JPS58128383A - Triazole compounds, their production methods, and agricultural and horticultural fungicides, plant growth regulators, or herbicides containing them as active ingredients - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention The present invention is based on the general formula [■] [wherein, X represents a hydrogen atom or a hydrogen atom, and 1 and 2 are the same or different, group, haloalkyl group, phenylalkyl group, or phenyl group unsubstituted or substituted with a halogen atom;
2) It can also be an alkylene chain represented by n-. n is 2
Represents an integer between ~5. ] The present invention relates to a triazole compound represented by the following, a method for producing the same, and an agricultural and horticultural fungicide, a plant growth regulator, or a herbicide containing the triazole compound as an active ingredient.

A large number of synthetic organic compounds with antibacterial properties have been discovered and developed as agricultural fungicides to protect garden crops from pathogens and have greatly contributed to the stable supply of agricultural products (5). 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 such problems is to
The goal is to use compounds that have a higher bactericidal effect against plant pathogens, and to simultaneously control diseases by using compounds that have bactericidal activity against a broader range of pathogens.

The present inventors conducted research on triazole compounds and found that the compound represented by the general formula [I] has excellent properties as an agricultural and horticultural fungicide, and also exhibits plant growth regulating and herbicidal effects. 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 blight;
Black spot, powdery mildew, red leaf spot and black spot of pears, black spot, scab, black pox, green mold and blue mold of mandarin oranges, (6) gray leaf spot of peaches, late rot of grapes , botrytis, powdery mildew and rust, crown rust of oat, powdery mildew of barley, cloud rot, patchy leaf disease, naked smut, hard smut, snow rot rot and black rust, wheat Fusarium rust, naked smut, smut, leaf blight, rotten blight, yellow rust, black rust,
Powdery mildew, powdery mildew of cucurbits, botrytis, vine blight, sclerotinia and blight, tomato leaf mold, powdery mildew and ring spot, botrytis of eggplant, half-wilt and powdery mildew, powdery mildew of green pepper, gray mold and powdery mildew of strawberry, red starch and powdery mildew of tobacco, brown spot of sugar beet, and black astringency and brown spot of white sugar beet.

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 and wheat cultivation, lodging of rice plants caused by excessive application of fertilizers and strong winds is often a serious problem, but by applying this compound at the appropriate time, the plant height of rice and wheat plants can be moderately suppressed. It is effective in controlling the length and preventing lodging.

In the cultivation of potted chrysanthemums, application of this compound will not affect the flowers, and by shortening the length of the stems, the commercial value can be increased.

In addition, the compound of the present invention has a herbicidal effect, and has a herbicidal effect on upland weeds of the Poaceae family, such as barnyard grass, grasshopper, and foxtail grass;
It has a strong effect on broad-leaved field weeds such as blueberry, whiteweed, purslane, and chickweed, as well as against common and perennial weeds in paddy fields, such as Japanese millet, Japanese commonweed, commonweed, Japanese horsetail, bulrush, and silver grass.

When this compound is used in fields, it is highly effective against major weeds in fields, and is effective both in soil treatment before the emergence of brambles 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 this compound 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, side dishes, orchards, lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forests, non-agricultural lands, and the like.

Preferred examples of R1 and R2 in the compound of the present invention (Il) include a hydrogen atom, a 01-C6 alkyl group, a 01-C6 alkyl group optionally substituted with a fluorine atom, a chlorine atom, or a bromine atom, a 01-C8 01-CB alkyl group substituted with an alkoxyl group, a phenylalkyl group such as a benzyl group, a phenethyl group, a phenylpropyl group,
An unsubstituted or substituted phenyl group with a chlorine atom, bromine atom, or fluorine atom, or R and R combine to form an alkylene chain, and together with the root carbon atom, an 8-membered,
It may be a 4-, 5-, or 6-membered (9) cyclic alkyl group.

The present invention also includes salts of the present triazole compound, and salts include acids that are physiologically acceptable to plants, such as inorganic acids such as hydrochloric acid, hydrochloric acid, hydroiodic acid, sulfuric acid, and nitric acid; These are salts with carboxylic acids such as acetic acid, trichloroacetic acid, maleic acid, and succinic acid, sulfonic acids such as p-toluenesulfonic acid, or phosphoric acids.

In the compound of the present invention (Il), when 几 and 几 are different, two types of stereoisomers exist. The present invention includes both stereoisomers and mixtures of stereoisomers.

The compound fl of the present invention can be produced, for example, by the following method.

ia) Triazolylpropanediol compounds represented by the general formula rI [] and aldehydes represented by the general formula [■] (when C itl or 2 is a hydrogen atom) or ketones (R and J (both are hydrogen atoms) (non-atomic) in the presence of an acid to obtain the compound rr of the present invention.

(10) [In the formula, ■, R and X have the same meanings as shown above. ] The solvent used is an aromatic hydrocarbon (benzene.

toluene, etc.) and halokenized hydrocarbons (carbon tetrachloride,
Hydrohydrogens such as chloroform, methylene chloride, dichloroethane, etc.) or a mixed solvent of these R hydrogen IM and alcohols (methanol, ethanol, propatool, butanol, etc.) can be used. Suitable acids for the reaction are mineral acids such as hydrochloric acid, sulfuric acid, hydrobromic acid, and sulfonic acids such as p-toluenesulfonic acid.

The reaction is a triazolylpropanediol compound [■],
Equimolar or excess amount of ketone or aldehyde [in the presence of ml and catalytic amount of acid, in a suitable solvent, at a reaction temperature from room temperature to the boiling point of a convenient solvent Q], using a water separator. The reaction is accelerated by doing so.

(b) Acetals (l (or when B is a hydrogen atom) or ketals (generally R In the presence of an acid, the compound of the present invention [D
get.

[■]

[In the formula, ratio, general and X have the same meanings as shown above, and R8 represents an alkyl group. ] The types of solvent and acid used are the same as in the case of fal. The reaction is carried out in the presence of a triazolylpropanediol compound [■], an equimolar or excess amount of acetal or ketal [W], and a catalytic amount of acid, and the boiling point of the solvent used from room temperature in an appropriate solvent. The reaction temperature is up to

Raw material triazolylpropanediol compound [■
] can be manufactured by the following method.

[In the formula, X has the same meaning as shown above. ] Ketone compound [■] (compound known in British Patent No. 1464224) and sulfoxonium methylide are reacted to form an epoxy compound [■], and then hydrolyzed under alkaline or acidic conditions, A triazolylpropanediol compound [1r] can be obtained (see production side).

(13) When the manufacturing method (al or R7 in the manufacturing method) and LJ are different, the compound tI) of the present invention has two stereoisomers and is generally obtained as a mixture of stereoisomers. If necessary, each stereoisomer can be separated by silica gel column chromatography, high performance liquid chromatography, fractional crystallization, or the like.

Examples of the compounds of the present invention are shown in Table 1.

Table 1 (14) Table A, Compounds 6, 7.9, 10.12 and 13 are 10,000 and the other stereoisomer, respectively. Also compound 8.11.1'
4.15.16 and 17 are mixtures of two stereoisomers.

Next, the method for producing the compound of the present invention will be specifically described with reference to production examples.

Production example 1 fa14-(2,4-dichlorophenyl)-4-(1,
2,4-1-riazol-1-yl)methyl-2,2-
Production method of dimethyl-1,3-dioxolane [Compound 8] 2-(2,,4-dichlorophenyl)-3-(1,2
, 4-1-riazol-1-yl)-1,2-propanediol 2.9 f (0,01 mol), 2,2-dimethoxypropane 6 g (0,06 mol), p-++-luenesulfonic acid A mixture of 50 m/ml of toluene and 100 m/ml of toluene was heated under reflux for 1 hour. Transfer the reaction solution to a separatory funnel,
%Na1iCUa water, and the toluene layer was concentrated under reduced pressure. The obtained crystalline surface was recrystallized from a mixed solvent of carbon tetrachloride and n-hexane (1:2) to obtain the title compound 2. ,．． 9 g (yield 90%) was obtained. mp128~
129℃fb1.2-(2,4-dichlorophenyl)-
3-(],, ]2.4-triazol-1-yl-1
゜Production method of 2-propanediol 27 (2,,4-dichlorophenyl)-3-(1,2,
A mixture of 2.79 (0.01 mol) of 4-triazol-1-yl)-1<2-epoxypropane, 6 ml of dioxane 24-1 water and concentrated sulfuric acid 4- was heated under reflux for 6 hours. After neutralizing the reaction solution by adding 5% weight water, it was extracted with 300 g of chloroform. The crystalline residue obtained after concentration under reduced pressure is ethanol and n-hexane (1:8)! : Recrystallization from a mixed solvent gave 2 g (yield 70%) of the title compound. mp125-126℃IQ) 2-(2,4-dichlorophenyl)-3-(1,2,4-triazole-1
-yl)-1゜Production method of 2-epoxypropane 60% oily NaH2,6Q (0,065 mol) OD
M-so, suspended in 2□-, trimethylsulfoxonium iodide (CHs, ) a 8 (Jll
49 (0,064 mol) was added. Then l-(,,
2,,,,4-dichlorophenyl-2= (1.

(17) 2.4=triacyl-1-yl)-2-ethanone 1
-4 y (0,0155 mol) of DM8 (J30me
A bath solution was added and the mixture was stirred at 60°C for 8 hours. Pour the reaction solution into ice water 3
The title compound 7.0 was poured into 0.0-ml and extracted with 800-chloroform, concentrated, and purified by silica gel column chromatography (acetone-20-hexane-1:10) to give the title compound 7.0 as an oil. jf (yield 50%) was obtained.

4 n D] -5658 Production Example 2 (at t=(p-chlorophenyl)-2-ethyl-4-(1,2,4-1 riazol-1-yl)methyl-1,8-dioxolane [Compound 6゜7〕 manufacturing method
・2-(p-chlorof,enyl)-8-(,1゜2.4-
1 riazol-1-yl)-propanediol 2.5 g
(0.01 mol), propionaldehyde diethyl acetal 7 g (0.09 mol), p=toluenesulfonic acid jOrng and toluene 100 mg were heated under reflux for 4 hours.

(I8) The reaction solution was transferred to a separating funnel, washed with 5% deuterated water (100%), concentrated under reduced pressure, and then subjected to silica gel column chromatography (acetone:hexane = 1:80) to separate the two types of products. The stereoisomers were separated. First, 10,000 steric Mu forms of the title compound o, 4 f/ (yield 84 x)
"Fl-5209 [Compound 6] eluted, followed by the other stereoisomer 0.6N (52% yield) np 1.5J3
19 [Compound 7] was obtained.

Song 2-(p-chlorophenyl)-8-(1°2.4-
) Riazol-1-yl)-propanediol production method 2-(p-chlorophenyl)-8-(1°2.4-)riazol-1-yl)-1,2-epoxypropane2.
89 (0.01 mol), dioxane 24tn1. , water 6- and concentrated sulfuric acid 4- were carried out in the same manner as in Production Example 1 to obtain 2 g (yield 79%) of the title compound mp121~
A temperature of 122°C was obtained.

(e) 2-(P-chlorophenyl)-8-(1°2.4
1-(p-chlorophenyl)-2-(1゜2.4-1-
Riazol-1-yl)-ethanone 99 ((LO4 mol), 60% oily Na 141.6 g (0.04 mol),
Trimethylsulfoxonium iodide 8.8&(0
, 04 mol) and l) MSU50d in the same manner as in Production Example 1(C) to obtain 5 g (yield 53%) of the title compound nDl, 5492.

Production example 3 4-(2,4-dichlorophenyl)-4-(1,2,4
2-(2,4-dichlorophenyl)-8-(1,2,4
,-triazol-1-yl)-1゜2-propanediol 2.91CO1O1 mol), n-butyraldehyde 8g (0.z mol), concentrated sulfuric acid 1 drop, toluene 100 m
1 and methanol 1O- were heated under reflux for 1 hour with a water separator attached. The reaction solution was transferred to a separatory funnel, washed with 100 - of 5% deuterated water, and concentrated under reduced pressure to obtain 8.2 g (yield 94%) of the title compound n,s 1-5846.
Obtained as a mixture of stereoisomers of the species.

Production example 4 4-(2,4-dichlorophenyl)-2-ethyl-2-
n-propyl-4-(1,2,4-triazole-1-
2-(2,4-dichlorophenyl)-3-(1,
2,4-triazol-1-yl)-1゜2-propanediol 2.9f (0.0'1 mol), 2-pentanone 10N (0.12 mol), 1 drop of concentrated sulfuric acid, toluene 100
trt and n-butanol 10- were heated under reflux for 1 hour with a water separator attached. The reaction solution was transferred to a separatory funnel, washed with 100% of 5% deuterated water, and concentrated under reduced pressure to obtain the title compound 8.2 (IC yield: 91%) (21) nDl, 5847 as two stereoisomers. Obtained as a mixture.

When using the compound of the present invention obtained in this way,
It may be used as it is without adding any other ingredients, or it may be mixed with solid carriers, liquid carriers, surfactants, and other auxiliary ingredients for formulations, such as powders, granules, wettable powders, emulsions, etc. It may be made into fine particles jflJ, oil solution, tablet, aerosol, flowable, etc.

Each formulation contains the compound of the present invention as an active ingredient in a weight ratio of 0.
, t~99.9%, preferably 1.0~80.0%. These formulations can be prepared according to conventional methods.

In this case, solid carriers include vegetable carriers (e.g. wheat flour, tobacco stalk powder, soybean flour, walnut shell powder, wood flour, sawdust, bran, bark powder, cellulose powder, residue after extracting plant extracts), textile products. (e.g. paper, cardboard, Erugire), crushed synthetic resins, clays (e.g. kaolin, bentonite, acid clay), talc, and other inorganic minerals (22
) (for example, pyrophyllite, sericite, pumice, sulfur powder, activated carbon), fine powders or powders, and chemical fertilizers (for example, ammonium sulfate, ammonium phosphorus, ammonium nitrate, urea, ammonium chloride), etc. Liquid carriers include water, alcohols (e.g. methyl alcohol, ethyl alcohol), ketones (e.g. acetone, methyl ethyl ketone), ethers (e.g. ethyl ether, dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons. (e.g. benzene, toluene, xylene, methylnaphthalene), I]1Hf7F group hydrocarbons (e.g. gasoline,
kerosene, kerosene), esters, nitriles, acid amides (e.g. methylformamide, dimethylacetamide), halogenated hydrocarbons (e.g. dichloroethane,
Examples include trichlorethylene, carbon tetrachloride), etc.

Next, as surfactants, alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates,
Examples include polyethylene glycol ethers and polyhydric alcohol esters. In addition, usable fixing agents and dispersants include casein, gelatin, starch powder, C
Examples of stabilizers include MC, gum arabic, alginic acid, lignin sulfonate, bentonite, molasses, borihinyl alcohol, pine oil, and agar.
Examples include P (isopropyl phosphate), TCP (tricresyl phosphate), tall oil, epoxidized moieties, various surfactants, and various fatty acids or their esters. Furthermore, the compound of the present invention can be used in combination with other fungicides, insecticides, nematicides, acaricides, pest repellents, plant growth regulators, herbicides, fertilizers, soil conditioners, etc.

Examples of formulations are shown below. Note that parts represent parts by weight.

Formulation Example 1 Powder 2 parts of the compound 2 of the present invention, 88 parts of clay and 10 parts of talc
By thoroughly pulverizing and mixing the two parts, a powder of 2A is obtained.

Formulation Example 2 Wettable powder 10 parts of the compound of the present invention 5, 65 parts of diatomaceous earth, White l-
- 20 parts of bottle, 3 parts of wetting agent (sodium lauryl sulfate) and 2 parts of dispersing agent (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a 10π wettable powder.

Formulation Example 3 Wettable powder: If 25 parts of the compound 9 of the present invention, 70 parts of diatomaceous earth, 2.5 parts of MM3M (calcium alkylbenzenesulfonate) and 2.5 parts of a dispersant (calcium ligninsulfonate) are thoroughly ground and mixed, 25 parts of the compound 9 of the present invention is prepared. % hydration agent.

Formulation Example 4 Emulsion 20 parts of the present compound 3, 60 parts of xylene, and an emulsifier (polyoxyethylene phenylphenol polymer type)
Mixing 20 parts gives a 20% emulsion.

Formulation Example 570 Able Agent A mixture of ultrafine powder of 20 parts of the compound 2 of the present invention and 5 parts of white carbon, 2 parts of polyoxy(25) ethylene nonylphenol ether, 1 part of carboxymethyl cellulose, and 72 parts of water are uniformly mixed, Stir and mix with a homogenizer for 20 minutes until the main ingredient content is 20.
Obtain % flowable agent.

When applying the compound of the present invention, usually 1 g per 10 are
A range of ~100g is appropriate, and the application concentration is 0.0
The range is preferably from 0.001% to 0.05%. These application ranges and application concentrations vary depending on the formulation, and also vary depending on the time of application, location, application method, type of disease, type of plant, severity, and other conditions, and can also vary depending on the type of object. Furthermore, the concentration may be changed by increasing or decreasing the concentration without being limited to the above range.

Next, test examples will be shown to illustrate the effects of the compounds of the present invention as agricultural and horticultural fungicides, plant growth regulators, and repair agents in μ bodies.

Test Example 1 Barley powdery mildew control effect (preventive effect test) Flastinoku Bottle!・Fill barley with sandy loam (
Variety: Akashinriki) was sown. This was cultivated in a wet (26) room for 7 days to obtain barley seedlings in which the first true leaves had developed.

On this video, a water-diluted solution of the test compound in emulsion form was sprayed on the leaves until enough droplets were attached to the leaf surface. After air-drying the chemical solution, barley powdery mildew fungus ('Erysiphe grat)
After inoculating the conidia of S. ninis and cultivating them under fluorescent lamp illumination at 20° C. for 10 days to induce disease, the disease state was observed.

The disease severity was calculated by the method described in F. That is, depending on the degree of appearance of lesions on the investigated leaves, they were classified into indexes of 0°1.2.4.8, and the degree of disease severity was calculated using the following formula.

(Sickness index) (Sickness state) 0
No bacterial flora or lesions are observed on the leaves.

1. Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area.

2. Bacterial flora or lesions are observed on the leaf surface in less than 2ocX of leaf area.

4 Bacterial flora or lesions are observed on the leaf surface in less than 50% of the leaf area.

8 Bacterial flora or lesions are observed on the leaf surface over 50LX of leaf area.

Next, the control value was calculated using the following formula.

As a result, the results shown in Table 1 were obtained.

The compound of the present invention showed a superior control effect compared to the comparative compound.

Table 1 Note (1) Comparative control compound; commercially available fungicide Tridemorph (2
9) Test Example 2 Wheat rust control effect (therapeutic effect test)
Fill a rough, 5-tsuku pot with sandy loam and sow 1 wheat (Product Building: Norin No. 73). Cultivate this in a greenhouse for 7 days, and grow the wheat seedlings with their first true leaves. Obtained.

Wheat rust fungus (Pucciniarec
ondita) and placed in a greenhouse at 28°C for 16 hours to infect the bacteria. Subsequently, a water-diluted solution of the test compound in the form of an emulsion was sprayed on the leaf surface until the droplets were sufficiently attached. 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 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 1.

As a result, the results shown in Table 2 were obtained.

The compound of the present invention showed a superior control effect compared to the comparative compound.

Notes to Table 2 (1) Comparative control compound; Commercially available fungicide Triadimefon Test Example 8 Apple scab control effect (preventive effect test) A plastic pot was filled with sandy loam, and phosphorus %a was sown. This was cultivated in a greenhouse for 14 days to obtain apple seedlings m with the fifth leaf developed. A water-diluted solution of the test compound in the form of an emulsion was sprayed onto the seedlings until sufficient droplets adhered to the leaf surface. After the chemical solution had been air-dried, the seedlings were inoculated with conidia of the apple scab fungus (Venturia 1naequalis) and cultivated in a greenhouse at 15° C. for 16 days to develop the disease, and then the disease state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As a result, the results shown in Table 8 were obtained.

The compound of the present invention showed a superior control effect compared to the comparative compound.

Table 3 Note (1) Comparison control compound i; Commercially available fungicide Cabtan test example 4 Peanut brown spot control effect (absorption transfer test) Sand loam was filled in a plastic pot, ) was sown. This was cultivated in a greenhouse for 7 days to obtain peanut seedlings in which the 8th true leaf had developed. A predetermined amount of a water-diluted solution of the test compound in the form of an emulsion was sprinkled onto the soil of these young seedlings, and after 4 days, Cercospora arachidicola
) Noconidia suspension was inoculated with rgAM.

This was cultivated in a greenhouse at 25°C for 16 days to develop the disease, and the disease state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As a result, the results shown in Table 4 were obtained. The compound of the present invention showed a superior control effect compared to the comparative compound.

Table 4 Note (1) Comparative control compound; Commercially available herbicide Daconil (3
8) Test Example 5: Effect of suppressing leather height on dice and barley Add 10-ml diluted solution with water and thoroughly stir the cotton mixture. Return to the original pot, and add 3 dice and 5 grains of barley to the chemical-treated soil. Sowed.

This was cultivated in a glass room at 25°C, and the plant height of dice and barley was measured 14 days later.

The results are shown in Table 5, and the numerical values in the table represent the index (X) when the average value of the plant heights of 2 dice or 3 barley plants is set as 100 for Mujokun.

Test Example 6 Plant height suppression effect on Botmum Botmum (variety: Yellow Parabon) was cultivated in clay pots filled with synthetic soil consisting of sea sand, excavated soil, and beets, and pinched two weeks after planting to produce three plants. After the new shoots had grown, a diluted solution of the compound of the present invention at a predetermined concentration was applied two weeks after pinching, and the growth-inhibiting effect was given as a supplement on the 42nd day after the chemical treatment. The results are shown in the fourth column. In addition, to evaluate the effect, the plant height of Botmam at the time of chemical treatment was measured in advance, and the growth length during this period was calculated from the difference from the plant height on the 42nd day after treatment.
It was expressed as an elongation index when the elongation of the untreated area was set as 100. Values represent the average of triplicate.

Table 6 Note (1) KK4m reference compound - (dimethylamino)succinamic acid Test Example 7 Field weeding test (pre-planting soil treatment test) Soil mixed with each of the seeds of crabgrass, blueberry, and whiteweed was placed in a Wagner pot. A predetermined amount of the raw material was packed into an emulsion, diluted with water, and the soil surface was treated with a hand sprayer.

After the treatment, the five-leaf sugar beet (variety Monohill) grown in paper pots was transplanted to Wagnerbot. Thereafter, the plants were grown in a greenhouse, and 20 days after treatment, the herbicidal efficacy and crop damage were observed, and the results are shown in Table 7. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below.

However, the phytotoxicity of crops is also the same as the weight removal effect, which is equivalent to M.

0・・・・・・Weed suppression rate O~9%18018
1191. 〃 JO~ 292...
・・・・・・ 〃 30〜498 ・・・・・・
・・・・・・ 〃 50〜694 ・・・・・・
・・・〃 70〜895 ・・・・・・・・・
・〃 90-100 Table 7 (37) Test Example 8 Field weed control test (post-germination foliage treatment test) Fill pots with soil mixed with each of the seeds of crabgrass, blueberry, and whiteberry, and add 5 grains of two-row barley. was sown. After covering the plants with soil and growing them in a greenhouse for two weeks, a predetermined amount of the chemical was applied to the entire stem and leaves from above using a hand sprayer until the droplets were sufficiently attached to the leaves.

After the chemical treatment, the plants were grown in a greenhouse for another three weeks, and then the herbicidal efficacy of each plant was investigated.

The results are shown in Table 8. The amount of treatment agent was formulated into an emulsion, a predetermined amount was dispersed in water (including a spreading agent), and the test was conducted at a rate of 5 liters per are. Evaluation of herbicidal efficacy was expressed as a number of θ to 5 as shown below. However, phytotoxicity of crops is also expressed using the same criteria as herbicidal efficacy.

0...Weed suppression rate 0-9%1...
・・・ 〃 10～292・・・・・・・・・
〃 30～498・・・・・・・・・ 〃 5
0~69(38) 4...Weed suppression rate 70~89%5...
・・・・・・ 〃 90～100 8th
Table * Growth suppression (89 completed) 759-

Claims (3)

[Claims] (1) General formula [wherein, Represents a phenyl group substituted with an atom, R1 and R2 are bonded to -(C
H) It can also be an alkylene chain represented by n-. n is 2
Represents an integer between ~5. ] A triazole compound represented by (2) General formula [wherein, X represents a hydrogen atom or a chlorine atom]. [In the formula, Ltl and R are the same or different, and a hydrogen atom, an alkyl group, an alkoxyalkyl group, a haloalkyl group, a phenylalkyl group, or an unsubstituted or Represents a phenyl group substituted with a halogen atom, R1 and lt2
can also be bonded to form an alkylene chain represented by -((J2)n-, where n represents an integer of 2 to 5). The general formula is characterized by reacting with acetals or ketals having the same meaning as shown above, and Ⅰ 8 represents an alkyl group. The meaning is the same as shown above.] A method for producing a triazole compound shown by. 10
A phenyl group substituted with a gen atom can also be combined with an alkylene chain represented by -((J2)n-, where n represents an integer from 2 to 5.) An agricultural and horticultural fungicide, plant growth regulator, or herbicide characterized by containing a triazole compound as an active ingredient.