JP2001335567A - 4-(1-fluoroethyl)pyrimidine-5-carboxylic acid amide derivative and harmful organism controller for agriculture and horticulture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a harmful organism controller for agriculture and horticulture effective on insect pests, pathogenic fungi and weeds, used for a foliage application, soil drench treatment and soil incorporation treatment, comprising a 4-(1-fluoroethyl)pyrimidine-4-carboxylic acid amide derivative as an active ingredient. SOLUTION: This 4-(1-fluoroethyl)pyrimidine-5-carboxylic acid amide derivative is represented by formula (1) (R is a substituted or nonsubstituted phenyl group, a substituted or nonsubstituted phenoxy, a substituted or nonsubstituted pyridyl group or a methyl group; A is a direct bond, a straight-chain or a branched-chain 1-12C alkylene).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative which is useful as a pesticide for agricultural and horticultural use.

[0002]

2. Description of the Related Art The 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative of the present invention is a novel compound, and thus is not known to have pest control activity for agricultural and horticultural use.

[0003]

An object of the present invention is to provide a novel 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative and an agricultural and horticultural pesticide containing the same as an active ingredient. It is to be.

[0004]

Means for Solving the Problems The present inventors have studied to solve the above-mentioned problems, and as a result, a novel 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative has been used for agricultural and horticultural purposes. The present invention was found to be useful as a pesticidal agent, and the present invention was completed. That is, the present invention is as follows. According to a first aspect, the following formula (1):

[0005]

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The present invention relates to a 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative represented by the formula: Here, R and A in the formula are as follows. R
Represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted pyridyl group, or a methyl group. A represents a direct bond, a linear or branched carbon atom having 1 to 1 carbon atoms.
Represents 12 alkylenes. The second invention provides the following formula (2):

[0007]

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The present invention relates to a 2- (1-fluoropropionyl) -3-dimethylamino-2-propenoate compound represented by the formula: In the formula, R ¹ has the same meaning as described above. The compound (2) represented by the formula (2) is
It is an intermediate for the production of compound (3). A third invention provides the following equation (3):

[0009]

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The present invention relates to a 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid ester compound represented by the formula: In the formula, R ¹ has the same meaning as described above. The compound (3) represented by the formula (3) is an intermediate for producing the compound (4). A fourth invention provides the following equation (4):

[0011]

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The present invention relates to 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid represented by the formula: The compound (4) represented by the formula (4) is an intermediate for producing the compound (1). The fifth invention relates to a pesticidal agent for agricultural and horticultural use, which comprises a 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative represented by the above formula (1) as an active ingredient.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The various substituents represented by the above compounds are as follows. In the description of the present invention, parenthesized numbers, symbols, and the like attached to chemical formulas are also referred to as "compounds (numerals, symbols, and the like)." For example, a compound represented by the formula (1) is also referred to as a compound (1). ]. [R] R represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy, a substituted or unsubstituted pyridyl group, or a methyl group.

(1) The substituted or unsubstituted phenyl group includes a linear or branched alkyl group having 1 to 4 carbon atoms, and a linear or branched alkoxy group having 1 to 4 carbon atoms. Groups, a merylene dioxy group, a linear or branched haloalkoxy group having 1 to 4 carbon atoms, and a phenyl group which may be substituted with a halogen atom; A chlorophenyl group, a 4-difluoromethoxyphenyl group, a 4-trifluoromethoxyphenyl group, a 3-isopropoxyphenyl group, and a 3,4-methylenedioxy group. (2) As the substituted or unsubstituted phenoxy, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkoxy group having 1 to 4 carbon atoms, a halogen atom And a phenoxy group which may be substituted with a trifluoromethoxy group;
It is a trifluoromethoxyphenoxy group. (3) Examples of the substituted or unsubstituted pyridyl group include a pyridyl group substituted by a linear or branched alkoxy group having 1 to 4 carbon atoms;
It is a methoxypyridyl group.

[R ¹ ] R ¹ represents an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group and an n-butyl group; preferably, an ethyl group. [A] A is a direct bond, a linear or branched carbon atom having 1
Represents up to 12 alkylenes. Examples of the linear or branched alkylene having 1 to 12 carbon atoms include methylene, methylmethylene, ethylmethylene, i-propylmethylene, ethylene, propylene, butylene, 1-
Examples thereof include a methyloctylene group and a 1-ethyloctylene group; preferably a methylene group, a methylmethylene group, an ethylmethylene group, an i-propylmethylene group, an ethylene group, and a 1-ethyloctylene group. .

As the compound (1), compounds obtained by combining the above-mentioned various substituents can be mentioned. From the viewpoint of efficacy, the following compounds are preferred. (1) The compound wherein A is a methylene group and R is a substituted or unsubstituted phenyl group. (2) The compound wherein A is (alkyl having 1 to 4 carbon atoms) methylene and R is substituted or unsubstituted phenyl. (3) A is an ethylene group, and R has 1 to 1 carbon atoms.
A compound which is a phenyl group substituted with four alkoxy groups or a haloalkoxy group having 1 to 4 carbon atoms. (4) A is an ethylene group, and R is from 1 to 1 carbon atoms.
A compound which is a phenoxy group substituted with four haloalkoxy groups. (5) The compound wherein A is a 1-methyloctylene group and R is a methyl group.

(6) Compound wherein A is a direct bond and R is a phenyl group substituted by an alkoxy group having 1 to 4 carbon atoms. (7) A is a direct bond and R is 1 carbon atom. A compound which is a phenyl group substituted with 4 to 4 alkoxy groups. (8) The compound wherein A is a direct bond and R is a pyridyl group substituted with an alkoxy group having 1 to 4 carbon atoms.

The method for synthesizing the compound (1) of the present invention is as follows:
This will be described in more detail. Compound (1) can be synthesized by the following synthesis method 1 or 2. (Synthesis Method 1) Compound (1) can be synthesized by reacting compound (4) with compound (5) in a solvent in the presence of a condensing agent as shown below.

[0019]

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(In the formula, R and A have the same meanings as described above.) The molar ratio of the raw materials can be set arbitrarily, but usually 0.5 to 0.5 mol of compound (5) per mol of compound (4). 2 mole ratio. The type of the solvent is not particularly limited as long as it does not directly participate in the reaction, for example, benzene,
Chlorinated or unchlorinated aromatic, aliphatic, cycloaliphatic such as toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, dichloroethane, trichloroethylene Hydrocarbons; ethers such as tetrahydrofuran, dioxane, diethyl ether and the like; and mixtures of the above-mentioned solvents.

The amount of the solvent used is such that the compound (4)
Weight percent can be used; however, 10
~ 70% by weight is preferred. As the condensing agent, N, N'-
Dicyclohexylcarbodiimide (abbreviation: DCC) or 1
Dehydration condensing agents such as -ethyl-3- (3-dimethylaminopropyl) -carbodiimide (abbreviation: WSC) can be mentioned; preferably, it is 1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide. . The amount of the condensing agent to be used is 1 to 5 moles relative to compound (4); preferably 1.0 to 1.5 moles. The reaction temperature is not particularly limited, but is in a temperature range from -20 ° C to the boiling point of the solvent or lower; preferably room temperature to 50 ° C.
The reaction time varies depending on the above concentration and temperature; it is usually 0.5 to 8 hours. The starting compound (5) can be obtained as a commercial product or can be produced by the method shown in the following formula. (1) When A is a linear alkylene group

[0022]

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(Wherein, R and A are as defined above;
Y represents a halogen atom. In addition, as the halogen atom for Y, a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like can be mentioned; preferably, a chlorine atom and a bromine atom are used. The starting compounds (6) and (7) can be obtained as commercial products. (2) When A is a branched alkylene group

[0024]

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(Wherein R and A are as defined above;
R2 represents a lower alkyl group having 1 to 3 carbon atoms. ) The starting compound (9) can be obtained as a commercial product. Compound (2) can be produced by the method shown by the following formula.

[0026]

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(Wherein R ¹ has the same meaning as described above.) The starting compound (10) can be produced by the method described in JP-A-11-171834, and (11) is obtained as a commercial product be able to. As the compound (2), for example, the compound shown in Example 1 described later can be mentioned. Compound (3) can be produced by the method shown by the following formula.

[0028]

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(In the formula, R ¹ has the same meaning as described above.) The starting compound (12) can be obtained as a commercial product. As the compound (3), for example, the following Example 1
Can be mentioned. Compound (4)
Can be manufactured by the method shown in the following formula.

[0030]

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(In the formula, R ¹ has the same meaning as described above.) (Synthesis Method 2) Compound (1) can also be synthesized by the following scheme.

[0032]

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(In the formula, R, A and Y have the same meanings as described above.) Examples of the compound (1) include compounds 1 to 20 shown in Table 1 below.

[Pest control effect] The pests for agricultural and horticultural use which are controlled by the compound (1) of the present invention include agricultural and horticultural insect pests (eg, brown planthoppers, spider mites, sweet potato nematodes, etc.), and agricultural and horticultural pathogens (eg, Wheat red rust, barley powdery mildew, cucumber downy mildew, rice blast, tomato late blight, etc.), and agricultural and horticultural weeds (eg, mehisiba, nobie, shiroza, inubeyu, morning glory). Further, the compound (1) of the present invention can be used for spraying leaves, irrigating the soil, and mixing the soil.

The pesticidal composition for agricultural and horticultural use of the present invention contains at least one compound (1) as an active ingredient. The compound (1) can be used alone, but it is usually compounded with a diluent, a surfactant, a dispersant, an auxiliary agent and the like by an ordinary method, for example, a dressing agent, an emulsion, a fine granule, a granule. It is preferable to adjust and use such compositions as wettable powders, wettable powders, wettable powders, aqueous suspensions, oily suspensions, emulsions, solubilized preparations, oils, microcapsules, aerosols and the like.

Examples of the solid diluent include talc, bentonite, montmorillonite, clay, kaolin, calcium carbonate, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea. Examples of the liquid diluent include hydrocarbons such as kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, dimethylnaphthalene and dimethylxylylethane; chlorinated hydrocarbons such as chloroform. Ethers such as dioxane and tetrahydrofuran; ketones;
For example, acetone, cyclohexanone, isophorone, etc .; esters, for example, ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc .; alcohols, for example, methanol, n-hexanol, ethylene glycol, etc .; polar solvents, for example, N, N -Dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone and the like; water and the like. Examples of the individual adhesive and dispersant include casein, polyvinyl alcohol, carboxymethylcellulose, bentonite, xanthan gum, and gum arabic. Aerosol propellants include, for example, air, nitrogen, carbon dioxide, propane, halogenated hydrocarbons and the like. Examples of the stabilizer include PAP, BHT and the like.

Examples of the surfactant include alcohol sulfates, alkyl sulfate salts, alkyl sulfonates, alkyl benzene sulfonates, lignin sulfonates, dialkyl sulfosuccinates, naphthalene sulfonate condensates, and polyoxyethylene. Examples thereof include alkyl ether, polyoxyethylene allyl ether, polyoxyethylene alkyl ester, alkyl sorbitan ester, polyoxyethylene sorbitan ester, and polyoxyethylene alkylamine.

In the preparation of the present agent, the above-mentioned diluents, surfactants, dispersants and adjuvants can be used alone or in appropriate combination according to the respective purposes.
When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually from 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
25 to 25% by weight, usually 1 to 90 for wettable powder and wettable powder.
%, Usually 0.5 to 10% by weight for granules, usually 0.5 to 40% by weight for suspensions, usually 1 to 30% by weight for emulsions, and usually 0.5 to 20% for solubilized preparations. % For aerosol, usually 0.1 to 5% by weight. These preparations can be diluted to an appropriate concentration and applied to various uses by spraying them on plant foliage, soil, or the water surface of paddy fields, or directly applying them, depending on the purpose.

[0039]

EXAMPLES The present invention will be specifically described below with reference examples and examples. Note that these examples do not limit the scope of the present invention.

Reference Example Synthesis of [Compound (10)] Synthesis of ethyl 4-fluoro-3-oxopentanoate 60% NaH in tetrahydrofuran (5 ml)
Oil (5.2 g) was added, and the mixture was heated and stirred at 35 ° C. Then, 1-fluoropropionic acid ethyl ester (12
g) and ethyl acetate (11.4 g) in toluene (10 m
The solution dissolved in 1) was slowly added dropwise so as not to exceed 40 ° C. After completion of the dropwise addition, the reaction was continued at 35 ° C. for 2 hours to complete the reaction. 12N hydrochloric acid (26.4 g) in water (4
0 ml) was added thereto, and the mixture was stirred under ice-cooling, and the reaction mixture was gradually added dropwise thereto. Ethyl acetate is added and the mixture is separated,
The separated organic layer was washed with saturated saline. After drying with sodium sulfate, the residue obtained by evaporating the solvent under reduced pressure was purified by vacuum distillation to obtain ethyl 4-fluoro-3-oxopentanoate (14.6 g).

B. p. 70-75 ° C./15 mmHg ¹ H-NMR (CDCl ₃ , δ ppm) 1.23 to 1.33 (3H, t), 1.47 to 1.57
(3H, m), 3.63 (2H, s), 4.18-4.
26 (2H, q), 4.87-5.30 (1H, q-
q)

Example 1 Synthesis of Compounds (1) to (4) (1) Synthesis of ethyl 2- (1-fluoropropionyl) -3-dimethylamino-2-propenoate [Compound (2)] N, N-Dimethylformamide dimethyl acetal (14.3 g) was added to ethyl -fluoro-3-oxopentanoate (16.2 g), and the mixture was stirred under reflux for 1 hour. After completion of the reaction, excess N, N-dimethylformamide dimethyl acetal was removed under reduced pressure to remove 2- (1
-Fluoropropionyl) -3-dimethylamino-2-
Ethyl propenoic acid ester (21.7 g) was obtained.

[0043]

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¹ H-NMR (CDCl ₃ , δ ppm) 1.26 to 1.33 (3H, t), 1.47 to 1.57
(3H, m), 2.88 (3H, s), 3.33 (3
H, s), 4.15 to 4.24 (2H, q), 5.55
~ 5.74 (1H, qq), 7.74 (1H, s)

(2) Ethyl 4- (1-fluoroethyl) pyrimidine-5-carboxylate [Compound (3)]
Synthesis of 20% sodium ethoxide ethanol solution (80
g) and formamidine acetate (21 g) under reflux and stirring
And 2- (1-fluoropropionyl) -3-dimethylamino-2-propenoic acid ester (43.4 g),
The mixture was stirred under reflux for 18 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The extract was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure.
The obtained residue is subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 4:
(Eluted with 1) to obtain 11 g of the target substance as a pale yellow liquid.

[0046]

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¹ H-NMR (CDCl ₃ , δ ppm) 1.41 to 1.46 (3H, t), 1.64 to 1.79
(3H, m), 4.41 to 4.48 (2H, q), 6.
24 to 6.46 (1H, qq), 9.19 (1H,
s), 9.36 (1H, s)

(3) Synthesis of 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid [compound (4)] To 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid ethyl ester (11 g) was added NaOH (4 g) dissolved in water (10 ml) was added, and the mixture was stirred at 80 ° C. for 1 hour. After completion of the reaction, 12N hydrochloric acid was gradually added to the mixture under ice cooling to adjust the pH to 2, and the precipitated crystals were collected by filtration and washed with water to obtain 4 g of the target substance as colorless powdery crystals. m. p. 148 to 151 ° C

(4) N- (4-chlorobenzyl) 4-
Synthesis of (1-fluoroethyl) pyrimidine-5-carboxylic acid amide [Compound (1) represented by compound No. 1] 4- (1-Fluoroethyl) pyrimidine-5-carboxylic acid (0.8 g) and 4 -Chlorobenzylamine (0.8
g) was dissolved in dichloromethane (30 ml), 1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride (1.5 g) was added, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, water was added to separate a methylene chloride layer,
The mixture was washed with 0.2N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Wakogel C-200, n-hexane: ethyl acetate = 2: 1] to give the target compound as colorless powdery crystals in 0%. 0.8 g was obtained.

M. p. 100-102 ° C. ¹ H-NMR (CDCl ₃ , δ ppm) 1.71-1.83 (3H, m), 4.61 (2H,
s) 5.85-6.03 (1H, qq), 7.28
8.37 (4H, m), 8.84 (1H, s), 9.
37 (1H, s)

(5) N- [2- (4-trifluoromethoxyphenyl) ethyl] -4- (1-fluoroethyl)
Synthesis of pyrimidine-5-carboxylic acid amide [Compound (1) represented by compound number 12] Synthesis of 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid (0.8 g) and thionyl chloride (0.6 g) 30
Heated to reflux for a minute. Then, the mixture was dissolved in toluene (20 ml), and 2- (4-trifluoromethoxyphenyl) ethylamine (1.1 g) and triethylamine (0.6 g) were added thereto while stirring with ice cooling, followed by stirring at room temperature for 2 hours. After the completion of the reaction, water was added, and toluene was separated, washed with 0.2 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to silica gel column chromatography [Wakogel C-200, n-hexane: ethyl acetate = 2: 1].
Purification of the target compound as colorless powdery crystals by 1.
3 g were obtained. m. p. 60-62 ° C

(6) Synthesis of Other Compound (1) in Table 1 Other compounds (1) in Table 1 were synthesized according to the methods (4) and (5) described above. Table 1 shows the compounds (1) synthesized as described above and their physical properties.

[0053]

[Table 1]

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 sodium dodecylbenzenesulfonate and 2 parts of sodium ligninsulfonate The parts by weight were uniformly mixed, and then a small amount of water was added and kneaded, followed by extrusion granulation and drying to obtain granules.

(2) Preparation of wettable powder Compound (1) 10 parts by weight, kaolin clay 70 parts by weight,
18 parts by weight of white carbon, 1.5 parts by weight of sodium dodecylbenzenesulfonate and 0.5 part by weight of β-naphthalenesulfonate sodium formalin condensate are uniformly mixed,
Subsequently, it was pulverized with an air mill to obtain a wettable powder.

(3) Preparation of Emulsion To 20 parts by weight of the compound (1) and 70 parts by weight of xylene, 10 parts by weight of Solpol 3005X (trade name, manufactured by Toho Chemical Co., Ltd.) were added, mixed uniformly, and dissolved to obtain an emulsion. Was.

(4) Preparation of emulsion 5 parts by weight of the powder of the compound (1), 50 parts by weight of talc and 45 parts by weight of kaolin clay were uniformly mixed to obtain a powder.

Example 3 [Efficacy Test] (1) Test for controlling efficacy against grape downy mildew (prevention test) One grape (cultivar: Neo Muscat) was grown per pot in a plastic flower pot having a diameter of 9 cm. An acetone solution of the compound (1) shown in Table 1 was added to the 6-leaf stage grape seedlings in 500 pp of water containing a surfactant (0.01%).
m and sprayed 15 ml per pot. After spraying, the plants were cultivated in a glass greenhouse for one day, and then a suspension of grape downy mildew zoospores (5 × 10 ⁴ cells / ml) was prepared and sprayed on the back of the leaves. After inoculation, the plants were kept in a moist chamber at 20 ° C. for 2 days, and then cultivated in a glass greenhouse for 11 days.
The degree of onset of downy mildew appearing on ６6 leaves was investigated. The effect was determined by comparing the degree of onset in the non-treated section with 5 without lesions, with a lesion area of 10% or less and about 4,20% in 3,40.
% About 2, 60% about 1, 0
Was carried out in 6 stages of 5 to 0. Table 2 shows these results.
Shown in

[0059]

[Table 2]

(2) Wheat Rust Control Efficacy Test (Preventive Efficacy) Ten wheat (cultivar: Kobushi wheat) were grown per pot in a plastic flower pot having a diameter of 6 cm. This 1.5
An acetone solution of the compound (1) shown in Table 1 was added to a young plant at the leaf stage with water containing a surfactant (0.01%) for 500 minutes.
It diluted to ppm and sprayed 10 ml per pot. After spraying, the plants were cultivated in a glass greenhouse for one day, and then a suspension of wheat rust fungus spores (3 × 10 ⁵ cells / ml) was prepared and sprayed on the plants uniformly. After inoculation, the plants were kept in a humidity chamber at 20 ° C. for 1 day, cultivated in a glass greenhouse for 9 days, and the occurrence of leaf rust on the first leaves was examined. The effect was judged by comparing the degree of onset in the untreated section with 5 without lesions and 4 or 2 in 10% or less lesion area.
The evaluation was performed in 6 stages of 5 to 0, with about 0% being about 3, 40%, about 2, 60% being about 1, and those having a total disease being 0.
Table 3 shows the results.

[0061]

[Table 3]

(3) Herbicidal activity test (field foliage treatment test) A 1/5000 arel Wagner pot was filled with volcanic ash soil, and seeds of Meechishiba, Shiroza, Inubeyu and Asagao were planted and covered with soil. Cultivated in the room for about 2 weeks. When each plant had grown appropriately, the wettable powder of compound (1) described in Table 1 prepared according to Example 2 was diluted to 2000 ppm with water containing a surfactant (0.05%). Each of the above plants was sprayed uniformly. After controlling for 3 weeks in a glass room at an average temperature of 25 ° C., their herbicidal effect was investigated. The evaluation of the herbicidal effect was shown in the following six stages as compared with the state of the untreated section. [0: normal growth, 1: slight harm, 2: minor harm, 3: medium harm,
4: Great harm, 5: Complete mortality] As a result, Compound Nos. 1, 8, 12, 16, and 20 show an effect of 4 or more on Crabgrass; Compound Nos. 1, 1
2,16 show an effect of 4 or more on Siroza; Compound Nos. 1,12,16,20 show an effect of 4 or more on Inubeille; Compound No.8 shows an effect of 4 on Asagao.
The above effects were shown.

(4) Efficacy test against sweet potato nematode Each wettable powder of compound (1) shown in Table 1 prepared according to Example 2 was diluted to 300 ppm with water, and 0.1 m
1 in a test tube, and add the sweet potato nematode 500
0.9 ml of the liquid containing the head was added. Next, these test tubes were allowed to stand in a low-temperature room at 25 ° C. and observed under a microscope two days later to determine the nematicidal rate. As a result, Compound No. 16
It showed 00% nematicidal activity.

(5) Tests against the spider mite Spider mite Each wettable powder of the compound (1) shown in Table 1 prepared according to Example 2 was washed with water containing a surfactant (0.01%) in water.
ppm, and each of these solutions was infested with 10 adult female spider mites, kidney bean leaves (diameter 20 mm).
For 15 seconds each. Next, each of these leaf pieces was added to 25
After 3 days, the number of live and dead insects in each leaf piece was counted to determine the acaricidal rate. As a result, Compound No. 1,
6, 8, and 12 showed acaricidal activity of 80% or more.

(6) Efficacy test on brown planthopper Each wettable powder of compound (1) shown in Table 1 prepared according to Example 2 was added to water containing a surfactant (0.01%) for 300 p.
pm, and the rice seedlings were immersed in each of these chemical solutions for 30 seconds, air-dried, and inserted into respective glass cylinders. Next, 10 glass brown planthoppers (4th instar larvae) were released into each of these glass cylinders, plugged with a porous plug, left in a constant temperature room at 25 ° C., and after 4 days, the number of live and dead insects was counted to determine the mortality. Was. As a result, Compound No. 3 showed an insecticidal activity of 80% or more.

[0066]

Industrial Applicability The 4- (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative of the present invention has an excellent agricultural and horticultural pest control effect.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C063 AA01 BB09 CC29 CC81 DD12 DD29 EE03 4H006 AA01 AB84 4H011 AA01 AB01 AC01 BA01 BA05 BB09 BC01 BC07 BC18 BC20 DA02 DA15 DA16 DD03 DD04

Claims (5)

[Claims] (1) The following formula (1): 4- (1-fluoroethyl) pyrimidine-5 represented by
-Carboxamide derivatives. Note that R and A in the formula are
It is as follows. R represents a substituted or unsubstituted phenyl group,
Represents a substituted or unsubstituted phenoxy, a substituted or unsubstituted pyridyl group, or a methyl group. A represents a direct bond, a linear or branched alkylene having 1 to 12 carbon atoms. 2. The following formula (2): 2- (1-fluoropropionyl) -3-dimethylamino-2-propenoic acid ester compound represented by the formula: In addition,
R ¹ in the formula is as defined above. 3. The following formula (3): 4- (1-fluoroethyl) pyrimidine-5 represented by
-Carboxylic acid ester compounds. In the formula, R ¹ represents a lower alkyl group having 1 to 4 carbon atoms. (4) 4- (1-fluoroethyl) pyrimidine-5 represented by
-Carboxylic acids. 5. The compound represented by the formula (1) according to claim 1,
A pest control agent comprising a (1-fluoroethyl) pyrimidine-5-carboxylic acid amide derivative as an active ingredient.