JPS6019751B2 - Benzylidene ketone compounds, their production methods, and fungicides comprising the compounds - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel benzylidene ketone compound represented by the following general formula (1), a method for producing the same, and a fungicide containing the compound as an active ingredient.

(In the formula, R represents an imidazolyl group or s-triazolyl group represented by or.

R2 represents a straight or branched alkyl group having 1 to 4 carbon atoms. X, Y and Z are the same or different, a straight chain or branched alkyl group having 1 to 4 carbon atoms, a hydrogen atom,
It represents a halogen atom, a nitro group, a cyano group, an acetoxy group, a trifluoromethyl group, a dimethylamino group, an alkoxy group represented by OR', or a phenoxy group. R' represents an alkyl group having 1 to 4 carbon atoms or a phenyl group which is unsubstituted or substituted with a halogen atom. ) Numerous organic synthetic compounds and antibiotics with antibacterial properties have been discovered and developed as agricultural fungicides to protect agricultural and horticultural crops from pathogenic bacteria and have greatly contributed to the stable supply of agricultural products.
In recent years, most diseases, except those caused by soil-borne diseases, bacteria, or viruses, can be controlled by spraying appropriate fungicides. However, in recent years, so-called drug resistance of plant pathogenic bacteria has become an important practical problem.

It has now been experienced that even if chemicals are sprayed in fields where drug-resistant bacteria have appeared, there is almost no control effect.
In addition, many reports have been made of the appearance of bacteria resistant to a large number of drugs. An appropriate method for preventing the emergence of such resistant bacteria is the alternate or mixed application of agents with different antibacterial action mechanisms against pathogenic bacteria.

Therefore, there is a need to develop agricultural fungicides that differ from conventional fungicides in terms of antibacterial action mechanism and have excellent disease control effects.

From the above viewpoint, we searched for new compounds that exhibit antibacterial properties, and found that the new benzylidene ketone compound represented by the general formula (1) is highly effective against diseases caused by fungi parasitic on agriculturally useful crops. In addition to having a strong pesticidal effect, these compounds also exhibit excellent antibacterial properties against so-called drug-resistant bacteria.On the other hand, these compounds are highly safe for humans, livestock, and fish, and are effective against agriculturally useful crops. It has been found that it has excellent properties as a pesticide in that it can be used without causing any harm in actual use. Target diseases for which the compound of the present invention exhibits excellent control effects include:
Blast and sheath blight of rice, monilia, powdery mildew, scab, black spot and spot blight of apple, black spot, powdery mildew, red spot and scab of pear, black V spot of mandarin orange , scab, black pox, green and blue mold, botrytis of peach, late rot of grapes, botrytis, powdery mildew and rust, crown rust of oat, powdery mildew of barley , naked smut, black rust and black rust of wheat, rust of wheat, rust of wheat, yellow rust, black rust and powdery mildew, powdery mildew of cucurbits, and botrytis , Sclerotinia and powdery mildew, Tomato* leaf mold, powdery mildew and ring spot, Botrytis and powdery mildew of eggplant, Powdery mildew of green pepper, Botrytis and powdery mildew of strawberry, Examples include tobacco blight and powdery mildew.

In addition, cucumber powdery mildew and grape grey, which are resistant to 1,2-bis(3-methoxycarbubonyl-2-thioureido)benzene and methyl-N-penzimidazol-2-yl-N-(butylcarbamoyl)carbamate, The compound of the present invention showed strong antibacterial properties against 0 fungal bacteria as well as against wild fungi (susceptible bacteria).
Further studies on the antibacterial properties of the compounds of the present invention revealed that some of the compounds of the present invention were inhibited by the Trich fungus.
It was revealed that the compound of the present invention also exhibits antibacterial properties against ophthalmogens and Candi albicans, which cause candida disease, and the possibility of use of the compound of the present invention as a medicinal antifungal agent was recognized.

The compound of the present invention can be produced by the method described below. (In the formula, R,, R2, X, Y and Z
has the same meaning as shown above.

) That is, by reacting 1 to 2 moles of penzaldehyde represented by the general formula (m) with 1 mole of the ketone represented by the general formula (0) in the presence of a base catalyst, the general formula (
A penzylidene ketone compound represented by 1) is produced.

Bases used as reaction catalysts include alkali metal or alkali metal hydroxides such as sodium hydroxide and calcium hydroxide, alkali metal alcoholates such as sodium methylate, sodium ethylate, and potassium methylate, and sodium carbonate. , carbonates such as potassium carbonate, secondary amines such as diethylamine, dipropylamine, pyrrolidine, piveridine, and morpholine with methanol,
0.5 in alcohols such as ethanol, aromatic hydrocarbons such as benzene, toluene, xylene, ethers such as diethyl ether, tetrahydrofuran, dioxane, water, and mixed solvents of these in the temperature range of 0 to 120°C. The target compound can be obtained by using ~10.0 mol. In addition, when using acetates such as sodium acetate and potassium acetate, carbonates such as sodium carbonate and potassium carbonate as bases, use glacial acetic acid or acetic anhydride as the reaction solvent and 0.5 to 10.0 mol of the base. It is also possible to carry out the reaction in a temperature range of 15 to 12,000 °C.

When actually applying the compound of the present invention obtained in this way, it can be used in pure form without adding any pond components, or it can be mixed with a carrier and applied to make it easier to use as a fungicide. It can be used in any of the commonly used forms, such as powders, wettable powders, oils, emulsions, tablets, granules, fine granules, and aerosols.

The active compounds (including natural ingredients) are generally present in the preparations.
0.1 to 95.0% by weight, preferably 0.2 to 95.0%
90.0%, and an application rate of 2 to 500 per 10 are is usually appropriate.

Further, the concentration used is preferably in the range of 0.001% to 1.0%, but the amount and concentration used vary depending on the formulation, application time, method, location, target disease, target crop, etc. There is no problem in increasing or decreasing the value regardless of the range. Furthermore, it can be used in combination with other fungicides, such as N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarpoximide, S-normal-butyl S -pt-butylbenzyldithiocarbonimidate, 0,0-dimethyl-2,6-dichloro-4-methylphenylphosphorothioate, methyl-N-benzimidazol-2-yl-N-(butylcarbamoyl)carbamate, N -trichloromethylthio-4-cyclohexene-1,2-dicarboximide, cis-N-(1,1,2,2-tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide, polyoxin, streptomycin, zinc Ethylene bisdithiocarbamate, zinc dimethylthiocarbamate, manganese ethylenepisdithiocarbamate, bis(dimethylthiocarbamoyl)disulfide, tetrachloroisophthalonitrile, 8-hydroxyquinoline, dodecylguanidine acetate, 5,
6-dihydro.

-2-Methyl-1,4-oxathiin-3-carboxanilide, N'-dichlorofluoromethylthio-N,N-dimethyl-N'-phenylsulfamide, 1-(4-chlorophenoxy)-3,3-dimethyl- 1-(1,2,
4-triazol-1-yl)-2-butanone, 1,2
-bis(3-methoxycarbonyl-2-thioureido)
It can be used in combination with benzene, etc., and neither will reduce the control effect of each agent alone. It can also be used in combination with insecticides. For example, 0,0-dimethyl○-(
4-nitro-tolyl) phosphorothioate, 0-p
-Cyanophenyl 0,0-dimethylphosphorothioate, 0-p-cyanophenyl○-ethylphenylphosphonothioate, 0,0-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate, 2-methoxy 4H-1,3 , 2-benzodioxaphosphorine-2-sulfide, 0,0-dimethyl S-(1-ethoxycarbonyl 1-phenylmethyl)phosphorodithioate, a-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-isovalerate, 3 -Phenoxybenzyl 2,
It can be used in combination with 2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate, 3-phenoxybenzylxansemate, etc., and neither of these will reduce the control effect of each single agent. do not have. Therefore, it is possible to control two or more types of pests at the same time, and a synergistic effect by mixing them is also expected.

The present invention will be explained in more detail below with reference to examples of the manufacturing method. Example 1 a-o-chlorobenzylidene-al-imidazolylpinacolone (compound number 1) o-al-imidazolylpinacolone 1.0 mol (0.006 mol), o-chlorobenzaldehyde 0.84 mol (0.00 mol). 006 moles), 10 volumes of acetic anhydride, and 0.4 moles of potassium carbonate (0.003 moles) were mixed and kept at 50°C for 3 hours.

The reaction solution was poured into 100 volumes of warm water (50 mm) to decompose acetic anhydride. Next, potassium carbonate was added until the liquid became alkaline, and the mixture was extracted with 100% of ethyl acetate. The ethyl acetate layer was washed with water and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain a brown oil of 1.1 hours. When this was purified by column chromatography using silica gel 50% and 0% (eluted with a mixed solvent of n-hexane and acetone 3:1), the yield was 0.69% (40%).
A-o-chlorobenzylidene-a-imidazolylpinacolone was obtained. Melting point Satoshi~8
Piota elemental analysis C (%) day (%) N (%) C so (%) Calculated value (as C, rainbow, 7N2C so0) 66.54 5.95 9.70 12.
27 Actual value 6650 5.95 9.81
12.320 Example 2a-2,4-dichlorobenzylidene-a-1-imidazolylacetone (Compound No. 7
)a-1-Imidazolylacetone 0.45 (0.00
36 mol), 2,4-dichlorobenzaldehyde 1.8
9 mol (0.01 female mol), potassium carbonate 1.49 mol (0
．． 01 female mol) and acetic anhydride low' were mixed and heated to 60°C.
heated for an hour.

The reaction solution was poured into 5,000 ml of warm water, and then potassium carbonate was added little by little to make it alkaline.

After extracting with 100% ethyl acetate and washing the ethyl acetate layer with water,
When 20% ice-cold hydrochloric acid was added to separate the layers, it was confirmed that 2,4-dichlorobenzaldehyde remained in the ethyl acetate layer. The aqueous hydrochloric acid layer was made alkaline with 5% aqueous sodium hydroxide under ice cooling, and extracted again with 50% ethyl acetate. After washing the ethyl acetate layer with water, it was dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure to give a solution of 0.13% (13%).
a-2,4-dichlorobenzylidene-a-11-imidazolylacetone was obtained. n crab. 5
1.6186 elemental analysis C (%) day (%) N (%) C
Poison%) Calculated value (as C. 3rd, Bu2C Evening 20) 55.53
359 9.97 2522 actual measurement value
55 muscles 3. Muscle 9. Total 258 examples 3
a-3,5-dichloro-2-acetoxybenzylidene-
a-1-imidazolylpinacolone (compound number 15) a
-2.0 moles of 1-imidazolylpinacolone (0.012 mol), 2.3 moles of 3,5-dichlorosalicylaldehyde (
0.012 mole), potassium carbonate 1.66 mole (0.01 mole), potassium carbonate 1.66 mole (0.01
2 mol) and 30% of acetic anhydride were mixed to 40q0. The insects were heated for a long time.

After decomposing acetic anhydride by slowly dropping 100 parts of 5,000 parts of water, 5% sodium hydroxide solution was added dropwise to neutralize the acetic acid while keeping the concentration below 20 parts.

The reaction solution was extracted with 100ml of ether, washed with 100ml of water, and the ether layer was dried over anhydrous sodium sulfate. The ether was distilled off under reduced pressure, and the remaining oil was chromatographed in the same manner as in Example I, and further recrystallized in carbon tetrachloride.
8%) of a-3,5-dichloro-2-acetoxybenzylidene-a-1-imigzolylpinacolone was obtained. During the reaction, the hydroxyl group was acetylated with acetic anhydride to introduce an acetoxyl group. melting point
129-131℃ Elemental analysis C (%) Days (%)
N (%) CZ (%) Calculated value (C, 8th, 8N2C evening 20
3) 56.70 4.77 7.35
18.60 Actual value 5643 4. Group 7. Plaque 1890 Example 4a-p Monoethoxybenzylidene-a-1-imigzolylpinacolone (Compound No. 8) a
-2.0 moles (0.012 mol) of 1-imidazolyl pinacolone, 1.8 moles (0.0 mol) of p-ethoxybenzaldehyde
12 mol), 5 parts of water and 5 parts of ethyl alcohol were mixed and cooled to 1 to 15°C in a water bath.

A solution of 0.6 parts caustic soda dissolved in 5 parts water was added to this mixture with stirring. After praying with candles for two hours at room temperature, I poured out the candles for four hours for six hours. The reaction solution was diluted with 100 ml of ether, washed with 100 ml of ice-cold water, and the ether layer was dried over anhydrous magnesium sulfate. After removing the ether under reduced pressure, the remaining oil was purified by silica gel chromatography in the same manner as in Example 1, and further recrystallized from a mixed solvent of carbon tetrachloride and n-hexane (1:1) to give 0.
25 (7.0%) of ap-ethoxybenzylidene
a-1-imidazolylpinacolone was obtained. melting point
120-121℃ elemental analysis C (%)
Day (%) N (%) Calculated value (as C, 8 days 22N202) 72.45 7.43 9.39 Actual value ? 2.29 7.41 9.
51 Example 5a-2,4-dichlorobenzylidene 1a
-1-s-triazolylpinacolone (compound number 21)
a-1 Triazolylpinacolone 2.0 t (0.012
mol), 2,4-dichlorobenzaldehyde 2.1 mole (mol), 2,4-dichlorobenzaldehyde (mol)
0.012 mole), potassium carbonate 1.66 mole (0.01 mole), potassium carbonate 1.66 mole (0.01
2 mol) and 30 cc of acetic anhydride were mixed and heated to 70 to 8 mol for 5 hours.

The reaction solution was poured into warm water at a temperature of 5.5 mm and then made alkaline by adding potassium carbonate.

Extraction was performed with 100 cc of ethyl acetate, and the ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the oily residue was purified by silica gel column chromatography (n-hexane:acetone = 10:1), and further recrystallized from carbon tetrachloride to obtain a-2,
1.0 (26%) of 4-dichlorobenzylidene-a-11s-triazolylpinacolone was obtained. melting point
119-120q0 elemental analysis C (%) day (%) N (%) C doku%) Calculated value (C, 5th, 5N3C evening 20) 55.57
4.66 12.96 21.87 Actual value
55.71 4.74 12. Iso 21.7
3 Example 6a-benzylidene-a-1-imidazolylpinacolone (Compound No. 27) a-1-imidazolylpinacolone 2.0 times (0.012 mol), benzaldehyde 1.3 times (0.012 mol), sodium acetate 2.0 times (0.012 mol). 0 evening (
0.024 mol) and 30 cc of acetic anhydride were mixed and heated for one hour at 60:00.

The reaction solution was poured into 50% warm water, and then potassium carbonate was added to make it alkaline.

After extraction with 100 cc of ethyl acetate and washing with water, the ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting crystalline clear product was recrystallized from carbon tetrachloride to obtain 1.4 kg (46%) of a-penzylidene-al-imidazolyl pinacolone. melting point
Total ~89q0 elemental analysis C (%) Day (%
) N (%) Calculated value (C, 6 days, 8N20) 75
．． 56 7.13 11.01 Actual value
75.55 7.21 11.09 Example 7
a-3,5-dichlorobenzylidene-a-1-imidazolylpinacolone (Compound No. 22) a-1-imidazolylpinacolon 2.0 mols (0.012 mol), 3,5-dichlorobenzaldehyde 2.1 mols (0. 012 moles),
2.0 ml (0.024 mol) of piberidine and 50 cc of absolute ethanol were mixed, and after being brought to room temperature for 1 hour at sea, the mixture was heated under reflux for 4 hours.

After cooling the reaction solution, it was diluted with 200 cc of ether, washed with water, and then dried over magnesium sulfate. The solvent was distilled off and the oily residue was purified by silica gel column chromatography (n-hexane:acetone = 10:1) to obtain a-3,5-dichlorobenzylidene-a-1-imidazolylpinacolone 0. .5 evenings (13%). melting point
81-820 Elemental analysis C (%) day (%) N (%) C evening (%) Calculated value (as C, 6th, 6N2C so20) 59.45
4.99 8.67 21.93 Actual value 59.42 4.87 8.67 21.94
Next, examples of compounds produced by the method of the present invention are shown in Table 1, but the present invention is not limited thereto.

The present invention will be explained in more detail by giving test examples and formulation examples below in Table 1, but the types and mixing ratios of additives to the compounds of the present invention are not limited to these and can be varied within a wide range.

Test Example 1 Test on the effect of controlling pear black spot disease Three-year-old pear seedlings (variety: 20th century) grown in twin clay pots with a diameter of 30 cm were used as test plants.

One seedling produces 3 to 4 new shoots, resulting in 10 to 10 new shoots.
When the 2q female was developed, an emulsion of the compound of the present invention was diluted with water and a chemical solution of a prescribed concentration was sprayed at a concentration of 30 cm per bottle.

After being cultivated in a greenhouse for 78 days after spraying, the conidia of pear black spot fungus (AI: rmariaKik hjaM) obtained by culturing on a vegetable juice agar medium for 10 days were suspended in water, and the entire seedlings were infected. Mist inoculation. After inoculation, the plants were kept in a greenhouse for 24 hours, and then kept in a greenhouse for 2 days, and then the severity of disease was investigated using disease indexes of 0.1, 2, 3, 4, and 5 as shown below. Disease state No index lesions observed 0 1 on leaf surface
Less than 0% lesions observed 1″ 10-20
Less than % of lesions are observed.

2〃20~40%''
3〃 40-60% 〃 4〃
5. The disease severity, which indicates 60% or more of lesions, was calculated based on the following formula. Disease severity ZG disease index) x (
Applicable number of leaves) XI. 〇Number of leaves tested in the room) x 5 As shown in Table 2, the compound of the present invention exhibited superior control effects compared to the control compound tested at the same time.

Table 3 Note (1) Commercially available bactericidal test example 2 Antibacterial test against drug-resistant bacteria Heat and dissolve 10M of potato decoction agar, add emulsion of the compound of the present invention and mix well. It was poured into a bird dish to make an agar plate.

After the agar had solidified, a drug-resistant Botrytis fungus (Botrytis sc.
inrea) or wild fungi (susceptible bacteria).
A disc (5 ribs in diameter) of P. scinerea was placed in the center of an agar plate and cultivated at 20°C for 3 days. After culturing,
The diameter of the grown fungi was measured and compared with the no-medicine-added plot, and the fungal growth inhibition rate was calculated using the following formula. Bacterial growth inhibition rate =・oo・(Medicine xiahan imitation wing horse district's bacterial growth inhibition rate) X・o.

As a result, the compound of the present invention showed drug-resistant B.
otrytis cinerea, sensitive shame t
It showed strong antibacterial properties as well as against A. and tiscinerea. Table 3 A. Wild fungus (susceptible fungus) Botrytis ci fertilizer
Effect on a Note (1) Commercially available fungicide, 1,2-bis(3
-methoxycarbonyl-2-thioureido)benzene Note (1) B. Drug-resistant bacteria Botrytiscinerea
Effect on Notes (1) 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene-resistant bacterial strains (isolated from grapes) Note (2) Commercially available fungicides,
1,2-bis(3-methoxycarbonyl-2-thioureido)benzene test example 3 Test on barley powdery mildew control effect Barley (variety: Goune Shiseki) was cultivated in a flower pot with a diameter of 9. When developed, the emulsion of the compound of the present invention was diluted with water to a predetermined concentration.

The chemical solution was sprayed at 15 times per pot. After air-drying the chemical solution, barley powdery mildew fungus (Erysiphegaminis)
) was inoculated and cultivated for 10 days in a temperature controlled room at 23°C under fluorescent lighting, and then the disease state was observed. The disease severity was calculated by the following method.

That is, depending on the lesion area of the investigated leaf, 0, 1" 2, 3, 4
, 5, the number of leaves corresponding to each disease index was investigated, and the disease severity was calculated using the following formula. Disease index
Disease state: 0 No lesions observed 1 Lesion area less than 10% 2
〃30% disease index
Disease state 3 Lesion area is 60% 4 〃80%
〃5 〃80% or more severity (%) = 20th trial number) X・〇.

The results of this test are shown in Table 4, and as is clear from the results, the compound of the present invention showed excellent control effects similar to the comparative control compound. Notes to Table 4 (1) Fungicide, 2,6-dimethyl-4-tridenlemorpholine Test Example 4 Test on oat crown rust control effect Oats (variety: Shingo) were cultivated in flowerpots with a diameter of 9. When the first leaf develops, the oat crown rust fungus (PiciniacMoMte)
) was inoculated and placed in a greenhouse for 8 hours.

Thereafter, an emulsion of the compound of the present invention was diluted with water to make a predetermined concentration, and a chemical solution was sprayed at 15 doses per pot, and the plants were placed in a constant temperature room at 23°C and cultivated under fluorescent lighting for 10 days, after which the disease state was observed. . The disease severity was calculated in the same manner as in Test Example 3. The results of this test are shown in Table 5, and as is clear from the results of this test, the compound of the present invention showed a superior control effect compared to the comparative compound.

Table 5 Table 5 Note (1) Fungicide, N,N-bis(1-formamide-2
,2,2-trichloroethyl)-piverazine formulation example 1
Powder compound [4] 2 parts, clay Isobe and talc 1
By thoroughly pulverizing and mixing the anchorage, a powder containing 2% of the main ingredient can be obtained.

Formulation Example 2 Powder 3 parts of compound (13), 6 parts of clay, and 30 parts of talc are thoroughly ground and mixed to obtain a powder with a base ingredient content of 3%.

Formulation example 3 Wettable powder compound ■ 3 base parts, diatom ± 3 anchor parts, white carbon 35
1 part, 3 parts of a wetting agent (sodium lauryl sulfate), and 2 parts of a dispersing agent (calcium lignin sulfonate) to obtain a wettable powder with a base ingredient content of 30%.

Formulation Example 4 Thoroughly pulverize and mix 5 parts of the hydrating agent compound (18), 45 parts of diatomite, 2.5 parts of a wetting agent (calcium alkylbenzenesulfonate), and 2.5 parts of a dispersant (calcium lignin sulfonate). A hydrating agent having a base agent content of 50% is obtained.

Formulation Example 5 Emulsion By mixing 3110 parts of the compound, 8 parts of xylene, and 1 part of the emulsifier (polyoxyethylene alkyl allyl ether), an emulsion with a base agent content of 10% is obtained.

Formulation example 6 Emulsion compound (19) 3 Togegun, xylene 6
By mixing the fat part and 1 part of an emulsifier (polyoxyethylene alkylarylene), an emulsion with a base agent content of 30% is obtained.

Claims (1)

[Claims] 1. Imidazolyl represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼) or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or s-triazolyl group. R_2 represents a straight chain or branched alkyl group having 1 to 4 carbon atoms. X, Y and Z are the same or different and represent a straight chain or branched alkyl group having 1 to 4 carbon atoms. group, hydrogen atom, halogen atom, nitro group, cyano group, acetoxy group,
It represents a trifluoromethyl group, a dimethylamino group, an alkoxy group represented by OR', or a phenoxy group. R'
represents an alkyl group having 1 to 4 carbon atoms or a phenyl group that is unsubstituted or substituted with a halogen atom. ) A benzylidene ketone compound represented by 2 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ R_2 represents a linear or branched alkyl group having 1 to 4 carbon atoms. are the same or different, a straight chain or branched alkyl group having 1 to 4 carbon atoms, a hydrogen atom,
It represents a halogen atom, a nitro group, a cyan group, an acetoxy group, a trifluoromethyl group, a dimethylamino group, an alkoxy group represented by OR', or a phenoxy group. R' represents an alkyl group having 1 to 4 carbon atoms or a phenyl group that is unsubstituted or substituted with a halogen atom. ) The general formula is characterized by reacting benzaldehydes represented by
has the same meaning as shown above. ) A method for producing a benzylidene ketone compound. 3 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Imidazolyl group or s-triazolyl group R_2 represents a straight chain or branched alkyl group having 1 to 4 carbon atoms. Atom, nitro group, cyano group, acetoxy group,
It represents a trifluoromethyl group, a dimethylamino group, an alkoxy group represented by OR', or a phenoxy group. R_1
represents an alkyl group having 1 to 4 carbon atoms or a phenyl group that is unsubstituted or substituted with a halogen atom. ) A bactericide characterized by containing a benzylidene ketone compound as an active ingredient.