JPH02167204A - Harmful living thing-controlling agent - Google Patents

Abstract

PURPOSE:To obtain a harmful living thing-controlling agent containing an imidazole based compound and other specific compound as active ingredients, reduced in used chemical amount, having wide controlling spectrum and especially useful for rice blast disease as a germicide for agriculture and horticulture. CONSTITUTION:The harmful living thing-controlling agent containing at least one kind of imidazole based compound expressed by the formula (R<1> is phenyl which may be replaced by a halogen atom or alkyl which may be replaced by halogen) and at least one kind of azole based compound, quinoxaline based compound, dithiocarbamate based compound, pyridazinone based compound, etc., or sprout and produced crystalline toxin of Bacillus thuringiensis bacterium as active ingredients. Furthermore, the compound expressed by the formula is synthesized by reaction as shown in the reaction formula.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a pest control agent containing a compound represented by general formula (1) below and other specific compounds as active ingredients.

[Conventional technology]

The compound represented by the general formula (1) below is a new compound useful as a pest control agent, and has been filed by the present applicant as Japanese Patent Application No. 1983-57920.

On the other hand, other specific compounds used in combination with the compound represented by formula (1) in the present invention are already known to be effective as pest control agents.

[Background of the invention]

The compound represented by the general formula (1) below and many pest control agents that have been provided to date have their own characteristics in terms of their pest extermination effects, and therefore some are effective against specific pests. Some of them are not effective enough, others have somewhat inferior therapeutic effects compared to preventive effects, or have relatively short residual effects, and depending on the application situation, they may be practically ineffective against pests. It may not show sufficient control effect.

As a result of research to solve these problems, the inventors of the present invention found that
By using the compound represented by general formula (1) below in combination with other specific compounds, the amount of each drug used can be reduced compared to when each compound is used alone, In addition, we have found that more effective effects than expected can be obtained, such as being able to expand the pest control spectrum.

[Disclosure of the invention]

The present invention is represented by the general formula (I): (wherein, R1 is a phenyl group which may be substituted with a halogen atom or an alkyl group which may be substituted with a halogen atom, and Rt is a halogen atom). At least one type of 4-ξdazoyl compound, an azole compound, a quinoxaline compound, a dithiocarbamate compound, an organochlorine compound, a benzimidazole compound, a pyridazinone compound, a cyanoacetamide compound, a phenylamide compound , sulfenic acid compounds, copper compounds, isoxazole compounds, organic phosphorus compounds, N
-Halogenothioalkyl compounds, dicarboxylic compounds, benzanilide compounds, benzalido compounds, piperazine compounds, pyridine compounds, pyrimidine compounds, piperidine compounds, morpholine compounds, organotin compounds, urea compounds, cinnamic acid compounds, carbamate compounds, pyrethroid compounds, benzoylurea compounds, thiazolidine compounds, thiadiazine compounds, neraistoxin derivatives, pyridazinone compounds, or live spores and produced crystals of Bacillus thuringiensis. The present invention is a pest removal agent characterized by containing at least one type of toxin as an active ingredient.

In the definition of the compound represented by the general formula (1), examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The compound represented by the general formula (1) above means:

Representative examples of these compounds are listed in Table 1.

Table 1 (!a) (Ib) Among the compounds listed in Table 1 above, compounds with b appended after the compound magnetism have the formula (1-b) above.
The compound represented by (:1) is a mixture of the -C formulas (1-a) and (1-b).

In the present invention, examples of the partner compound to be used in combination with the compound represented by the general formula (1) include the following compounds.

Kinoxane is put into 'Blood 1 [4 Washing' 3E Wings GJ3 Straw master Z' 4L [Kaku±11' Mutual, 12ff Yosuji founding Pipagin Ujin tail m color coarse alternation ± 1 self-adhesive hill development - Kintate L2A1" Yoototsuke Hagihi Among the above partner drugs, azole compounds, quinoxaline compounds, Diocarbamate compounds, organic chlorine compounds, benzimidazole compounds, viridinamine compounds, cyanoacetamide compounds, phenylamide compounds, sulfenic acid compounds, copper compounds, isoxazole compounds, organic phosphorus compounds, Dicarboximide compounds, benzanilide compounds and benzamide compounds are preferred, and the compounds NILB-3 (riflumizole), C-1 (chinomethionate), D-3 (mancozeb), E-2 (chlorothalonil), F-1 ( benomyl), G-1 (fluazinam), H-1 (cymoxanil)
, I-1 (metalaxyl), l-2 (oxaxyl)
, J-1 (diclofluanid), K-1 (cupric hydroxide), L-1 (hydroxyisoxazole), M-1 (fosetyl aluminum), 0-1 (procymidone),
P-1 (flutolanil) and Q-1 are particularly desirable.

The novel imidazole compound represented by the general formula (1) can be produced, for example, by the following method.

Method (1) (wherein Z is a hydrogen atom, a chlorine atom or a bromine atom,
Y is a chlorine atom, a fluorine atom, a bromine atom or an iodine atom, Y' is a chlorine atom, a bromine atom or an iodine atom, and R'
is as described above).

Method (2) 1R2 10-150°C, 1 to 48 hours (In the formula, Y, R' and R1 are as described above.) The above method (Step 11 and Method (2) may be carried out as necessary. hand,
It is carried out in the presence of a solvent and an acid acceptor.

? Examples of carriers include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; and cyclic or non-cyclic aliphatic hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, n-hexane, and cyclohexane. Ether necks such as diethyl ether, dioxane, and tetrahydrofuran: acetone,
Examples include ketones such as methyl ethyl ketone and methyl isobutyl ketone; nitriles such as niacetonitrile and propionitrile; and aprotic polar solvents such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide and sulfolane.

The acid acceptor may be either an inorganic base or an organic base. Examples of the inorganic base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as anhydrous potassium carbonate and anhydrous calcium carbonate. Examples include carbonates of metals or alkaline earth metals; alkali metal hydrides such as sodium hydride; alkali metals such as sodium metal; and examples of organic bases include triethylamine. The above reaction can also be carried out in the presence of a suitable catalyst.

Examples of this catalyst include phase transfer catalysts such as quaternary ammonium salt derivatives.

The compound represented by the general formula (n) can be produced, for example, by the following method or a method similar thereto.

Method (3) [When R3 is a hydrogen atom in compound (III)] (
In the formula, Rj is a hydrogen atom or a halogen atom, and R'
is as described above) In addition, since the compound represented by the general formula (U) has a tautomer represented by (wherein R1 and R2 are as described above), the general formula ( When the compound represented by the general formula (1) is produced using the compound represented by II) as a raw material, the compound represented by the general formula (1-a) and/or the compound represented by the general formula (1-b) A compound is obtained.

In this way, 13OJ is added to the raw material compound in which tautomers exist.
(C1!3)! A mixture or one of the two isomers is obtained as a result of the reaction for introducing the group, and whether a mixture or one of the isomers is obtained depends on the compound used as the raw material, It is determined by the type of reaction from the raw material to the target product, each reaction condition, etc. If a mixture is obtained, its mixing ratio is similarly determined.

Next, a specific synthesis example of the compound represented by the general formula (1) will be described.

Synthesis Example 1 Synthesis of 4-chloro-2-cyano-1-dimethylsulfamoyl-5-n-propylimidazole (Compound Hiro A-6b) (1) J, Org, Chew, 45.4038
4040 (1980), 2-formyl-1-diethoxymethylidazole was obtained as an oil from ■-diethoxymethylidazole. The imidazole-2-aldoxime obtained by the reaction is dehydrated with acetic anhydride to give 2-cyanoimidazole (melting point 176°).
C) was obtained.

[2] 30 g of 2-cyanoimidazole obtained in step (1), 53.4 g of anhydrous potassium carbonate, and 600 mj of acetonitrile were mixed at room temperature, reacted at reflux temperature for 2 hours, cooled, and dimethylsulfamoyl chloride 55
．． 6 g was added, and the reaction was again carried out at reflux temperature for 2 hours.

After the reaction was completed, the reaction product was poured into water, extracted with methylene chloride, washed with water, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography (developing solvent: methylene chloride) to obtain 28.0 g of 2-cyano-1-dimethylsulfamoylimidazole having a melting point of 74 to 76°C.

(3) Perform the above step [2] in a nitrogen atmosphere in a four-eye flask.
] 12.0 g of 2-cyano-1-dimethylsulfamoylimidazole and 240 g of dry tetrahydrofuran
a+j! Prepared with dry ice and acetone.
While keeping the temperature below ℃, add 41.3 ml of 1.6M n-butyllithium hexane solution (manufactured by Altorifti).
was gradually added dropwise. After the dropwise addition was completed, the temperature was maintained at the same temperature for 15 minutes, and then 30ml of a tetrahydrofuran solution containing 15.3g of n-propyl iodide was added dropwise at -70°C or below.

After the dropwise addition was completed, the mixture was gradually returned to room temperature in the stirring chamber to complete the reaction.

After the reaction was completed, the reaction mixture was poured into water, and 50% of ethyl acetate was added.
The ethyl acetate layer was washed with water and then dried over anhydrous sodium sulfate. After drying, ethyl acetate was distilled off, and the residue was purified and separated using silica gel column chromatography (developing solvent: methylene chloride) to obtain a solution with a melting point of 51-52.
2-cyano-1-dimethylsulfamoyl-5-n at °C
- 4.8 g of propylimidazole were obtained.

[4] 2-cyano-1 dimethylsulfamoyl-5-n-propyligodazole obtained in step [3] 4.8
g, 40 ml of pyridine and 11.4 ml of pyridinium chloride.
g was mixed and stirred at 90° C. for 4 hours to complete the reaction.

After the reaction was completed, pyridine was distilled off from the reaction mixture, extracted with ethyl acetate, washed with water, and then dried over anhydrous sodium sulfate. After drying, ethyl acetate was distilled off and the residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate).
2-cyano-4+5) -n-propylimidazole 2.4
6g was obtained.

(5) 2-cyano-4(5)- obtained in the above step [4]
2.35 g of n-propylimidazole, 80 nl of chloroform and 2.6 g of N-chlorosuccinimide were mixed and reacted under reflux for 4 hours.

After the reaction is complete, add 200 mJ of water to the reaction mixture! was added to separate the layers, further washed with water, and then dried over anhydrous sodium sulfate. After drying, chloroform was distilled off, and the residue was purified and separated using silica gel column chromatography (developing solvent: ethyl acetate/n-hexane = 1/1) to give 4(5)-chloro-2- with a melting point of 107-109°C. Cyano-5<41-2.28 of n-propylimidazole was obtained.

[6] 4(5)-chloro-2- obtained in the above step [5]
Cyano-5 (41-n-propylimidazole 2.0g
1 acetonitrile 30o+j, anhydrous potassium carbonate 1.9
5 g and dimethylsulfamoyl chloride 1.86
g was mixed, the temperature was slowly raised, and the reaction was completed by keeping at reflux temperature for 1 hour.

After the reaction is completed, acetonitrile is distilled off from the reaction mixture,
100 mm+ of water was added, extracted with 50 a+J of methylene chloride, washed with water, and then dried over anhydrous sodium sulfate. After drying, methylene chloride was distilled off, and the residue was analyzed after being left at room temperature overnight, and it was found that one of the two isomer mixture products decomposed and returned to the raw material. The remaining residue containing one isomer was purified and separated using silica gel column chromatography (developing solvent: methylene chloride) to obtain a melting point of 64~
1.1 g of the target product (compound A-6b) was obtained at 66°C.

Synthesis Example 2 Synthesis of 4-chloro-2-cyano-1-dimethylsulfamoyl-5-phenyligodazole (compound mA-1b) [l] 1.352 g of 2-cyano-4(5)-phenylimidazole was added to chloroform roomj+ dissolved in
1.175 g of N-chlorosuccinimide was added, and the mixture was reacted under heating under reflux for 4 hours.

After the reaction was completed, the reaction product was poured into water and extracted with chloroform. The extracted layer was washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (H opening solvent: methylene chloride) to give a solution with a melting point of 149-151''C4(5). -Chloro-2-cyano-5(4) - 1.28 g of phenylimidazole was obtained.

[2] 4(5)-chloro-2- obtained in the above step [1]
Cyano-5(4)-phenylimidazole 0.43 g
was dissolved in 6rn1 of acetone, and 0.2% of anhydrous potassium carbonate was added.
9g and dimethylsulfamoyl chloride 0.36
g was added thereto, and the mixture was reacted under heating under reflux for 30 minutes.

After the reaction was completed, the reaction product was poured into water and extracted with ethyl acetate. The extracted layer was washed with water, dried with anhydrous sodium sulfate,
After distilling off the solvent under reduced pressure, it was purified by silica gel column chromatography (developing solvent: methylene chloride) to a melting point of 10.
0.5 g of 4(5)-chloro-2-cyano-l-dimethylsulfamoyl-5+41-phenylimidazole at 6-109°C was obtained.

As a result of analysis by NMR spectroscopy, the above compound was found to contain approximately equal proportions of 4-chloro-2-cyanoagedimethylsulfupmoyl-5-phenyligodazole and 5-chloro-2-cyano-1-dimethylsulfamoyl. It was an isomer mixture with -4-phenylimidazole.

[3] After leaving 2.9 g of the isomer mixture obtained in the same manner as in step [2] above at room temperature for 24 hours, it was purified by silica gel column chromatography using methylene chloride as a developing solvent to obtain a mixture with a melting point of 109 to 112. 1.15 g of the target product (compound A-1b) was obtained.

Furthermore, 0.7 g of 4(5)-chloro-2-cyano-5(4)-phenyl-imidazole was also obtained through this purification and separation.

Synthesis example 34-chloro-5-(3-chloropropyl)-2
-cyano-1-dimethylsulfamoylimidazole (compound ll&LA-1,2b
) Synthesis of 2-cyano-4, 2-cyano-4,
9.4 g of 5-dichloro-1-dimethylsulfamoylimidazole and 152 mff1 of dry tetrahydrofuran
was charged, and 28.6 si of a 1.6M n-butyllithium hexane solution was gradually added dropwise while keeping the temperature below -75°C with dry ice-acetone. After finishing dropping 1
A solution of 14.3 g of l-chloro-3-iodopropane in 31 t of tetrahydrofuran was maintained at the same temperature for 5 minutes.
r+1 was added dropwise at -70°C or below. 1lQ after completion of dripping
The reaction was completed by gradually returning the temperature to room temperature while stirring.

After the reaction was completed, the reaction mixture was poured into water, extracted with methylene chloride, washed with water, and then dried over anhydrous sodium sulfate. Thereafter, methylene chloride was distilled off, and the residue was purified twice using silica gel column chromatography. 1lI (using methylene chloride as a developing solvent and once using n-hexane-ethyl acetate) to a melting point of 102~
Object at 105°C 4. ! , g was obtained.

The pest control agent of the present invention, which is a mixture of the compound represented by the general formula (1) and other specific compounds, is particularly useful as a fungicide for agriculture and horticulture, and is specifically used for rice blast disease. , rice blight, cucumber anthracnose, cucumber powdery mildew, cucumber rot, tomato late blight, tomato ring blight,
Citrus black spot, citrus green mold, pear @ star disease,
Apple leaf spot leaf disease, grape downy mildew, various gray mold diseases,
It exhibits excellent control effects against diseases such as sclerotium and rust, and against soil diseases caused by plant pathogens such as Fusarium, Bicillum, Rhizoctonia, Particillium, and Plasmodiophora. More specifically, diseases caused by algal fungi include late blight on potatoes and tomatoes, downy mildew on cucumbers and grapes, blue mold on tobacco, various soil diseases caused by Plasmodiophora spp., Aphanomyces spp., and Pythium spp. The pest control agent of the present invention not only has a long residual effect and has an excellent preventive effect, but also has an excellent therapeutic effect, making it possible to control the disease by post-infection treatment. It is.

In addition, since it has osmotic transferability, it is also possible to control diseases on stems and leaves by soil treatment.

The pest control agent of the present invention is further applied to insects, mites, and nematodes that are harmful to agriculture and horticulture, such as planthoppers, diamondback moths, leafhoppers, adzuki bean weevils, fall armyworms, green peach aphids, two-spotted spider mites, and red spider mites. ,
It shows excellent control effects against mites such as orange spider mite and nematodes such as sweet potato nematode.

The plurality of active ingredient compounds constituting the pest control agent of the present invention are mixed with various auxiliary agents as in the case of conventional pesticide formulations, and are formulated into emulsions, powders, wettable powders, liquids, granules, suspensions, etc. It can be formulated into various forms. At that time, the general formula (
The compound represented by 1) and another specific compound may be mixed and formulated in one boar, or they may be formulated separately and mixed. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. Examples of the auxiliary agents here include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrants, wetting agents, thickeners, stabilizers, and the like, which may be added as appropriate.

Carriers are divided into solid carriers and liquid carriers, and solid carriers include starch, sugar, cellulose, cyclodextrin, activated carbon, soybean), wheat), rice husk powder,
Animal and plant powders such as wood flour, fish meal, and powdered milk, talc, kaolin, bentonite, organic bentonite, calcium carbonate, calcium sulfate, sodium bicarbonate, zeolite, diatom, white carbon, clay, aluminum, silica,
Examples include mineral powders such as sulfur powder, and liquid carriers include water, animal and vegetable oils such as soybean oil and cottonseed oil, alcohols such as ethyl alcohol and ethylene glycol, ketones such as acetone and methyl ethyl ketone, dioxane, and tetrahydrofuran. ethers, kerosene,
Aliphatic hydrocarbons such as kerosene and liquid paraffin, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, and solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene, and acid amides such as dimethylformamide. Examples include esters such as ethyl acetate and glycerin ester of fatty acids, nitriles such as acetonitrile, sulfur-containing compounds such as dimethyl sulfoxide, and N-methylpyrrolidone.

In the pest control agent of the present invention, an appropriate mixing weight ratio of the compound represented by the general formula (1) and other specific mixing partner compound is generally 1:300 to 300;
, preferably 1:100 to 100:1, more preferably 1:50 to 5:1.

The usage concentration of the pest control agent of the present invention varies depending on the target crop, usage method, formulation form, application amount, etc., so it is difficult to specify -4, but in the case of foliage treatment, the active ingredient concentration is usually The compound represented by the general formula (1) is 1 to 1. OOOppm, other specific mixing partner compound is 1
~5. It is OOOppm. In case of soil treatment, t
f1 former is 10”IO, 000g/ha, latter is 10~
It is 50.000g/ba.

Below, some test examples will be described regarding the pest control agent of the present invention, for example, as a fungicide for agricultural and horticultural purposes, but the test examples are not limited to these.

Cultivate tomatoes (variety: Ponchi Rosa) in a polygon forest with a diameter of 7.5 cm. When they reach the 4-leaf stage, each test compound is added to the specified concentration! 1 orsl of the chemical solution prepared by Il was sprayed using a spray gun. After being kept in a thermostatic chamber at 22 to 24° C. for one day and night, a zoosporangial suspension of Phytophthora Phytophthora was inoculated by spraying.

Five days after inoculation, the lesion area was investigated and the control index was determined according to the following evaluation criteria, and the results shown in Tables 2-1 to 2-6 were obtained.

Note: The superiority delta quasi-controlling effect was determined by visual observation of the degree of disease onset of the test plants during the survey, and the control index was calculated using the following five levels.

[Control index] [Severity of disease onset] 5: No lesions observed 4: Lesion area is less than 10% of the untreated area 3: Lesion area is less than 40% of the untreated area 2: Lesion area but,
Less than 70% of the untreated area: The lesion area is 70% of the untreated area.
% or more Table 2-2 Tables 2-3 The same test as in Test Example 1 above was conducted. The test results were expressed according to the following evaluation criteria, and the results shown in Tables 3-1 to 3-3 were obtained.

The control effect of OyuΔken was determined by visual observation of the degree of disease onset of the test plants during the survey, and the control index was calculated using the following 7 levels.

[Control index] [Severity of disease onset] 7: No lesions are observed 6; The lesion area or length is less than 5% of the untreated area 5: The lesion area or length is less than that of the untreated area 5~10%
Less than 4: The lesion area or lesion length is 10 to 25 in the untreated area.
Less than 3%: The lesion area or lesion length is 25 to 40% of the untreated area.
Less than 2%; lesion area or lesion length is 40 to 70% of the untreated area
Less than %l: Lesion area or lesion length is 70% or more of the untreated area Table 2-5 Table 2 6 Table 3-1 Table 3-2 Table 3 3 Table 4-1 Diameter 7 Tomatoes (variety: Bonterosa) were grown in .5 cm plastic pots, and when they reached the four-leaf stage, they were spray inoculated with a zoospore suspension of Phytophthora blight. After 6 hours, chemical solution 10a+j containing each test compound at a predetermined concentration! Use a spray gun to fl! It was clothed. After being kept in a constant temperature room at 22 to 24°C for 5 days, the lesion area was investigated and the control index was determined according to the evaluation criteria of Test Example 2, and the results shown in Tables 4-1 to 4-3 were obtained.

Cucumbers (variety: Yotsuba) were grown in plastic pots with a diameter of 1.5 oa, and when they reached the two-leaf stage, they were spray inoculated with a spore suspension of downy mildew. After 24 hours, a chemical solution 10o+1 containing each test compound at a predetermined concentration was sprayed using a spray gun. After being kept in a constant temperature room at 22 to 24°C for 6 days, the lesion area on the first leaf was investigated, the control index was determined according to the evaluation criteria of Test Example 2, and the results in Tables 5-5-3 were obtained. Obtained.

■ Table 5-2 Table 5-3 Cultivate cucumbers (variety: four-leaf) in polyethylene pots with a diameter of 7.5 cm. When the two-leaf stage has been reached, each test compound is added to the specified concentration. The prepared chemical solution 10+++Il was sprayed using a spray gun. After keeping it in a constant temperature room at 22-24℃ for 1 day and night, a fungal disc (diameter 5
m) was inoculated. Three days after inoculation, the lesion length was investigated, and the control index was determined according to the evaluation criteria of Test Example 2, and the results shown in Table 6 were obtained.

Table 6 Diameter? Rice (variety: Chukyo Asahi) was grown in a 5c11 plastic pot, and when it reached the 5-leaf stage, chemical solution 20-1 containing each test compound at a predetermined concentration was sprayed using a spray gun. After being kept in a constant temperature room at 22 to 24° C. for one day and night, rice straw in which sheath blight bacteria had been cultured was sandwiched between the leaf sheaths and inoculated.

After being kept in an inoculation chamber at a temperature of 28° C. and a humidity of 100% for 5 days, the lesion length was investigated and the control index was determined according to the evaluation criteria of Test Example 2, and the results shown in Table 7 were obtained.

Table 7? = ' () Potato glucose agar medium (PD) containing 100 ppm streptomycin and each test compound at the specified concentration.
Pre-cultured cucumber cotton cancer fungi (for "μ ↓
A fungal disk (agar punched) of the anus was transplanted. After culturing at 22"C for 48 hours, the bacterial flora diameter was investigated, and the mycelial growth inhibition rate (%) was calculated using the following formula.
Obtained the results in the table.

Next, formulation examples of the pest control agent of the present invention will be described, but the formulation examples are not limited to these.

Formulation Example 1 (a) 5 parts by weight of compound A-1b (
(c) Compound D-345' (c) Kaolin 40 (d) Calcium ligninsulfonate 7 (v) Dialkyl sulfosuccinate 3 A wettable powder can be obtained by uniformly mixing the above components.

Formulation Example 2 In Formulation Example 1, (a) "5 parts by weight of compound NaA-1b" was replaced with "25 parts by weight of compound NllA-12b" and (b) "compound ff1D-345 parts by weight" was replaced. , a wettable powder can be obtained in the same manner except that "compound m!-1251! is replaced with parts".

Formulation Example 3 A hydrating powder is obtained in the same manner as in Formulation Example 1, except that the compound mK-IJ is substituted for the compound ktD-3J in (b).

Formulation Example 4 (a) Compound A-Lb 5 parts by weight (
b) Compound mG-115 (c) Calcium carbonate 20 (d) Kaolin 52 (e) Calcium lignin sulfonate 4 (f) Polyoxyethylene alkylaryl ether 4
Wettable powders can be obtained by uniformly mixing # and above.

Formulation Example 5 A hydrating powder is obtained in the same manner as in Formulation Example 4 (b) except that "Compound mG-IJ" is replaced with "Compound 11hF-IJ."

Formulation Example 6 A wettable powder is obtained in the same manner as in Formulation Example 4 (b) except that "compound ff1G-1j" is replaced with "compound 1'hO-IJ."

Formulation Example 7 (a) Compound A-6b 5 parts by weight (
(b) Compound magnetodynamic B-35 (c) Diatom ± 84 parts by weight (di) dialkyl sulfosuccinate 2 (e) polyoxyethylene alkylphenyl ether sulfate
4. Wettable powders can be obtained by uniformly mixing the above ingredients.

Formulation Example 8 A hydrating powder can be obtained in the same manner as in Formulation Example 7 (b) except that "compound NaB-3J" is replaced with "compound mM-IJ."

Formulation Example 9 (a) Kaolin 78 parts by weight (b) β-naphthalenesulfonic acid soda formalin condensate
2 (c) Polyoxyethylene alkylaryl sulfate 5
(d) Hydrous amorphous silicon dioxide 15 A mixture of each of the above components, 1 kA-1b of the compound, and 1 ml of the compound
-1 in a weight ratio of 8:1:1 to obtain a wettable powder.

Formulation Example 10 A wettable powder is obtained in the same manner as in Formulation Example 9 (b) except that "Compound 1m1-IJ" is replaced with "Compound 1kl-7J."

Formulation Example 11 (a) Compound Magnetism A-12b O, 25 parts by weight (b) Compound A-1-1 0.25 (c) Calcium carbonate 99.0 (d)
By uniformly mixing 0.5 or more lower alcohol phosphate esters, the agent can be obtained.

Formulation Example 12 (a) Compound @A-6b 2.5 parts by weight (b) Compound 1kl-12,5" (c) Xylene 75 (d) Polyoxyethylene alkylaryl ether
An emulsion is obtained by mixing and dissolving 20 or more components.

Formulation Example 13 (a) Compound NnA-1b O, 5 parts by weight (b) Compound 11m1-1 0.5"
(3) Bentonite 20 parts by weight (2) Kaolin 74 (e) Sodium ligninsulfonate 5 Add an appropriate amount of water required for granulation to each of the above ingredients, mix and granulate to obtain granules.

Formulation Example 14 (a) Compound N [LA-1b 2.5 parts by weight (b) Compound base D-322,5 (c) Kerosene 63 (d) Polyoxyethylene phenylphenol derivative and polyoxyethylene sorbicunal chelate mixture
A suspension agent is obtained by mixing each of the 12 or more components and pulverizing the mixture.

Formulation Example 15 "Compound 1thD-3J" in (b) of Formulation Example 14 is
A suspension is obtained in the same manner except that compound NIE-2J is used.

Claims (1)

[Claims] General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R^1 is a phenyl group or a halogen atom which may be substituted with a halogen atom. an alkyl group that may be substituted, and R^2 is a halogen atom), an azole compound, a quinoxaline compound, a dithiocarbamate compound, an organic chlorine compound, and a benzimidazole. -based compounds, pyridinamine-based compounds, cyanoacetamide-based compounds, phenylamide-based compounds, sulfenic acid-based compounds, copper-based compounds, isoxazole-based compounds, organophosphorus-based compounds, N-halogenothioalkyl-based compounds, dicarboximide-based compounds, benzanilides -based compounds, benzamide-based compounds, piperazine-based compounds, pyridine-based compounds, pyrimidine-based compounds, piperidine-based compounds, morpholine-based compounds, organotin-based compounds, urea-based compounds, cinnamic acid-based compounds, carbamate-based compounds, pyrethroid-based compounds, A harmful substance characterized by containing as an active ingredient at least one of a benzoyl urea compound, a thiazolidine compound, a thiadiazine compound, a neraistoxin derivative, a pyridazinone compound, or a live spore and produced crystal toxin of Bacillus thuringiensis. Biological control agents.