JPH07118242A - Phenoxyalkylamine derivative, its production and agri- and horticultural injurious creature controlling agent - Google Patents

Abstract

PURPOSE:To obtain a new phenoxyalkylamine derivative, useful as a control agent for agri- and horticultural injurious creatures, having excellent activities as insecticide, acaricide and germicide. CONSTITUTION:A compound is expressed by formula I [wherein, R<1> is a halogen, a 1-4C alkoxy, a 2-5C acyloxy, OH, phenoxy or a 1-4C alkylthio; R<2> and R<3> each is II or a l-4C alkyl; R<4> is a 1-8C alkyl, a 2-5C alkenyl, A-OR<6> (wherein, A is a 1-4C alkylene; R<6> is a 1-4C alkyl, a 2-5C alkenyl, a 3-6C alkynyl or a l 4C alkanol) or an aralkyl; R<5> is H, a halogen or a 1-4C alkyl], e. g. 5- chloro-6-(1-fluoroethyl)-4-[2-(2,4-dimethylphenoxy) ethylamino]pyrimidine. This compound is obtained by reacting a pyrimidine derivative of formula II (where X is a halogen) with a phenoxyalkylamine derivative of formula III. The subject compound is effective in controlling noxious insects in agri- and horticuluture, hygenic and grain storage, in controlling a root knot-nematode and a bulb mite in the soil, and in controlling agri- and horticultural pathogenic germs as well.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel phenoxyalkylamine derivative which is a pesticide for agricultural and horticultural use which is useful as an insecticide, acaricide, fungicide and the like.

[0002]

Description of the Prior Art As a phenoxyalkylamine derivative, for example, a quinazoline derivative is disclosed in JP-A-54-17.
123, JP-A-55-76803 and JP-A-55-76804, a thienopyrimidine derivative is disclosed in JP-A-59-42387, and a pyrimidine derivative is disclosed in JP-A-59-42387. Sho 59-3666
6, JP-A-59-36667, JP-A-61.
No. 286373 and JP-A-62-67, the pyrazole derivative is disclosed in JP-A-3-2736.
No. 0, JP-A-5-59011 and JP-A-5-59011.
It is disclosed in Japanese Patent No. 125054.

However, the disclosure of the phenoxyalkylamine derivative having a substituent at the 6-position ethyl group of the pyrimidine ring as in the present invention is not recognized. Therefore, since the phenoxyalkylamine derivative of the present invention is a novel compound, it is not known that it has an agricultural and horticultural pest control activity useful as an insecticide, acaricide or fungicide.

[0004]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a novel phenoxyalkylamine derivative, a method for producing the same, and a pest control agent for agricultural and horticultural use which is useful as an insecticide, acaricide or fungicide containing the derivative as an active ingredient. To provide the agent.

[0005]

Means for Solving the Problems As a result of studies to solve the above problems, the present inventors have found that a novel phenoxyalkylamine derivative is useful as an insecticide, acaricide, fungicide, etc. for agricultural and horticultural use. It was found that the pest control agent of the present invention has a remarkable control activity, and completed the present invention. That is, the present invention is as follows. The first invention is represented by the following formula (I):

[0006]

[Chemical 4]

[In the formula, R ¹ is a halogen group and has 1 to 4 carbon atoms.
Alkoxy groups, acyloxy groups having 2 to 5 carbon atoms,
Represents a hydroxyl group, a phenoxy group or an alkylthio group having 1 to 4 carbon atoms; R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R ³ represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom Represents R ⁴ is an alkyl group having 1 to 8 carbon atoms,
An alkenyl group having 2 to 5 carbon atoms, -A-OR ⁶ (in the formula,
A represents an alkylene group having 1 to 4 carbon atoms; R ⁶ represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, or 1 carbon atom. Represents ~ 4 alkanol groups. ) Or represents an aralkyl group;
R ⁵ represents a hydrogen atom, a halogen group or an alkyl group having 1 to 4 carbon atoms. ] It is related with the phenoxy alkylamine derivative shown by these. The second invention is the following formula (I
I):

[0008]

[Chemical 5]

(Wherein R ¹ has the same meaning as above; X represents a halogen atom) and a pyrimidine derivative represented by the following formula (III):

[0010]

[Chemical 6]

## STR1 ## wherein R ² , R ³ , R ⁴ and R ⁵ have the same meanings as defined above, and phenoxyalkylamines represented by the above formula are reacted. The present invention relates to a method for producing a phenoxyalkylamine derivative. A third invention relates to a pest control agent for agricultural and horticultural use, which comprises the phenoxyalkylamine derivative represented by the formula (I) as an active ingredient.

The present invention will be described in detail below. Regarding the target compound and the starting material compound, R ^{1 to} R ⁵ represented by the novel phenoxyalkylamine derivative [compound (I)] and the starting material [compound (II) or compound (III)] for the target compound are as follows. Is.

[R ¹ ] R ¹ is a halogen group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, a hydroxyl group, a phenoxy group, an alkylthio group having 1 to 4 carbon atoms, etc. Can be mentioned. Examples of the halogen group include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom; preferably a fluorine atom and a chlorine atom.

The alkoxy group may be a linear or branched one, and preferably has 1 carbon atom.
Up to 2 groups (methoxy group, ethoxy group, etc.) are preferable.
Examples of the acyloxy group include those having a linear or branched alkyl group; preferably those having 2 to 4 carbon atoms; and more preferably acetyloxy group.

Examples of the alkylthio group include those having a linear or branched alkyl group;
A methylthio group is preferred. [R ² ] Examples of R ² include a hydrogen atom and an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group include linear or branched ones;
A methyl group is preferred.

[R ³ ] Examples of R ³ include an alkyl group having 1 to 4 carbon atoms and a hydrogen atom. Examples of the alkyl group include linear or branched ones; preferably a methyl group.

[R ⁴ ] R ⁴ is an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or -A-O.
R ⁶ and aralkyl groups can be mentioned. Examples of the alkyl group include linear or branched ones; preferably those having 1 to 6 carbon atoms; more preferably those having 1 to 5 carbon atoms (methyl group, ethyl group , N-propyl group, i-propyl group, n-butyl group, i-butyl, sec-butyl group, etc.) are preferred.

Examples of the alkenyl group include linear and branched ones; preferably having 2 to 2 carbon atoms.
Four groups are preferable; allyl groups are more preferable.
Examples of A in -A-OR ⁶ include an alkylene group having 1 to 4 carbon atoms; preferably an alkylene group having 1 to 2 carbon atoms; more preferably an ethylene group. The R ⁶ in -A-OR ^6, 1~ carbon atoms
Examples thereof include an alkyl group having 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkynyl group having 3 to 6 carbon atoms, and an alkanol group having 1 to 4 carbon atoms.

Examples of the alkyl group for R ⁶ include linear or branched ones; preferably those having 1 to 3 carbon atoms (methyl group, ethyl group, n-propyl group, i -Propyl group etc.) Examples of the alkenyl group for R ⁶ include linear and branched ones; preferably an allyl group. Examples of the alkynyl group for R ⁶ include linear and branched ones; preferably a propargyl group. Examples of the alkanol group for R ⁶ include linear or branched ones; preferably a hydroxyethyl group. The aralkyl group is preferably a benzyl group.

[R ⁵ ] Examples of R ⁵ include a hydrogen atom, a halogen group, and an alkyl group having 1 to 4 carbon atoms. As the halogen group, chlorine atom, iodine atom,
Examples thereof include a bromine atom and a fluorine atom; preferably a chlorine atom. The substitution position of the halogen group is not particularly limited, but the 6-position is preferable.

The alkyl group may be a linear or branched alkyl group; preferably a methyl group. The substitution position of the alkyl group is not particularly limited; preferably 3-position and 6-position.

Since the compound (I) of the present invention has an amino group, acid addition salts derived from them are also included in the present invention. Examples of acids that form acid addition salts include inorganic acids (hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid, etc.); carboxylic acids (formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid). , Aconitic acid, etc.); organic sulfonic acid (methanesulfonic acid, benzenesulfonic acid, p-
Toluenesulfonic acid, etc.); saccharin, etc. can be mentioned.

Further, since the compound (I) of the present invention contains an asymmetric carbon atom indicated by *, any of the individual optical isomers, racemates, and mixtures thereof derived from these are included in the present invention. .

Synthetic Method of Compound (I) As a preferred embodiment for producing the phenoxyalkylamine derivative represented by the above-mentioned formula (I), in addition to the synthetic method 1 described as the second invention, the following five kinds The production method (Synthesis methods 2 to 6) can be mentioned. (Synthesis Method 2) The following formula (I-1):

[0025]

[Chemical 7]

(Wherein R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above; R ⁷ represents a halogen atom) and a phenoxyalkylamine derivative represented by the following formula (IV):

[0027]

[Chemical 8]

In the above formula (I), R ¹ is a lower acyloxy group, which is characterized by reacting with a lower aliphatic carboxylic acid represented by the formula (R ⁸ represents a lower acyloxy group). Process for producing phenoxyalkylamine derivative [referred to as compound (I-2)] (Synthesis Method 3) The following formula (I-2):

[0029]

[Chemical 9]

(Wherein R ² , R ³ , R ⁴ , R ⁵ and R ⁸
Is as defined above. ) And a phenoxyalkylamine derivative represented by the following formula (V):

[0031]

[Chemical 10]

(In the formula, M represents an alkali metal.) Inorganic bases represented by the formula (I) are reacted to form a phenoxyalkylamine derivative in which R ¹ is a hydroxyl group [compound (I-3)]. (Synthesis Method 4) A phenoxyalkylamine derivative represented by the above formula (I-1) and the following formula (VI):

[0033]

[Chemical 11]

(In the formula, R ⁹ represents a lower alkyl group; Y
Represents an oxygen atom or a sulfur atom. ) Is reacted with an alcohol (or a mercaptan) represented by the formula (I), wherein R ¹ is a lower alkoxy group (or lower alkylthio group) in the above formula (I). -4)]]. (Synthesis Method 5) A phenoxyalkylamine derivative represented by the above formula (I-1) and the following formula (VII):

[0035]

[Chemical 12]

(In the formula, M has the same meaning as defined above.) A phenoxyalkyl group wherein R ¹ is a fluorine atom is reacted with an alkali metal fluorine compound represented by the formula (I). Amine derivative (Compound (I-
5)]]. (Synthesis Method 6) The following formula (I-3):

[0037]

[Chemical 13]

(Wherein R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above) and a phenoxyalkylamine derivative represented by the following formula (VIII):

[0039]

[Chemical 14]

A process for producing the compound (I-5), which comprises reacting with a fluorinating agent represented by:

Synthesis methods 1 to 1 of the above-mentioned compound (I) of the present invention
6 will be described in more detail. [Synthesis Method 1] Synthesis of compound (I) in Synthesis Method 1 is as follows.
Usually, it can be carried out by reacting the starting compound (II) with compound (III) in a solvent or in the absence of a solvent; it is preferable to react in the presence of a base in order to accelerate the reaction.

The solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroine, hexane, chlorobenzene, dichlorobenzene, methylene chloride, Chlorinated, non-chlorinated aromatic, aliphatic, alicyclic hydrocarbons such as dichloroethane, trichloroethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane; acetone, methyl ethyl ketone, etc. Ketones such as; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, etc .; nitriles such as acetonitrile, propionitrile, etc .; triethylamine, pyridine, N, N-dimethylaniline, etc. And the like mixtures of the solvents; 1,3-dimethyl-2-imidazolidinone; dimethylsulfoxide organic bases such as.

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

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

The amount of the base used is the compound (I
It can be used in an amount of 0.001 to 5 times by mole with respect to I); preferably 0.8 to 2 times by mole. The reaction temperature is not particularly limited, but is within a temperature range of room temperature to the boiling point of the solvent used; preferably 80 to 110 ° C.

The reaction time varies depending on the above-mentioned concentration and temperature; it can usually be carried out for 0.3 to 2 hours. The amount of the raw material compound used is the amount of the compound (II
I) is 0.5 to 2 times mol; preferably 0.8 to
1.5 times mol is preferable.

The compound (II) (when R ¹ = X) used in the present invention is usually the starting compound (IX-1) as shown below.
And compound (X-1) can be produced by reacting in a solvent.

[0048]

[Chemical 15]

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

The amount of the starting compound used is 0.5 to 3 times mol of the compound (X-1) with respect to the compound (IX-1); preferably 0.5 to 1.7 times mol. Is good. Compound (IX-
1) is, for example, Journal of Chemical Society (JCS) 3478-3481 (1955).
According to the method described in 1), it can be produced by carrying out as shown in the following formula.

[0051]

[Chemical 16]

(In the formula, X has the same meaning as described above; R represents a lower alkyl group, a hydrogen atom, a hydroxyl group or a halogen atom.) The target compound (II) produced as described above has the reaction completed. After that, usual post-treatments such as extraction, concentration, and filtration are performed, and if necessary, it can be appropriately purified by a known means such as recrystallization and various chromatography. Compound (I
I) include compounds (II-1) to (II shown in Table 1 below.
-7) and the like. Compound used in the present invention
(III) can be manufactured by carrying out as shown in the following formula.

[0053]

[Chemical 17]

(In the formula, R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above.) The compound (III) corresponds to compounds 1 to 48 shown in Tables 2 to 6 below. Compounds (III) consisting of the respective types of the substituents [compounds (III) ₁ to (III) ₄₈ are referred to. For example, in the compound (III) ₁ , R ² and R ⁵ in the formula represented by the compound (III) are hydrogen atoms, and R ³ and R ⁴ are methyl groups. ] Can be mentioned.

Examples of the compound (I) include compounds 1 to 48 shown in Tables 2 to 6 below. [Compound 1 is a compound represented by the formula (I) in which R ¹ is a fluorine atom. , R ² and R ⁵ are chlorine atoms, and R ³ and R ⁴ are methyl groups. ].

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

Examples of the solvent include, in addition to the solvent described in Synthesis Method 1, aliphatic carboxylic acids such as acetic acid and propionic acid, and mixtures thereof;
-Dimethylformamide and the same aliphatic carboxylic acid as the acyloxy group to be introduced are preferable.

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

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

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

Compounds (I-2) are shown in Tables 2 to 6 below.
Compounds 5, 13, 17, 23, 27, 33, 3 shown in
Is it the type of each substituent corresponding to 5, 37, 45, 46, etc.
Compound (I-2) [Compound (I-2)_Five， (I-2)₁₃， (I-
2)₁₇， (I-2)_{twenty three}， (I-2)₂₇， (I-2)₃₃， (I-2)₃₅， (I-
2)₃₇， (I-2)₄₅， (I-2)₄₆And so on. For example,
Compound (I-2)_FiveIs R in the formula of compound (I)
¹(R in the compound (I-2)⁸) Is an acetyloxy group
Yes, R², R^FourAnd R^FiveIs a hydrogen atom, and R ³The
It is a chill group. ] Can be mentioned.

[Synthesis Method 3] Compound (I-3) [Compound (I)
[Wherein R ¹ is a hydroxyl group]
It can be carried out by reacting compound (I-2) with compound (V) in a solvent; however, it is preferable to react in the presence of an excess base to promote the reaction.

As the solvent, in addition to the ethers, ketones, and amides described in Synthesis Method 1, alcohols (methanol, ethanol, propanol, butanol, etc.),
Mention may be made of water and a mixture of the aforementioned solvents; preferably a mixture of alcohols and water. And
The amount of the solvent used may be such that the concentration of the compound (I-2) is in the concentration range of 5 to 80% by weight; preferably the concentration of the compound (I-2) is 10 to 70. weight%
It is good to use it as.

Examples of the base include the inorganic bases described in Synthesis Method 1; sodium hydroxide and potassium hydroxide are preferred. The base can be used in a 1- to 5-fold molar quantity with respect to compound (I-2); preferably, it is a 2- to 5-fold molar quantity.

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

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

Compounds (I-3) are shown in Tables 2 to 6 below.
Corresponds to compounds 6, 14, 18, 24, 28, etc.
Each compound (I-3) consisting of the type of each substituent
-3) ₆, (I-3)₁₄， (I-3)₁₈， (I-3)_{twenty four} , (I-3)₂₈Such
Called. For example, compound (I-3)₆ Is compound (I)
R in the formula shown¹Is a hydroxyl group, and R², R^FourOver
And R^FiveIs a hydrogen atom, and R³Is a methyl group. ]
Can be mentioned.

[Synthesis Method 4] Compound (I-4) [Compound (I)
[Wherein R ¹ is an alkoxy group, a phenoxy group or an alkylthio group].
It can be carried out by reacting the compound (VI) with a compound (VI) in a solvent or without a solvent; however, it is preferable to react in the presence of a base in order to accelerate the reaction.

Examples of the solvent include ethers, ketones, amides and a mixture of the above solvents described in Synthesis Method 1; preferably, ketones and amides. The amount of the solvent used may be such that the concentration of the compound (I-1) is in the range of 5 to 80% by weight; preferably, the concentration of the compound (I-1) is 10
It is advisable to use it in an amount of up to 70% by weight.

Examples of the base include the bases described in Synthesis Method 1; inorganic bases are preferred. The base can be used in a 1- to 5-fold molar quantity with respect to compound (I-1); preferably, it is a 1- to 3-fold molar quantity. The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent used or less; preferably room temperature to 60 ° C. The reaction time depends on the above concentration,
Although it depends on the temperature, it can usually be carried out in 0.3 to 2 hours.

As the compound (VI), a commercially available product can be used. The target compound (I-
After the reaction, 4) 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.

Compounds (I-4) are shown in Tables 2 to 6 below.
Corresponding to compounds 3, 10, 20, 21, 30 etc. shown in
Each compound (I-4) consisting of each substituent type
-Four) ₃, (I-4)_Ten， (I-4)₂₀， (I-4)_{twenty one}, (I-4)₃₀Such
Called. For example, compound (I-4)₃Is compound (I)
R in the formula shown¹Is an ethoxy group, R²as well as
R^FiveIs a hydrogen atom, and R³And R^FourIs a methyl group
It ] Can be mentioned.

[Synthesis Method 5] Compound (I-5) [Compound (I)
[Wherein R ¹ is a fluorine atom in] is usually synthesized by reacting compound (I-1) with compound (VII) in a solvent or without solvent; In order to carry out the reaction, it is preferable to heat and react.

Examples of the solvent include amides such as N, N-dimethylformamide and N, N-dimethylacetamide; 1,3-dimethyl-2-imidazolidone; dimethyl sulfoxide; sulfolane; a mixture of the above solvents. it can.

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

The amount of the compound (I-1) used can be 1 to 5 times by mole, preferably 1.2 to 3 times by mole with respect to the compound (I-1). It should be The reaction temperature is not particularly limited, but is within a temperature range from room temperature to the boiling point of the solvent to be used; preferably 10
0-140 degreeC is good. The reaction time varies depending on the above-mentioned concentration and temperature; it can usually be carried out for 1 to 8 hours.

[Synthesis Method 6] In addition to Synthesis Method 5, the compound (I-5) can be synthesized by reacting the compound (I-3) with a fluorinating agent in a solvent. As a solvent,
Chlorinated or unchlorinated aromatic, aliphatic or alicyclic hydrocarbons described in Synthesis Method 1; diethyl ether,
Ethers such as tetrahydrofuran, dioxane and the like; a mixture of the above solvents and the like can be mentioned.

The amount of the solvent used is the compound (I-
The compound (3) can be used in a concentration range of 5 to 80% by weight; preferably, the compound (I-3) is used in a concentration of 10 to 70% by weight. Good. The fluorinating agent is not particularly limited, but the following formula:

[0079]

[Chemical 18]

Diethylaminosulfur trifluoride (DAST) represented by can be used. And, the amount used is 1 to the compound (I-3).
It can be used in a 5-fold molar amount; preferably compound (I
-1) to 1 to 2 times the molar amount is preferred. The reaction temperature is not particularly limited, but is within a temperature range from the ice-cooling temperature to the boiling point of the solvent used or less; preferably the ice-cooling temperature to room temperature.

The reaction time varies depending on the above-mentioned concentration and temperature, but can usually be 0.3 to 2 hours. Target compound (I-5) produced by Synthetic Methods 5 and 6
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.

Examples of the compound (I-5) include compounds 1, 7, 15, 19, 25, 29, 38 shown in Tables 2 to 6 below.
To (44), (47), (48) and the like, each of which is a compound (I-5) [compound (I-5) ₁ , (I-5) ₇ , (I-5)]
₁₅ , (I-5) ₁₉ , (I-5) ₂₅ , (I-5) ₂₉ , (I-5) ₃₈ ~ ₄₄ , (I-
5) ₄₇ , (I-5) _48, etc. For example, compound (I-5) ₁
And R ^{1 in the} formula represented by the compound (I) is a fluorine atom, R ² and R ⁵ are hydrogen atoms, and R ³ and R
⁴ is a methyl group. ] 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 (I) of the present invention, there is an agricultural and horticultural pest [for example, Hemiptera (Plants) 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 a particularly remarkable insecticidal, acaricidal, and bactericidal effect, and contains at least one compound (I) as an active ingredient. It is a thing. Compound (I) can be used alone, but it is usually prepared by a conventional method using a carrier, a surfactant,
It is preferable to use a mixture of a dispersant, an auxiliary agent and the like (prepared as a composition such as powder, emulsion, fine granules, granules, wettable powder, oily suspension and 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.

Examples of surfactants and dispersants that can be used to improve the performance of the present 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 this 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 in the case of emulsion and 0.3 in the case of powder.
25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, usually 0.1 to 5% by weight for aerosols. is there. These formulations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, water surface of paddy field or directly applied to various applications depending on the purpose.

[0088]

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

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

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

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

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

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

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

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

(Physical Properties) ¹ H-NMR (CDCl ₃ , δppm) 1.47 to 1.52 (d, 3H), 3.76 to 3.85
(D, 1H), 5.17 to 5.25 (m, 1H), 8.
88 (s, 1H)

(6) Synthesis of other raw material compounds (II) in Table 1 Other raw material compounds (II) in Table 1 were synthesized by the same method as in the above (1) to (5).

[0098]

[Table 1]

Example 1 [Synthesis of Compound (I)] The target compound (I) was synthesized using the compound (II) obtained in Reference Example 1. (1) 5-chloro-6- (1-fluoroethyl) -4-
[2- (2,4-dimethylphenoxy) ethylamino]
Synthesis of Pyrimidine (Compound 1) 2- (2,4-Dimethylphenoxy) ethylamine (1.65 g) and triethylamine (1.2 g) were dissolved in toluene (30 ml) to prepare 4,5-dichloro-6-.
(1-Fluoroethyl) pyrimidine (2.0 g) was added, and the mixture was heated under reflux 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 oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification by elution (4: 1) yielded 1.6 g of the target compound as pale yellow powdery crystals.

(2) Synthesis of 5-chloro-6- (1-chloroethyl) -4- [2- (2,4-dimethylphenoxy) ethylamino] pyrimidine (Compound 2) 2- (2,4-dimethylphenoxy) ) Ethylamine (1.65 g) and triethylamine (1.2 g) were dissolved in toluene (30 ml) and 4,5-dichloro-6-
(1-chloroethyl) pyrimidine (2.1 g) was added,
The mixture was heated under reflux for 3 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 oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 5:
(1 elution) to obtain 2.6 g of the target compound as colorless powdery crystals.

(3) Synthesis of 5-chloro-6- (1-ethoxyethyl) -4- [2- (2,4-dimethylphenoxy) ethylamino] pyrimidine (Compound 3) Compound obtained in (2) above 2 (1.0 g) and sodium ethoxide (0.3 g) were dissolved in ethanol (10 ml), and the mixture was heated under reflux for 1 hr. After completion of the reaction, water was added to the reaction mixture, 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 oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate =
Purification by elution (5: 1) gave 0.9 g of the target compound as a colorless oily liquid.

(4) 5-chloro-6- (1-chloroethyl) -4- {2- [4- (2-ethoxyethyl) -2-
Synthesis of methylphenoxy] ethylamino} pyrimidine (Compound 16) 2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethylamine (2.2 g) and triethylamine (1.2 g) in toluene (30 ml). Melt, 4,
5-Dichloro-6- (1-chloroethyl) pyrimidine (2.1 g) was added, and the mixture was heated under reflux for 3 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 oily substance was purified by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 5: 1 elution), and then n-
By recrystallizing from hexane, 3.1 g of the target compound, which is a colorless cotton-like crystal, was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.20 (t, 3H) 1.82 to 1.88 (d, 3)
H), 2.25 (s, 3H), 2.80 (t, 3H),
3.45 to 3.63 (m, 4H), 3.95 (q, 2)
H), 4.15 (q, 2H), 5.90 (q, 1H),
6.00 (b, 1H), 6.25 (d, 1H), 6.9
5 to 7.05 (m, 2H), 8.55 (s, 1H)

(5) 6- (1-acetoxyethyl) -5-
Chloro-4- {2- [4- (2-ethoxyethyl) -2
Synthesis of -Methylphenoxy] ethylamino} pyrimidine (Compound 17) Compound 16 (4.0 g) obtained in the above (4) was dissolved in N, N-dimethylformamide (30 ml), and potassium acetate (1.2 g) was added. Potassium carbonate (1.4 g) was added, and the mixture was heated under reflux for 4 hours. After completion of the reaction, water was added to the reaction mixture, 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 oily substance was purified by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 4: 1 elution) to obtain 3.9 g of the target compound as colorless powdery crystals.

(6) 5-chloro-6- (1-hydroxyethyl) -4- {2- [4- (2-ethoxyethyl) -2
Synthesis of -methylphenoxy] ethylamino} pyrimidine (Compound 18) Compound 17 (2.15 g) obtained in (5) above was dissolved in ethanol (25 ml), 1N-sodium hydroxide aqueous solution (13 ml) was added, and the mixture was stirred at room temperature. The mixture was heated and stirred for 1 hour. After completion of the reaction, water was added to the reaction mixture, 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 oily substance was subjected to silica gel column chromatography (Wako Gel C-200,
The residue was purified with toluene: ethyl acetate = 3: 1 (elution) to obtain 1.8 g of the target compound as a colorless oily liquid.

(7) 5-chloro-6- (1-fluoroethyl) -4- {2- [4- (2-ethoxyethyl) -2-
Synthesis of Methylphenoxy] ethylamino} pyrimidine (Compound 19) Compound 18 (2.5 g) obtained in (6) above was dissolved in chloroform (50 ml), and diethylaminosulfur trifluoride (DAST) (1 0.0 g) was added dropwise and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, under ice cooling,
Water was slowly added to the reaction mixture, the organic solvent layer was separated, this organic solvent layer was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C-
200, toluene: ethyl acetate = 10: 1 elution) to obtain 1.9 g of the target compound as a pale yellow oily liquid.

(8) 5-chloro-6- (1-methylthioethyl) -4- {2- [4- (2-ethoxyethyl) -2
Synthesis of -Methylphenoxy] ethylamino} pyrimidine (Compound 21) Compound 16 (1.5 g) obtained in (4) above was dissolved in methanol (15 ml), and a methyl mercaptan sodium salt aqueous solution (15% aqueous solution 4 ml) was added. In addition, the mixture was stirred at room temperature for 5 hours. After completion of the reaction, water was added to the reaction mixture, 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 oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 4: 1 elution).
The target compound which is a colorless oily liquid was obtained by 1.6 g.

(9) N-methyl-6- (1-acetoxyethyl) -5-chloro-4- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethylamino} pyrimidine (Compound 22 ) Synthesis of N-methyl-4- {2- [4- (2-ethoxyethyl)
2-Methylphenoxy] ethylamine (2.4 g) and triethylamine (1.2 g) were added to toluene (30 m).
1) dissolved in 6- (1-acetoxyethyl) -4,5
-Dichloropyrimidine (2.4 g) was added, and the mixture was heated under reflux for 6 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 oily substance was purified by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 4: 1 elution) to obtain 4.0 g of the target compound as a colorless oily liquid.

(10) N-methyl-5-chloro-6- (1-
Synthesis of hydroxyethyl) -4- {2- [4- (2-ethoxyethyl) -2-methylphenoxy] ethylamino} pyrimidine (Compound 23) N-methyl-4- {2- [4- (2-ethoxy) ethyl)
2-Methylphenoxy] ethylamine (2.4 g) and triethylamine (1.2 g) were added to toluene (30 m).
It was dissolved in 1), 4,5-dichloro-6- (1-hydroxyethyl) pyrimidine (2.0 g) was added, and the mixture was heated under reflux for 6 hours. After completion of the reaction, water was added to the reaction mixture, 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 oil was purified by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 4: 1) to obtain 3.5 g of the target compound as a colorless oily liquid.

(11) Synthesis of 5-chloro-6- (1-fluoroethyl) -4- [2- (4-benzylphenoxy) ethylamino] pyrimidine (Compound 39) 5-chloro-6- (1-chloroethyl ) -4- [2-
(4-Benzylphenoxy) ethylamino] pyrimidine (2.5 g) was added to N, N-dimethylformamide (30 m
It melt | dissolved in 1), cesium fluoride (3.0g) was added, and it stirred at 120-140 degreeC for 12 hours. After completion of the reaction, water was added to the reaction mixture, 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 oily substance was purified by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 4: 1) to obtain 1.9 g of the target compound as colorless powdery crystals.

(12) Synthesis of 5-chloro-6- (1-fluoroethyl) -4- [2- (4-benzyl-2,3-dimethylphenoxy) ethylamino] pyrimidine (Compound 40) 2- (4 -Benzyl-2,3-dimethylphenoxy) ethylamine (1.8 g) and triethylamine (3.6
g) and were dissolved in toluene (30 ml), and 5-chloro-
4-Fluoro-6- (1-fluoroethyl) pyrimidine (1.0 g) was added, and the mixture was heated under reflux for 3 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 oily substance was purified by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 20: 1) to obtain 1.5 g of a target compound as a pale yellow oily liquid.

(13) Synthesis of other compounds (I) in Tables 2 to 7 Other compounds (I) in Tables 2 to 7 were synthesized according to the methods described in (1) to (12) above. did. The compounds synthesized as described above are shown in Tables 2 to 7.

[0113]

[Table 2]

[0114]

[Table 3]

[0115]

[Table 4]

[0116]

[Table 5]

[0117]

[Table 6]

[0118]

[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 lignin sulfonate were uniformly mixed, and then a small amount of water was added and kneaded, and then granulated and dried to obtain granules.

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

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

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

Example 3 [Efficacy test] (1) Efficacy test against diamondback moth Compound (I) shown in Tables 2 to 7 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
After diluting to 0 ppm, cabbage leaf pieces (5 × 5 cm) were dipped in each of these chemical solutions for 30 seconds, placed in each plastic cup one by one and air dried. Next, in each of these cups, 10 diamondback moths (third instar larvae) were released, and the cups were capped.
The cup was allowed to stand in a constant temperature room at 5 ° C., and two days later, the number of live and dead insects in each cup was counted to determine the mortality rate.

The insecticidal effect is evaluated in four stages (A: 100%, B: less than 100-80%, depending on the range of mortality).
C: less than 80 to 60%, D: less than 59%). The results are shown in Table 8.

[0125]

[Table 8]

(2) Efficacy test against green leafhoppers Compounds (I) shown in Tables 2 to 7 prepared according to Example 2
Each of the wettable powders of No. 1 was diluted to 300 ppm with water containing a surfactant (0.01%), rice seedlings were immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder. did. Next, 10 green leafhoppers (4th instar larvae) were left in each cylinder, capped with a porous plug, allowed to stand in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the insecticidal rate. The results of evaluation of the insecticidal effect are shown in Table 9 by the four-step evaluation method described in (1) above.

[0127]

[Table 9]

(3) Efficacy test against adult female adults of Nite spider Mite (I) shown in Tables 2 to 7 prepared according to Example 2
30% of each wettable powder in water containing surfactant (0.01%)
Each kidney bean leaf piece (diameter: 20 m) diluted to 0 ppm and infested with 10 adult female adults
m) was immersed for 15 seconds each. Next, each leaf piece was left in a constant temperature room at 25 ° C., and three days later, the number of live and dead insects in each leaf piece was counted to determine the miticidal rate.

The evaluation of the acaricidal effect is carried out in four steps (A: 100%, B: less than 100 to 80 depending on the range of the acaricidal rate).
%, C: less than 80 to 60%, D: less than 59%). The results are shown in Table 10.

[0130]

[Table 10]

(4) Control efficacy test against barley powdery mildew (preventive effect) Ten 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 to 7 prepared according to Example 2 was mixed with a surfactant (0.01%).
Each of them was sprayed with 20 ml per one pot by diluting each to 500 ppm with water containing water. These were cultivated in a glass greenhouse for 2 days, and then the barley powdery mildew fungus conidia spores were collected from the diseased leaves and sprinkled evenly over the plants to inoculate. Next, these were grown in a glass greenhouse for one week, and the degree of barley powdery mildew lesions appearing on each first leaf was investigated.

The evaluation of the bactericidal effect is carried out in 6 stages (0: whole diseased, 1: lesion area is about 60%, 2: lesion area is about 40%, as compared with the degree of lesions in the untreated section. 3: The lesion area is about 20%, 4: The lesion area is 10% or less, and 5: No lesion). The results are shown in Table 11.

[0133]

[Table 11]

(5) Control efficacy test against cucumber downy mildew (preventive effect) One cucumber (cultivar; Sagamihanjiro) was grown in a plastic flower pot with a diameter of 6 cm, and a 1.5-leaf stage young plant A wettable powder prepared from the target compound (I) shown in Tables 2 to 7 according to Example 2 was applied to the body by a surfactant (0.01
%) And dilute to 500 ppm with water containing 2% per pot.
Sprayed with 0 ml. After spraying, grow in a glass greenhouse for 2 days, then cucumber downy mildew (Pseudoperonospora cu)
bensis) zoosporangia was prepared from diseased leaves and spray-inoculated uniformly on the back surface of plant leaves. 2 days after vaccination
After keeping it at 0 ° C. in the dark, it was grown in a glass greenhouse for 5 days, and the degree of cucumber downy mildew lesions appearing on the first leaf was investigated. The result of the evaluation of the bactericidal effect is described in (4) above.
Table 12 shows the evaluation methods of stages.

[0135]

[Table 12]

[0136]

The novel phenoxyalkylamine derivative of the present invention has excellent effects such as insecticidal, acaricidal, and bactericidal.

Claims (3)

[Claims] 1. The following formula: [In the formula, R ¹ represents a halogen group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 2 to 5 carbon atoms, a hydroxyl group, a phenoxy group or an alkylthio group having 1 to 4 carbon atoms;
R ² represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R ³ represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom; R ⁴ represents an alkyl group having 1 to 8 carbon atoms, carbon Number 2
5 alkenyl groups, -A-OR ⁶ (wherein A represents an alkylene group having 1 to 4 carbon atoms; R ⁶ is an alkyl group having 1 to 4 carbon atoms, alkenyl having 2 to 5 carbon atoms) Group, an alkynyl group having 3 to 6 carbon atoms or an alkanol group having 1 to 4 carbon atoms) or an aralkyl group; R ⁵ represents a hydrogen atom, a halogen group or an alkyl group having 1 to 4 carbon atoms. Represent ] The phenoxy alkylamine derivative shown by these. 2. The following formula: (Wherein R ¹ has the same meaning as described in claim 1; X represents a halogen atom) and a pyrimidine derivative represented by the following formula: (Wherein R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described in claim 1) and a phenoxyalkylamine represented by the formula (1) is reacted. A method for producing a phenoxyalkylamine derivative represented by I). 3. A pesticide for agricultural and horticultural use, which comprises the phenoxyalkylamine derivative represented by the formula (I) according to claim 1 as an active ingredient.