JPH0115509B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [In the formula, X represents a halogen atom, and n represents 0, 1 or 2. ] A triazole compound or a salt thereof,
The present invention relates to a method for producing the same and an agricultural and horticultural disinfectant, weed killer, and plant growth regulator containing the same as an active ingredient. The compound of the present invention represented by the general formula [] has geometric isomers represented by the general formula [] and []. (In the formulas [] and [], X and n have the same meanings as shown above.) The present invention relates to both of the above two geometric isomers or mixtures thereof, as well as each optical isomer and their respective optical isomers. It covers mixtures. This 2
Two geometric isomers differ, for example, in their melting points,
It can be confirmed by NMR spectroscopy or gas chromatography, but can be more clearly characterized by the ketone compound from which it is manufactured. In other words, the general formula [] (wherein, One geometric isomer (hereinafter referred to as the [-E] isomer) of the triazole compound represented by the general formula [ ] obtained by reducing the [-E] isomer) and the general formula By reducing the geometric isomer of the ketone compound (hereinafter referred to as the [-Z] isomer) whose olefin proton appears in the lower magnetic field in the NMR spectrum (deuterated chloroform solvent) of the ketone compound shown by [] The other geometric isomer (hereinafter [
-Z] isomer), and the present invention deals with [-
E] isomer, [-Z] isomer, or a mixture of both. Furthermore, each geometric isomer has two types of optical isomers, and it goes without saying that the present invention extends to single optical isomers and mixtures thereof. 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 effects against plant pathogens, and to use compounds that have bactericidal activity against a broader range of pathogens to control diseases. The aim is to simultaneously control the pests.
The present inventors have previously 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). (In the formula, X represents an alkyl group, cyano group, alkoxy group, phenoxy group, phenyl group, halogen atom or hydrogen atom, and m represents an integer of 1 to ₅ .

Imidazole group represented by [Formula] or Taha

Represents a triazole 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, in this publication, R ₂ in the general formula [] is limited to a t-butyl group, a phenyl group, or a substituted phenyl group, and there is no mention of other alkyl groups, cycloalkyl groups, etc. 1-, a unique organic residue
The compound of the present invention, which is characterized by having a methylcyclopropyl group in its chemical structure, refers to a new group of compounds that are structurally completely different from the compounds described in the publication. As a result of further research from a new perspective, the present inventors found that the compound of the present invention represented by the general formula I discovered something. In addition, the present inventors isolated each of the two geometrical isomers of the triazole compound represented by the general formula [] and conducted a detailed comparative study of their properties as fungicides, and found that the [-E] isomer It was also discovered that the [-Z] isomer exhibits higher bactericidal activity against a wider range of plant pathogenic bacteria, leading to the completion of the present invention. That is, as is clear from Examples 3 and 4 below, both the [-Z] isomer and the [-E] isomer of the compound of the present invention exhibit excellent plant disease control effects, but as shown in Example 6. We found that the [-E] isomer exhibits higher fungicidal activity against a wider range of plant pathogens than the [-Z] isomer, and has superior properties as an agricultural and horticultural fungicide. Ta. Target diseases for which the compounds of the present invention exhibit excellent control effects include rice blast, sheath 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 powdery mildew, botrytis, hemi-wilt and powdery mildew of eggplant, powdery mildew of bell pepper, botrytis and powdery mildew of strawberry, red starch and powdery mildew of tobacco , brown spot disease of sugar beet, black astringent disease and brown spot disease of Japanese cabbage. Further studies on the antibacterial properties of the compounds of the present invention revealed that the compounds of the present invention
It was revealed that the compound of the present invention also exhibits antibacterial properties against Trichophyton rubrum, and the possibility of use of the compound of the present invention as a pharmaceutical antifungal agent was recognized. 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, wheat, lawns, hedge trees, fruit trees, etc., or to prevent the growth of horticultural 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 this compound is used in fields, it is highly effective against major weeds in fields, and it is also effective in soil treatments performed before weeds emerge, as well as in foliage treatments performed at the early stage of growth.
Furthermore, it has excellent properties such as being harmless to major crops such as rice, soybeans, cotton, corn, peanuts, sunflowers, and beets, and can be safely used on vegetables such as lettuce, radish, and tomatoes. Also, when using this compound in rice 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, side dishes, orchards, lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forests, 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 and n have the same meanings as shown above.) That is, the ketone compound represented by the general formula The compound of the present invention represented by the general formula [] is produced by reduction using a complex or using an aluminum alkoxide such as aluminum isopropoxide. If the [-E] isomer, which is one of the geometric isomers, is used as a ketone compound, one of the geometric isomers ([-E] isomer) of the compound of the present invention can be obtained by reducing it; The other geometric isomer ([-Z] isomer) of the compound of the present invention can be obtained from the other geometric isomer ([-Z] isomer) of the compound. The ketone compound [] to be subjected to reduction can be obtained, for example, according to the reaction formula below, but it can also be separated into two geometric isomers ([-E] isomer and [-Z] isomer) can be obtained in pure form. Furthermore, if a mixture of geometric isomers of the ketone compound [] is irradiated with, for example, a UV lamp or a xenon lamp to carry out a photoisomerization reaction, the [-E] isomer can be obtained in good yield. (In the formula, X and n have the same meanings as shown above.) Solvents used when using a metal hydride complex in the reduction reaction include ethers such as diethyl ether and tetrahydrofuran, methanol, ethanol, and isopropanol. Alcohols such as
When using sodium borohydride as a metal hydride complex, the amount per mole of ketone compound []
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 include ethers such as diethyl ether and tetrahydrofuran, methanol, ethanol,
Alcohols such as isopropanol. When using lithium aluminum hydride as a metal hydride complex, the ketone compound [] dissolved in a solvent has a concentration of 0.25 to 0.3 with respect to the raw material dissolved in the same solvent.
The reaction is accomplished by adding double molar lithium aluminum hydride solution. The reaction temperature is −60
The temperature range is preferably from .degree. C. to +70.degree. C., and the solvent used is ethers such as diethyl ether and tetrahydrofuran. After the reaction is complete, add water or dilute acid aqueous solution to the reaction solution, neutralize with alkali if necessary,
The resulting crystals are filtered 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 the reducing agent, it is preferable to use alcohols such as isopropanol or aromatic hydrocarbons such as benzene as the solvent. The reaction uses 1 to 2 mol of aluminum isopropoxide per 1 mol of ketone compound [], and the reaction starts from room temperature.
It is usually carried out at a temperature of 100°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. Salts of the compounds of the present invention can be prepared using physiologically acceptable acids, such as hydrohalic acids such as hydrobromic acid, hydrochloric acid, and hydroiodic acid, carboxylic acids such as acetic acid, trichloroacetic acid, maleic acid, and succinic acid, and p-toluene. These are salts with sulfonic acids such as sulfonic acid and methanesulfonic acid, nitric acid, sulfuric acid, phosphoric acid, and the like, and if necessary, these salts of the compounds of the present invention can be obtained by conventional methods. When actually applying the compounds of the present invention obtained in this way, they can be used in pure form without adding other ingredients, or they can be mixed with carriers to facilitate use as fungicidal, herbicidal, and plant growth regulators. It can be applied in any of the commonly used forms, such as powders, wettable powders, oils, emulsions, tablets, granules, fine granules, aerosols, and flowables. 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 the amount and concentration used may vary depending on the dosage form, application time, method, location, target disease, target crop, etc., so they may be increased or decreased 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'-para-tert-butylbenzyldithiocarbonimidate, O,O-dimethyl-O-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, manganis 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
-Methyl-4-chlorophenoxybutyric acid; Phenoxy herbicides such as 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-3'-methoxyphenyl ether; 2,4
-dichlorophenyl-3'-methoxycarbonyl-
Diphenyl ether herbicides such as 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; triazine herbicides such as 2-methylthio-4,6-bisisopropylamino-1,3,5-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-benzothiazolyl)-1,3
-Urea herbicides such as dimethylurea, carbamate herbicides such as isopropyl-N-(3-chlorophenylcarbamate; methyl-N-(3,4-dichlorophenyl)carbamate, S-(4-chlorobenzyl)- N,N-diethylthiol carbamate; Thiol carbamate herbicides such as S-ethyl-N,N-hexamethylenethiol carbamate, 3,4-dichloropropionanilide; N-methoxymethyl-2,6-diethyl-α
-Chloracetanilide; 2-chloro-2',6'-
Diethyl-N-(butoxymethyl)-acetanilide; 2-chloro-2',6'-diethyl-N-(n-
propoxyethyl)-acetanilide; N-chloroacetyl-N-(2,6-diethylphenyl)-
Acid anilide herbicides such as glycine ethyl ester, 5-bromo-3-secondary butyl-6-
Methyluracil; 3-cyclohexyl-5,6-
Uracil herbicides such as trimethylene uracil,
Pyridinium chlorine herbicides such as 1,1'-dimethyl-4,4-bispyridinium chloride, N,N
-bis(phosphonomethyl)-glycine, O-ethyl-O-(2-nitro-5-methylphenyl)-N
-Secondary butyl phosphoramidothioate, S-(2-methyl-1-piperidylcarbonylmethyl)O,O-di-n-propyldithiophosphate; S-(2-methyl-1-piperidylcarbonylmethyl)O, Phosphorus herbicides such as O-diphenyldithiophosphate, toluidine herbicides such as α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-P-toluidine, 5-
Tertiarybutyl-3-(2,4-dichloro-
5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one; 3-isopropyl-
(1H)-2,1,3-benzothiadiazine-(3H)
-one-2,2-dioxide, α-(β-naphthoxy)propionanilide, 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl p-toluenesulfonate, 3-
(Methoxycarbonylamino)phenyl 3-methylphenyl carbamate, 4-amino-3-methyl-6-phenyl-1,2,4-triazine, etc. can be used in combination, and each single agent can control It does not reduce the effect. The present compound can also be used in combination with an insecticide, such as O,O-dimethyl O-(4-nitro-3-methylphenyl).
Phosphorothioate, O-(4-cyanophenyl)
O,O-dimethyl phosphorothioate, O-(4
-cyanophenyl)O-ethylphenylphosphonothioate, O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate, 2
-organophosphorus insecticides such as -methoxy-4H-1,3,2-benzodioxaphosphorine-2-sulfide, O,O-dimethyl S-(1-ethoxycarbonyl-1-phenylmethyl)phosphorodithioate, α-cyano-3-phenoxybenzyl 2-
(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-dimethyl-3-(2,
Mixed with pyrethroid insecticides such as 2-dichlorovinyl) cyclopropane carboxylate and α-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylate. can be used,
None of these will reduce the control effect of each single agent.
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. Next, the present invention will be explained in more detail with reference to Examples. Unless otherwise specified, NMR spectra are expressed as δ values using deuterated chloroform as a solvent and using tetramethylsilane as an internal standard. Example 1 [-E] of 3-(4-chlorophenyl)-1-(1-methyl-cyclopropyl)-2-(1,2,4-triazol-1-yl)-2-propen-1-ol Synthesis of isomer (compound number 1) 3- Characterized by the NMR spectrum below
(4-chlorophenyl)-1-(1-methylcyclopropyl)-2-(1,2,4-triazole-1
-yl)-2-propen-1-one [-E]
2.9 g (0.01 mol) of the isomer (melting point 89-92°C) was dissolved in 50 ml of methanol. While cooling this on ice and keeping the reaction temperature below 20℃, sodium borohydride was added.
0.38 g (0.01 mol) was added. After keeping it at 20°C for 3 hours, 100 ml of water and 2 ml of acetic acid were added to decompose it, and the organic layer was extracted with 100 ml of chloroform. 5% baking soda solution
After washing with 50 ml, it was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was crystallized in 5 ml of a mixed solvent of carbon tetrachloride and n-hexane (1:1) to obtain 2.4 g (yield: 85%) of the title compound. Starting material; 3-(4-chlorophenyl)-1-
(1-methylcyclopropyl)-2-(1,2,4
-triazol-1-yl)-2-propene-1
The NMR spectrum of the [-E] isomer of -one is shown. 8.28 (1H, singlet, triazole proton) 8.07 (1H, singlet, triazole proton) 7.32 (4H, singlet, phenyl proton) 7.19 (1H, singlet, olefin proton) 1.45-1.15 (2H, multiplet, cyclopropyl group) Methylene proton) 1.25 (3H, singlet, methyl proton) 0.99-0.75 (multiplet, methylene proton of cyclopropyl group) Example 2 3-(4-chlorophenyl)-1-(1-methyl-cyclopropyl)-2- Synthesis of [-Z] isomer of (1,2,4-triazol-1-yl)-2-propen-1-ol (compound number 2) 3- characterized by the following NMR spectrum
(4-chlorophenyl)-1-(1-methylcyclopropyl)-2-(1,2,4-triazole-1
-yl)-2-propen-1-one [-Z]
2 g (0.007 mol) of the isomer (melting point 74-75°C) in 50 ml of methanol and 0.27 g of sodium borohydride.
(0.007 mol) in the same manner as in Example 1, 1.7 g of the title compound (yield 85
%) was obtained. Starting material; 3-(4-chlorophenyl)-1-
(1-methylcyclopropyl)-2-(1,2,4
-triazol-1-yl)-2-propene-1
The NMR spectrum of the [-Z] isomer of -one is shown. 8.12 (1H, singlet, triazole proton) 8.03 (1H, singlet, triazole proton) 7.55 (1H, singlet, olefin proton) 7.21 (2H, tablet, phenyl proton, J
=8Hz) 6.81 (2H, tablet, phenyl proton, J
= 8 Hz) 1.50 to 1.25 (2H, multiplet, methylene proton of cyclopropyl group) 1.28 (3H, singlet, methyl proton) 0.90 to 0.65 (2H, multiplet, methylene proton of cyclopropyl group) Illustrate the invented compounds and
NMR spectra are also listed. These compounds can be synthesized by the same method as in Examples 1 and 2.

【table】

【table】

【table】

【table】

[Table] Next, Examples and formulation examples will be described to further clarify the usefulness of the compounds of the present invention as agricultural and horticultural disinfectants, weed killers, and plant growth regulators. Example 3 Effect of barley powdery mildew control by foliage spraying (seedling test) A 150 ml plastic pot was filled with sandy loam, and 10 to 15 barley seeds (variety: Goune Shiseki) were sown. This was cultivated in an air-conditioned greenhouse at 18 to 23°C for 7 days to obtain barley seedlings with the first true leaves developed. 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 air-drying the chemical solution, the seedlings were inoculated with barley powdery mildew fungus (Erysiphe graminis), and placed in a constant temperature chamber at 23℃ for 10 minutes under fluorescent lighting.
After cultivation for one day, the disease state of the first true leaves was observed. The disease severity was calculated by the following method. That is, depending on the degree of lesion appearance on the investigated leaves, 0, 0.5,
The disease was classified into indexes 1, 2, and 4, and the severity of the disease was calculated using the following formula. (Infection index) (Infection state) 0...No bacterial flora observed on the leaf surface. 0.5… 〃 Bacterial flora is observed on less than 5% of the leaf area. 1... 〃 Less than 20% 〃 2... 〃 Less than 50% 〃 4... 〃 50% or more 〃 Incidence (%) = Σ (Infection index) x (Number of leaves) / (Number of leaves examined)
×4×100 Next, the prevention value was calculated from the following formula. Control value (%) = 100 - (incidence in compound-treated area/incidence in untreated area) x 100 As a result, as is clear from Table 2, the compound of the present invention has an excellent barley powdery mildew control effect. show,
Its efficacy was superior to that of the control compound used to control barley powdery mildew.

【table】

[Table] Note (1) Comparative control compound (commercially available fungicide)
Example 4 Wheat rust control effect (therapeutic effect) (seedling test) A 150 ml plastic pot was filled with sandy loam, 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 (Puccinia recondita).
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 lighting 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 Example 3. As a result, as is clear from Table 3, the compounds of the present invention exhibited excellent wheat rust control effects;
Comparisons were made with a control compound.

[Table] Note (1) Comparative control compound (commercially available fungicide)
Example 5 Controlling effect on rat snail brown spot A 150 ml plastic pot was filled with sandy loam, and one seed of rat snail (variety: semi-erect) per pot was sown. This was cultivated for 12 days in an air-conditioned greenhouse at 2.5 to 30°C to obtain a young seedling with the third true leaf developed. 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, the plants were covered with vinyl to maintain humidity, and placed in an air-conditioned greenhouse at 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. The disease onset investigation method and control value calculation were performed in the same manner as in Example 3. As a result, as is clear from Table 4, it showed a high pesticidal effect similar to that of the comparative control compound.

[Table] Note (1) Comparative control compound (commercially available fungicide)
Example 6 Bacterial growth inhibition effect 5g of polypeptone and malt extract per 1 liter of water
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.

【table】

[Table] As a result, as shown in Table 5, the [-E] isomer of the compound of the present invention has higher fungicidal activity against a wider range of plant pathogens than the [-Z] isomer. There was found.

[Table] Example 7 Pottomum (variety: Snow Ridge) was grown in a 4-inch clay pot filled with 500 g of synthetic soil made of sea sand, mountain soil, and beets, and pinched two weeks after planting to grow 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 6. 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, B-nine (N,N-
dimethylaminosuccinimizucacide) was used.

[Table] Example 8 A Wagner pot with a diameter of 14 cm filled with 1.5 kg of paddy soil was turned into a paddy field, and rice seedlings at the 3-leaf stage were transplanted.
Furthermore, Japanese mulberry seeds were sown, and a predetermined amount of the chemical was applied to the flooded soil. On the 25th day after the chemical treatment, the herbicidal efficacy and the degree of chemical damage were investigated for the transplanted or sown plants, naturally occurring broad-leaved weeds such as Aspergillus japonica, Azalea japonica, and Kikashigusa, as well as Japanese grasshopper. The results are shown in Table 7. Regarding the treatment method, a predetermined amount of the drug was treated in the form of a wettable powder at a rate of 15 c.c. per pot. During the treatment, the solution was added dropwise using a pipette. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. 0... Weed suppression rate 0-9% 1... 10-29 2... 30-49 3... 50-69 4... 70-89 5... 90-100 Regarding chemical damage, plant height, The ratio of the number of tillers and total amount (air dry weight) to the untreated plot was calculated, and the worst value among the three factors was taken and evaluated on a scale of 0 to 5. 0... Ratio to untreated area 100% 1... 90-99 2... 80-89 3... 60-79 4... 40-59 5... 0-39

[Table] Formulation example 1 Powder 2 parts of the present compound (3), 88 parts of clay, and talc
By thoroughly grinding and mixing 10 parts, a powder with a base ingredient content of 2% can be obtained. Formulation Example 2 Powder 3 parts of the compound of the present invention (4), 67 parts of clay, and talc
By thoroughly grinding and mixing 30 parts, a powder with a base ingredient content of 3% can be obtained. Formulation example 3 Wettable powder 30 parts of the present compound (1), 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate) and dispersing agent (calcium lignin sulfonate)
By thoroughly grinding and mixing the two parts, a hydrating agent with a base ingredient content of 30% can be obtained. Formulation example 4 Wettable powder 50 parts of the compound of the present invention (5), 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly grinding and mixing 2.5 parts, a hydrating agent with a base ingredient content of 50% can be obtained. Formulation Example 5 Emulsion 10 parts of the compound of the present invention (6), 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 the compound of the present invention (2), 40 parts by weight of bentonite, 50 parts by weight of clay and 5 parts by weight of sodium ligninsulfonate were thoroughly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation and drying. to obtain granules.

Claims (1)

[Claims] 1. General formula (In the formula, X represents a halogen atom, and n represents 0, 1 or 2.) A triazole compound or a salt thereof. 2 General formula (In the formula, X represents a halogen atom, and n represents 0, 1 or 2.) A general formula characterized by reducing a ketone compound represented by the following using a reducing agent: (In the formula, X and n have the same meanings as shown above.) A method for producing a triazole compound or a salt thereof. 3 General formula (In the formula, X means a halogen atom, and n means 0, 1 or 2.) An agricultural and horticultural fungicide characterized by containing a triazole compound or a salt thereof as an active ingredient. 4 General formula (In the formula, X means a halogen atom, and n means 0, 1 or 2.) A herbicide characterized by containing a triazole compound or a salt thereof as an active ingredient. 5 General formula (In the formula, X represents a halogen atom, and n represents 0, 1 or 2.) A plant growth regulator comprising a triazole compound or a salt thereof as an active ingredient.