JPH08259568A - Insecticidal tetrahydropyrimidine derivative - Google Patents

Abstract

PURPOSE: To obtain a tetrahydropyrimidine derivative usable in the field of agriculture, horticulture, livestock industry, forestry, epidemic prevention, houses, etc. CONSTITUTION: This derivative of formula I [(n) is an integer of 2 or 3; R is methyl, ethyl, n-propyl, etc.], e.g. (tetrahydro-3-furanyl)methylamine is obtained in a high yield by reacting a compound of formula II with amines of the formula RNH2 in the presence of formaldehyde (formalin) in a solvent such as methanol, preferably at 0-150 deg.C for 0-15hr. The resultant derivative has precise controlling effects on noxious insects without damaging plants, higher animals, environment, etc., Although, the derivative is stable to light, heat, oxidation, etc. it is stabilized by adding an adequate amount of an antioxidant or an ultraviolet light absorber [e.g. butylated hydroxytoluene (BHT)] thereto.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel tetrahydropyrimidine derivative and an insecticide containing the derivative as an active ingredient.

More specifically, the present invention relates to formula (1) (formula 2)

[0003]

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(In the formula, n represents a number of 2 or 3, and R represents a C1 to C5 alkyl group.) A tetrahydropyrimidine derivative and an insecticide containing the derivative as an active ingredient. Is.

The tetrahydropyrimidine derivative which is a compound of the present invention is useful as an agricultural chemical, especially an insecticide in the agricultural field.

[0006]

2. Description of the Related Art Heretofore, an insecticidal compound having a tetrahydropyrimidine ring has been known (JP-A-62 / 29).
2765, Japanese Patent Application Laid-Open No. 1/160981, etc.). However, among these insecticidal compounds, the active compounds to be seen are limited to pyridine derivatives or thiazole derivatives, and the (tetrahydro-3-furanyl) methyl group which is an essential substituent in the compounds of the present invention. There is no specific description about.

[0007]

The present invention is to provide a novel tetrahydropyrimidine derivative of the above formula (1) having excellent insecticidal activity, which is not the above-mentioned pyridine derivative or thiazole derivative.

[0008]

Means and Actions for Solving the Problems The present inventors have found that the tetrahydropyrimidine derivative represented by the formula (1) has an excellent insecticidal activity even though it does not have a pyridylmethyl group or a thiazolylmethyl group in the molecule. Found to have. That is, the present invention uses the formula (1)

[0009]

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(In the formula, n represents a number of 2 or 3, and R represents a C1 to C5 alkyl group.), A (tetrahydro-3-furanyl) methylamine derivative, and the derivative as an active ingredient. It is an insecticide characterized by containing as.

Typical examples of R in the above formula include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec. -Butyl group, tert. -Butyl group, n-pentyl group, cyclopentyl group, etc. are mentioned, and a methyl group is preferable.

The compound of formula (1) of the present invention can be produced by the following reaction formula (1) (formula 4).

[0013]

[Chemical 4]

(In the formula, n and R have the above meanings.) That is, the compound represented by the formula (2) and the amine represented by the formula (3) are added in the presence of formaldehyde (formalin). , And can be easily produced in high yield.

The reaction can be easily produced by reacting in various solvents.

Examples of the solvent include water, alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane, heptane and petroleum benzine, and dimethyl. Formamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, aprotic polar solvent such as 1-methyl-2-pyrrolidinone, ethyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, Ethers such as dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone and diisopropyl ketone can be used.

The reaction temperature and the reaction time can be varied over a wide range, but in general, the reaction temperature is -20 to 20.
200 ° C., preferably 0-150 ° C., reaction time 0.0
It is 1 to 50 hours, preferably 0.1 to 15 hours.

In the reaction formula (1), the compound of the formula (2) can be produced by the following reaction formula (2) (formula 5).

[0019]

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(In the formula, n represents the above meaning, R ₁ represents a halogen atom, a C1 to C5 alkylthio group or a benzylthio group.) That is, the compound represented by the formula (4) and the formula (4) It can be easily produced in a high yield by reacting the compound represented by 5).

The reaction can be easily carried out by reacting in various solvents in the presence of a catalyst, if necessary.

As the catalyst, 4- (dimethylamino) pyridine, DBU, triethylamine, diazabicycloundecene and other organic bases, ion exchange resins, silica gels,
Zeolite or the like can be used.

Examples of the solvent include water, alcohols such as methanol, ethanol, propanol and butanol, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as hexane, heptane and petroleum benzine, and dimethyl. Formamide, dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolidinone, aprotic polar solvent such as 1-methyl-2-pyrrolidinone, ethyl ether, diisopropyl ether, 1,2-dimethoxyethane, tetrahydrofuran, Ethers such as dioxane, nitriles such as acetonitrile and propionitrile, and ketones such as acetone and diisopropyl ketone can be used.

The reaction temperature and reaction time can be varied over a wide range, but in general, the reaction temperature is -20 to 20.
200 ° C., preferably 0-150 ° C., reaction time 0.0
It is 1 to 50 hours, preferably 0.1 to 15 hours.

In the reaction formula (2), the compound represented by the formula (4) can be produced by the following reaction formula (3) (formula 6).

[0026]

[Chemical 6]

(In the formula, X represents a halogen atom, a toluenesulfonyloxy group, a methanesulfonyloxy group, and a trifluoromethanesulfonyloxy group, and n represents the above-mentioned meaning.) Sunflower (tetrahydro-3-furanyl) methanol Halides or tosyl chloride, methanesulfonyl chloride, trifluoromethanesulfonic acid with halogenating agents such as thionyl chloride, phosphorus oxychloride, phosphorus tribromide, triphenylphosphine / carbon tetrabromide, triphenylphosphine / carbon tetrachloride, etc. It can be produced by converting the compound to a sulfonated compound with a sulfonated agent such as an anhydride to give a compound represented by the formula (6), and then reacting it with a diamine represented by the formula (7).

The compound represented by the formula (1) has an asymmetric carbon atom, and both an optically active substance and a racemic substance resulting therefrom are included in the present invention.

The compound represented by the formula (5) is a known compound or a compound which can be produced according to a known method.

Conventionally, an insecticidal compound having a tetrahydropyrimidine ring has been known. However, among these insecticidal compounds, the active compounds to be found were limited to pyridine derivatives or thiazole derivatives. The compound represented by the formula (1) of the present invention exhibits an extremely excellent insecticidal action even though it does not have these pyridylmethyl group or thiazolylmethyl group in the molecule. In the compound represented by the formula (1) of the present invention, a (tetrahydro-3-furanyl) methyl group is a isomer of (tetrahydro-2-furanyl) methyl group and an unsaturated tetrahydrofurfuryl group, or When it was replaced with a known pyridylmethyl group or the like, the insecticidal activity was remarkably reduced as compared with the compound represented by the formula (1).

That is, the compound represented by the formula (1) of the present invention is characterized by having a (tetrahydro-3-furanyl) methyl group as a heterocycle in the molecule.

The derivative represented by the formula (1) of the present invention has a strong insecticidal action, and can be used as an insecticide in various scenes such as agriculture, horticulture, livestock, forestry, epidemics and houses. Further, the derivative represented by the formula (1) of the present invention exerts a proper controlling effect against harmful insects without causing any damage to plants, higher animals, environment and the like.

Examples of such pests include armyworm, Tamanayaga, white-spotted armyworm, Spodoptera litura, Kaburagaga, Yotoga, Tamanaginuwaba, Nikamaiga, Kobunomeiga, Hyakudarameiga, Insect beetle, Cotton bollworm, Potato moth, Monads
Lepidoptera insect pests such as Nosima Madaraiga, Chanocha sukuensis, Kinmon Hosoga, Mikanhamogiga, Nashihime Shinkoi, Mameshino Shinga, Peach mosquito, Grape scabbard, Koga, Tobacco whitefly, Onitsutsuko whitefly, Mikantoge whitefly, Whitefly
Yukiyanagi aphid, apple aphid, green peach aphid, radish aphid, harbor aphid, bean aphid, orange aphid, wheat aphid, potato aphid, green aphid, green tea leafhopper, leafhopper leafhopper, blackhopper planthopper, blackhopper planthopper, blackhopper planthopper, leafhopper planthopper Taiwantsuno Tuna leafhopper, Yanoe scale scale, stag beetle scale, citrus scale scale,
Hemiptera pests such as the moss bug, the southern green stink bug, the leaf beetle, the beetle bug, the rice leaf weevil, the rice droopyworm, the dwarf worm, Diabrotica spp. Coleoptera pests such as, Pleurotus ostreatus, Pleurotus cornucopiae, Astragalus vulgaris, etc .; Culex pipiens, Culex pipiens, Aedes albopictus, Pleurotus spp. Thrips insects, such as thrips, oysters, thrips, thrips, rice thrips, and thrips thrips Orthoptera such as black cockroaches, American cockroaches, American cockroaches, German cockroaches, Cobainigo, and locust grasshoppers; Hymenoptera, such as turnips; , Geji and the like.

When the compound represented by the formula (1) of the present invention is actually applied, it can be used in a plain form without adding other components, but a carrier is blended for easy use as a controlling agent. Is generally applied.

In formulating the compound of the present invention, no special conditions are required, and an emulsion, wettable powder, powder, granule,
It can be adjusted to any dosage form such as fine granules, flowables, microcapsules, oils, aerosols, smoke agents, and poison baits, and these can be used for various purposes according to their respective purposes.

The term "carrier" as used herein refers to the synthesis or synthesis of a liquid, solid or gas which is formulated to help the active ingredient reach the site to be treated and facilitate the storage, transportation and handling of the active ingredient compound. It means a natural inorganic or organic substance.

Suitable solid carriers include, for example, montmorillonite, kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel,
Inorganic substances such as ammonium sulfate, soybean flour, sawdust, wheat flour, pectin,
Methylcellulose, sodium alginate, petrolatum,
Examples include organic substances such as lanolin, liquid paraffin, lard, and vegetable oil.

Suitable liquid carriers include, for example, toluene,
Aromatic hydrocarbons such as xylene, cumene and solvent naphtha, paraffin hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, ketones such as acetone, methyl ethyl ketone and cyclohexanone, Ethers such as dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc., esters such as ethyl acetate, acetic acid butyl ester, fatty acid glycerin ester, etc. acetonitrile, nitriles such as propionitrile Alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol, dimethylformamide, di- Sulfoxide, water and the like.

Further, in order to enhance the potency of the compound represented by the formula (1) of the present invention, the following may be used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene and the like. It is also possible to use such auxiliaries.

As an auxiliary agent used for the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc., water-soluble bases such as lignin sulfonates, alkylbenzene sulfonates,
Alkyl sulfates, polyoxyethylene alkylaryl ethers, nonionic surfactants such as polyhydric alcohol esters, lubricants such as calcium stearate and wax, stabilizers such as isopropylhydrodiene phosphate, other methyl cellulose, carboxymethyl cellulose, Examples include casein and gum arabic.
However, these components are not limited to those described above.

Further, these compounds represented by the formula (1) of the present invention can express more excellent insecticidal activity by using two or more kinds of them in combination, and other physiologically active substances such as allethrin, Tetramethrin, resmethrin, phenothrin, flamethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropatrine, tralomethrin, cycloprothrin, flucitrinate, fluvalinate, acrinathrin, tefluthrin, bifenthrin, enpentrin, betacyfluta. Synthetic pyrethroid insecticides such as cypermethrin and various isomers or pyrethrum extract thereof; DDVP, cyanophos, fenthion, fenitrothion, tetrachlorvinphos,
Dimethylvinphos, Propaphos, Methylparathion, Temephos, Phoxime, Acephate, Isofenphos, Salithione, DEP, EPN, Ethione, Mecarbam, Pyridafenthione, Diazinon, Pirimiphos-methyl,
Etrimphos, isoxathion, quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet, methidathion, oxydebrophos, bamidthione,
Organophosphorus insecticides such as malathion, fentoate, dimethoate, formothion, thiomethone, ethyl thiomethone, folates, terbufos, profenophos, prothiophos, sulprophos, pyraclofos, monocrotophos, naredo, fostiazate, NAC, MTMC, MI
PC, BPMC, XMC, PHC, MPMC, ethiophene carb, bendiocarb, pirimicarb, carbosulfan, benfuracarb, mesomil, oxamyl,
Carbamate insecticides such as aldicarb, arylpropyl ether insecticides such as etofenprox and halfenprox, and silyl ether compounds such as silafluofene. Nicotine sulfate, polynactin complex,
Insecticidal natural products such as avermectin, milbemectin, BT agents, cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid. , Insecticides such as pymetrozine, fipronil, buprofezin, phenoxycarb, pyriproxyfen, methoprene, hydroprene, quinoprene, endosulfan, diafenthiuron, triazuron, tebufenozide, benzoepine, dicofol, chlorbendylate, phenisobromolate, tetradiphone , CPCBS, BPPS, quinomethionate, amitraz, benzomate, hexithiaxox, phen oxide Insecticides such as tatin, cyhexatin, dienochlor, clofentezine, pyridaben, fenpyroximate, phenazaquin, tebufenpyrad, pyrimidinamine, other insecticides, acaricides or fungicides, nematicides, herbicides, plant growth regulators, fertilizers , Soil improving materials, BT agents, microbial production toxins, natural or synthetic insect hormone disruptors, attractants, repellents, and other pesticides such as entomopathogenic microorganisms and small animals. It is also possible to make a multi-purpose composition and to expect a synergistic effect.

The compound represented by the formula (1) of the present invention is stable to light, heat, oxidation and the like, but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2,6-di-
t-butyl-4-methylphenol), a phenol derivative such as BHA (butylhydroxyanisole), a bisphenol derivative, arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, and a condensate of phenetidine and acetone, or By adding an appropriate amount of benzophenone compounds as a stabilizer, a composition having a more effective effect can be obtained.

The insecticide of the compound represented by the formula (1) of the present invention contains 0.0000001 to 95% by weight, preferably 0.0001 to 50% by weight of the compound.

To apply the insecticide of the present invention, generally 0.001 to 5000 ppm of active ingredient, preferably 0.01
It is desirable to use it at a concentration of up to 1000 ppm. The amount applied per 10a is generally 1 to 3 for the active ingredient.
It is 00 g.

[0045]

EXAMPLES The contents of the present invention will be specifically described with reference to the following reference examples and examples, but the present invention is not limited thereto.

Reference Example 1 (Tetrahydro-3-furanyl) methyl tosylate (Tetrahydro-3-furanyl) methanol 50 g, tosyl chloride 95 g, triethylamine 52 g, TH
A mixture of 450 ml of F was heated to reflux for 8 hours. The insoluble material was filtered off, the reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent; ethyl acetate: hexane = 1: 7) to give 114.5 g of 3- (tetrahydro-3-furanyl). Methyl tosylate was obtained.

Reference Example 2 (Tetrahydro-3-furanyl) methyl bromide 10 g of phosphorus tribromide, 0.8 g of pyridine, 100 of ether
To the mixture of ml, 10 g of (tetrahydro-3-furanyl) methanol was added dropwise over 30 minutes, and then the mixture was stirred for 5.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate: hexane =
It was purified by 1: 1) to obtain 8.6 g of (tetrahydro-3-furanyl) methyl bromide. ¹ HNMR (CDCl ₃ , ppm): 1.62-1.76 (1H, m), 2.05-2.16 (1H, m),
2.70 (1H, septet, J = 7.3Hz) 3.40 (2H, dd, J = 1.5Hz, J = 7.3H
z), 3.45-3.53 (1H, m), 3.60 (1H, dd, J = 5.1Hz, J = 8.8Hz), 3.8
0 (1H, t, J = 7.3Hz), 3.89-3.95 (1H, m)

Reference Example 3 1- (Tetrahydro-3-
3. Furanyl) methyl-2- (nitromethylene) imidazolidine (tetrahydro-3-furanyl) methyl tosylate
A mixture of 0 g, ethylenediamine 10 ml, anhydrous potassium carbonate 4.52 g and sodium iodide 0.50 g was refluxed in acetonitrile for 2 hours. After completion of the reaction, insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure to obtain 2.12 g of a crude oily substance. The crude oil thus obtained and 1,1-bis (methylthio) -2-nitroethylene 2.43 g, dimethylaminopyridine (DMAP) 0.1 g, ethanol 20
The ml mixture was boiled under reflux for 3 hours 30 minutes. After completion of the reaction, insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained oily substance was purified by column chromatography (silica gel, ethyl acetate: acetone = 1: 1) to give 0.6
3 g of 1- (tetrahydro-3-furanyl) methyl-2
-(Nitromethylene) imidazolidine was obtained. ¹ HNMR (CDCl ₃ , ppm): 1.51-1.72 (1H, m), 2.00-2.20 (1H, m),
2.50-2.68 (1H, m), 3.13 (2H, d, J = 7.3), 3.48-4.00 (8H, m),
6.57 (1H, s), 8.69 (1H, br.) IR (KBr, cm ^-1 ): 3338,2860,1577,1431,1390,1256,1068,76
Four

Reference Example 4 1- (Tetrahydro-3-
Furanyl) methyl-2- (nitromethylene) hexahydr
Ropyrimidine (tetrahydro-3-furanyl) methyl tosylate 2.
0 g, 1,3-propanediamine 6 ml, anhydrous potassium carbonate
A mixture of 3.00 g of sodium and 0.20 g of sodium iodide
Was refluxed in acetonitrile for 4 hours. After the reaction is complete,
The melt was filtered off and the filtrate was concentrated under reduced pressure to give a crude oil 1.18.
g was obtained. The crude oil thus obtained and 1,1-bis
(Methylthio) -2-nitroethylene 1.40 g, dime
Cylaminopyridine (DMAP) 0.1g, ethanol
10 ml of the mixture was boiled under reflux for 3 hours. After the reaction,
The insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. Obtained
Column chromatography (silica gel, vinegar)
Ethyl acetate: acetone = 1: 1) and 0.35 g
1- (tetrahydro-3-furanyl) methyl-2- (d
Tromethylene) hexahydropyrimidine was obtained. ¹ HNMR (CDCl₃, ppm): 1.56-1.72 (1H, m), 1.96-2.12 (3H, m),
2.67-2.82 (1H, m), 3.32-3.57 (5H, m), 3.62-3.95 (5H, m), 9.
79 (1H, br.) IR (KBr, cm^-1): 3256,1593,1321,1243,1156

EXAMPLE 1 1- (Tetrahydro-3-furanyl) methyl-2- (nitromethylene) imidazolidine 0.7 g, formalin 1.4 g, 40% methylamine methanol solution 0.7
g and 10 ml of methanol were stirred at 60 ° C. for 2 hours. The reaction mixture was concentrated and the resulting oil was purified by column chromatography (silica gel, acetone) to give 0.55 g of 6,7-dihydro-6-methyl-8-nitro- (5H).
-3-{(Tetrahydro-3-furanyl) methyl} imidazolidino- [2,3-f] -pyrimidine (Compound N
o. 1) was obtained. ¹ HNMR (acetone-d ₆ , ppm): 1.62-1.74 (1H, m)), 1.95-2.07 (1
H, m), 2.41 (3H, s), 2.67 (1H, septet, J-7.3), 3.44 (1H, dd, J
= 6.6, J = 8.8), 3.56-3.88 (9H, m), 3.64 (2H, s), 4.00 (2H, s) IR (KBr, cm ^-1 ): 1554,1364,1282,1162,1107 mp: 114-116 ° C

Example 2 0.50 g of 1- (tetrahydro-3-furanyl) methyl-2- (nitromethylene) hexahydropyrimidine, 0.41 g of formalin, 0.28 g of a 40% methylamine methanol solution and 10 ml of ethanol at 40 ° C. And stirred for 3 hours. The reaction solution was concentrated, and the precipitated crystals were collected by filtration to give 0.2
5 g of 6- (tetrahydro-3-furanyl) methyl-3
-Methyl-5-nitro-1,2,3,6-tetrahydropyrimidino [3,4-b] hexahydropyrimidine (Compound No. 2) was obtained. ¹ HNMR (CDCl ₃ , ppm): 1.48-1.66 (1H, m), 1.95-2.22 (3H, m),
2.43 (3H, s), 2.54-2.76 (1H, m), 3.32-3.62 (7H, m), 3.68-3.
98 (7H, m) IR (KBr, cm ^-1 ): 2924,1592,1521,1399,1102,737 mp: 160.0-160.4 ℃

Next, the composition of the present invention will be specifically described with reference to formulation examples. In the following formulation examples, parts represent parts by weight.

Formulation Example 1 20 parts of the compound of the present invention, 10 parts of Solpol 355S (manufactured by Toho Kagaku Co., surfactant), and 70 parts of xylene were uniformly mixed with stirring to obtain an emulsion.

Formulation Example 2 10 parts of the compound of the present invention, 2 parts of sodium alkylnaphthalene sulfonate, 1 part of sodium lignin sulfonate, 5 parts of white carbon, 82 parts of diatomaceous earth, 100 parts of wettable powder by uniformly stirring and mixing the above. Got

Formulation Example 3 0.3 part of the compound of the present invention and 0.3 part of white carbon are uniformly mixed, and 99.2 parts of clay and Dolores A (manufactured by Sankyo)
0.2 part was added and uniformly pulverized and mixed to obtain 100 parts of powder.

Formulation Example 4 2 parts of the compound of the present invention, 2 parts of white carbon, 2 parts of sodium lignin sulfonate, 94 parts of bentonite are uniformly pulverized and mixed, and then water is added and kneaded, granulated and dried to obtain granules. 100 parts were obtained.

Formulation Example 5 20 parts of the compound of the present invention and 20 parts of polyvinyl alcohol
% Of 5% aqueous solution was thoroughly mixed with stirring, then 75 parts of 0.8% aqueous solution of xanthan gum was added and mixed again with stirring to obtain 100 parts of a flowable agent.

Formulation Example 6 10 parts of the compound of the present invention, carboxymethyl cellulose 3
Parts, 2 parts of sodium ligninsulfonate, 1 part of dioctylsulfosuccinate sodium salt, and 84 parts of water were uniformly wet-ground to obtain 100 parts of a flowable agent.

Next, in order to clarify that the compound represented by the formula (1) of the present invention has an excellent insecticidal activity, it will be specifically described by the following test examples.

Test Example 1 Effect on Spodoptera frugiperda The compound of the present invention is used as an acetone solution having a predetermined concentration and sprayed in an amount of 3 ml on rice seedlings (about 3 leaf stage) bundled in several pieces. After air-drying, the treated seedlings are covered with a wire netting cylinder, and then the female adult genus Astragalus L.
Zero of them were released and placed in a constant temperature room at 25 ° C, and 48 hours later, the mortality was examined.

Test Example 2 Effect on Resistant Green Leafhopper The compound of the present invention is made into an acetone solution having a predetermined concentration and sprayed in an amount of 3 ml on rice seedlings (about 3 leaf stages) bundled in several pieces. After air-drying, the treated seedlings are covered with a wire netting cylinder, and 10 resistant female leafhopper leafhoppers are laid inside each and placed in a temperature-controlled room at 25 ° C for 48 hours.
Mortality was investigated after hours. The results of Test Examples 1 and 2 are first
The results are shown in the table (Table 1).

[0062]

[Table 1]

Comparative compound: 6,7-dihydro-6-methyl-8-nitro- (5H) -3-{(tetrahydro-2
-Furanyl) methyl} imidazolidino- [2,3-f]
-Pyrimidine

[0064]

The novel tetrahydropyrimidine derivative represented by the formula (1) of the present invention is an excellent compound having a high insecticidal activity and a broad insecticidal spectrum.

The pesticide containing the novel tetrahydropyrimidine derivative represented by the formula (1) of the present invention has excellent properties as an insecticide and is useful.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazutomi Onuma 1144, Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd. (72) Inventor Naoko Yasui, 1144, Togo, Mobara-shi, Chiba Mitsui Toatsu Chem.

Claims (2)

[Claims] 1. Formula (1) (Formula 1) (In the formula, n represents a number of 2 or 3, and R represents a C1 to C5 alkyl group.) A tetrahydropyrimidine derivative. 2. An insecticide comprising the compound represented by formula (1) according to claim 1 as an active ingredient.