JPH03261771A - Nitroaniline derivative, production thereof and bactericide and insecticide for agriculure and horticulture containing the same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R<1> is H or alkyl; R<2> is H, halogen, alkyl, phenyl, alkoxycarbonyl, cyano, nitro or acyl; R<3>, R<4> R<5> are H, halogen nitro or halogen-substituted alkyl) or a salt thereof. EXAMPLE:N-(3-Trifluoromethyl-4-phenylisooxayol-5-yl)-4-trifluoromethyl -2,6 dinitroaniline. USE:Agricultural or horticultural bungicide or insecticide. Particularly, the compound exhibits excellent control activities against insects such as green peach aphid and tobacco cutworm and mites, and also against the clubroot, of Cruciferae plants, rice blast, cucumber powdery mildew, etc. PREPARATION:A compound of formula II is reacted with a compound of formula III (X is a releasable group) in the presence of a base (e.g. KOH) is a solvent such as dimethyl formamide at -10 to 150 deg.C to provide the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel nitroaniline derivative, a method for producing the same, and an agricultural and horticultural fungicide/insecticide containing the same as an active ingredient.

N-substituted diallylamine derivatives for agricultural and horticultural purposes have been known to exhibit a wide range of biological activities as sea lion alar agents (uncoupling agents), such as compounds shown in Table 1 below. are commercially available or disclosed.

<Margin below> Table 1 However, these pesticides are not necessarily satisfactory, and safer pesticides that exhibit better effects are desired.

Therefore, as a result of intensive research to provide a compound that exhibits even better biological activity, the present inventors discovered a new compound that has a completely different chemical structure from the above-mentioned known compounds in that it has an isoxazole group. The present inventors have discovered that nitroaniline derivatives exhibit unprecedented bactericidal and insecticidal effects even at low concentrations, leading to the completion of the present invention.

That is, the present invention provides a compound represented by the following formula (r).

(In the formula, R' is a hydrogen atom or an optionally substituted alkyl group, R2 is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an optionally substituted phenyl group, an alkoxycarbonyl group, The above general formula (1 ) is as follows.

In the above and below descriptions, "optionally substituted alkyl group" refers to unsubstituted or substituted with a halogen atom, hydroxyl group, acylamino group, acyloxy group, amino group, mono- or di-substituted amino group, etc. A straight or branched chain saturated hydrocarbon residue having 1 to 7 carbon atoms. This alkyl group includes methyl, ethyl, propyl,
Isopropyl, butyl, isobutyl, sec-butyl, tertiary-butyl, pentyl, isopentyl, tertiary-pentyl, neopentyl, l-methylbutyl, l.

2-dimethylbutyl 5-hexyl, heptyl, etc. are included, and at any position of these alkyl groups, one or more halogen atoms, water 11 acylamino group, acyloxy group, amino group, monosubstituted amino group (alkylamino, etc.) , alkyl groups substituted with di-substituted amino groups (dialkylamino, etc.), and the like.

"Halogen atom" includes chlorine atom, bromine atom, iodine atom and fluorine atom.

"Optionally substituted phenyl group" refers to unsubstituted phenyl group or halogen atom, hydroxyl group, acylamino group, acyloxy group, amino group, 7- or di-substituted amino group, alkoxycarbonyl group, cyano group, nitro group. , refers to a phenyl group substituted with a substituted sulfonyl group, an alkyl group, an alkoxy group, etc., and suitable substituted phenyl groups include fluorophenyl, chlorophenyl, dichlorophenyl, trifluoromethylphenyl, and the like.

"Alkoxycarbonyl group" refers to a carbonyl group substituted with an alkoxy group having 1 to 7 carbon atoms, and suitable alkoxycarbonyl groups include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, and the like.

In addition, suitable r-acyl groups include formyl, acetyl,
Includes propionyl, butyryl, valeryl, benzoyl, etc.

"Alkyl group substituted with one or more halogen atoms" means the alkyl group substituted with the halogen atom, and the alkyl group substituted with one or more appropriate halogen atoms includes trifluoro methyl,
Includes trichloromethyl, chlorofluoromethyl, monofluoromethyl, difluoromethyl, etc.

This invention also includes salts of the above compounds. Suitable salts include alkali metal salts such as sodium and potassium salts, alkaline earth metal salts such as calcium and magnesium salts, ammonium salts, and organic amine salts such as diethylamine, triethylamine, and pyridine.

The compounds of this invention can be prepared as shown below.

(Production method) A compound represented by the general formula (■): 2 (wherein R1 and R: have the same meanings as defined above) is added to a compound represented by the general formula (■): 4 (wherein R3, R4 and R5 are It has the same meaning as the above definition, and X represents a leaving group).

In the above general formula (III), included.

This reaction is usually carried out in a solvent. Examples of the N medium include aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, and N-methylpyrrolidone; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; alcohols such as methanol, ethanol, and propatool; Ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic hydrocarbons such as benzene and toluene, mixtures of the above solvents, or mixtures of the above solvents and water are used.

Further, this reaction is preferably carried out in the presence of a base (I! acceptor). Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. Inorganic bases such as trimethylamine, triethylamine, pyridine and the like are used.

The reaction temperature is preferably -10 to 150°C, particularly 0 to 30°C.

Suitable reaction time is 1 to 48 hours, particularly 2 to 24 hours.

Some of the raw material compounds represented by general formulas (II) and (III) are publicly known (for example, disclosed in JP-A No. 62-96479), and those that are not publicly known can be produced by methods similar to or similar to known ones. .

If necessary, the reaction product is concentrated by a conventional method, extracted with an appropriate solvent, recrystallized, subjected to vacuum distillation or column chromatography, etc. to isolate and produce the desired product, and further if necessary. Salt. The obtained compound can be further converted into its derivative by conventional methods.

4 Mitachisha 1 The compound of the present invention has excellent insecticidal activity against plant pests belonging to insects, mites, nematodes, and the like. In particular, it has an excellent control effect on insects that damage various plants, such as peach aphid, armyworm, diamondback moth, and black leafhopper, as well as mites, such as two-spotted spider mite, red-spotted spider mite, and citrus spider mite.

Furthermore, the compounds of the present invention have excellent effects on controlling infectious diseases caused by bacteria, filamentous fungi, and viruses. especially,
It exhibits excellent control effects against pathogens such as clubroot, rice blast, rice sheath blight, cucumber powdery mildew, cucumber downy mildew, cucumber gray mold, and potato scab.

Furthermore, the compounds of the present invention are agricultural f! : It does not cause any chemical damage to objects or garden crops, or even if it does, the damage is easily reversible.

When the compound of this invention is used as an agricultural and horticultural fungicidal or insecticide, it may be mixed or combined with agricultural chemical auxiliaries as in the case of conventional agricultural chemical formulations to form emulsions, powders, fine granules, or granules. It is formulated into dosage forms such as , wettable powders, and flowables.

The I content of the compound of this invention in the formulation varies depending on the dosage form, method of use, and other conditions, but is usually 0.
．． It ranges from 2 to 99% by weight, preferably from 0.5 to 70% by weight. However, in some cases, the compound of this invention may be used alone.

Examples of the agricultural chemical auxiliary agents mentioned above include carriers (diluents) and auxiliary agents thereof, such as spreading agents, emulsifiers, wetting agents, dispersing agents, fixing agents, and disintegrants.

The carrier may be either liquid or solid. Examples of liquid carriers include aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone and ketone, and dimethylformamide. Examples include amides such as, sulfoxides such as dimethyl sulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids, and fatty acid esters. Examples of solid carriers include clay, kaolin-5 talc, diatomaceous earth, silica, calcium carbonate, morillonite, bentonite, feldspar, quartz, and alumina.

Surfactants are usually used as emulsifiers or dispersants, such as anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine, as well as cationic surfactants. activator,
Nonionic surfactants and regenerating ionic surfactants are also used.

Spreading agents include polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl ether; wetting agents include polyoxyethylene nonylphenyl ether and dialkyl sulfosuccinate; and fixing agents include carboxymethyl cellulose and polyvinyl alcohol. Examples of disintegrants include sodium pyrogenin sulfonate and sodium lauryl sulfate, which are used depending on the purpose of use.

In actual use, the preparation thus prepared is used directly as it is or after being diluted to a desired concentration.

The amount used varies depending on the dosage form, method of use, timing, and other conditions, but for example, for powders, it is 50 to 500 g of active ingredient per 10 are, and for granules, it is 50 to 500 g of active ingredient per 10 are.
g, the active ingredient in emulsions ranges from 2 to 5 g. However, in special cases it is possible, and sometimes even necessary, to exceed or fall below these ranges.

These preparations are generally used for foliage treatment or soil treatment; in the case of soil treatment, the preparations are sprayed on the soil surface or perfused into the soil.

Target soils include normal soils such as sandy loam and loam, as well as planted soil and sandy soil.

Any of the preparations can be used not only alone, but also in combination with other agricultural and horticultural fungicides, insecticides, plant growth regulators, acaricides, etc., or simultaneously without mixing.

This invention will be explained in more detail with reference to Examples below.
The effects of this invention will be clarified through test examples.

East JL Example 2 (Production of target compound) N-(3-)lifluoromethyl-4-phenylisoochylizo-5-yl)-4-trifluoromethyl-2,
685 mg (3 mmo/) of base 5-amino-4-phenyl-3-trifluoromethylinoxazole of 6-sinitroaniline (compound No. 16) was dissolved in 6 ml of dry dimethylformamide, and powdered 85%
Add 0.40g (6mm01) of potassium hydroxide,
Stirred at room temperature for 45 minutes. Add 4-chloro-3,5 to this solution.
-Dinitrobencitrifluoride 1.06g (3,
9 mmol 1) was added thereto, and the reaction was carried out at room temperature.

After 23 hours rrI, ice water was added, the pH was adjusted to 1 with concentrated hydrochloric acid, and the mixture was extracted with ether. The ether layer was washed with water, dried over anhydrous sodium sulfate, and the ether was distilled off under reduced pressure to obtain crude crystals. The crystals were purified by column chromatography packed with silica gel, and 1.40 g of the obtained crystals were recrystallized from ethyl acetate-n-hexane with a melting point of 132.5-1.
756 mg of orange-yellow needle crystals at 33.5°C (yield: 54.
5%).

The properties of the compounds obtained in the above examples and the compounds obtained by a similar method are shown in Table 2 below.

Table 2 (margins below) Table 2 (continued) In Table 2, Me is a methyl group, pH is a phenol group, and t-
Bu represents a tertiary butyl group, COOMe represents a methoxycarbonyl group, and C00Et represents an ethoxycarbonyl group.

Regarding compound No. 20, the IR spectrum vmax (CHC/ 3 ) was shown instead of the melting point.

(Production of raw material compounds) Compounds represented by general formulas (II) and (III), which are raw material compounds, were produced using known methods or methods similar to known methods, as shown in Table 3 below, for example.

(The following is a blank space) Table 3 Below is a formulation example of the agricultural and horticultural fungicidal/insecticide of the present invention containing the compound obtained according to Example 1 as an active ingredient.The test compound No. is Example 1. (corresponds to compound No. shown in Table 2) (the same applies to the following descriptions).

Number "Aimgo 1", Powder (parts by weight) Compound N013・・・・・・・・・・・・・・・
・・・・・・ 5 talc ・・・・・・・・・
・・・・・・・・・・・・・・・ 46 clay ・
・・・・・・・・・・・・・・・・・・・・・・・・ 4
9. Mix and grind the above ingredients uniformly to make a powder.

4 spoonfuls Hydrating agent (parts by weight) Compound N018・・・・・・・・・・・・・・・・・・
・・・・・・ 50 Kaolin ・・・・・・・・・
・・・・・・・・・・・・・・・ 45 Sodium higher alcohol sulfate... 3 Sodium lignin sulfonate b... 2 The above is mixed and pulverized uniformly to make a wettable powder.

4. Granules (parts by weight) Compound No. 15・・・・・・・・・・・・・・・・・・
・・・・LO diatomaceous earth ・・・・・・・・・・・・
・・・・・・・・・・・・ 35 Bentonite ・・・・
・・・・・・・・・・・・・・・・・・・・・ 23 Talc ・・・・・・・・・・・・・・・・・・・・・
・・・・・・ 30 Disintegrant ・・・・・・・・・・・・
・・・・・・・・・・・・・・・ 2 Mix the above evenly, add 18 parts by weight of water to make it evenly moistened, extrude through an injection molding machine, granulate it, and then size it with a sizing machine. After that, dry
It is made into granules with a particle size of 0.6 to 1 mm.

4 Owata 1 Fine grains (parts by weight) Compound No. 20・・・・・・・・・・・・・・・・・・
・・・・・・ 6 polyvinyl alcohol・・・・・・・・・
・・・・・・・・・ 6 clays ・・・・・・・・・
9. Mix and grind the above ingredients uniformly to make a thick powder.

Separately, 80 parts by weight of oil well-absorbing mineral coarse powder of 74 to 105 μm is placed in a suitable mixer, and 20 parts by weight of water is added while rotating to uniformly wet the mixer. The above-mentioned thick powder is added to this, coated, and dried to form fine granules.

[5 Emulsion (parts by weight) Compound No. 25 ・・・・・・・・・・・・・・・
・・・・・・ 20 xylene′ ・・・・・・
・・・・・・・・・・・・・・・ 63 Alkylphenol ethylene〉Mixture of oxide condensate and alkylbenzenesulfonic acid calcium ・・・17 (molar ratio 8.2) Compound No. 25 in xylene The above mixture is added to the solution, mixed and dissolved to form an emulsion.

As described above, the compound of this invention exhibits excellent bactericidal and insecticidal effects even at low concentrations, and is an extremely useful compound as a bactericidal and insecticidal agent for agricultural and horticultural purposes. The test results of its bactericidal and insecticidal effects are shown below.

Trial m Brassicaceae clubroot disease control effect test (sample preparation method) The compound according to the present invention was dissolved in a small amount of dimethylformamide, and the compound was dissolved in T w e n 20 (Hani Kagaku I!).
Distilled water containing 1100 pp was added to dilute the solution to a predetermined concentration.

(Test method) Nekobu bacterium (PIas+*odio harm bra
sicie) Contaminated soil (sandy loam > 250 g in 7 cm square plasti soil (1,' 20000 a)
The soil was then irrigated with 20ml of the test solution. 25
After being left at ℃ for 24 hours, the soil was mixed, six Chinese cabbage (ideal Chinese cabbage) seeds were sown per pot, and the Chinese cabbage was grown in a glass chamber.

<Judgment method> After 5 weeks, the condition of root nodule formation was examined according to the following criteria, and the severity of the disease (nodule formation index) was determined.

Class value of lump formation status: O: No growth of aneurysms was observed.

1: Nodules are seen on the lateral roots, but the degree of hypertrophy is small.

2: There are enlarged nodules on the lateral roots, or moderately enlarged nodules on the main root.

3: An enlarged knob is seen on the taproot.

4: Root threads are occupied by enlarged nodules, and fine roots are hardly seen.

Using this disease severity, the control rate was calculated as shown below and the activity was evaluated.

(Test Results) Table 4 shows the test results for the compounds of this invention.

In addition, as a comparative example, commercially available Daconil 0, PC
Similar test results are shown for NB, triclamide and fluazinam, where the compounds of the present invention were used at a treatment concentration of 7.8 pPm, whereas most of these comparative compounds were used at a treatment concentration of 31.3 pPm. 125,5
It was used as 00 ppm.

(Margin below) Table 4 Club club disease control effect of cruciferous vegetables No. Table (continued) experience (Test solution preparation method) It was prepared in the same manner as Test Example 1.

(Test method) Unless otherwise stated in A to E below, in the preventive effect test, test plants were sprayed with the test solution, and pathogenic bacteria were inoculated 24 hours later. In the therapeutic efficacy test, pathogenic bacteria were inoculated into test plants in advance, and when slight disease symptoms were observed (inoculation 24~
After 48 hours, the test solution was sprayed.

A. Rice blast control effect test Two weeks after sowing, rice (variety: Aichi Asahi) seedlings were transplanted into plastic cups with a diameter of 9 cm, and after raising the seedlings for another two weeks, a test solution (solution or suspension) was sprayed on the stems and leaves. Inoculation of the pathogen was carried out by spraying a conidial suspension of the rice blast fungus (Prieularia vulgaris) cultured in oatmeal medium, and after inoculation, the inoculation was carried out in a greenhouse (28°C, 100% relative humidity). The seedlings were kept for 24 hours and then grown in a greenhouse for 5 days. Six days after inoculation, the number of lesions appearing on the inoculated leaves was measured, and the control rate was determined as shown below.

B. Rice sheath blight control effect test Two weeks after inoculation, rice (variety: Aichi Asahi) seedlings were transplanted into plastic cups with a diameter of 9 cm, and after raising the seedlings for another two weeks, a test solution (solution or suspension) was applied to the stems and leaves. The pathogen was inoculated using rice sheath blight fungus (R) cultured in advance on rice husk medium.
The mycelium of h1zoctonia 5olani) is placed on the ground of rice seedlings together with a rice husk medium.
After inoculation, the seedlings were grown for an additional 5 days in a greenhouse (28°C, relative humidity 100°).The investigation was conducted by measuring the height of mycelia extending to the rice leaf sheath, and the control rate was determined as shown below.

C. Cucumber powdery mildew control effect test: Seed in a plastic cup with a diameter of 9 cm, and after 2 to 3 weeks of seedling growth, test the solution (solution or suspension) on the surface of the first true leaf of cucumber (variety: Tsukuba Shirobo) seedlings. Inoculation of the pathogen was carried out by spraying a conidial suspension of cucumber powdery mildew (S haerotheca 7) cultured on cucumber leaves. After inoculation, the inoculation was carried out in a greenhouse at 20°C for 10 days. After the inoculated leaves were incubated, the area occupied by the symptoms that appeared on the inoculated leaves was investigated and the control rate was determined as shown below.

D. Cucumber and disease control effect test After seeding in a plastic cup with a diameter of 9 cm and raising the seedlings for 2 to 3 weeks, a test solution (solution or suspension) was applied to the surface of the first true leaf of cucumber (variety: Tsukuba Shirobo) seedlings. The inoculation of pathogenic bacteria was carried out by inoculating cucumbers cultured on cucumber leaves and pathogenic bacteria (P
seudo eronos oracubensis)
This was carried out by dropping a suspension of zoospores II on the underside of cucumber leaves. After inoculation, the seeds were kept in a greenhouse at 20°C for 10 days, and the degree of lesion development around the inoculated area was investigated to determine the control rate as shown below.

E. Cucumber Gray Mold Control Effect Test The seeds were sown in a plastic cup with a diameter of 9 cm, and after 2 to 3 weeks of seedling growth, a test solution (solution or suspension) was applied to the surface of the first true leaf of cucumber (variety: Tsukuba Shirobo) seedlings. was sprayed. Inoculation of the pathogen was carried out by placing hyphal disks (φ4 mm) of gray mold fungus (17 einerea) cultured on a potato decoction agar medium supplemented with sucrose on the surface of cucumber leaves. After inoculation, the seeds were kept in a greenhouse at 20°C for 2 days, and the lesion diameter was measured to determine the control rate as shown below.

(Judgment method) The control rate was calculated from the formula below.

Control rate (%) The test results of the above A regarding the compound of this invention are shown in Table 5.
The test results of B above are shown in Table 6, the test results of C above are shown in Table 7, the test results of above are shown in Table 8, and the test results of E above are shown in Table 9.
Shown in the table.

Table 5: Effect on controlling rice blast disease (white space below) (test results) Table 6: Effect on controlling rice blast disease (white space below) (white space below) Table 8: Effect on controlling rice blast disease (white space below) Table 8: Effect on controlling rice blast disease Potato scab control effect test (test solution preparation method) Prepared in the same manner as in Test Example 1.

(Test method) Potato scab contaminated soil (103 spores/g soil >4
Put kg into a 1/5000a Wagner pot,
100 ml of test solution was poured onto this.

After 24 hours, the soil in the pot was thoroughly mixed, and potato seeds were planted and grown in a glass room.

After about two months, the potatoes were dug up and the extent of the disease was examined.

(Judgment method) Try @l! The determination was made in the same manner as No. 112.

(Test Results) Table 10 shows the test results for the monsters of this invention, and the test results for commercially available products as comparative examples are also shown in the table.

Table 10 Potato scab control effect 4 ships” Insecticidal effect test (Test solution preparation method) It was prepared in the same manner as Test Example 1.

(Test method) A. Green peach aphid larvicidal (larvicidal) test diameter 3c
M Chinese cabbage leaf pieces were placed on 0.3% agar gel with the back side up, inoculated with ignorant adults, and kept at 25°C for 1 day.
The spawned larvae were counted. After removing the adult insects, a test solution of a predetermined concentration was sprayed using an automatic chemical spraying device, and the specimens were kept at 25° C. After 48 hours, the presence of reaction (evacuation and dead insects) was examined.

B. Spodoptera larvaecidal test A piece of Citrus orchid leaf (5y 5 cm) was immersed in a test solution of a predetermined concentration, the drug was applied to the front and back of the leaf, and then dried indoors. (raised indoors for generations)
Seventy-seven leaf pieces from 10 insects were released, placed in a petri dish with a diameter of 9 cm, and kept at 25° C. 48 hours later, the mortality rate and degree of feeding damage were investigated.

C. Larvicidal test for diamondback moths A piece of Citrus orchid leaf (5 x 5 cm) is immersed in a test solution of a predetermined concentration, the drug is applied to the top and bottom of the leaf, and then dried indoors. Breeding) 109.
The leaf pieces were released and placed in a petri dish with a diameter of 9 cm and kept at 25° C. After 48 hours, the mortality rate and the degree of feeding damage were investigated.

D. Adult female leafhopper killing test 6 to 7 paddy rice seedlings of 2 to 5 leaf age are bundled together, the root area is wrapped with a sponge, set in a 6 cm diameter polycup, and this is covered with a cylinder made of wire mesh to remove female adult insects (paddy rice seedlings). Approximately 10 insects were released from a reared population.

A test solution of a predetermined concentration was sprayed onto this using an automatic chemical spraying device.

After the treatment, the temperature was kept at 25°C, and the mortality rate was examined 48 hours later.

E-1, Two-spotted spider mite adulticidal test A primary leaf piece of common bean with a diameter of 2 cm was placed with the back side up on a 0.3% agar gel, and a female adult (susceptible population reared for generations on common bean leaves) was placed on it for 12jl1. Inoculated before and after, kept at 25℃ for 1 day, removed dead and weakened types, and sprayed with a test solution of a specified concentration using an automatic chemical spraying device.
After 48 hours of keeping at ℃, the mortality rate was examined.

E-2. Two-spotted spider mite ovicidal test A primary leaf piece of common bean with a diameter of 2 cm was placed with the back side facing up on a 0.3% agar gel, and an adult female bean (susceptible population reared for generations on common bean leaves) was placed on this for 7 days. After inoculating before and after the head and allowing them to lay eggs for one day at 25°C, remove the adults, spray a test solution with a predetermined concentration using an automatic chemical spraying device, and keep at 25°C.
After 168 hours, the killing rate was determined from the number of dead insects.

<Test Results> The test results of the above A for the compound of this invention are shown in Table 11, the test results of the above B are shown in Table 12, the test results of the above C are shown in Table 13, the above test results are shown in Table 14, and the above test results are shown in Table 14. The test results for E-1 and E-2 are shown in Table 15, and the test results for commercially available products are also shown in the table as comparative examples.

(See the blanks below) Table 1 Table 12 Insecticidal effect on Spodoptera spp. S: Sensitive to organic phosphorus agents and carbamate agents R: Resistant to organic phosphorus agents and carbamate agents (See the blanks below) Table 13 Insecticidal effect on diamondback moth

Claims (3)

[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 optionally substituted alkyl group, R^2 is hydrogen Atom, halogen atom, optionally substituted alkyl group, optionally substituted phenyl group, alkoxycarbonyl group, cyano group, nitro group or acyl group, R^3, R^4 and R^5 are each the same or a salt thereof, which is different from a hydrogen atom, a halogen atom, a nitro group, or an alkyl group substituted with one or more halogen atoms. (2) General formula (II): ▲Mathematical formulas, chemical formulas, tables, etc.▼...(II) (In the formula, R^1 is a hydrogen atom or an optionally substituted alkyl group, R^2 is hydrogen a halogen atom, an optionally substituted alkyl group, an optionally substituted phenyl group, an alkoxycarbonyl group, a cyano group, a nitro group, or an acyl group.
II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III) (In the formula, R^3, R^4, and R^5 are each the same or different and represent a hydrogen atom, a halogen atom, a nitro group, or 2. A method for producing a compound according to claim 1, which comprises reacting a compound represented by the following formula (X represents a leaving group): an alkyl group substituted with one or more halogen atoms. (3) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼...(I) (In the formula, R^1 is a hydrogen atom or an optionally substituted alkyl group, R^2 is hydrogen atoms, halogen atoms, substitutions,
an optionally substituted alkyl group, an optionally substituted phenyl group, an alkoxycarbonyl group, a cyano group, a nitro group or an acyl group, R^3, R^4 and R^5 are each the same or different and each represents a hydrogen atom , halogen atom,
A nitro group or an alkyl group substituted with one or more halogen atoms. Disinfectants and insecticides.