JPH0625155B2 - Pyridazinone derivative, method for producing the same, and insecticide, acaricide and fungicide containing the derivative as an active ingredient - Google Patents

Description

Detailed description of the invention [Industrial application] The present invention relates to a pyridazinone derivative, a process for producing the same, and an insecticide, acaricide and fungicide containing the derivative as an active ingredient. .

(Prior Art and Problems to be Solved by the Invention) Many pyridazinone derivatives have been conventionally known.
Among them, those having insecticidal, acaricidal and bactericidal activity include 5-phenylalkoxy- or 5-phenylalkylthiopyridazinone derivatives (JP-A-58-1528).
78, JP-A-59-98064, JP-A-6.
0-4173, JP-A-60-32774,
JP-A-60-54370) and 5-allyloxy- or 5-allylthiopyridazinone derivatives (JP-A-6-54370).
No. 1-268672) and the like are disclosed,
The following general formula, (In the formula, R ¹ is a lower alkyl group; R ² is a hydrogen atom, a lower alkyl group, a lower alkylthio group, a halogen atom, an alkoxycarbonyl group, etc .; X is a halogen atom; Y and Z
Are independently of each other an oxygen atom or a sulfur atom; n is 1 or 2), and a compound represented by the following general formula: [In the formula, R represents a linear or branched alkyl group having 2 to 6 carbon atoms, A represents a halogen atom, a C1 to C4 alkoxy group or a C1 to C4 alkylthio group, and X is an oxygen atom or a sulfur atom. And B is Or And Y represents an oxygen atom, a sulfur atom or the like, and R ^{1 to} R ²
Is a hydrogen atom or a C1~C4 alkyl ^group, R 3 to R ⁶ is a hydrogen atom, a halogen atom C1~C4 alkyl group, Z is an alkyl group having a straight-chain or branched having 1 to 10 halogen atoms, carbon atoms , C2-C5 alkenyl groups, C
A C2-alkynyl group or the like, and n represents 0 or an integer of 1-5] is disclosed in JP-A-62-277365.

The above-mentioned known compounds have insecticidal, acaricidal, and bactericidal activity, and for example, leafhoppers such as black-necked leafhoppers, pests such as Nijuyahoushitentou, kanzawawa mites, and cucumber bean diseases,
It is also effective against diseases such as cucumber powdery mildew, wheat leaf rust, and rice blast.

However, the compound has insecticidal and acaricidal activities, but its effect is not sufficient.

The inventors of the present invention have conducted extensive studies to obtain a compound having insecticidal, acaricidal and bactericidal activities which are more excellent than those of the above-mentioned known compounds. As a result, 5 of the pyridazinone ring in the above general formula has been obtained.
Having a phenyl group as a substituent at position 4 of the phenyl group
Succeeded in synthesizing a novel pyridazinone derivative having a substituent having a heterocycle or the like at the position, and found that the derivative has remarkably improved insecticidal, acaricidal and bactericidal activities, and completed the present invention. Came to.

[Structure of the Invention] (Means for Solving the Problems) The present invention includes the following formula; [Wherein R ¹ represents a lower alkyl group; R ² represents a halogen atom; R ³ and R ⁴ each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group; Represents; R ⁵ represents —R ⁶ (R ⁶ represents a substituted or unsubstituted saturated heterocyclic group), — (CH ₂ ).
_m -R ^7, or - in the ^{_{(CH 2) m -O-R}} 7 ( each formula, ^{R 7} is 1 or 2 carbon atoms which may be optionally substituted or unsubstituted substituted by hetero atoms constituting the ring Represents a cycloalkyl group, m represents an integer of 1 to 2); A represents a linear or branched alkylene group having 2 to 4 carbon atoms; X and Y are each independently Represents an oxygen atom or a sulfur atom], its production, and an insecticide, acaricide and fungicide containing the derivative as an active ingredient.

In the formula (I), the lower alkyl group represented by R ¹ , R ³ or R ⁴ is a linear or branched alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, amyl group, isoamyl group, sec-amyl group, sec
Examples include -isoamyl group (1,2-dimethylpropyl group) and t-amyl group (1,1-dimethylpropyl group).

The lower alkoxy group represented by R ³ or R ⁴ refers to a linear or branched alkoxy group having 1 to 5 carbon atoms.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group and an amyloxy group.

In R ⁵ , the saturated heterocyclic group represented by R ⁶ is
Examples thereof include an oxolanyl group, a thiolanyl group, a dioxolanyl group, a thiooxolanyl group, an oxanyl group, a dioxanyl group, and an oxothioxanyl group.

In R ⁵ , the cycloalkyl group represented by R ⁷ includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc., wherein 1 or 2 of the carbon atoms constituting the ring are substituted with a hetero atom. Examples of the cycloalkyl group include the above-mentioned saturated heterocyclic group.

In addition, the substituent of the above-mentioned substituted saturated heterobase, cycloalkyl group or cycloalkyl group in which 1 or 2 of the carbon atoms constituting the ring is substituted with a hetero atom may be a methyl group, an ethyl group or the like. Lower alkyl group,
Examples include lower alkenyloxy groups such as allyloxy group and crotyloxy group.

As R ¹ , a tert-butyl group is preferable.

As R ² , a chlorine atom and a bromine atom are preferable.

R ³ is preferably a methyl group, a chlorine atom or a bromine atom.

R ⁴ is preferably a methyl group, a chlorine atom, a methoxy group or a bromine atom.

R ⁵ is a 1,3-dioxolan-2-yl group,
A 1,3-dioxan-2-yl group is preferable, a cyclohexyl group, a cyclopentyl group, and an oxan-2-yl group are preferable as R ⁷ , and 1 is preferable as m.

R ⁵ is a 1,3-dioxolan-2-yl group,
1,3-dioxolan-2-ylmethyl group, oxane-
A 2-yloxymethyl group and a cyclopentyloxymethyl group are preferred.

As A, an ethylene group is preferable.

As X, an oxygen atom or a sulfur atom is preferable.

As Y, an oxygen atom is preferable.

In the above formula (I), when any of the carbon atoms is an asymmetric carbon, the present invention includes both the individual optical isomers and the racemic compound or the mixture.

The compound (I) of the present invention can be easily produced, for example, by a method known per se shown below.

Manufacturing method [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X and Y are as defined above; Z represents a halogen atom] [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , A, X, Y and Z have the same meanings as described above] Production method R ⁵ is substituted or unsubstituted, and is at the 1,3-position. In the case of a cycloalkyl-2-yl group in which a carbon atom is substituted with a hetero atom and the 2-position is alkyl-substituted, it can be synthesized by the following method.

IN FORMULA, R < ¹ >, R < ² >, R < ³ >, R < ⁴ >, A, X AND Y ARE THE SAME MEANING AS THE ABOVE-MENTIONED, R < ⁸ > REPRESENTS A C1-C5 LINEAR OR BRANCHED ALKYL GROUP ′ Represents an optionally substituted alkylene group having 1 to 3 carbon atoms, and X ′ and Y ′
Each independently represent an oxygen atom or a sulfur atom.] As is clear from the above reaction formula, in any of the production methods, hydrogen halide (HX) is eliminated as a result of the reaction. Therefore, it is preferable to carry out the reaction in the presence of a base in order to capture this and carry out the reaction smoothly.

As the base, triethylamine, pyridine, N, N-
Organic bases such as dimethylaniline, organic bases such as naN, N-dimethylaniline, sodium methoxide,
Examples thereof include alkali metal alkoxides such as sodium ethoxide, sodium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, inorganic bases such as potassium carbonate, and the like.

Each of the above reactions is usually performed in the presence of a solvent.
The solvent is not particularly limited as long as it does not participate in this reaction, for example, benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane,
Chlorinated or unchlorinated aromatic, aliphatic, alicyclic carbon hydrogens such as chlorobenzene, dichlorobenzene, methylene chloride, chloroform, dichloroethane, trichloroethylene, cyclohexane; diethyl ether, ethylene glycol dimethyl ether, Ethers such as tetrahydrofuran and dioxane; Ketones such as acetone and methyl ethyl ketone; Alcohols such as methanol, ethanol and ethylene glycol, or water-containing compounds thereof; Amides such as N, N-dimethylformamide, water and Examples include a mixture of the above solvents.

However, when an inorganic base such as sodium hydroxide or potassium hydroxide is used as the above-mentioned base, it is preferable to use water or a mixture of the above solvent and water for dissolving these bases.

When using a mixture of water and a non-hydrophilic solvent,
It is preferable to add a small amount of a phase transfer catalyst, as such a phase transfer catalyst, tetramethylammonium chloride, triethylbenzylammonium chloride,
Quaternary ammonium salts such as tetra-n-butylammonium bromide or tri-n-octylmethylammonium chloride, phosphonium salts such as tetra-n-butylphosphonium bromide, crowns such as dicyclohexano-18-crown-6. Examples thereof include ethers and cryptands.

Although the reaction temperature is not particularly limited, it is usually 0 ° C. or higher and not higher than the boiling point of the solvent used, and it is preferable to heat to shorten the reaction time.

The compounds represented by the general formulas (II), (III), (IV) and (V) used as raw materials in the above-mentioned production method can be easily produced by the following method known per se.

[Wherein R ¹ , R ² , X and Z have the same meanings as described above] [R ³ , R ⁴ , R ⁵ , A, X, Y and Z have the same meanings as described above] In the case of the production method, it is a dehydration reaction as is clear from the reaction formula, and in order to proceed the reaction smoothly, It is preferred to add an acid catalyst.

Examples of the acid catalyst include mineral acids such as hydrochloric acid, sulfuric acid, hydrobromic acid and phosphoric acid, and sulfonic acids such as benzenesulfonic acid and p-toluenesulfonic acid.

Further, in order to remove the generated water to the outside of the reaction system, it is preferable to install a water separator (for example, Dean-Stark trap).

The solvent is not particularly limited as long as it does not participate in this reaction, and the solvents mentioned in the production method and can be used, but aromatic hydrocarbons such as benzene and toluene are particularly preferable.

The general formula (VI) used as a raw material in the above production method can be produced as follows.

Or [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁸ , X, Y and Z have the same meanings as described above] The target compound (I) obtained by the above method is recrystallized,
It can be appropriately purified by a known means such as various chromatography.

The compound of the present invention, hemiptera, for example, planthoppers, leafhoppers, aphids, whiteflies, etc., Lepidoptera, for example, beetles, diamondback moths, leaf beetles, leaf moths,
It shows an excellent effect on agronomic and horticultural pests such as pearl worms, such as weevils, weevil and beetles, as well as mites, such as citrus mites and nematodes. Also flies,
It is extremely effective for controlling hygienic pests such as mosquitoes and cockroaches, and is also effective for stored grain pests.

Furthermore, the compounds of the present invention are also effective against root-knot nematodes, pine wood nematodes, and ticks in soil. Further, the compound of the present invention is also effective for agricultural and horticultural diseases, for example, rice blast disease, barley powdery mildew, cucumber downy mildew,
Active against gray mold and the like.

Thus, the compound of the present invention has a very wide range of uses and applications, is highly effective and can be put to practical use in various dosage forms.

The insecticidal / miticidal and fungicidal agent of the present invention contains one or several compounds of the general formula (I) as an active ingredient. The compound of the general formula (I) may be used as it is, but it is usually mixed with an ordinary carrier, surfactant, dispersant or auxiliary agent and the like by a conventional method, for example, powder, wettable powder, emulsion, It is prepared and used in a composition such as a fine granule, a granule, a water or oily suspension, and an aerosol.

Suitable carriers are, for example, talc, bentonite, clay,
Solid carriers such as kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea,
Kerosene, hydrocarbons such as mineral oil, benzene, toluene, aromatic hydrocarbons such as xylene, chloroform, chlorinated hydrocarbons such as carbon tetrachloride, ethers such as dioxane and tetrahydrofuran, ketones such as acetone, cyclohexanone and isophorone, Examples thereof include esters such as ethyl acetate, ethylene glycol acetate and dibutyl maleate, alcohols such as methanol, n-hexanol and ethylene glycol, polar solvents such as dimethylformamide and dimethylsulfoxide, and liquid carriers such as water. Further, air, nitrogen, carbon dioxide gas, Freon or the like may be used as the gas carrier, and mixed injection may be performed.

Further, as a surfactant or a dispersant for improving the performance of the present agent such as adhesion to animals and plants, improvement of absorption, dispersion of drug, emulsification, spreading, for example, alcohol sulfate ester, alkyl sulfonate , Lignin sulfonate, polyoxyethylene glycol ether and the like are used.

Further, in order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic, etc. are used as an auxiliary agent.

The above-mentioned carrier, surfactant, dispersant and auxiliary agent may be used alone or in combination according to the purpose.

The concentration of the active ingredient when the compound of the present invention is formulated is usually 1 to 50% by weight in an emulsion, 0.3 to 25% by weight in a powder, usually 1 to 90% by weight in a wettable powder, and usually 0 in a granule. 0.5 to 5% by weight, usually 0.5 for oil
It is usually from 0.1 to 5% by weight, and with an aerosol, it is usually from 0.1 to 5% by weight.

These preparations may be diluted to an appropriate concentration and then sprayed on plant foliage, soil, the water surface of paddy fields, or applied directly to each of them to be used for various purposes according to their respective purposes.

(Examples of the Invention) Hereinafter, the present invention will be described in more detail with reference to Examples, but these Examples do not limit the scope of the present invention.

Example 1 2-tert-butyl-4-chloro-5- [2- {2,6-
Synthesis of dichloro-4- (1,3-dioxolan-2-yl) phenoxy} ethylthio] -3- (2H) -pyridazinone (Compound No. 1) 2-tert-butyl-4-chloro-5- [2 (2 , 6-Dichloro-4-formylphenoxy) ethylthio] -3-
A mixture of 0.9 g of (2H) -pyridazinone, 5 m of ethylene glycol, 0.1 g of P-toluenesulfonic acid hydrate and 50 m of benzene was heated under reflux for 4 hours with a water separator.

Then, the reaction solution was cooled, washed with dilute aqueous sodium carbonate and water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.

The obtained oily substance was subjected to column chromatography (Wako Gel C-200, toluene: ethyl acetate = 35: 1 elution).
To obtain 0.8 g of the desired product as a colorless oily liquid.

▲ n ^26.2 _D ▼ = 1.5915 Example 2 2-tert-butyl-4-chloro-5- [2- {2-chloro-4- (1,3-dioxolan-2-ylmethyl)-
6-Methylphenoxy} ethylthio] -3- (2H)-
Synthesis of pyridazinone (Compound No. 4) 2-tert-butyl-4-chloro-5-mercapto-3-
0.7 g of (2H) -pyridazinone and 2-chloro-4-
1.0 g of (1,3-dioxolan-2-ylmethyl) -6-methylphenoxyethyl bromide was dissolved in 20 m of N, N-dimethylformamide, 1.0 g of anhydrous potassium carbonate was added, and the mixture was stirred at room temperature for 8 hours.

After the reaction was completed, the reaction solution was poured into water, and the oily substance that separated was extracted with toluene. The extract was washed with water, dried over anhydrous sodium sulfate, and toluene was distilled off under reduced pressure.

The obtained oily substance was subjected to column chromatography (Wako Gel C-200, toluene: ethyl acetate = 25: 1 elution).
To obtain 0.2 g of the desired product as colorless crystals.

mp 82-83 ° C Example 3 2-tert-butyl-4-chloro-5- [2- {2,6-
Synthesis of dichloro-4-cyclopentyloxymethylphenoxy) ethylthio] -3- (2H) -pyridazinone (Compound No. 5) 2-tert-butyl-4,5-dichloro-3- (2H)-
Pyridazinone 2.2 g and 2- (2,6-dichloro-4-
Cyclopentyloxymethylphenoxy) ethyl mercaptan (3.2 g) was dissolved in methanol (20 m), and sodium methoxide (.0.
A solution of 5 g dissolved in 5 m of methanol was added dropwise. After the dropping, the reaction was completed by stirring at room temperature for 1 hour.

Then, the methanol was distilled off under reduced pressure. Water was added and the oil that separated was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and ethyl acetate was evaporated under reduced pressure. The obtained oily substance was subjected to column chromatography (Wakogel C-200, toluene: ethyl acetate =
(9: 1 elution) to obtain 2.2 g of the desired product as a colorless oily liquid.

N ^25.3 _D = 1.5750 By treating in the same manner as in Examples 1 to 3, compounds shown in Table 1 as compound numbers 2, 3 and 6 to 13 were obtained.

The compound of Comparative Example 1 was also synthesized.

Example 5 5 parts by weight of the compound of Compound No. 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Atlas) and 2 parts by weight of sodium ligninsulfonate are uniformly mixed. Then, a small amount of water was added, and the mixture was kneaded, then granulated and dried to obtain a granule.

Example 6 50 parts by weight of the compound of Compound No. 6, 48 parts by weight of kaolin and 2 parts by weight of neoperex powder (trade name; manufactured by Kao Atlas) were uniformly mixed and then pulverized to obtain a wettable powder.

Example 7 Toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) (10 parts by weight) was added to 20 parts by weight of the compound of Compound No. 12 and 70 parts by weight of xylene, and the mixture was uniformly mixed and dissolved to obtain an emulsion.

Example 8 5 parts by weight of the compound of Compound No. 13, 50 parts by weight of talc and 45 parts of kaolin were uniformly mixed to obtain a dust.

Example 9 Efficacy test against diamondback moth (organophosphorus drug resistor) Cabbage leaf pieces (5 cm) in a plastic cup with a diameter of 10 cm
X 5 cm), while the compounds shown in Table 1 were dispensed according to Example 6, and a chemical solution containing surfactant (0.01%) and adjusted to 300 ppm was sprayed in a spray tower at intervals of 5 m. did. After air-drying, 10 third-instar larvae of Plutella xylostella were tested and allowed to stand in a constant temperature room at 25 ° C., and the number of live and dead larvae was investigated 2 days later to determine the insecticidal rate. The results are shown in Table 2.

For the determination of the insecticidal rate, if the insecticidal rate is 100%, 5,99-
80% is 4, 79-60% is 3, 59-4
0% is represented by 2, 39-20% is represented by 1, and 19-0% is represented by 0, and the insecticidal rate is determined similarly in the following examples.

Example 10 Efficacy test against brown planthopper The compounds shown in Table 1 are prepared according to Example 6, and rice seedlings are squeezed for 30 seconds in a chemical solution containing 300 ppm of water containing a surfactant (0.01%). It was dipped, air dried, and then inserted into a glass cylinder. Ten third-instar larvae of the brown planthopper were released, capped with a porous plug, and allowed to stand in a constant temperature room at 25 ° C. Two days later, the number of live and dead insects was investigated and the insecticidal rate was calculated. The results are shown in Table 3.

Example 11 Efficacy test against leafhopper leafhopper (organophosphorus agent resistance) The compounds shown in Table 1 were prepared according to Example 7, and added to a chemical solution made up to 300 ppm with water containing a surfactant (0.01%). The rice seedlings were dipped for 30 seconds, air-dried, and then inserted into a glass cylinder. 10 fourth-instar larvae of the leafhopper leafhopper, a porous stopper, were left in a constant temperature room at 25 ° C. Two days later, the number of live and dead insects was investigated and the insecticidal rate was calculated. The results are shown in Table 4.

Example 12 Female citrus red mite female (organic phosphorus drug resistant)
Efficacy test against mulberry leaf pieces with a diameter of 20 mm were placed on paper soaked with water, and 10 adult citrus mite females were inoculated. On the other hand, the compounds shown in Table 1 were prepared according to Example 6, and the surfactant (0.
A chemical solution containing 300% of water (01%) was sprayed in a spray tower at intervals of 5 m. After the treatment, the mixture was left in a constant temperature room at 25 ° C., and the number of live and dead insects was examined 3 days later to determine the mortality rate. The results are shown in Table 5.

Example 13 Efficacy test for citrus red mite egg (organic phosphorus drug resistance) A mulberry leaf piece having a diameter of 20 mm was placed on a paper soaked in water, and 5 adult citrus red mite females were inoculated and allowed to lay eggs for 1 day.
On the other hand, the compounds shown in Table 1 were prepared according to Example 6, and a chemical solution containing 300 ppm of water containing a surfactant (0.01%) was sprayed in a spray tower at intervals of 5 m. After processing, 2
After leaving it in a constant temperature room at 5 ° C., the number of unhatched eggs for 10 days was examined to determine the egg killing rate. In addition, the determination of the ovulation rate was performed in Example 9.
The determination was made in the same manner as the insecticidal rate shown in. The results are shown in Table 6.

Example 14 Efficacy test against adult female mites (organophosphorus agent resistance) of green mites, a leaf of leaf of 20 mm in diameter was placed on a paper soaked in water,
10 adult females of the tick mites were inoculated. The leaf pieces were prepared by compounding the compounds shown in Table 1 according to Example 6 into a chemical solution containing water (surfactant (0.01%) and adjusted to 300 ppm).
It was soaked for 15 seconds, air-dried, and then left in a constant temperature room at 25 ° C. After 3 days, the number of live and dead insects was investigated and the acaricidal rate was calculated. The determination of the acaricidal rate was the same as the determination of the insecticidal rate shown in Example 9. The results are shown in Table 7.

Example 14 Efficacy test against scabbard eggs (organophosphorus agent resistance) Egg leaf pieces with a diameter of 20 mm were placed on water-soaked paper,
10 adult females of the spider mite were inoculated and laid for one day. Next, the female adults were removed, and the compound shown in Table 1 was prepared according to Example 6 together with the kidney bean leaf pieces on which eggs were laid, and 300 ppm was added with water containing a surfactant (0.01%).
Soaked in the above chemical solution for 15 seconds, air-dried, then 25 ℃
Left in a constant temperature room. After 8 days, the number of unhatched eggs was examined and the acaricidal rate was calculated. The determination of the egg kill rate was the same as the determination of the insecticidal rate shown in Example 9. The results are shown in Table 8.

Example 16 Efficacy test against Spodoptera litura The compounds shown in Table 1 were prepared according to Example 5, diluted with water containing a surfactant (0.01%) to 300 ppm. On the other hand, soybean leaves were placed in a plastic cup having a diameter of 10 cm, and 10 second-instar larvae of Spodoptera litura were tested on the leaves. The chemical solution prepared above was sprayed on a spray tower for 5 m. Then, it was left in a constant temperature room at 25 ° C., and the number of live and dead insects was investigated 2 days later to determine the insecticidal rate. The results are shown in Table 9.

Example 17 Control effect of cucumber downy mildew The soil was put in a plastic pot and the cucumber was sown. The seedlings cultivated in a greenhouse and having the first leaves developed were formulated with the compounds shown in Table 1 according to Example 7, and a chemical solution diluted with 200 ppm of water containing a surfactant (0.01%) was sufficiently added. The amount was sprayed. 48 hours after spraying, cucumber downy mildew
A spore suspension of (Pseudoperonospora cubensis) was spray-inoculated and left in a room at a temperature of 20 ° C. and a humidity of 100% for 24 hours. On the 10th day after inoculation, the lesion area was visually measured and compared with the lesion area of the untreated section to determine the drug effect. Evaluation is 5-0-5
Indicated in stages, 5 with no lesion, 4 with less than 10% of lesion area compared with untreated area, 3 with 40%, 2 with 40%, 1 with 60%. Is indicated by 0. The results are shown in Table 10.

[Effect of the Invention] According to the present invention, it is possible to provide a novel pyridazinone derivative having an excellent insecticidal effect, acaricidal effect and bactericidal effect.

Front page continuation (72) Inventor Satoshi Fujii 5 1978, Ogushi, Ube, Yamaguchi Prefecture, Ube Laboratory, Ube Research Co., Ltd. Inside the research institute (72) Inventor Akira Ooka 5 in 1978, Kogushi, Ube, Ube City

Claims (7)

[Claims] 1. The following formula: [Wherein R ¹ represents a lower alkyl group; R ² represents a halogen atom; R ³ and R ⁴ each independently represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom or a nitro group; Represents; R ⁵ represents —R ⁶ (R ⁶ represents a substituted or unsubstituted saturated heterocyclic group), — (CH ₂ ).
_m -R ^7, _{or, - (CH 2) m -O} -R 7 ( in each formula, ^{R 7} is 1 or 2 of the carbon atoms constituting the ring
Represents a substituted or unsubstituted cycloalkyl group which may be substituted with a hetero atom, m represents an integer of 1 to 2), and A represents a linear or branched carbon number 2 Represents an alkylene group of 4 to 4; and X and Y each independently represent an oxygen atom or a sulfur atom.]. 2. The following formula: [Wherein R ¹ and R ² have the same meanings as in claim 1 and Z represents a halogen atom], and a compound represented by the following formula: [Wherein R ³ , R ⁴ , R ⁵ , A, X, and Y are each defined by the formula 1
It has the same meaning as the above.] The method for producing a pyridazinone derivative according to claim 1, wherein the pyridazinone derivative is reacted. 3. The following formula: [Wherein R ¹ , R ² and X have the same meanings as in claim 1] are represented by the following formula: [Wherein R ³ , R ⁴ , R ⁵ , A and Y have the same meanings as in Claim 1 and Z has the same meanings as in Claim 2]. A method for producing the pyridazinone derivative described. 4. The following formula: IN FORMULA, R < ¹ >, R < ² >, R < ³ >, R < ⁴ >, A, X AND Y ARE THE SAME SYMBOLS OF Claim 1, R < ⁸ > IS A C1-C5 LINEAR OR BRANCHED ALKYL GROUP. Represents a compound represented by the following formula: [Wherein A'represents an optionally substituted alkylene group having 1 to 3 carbon atoms, and X'and Y'independently represent an oxygen atom or a sulfur atom]. The method for producing a pyridazinone derivative according to claim 1, wherein 5. An insecticide containing the pyridazinone derivative according to claim 1 as an active ingredient. 6. An acaricide containing the pyridazinone derivative according to claim 1 as an active ingredient. 7. A fungicide containing the pyridazinone derivative according to claim 1 as an active ingredient.