JPH0211588B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [In the formula, X is the same or different and represents a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a phenoxy group, a phenyl group, a cyano group, or a nitro group, n means an integer of 0 to 5, and R is an alkyl means an alkyl group substituted with a group, a cyclopropyl group, or an alkylsulfenyl group. However, R represents a tertiary butyl group, X represents a halogen atom or a phenyl group, and n
except when represents 1 or 2. ] Among the two geometric isomers of the ketone compound represented by [] [In the formula, X, n and R have the same meanings as shown above. ] The present invention relates to one of the geometric isomer compounds represented by the formula (1) or a salt thereof, a method for producing the compound, and a disinfectant and herbicide for agricultural and horticultural use containing the compound as an active ingredient. To give preferable examples of X, n and R in the compound of the present invention [], group, a straight chain or branched alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a halo-substituted alkyl group such as a trifluoromethyl group, a phenoxy group, a cyano group or a nitro group. n is particularly preferably 0, 1 or 2, and R is a linear alkyl group such as a methyl group, ethyl group, propyl group or butyl group, or a branched chain such as an isopropyl group, t-butyl group or sec-butyl group. Preferred are alkyl groups substituted with a cyclopropyl group or an alkylsulfenyl group (for example, a 2-methylsulfenylpropan-2-yl group). Many synthetic organic compounds with antibacterial properties have been discovered and developed as agricultural fungicides, protecting agricultural and horticultural crops from pathogenic bacteria and making a significant contribution to the stable supply of agricultural products. However, it is also true that there are many problems that need to be improved, such as environmental pollution and economic efficiency. One way to solve these problems is to use compounds that have higher bactericidal activity against plant pathogens, and to use compounds that have bactericidal activity against a broader range of pathogens to reduce disease control. The aim is to simultaneously control the pests.
The present inventors have discovered that an azole compound represented by the following general formula [] has excellent properties as a bactericidal agent (Japanese Patent Application Laid-open No. 41875/1983). [Wherein, X represents an alkyl group, a cyano group, an alkoxy group, a phenoxy group, a phenyl group, a halogen atom or a hydrogen atom, and m represents an integer of 1 to 5. R ₁ is

Imidazolyl group represented by [Formula] or Taha

Represents a triazolyl group represented by [Formula]. R ₂ represents a t-butyl group or a phenyl group that is unsubstituted or optionally substituted with an alkyl group, an alkoxy group, a phenyl group, or a halogen atom. ] However, as a result of further research from the above standpoint, it was found that among the geometric isomers of the triazole compound represented by the general formula It was discovered that it has excellent properties as an agricultural and horticultural fungicide, such as exhibiting activity, and this led to the completion of the present invention. That is, the triazole compound represented by the general formula [] has the general formula []
Geometric isomers indicated by and [ ] exist. [In the formula, X, n and R have the same meanings as shown above. ] When these isomers were isolated in pure form and their properties as fungicides, plant growth regulators, and herbicides were compared in detail, it was found that one isomer had far superior performance compared to the other. It has been found. These isomers can be identified, for example, by differences in their melting points, by NMR spectroscopy or by gas chromatography.
It can be characterized more clearly in the ketone compound that is the raw material for its production. In other words, a ketone compound represented by the general formula [] is a geometric isomer (hereinafter referred to as [-
Geometric isomers (hereinafter referred to as [-E] isomers) of triazole compounds represented by general formula [] obtained by reducing E] isomer), and geometric isomers represented by general formula [] with ketone compounds
In the NMR spectrum, the olefin proton appears on the lower magnetic field side (hereinafter referred to as [−
Comparing the bactericidal activity of the geometric isomers (hereinafter referred to as [-z] isomers) of triazole compounds represented by the general formula [] obtained by reducing the [-z] isomers), the following test examples showed that As shown, the former [-E] isomer exhibited far superior properties to the [-z] isomer. Target diseases for which the compound of the present invention exhibits excellent control effects include rice blast, strangle blight, apple rot, monilia disease, powdery mildew, scab, black spot and leaf spot, and pear black spot. Diseases, powdery mildew, red rot and scab, black spot of mandarin orange, scab, black pox, green and blue mold, botrytis of peach, late rot of grapes, botrytis, powdery mildew diseases and rusts, crown rust of oat, powdery mildew of barley, cloud blight, patchy leaf blight, bare smut, hard smut, snow rot sclerotium and black rust, rust of wheat, bare smut , smut, leaf blight, powdery mildew, yellow rust, black rust, powdery mildew, powdery mildew of cucurbits, gray mold, vine blight, sclerotinia and tuberculosis, tomato. Leaf mold, powdery mildew and rotary mildew, botrytis, hemi-wilt and powdery mildew of eggplant, powdery mildew of green pepper, botrytis and powdery mildew of strawberry, red starch and powdery mildew of tobacco , brown spot disease of sugar beet, black astringency disease and brown spot disease of Japanese sugar beet. Furthermore, further studies on the antibacterial properties of the compounds of the present invention revealed that the compounds of the present invention also exhibit antibacterial properties against Trichophyton rubrum. The possibility of Furthermore, the compound of the present invention can also be used as a plant growth regulator, and is applied to useful plants to suppress their growth. For example, it can be used to prevent the growth of rice, lawns, hedge trees, fruit trees, etc., or to prevent the growth of garden crops such as potted chrysanthemums. In rice cultivation, lodging of rice plants caused by excessive application of fertilizers and strong winds is often a serious problem. By applying this compound at the appropriate time, the height of rice plants can be moderately controlled, the length can be reduced, and lodging can be prevented. It is effective in preventing In the cultivation of potted chrysanthemums, application of this compound does not affect the flowers, and by shortening the length of the stems, the commercial value can be increased. Furthermore, the compound of the present invention has a herbicidal effect, and has a herbicidal effect on barnyard grass,
Upland weeds of the Poaceae family, such as grasshopper and foxtail grass,
Cyperus japonica, cyperus japonica, purslane, purslane,
It has a strong effect on broad-leaved field weeds such as chickweed, as well as annual and perennial weeds in paddy fields such as Japanese grasshopper, Japanese grasshopper, Japanese grasshopper, Japanese aphrodisiac, bulrush, and silver grass. When the compound of the present invention is used in upland fields, it is highly effective against major weeds in upland fields, and is effective both in soil treatment before weed emergence and in foliage treatment at the early stage of growth. It has excellent properties such as being harmless to major crops such as , sunflowers, and beets, and can be safely used on vegetables such as lettuce, radish, and tomatoes. Furthermore, when the compound of the present invention is used in paddy fields, it has strong activity against major weeds in paddy fields when treated before weed germination or during the early growing season, and at the same time is highly safe against rice. The compounds of the present invention are useful as herbicides not only for paddy rice but also for various grains, vegetables, orchards, lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forest gardens, non-agricultural lands, and the like. On the other hand, it has also become clear that the compound of the present invention has high safety for humans, livestock, and fish, and can be used without causing any harm to agriculturally useful crops. More specific methods for producing the compounds of the present invention include, for example, the methods described below. [In the formula, X, n and R have the same meanings as described above. ] That is, the [-E] isomer is reduced using a metal hydride complex such as lithium aluminum hydride or sodium borohydride in a suitable solvent or using an aluminum alkoxide such as aluminum isopropoxide. The [-E] isomer is produced by The [-E] isomer to be subjected to reduction can be obtained, for example, by fractional crystallization or column chromatography of the geometric isomer mixture of the ketone compound [] obtained according to the reaction formula below. but,
Furthermore, a mixture of the above-mentioned isomers can be irradiated with ultraviolet rays to carry out a photoisomerization reaction to obtain a higher yield. [In the formula, X, n and R represent the same meanings as shown above. ] Solvents used when a metal hydride complex is used in the reduction reaction are ethers such as diethyl ether and tetrahydrofuran, and alcohols such as methanol, ethanol, and isopropanol.
When using sodium borohydride as a metal hydride complex, for 1 mole of [-E] isomer
The reaction is accomplished by mixing 0.25 to 2 moles of sodium borohydride in the solvent. The reaction temperature is preferably in the range from 0° C. to room temperature, and the solvents used are ethers such as diethyl ether and tetrahydrofuran, and alcohols such as methanol, ethanol, and isopropanol. When using lithium aluminum hydride as a metal hydride complex, by adding 0.25 to 0.3 times the molar amount of lithium aluminum hydride solution to the [-E] isomer dissolved in the same solvent as compared to the raw material dissolved in the same solvent. The reaction is achieved. Reaction temperature is -60℃~
The temperature range is preferably +70°C, and the solvent used is ethers such as diethyl ether and tetrahydrofuran. After the reaction is completed, water or a dilute acid aqueous solution is added to the reaction solution, and if necessary, after neutralization with an alkali, the resulting crystals are collected or extracted with an organic solvent that is sparingly soluble in water. The subsequent processing is carried out according to conventional methods. When aluminum isopropoxide is used as a reducing agent, it is preferable to use an alcohol such as isopropanol or an aromatic hydrocarbon such as benzene as a solvent. The reaction is [
-E] Use 1 to 2 mol of aluminum isopropoxide per 1 mol of isomer, and
It is usually carried out at a temperature of °C. The resulting aluminum compound is decomposed with dilute sulfuric acid or an aqueous sodium hydroxide solution, and then extracted with an organic solvent that is sparingly soluble in water. The subsequent processing follows the usual method. The salt of the [-E] isomer is an acid that is physiologically acceptable to plants, such as hydrohalic acids such as hydrobromic acid, hydrochloric acid, and hydroiodic acid, acetic acid, trichloroacetic acid,
Salts with carboxylic acids such as maleic acid and succinic acid, sulfonic acids such as p-toluenesulfonic acid and methanesulfonic acid, nitric acid, sulfuric acid, and phosphoric acid.
If necessary, salts of these compounds of the present invention can be obtained by conventional methods. When the compound of the present invention obtained in this way is actually applied, it can be used without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a bactericidal, herbicidal, and plant growth regulator. It can be used in any of the commonly used forms, such as powders, wettable powders, oils, emulsions, tablets, granules, fine granules, aerosols, and floasols. The formulations generally contain from 0.1 to 95.0% by weight of active compound (including mixed ingredients), preferably
Contains 0.2-90.0%, usually 2-500 per 10 ares
An application amount of 1.5 g is appropriate. Furthermore, the concentration used is
A range of 0.001% to 1.0% is desirable, but since the amount and concentration used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., it is not possible to increase or decrease without being limited to the above range. There is no problem. Furthermore, it can be used in admixture with other fungicidal, herbicidal and plant growth regulators, such as N-(3,
5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, s-
Normal-butyl s-paratertiary butyl benzyl dithiocarbonimidate, 0,0-dimethyl 0-(2,6-dichloro-4-methylphenyl) phosphorothioate, methyl 1-butylcarbamoyl-1H-benzimidazol-2-ylcarbamate , 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 ethylene bisdithiocarbamate, bis(N,N-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,
Bactericidal agents such as 2-bis(3-methoxycarbonyl-2-thioureido)benzene, methyl N-(2,6-dimethylphenyl)-N-methoxyacetyl-2-methylglycinate, aluminum ethyl phosphite, 2, 4-dichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid, 2
- Phenoxy herbicides such as methyl-4-chlorophenoxybutyric acid, 2-methyl-4-chlorophenoxyacetic acid (including esters and salts), 2,4-dichlorophenyl 4'-nitrophenyl ether, 2,
4,6-Trichlorophenyl 4'-nitrophenyl ether, 2-chloro-4-trifluoromethylphenyl 3'-ethoxy-4'-nitrophenyl ether, 2,4-dichlorophenyl 4'-nitro-
Diphenyl ether herbicides such as 3'-methoxyphenyl ether, 2,4-dichlorophenyl 3'-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-4,6-bisethylamino-
1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5
-triazine, 2-methylthio-4,6-bisethylamino-1,3,5-triazine, 2-methylthio-4,6-bisisopropylamino-1,
Triazine herbicides such as 3,5-triazine, 3
-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1
-methoxy-1-methylurea, 1-(α,α-
dimethylbenzyl)-3-p-tolylurea, 1
-(2-benzylthiazolyl)-1,3-dimethylurea and other urea herbicides, isopropyl N-(3
-Chlorphenyl carbamate, methyl N-(3,
Carbamate herbicides such as 4-dichlorophenyl)carbamate, S-(4-chlorobenzyl)N,
Thiol carbamate herbicides such as N-diethylthiol carbamate, S-ethyl N,N-hexamethylenethiol carbamate, 3,4-dichloropropionanilide, 2-chloro-N-methoxymethyl-2',6'- Diethylacetanilide, 2
-chloro-2',6'-diethyl-N-(butoxymethyl)-acetanilide, 2-chloro-2',6'-
Diethyl-N-(n-propoxyethyl)acetanilide, N-chloroacetyl-N-(2,6-
Acid anilide herbicides such as (diethyl phenyl) glycine ethyl ester, uracil herbicides such as 5-bromo-3-sec-butyl-6-methyluracil, 3-cyclohexyl-5,6-trimethyleneuracil, 1,1 Pyridinium salt herbicides such as '-dimethyl-4,4'-bipyridinium chloride, N-(phosphonomethyl)glycine, N,N-
Bis(phosphonomethyl)glycine, 0-ethyl 0
-(2-nitro-5-methylphenyl)N-secondary-butylphosphoroamidothioate, S-
(2-methyl-1-piperidylcarbonylmethyl)
0,0-di-n-propyldithiophosphate,
Phosphorus herbicides such as S-(2-methyl-1-piperidylcarbonylmethyl)0,0-diphenyldithiophosphate, α,α,α-trifluoro-
Toluidine herbicides such as 2,6-dinitro-N,N-dipropyl-p-toluidine, 5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4 -Oxadiazolin-2-one, 3-isopropyl-(1H)-
2,1,3-Benzothiadiazin-(3H)-one-2,2-dioxide, α-(β-naphthoxy)
Propionanilide, 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole-5
-yl p-toluenesulfonate, 3-(methoxycarbonylamino)phenyl 3-methylphenyl carbamate, 4-amino-3-methyl-6-
It can be used in combination with phenyl-1,2,4-triazine, etc., and neither of them will reduce the pest control effect of each agent alone. This compound can also be used in combination with an insecticide, for example 0,0-dimethyl
-(4-nitro-3-methylphenyl)phosphorothioate, 0-(4-cyanophenyl)0,0
-dimethylphosphorothioate, 0-(4-cyanophenyl)0-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)
Organophosphorus insecticides such as phosphorodithioates, α
-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate,
It can be used in combination with pyrethroid insecticides such as α-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate, and both It does not reduce the control effect of the agent. Therefore, it is possible to control two or more types of pests at the same time, and a synergistic effect is also expected by mixing them. The compound according to the present invention is one of two types of geometric isomers of the compound represented by the general formula Of course, it also includes optical isomers. Next, the present invention will be explained in more detail with reference to Examples. Unless otherwise specified, NMR spectra are expressed in δ values using deuterated chloroform as a solvent and tetramethylsilane as an internal standard. Example 1-(4-methylphenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)
-Synthesis of [-E] isomer of 1-penten-3-ol (Compound No. 4) 1- Characterized by the following NMR spectrum
(4-methylphenyl)-4,4-dimethyl-2
[-E] isomer of (1,2,4-triazol-1-yl)-1-penten-3-one (melting point 87~
88°C) (2.7 g (0.01 mol)) was dissolved in 50 ml of methanol. This was cooled with ice and 0.38 g (0.01 mol) of sodium borohydride was added while keeping the reaction liquid temperature below 20°C. After keeping it at 20℃ for 3 hours, add 100ml of water.
Add 1 ml of acetic acid to decompose, and dissolve the organic layer in ethyl acetate.
Extracted with 100ml. After washing with 50 ml of 5% sodium bicarbonate solution, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from n-hexane to give a melting point of 155.
1.9 g (70% yield) of the [-E] isomer was obtained at ~157°C. 1-(4-methylphenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-
[-E] isomer of 1-penten-3-one
The NMR spectrum is shown. 8.30 (1H, singlet, triazole proton) 8.07 (1H, singlet, triazole proton) 7.20 (4H, singlet, phenyl proton) 7.15 (1H, singlet, olefin proton) 2.36 (3H, singlet, methyl proton) 1.02 (9H, Singlet, butyl proton) Reference example 1-(4-methylphenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)
-Synthesis of [-Z] isomer of 1-penten-3-ol (comparative compound) 1- characterized by the following NMR spectrum
(4-methylphenyl)-4,4-dimethyl-2-
[-Z] isomer of (1,2,4-triazol-1-yl)-1-penten-3-one (n ²² _D
1.5607) 2.7 g (0.01 mol) was dissolved in 50 ml of methanol. After reacting with sodium borohydride in the same manner as in Example 1, the same treatment was performed, and the residue was recrystallized from a mixture of carbon tetrachloride and n-hexane (1:10) to give 2.1 g (yield 78%). Compare and contrast ([−
Z]isomer) A melting point of 127-128°C was obtained. 1-(4-methylphenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-
[-Z] isomer of 1-penten-3-one
The NMR spectrum is shown. 8.13 (1H, singlet, triazole proton) 7.95 (1H, singlet, triazole proton) 7.56 (1H, singlet, olefin proton) 7.05 (2H, doublet, phenyl proton, J
=9Hz) 6.65 (2H, doublet, phenyl proton, J
=9Hz) 2.30 (3H, singlet, methyl proton) 1.22 (9H, singlet, butyl proton) Next, Table 1 shows examples of the [-E] isomer produced by the method of the present invention. For comparison [-
Z] The results of the NMR spectrum of the isomer are also described.

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[Table] Next, test examples and formulation examples will be described to further clarify the usefulness of the compound of the present invention as an agricultural and horticultural fungicide. Test example 1 Bacterial growth inhibition effect: 5g of polypeptone per 1 liter of water, malt extract
A medium containing 20 g of sucrose, 20 g of sucrose, and 20 g of agar was dissolved by heating, and a predetermined amount of a water diluted solution of the test compound in the form of an emulsion was added thereto to adjust the concentration of the test compound in the medium to a predetermined concentration. Subsequently, the medium was thoroughly stirred and then poured into a Petri dish to form an agar plate. After the agar had solidified, a bacterial flora disk or conidial suspension of the test bacteria was inoculated. The names of the test bacteria and the culture period from inoculation to observation are as follows. The culture temperature was 20°C for apple scab and 28°C for other bacteria.

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[Table] As shown in Table 2, the results for the compounds of the present invention [
The -E] isomer was found to exhibit a significantly broader antibacterial spectrum than the respective [-Z] isomer.

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[Table] Test Example 2 Controlling effect on rat snail brown spot A 150 ml plastic pot was filled with sandy soil, and one seed of rat snail (variety: semi-erect) was sown per pot. This is done in an air-conditioned greenhouse at 25-30℃.
After cultivating for 12 days, seedlings of Lamium chinensis with the third true leaf developed were obtained. A water diluted solution of the test compound in the form of an emulsion was sprayed onto the seedlings at 10 ml per pot. After the chemical solution was air-dried, the seedlings were inoculated with Cercospora arachidicola, and the plants were covered with vinyl to maintain humidity and placed in an air-conditioned temperature range of 25 to 30°C. After cultivating the above seedlings for another 10 days in an air-conditioned greenhouse to obtain sufficient disease onset,
The diseased state of the leaves was observed. After the onset of illness, it was calculated by the following method. That is, they are classified into indices of 0, 0.5, 1, 2, and 4 according to the degree of appearance of lesions on the investigated leaves.
The disease severity was calculated using the following formula. (Infection index) (Infection status) 0...No bacterial flora or lesions observed on the leaf surface. 0.5: Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area. 1...Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area. 2...Bacterial flora or lesions are observed on less than 50% of the leaf area. 4...Bacterial flora or lesions are observed on 50% or more of the leaf area. Disease severity (%) = Σ (sickness index) × (number of leaves) / (number of investigated leaves) × 4 ×
100 Next, the control value was calculated using the following formula. Control value (%) = 100 (incidence in compound treated area) / (incidence in non-treated area) x 100 As a result, as shown in Table 3,
-E] isomer showed a much higher control effect than each [-Z] isomer.

[Table] Test Example 3 Wheat rust control effect (therapeutic effect) (seedling test) A 150 ml plastic pot was filled with sandy soil, and 10 to 15 wheat seeds (variety: Norin No. 61) were sown. This was cultivated in an air-conditioned greenhouse at 18 to 23°C for 7 days to obtain wheat seedlings with the first true leaves developed. This young seedling is infected with wheat rust fungus (Pucciniarecondita).
was inoculated and placed in a humid room at 23°C for 16 hours to infect the bacteria. Subsequently, 10 ml of a water diluted solution of the test compound in emulsion form was sprayed per pot. After putting this in a constant temperature room at 23℃ and cultivating it under fluorescent light illumination for 10 days,
The disease state of the first true leaves was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 2. As a result, as shown in Table 4, the compounds of the present invention [
The -E] isomer exhibits a clearly higher pesticidal effect than the respective [-Z] isomers, and is also a commercially available fungicide and a compound described in JP-A-53-28170 that is chemically structurally similar to the compound of the present invention. It showed a clearly higher pesticidal effect compared to

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[Table] Test Example 4 Wheat black rust control effect (therapeutic effect) (seedling test) Wheat seedlings (variety: Norin No. 61) were obtained in the same manner as in Test Example 3. These young seedlings were inoculated with the wheat rust fungus (Puccinia graminis) and placed in a humid room at 23°C for 16 hours to infect them with the fungus. Next, add 10 ml of a water diluted solution of the test compound in emulsion form per pot.
Spread. This was placed in an air-conditioned greenhouse adjusted to 23°C, and after cultivation for 10 days, the disease state of the first true leaves was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 2. As a result, as shown in Table 5, the compound of the present invention [-
The E] isomer exhibits clearly higher control effects than the respective [-Z] isomers, and is also effective against commercially available fungicides and the compound described in JP-A-53-28170, which is chemically similar to the compound of the present invention. It clearly showed a high pest control effect.

[Table] Test example 5 Field weed control test 1/5,000th Earl Wagner pot with crabgrass,
Pack a clay pot with seeds of each of Aobiyu and Shiroza, make a predetermined amount of the original into an emulsion, dilute it with water,
The soil surface was treated using a hand sprayer. After the treatment, the five-leaf sugar beet seedlings (variety Monohill) grown in paper pots were transplanted to Wagner pots. Thereafter, the plants were grown in a greenhouse, and 20 days after treatment, the herbicidal efficacy and crop damage were observed. The results are shown in Table 6. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. However, phytotoxicity of crops is also shown using the same criteria as herbicidal efficacy. 0... Weed suppression rate 0-9% 1... 10-29 2... 30-49 3... 50-69 4... 70-89 5... 90-100

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[Table] Reference test example Pottomum (variety: Snow Ridge) was grown in a 4-inch unglazed pot filled with 500g of synthetic soil made of sea sand, mountain soil, and peat, and pinched two weeks after planting to produce three plants. Two weeks after the sprouts had grown, a diluted solution of the compound of the present invention at a predetermined concentration was applied, and the growth inhibitory effect was investigated on the 42nd day after the chemical treatment. The results are shown in Table 7. In addition, to evaluate the effect, measure the plant height of potumum plants in advance during the chemical treatment, calculate the length growth during this period from the difference with the plant height 42 days after treatment, and take the growth height of the untreated plot as 100. Expressed as elongation index. Values represent the average of triplicate. In addition, β-nine (N,N-
dimethylaminosuccinimizucacide) was used.

[Table] Formulation Example 1 Powder 2 parts of the [-E] isomer of Compound 1 of the present invention, 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder containing 2% of the main ingredient. Formulation Example 2 Powder 3 parts of the [-E] isomer of Compound 5 of the present invention, 67 parts of clay, and 30 parts of talc are thoroughly mixed to obtain a powder with a base ingredient content of 3%. Formulation example 3 Wettable powder: 30 parts of the [-E] isomer of the compound 2 of the present invention, 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of a wetting agent (sodium lauryl sulfate), and 2 parts of a dispersing agent (calcium lignin sulfonate). By thoroughly grinding and mixing, a hydrating agent with a base ingredient content of 30% can be obtained. Formulation example 4 Wettable powder 50 parts of the [-E] isomer of the present compound 10, 45 parts of diatomaceous earth, 2.5 parts of a wetting agent (calcium alkylbenzenesulfonate) and 2.5 parts of a dispersing agent (calcium ligninsulfonate) are thoroughly ground and mixed. A hydrating agent with a base agent content of 50% is obtained. Formulation Example 5 Emulsion 10 parts of the [-E] isomer of Compound 3 of the present invention, 80 parts of cyclohexanone, and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) are mixed to obtain an emulsion with a base agent content of 10%. Formulation Example 6 Granules 5 parts by weight of [-E] isomer of compound 15 of the present invention,
40 parts by weight of bentonite, 50 parts by weight of clay and 5 parts by weight of sodium ligninsulfonate are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules.

Claims (1)

[Claims] 1. General formula [In the formula, X is the same or different and represents a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a phenoxy group, a phenyl group, a cyano group, or a nitro group, n means an integer of 0 to 5, and R is an alkyl means an alkyl group substituted with a group, a cyclopropyl group, or an alkylsulfenyl group. However, R represents a tertiary butyl group, X represents a halogen atom or a phenyl group, and n
except when represents 1 or 2. ] Among the two geometric isomers of the ketone compound shown by, the general formula obtained by reducing the geometric isomer in which the olefin proton appears on the higher magnetic field side in the NMR spectrum (deuterated chloroform solution) [In the formula, X, n and R have the same meanings as described above. ] A geometric isomer compound or a salt thereof. 2 General formula [In the formula, X is the same or different and represents a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a phenoxy group, a phenyl group, a cyano group, or a nitro group, n means an integer of 0 to 5, and R is an alkyl means an alkyl group substituted with a group, a cyclopropyl group, or an alkylsulfenyl group. However, R represents a tertiary butyl group, X represents a halogen atom or a phenyl group, and n
except when represents 1 or 2. ] Among the two geometric isomers of the ketone compound represented by , the olefin proton appears on the higher magnetic field side in the NMR spectrum (deuterated chloroform solution), and the geometric isomer is reduced using a reducing agent. formula [In the formula, X, n and R have the same meanings as described above. ] A method for producing one of the geometric isomer compounds or a salt thereof. 3 General formula [In the formula, X is the same or different and represents a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a phenoxy group, a phenyl group, a cyano group, or a nitro group, n means an integer of 0 to 5, and R is an alkyl means an alkyl group substituted with a group, a cyclopropyl group, or an alkylsulfenyl group. However, R represents a tertiary butyl group, X represents a halogen atom or a phenyl group, and n
except when represents 1 or 2. ] Among the two geometric isomers of the ketone compound shown by, the general formula obtained by reducing the geometric isomer in which the olefin proton appears on the higher magnetic field side in the NMR spectrum (deuterated chloroform solution) [In the formula, X, n and R have the same meanings as shown above. ] An agricultural and horticultural fungicide characterized by containing one of the geometric isomers represented by the following or a salt thereof as an active ingredient. 4 General formula [In the formula, X is the same or different and represents a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a phenoxy group, a phenyl group, a cyano group, or a nitro group, n means an integer of 0 to 5, and R is an alkyl means an alkyl group substituted with a group, a cyclopropyl group, or an alkylsulfenyl group. However, R represents a tertiary butyl group, X represents a halogen atom or a phenyl group, and n
except when represents 1 or 2. ] Among the two geometric isomers of the ketone compound shown by, the general formula obtained by reducing the geometric isomer in which the olefin proton appears on the higher magnetic field side in the NMR spectrum (deuterated chloroform solution) [In the formula, X, n and R have the same meanings as shown above. ] A herbicide characterized by containing one of the geometric isomers represented by the following or a salt thereof as an active ingredient.