimethylsulfoxide; mixtures of the solvents mentioned.

The solvent is used in an amount of 5 to 80 for the compound (2).
It can be used by making it to be a weight%; 10
˜70 wt% is preferred. The type of base is not particularly limited, and examples thereof include triethylamine, pyridine, N,
Organic bases such as N-dimethylaniline, DBU, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, potassium carbonate, etc. Mention may be made of inorganic bases; organic bases are preferred. The amount of the base used is 0.001 to 5 times by mole with respect to the compound (2); preferably 1.0 to 2 times by mole. The reaction temperature is
Although not particularly limited, it is within a temperature range from room temperature to the boiling point of the solvent used or less; 60 to 110 ° C. is preferable. The reaction time varies depending on the above-mentioned concentration and temperature; it is usually 0.3 to 2 hours.

The amount of the raw material compound used is 0.5 to 2 times mol of compound (3-1) with respect to compound (2); preferably 0.8 to 1.2 times mol. Compound (2) can be obtained, for example, from Journal of Chemical Society (J.
C. S) According to the method described in 3478 to 3481 (1955), it can usually be produced by reacting compound (9) with compound (10) as shown below.

[0045]

[Chemical 27]

(In the formula, R ¹ has the same meaning as described above.) As the compound (2), the compound (2) consisting of each substituent corresponding to the compounds 1 to 15 shown in Tables 2 and 3 below.
[Compounds (2) ₁ to (2) ₁₅ are referred to. For example, in the compound (2) ₁ , R ^{1 in the} formula represented by the compound (2) is a chlorine atom. ]. Compound (3-
1) can be manufactured as follows.

[0047]

[Chemical 28]

(In the formula, R ² , m and n have the same meanings as described above.) As the compound (3-1), each substitution corresponding to the compounds 1 to 15 shown in Tables 2 and 3 below. Compound consisting of a group (3-1)
[Compounds (3-1) ₁ to (3-1) ₁₅ are referred to. For example, in compound (3-1) ₁ , (R ² ) n in the formula represented by compound (3-1) is a hydrogen atom, and m is 1. ]. The target compound (1
After completion of the reaction, -1) is subjected to usual post-treatments such as extraction, concentration and filtration, and can be appropriately purified by a known means such as recrystallization and various chromatography if necessary. Examples of the compound (1-1) include compounds 1, 7 to 11 shown in Tables 2 and 3 below.

[Synthesis Method 2] Compound (1-2) [wherein R ³ in the compound (1) has 2 to 2 carbon atoms]
The compound having five aliphatic acyl groups] can be produced by reacting the compound (1-1) with the compound (4) in a solvent or without a solvent, as shown below. This reaction can be accelerated in the presence of a base.

[0050]

[Chemical 29]

(Wherein R ¹ , R ² , R ⁴ , m and n are
It is synonymous with the above. ) As the type of solvent, in addition to the solvent described in the method of synthesizing compound (1-1), anhydrides of aliphatic carboxylic acids such as acetic anhydride, propionic anhydride, butanoic anhydride, and mixtures thereof An anhydride of the same aliphatic carboxylic acid as the acyl group to be introduced is preferable.

The solvent is used in an amount of 5 to 80 for the compound (1-1).
It can be used by making it to be a weight%; 10
˜70 wt% is preferred. Examples of the base include the bases described in Synthesis Method 1; organic bases are preferred. The amount of base used is 1 to 5 with respect to compound (1-1).
It is twice the mole; however, it is preferably 2 to 5 times the mole. The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used; 80 to 120 ° C. is preferable.
The reaction time varies depending on the above-mentioned concentration and temperature; it is usually 2 to 10 hours. As the compound (4), a commercially available product can be used.

Target compound produced as described above
After completion of the reaction, (1-2) can be subjected to usual post-treatments such as extraction, concentration and filtration, and if necessary, it can be appropriately purified by a known means such as recrystallization and various chromatography.
Examples of the compound (1-2) include compounds 2 to 4 and 12 shown in Tables 2 and 3 below.

[Synthesis Method 3] Compound (1-3) [Compound (1) wherein R ³ is an imidazolecarbonyl group or a pyrazolecarbonyl group] is a compound (1-1) (5)
And are reacted in a solvent to synthesize an intermediate compound (6),
Then, it can be produced by reacting compound (7). The reaction between compound (6) and compound (7) can be promoted in the presence of a base.

[0055]

[Chemical 30]

(Wherein R ¹ , R ² , R ⁵ , m and n are
It is synonymous with the above. ) Examples of the solvent include the solvents described in the method of synthesizing compound (1-1); aromatic hydrocarbons such as toluene are preferable. The amount of the solvent used is 5 to 5 for the compound (1-1).
It can be used in an amount of 80% by weight;
10 to 70% by weight is preferable. Examples of the type of base include the bases described in the synthetic method (1-1), but organic bases such as pyridine and triethylamine are preferable. The amount of the base used is 1 to 5 times mol, preferably 2 to 5 times mol, of the compound (1-1).

The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used; room temperature to
50 ° C is preferred. The reaction time varies depending on the above-mentioned concentration and temperature; it is usually 0.5 to 1 hour. As the compound (5) and the compound (7), commercially available products can be used. Target compound (1-3) produced as described above
After completion of the reaction, usual post-treatments such as extraction, concentration and filtration can be carried out, and if necessary, it can be appropriately purified by a known means such as recrystallization and various chromatography. Compound
Examples of (1-3) include compounds 5 and 6 shown in Table 2 below. The desired compound (1-3) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after the completion of the reaction, and if necessary, known recrystallization, various chromatographic methods, etc. It can be appropriately purified by means.

[Synthesis Method 4] Compound (1-4) [R ³ in compound (1) has 1 to 1 carbon atoms]
Compounds that are four alkyl groups] are as follows:
It can be produced by reacting compound (2) with compound (3-2) in a solvent. The reaction between the compound (2) and the compound (3-2) can be promoted in the presence of a base.

[0059]

[Chemical 31]

(Wherein R ¹ , R ² , R ⁶ , m and n are
It is synonymous with the above. ) Examples of the solvent include the solvents described in the method for synthesizing compound (1-1); amides such as N, N-dimethylformamide are preferable. The amount of the solvent used may be 5 to 80% by weight of the compound (2); preferably 10 to 70% by weight. Examples of the type of base include the bases described in the synthetic method (1-1), but organic bases such as pyridine and triethylamine are preferable. The amount of the base used is 1 to 5 times mols of the compound (2); preferably 2 to 5 times mols.

The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used; 60 to
110 ° C is preferred. The reaction time varies depending on the above concentration and temperature; it is usually 0.5 to 2 hours. The amount of the raw material compound used is 0.5 to 2 times mol of the compound (3-2) with respect to the compound (2); preferably 0.8 to 1.2.
It is twice the mole. Compound (3-2) can be produced as shown below.

[0062]

[Chemical 32]

(In the formula, R², R⁶, M and n are as described above.
Are synonymous. ) As the compound (3-2), the compound 1 shown in Table 3 below is used.
Compounds (3-2) consisting of each substituent corresponding to 3 to 15 are listed.
Can be obtained [Compound (3-2)₁₃~ (3-2)₁₅Call
It For example, compound (3-2)₁₃Is represented by compound (3-2)
(R ²) N is a hydrogen atom and m is 1.
R⁶Is CH₃Is. ]. Manufactured as above
The target compound (1-4) was extracted, concentrated,
Perform normal post-treatment such as filtration, recrystallize if necessary,
Appropriately purify by known means such as various chromatography.
You can The compound (1-4) is shown in Table 3 below.
The compound 13 shown in can be mentioned.

Pest control agent for agricultural and horticultural use [controlling effect] As a pest in agricultural and horticultural activities which is recognized to have a controlling effect by the compound (1) of the present invention, there are agricultural and horticultural pests [eg, Hemiptera (Plantains, leafhoppers). Aphids,
Whiteflies, etc.), Lepidoptera (Beetle beetles, diamondback moth,
Leaf beetles, leaf moths, hornworms, butterflies, etc.), Coleoptera (Galloridae, Weevil),
Chrysomelidae, chafers, etc.), mites (such as citrus mites of the mite family, citrus spider mites of the mite family, etc.)], hygiene pests (eg, flies, mosquitoes, cockroaches), stored-product pests (Scots beetles, weevil) ), Root-knot nematodes in the soil, pine wood nematodes, mite, etc., and agricultural and horticultural pathogens (eg, wheat red rust, barley powdery mildew, cucumber downy mildew, rice blast, tomato blight). Can be mentioned.

[Pest Control Agent] The pest control agent for agricultural and horticultural use of the present invention has particularly remarkable insecticidal, acaricidal, bactericidal, and nematicidal effects, and one or more compounds (1) are effective. It is contained as an ingredient. The compound (1) can be used alone, but is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent and the like by a conventional method (eg, powder, emulsion, fine granule, granule, hydrate). It is preferably prepared as a composition such as an agent, an oily suspension, or an aerosol).

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

Surfactants and dispersants that can be used to improve the performance of this agent such as adhesion to animals and plants, improvement of absorption, dispersion of drug, emulsification, spreading, and the like include, for example, alcohol sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic or the like can be used as an auxiliary agent. In the production of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in appropriate combination according to the purpose. The concentration of the active ingredient when the compound (I) of the present invention is formulated is usually 1 to 50% by weight for emulsions, 0.3 to 25% by weight for powders, and usually 1 to 90% for wettable powders.
% By weight, usually 0.5 to 5% by weight for granules, 0.5 to 5% by weight for oils, and usually 0.1 to 5% by weight for aerosols. These formulations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, water surface of paddy field or directly applied to various applications depending on the purpose.

[0068]

EXAMPLES The present invention will be specifically described below with reference to examples and examples. It should be noted that these examples do not limit the scope of the present invention. Reference Example 1 [Synthesis of Compound (2)] (1) Synthesis of 4-chloro-6-ethyl-5-methoxypyrimidine 6-Ethyl-5-methoxy-4-hydroxypyrimidine (4.0 g) was added to 1,2- Dissolve in dichloroethane (40 ml), add phosphorus oxychloride (8.0 g), and heat to about 80 ° C.
And stirred for 5 hours. The reaction solution was poured into ice water, extracted with chloroform, washed with water, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (Wako Gel C-2
00, toluene elution) to obtain 1.5 g of the desired product as a pale yellow oily liquid.

¹ H-NMR (CDCl ₃ , δppm) 1.10 to 1.16 (t, 3H), 2.66 to 2.74
(Q, 1H), 3.79 (s, 3H), 8.92 (s,
1H)

(2) Synthesis of 4-chloro-5-iodo-6-ethylpyrimidine 6-ethyl-5-iodo-4-hydroxypyrimidine (10.4 g) was dissolved in chloroform (50 ml),
Phosphorus oxychloride (13.7 g) was added, and the mixture was stirred under reflux for about 5 hours. The reaction solution was poured into ice water, extracted with chloroform, washed with water, and dried over anhydrous sodium sulfate. Then
The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (Wakogel C-200, eluted with toluene) to obtain 4.5 g of a target product which was a pale yellow oily liquid.

¹ H-NMR (CDCl ₃ , δppm) 1.21-1.27 (t, 3H), 2.75-2.84
(Q, 1H), 8.79 (s, 1H)

Reference Example 2 [Synthesis of Compound (3-1)] (1) 2- [4- (2,2,2-trifluoroethoxy)
Synthesis of phenyl] ethylamine N- [2- [4- (2,2,2-trifluoroethoxy) synthesized from 2- [4- (2,2,2-trifluoroethoxy) phenyl] ethyl bromide and phthalimido potassium Phenyl] ethyl] phthalimide (5.4 g) was dissolved in ethanol (50 ml) by heating, hydrazine hydrate (2 ml) was added, and the mixture was stirred for 2 hours. Then, the mixture was made strongly acidic with dilute hydrochloric acid, the precipitated crystals were filtered off, and the crystals were thoroughly washed with water. The filtrate and the washing solution are combined, made alkaline with an aqueous sodium hydroxide solution, the oily substance that separates is extracted with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure to give a pale yellow oily liquid. 3.5 g of the target product of was obtained.

¹ H-NMR (CDCl ₃ , δppm) 2.74-2.91 (m, 4H), 3.50-3.59
(M, 2H), 4.30 to 4.40 (q, 2H), 6.
85-6.87 (d, 2H), 7.14-7.17
(D, 2H)

(2) Synthesis of 2- (4-trifluoromethoxyphenyl) ethylamine Lithium aluminum hydride (3 g) was suspended in dry tetrahydrofuran (100 ml) and stirred. Then, 4-trifluoromethoxybenzyl cyanide (1
3 g) in dry tetrahydrofuran (20 ml),
The mixture was slowly added dropwise while stirring with ice cooling. After the dropping, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was ice-cooled, water (50 ml) was slowly added dropwise, and then a 15% aqueous sodium hydroxide solution (5
0 ml) was added dropwise. The deposited precipitate was filtered through Celite, and the obtained organic layer was concentrated under reduced pressure. The residue was dissolved in toluene, extracted with diluted hydrochloric acid, sodium hydroxide was added to the obtained aqueous layer to make it alkaline, and the separated oil was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 6.3 g of the desired product as a yellow oily substance.

¹ H-NMR (CDCl ₃ , δppm) 2.83 to 3.03 (m, 4H), 3.47 to 3.54
(M, 2H), 7.09 to 7.23 (dd, 4H)

Reference Example 3 [Synthesis of Compound (3-2)] (1) Synthesis of N-methyl-2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamine 2- [4- ( 2,2,2-Trifluoroethoxy) phenyl] ethyl bromide (6 g) was added to a 40% monomethylamine aqueous solution (20 ml), and the mixture was stirred at room temperature for 20 hours. After the reaction was completed, the desired compound was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3.2 g of the desired product as a pale yellow oily liquid.

¹ H-NMR (CDCl ₃ , δppm) 1.60 to 2.25 (m, 1H), 2.62 (s, 3)
H) 2.72 to 2.99 (m, 2H), 3.04 to 3.23.
(M, 2H), 4.18 to 4.45 (m, 2H), 6.
87-6.92 (d, 2H), 7.12-7.20
(D, 2H)

Example 1 [Synthesis of Compound (1)] (1) 5-chloro-6-ethyl-4- {2- [4- (2,
Synthesis of 2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [Compound 1] 2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamine (2.2 g) obtained in Reference Example 2 And triethylamine (3 g) were dissolved in toluene (30 ml), and 4,5-dichloro-6-ethylpyrimidine (1.8
g) was added, and the mixture was heated with stirring at about 60 ° C. for 4 hours. After completion of the reaction, water was added to the reaction mixture, the target compound was extracted with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 3: 1 elution) to obtain 3.3 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.29 (t, 3H), 2.47 to 2.82
(Q, 2H), 2.87 to 2.92 (t, 2H), 3.
70-3.77 (m, 2H), 4.29-4.39
(Q, 2H), 5.29 to 5.50 (m, 1H), 6.
89-6.92 (d, 2H), 7.16-7.19
(D, 2H), 8.44 (s, 1H)

(2) Synthesis of N-acetyl-5-chloro-6-ethyl-4- {2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [Compound 2] 5 -Chloro-6-ethyl-4- {2- [4- (2,2,
2-trifluoroethoxy) phenyl] ethylamino}
Pyrimidine (0.7 g) was dissolved in acetic anhydride (10 ml), pyrimidine (0.4 g) and acetyl chloride (1.0 g) were added, and the mixture was stirred at about 80 ° C. for 24 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added, the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 9: 1 elution) to give 0.55 of the target compound as colorless powdery crystals.
g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.31 to 1.36 (t, 3H), 1.96 (s, 3)
H), 2.84 to 2.90 (t, 2H), 2.95 to
3.03 (q, 2H), 3.96 to 4.02 (t, 2)
H), 4.25 to 4.34 (q, 2H), 6.80 to
6.84 (d, 2H), 7.10 to 7.13 (d, 2)
H), 8.93 (s, 1H)

(3) N-propionyl-5-chloro-6-
Synthesis of ethyl-4- {2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [Compound 3] 5-chloro-6-ethyl-4- {2- [4- ( 2, 2,
2-trifluoroethoxy) phenyl] ethylamino}
Pyrimidine (1.0 g) was converted to propionic anhydride (10 m
1), pyrimidine (0.5 g) and propionyl chloride (0.5 g) were added, and the mixture was stirred at about 80 ° C. for 24 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Wako Gel C-200, toluene: ethyl acetate = 9: 1 elution).
By purifying in (1), 1.0 g of the target compound which is a pale yellow powdery crystal was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.08 to 1.14 (t, 3H), 1.31 to 1.37
(T, 3H), 2.10 to 2.18 (q, 2H), 2.
84-2.90 (t, 2H), 2.95-3.03
(Q, 2H), 3.93 to 3.99 (t, 2H), 4.
25-4.34 (q, 2H), 6.80-6.83
(D, 2H), 7.11 to 7.14 (d, 2H), 8.
93 (s, 1H)

(4) N-imidazol-1-yl-carbonyl-5-chloro-6-ethyl-4- {2- [4-
Synthesis of (2,2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [compound 5] 5-chloro-6-ethyl-4- {2- [4- (2,2,
2-trifluoroethoxy) phenyl] ethylamino}
Pyrimidine (2.2 g) and triethylamine (1 g) were dissolved in toluene (20 ml), trichloromethyl chloroformate (1.1 g) was added dropwise under ice-cooling stirring, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water (20 m
l) was added, the target compound was extracted with toluene, washed with water,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to give an intermediate N-chlorocarbonyl-5-chloro-6-ethyl-4- {2- [4- (2,
2.3 g of 2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine was obtained as a pale yellow oil. This intermediate (1.0 g) and triethylamine (0.2 g)
And were dissolved in toluene (10 ml), imidazole (0.2 g) was added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, water (10 ml) was added, the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (Wako Gel C
-200, toluene: ethyl acetate = 3: 1 eluate) to give the target compound as a pale yellow liquid.
8 g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.23 (t, 3H), 2.78 to 2.86
(Q, 2H), 3.01 to 3.07 (t, 2H), 4.
20-4.26 (m, 2H), 4.27-4.34
(M, 2H), 6.77 to 6.79 (d, 2H), 6.
88-6.89 (m, 2H), 7.12-7.14
(D, 2H), 7.62 (s, 1H), 8.88 (s,
1H)

(5) N-pyrazol-1-yl-carbonyl-5-chloro-6-ethyl-4- {2- [4- (2,
Synthesis of 2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [compound 6] N-chlorocarbonyl-5-chloro-6 obtained in (4)
-Ethyl-4- {2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine (1.0 g) and triethylamine (0.2 g) were dissolved in toluene (10 ml), Pyrazole (0.2 g) was added and stirred at room temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, water (10 ml) was added, the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (Wako Gel C-200, toluene: ethyl acetate = 3: 1 elution) to obtain 0.8 g of the target compound as a pale yellow liquid.

¹ H-NMR (CDCl ₃ , δppm) 1.19 to 1.24 (t, 3H), 2.78 to 2.86
(Q, 2H), 3.03 to 3.09 (t, 2H), 4.
24-4.30 (m, 2H), 4.27-4.33
(M, 2H), 6.29 to 6.31 (m, 1H), 6.
80 to 6.82 (d, 2H), 7.13 to 7.17
(D, 2H), 7.27 to 7.29 (m, 1H), 8.
19 to 8.20 (m, 1H), 8.85 (s, 1H)

(6) 6-Ethyl-4- {2- [4- (2,
Synthesis of 2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [Compound 7] 2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamine (0.5 g) was added to dimethylformamide (10 ml). Was dissolved in, and 4-chloro-6-ethylpyrimidine (0.7 g) and then powdered potassium hydroxide (0.3 g) were sequentially added thereto, and the mixture was stirred at about 60 ° C. for 2 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added, the target compound was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Wako Gel C-20
0, toluene: ethyl acetate = 1: 3 eluate) to give 0.3% of the target compound as a light brown viscous liquid.
8 g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.28 to 1.33 (t, 3H), 2.58 to 2.64
(T, 2H), 2.70 to 2.78 (q, 2H), 3.
90-3.96 (t, 2H), 4.28-4.36
(Q, 2H), 5.51 (broad, 1H), 6.0
2 (s, 1H), 6.79 to 6.83 (d, 2H),
7.09 to 7.13 (d, 2H), 8.43 (s, 1
H)

(7) 6-Ethyl-4- {2- [4- (2,
Synthesis of 2,2-trifluoroethoxy) phenyl] ethylamino} -5-methoxypyrimidine [Compound 8] 2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamine (0.6 g) and triethylamine (0.3 g) was dissolved in dimethylformamide (10 ml), and 4-chloro-6-ethyl-5-methoxypyrimidine (0.8 g) obtained in Reference Example 1 was added thereto, followed by powdered potassium hydroxide (0. 6 g) was added sequentially, and the mixture was stirred at about 60 ° C. for 2 hours. After completion of the reaction, water was added to the reaction mixture, the target compound was extracted with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (Wako Gel C-200, eluted with ethyl acetate: toluene = 1: 3) to obtain 0.3 g of the target compound as a light brown viscous liquid.

¹ H-NMR (CDCl ₃ , δppm) 1.06 to 1.12 (t, 3H), 2.62 to 2.68
(T, 2H), 2.95 to 3.03 (q, 2H), 3.
71 to 3.78 (t, 2H), 3.90 (s, 3H),
3.96 to 4.02 (q, 2H), 5.59 (broa
d, 1H), 6.84 to 6.87 (d, 2H), 7.1
7 to 7.20 (d, 2H), 8.65 (s, 1H)

(8) 6-Ethyl-4- {2- [4- (2,
Synthesis of 2,2-trifluoroethoxy) phenyl] ethylamino} -5-iodopyrimidine [Compound 9] 2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamine (1.3 g) and triethylamine (1.3 g) was dissolved in toluene (20 ml), 4-chloro-6-ethyl-5-iodopyrimidine (1.3 g) obtained in Reference Example 1 was added thereto, and the mixture was stirred at about 80 ° C. for 10 hours. did. After completion of the reaction, water was added to the reaction mixture, the target compound was extracted with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel column chromatography (Wako Gel C-
200, eluted with ethyl acetate: toluene = 1: 3) to give 0.55 of the target compound as light brown crystals.
g was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.15 to 1.23 (t, 3H), 2.63 to 2.72
(T, 2H), 2.94 to 3.01 (q, 2H), 3.
90-3.96 (t, 2H), 4.11-4.18
(Q, 2H), 5.50 (broad, 1H), 6.8
3 to 6.88 (d, 2H), 7.10 to 7.14 (d,
2H), 8.55 (s, 1H)

(9) N-methyl-5-chloro-6-ethyl-4- {2- [4- (2,2,2-trifluoroethoxy) phenyl] ethylamino} pyrimidine [Compound 1
3] Synthesis of N-methyl-2- [4- (2,2,2-
Trifluoroethoxy) phenyl] ethylamine (0.
25 g) and triethylamine (1.0 g) were dissolved in dimethylformamide (10 ml), 4,5-dichloro-6-ethylpyrimidine (0.2 g) was added thereto, and the mixture was stirred at about 60 ° C for 2 hr. After completion of the reaction, water was added to the reaction mixture, the target compound was extracted with toluene, washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography (Wako Gel C-200, toluene: ethyl acetate = 1.
Purification by elution (0: 1) gave 0.16 g of the target compound as a colorless oil.

¹ H-NMR (CDCl ₃ , δppm) 1.24 to 1.32 (t, 3H), 2.80 to 2.90
(Q, 2H), 2.91 to 2.98 (m, 2H), 3.
17 (s, 3H), 3.75 to 3.81 (m, 2H),
4.29-4.38 (m, 2H), 6.88-6.90
(D, 2H), 7.15 to 7.20 (d, 2H), 8.
44 (s, 1H)

(10) Other compounds (1) in Tables 2 and 3
Synthesis of Other compounds (1) in Tables 2 and 3 were synthesized according to the methods described in (1) to (9) above. The compounds synthesized as described above are shown in Tables 2 and 3.

[0097]

[Table 2]

[0098]

[Table 3]

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

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

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

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

Example 3 [Efficacy test] (1) Efficacy test against brown planthopper Each wettable powder of the compound (1) shown in Tables 2 and 3 prepared according to Example 2 was treated with a surfactant (0.01%). Was diluted to 100 ppm with water containing water, rice seedlings were immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. Next, 10 cylindrical brown planthoppers (4th instar larvae) were left in each cylinder, capped with a porous plug, allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the insecticidal rate.
The evaluation of the insecticidal effect was shown in four stages (A: 100%, B: less than 100 to 80%, C: less than 80 to 60%, D: less than 60%) depending on the range of mortality. The comparative compounds 1 and 2 described in WO92 / 08704 (PCT) as shown in Table 4 were examined in the same manner as in the case of the compound (1) and set as comparative examples.

[0104]

[Table 4]

The results are shown in Table 5.

[0106]

[Table 5]

(2) Efficacy test against diamondback moth Each wettable powder of the compound (1) shown in Tables 2 and 3 prepared according to Example 2 was diluted to 300 ppm with water containing a surfactant (0.01%). Then, cabbage leaf pieces (5 × 5 cm) were dipped in each of these chemical solutions for 30 seconds, placed in each plastic cup one by one and air dried. Next, in each of these cups, 10 diamondback moths (third instar larvae) were released, covered, and allowed to stand in a constant temperature room at 25 ° C., and after 2 days, the number of live and dead insects in each cup was counted to determine the mortality rate. I asked. The results of the insecticidal effect evaluation are shown in Table 6 together with the comparative compound described in (1) above in a four-step evaluation method.

[0108]

[Table 6]

(3) Efficacy test against green leafhoppers Each wettable powder of the compound (1) shown in Tables 2 and 3 prepared according to Example 2 was adjusted to 30 ppm with water containing a surfactant (0.01%). Diluted, rice seedlings were immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. Next, 10 green leafhoppers (4th instar larvae) were left in each cylinder, capped with a porous plug, allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the insecticidal rate.
The results of evaluation of the insecticidal effect are shown in Table 7 together with the comparative compound described in (1) above in a 4-step evaluation method.

[0110]

[Table 7]

(4) Efficacy test against Spodoptera litura Each wettable powder of the compound (1) shown in Tables 2 and 3 prepared according to Example 2 was adjusted to 500 ppm with water containing a surfactant (0.01%). The diluted soybeans were soaked with soybean true leaves for 30 seconds, placed in each plastic cup one by one, and air-dried. In each of these cups, 10 Spodoptera litura (2nd instar larvae) were released, covered, and allowed to stand in a constant temperature room at 25 ° C., and two days later, the number of live and dead insects in each cup was counted to determine the insecticidal rate. The results of the evaluation of insecticidal effect are
Along with the comparative compound described in (1), it is shown in Table 8 by a 4-step evaluation method.

[0112]

[Table 8]

(5) Efficacy test against sweet potato root-knot nematodes Each wettable powder of compound (1) shown in Tables 2 and 3 prepared according to Example 2 was diluted to 20 ppm with water. 0.5 ml of this was put into a test tube, and 0.5 ml of a liquid containing 30 to 40 sweet potato root knot nematodes was further put.
Next, it was allowed to stand in a constant temperature room at 25 ° C., and two days later, the number of live and dead insects was counted under a microscope to determine the nematicidal rate. The results of the evaluation of the nematicidal effect are 4 steps (A: 100 to 90%, depending on the range of the nematicidal rate, together with the comparative compound described in (1) above.
B: less than 90 to 80%, C: less than 80 to 60%, D: 6
(Less than 0%). The results are shown in Table 9.

[0114]

[Table 9]

(6) Control Efficacy Test for Wheat Leaf Rust (Preventive Effect) Ten wheat (cultivar: Kobushi Wheat) was grown in a plastic flower pot with a diameter of 6 cm, and 10 seeds were cultivated at 1.5 leaf stage. A wettable powder of the compound (1) shown in Tables 2 and 3 prepared according to Example 2 was mixed with a surfactant (0.01
%) And dilute to 500 ppm with water containing 2% per pot.
Sprayed with 0 ml. After spraying, cultivate in a glass greenhouse for 2 days, and then spore suspension of wheat leaf rust (7 x 10
⁴ spores / ml) were uniformly spray-inoculated on the plants. After inoculation, the seedlings were grown in a glass greenhouse for 1 week, and the degree of wheat leaf rust lesions appearing on the first leaf was investigated. The evaluation of the bactericidal effect is
Compared with the degree of lesions in the untreated area, 6 stages (0: whole disease, 1: lesion area about 60%, 2: lesion area 40
%, 3: The lesion area is about 20%, 4: The lesion area is 1
0% or less, 5: no lesion). The results are shown in Table 10.
Shown in.

[0116]

[Table 10]

(7) Control Efficacy Test for Barley Powdery Mildew (Preventive Effect) 10 barleys (cultivar: black wheat) were grown in a plastic flower pot with a diameter of 6 cm, and 1.5 leaf stage seedlings were grown. In addition, each wettable powder of the compound (I) shown in Tables 2 and 3 prepared according to Example 2 was mixed with a surfactant (0.01
%) Was diluted to 500 ppm, and each of these chemical solutions was sprayed in an amount of 20 ml per pot. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated. The results are shown in Table 11 by the 6-step evaluation method described in (6) above.

[0118]

[Table 11]

[0119]

INDUSTRIAL APPLICABILITY The novel 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative of the present invention has excellent effects such as insecticidal, acaricidal and bactericidal.

─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Koichi Goka 5 1978, Ogushi, Ube, Yamaguchi Prefecture 5 1978, Ube Research Co., Ltd. Ube Laboratory (58) Fields investigated (Int.Cl. ⁷ , DB name) C07D 239/42 A01N 43/54 C07D 239/47 C07D 403/12 CA (STN) REGISTRY (STN)

Claims (6)

(57) [Claims] 1. The following formula (1): (In the formula, R ¹ is a halogen atom, a hydrogen atom or a carbon number of 1 to
Represents 4 alkoxy groups. R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R ³ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aliphatic acyl group having 2 to 5 carbon atoms, an imidazolecarbonyl group or a pyrazolecarbonyl group. m represents 0 or 1. n represents 1 or 2. ) 4- [2- (trifluoroalkoxy-substituted phenyl) ethylamino] pyrimidine derivative represented by 2. The following formula (2): (In the formula, R ¹ has the same meaning as described in claim 1.) and a pyrimidine derivative represented by the following formula (3-1): (In the formula, R ² , m and n have the same meanings as described in claim 1.) React with 2-phenethylamines represented by the formula (1) in claim 1. A 4-aminopyrimidine derivative represented by the following formula (1-1) in which R ³ is a hydrogen atom: (In the formula, R ¹ , R ² , m and n have the same meanings as defined in claim 1.) A process for producing a pyrimidine derivative represented by the formula. 3. A pyrimidine derivative represented by the formula (1-1) of claim 2 and the following formula (4): (In the formula, R ⁴ represents an alkyl group having 1 to ⁴ carbon atoms.)
The 4-aminopyrimidine derivative represented by the formula (1) according to claim 1, wherein R ³ has 2 carbon atoms, which is characterized by reacting with a lower aliphatic carboxylic acid chloride represented by
~ 5 aliphatic acyl groups represented by the following formula (1-2): (In the formula, R ¹ , R ² , R ⁴ , m and n have the same meanings as described in claim 1.) A process for producing a pyrimidine derivative represented by the formula. 4. A pyrimidine derivative represented by the formula (1-1) of claim 2 and the following formula (5): By reacting with trichloromethyl formate represented by the following formula (6): (In the formula, R ¹ , R ² , m and n have the same meanings as described in claim 1.) Then, an intermediate represented by the following formula (7): (In the formula, R ⁵ represents an imidazole group or a pyrazole group.) The azoles represented by the formula are reacted, and the 4-aminopyrimidine derivative represented by the formula (1) according to claim 1, R ³ Is an imidazole group or a pyrazole group, represented by the following formula (1-3): (In the formula, R ¹ , R ² , m, n and R ⁵ have the same meanings as described above.) A process for producing a pyrimidine derivative. 5. A pyrimidii represented by the formula (1-1) according to claim 2.
And derivatives Formula (3-2): [Chemical 11] (In the formula, R⁶Represents an alkyl group having 1 to 4 carbon atoms;
R², M and n have the same meanings as described in claim 1. )so
With the indicated N-alkyl substituted 2-phenethylamines
Formula (1) according to claim 1, characterized in that the reaction is carried out.
A 4-aminopyrimidine derivative represented by ³Is carbon
It is an alkyl group of 1 to 4 Formula (1-4): [Chemical 12] (In the formula, R⁶Is as defined above; R¹, R², M and
And n have the same meanings as described in claim 1. ) Indicated by
Method for producing limidine derivative. 6. The 4- represented by the formula (1) according to claim 1.
A pesticide for agricultural and horticultural use containing an aminopyrimidine derivative as an active ingredient.