JPH03200783A - Pyrimidine-based compound, production thereof and noxious organism controlling agent containing the same - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I {R<1> is H or alkyl; R<2> and R<4> are 6-chloro-3-pyridylmethyl, H or alkyl; R<3> is alkyl or formula II [X is H, halogen, (halogen-substituted) alkyl or (halogen-substituted alkoxy; R<5> is H or alkyl; n is 0 or 1], provided that R<4> is H or alkyl when R<2> is 6-chloro-3- pyridylmethyl and 6-chloro-3-pyridylmethyl when R<2> is H or alkyl}. EXAMPLE:6-[N-(6-Chloro-3-pyridylmethyl)-N-methylamino]-3-(4-fluorobenz yl)-1- methyl-5-nitro-1,2,3,4-tetrahydropyrimidine. USE:A noxious organism controlling agent. PREPARATION:A compound expressed by formula III is reacted with a compound expressed by the formula H2N-R<3> and formaldehyde.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to novel pyrimidine compounds, methods for producing them, and pest control agents containing them.

(Prior art and background to the invention) As a pyrimidine compound, for example, JP-A-1-160
It is known from Japanese Patent No. 981 that it is useful as an active ingredient of pest control agents. However, the above publication does not disclose the compound of the present invention.

The present invention is based on the knowledge that certain pyrimidine compounds exhibit high pesticidal effects.

(Disclosure of the Invention) The present invention relates to pyrimidine compounds represented by the following general formula (I) or salts thereof, methods for producing them, and pest control agents containing them.

General formula (I) (wherein, R1 is a hydrogen atom or an alkyl group, R2 and R4 are a 6-chloro-3-pyridylmethyl group, a hydrogen atom or an alkyl group, and R3 is an alkyl group or a hydrogen atom, an alkyl group that may be substituted with a halogen atom or an alkoxy group that may be substituted with a halogen atom, R5 is a hydrogen atom or an alkyl group, and n is 0 or l, provided that R2 is 6 -When R1 is a hydrogen atom or an alkyl group, R4 is a 6-chloro-3-pyridylmethyl group) In general formula (I) , R', R'', Rko, R4, R
The alkyl group contained in 8 and X and the alkyl moiety of the alkoxy group contained in
Examples include pendel group, hexyl group, etc., and they also include structural isomers of straight or branched aliphatic chains.

Examples of the halogen atom contained in X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Furthermore, when the number of halogen atoms substituted in the alkyl group which may be substituted with a halogen atom and the alkoxy group which may be substituted with a halogen atom represented by X is two or more, they may be of the same kind or different kinds. good.

Examples of the salt of the compound represented by the general formula (I) include salts with acidic substances, such as inorganic acid salts such as hydrochloride, hydrobromide, phosphate, sulfate, and nitrate; Acetate, oxalate, malonate, succinate, malate, tartrate, maleate, fumarate, benzoate, chloroacetate, trichloroacetate, phthalate, nicotinate. Examples include organic carboxylates such as citrate and ascorbate; sulfonates such as methanesulfonate, toluenesulfonate, benzenesulfonate, and naphthalenesulfonate.

The compound represented by the general formula (I) can be produced, for example, by the following method.

[Reaction step a]

l (II) (III)4 (wherein R1, R1, R3 and R4 are as described above) Reaction step a is usually carried out in the presence of a diluent. Examples of the diluent include solvents that are inert to the reaction,
For example, water; pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride,
Aliphatic or aromatic hydrocarbons such as chloroform, carbon tetrachloride, chlorobenzene, O-dichlorobenzene; ethers such as diethyl ether, dibutyl ether, glycol dimethyl ether, diglycol dimethyl ether, tetrahydrofuran, dioxane; acetonitrile, dimethylformamide , aprotic polar solvents such as dimethyl sulfoxide; alcohols such as methanol, ethanol, n-probanol, and impropanol; varnishes and chillers such as ethyl acetate and methyl acetate; can be used alone or as a mixture, but a mixed solvent of water and alcohol is particularly desirable. Also, reaction step a may be carried out in the presence of a catalyst if necessary. As a catalyst, hydrochloric acid, hydrobromic acid, etc. Examples include non-oxidizing acid catalysts such as hydrohalic acid; phosphoric acid; lower fatty acids such as acetic acid and propionic acid. The reaction temperature in reaction step a is usually -20 to +120°C, preferably 0 to 80°C. ℃, and the reaction time is 0.1 to 24 hours.

In addition, in the reaction step a, the compound represented by the general formula (I [) 1-
1.5 mol, preferably 1-1.2 mol, and formaldehyde 2-4 mol, preferably 2-3 mol are used.

The formaldehyde used in reaction step a is usually an aqueous solution, but paraformaldehyde in step (a) can also be used.

In the compound represented by the general formula (1), the compound in which R1 is a hydrogen atom is preferably produced by the following method.

[Reaction step b]

(IV) (1-1) (In the formula, R2, R3 and R4 are as described above) The reaction step is usually carried out in the presence of a diluent, and the diluent is the one used in the reaction step a. The reaction temperature of the 0 reaction step is usually -20 to +
The temperature is 120°C, preferably 0 to 80°C, and the reaction time is 0.
．． 1 to 24 hours.

In the reaction step, the compound represented by the general formula (■) can be produced, for example, by the following method.

[Reaction step C]

(In the formula, R2 and R3 are as described above) Reaction step C
is usually carried out in the presence of a diluent, and examples of the diluent include those similar to those used in reaction step a. The reaction temperature in reaction step C is usually -20 to +120°C, preferably 0 to +120°C. The temperature was 80°C, and the reaction time was 0.1 to 24
It's time.

Next, specific synthesis examples of the compounds of the present invention will be described.

Synthesis Example 1 6-(N-(6-chloro-3-pyridylmethyl)-N
-methylamino)-3-(4-fluorobenzyl)-1
-Synthesis of methyl-5-nitro-1,2,3,4-tetrahydropyrimidine (compound Na1) 1- (N-(6-chloro-3-pyridylmethyl)-N
-methylamino)-1-methylamino-2-nitronylene 0.72 g (2,8 gu+oA) of methanol 10a+I! solution, 4-fluorobenzylamine 0.3
8 g (3 smol) and 0.51 g (6++++ ao1) of 35% formaldehyde aqueous solution were mixed, and 2
．． After the reaction was heated under reflux for 5 hours, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to give a melting point of 190-192.
0.95 g (yield: 84%) of the desired product (yellow crystals, 1 kl of compound) was obtained.

Synthesis Example 2 6-(N-(6-chloro-3-pyridylmethyl)amino)-3-(4-fluorobenzyl>-1-methyl-5-
Synthesis of nitro 1.2.3.4-tetrahydropyrimidine (compound profile 2) (l) 4.44 g of 2-methylamino-2-methylthio-1-nitroethylene (30++unoI, 4-
Fluorohensylamine 3.75 g (30 majo
l), 5.14 g of 35% formaldehyde aqueous solution (60
mmol) and 30IIIl of ethanol,
The mixture was heated under reflux for 30 minutes. After the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, ethyl acetate:hexane = 1:1) to obtain 3-(4-fluorobenzyl)-1 with a melting point of 98-104°C.
-Methyl-6-methylthio-5-nitro-1,2,3,
4-tetrahydropyrimidine (yellow crystals, intermediate tkl
) 5.87g was obtained.

(Yield 66%) (2) 3-(4-fluorobenzyl)-1-methyl-6-methylthio-5-nitro- obtained in step (1)
2.97 g of 1,2,3,4-tetrahydropyrimidine
(10 mmof), 1-43 g of 5-chloro-3-pyridylmethylamine (10 mmof) and 5 ml of ethanol were mixed and heated under reflux for 35 minutes. After the reaction was completed, ethanol was distilled off under reduced pressure, and column chromatography (developing Using a solvent (methanol:ethyl acetate=5:95), 0.57 g of the desired product (colorless to pale yellow crystals, compound 11h2) having a melting point of 150 to 154°C was obtained.

Synthesis Example 3 l-(6-chloro-3-pyridylmethyl)-6-dimethylagono-3-(4-fluorobenzyl)-5-nitro-1,2,3,4-tetrahydropyrimidine (compound M
Synthesis of 32) 1-(6-chloro-3-pyridylmethyl)amino-1-
Dimethylamino-2-nitroethylene 1.0 g (3
, 9mn+ojri, 4-fluorohensylamine 0.
42 g (3.9mm), 0.67 g (7,8a++) of 35% aqueous formaldehyde solution and 10ml of methanol were mixed and heated under reflux for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. Purification by chromatography (developing solvent, methanol:dichloromethane = 1:19) gave a melting point of 140-143.
1.10 g of the target product (compound N1132) was obtained.

Synthesis Example 4 6-(N-(6-chloro-3-pyridylmethyl)agono)-3-(2-fluorobenzyl)-1=methyl-5
-nitro-1,2,3,4-tetrahydropyrimidine (
Synthesis of compound magnetokinetic 16〉 (1) 2-methylano 2-methylthio-1-ditopenic ethylene 2.96 g (20m+nof), 2-fluorobenzylamine 2.50 g (20auno
l), 3.43 g of 35% formaldehyde aqueous solution (40
After the reaction, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate: n-hexane = 2: 3). melting point 7
2.20 g of 3-(2-fluorobenzyl)-1-methyl-6-methylthio-5-ditro-1.2.3.4-tetrahydropyrimidine (Intermediate 4) was obtained at 6-8°C.

(2) 3-(2-fluorobenzyl)-1-methyl-6-methylthio-5nitro-1 obtained in the above step (1)
,2,3,4-tetrahydropyrimidine (intermediate 4)
2.08 g (7,0 old 01), 6-chloro-3-
Viridyl methyla straw 1. Og (7.0 mmol) and methanol 20+++jF were mixed and heated under reflux for 30 minutes. After the reaction, methanol was distilled off under reduced pressure and subjected to silica gel column chromatography (developing solvent: ethyl acetate).
Purify the target product with a melting point of 147-149°C (combined magnetic flux 1
6) Obtained 0.85g.

Synthesis Example 5 6-(N-(6-chloro-3-pyridylmethyl)amino)-1,3-dimethyl-5-nitro-1,2°3.
Synthesis of 4-tetrahydropyrimidine (compound N1121) (1) 2-methylamino-2-methylthio-1-nitroethylene 2.96 g (20o+moj), 35% formaldehyde aqueous solution 3.43 g (40majol)
) and methanol 20 mff1 at room temperature.
1.55 g (20 mj) of 0% methylamine solution was added and stirred at room temperature for 20 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent: methanol: ethyl acetate = 1: 9) to obtain 1.48 g of 1,3-dimethyl-6-methylthio-5-nitro-1,2,3,4-tetrahydropyrimidine (intermediate Na8) having a melting point of 67-69°C.

(2) 1, 3 that can be obtained by the method of step (1) above
-dimethyl-6-methylthio-5-nitro1.2゜3
．． 4-tetrahydropyrimidine (intermediate Na8) 1.2
A mixture of 2 g (6a+moj, 5-chloro-3-pyridylmethylaminel 10+sj!) was heated to reflux for 30 minutes.

After the reaction is complete, methanol is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography to give a melting point of 133~
0.55 g of the target product (compound M21) was obtained at 136°C.

Representative examples of the intermediate compounds expressed in mV are listed in Table 1.

Table 2 (Continued) Next, representative examples of the compounds represented by the general formula (I) are listed in Table 2.

Table (2) Table (tlfE) The compound of the present invention exhibits excellent activity as an active ingredient of a pest control agent.

For example, two-spotted spider mite, false two-spotted spider mite, orange spider mite,
Plant-parasitic mites such as bed mites, mealybugs, armyworms, fall armyworms, codling moths, ballworms, tobacco budworms, gypsy moths, Colorado potato beetles, cucumber beetles, poleweevils, aphids, planthoppers,
Agricultural pests such as leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, wasp flies, scarab beetles, yellowtail moths, cutworms, ants, etc.; hygiene such as dust mites, cockroaches, houseflies, Culex mosquitoes; Pests, grain storage pests such as bur moths, adzuki bean weevils, small bean weevils, mealworms, etc., clothing and house pests such as burs, burrs, termites, etc., fleas that parasitize livestock, etc.
It is effective against lice, flies, etc., and is also effective against plant-parasitic mites such as cat nematodes, cyst nematodes, white nematodes, rice nematodes, strawberry nematodes, pine tree nematodes, etc. It is also effective. It is also effective against soil pests. The soil pests mentioned here include slugs,
Examples include gastropods such as snails, and isopods such as pill bugs and flaming beetles. Furthermore, it is effective against pests such as dicofol (trade name: manufactured by Narita Pharmaceutical Co., Ltd. (TL)) and organophosphate-resistant plant parasitic mites, organophosphate-resistant aphids, and house flies.Furthermore, the present invention Since the compound has excellent permeability, by treating the soil with the compound of the present invention, it can be used to control soil harmful insects, mites, nematodes, gastropods, and isopods while simultaneously It can also control pests.

When using the compound of the present invention as an active ingredient of a pest control agent, it can be used in combination with agricultural chemical adjuvants such as emulsions, powders, granules, wettable powders, liquids, aerosols, pastes, etc., as in the case of conventional pesticide formulations. It can be formulated into various forms. The mixing ratio of these ingredients is usually 0.5 to 90 parts by weight of the active ingredient and 10 to 99.5 parts by weight of the pesticide auxiliary. When actually using these preparations, either use them as is or
Alternatively, it can be used after being diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliaries mentioned here include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrating agents, wetting agents, thickeners, stabilizers, etc., and may be added as appropriate if necessary. They are divided into solid carriers and liquid carriers. Solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, and diatomaceous earth. Examples of liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone and methyl ethyl ketone, dioxane,
Ethers such as tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, and solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene, dimethyl Examples include acids such as formamide, esters such as ethyl acetate and glycerin ester of fatty acids, nitrites such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

In addition, if necessary, it can be mixed or used in combination with other agricultural chemicals, such as insecticides, miticides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc. In this case, even better effects may be obtained.

For example, as an insecticide, acaricide, or nematicide,
O-(4-bromo-2-chlorophenyl)0-ethyl S
-propyl phosphorothioate, 2,2-dichlorovinyl, dimethyl phosphate, ethyl 3-methyl-4-(
Methylimino〉Phenyl isopropyl phosphoroamidate, 0.0-dimethyl 0-4-nitrom-1lyl phosphorothioate, 〇-ethyl 0-4-nitrophenylphenylphosphonothioe-1, 0.0-diethyl 0 -2
-isopropyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0-dimethyl O-(3,5,6-
Dolichloro-2-pyridyl) phosphorothioate, 0.
5-dimethylacetylphosphoramidothioate, 0-
(Organophosphate ester compounds such as 2,4-dichlorophenyl〇-ethyl S-propyl phosphorodithioate; 1-naphthylmethyl carbamate, 2-isopropoxyphenylmethyl carbamate, 2-methyl-
2-(Methylthio)propionaldehyde O-methylcarbamoyloxime, 2,3-dihydro-2,2-dimethylbenzofuran-7-ylmethylcarbamate, dimethyl N,N-(thiobis[(methylimino)carbonyloxy])bisethanimide Thioate, S-methyl N
-(Methylcarbamoyloxy)thioacetoigodate, N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenylmethylcarbamate, 2-dimethylamino-5.6- Carbamate compounds such as dimethylpyrimidin-4-yldimethylcarbamate, S,S-2-dimethylaminotrimethylenebis(thiocarbament), 2.2.2-)dichloro-1,1-
Organochlorine compounds such as bis(4-chlorophenyl)ethanol and 4-chlorophenyl-2,4,5-dichlorophenylsulfone; organometallic compounds such as tricyclohexyltine hydroxide; (RS)-α-cyano- 3-phenoxybenzyl (R5) -2-(4-chlorophenyl)-3-methylbutyrate, 3-phenoxybenzyl (IRS) cis, trans-3-(2,2-
dichlorovinyl) 2.2 dimethylcyclopropane, (RS)-α-cyano-3-phenoxybenzyl (IRS)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane Carboxylate, (S)-α-cyano-3-phenoxybenzyl (IR)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate, (RS)-α-cyano- 3-phenoxybenzyl (
IRS)-cis, trans-3-(2-crot:l-3
1313-1-IJ fluoropropenyl)-2,2 dimethylcyclopropane carboxylate, 4-methyl-2
,3,5,6-titrafluorobenzyl 3-(2-chloro-3,3,3-)lifluoro-1-propene-1-
-2,2-dimethylcyclopropanecarboxylic acid: 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, l-(3,5-dichloro-4- (3-chloro-5-
trifluoromethyl-2-pyridyloxy)phenyl)
-3-(2,6-difluorobenzoyl)urea, 1-
(3,5-dichloro-2,4-difluorophenyl>-
Benzoylurea compounds such as 3(2,6-difluorobenzoyl)urea; 2tert-butylimino-
3-isopropyl-5-phenyl-3,4,5゜6-titrahydro2H-1,3,5-thiadiazine-4-
trans-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidinone-3
- Compounds such as carboxylate, N-methylbis(2,4-xylyliminomethyl)amine; isopropyl (
2E, 4E) -11 = Juvenile hormone-like compounds such as methoxy-3,7,11-trimethyl-2,4-dodecagenoate; Other compounds include dinitro compounds, organic sulfur compounds, urea compounds, etc. compounds, triazine compounds, and the like. Furthermore, it can be mixed or used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.

For example, fungicides include S-benzyl, 0.0-diisopropyl, phosphorothioate, 〇-ethyl, S, S
- Organophosphorus compounds such as diphenylphosphorodithioate and aluminum ethyl hydrogen phosphonate; Organochlorine compounds such as 4,5,6.7-titrachlorophthalide and tetrachloroisophthalonitrile;
Manganese ethylene bis(dithiocarbamate) polymer, zinc ethylene bis(dithiocarbamate) polymer, zinc and maneb complex, didizinc bis(dimethyldithiocarbamate) ethylene bis(dithiocarbamate), zinc propylene bis(dithiocarbamate) dithiocarbamate compounds such as polymers of; 3
a, 4,7,7a-tetrahydro-N-(trichloromethylsulfenyl)phthalimide, 3a, 4.7,7a
N-halogenothioalkyl compounds such as -tetrahydro-N-(1,1,2,2-tetrachloroethylsulfenyl)phthalimide, N-(trichloromethylsulfenyl)phthalide: 3-(3,5-'; dichlorophenyl-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide, (RS) -3-(3
,5-dichlorophenyl)-5-methyl-5-vinyl-
1,3-oxazolidine-2,4-dione, N-(3,
Dicarboximide system formation i11 such as 5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide; methyl 1-(butylcarbamoyl)benzimidazole-2-yl-bamate, dimethyl 4
．． Benzimidazole compounds such as 4-(o-phenylene)bis(3-thioallophanate) 1f-(4
-chlorophenoxy)-3,3-dimethyl-1-(I
H-1,2,4-)riazol-1-yl)butanone,
1-(biphenyyl-4-yloxy)-3,3-dimethyl-1-(I H-1,2゜4-triazole-1-
yl)butan-2-ol, 1-(N-(4-chloro-2-trifluoromethylphenyl)-2-propoxyacetimidoyl]idendazole, 1-(2-(2,
4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl) -L H-1,2,4-triazole, 1-(2-(2,4-dichlorophenyl)
-4-propyl-1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole, 1-(2-
(2,4-dichlorophenyl>pentyl)-1H-1,
Azole compounds such as 2,4-triazole;2.
4'-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2,4-difluoro-
Carbinol compounds such as α-(l H-1,2,4-)lyazol-1-ylmethyl)benzhydryl alcohol; 3'-isopropoxy-o-1-ylanilide, α, α, α-trifluoro rho3'-isopropoxy-
Benzanilide compounds such as o-1-luanilide;
Methyl N-(2-methoxyacetyl)-N-(2,6-
phenylamide compounds such as xylyl)-DL-alaninate; 3-chloro-N-(3-chloro-2,6-
Sinitro 4-α, α, α-trifluorotrile〉-5
- Piricina ξ compounds such as trifluoromethyl-2-pyricinamon; Other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, and sulfenic acid compounds. , urea compounds, antibiotics, etc.

Application of the pesticidal agents of the present invention generally ranges from 1 to 20.0
The active ingredient concentration is desirably 20 to 2.0OOpps. These active ingredient concentrations can be changed appropriately depending on the form of the preparation, the method of application, purpose, timing, location, pest outbreak status, etc. In the case of harmful insects, it is possible to control harmful insects by spraying a chemical solution with the above concentration range to the place where they occur, so the concentration range of the active ingredient in water is below the above range. The application amount per unit area is about 0.1 to 5.000 g, preferably 10 to 1.000 g, of the active ingredient compound per 10 a. However, in special cases it is also possible to depart from these ranges.

Various formulations containing the compounds of the present invention or dilutions thereof can be applied by commonly used application methods, such as scattering (e.g., scattering, spraying, ξ sting, atomizing, dusting, water surface application, etc.); It can be carried out by soil application (mixing, irrigation, etc.), surface application (painting, dusting, coating, etc.), immersed poison bait, etc. It is also possible to feed the above-mentioned active ingredient to livestock by mixing it with their feed to control the emergence and growth of harmful insects, particularly harmful insects, in their excrement. In addition, the so-called ultra-high concentration small amount spraying method (ultra lowvol) is used.
It can also be applied by ume). In this way, 100% active ingredient content is possible.

l Soak rice seedlings in a chemical solution prepared to have an active ingredient concentration of 800 pp- for about 10 seconds, air dry, wrap the roots with moist absorbent cotton, and place in a test tube.Next, 10 larvae of the planthopper were placed in the test tube. Release the tube, cover the tube opening with gauze, and
It was left in a thermostat with lighting at 6°C. The survival rate was determined by the following formula.

Compounds 1-6, 15-21 and 32 showed 100% mortality.

2 The test was conducted in the same manner as in Test Example 1 above, except that the larvae of the brown planthopper were replaced with the larvae of the brown planthopper, and the mortality rate was determined.

Compounds Nll and 2 showed 100% mortality.

3. The test was conducted in the same manner as in Test Example 1 above, except that the larvae of the black-spotted leafhopper were replaced with the larvae of the black-spotted leafhopper, and the mortality rate was determined.

Compounds N111-6.15-21 and 32 showed 100% mortality.

4. Each preparation of the active ingredient compound of green leaf beetle was dispersed in water, and the concentration was adjusted to 800 ppm. Transplant only one eggplant leaf left into a cup (8 cm in diameter, 7 cm in height), and inject 2 to 3 viviparous female adults of the green peach aphid into this cup.
The head was inoculated and the pups were born. Two days after inoculation, the pests were removed and the number of larvae was counted. The eggplant leaves infested with these larvae were immersed in a chemical solution prepared at the above concentration for about 10 seconds, and then air-dried at 26°C.
It was left in a thermostat with lighting. The survival rate was determined at the 5th day after release, and the survival rate was calculated using the following formula. In addition, those who left were considered to have died.

Dead Insect Count Mortality Rate (%) = X100 Treatment Insect Count Compound Dynamics 1-3.5.15-21 and 32 showed a 100% mortality rate, and Compound No. 6 showed a 90% mortality rate.

5 Momo Power Aboomshi' - Each formulation of the active ingredient compound was dispersed in water and the concentration was adjusted to 800 ppm. An eggplant with only one leaf left was transplanted into a cup (diameter 8 cm, height 7 cm), inoculated with 2 to 3 viviparous female adults of the peach aphid, and spawned. Two days after inoculation, the insects were removed and the number of larvae was counted. The eggplants infested with larvae were treated with soil drenching treatment with chemical solution 10- prepared to the above-mentioned concentration, and left in a constant temperature chamber with lighting at 26°C. Five days after the treatment, survival was determined, and the survival rate was determined in the same manner as in Test Example 4 above. In addition, M
Escape was considered death.

Compound magnetokinetic l~3.5.16-21 and 32 showed a 100% mortality rate, and compound M4 showed a 95% mortality rate.

Disperse each formulation of the Hasmonyo active ingredient compound in water,
Cabbage leaf pieces were immersed in a chemical solution adjusted to a concentration of 0.000 ppm for about 10 seconds and air-dried. A Petri dish with a diameter of 9 cm was lined with moist filter paper, and the air-dried leaf pieces were placed on top of it. Ten 2nd to 3rd instar Spodoptera larvae were released there, the lid was placed, and the larva was left in a lighted incubator at 26°C. The survival rate was determined in the same manner as in Test Example 1, and the survival rate was determined on the 5th day after release.

Compounds 11h2.3.16-18 and 21 showed 100% mortality.

Next, formulation examples of the present invention will be described, but the compounds, compounding ratios, dosage forms, etc. of the present invention are not limited to the described examples.

Formulation Example 1 (A) Compound &2 20 parts by weight (1) Kaolin 72 parts by weight (3) Sodium ligninsulfonate 8 parts by weight or more are uniformly mixed to prepare a wettable powder.

Formulation Example 2 (a) Compound 1kl 5 parts by weight (b) Talc 95 parts by weight or more are mixed uniformly to form a powder.

Formulation Example 3 (a) Compound N115 20 parts by weight (b)
20 parts by weight of N,N'-dimethylformamide (c) Polyoxyethylene alkylphenyl ether
10 parts by weight (d)xylene
50 parts by weight or more are uniformly mixed and dissolved to form an emulsion.

Formulation Example 4 (a) Kaolin 68 parts by weight (b) Sodium ligninsulfonate 2 parts by weight (c) Polyoxyethylene alkylaryl sulfate
5 parts by weight (d) Fine powder silica 25
The mixture of each component in parts by weight or more and compound M3 are 4=1
Mix in weight proportions to form a wettable powder.

Formulation Example 5 (a) Compound 11m21 40 parts by weight (b) Oxylated polyalkylphenol phosphate-triethanolamine 2 parts by weight (c) Silicone 0.2 parts by weight (d)
Xanthan gum 0.1 parts by weight (e) Ethylene glycol 5 parts by weight (f) water
52.7 parts by weight or more are uniformly mixed and pulverized to make a flowable agent.

Formulation Example 6 (A) Compound Magnetism 16 50 parts by weight (B) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (C) Silicone 0.2 parts by weight (D)
Add 47.8 parts by weight or more of water to the pulverized stock solution and add (e) 5 parts by weight of sodium polycarboxylate (f) anhydrous sodium sulfate.
Add 42.8 parts by weight, mix uniformly, and dry to obtain a dry flowable agent.

Formulation Example 7 (a) Compound N117 5 parts by weight (b)
Polyoxyethylene octylphenyl ether
1 part by weight (c) 0.5 part by weight of polyoxyethylene phosphoric acid ester (d) 93.5 parts by weight of granular calcium carbonate (a)
- (C) were mixed uniformly in advance, diluted with an appropriate amount of acetone, and then sprayed on (D) to remove acetone to obtain granules.

Formulation Example 8 (a) 2.5 parts by weight of compound magnetic dynamic 1B (b) 2.5 parts by weight of N-methyl-2-pyrrolidone (c) 95.0 parts by weight or more of soybean oil were uniformly mixed and dissolved. micro-spraying agent (ultra
(low volume forn + ulation)
Formulation Example 9 (a) Compound dynamic magnetism 32 5 parts by weight (b) N,
15 parts by weight of N'-dimethylformamide (c) polyoxyethylene alkylaryl (aryl)
) Ether 10 parts by weight (d)xylene
70 parts by weight or more are mixed uniformly to form an emulsion.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) {In the formula, R^1 is a hydrogen atom or an alkyl group, and R^
2 and R^4 are a 6-chloro-3-pyridylmethyl group, a hydrogen atom, or an alkyl group, and R^3 is an alkyl group or a ▲numeric formula, chemical formula, table, etc. ▼ group (X is a hydrogen atom,
is a halogen atom, an alkyl group optionally substituted with a halogen atom, or an alkoxy group optionally substituted with a halogen atom, R^5 is a hydrogen atom or an alkyl group, and n is 0 or 1), However, R^2 is 6-chloro-
When R^2 is a hydrogen atom or an alkyl group, R^4 is a 6-chloro-3-pyridylmethyl group. type compounds or their salts. 2. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) {In the formula, R^1 is a hydrogen atom or an alkyl group, and R^
2 and R^4 are a 6-chloro-3-pyridylmethyl group, a hydrogen atom, or an alkyl group, and R^3 is an alkyl group or a ▲numeric formula, chemical formula, table, etc. ▼ group (X is a hydrogen atom,
is a halogen atom, an alkyl group optionally substituted with a halogen atom, or an alkoxy group optionally substituted with a halogen atom, R^5 is a hydrogen atom or an alkyl group, and n is 0 or 1), However, R^2 is 6-chloro-
When R^2 is a hydrogen atom or an alkyl group, R^4 is a 6-chloro-3-pyridylmethyl group. A pest control agent characterized by containing a series compound or a salt thereof as an active ingredient. 3. General formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 is a hydrogen atom or an alkyl group, and R^
2 and R^4 are a 6-chloro-3-pyridylmethyl group, a hydrogen atom, or an alkyl group, provided that when R^2 is a 6-chloro-3-pyridylmethyl group, R^4 is a hydrogen atom or an alkyl group. and when R^2 is a hydrogen atom or an alkyl group, R^4 is a 6-chloro-3-pyridylmethyl group) and the compound represented by the general formula (III) H_2N-R^3...(III ) {In the formula, R^3 is an alkyl group or a ▲numerical formula, chemical formula, table, etc.▼ group (X is a hydrogen atom,
A halogen atom, an alkyl group optionally substituted with a halogen atom, or an alkoxy group optionally substituted with a halogen atom, R^5 is a hydrogen atom or an alkyl group, and n is 0 or 1)} General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R^1, R^2, R^3 and R^4 are as described above). 4. General formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ {R^2 is 6-chloro-3-pyridylmethyl group, hydrogen atom or an alkyl group, and R^3 is an alkyl group or a ▲ mathematical formula, chemical formula, table, etc. ▼ group (X is a hydrogen atom, a halogen atom, an alkyl group that may be substituted with a halogen atom, or is a good alkoxy group, R^5 is a hydrogen atom or an alkyl group, and n is 0 or 1)] and the compound represented by the general formula H_2N-R^4 (wherein R^4 is 6-chloro-3-pyridylmethyl group,
A hydrogen atom or an alkyl group, provided that when R^2 is a 6-chloro-3-pyridylmethyl group, R^4 is a hydrogen atom or an alkyl group, and when R^2 is a hydrogen atom or an alkyl group, R^ 4 is a 6-chloro-3-pyridylmethyl group) (I-1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I-1) 1) A method for producing a pyrimidine compound represented by the formula (wherein R^2, R^3 and R^4 are as described above).