JPH0543536A - New amidine derivative, and insecticide/miticide containing the same - Google Patents

Abstract

(57) [Summary] [Configuration] Formula I [Chemical Formula 1] (R ₁ is hydrogen, halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, methyldioxy. X is methine, nitrogen. M is 1 to
3. R ₂ is alkyl, alkenyl, haloalkyl, C3
~ 4 cycloaliphatic groups. R ₃ is hydrogen, cyano, ethynyl, methyl. R ₄ is hydrogen or fluorine. R ₅ is hydrogen, halogen, methyl or methoxy group. ) Amidine derivatives represented by the formula (1), and insecticides and acaricides containing the same. [Effect] The compound has low toxicity to humans and animals, and exhibits high activity against various pests and mites. Unlike conventional pyrethroids, it is particularly effective against indoor dust mites.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a novel amidine derivative,
And an insecticidal and acaricidal agent containing the same.

[0002]

BACKGROUND OF THE INVENTION Natural pyrethrins and chrysanthemic acid-based pyrethroids are excellent insecticides that combine fast-acting activity with insects and low toxicity to humans and animals, but they are susceptible to oxidative decomposition due to light, and their use outdoors is restricted. I received it. on the other hand,
The use of organochlorine insecticides such as BHC and DDT is prohibited due to problems such as environmental pollution and chronic toxicity. Furthermore, organic phosphate ester-based and carbamate-based insecticides, which should replace them, also have resistance pest problems in various fields. It is showing signs of becoming more serious, and against these backgrounds, the creation of new and superior insecticides and acaricides has been earnestly desired. And in recent years
Various synthetic pyrethroids have been developed, for example the general formula I
I

[Chemical 3] (In the formula, R ₆ and n have the same meanings as R _{1 and} m described above, and R ₇ represents a hydrogen atom or a cyano group.) The α-anilino isovaleric acid esters represented by Overcoming the instability in the field, which was a weak point of pyrethroids, it has been put to practical use as an agricultural insecticide (JP-A-52).
-82724). On the other hand, in parallel with the modification of the alcohol part and the acid part of the pyrethroid, many attempts have been made to modify the ester part.

[Chemical 4] (In the formula, R ₈ has the same meaning as R ₁ described above.) An oxime ether represented by JP-A-55-115864 is disclosed.
And JP-A-56-45455. However, the compound represented by the general formula II or the general formula III is
It has a problem that it is highly toxic to natural enemy pests and fish, and that it is weak against mites, especially indoor dust mites such as mites and deer mites.

[0003]

[Problems to be Solved by the Invention] Recently, due to changes in the living environment, a great number of mites and deer mite species have emerged in the home.
Not only does it cause discomfort, but it causes problems such as allergic asthma and skin rash. It is known that organophosphorus agents such as Sumithion and diazinon are effective for mites that occur indoors, but there are many obstacles to indoor use due to their toxicity to humans and animals. The present invention has been made with the object of solving the problems of conventional insecticides and developing pyrethroids which are excellent in insecticidal activity and acaricidal activity (particularly activity against indoor dust mites) and which are highly safe. ..

[0004]

[Means for Solving the Problems] In order to achieve the above object, the inventors of the present invention have conducted diligent research, and as a result, by structurally combining the compounds of general formula II and general formula III, the hydrophilicity is increased, It was found that the acaricidal activity can be imparted. That is, the present invention relates to a novel amidine derivative represented by the general formula I, and an insecticidal and acaricidal agent containing the same.

The compounds of general formula I used in the present invention are
According to the general method for producing oxime ethers, for example, the general formula

[Chemical 5] (In the formula, R ₁ is a hydrogen atom, a halogen atom, or a carbon atom of 1
To 4 lower alkyl groups, lower alkoxy groups, lower alkylthio groups, lower haloalkyl groups, lower haloalkoxy groups, lower haloalkylthio groups or methylenedioxy groups. X represents a methine group or a nitrogen atom, and m represents an integer of 1 to 3. R ₂ represents a lower alkyl group having 2 to 4 carbon atoms, a lower alkenyl group, a lower haloalkyl group or an alicyclic group having 3 to 4 carbon atoms. ) N-substituted carboxamide represented by the general formula V

[Chemical 6] (In the formula, R ₃ represents a hydrogen atom, a cyano group, an ethynyl group or a methyl group, R ₄ represents a hydrogen atom or a fluorine atom, and R ₅ represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group. ) And a substituted benzyloxyamine represented by the formula (1) in the presence of phosphorus pentachloride. The reaction is carried out in a suitable solvent, optionally with heating.

[0006] In the general formula I, there are syn-type and anti-type resulting from the substitution model of oxime, and each of these and a mixture are included in the present invention, and both isomers can be separated by chromatography or the like. Is. Similarly, tautomeric structural isomers also include each and any mixture.

Next, representative examples of the compound represented by the general formula I will be shown, and synthetic routes thereof are shown below.

[Chemical 7]

[Chemical 8]

Synthesis Example 1 Synthesis of N- (4-ethoxyphenyl) -N '-(3-phenoxybenzyloxy) isobutyroamidine [Compound (1)]

[Chemical 9] A) Synthesis of N- (4-ethoxyphenyl) isobutyroamide 8.95 g (84 mM) of isobutyryl chloride was dissolved in 60 ml of anhydrous ether. 4-ethoxyaniline 1
1.5 g (84 mM), triethylamine 8.48 g
A mixed solution of (84 mM) dissolved in 60 ml of anhydrous ether was added dropwise while stirring with ice cooling, and after the addition, the mixture was stirred at room temperature for 45 minutes. The yellow solid obtained by filtration was washed with water and dried under reduced pressure. This was recrystallized from 100 ml of 75% ethanol to give needle-like colorless crystals of N- (4-ethoxyphenyl).
11.82 g of isobutyroamide was obtained (yield 68.0).
%). Melting point 139 [deg.] C.

B) Synthesis of 3-phenoxybenzyloxyamine 15 g (75 mM) of 3-phenoxybenzyl alcohol
And pyridine (6.07 g, 76.8 mM) were added dropwise while stirring at 10 ° C., and thionyl chloride (9 g, 75.6 mM) was added dropwise. After the addition, the mixture was stirred at room temperature for 3.5 hours. Ice-cooled water and 20 ml of ether were added to the reaction solution, and the aqueous layer was 20 m of ether.
It was extracted with 1 and the ethers were combined and washed with saturated aqueous sodium hydrogen carbonate solution and water. After drying over anhydrous sodium sulfate, ether was distilled off under reduced pressure, and the obtained oily substance was subjected to silica gel column chromatography (benzene: ethyl acetate = 2).
(0: 1) to obtain 15.73 g of 3-phenoxybenzyl chloride as a colorless oily substance (yield 96.0).
%). DMS containing 3 g (18 mM) of N-hydroxyphthalimide
It was dissolved in 20 ml of O. Anhydrous potassium carbonate 1.9
3 g (14 mM) was gradually added, and 8 g (36.6 mM) of 3-phenoxybenzyl chloride was stirred at 30
The mixture was added dropwise at a temperature of not higher than 0 ° C, and after the addition, the mixture was stirred at room temperature for 24 hours. This was added to 60 ml of ice-cold water, and the mixture was allowed to stand at 0 to 5 ° C for half an hour, and the precipitated colorless crystals were filtered. This crystal is ethanol 5
The crystals were recrystallized from 0 ml to give 4.94 g of colorless needle crystals of N- (3-phenoxybenzyloxy) phthalimide (yield 79.6%, melting point 97-98 ° C). N- (3-phenoxybenzyloxy) phthalimide 8
g (23.2 mM) was dissolved in 30 ml DMF. 2.32 g (46.4 m) of hydrazine hydrate at 70 ° C
M) was added with stirring and this was stirred at this temperature for 1.5 hours. After the reaction solution was allowed to cool, 70 ml of water was added and further acidified with hydrochloric acid. After sufficiently cooled, the mixture was filtered, and the filtrate was made alkaline with 8% sodium hydroxide. This was extracted with ether and dried over anhydrous sodium sulfate. The oil obtained by distilling off the ether under reduced pressure was purified by silica gel column chromatography (chloroform) to obtain 3.68 g of 3-phenoxybenzyloxyamine as a colorless oil (yield 74.2%).

C) N- (4-ethoxyphenyl) -N '
Synthesis of-(3-phenoxybenzyloxy) isobutyroamidine [Compound (1)] 0.67 g (3.2 mM) of phosphorus pentachloride was dissolved in 10 ml of anhydrous chloroform, and N- (4-ethoxyphenyl) isobutyroamide was dissolved therein. 0.58 g (2.8 mM) was added. This solution was stirred at 70 ° C. for 1 hour in a nitrogen stream. After allowing the reaction solution to cool, 0.6 g (2.8 mM) of 3-phenoxybenzyloxyamine was added. This solution was stirred overnight at 70 ° C. in a nitrogen stream. After allowing the reaction solution to cool, a 6.7% sodium ethoxide ethanol solution (2.8 × 4 mM) was added thereto. This was washed with water and dried over anhydrous sodium sulfate. The oily substance obtained by distilling off chloroform under reduced pressure was purified by silica gel column chromatography (chloroform: n-hexane = 3: 1) to obtain N- (4-ethoxyphenyl) -N ′ as a colorless oily substance.
0.45 g of-(3-phenoxybenzyloxy) isobutyroamidine [compound (1)] was obtained (yield 39.8).
%).

Synthesis Example 2 Synthesis of N- [2- (5-trifluoromethyl-3-chloropyridyl)]-N '-(3-phenoxybenzyloxy) isobutyroamidine [Compound (2)]

[Chemical 10] A) Synthesis of N- [2- (5-trifluoromethyl-3-chloropyridyl)] isobutyroamide 1.63 g (15.3 mM) of isobutyryl chloride was dissolved in 15 ml of anhydrous ether. 3.0 g of 2-amino-3-chloro-5-trifluoromethylpyridine (1
5.3 mM and 1.55 g (15.3 g) of triethylamine.
(mM) dissolved in 15 ml of anhydrous ether was added dropwise while stirring with ice cooling to solidify. After filtration for about 10 minutes, the obtained yellow solid was mixed with water, 2% sodium carbonate 50m.
Wash with l. After drying under reduced pressure, 75% ethanol 1
Recrystallization was carried out with 00 ml to obtain N- [2-
(5-Trifluoromethyl-3-chloropyridyl)] isobutyroamide 1.11 g was obtained (yield 27.2%).
Melting point 82-84 [deg.] C.

C) Synthesis of N- [2- (5-trifluoromethyl-3-chloropyridyl)]-N '-(3-phenoxybenzyloxy) isobutyroamidine [Compound (2)] Phosphorus pentachloride 0 1.9 g (4.3 mM) was dissolved in 10 ml of anhydrous chloroform, and 1.0 g (3.7 mM) of N- [2- (5-trifluoromethyl-3-chloropyridyl)] isobutyroamide was added thereto. This solution was stirred at 70 ° C. for 6.5 hours in a nitrogen stream. After cooling, 0.8 g of 3-phenoxybenzyloxyamine (3.
7 mM) was added, and the reaction solution was stirred overnight at 70 ° C. in a nitrogen stream. After allowing the reaction solution to cool, a 6.7% sodium ethoxide ethanol solution (3.7 × 3.5 mM) was added thereto, washed with water, and then dried over anhydrous sodium sulfate. The oily substance obtained by distilling off chloroform under reduced pressure was purified by silica gel column chromatography (chloroform: n-hexane = 3: 1) to obtain N- [2
-(5-trifluoromethyl-3-chloropyridyl)]
0.3 g of -N '-(3-phenoxybenzyloxy) isobutyroamidine [compound (2)] was obtained (yield 17.
3%).

Synthesis Example 3 Synthesis of N- (4-ethoxyphenyl) -N '-(3-phenoxy-α-methylbenzyloxy) isobutyroamidine [Compound (3)]

[Chemical 11] 1.06 g (5.1 mM) of phosphorus pentachloride was dissolved in 10 ml of anhydrous chloroform, and 0.91 g (4.4 mM) of N- (4-ethoxyphenyl) isobutyroamide was added thereto. This solution was stirred at 70 ° C. for 2 hours in a nitrogen stream,
After allowing the reaction solution to cool, 1.0 g (4.4 mM) of 3-phenoxy-α-methylbenzyloxyamine was added. The solution was further stirred in a nitrogen stream at 70 ° C. overnight, the reaction solution was allowed to cool, and chloroform was distilled off under reduced pressure. 6.7% to this
Ethanol solution of sodium ethoxide (4.4 × 4m
M) was added, water and ether were added, and the aqueous layer was extracted with ether. The ether layers were combined, washed with water, and dried over anhydrous sodium sulfate. The oil obtained by distilling off the ether under reduced pressure was purified by silica gel column chromatography (chloroform), and a colorless oil of N- (4-ethoxyphenyl) -N '-(3-phenoxy-α-methylbenzyloxy) was obtained. Isobutyroamidine [Compound (3)]
0.4 g was obtained (yield 21.7%).

Synthesis Example 4 Synthesis of N- (4-chlorophenyl) -N '-[3- (3-methoxyphenoxy) benzyloxy] isobutyroamidine [Compound (4)]

[Chemical formula 12] According to Synthesis Example 3, N- (4-chlorophenyl) isobutyroamide 0.95 g (4.8 mM) and 3- (3-methoxyphenoxy) benzyloxyamine 1.18 g (4.
8 mM) in the presence of phosphorus pentachloride to react with N- (4-
0.41 g of chlorophenyl) -N '-[3- (3-methoxyphenoxy) benzyloxy] isobutyroamidine [compound (4)] was obtained (yield 20.1%).

The physical constants of the compounds of the present invention obtained in Synthesis Examples 1 to 4 are as shown in Table 1.

[Table 1]

The compounds synthesized in the same manner as in Synthesis Examples 1 to 4 are shown below, but the present invention is not limited to them. Compound (5): N- (2-fluoro-4-tert-butylphenyl) -N '-(3-phenoxy-α-cyanobenzyloxy) propioamidine

[Chemical 13] Compound (6): N- (2,6-dimethyl-4-chloromethylphenyl) -N '-[3- (4-methylphenoxy) -4-fluorobenzyloxy] cyclopropylcarbamidine

[Chemical 14] Compound (7): N- (4-isopropylthiophenyl)
-N '-[3- (2-fluorophenoxy) -α-methylbenzyloxy] isopropenylcarbamidine

[Chemical 15] Compound (8): N- (3,4-methylenedioxyphenyl) -N '-(3-phenoxy-4-fluorobenzyloxy) -2,2-ditrifluoromethylacetamidine

[Chemical 16] Compound (9): N- [2- (5-dylfluoromethoxy-3-methoxypyridyl)]-N '-[3- (4-bromophenoxy) -α-ethynylbenzyloxy] cyclobutylcarbamidine

[Chemical 17] Compound (10): N- [2- (6-ethyl-4-bromoethylthiopyridyl)]-N '-[3- (3-methoxyphenoxy) -4-fluorobenzyloxy] -2-methylisobutyro Amidine

[Chemical 18] Compound (11): N- [2- (5-pentafluoroethoxy-3-bromopyridyl)]-N '-[3- (3-methylphenoxy) -α-methylbenzyloxy] propioamidine

[Chemical 19] Compound (12): N- [2- (5-propoxy-3-methylthiopyridyl)]-N '-(3-phenoxybenzyloxy) vinylcarbamidine

[Chemical 20] Compound (13): N- [2- (4,5-methylenedioxy-3-fluoropyridyl)]-N '-[3- (4-fluorophenoxy) -4-fluoro-α-cyanobenzyloxy]- 2-chloropropioamidine

[Chemical 21] Compound (14): N- (3-chloromethylthio-4-trifluoromethoxyphenyl) -N '-[3- (4-chlorophenoxy) -α-cyanobenzyloxy] propioamidine

[Chemical formula 22] Compound (15): N- (4-isobutylphenyl)-
N '-[3- (3-methylphenoxy) -α-ethynylbenzyloxy] -2-fluoroisobutyroamidine

[Chemical formula 23] Compound (16): N- (2-chloro-4-trifluoromethylphenyl) -N '-(3-phenoxy-α-methylbenzyloxy] isobutyroamidine

[Chemical formula 24] Compound (17): N- (4-ethoxyphenyl) -N '
-[3- (3-Methoxyphenoxy) benzyloxy]
Isobutyroamidine

[Chemical 25] Compound (18): N- (4-ethoxyphenyl) -N '
-(3-phenoxy-4-fluorobenzyloxy) isobutyroamidine

[Chemical formula 26]

The compound used in the present invention is a novel compound, which is a solid or liquid at room temperature and is generally easily soluble in organic solvents. Therefore, as a spray insecticide, acaricide, emulsion,
It can be used as an oil, a powder, a wettable powder, an aerosol, etc., and can also be used as a fumigant insecticide such as mosquito coil and an acaricide by mixing with wood powder or other suitable base material. Also, when used as a so-called electric mosquito coil which dissolves this active ingredient in a suitable organic solvent and soaks it in a mount, or dissolves it in a suitable solvent and evaporates by heating with a suitable heating element Show the effect. The compound of the present invention is more stable to light than conventional pyrethroids,
Because of its low toxicity, low toxicity to fish, and low cost, it can be used as an agricultural and horticultural insecticide or acaricide that replaces conventional organophosphorus agents and organochlorine insecticides. In addition, the compound of the present invention has a chemical structure, for example, it is possible to form a water-soluble salt by adding an inorganic acid such as hydrochloric acid, and most conventional insecticides and acaricides are water-insoluble. Considering this, the practicality of the present invention is extremely large.

Applications of the insecticidal and acaricidal agents of the present invention include sanitary pests such as flies, mosquitoes and cockroaches, organic phosphorus agents,
Carbamate agent resistant leafhoppers, planthoppers,
Agricultural pests such as Nikameichu, stink bugs, armyworm, diamondback moth, tobacco moth, bean weevils, moths, moths, white butterflies, crickets, persimmons, aphids, scale insects, storage pests such as foxgloves, mites, etc., but especially indoor dust It is extremely useful for controlling mites. That is, the present compounds that can be safely used indoors in view of the fact that there are no suitable pyrethroid-based agents for mites, allergic mite, which are said to cause allergic asthma and skin eruption, (Physalis mite mite, Dermatophagoides farinae), and pest mites The creation of is extremely practical.

The insecticidal and acaricidal agent of the present invention can be used as N-octylbicycloheptenecarboximide (trade name: MG
K-264), a mixture of N-octylbicycloheptene dicarboximide and aryl sulfonate (trade name: MGK-5026), synephrine 500, octachlorodipropyl ether, piperonyl butoxide and other synergists. And its insecticidal effect can be further enhanced. In addition to the insecticides and acaricides of the present invention, other insecticides, for example, organophosphorus agents such as fenitrothion, DDVP, diazinon, propaphos, and viridafenthion, NA
Carbamate agents such as C, MTMC, BPMC and PHC, conventional pyrethroid insecticides such as pyrethrin, allethrin, phtalthrin, flamethrin, phenothrin, permethrin, cypermethrin, decamethrin, fenvalerate and fenpropanate, cartap,
Insecticides such as chlorphenamidine and mesomil or acaricides, fungicides, nematicides, herbicides, plant growth regulators,
By mixing a fertilizer and other agricultural chemicals, a multipurpose composition having excellent effects can be obtained, labor saving, and synergistic effects between drugs can be expected sufficiently.

Next, in order to further clarify that the compounds used in the present invention are excellent, the test results of Examples and effects are shown.

[0021]

Example 1 White kerosene was added to 0.3 parts of the compound (1) of the present invention to make 100 parts as a whole to obtain a 0.3% oil solution.

Example 2 White kerosene was added to 0.2 part of the compound (2) of the present invention and 0.8 part of piperonyl butoxide to make 100 parts as a whole to obtain an oil solution.

EXAMPLE 3 Solpor SM-200 was added to 20 parts of the compound (3) of the present invention.
10 parts of Toho Kagaku (registered trademark) and 70 parts of xylol were added and mixed with stirring to obtain a 20% emulsion.

Example 4 0.4 part of compound (4) of the present invention, 0.1 of resmethrin
Parts, 1.5 parts of octachlorodipropyl ether in 28 parts of refined kerosene, filled in an aerosol container, and after attaching a valve portion, 70 parts of a propellant (liquefied petroleum gas) is pressure filled through the valve portion. Then, an aerosol was obtained.

Example 5 0.5 g of the compound (5) of the present invention and 0.5 g of BHT were used as a base material for mosquito coil incense extract such as pyrethrum extracted lees powder, wood powder and den powder.
The mixture was uniformly mixed with 0 g to obtain a mosquito coil according to a known method.

Example 6 0.3 part of the compound (7) of the present invention and 99.7 parts of clay were well pulverized and mixed to obtain a 0.3% powder.

Example 7 40 parts of the compound (10) of the present invention, 35 parts of diatomaceous earth, 20 parts of clay, 3 parts of lauryl sulfonate and 2 parts of carboxymethyl cellulose were ground and mixed to obtain a wettable powder.

Example 8 The compound (14) of the present invention was diluted 3-fold with kerosene,
A kraft paper having a basis weight of 30 g was evenly applied at a rate of 3 g / m ² to obtain a sheet for insecticide and acaricide.

Test Example 1 10 m of the test compound was placed on a 5 cm × 10 cm rectangular filter paper.
0.5 ml of M acetone solution was dropped, and after air-drying, 50 to 150 mites of Dermatophagoides farinae were released while folded in half.
Put these two folded filter papers in two acrylic cylinders (inner diameter 4.1c).
m, height 2 cm) scissors, fixed with a rubber band, the volume is 1 l
Installed in a container with a lid (27-28 ° C., 65% RH), left for 72 hours, then counted the number of live mites and dead mites,
When the acaricidal efficacy of each test compound was examined, it was as shown in Table 2. The pyrethroid compound d-T80-allethrin was used as a control compound.

[0030]

[Table 2]

Test Example 2 An acetone solution of the test compound was prepared so that the weight of the fiber was 0.1% and 0.5% with respect to a test cloth (about 0.65 g) made of 100% wool of 5 cm × 5 cm. Was impregnated with 0.5 ml of an acetone solution having various concentrations, the acetone was volatilized, and then the test was performed. The treated cloths were placed one by one in a glass dish having a diameter of 9 cm, and 10 larvae of squid larvae were released for each test compound and each treatment concentration, and the mortality and the presence or absence of feeding damage were observed after 1 week and 3 weeks. .. In order to see the persistence of efficacy, the test insects were released on the treated cloths immediately after the treatment, 1 month later, and 6 months later. D-T80-allethrin was used as a control drug. The third result
Shown in the table.

[0032]

[Table 3]

As a result of the test, it was revealed that the compound of the present invention has a higher insecticidal effect against mosquito mosquito, which is a harmful insect of clothing, and has a superior residual effect, as compared with the control compound d-T80-allethrin. It was

Example 9 The compound (1) of the present invention obtained by Example 3,
A 1000-fold dilution of the emulsions of (3), (7), (9), (13) and (15) with water was added to a radish field of 5 to 6 leaf stage on one side where many green peach aphids were generated in 100 l /
It was scattered around the cloth. In the parasitism rate survey after 2 days, the density was reduced to 1/10 or less of the density before spraying in each plot.

Example 10 Four leaves of potted green beans, 5 days after sowing, were infested with 10 female adults of the Japanese red mite, Mite mites, per leaf and stored in a thermostatic chamber at 27 ° C. After 6 days, the emulsions of the compounds (3), (4), (7), (11), (14) and (18) of the present invention obtained in Example 3 were diluted with water to 100 ppm of the active ingredient, 10 ml was sprayed per pot on the turntable.
After 10 days, the number of parasites of all the agents was 3 or less in the investigation of the spider mites on the plants.

Example 11 Compounds (2), (6) of the present invention obtained in Example 8,
The insecticidal and acaricidal sheets of (8), (11) and (14) were laid under the tatami mats in which a large number of Phytolacca cerevisiae occurred. After standing at room temperature for 1 month, the condition of mites on the front and back surfaces of the tatami mat was observed. As a result, in each sheet, many dead mites were found on the back surface of the tatami mat, but no live mites were found. Moreover, the presence of live mites was not confirmed on the tatami surface.

[0037]

INDUSTRIAL APPLICABILITY The novel amidine compound represented by the formula I of the present invention has low toxicity to humans and animals, and various pests,
It shows high insecticidal and acaricidal activity against mites. In particular, the high efficacy against indoor dust mites is characteristic compared to conventional pyrethroids, and is highly practical as an effective control agent.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number within the agency FI Technical display location C07D 213/74 6701-4C 317/66 7729-4C (72) Inventor Junro Katsuta Nishinomiya City, Hyogo Prefecture Kotoen 2-10-10 (72) Inventor Kosuke Yoshioka 4-14-24-1004 Koishikawa, Bunkyo-ku, Tokyo

Claims (2)

[Reference number] C754 [Claims] 1. The following formula I: (In the formula, R ₁ is a hydrogen atom, a halogen atom, or a carbon atom of 1
To 4 lower alkyl groups, lower alkoxy groups, lower alkylthio groups, lower haloalkyl groups, lower haloalkoxy groups, lower haloalkylthio groups or methylenedioxy groups. X represents a methine group or a nitrogen atom, and m represents an integer of 1 to 3. R ₂ represents a lower alkyl group having 2 to 4 carbon atoms, a lower alkenyl group, a lower haloalkyl group or an alicyclic group having 3 to 4 carbon atoms. R ₃ is a hydrogen atom, a cyano group, an ethynyl group or a methyl group, and R ₄ is a hydrogen atom or a fluorine atom. R ₅ represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group. ) Amidine derivative represented by. 2. The following formula I: (In the formula, R ₁ is a hydrogen atom, a halogen atom, or a carbon atom of 1
To 4 lower alkyl groups, lower alkoxy groups, lower alkylthio groups, lower haloalkyl groups, lower haloalkoxy groups, lower haloalkylthio groups or methylenedioxy groups. X represents a methine group or a nitrogen atom, and m represents an integer of 1 to 3. R ₂ represents a lower alkyl group having 2 to 4 carbon atoms, a lower alkenyl group, a lower haloalkyl group or an alicyclic group having 3 to 4 carbon atoms. R ₃ is a hydrogen atom, a cyano group, an ethynyl group or a methyl group, and R ₄ is a hydrogen atom or a fluorine atom. R ₅ represents a hydrogen atom, a halogen atom, a methyl group or a methoxy group. ) An insecticide and acaricide containing an amidine derivative represented by