JP4838959B2 - 6- (1-Fluoroethyl) -5-iodo-4-aminopyrimidine derivative, its production method and pesticide for agricultural and horticultural use - Google Patents

Description

[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative useful as a pest control agent for agriculture and horticulture.
[0002]
[Prior art]
The 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative of the present invention is a novel compound and is not known to have pest control activity for agriculture and horticulture.
[0003]
[Problems to be solved by the invention]
An object of the present invention is to provide a novel 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative, a production method thereof, and an agricultural and horticultural pest control agent comprising the same as an active ingredient. .
[0004]
[Means for Solving the Problems]
As a result of investigations to solve the above-mentioned problems, the present inventors have found that novel 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivatives are remarkable for agricultural and horticultural insecticides, acaricides, It discovered that it has a nematicidal and bactericidal activity, and completed this invention.
That is, the present invention is as follows.
The first invention is the following formula (1):
[0005]
[Formula 4]
[0006]
(In the formula, Ar represents 1 to 3 halogen atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and the number of carbon atoms. Represents a phenyl group, a naphthyl group, a thienyl group, an indanyl group or a 1,4-benzodioxan-6-yl group which may be substituted with 1 to 4 haloalkoxy groups or phenoxy groups; R represents a hydrogen atom, a carbon atom; Represents an alkyl group having 1 to 4 carbon atoms; "* 1" represents an asymmetric carbon atom; "* 2" represents an asymmetric carbon atom when R is an alkyl group having 1 to 4 carbon atoms. )
6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative represented by formula (1).
The second invention is the following formula (2):
[0007]
[Chemical formula 5]
[0008]
(In the formula, “* 1” has the same meaning as described above.)
4-chloro-6- (1-fluoroethyl) -5-iodopyrimidine represented by the following formula (3):
[0009]
[Chemical 6]
[0010]
(In the formula, Ar, R and “* 2” are as defined above.)
It is related with the manufacturing method of the 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative shown by said Formula (1) characterized by making it react with amines shown by these.
The third invention relates to an agricultural and horticultural pest control agent comprising a 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative represented by the above formula (1) as an active ingredient. .
[0011]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
The various substituents represented by the respective compounds are as follows.
Ar is 1 to 3 halogen atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. A phenyl group, a naphthyl group, a thienyl group, an indanyl group or a 1,4-benzodioxan-6-yl group which may be substituted with a haloalkoxy group or a phenoxy group.
R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
“* 1” is an asymmetric carbon atom.
“* 2” is an asymmetric carbon atom when R is an alkyl group having 1 to 4 carbon atoms.
[0012]
As a halogen atom which is a substituent in Ar, a chlorine atom, an iodine atom, a bromine atom, a fluorine atom, etc. can be mentioned, and a chlorine atom and a fluorine atom are preferable.
Examples of the alkyl group having 1 to 4 carbon atoms as a substituent in Ar include a linear or branched alkyl group, and a methyl group, an ethyl group, an isopropyl group, and a t-butyl group are preferable.
Examples of the haloalkyl group having 1 to 4 carbon atoms which is a substituent in Ar include difluoromethyl, trifluoromethyl group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, and the like. A trifluoromethyl group is preferred. .
As a C1-C4 alkoxy group which is a substituent in Ar, a linear or branched thing can be mentioned, A methoxy group and an ethoxy group are preferable. .
Examples of the haloalkoxy group having 1 to 4 carbon atoms as a substituent in Ar include a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, and a 2-fluoroethoxy group. Difluoromethoxy group and trifluoromethoxy group are preferable.
[0013]
Examples of the phenoxy group as a substituent in Ar include the above-described halogen atom, alkyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, carbon A phenoxy group which may be substituted with a haloalkoxy group having 1 to 4 atoms can be exemplified, and an unsubstituted phenoxy group is preferred.
As these substitution numbers, 1 to 3 are preferable.
Examples of the alkyl group having 1 to 4 carbon atoms in R include a linear or branched alkyl group, and include a methyl group, an ethyl group, an i-propyl group, an n-butyl group, and an i-butyl group. Is preferred.
[0014]
Since the compound (1) of the present invention has an amino group, an acid addition salt derived therefrom is also included in the present invention.
Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid; formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconitic acid. Carboxylic acid of sulfonic acid such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; saccharin and the like.
[0015]
In addition, since the compound (1) of the present invention contains asymmetric carbon atoms represented by “* 1” and “* 2”, individual optical isomers, racemates, diastereomers, or the like derived therefrom Any of these mixtures are included in the present invention.
[0016]
Among the compounds (1) of the present invention, particularly preferable compounds include the following.
(1) A compound in which R is a hydrogen atom and Ar is a phenyl group substituted with an alkoxy group having 1 to 4 carbon atoms. Examples thereof include compounds 5 and 6 described in Table 1 described later.
(2) A compound in which R is a hydrogen atom, and Ar is a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms. For example, compounds 1, 2, and 11 described in Table 1 described later can be exemplified.
(3) A compound in which R is a hydrogen atom and Ar is a phenyl group substituted with a phenoxy group. For example, the compound 12 described in Table 1 described later can be exemplified.
(4) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is an unsubstituted phenyl group. Examples thereof include compounds 13 to 18 described in Table 1 described later.
(5) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is a phenyl group substituted with a haloalkoxy group having 1 to 4 carbon atoms and a halogen atom. For example, the compound 22 described in Table 1 described later can be exemplified.
(6) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is a phenyl group substituted with a haloalkoxy group having 1 to 4 carbon atoms. For example, the compound 23 described in Table 1 described later can be exemplified.
(7) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is a phenyl group substituted with a halogen atom. Examples thereof include compounds 24 and 25 described in Table 1 described later.
(8) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms. Examples thereof include compounds 27 and 28 described in Table 1 described later.
(9) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is an unsubstituted indanyl group. For example, the compound 37 etc. which were described in Table 1 mentioned later can be mentioned.
(10) A compound in which R is an alkyl group having 1 to 4 carbon atoms, and Ar is an unsubstituted 1,4-benzodioxan-6-yl group. For example, the compound 39 etc. which were described in Table 1 mentioned later can be mentioned.
[0017]
The method for synthesizing the compound (1) of the present invention will be described in more detail.
(Synthesis method)
Compound (1) is synthesized by reacting compound (2) and compound (3) in a solvent in the presence of a base.
[0018]
The type of the solvent is not particularly limited as long as it does not directly participate in this reaction. For example, benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, chloroform, dichloroethane, Chlorinated or non-chlorinated aromatic, aliphatic, alicyclic hydrocarbons such as trichloroethylene; Ethers such as tetrahydrofuran, thioxane, diethyl ether, etc .; Nitriles such as acetonitrile, propionitrile, etc. Ketones such as acetone, methyl ethyl ketone, etc .; aprotic polar solvents such as N, N-dimethylformamide, dimethyl sulfoxide, sulfolane, N, N-dimethylimidazolidinone, N-methylpyrrolidone, and the like; Mixing And the like.
[0019]
The amount of the solvent used can be such that the compound (2) is 5 to 80% by weight; however, it is preferably 10 to 70% by weight.
Although the kind of base is not specifically limited, An organic base and an inorganic base are mentioned. For example, tertiary amines such as triethylamine, organic bases such as DBU, and hydrides of alkali metals or alkaline earth metals, inorganic bases such as hydroxides, carbonates, bicarbonates, etc. Organic bases are preferred.
1-5 times mole is preferable with respect to a compound (2), and, as for the usage-amount of a base, 1.2-2.0 times mole is more preferable.
[0020]
Although reaction temperature is not specifically limited, The inside of the temperature range below the boiling point of the solvent to be used from room temperature is preferable, and 60-110 degreeC is especially preferable.
The reaction time varies depending on the concentration and temperature, but is usually 0.5 to 8 hours.
As for the usage-amount of a raw material compound, it is preferable that a compound (3) is 1.0-5 times mole with respect to a compound (2), and 1-1.1 times mole is more preferable.
The compound (2) used in the present invention can be produced by a method represented by the following formula according to the description in Japanese Patent Application No. 2000-384776.
[0021]
[Chemical 7]
[0022]
(In the formula, “* 1” has the same meaning as described above.)
Compound (4) can be produced, for example, by the method shown in the following formula according to the method described in JP-A-11-171834.
[0023]
[Chemical 8]
[0024]
Compound (3) may be a commercially available product, or can be produced by the method shown in the following formula.
[0025]
[Chemical 9]
[0026]
(In the formula, Ar, R and “* 2” are as defined above.)
The target compound (1) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after completion of the reaction and, if necessary, by known means such as recrystallization and various chromatography. It can be refined properly.
[0027]
[Control effect]
Examples of agricultural and horticultural pests that are effective in controlling the compound (1) of the present invention include agricultural and horticultural pests [eg, Hemiptera (planthoppers, leafhoppers, aphids, whiteflies, etc.), Lepidoptera (Coleoptera) , Longhorn beetles, snails, beetles, cabbage, etc.), Coleoptera (Bombugidae, Weevil, beetles, Scarabaeidae, etc.) )], Nematodes (such as root-knot nematodes, cyst nematodes, nestle nematodes, singale nematodes, pine wood nematodes, etc.), mites, sanitary pests (eg, flies, mosquitoes, cockroaches, etc.), storage pests (eg, bryophytes, legumes) ), Wood pests (eg, termites, Yamato termites, Examples include termites such as scallop termites, slat beetles, beetles, beetles, beetles, bark beetles, etc., and horticultural pathogens (for example, wheat rust, barley powdery mildew, cucumber downy mildew) , Rice blast, tomato plague, etc.).
[0028]
[Pesticides]
The agricultural and horticultural pest control agent of the present invention is particularly effective in insecticidal / miticidal and nematicidal effects, and contains at least one compound (1) as an active ingredient.
The compound (1) can be used alone, but usually contains a carrier, a surfactant, a dispersant, an auxiliary agent and the like (for example, powders, emulsions, fine granules, granules, hydration) by a conventional method. Prepared as a composition such as an agent, an oily suspension, and an aerosol).
[0029]
Examples of the carrier include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic hydrocarbons (benzene) , Toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene glycol acetate, Liquid carriers such as dibutyl maleate), alcohols (methanol, n-hexanol, ethylene glycol, etc.), aprotic polar solvents (dimethylformamide, dimethyl sulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection) out and the like.
[0030]
Surfactants and dispersants that can be used to improve the performance of adhesion and absorption of this agent to animals and plants, dispersion, emulsification, and spreading of drugs include alcohol sulfates, alkylsulfonates, and lignin. Examples thereof include sulfonates and polyoxyethylene glycol ethers. For example, commercially available products such as Neoperex powder (trade name; manufactured by Kao Corporation), Demol (trade name; manufactured by Kao Corporation), and Toxanone (trade name; manufactured by Sanyo Chemical Industries) can be used. And in order to improve the property of the formulation, carboxymethylcellulose, polyethylene glycol, gum arabic etc. can be used as an auxiliary agent, for example.
In the preparation of this agent, the above-mentioned carrier, surfactant, dispersant and adjuvant can be used alone or in appropriate combination depending on the purpose.
[0031]
The active ingredient concentration when the compound (1) of the present invention is formulated is usually 1 to 50% by weight for emulsions, usually 0.3 to 25% by weight for powders, and usually 1 to 90% by weight for wettable powders. It is usually 0.5 to 5% by weight for agents, 0.5 to 5% by weight for oils, and 0.1 to 5% by weight for aerosols.
These preparations can be used for various purposes by diluting them to an appropriate concentration and spraying them on the surface of plant foliage, soil and paddy fields, or applying them directly according to their purpose.
[0032]
【Example】
Hereinafter, the present invention will be specifically described with reference examples and examples. These do not limit the scope of the present invention.
Reference Example 1 [Synthesis Method of Compound (5)]
Synthesis of 6- (1-fluoroethyl) -4-pyrimidone 4-fluoro-3-oxopentanoic acid methyl ester (93.3 g) was dissolved in methanol (1000 ml), and 28% sodium methylate / methanol solution (365 g) And formamidine acetate (98.4 g) were sequentially added, and the mixture was heated to reflux at 40 ° C. for 12 hours.
After completion of the reaction, the mixture was cooled to 10 ° C. or lower, and a mixed solution of concentrated sulfuric acid (95.1 g) and water (85 g) was added. Subsequently, the mixture was stirred at 50 ° C. for 30 minutes, insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from isopropanol to obtain 58 g of the objective compound as colorless crystals.
m. p. 170.0-171.5 ° C
[0033]
Reference Example 2 [Synthesis Method of Compound (6)]
Synthesis of 6- (1-fluoroethyl) -5-iodo-4-pyrimidone Iodine chloride (50.8 g) was added to acetic acid (500 ml) and chlorine (15 g) was blown into the mixture with stirring at room temperature. Was added dropwise to a solution of 6- (1-fluoroethyl) -4-pyrimidone (56.8 g) in acetic acid (150 ml) with stirring at room temperature, and stirred for 6 hours.
After completion of the reaction, acetic acid is distilled off under reduced pressure, water (300 ml) is added and dissolved, and the pH is adjusted to 5 with 2N sodium hydroxide and saturated aqueous sodium hydrogen carbonate solution. The precipitated crystals were collected by filtration, washed with water and dried to obtain 85 g of the desired product as pale ocher crystals.
Further, purification by recrystallization with ethyl acetate-hexane gave 76.0 g of the target compound as colorless small needle crystals.
m. p. 195-196 ° C
[0034]
Reference Example 3 [Synthesis Method of Compound (2)]
Synthesis of 4-chloro-6- (1-fluoroethyl) -5-iodopyrimidine 6- (1-fluoroethyl) -5-iodo-4-pyrimidone (53.6 g) was added to ethyl acetate (180 ml) and N , N-dimethylformamide (1.5 g) is added, and the mixture is heated to 70 ° C. with stirring. Subsequently, thionyl chloride (28.6 g) was added dropwise and stirred for 3 hours to complete the reaction.
After cooling the reaction mixture, it was added to ice-cold water, adjusted to pH 4 with 2N sodium hydroxide, the ethyl acetate layer was separated, washed with water, and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled off under reduced pressure, and the obtained residue was purified by distillation under reduced pressure to obtain 54.6 g of the desired product as a pale yellow liquid.
b. p. 116-118 ° C / 4mmHg
[0035]
Example 1 [Synthesis Method of Compound (1)]
(1) Synthesis of 4- (4-t-butylbenzylamino) -6- (1-fluoroethyl) -5-iodopyrimidine (Compound 1) 4-t-butylbenzylamine (0.8 g) and triethylamine (0 6 g) was dissolved in 20 ml of toluene, 4-chloro-6- (1-fluoroethyl) -5-iodopyrimidine (1.5 g) was added, and the mixture was heated and stirred at about 80 ° C. for 3 hours.
After completion of the reaction, triethylamine hydrochloride was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (Wakogel C-200, developing solvent: n-hexane / ethyl acetate = 3/1). By purification, 1.5 g of the desired product which was a colorless platelet crystal was obtained.
[0036]
m. p. 114-115 ° C
¹ H-NMR (CDCl ₃ , δ ppm)
1.32 (9H, s), 1.61-1.71 (3H, dd),
4.68 to 4.70 (2H, d), 3.74 to 3.81 (2H, q),
5.70-5.92 (1H, dq), 5.76 (1H, b),
7.26-7.41 (4H, m), 8.50 (1H, s)
[0037]
(2) Synthesis of 6- (1-fluoroethyl) -5-iodo-4- (α-methylbenzylamino) pyrimidine (Compound 13) α-methylbenzylamine (1.2 g) and triethylamine (1.2 g) It melt | dissolved in 40 ml of toluene, 4-chloro-6- (1-fluoroethyl) -5-iodopyrimidine (2.9 g) was added, and it heated and stirred at about 80 degreeC for 3 hours.
After completion of the reaction, triethylamine hydrochloride was filtered off, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (Wakogel C-200, eluent: n-hexane / ethyl acetate = 3/1 elution). To obtain 2.9 g of the desired product which is a pale orange viscous liquid.
[0038]
¹ H-NMR (CDCl ₃ , δ ppm)
1.57 to 1.69 (6H, m), 4.68 to 4.70 (2H, d),
5.24-5.92 (1H, dq), 5.83 (1H, b),
7.24-7.37 (5H, m), 8.43 (1H, s)
[0039]
(3) Synthesis of other compounds (1) in Tables 1 to 3 Other compounds (1) in Tables 1 to 3 were synthesized according to the methods described in (1) and (2) above.
The compounds (1) synthesized as described above and their physical properties are shown in Tables 1-3.
“* 1” is all a racemate (R, S).
[0040]
[Table 1]
[0041]
[Table 2]
[0042]
[Table 3]
[0043]
Example 2 [Preparation of formulation]
(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 After mixing uniformly, a small amount of water was added and kneaded, then granulated and dried to obtain granules.
[0044]
(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 neopelex powder (trade name; manufactured by Kao Corporation) and demole (trade name) A product of Kao Co., Ltd.) 0.5 parts by weight was uniformly mixed and then pulverized to obtain a wettable powder.
[0045]
(3) Preparation of Emulsion To 20 parts by weight of Compound (1) and 70 parts by weight of xylene, 10 parts by weight of Toxanone (trade name; manufactured by Sanyo Chemical Industries) was added and mixed uniformly and dissolved to obtain an emulsion.
[0046]
(4) Preparation of powder A powder was obtained by uniformly mixing 5 parts by weight of compound (1), 50 parts by weight of talc and 45 parts by weight of kaolin.
[0047]
Example 3 [Efficacy test]
(1) Efficacy test against stink bug Each wettable powder of compound (1) shown in Tables 1 to 3 prepared according to Example 2 was diluted to 1000 ppm with water containing a surfactant (0.01%). Cabbage leaf pieces (5 cm × 5 cm) were soaked in each chemical solution for 30 seconds, put one by one in each plastic cup, and air-dried.
Next, 10 caterpillars (3rd instar larvae) are released in these cups, covered, and left in a constant temperature room at 25 ° C. After 2 days, the number of live and dead insects in each cup is counted to determine the death rate. It was.
As a result, Compounds 1-8, 11-18, 20-29, 33, 36, 37, 39 showed an insecticidal activity of 80% or more.
[0048]
(2) Efficacy test against peach aphid Each wettable powder of compound (1) shown in Tables 1-3 prepared according to Example 2 was diluted to 100 ppm with water containing a surfactant (0.01%). Cabbage leaf pieces (5 cm × 5 cm) were soaked in each of these chemical solutions for 30 seconds, put one by one in each plastic cup, and air-dried.
Next, 10 peach aphids (adult female adults) were released in these cups, covered, and allowed to stand in a constant temperature room at 25 ° C. After 3 days, life and death of adult females and larvae in each cup The number was counted to determine the death rate.
As a result, the compounds 6, 11 to 14, 16, 22 to 25, 27, 28, 37 and 39 showed an insecticidal activity of 80% or more.
[0049]
(3) Antibacterial test A plate solution was prepared by mixing an acetone solution of the compound (1) shown in Tables 1 to 3 in a PDA (potato dextrose agar) medium to a final concentration of 40 ppm.
The flora of Prunus ash rot and rice blast fungus previously grown on a PDA plate medium was cut into 1 mm squares with a scalpel and inoculated into the prepared plate medium with a drug.
The cells were cultured at 25 ° C. in the dark for 3 days, the drug-free group and the flora diameter were compared, and the fungus growth inhibition rate (%) was determined by the following formula.
[0050]
[Expression 1]
[0051]
Judgment of the effect is 5 to 100%, 5 to 85 to 95%, 4 to 85 to 70%, 3 to 45 to 70%, 2 to 10 to 45, and 0 to 10 to 0%. As mentioned above, it was performed in 6 stages of 5-0.
As a result, the compounds 2-8, 11-18, 20-29, 33, 36, 37, 39 show effects of 4 or more against the plum blight fungus, and the compounds 1-8, 11 against rice blast fungus. 18, 20-29, 33, 37, 39 showed an effect of 4 or more.
[0052]
【The invention's effect】
The novel 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative of the present invention has an excellent agricultural and horticultural pest control effect.

Claims (4)

The following formula (1):
(In the formula, Ar represents 1 to 3 halogen atoms, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and the number of carbon atoms. Represents a phenyl group, a thienyl group , an indanyl group or a 1,4-benzodioxan-6-yl group which may be substituted with 1 to 4 haloalkoxy groups or phenoxy groups; R represents a hydrogen atom, a carbon atom number of 1 to 4 alkyl groups; “* 1” represents an asymmetric carbon atom; “* 2” represents an asymmetric carbon atom when R is an alkyl group having 1 to 4 carbon atoms). 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative.   Ar is 4-difluoromethoxyphenyl and R is —CH ₃ The 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative represented by the formula (1) according to claim 1. Formula (2):
(Wherein “* 1” has the same meaning as described in claim 1) and 4-chloro-6- (1-fluoroethyl) -5-iodopyrimidine represented by the following formula (3):
(Wherein Ar, R and “* 2” have the same meanings as described in claim 1), and reacting with an amine represented by formula (1) according to claim 1 or 2 , Preparation of the indicated 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative. Pesticide containing as an active ingredient 6- (1-fluoroethyl) -5-iodo-4-aminopyrimidine derivative represented by the formula (1) according to claim 1 or 2.