JPH021481A - Novel triazole compound and production thereof - Google Patents

Abstract

NEW MATERIAL:The compound of formula I {R1 and R2 are lower alkyl, cycloalkyl, alkenyl, alkynyl, etc.; A is group of formula II-VI [X is H, (OH- substituted) lower alkyl, etc.; R3 is H or lower alkoxy; m is 0-4; p and q are 2-5]; n is 0-2}. EXAMPLE:3-(2-Chloro-4-trifluoromethylphenylthio)-1,2,4-triazole. USE:A herbicide. PREPARATION:A compound of formula VII is made to react with a compound of formula VIII (Y is halogen) and, as necessary, the product is oxidized.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides - Maximum! : (In the formula, R1 and R2 are the same or different and represent a lower alkyl group, cycloalkyl group, alkenyl group, or alkynyl group, or R1 and R2 together with the nitrogen atom to which they are bonded have 4 carbon atoms. ~6 azacycloalkane, A is the following formula: % formula % X is a lower alkyl group, a cycloalkyl group, an alkoxy group, which may be substituted with a hydrogen atom or a hydroxyl group,
It represents an alkoxycarbonyl group, an alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxybenzyl group, a halogen, a nitro group, an amine group, or a trifluoromethyl group, and R3 represents a hydrogen atom or a lower alkoxy group.

information represents the number 0, 1, 2.3 or 4, n represents the number 0.1 or 2, 1], q represents the number 2, 3.4 or 5, respectively). The present invention relates to novel triazole compounds.

(Prior Art) The fact that some l-lyazole compounds have activity as herbicides is known, for example, in West German Patent No. 213.
No. 2618, U.S. Pat. No. 4,280,831, JP-A-59-39880 and JP-A-60-1
It is described in Publication No. 00561.

(Problems to be Solved by the Invention) However, conventional triazole herbicides cause phytotoxicity to crops, and sufficient herbicidal effects cannot be obtained unless used in large quantities.
There was a need for the development of triazole-based compounds.

Therefore, the present invention provides a drug T! It exhibits almost no F (!
The purpose of the present invention is to provide a triazole compound that exhibits a strong herbicidal effect against broad-leaved weeds such as Japanese cypress, azalea, horsetail, and cyperus, and against weeds of the Cyperaceae family, such as firefly and cyperus.

(Means for Solving the Problems) The compound of the present invention is a novel compound represented by the above formula 1 and having a structure different from conventionally known triazole compounds in the part of symbol A. The creation of the monster of the present invention is carried out, for example, as follows. As a starting material, a compound represented by the following formula ■: (wherein A and +1 have the above-mentioned meanings) is added to a compound represented by the following formula: (wherein Y, R, and R2 have the above-mentioned meanings). A compound of the formula -a is obtained by reacting the compound and optionally oxidizing with a suitable oxidizing agent.

In the above reaction, the target compound (■) is a sulfinyl compound (n=1) or a sulfonyl compound (n
= 2), a compound of formula (1) in which the S moiety is similarly oxidized may be used as a starting material, or alternatively, a compound of formula I in which S is unoxidized is first prepared, and if necessary, This may be oxidized. The step of reacting oxidized or unoxidized compound (1) with compound (2) is performed by reacting 1 to 2 equivalents of compound H in an appropriate solvent in the presence of a deoxidizing agent of 1 equivalent or more, preferably 1 to 2 equivalents. , preferably 1 to 1.2 equivalents of compound (2) are reacted. The reaction temperature is 0 to 100°C, preferably 20°C.
~70°C is suitable. Here, deoxidizing agents include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, and sodium hydride; organic bases such as triethylamine and pyridine; and solvents include carbonized bases such as benzene, toluene, and xylene. Hydrogen type, halogenated hydrocarbon type such as methylene chloride and chloroform, ether type such as diethyl ether, tetrahydrofuran and dioxane, getone type such as acetone and methyl ethyl ketone,
Other solvents such as acetic acid ethyl ester, acetonitrile, dimethylformamide, lysine, dimethyl sulfoxide, water, or a suitable mixed solvent thereof can be used.

Further, the oxidation step can be performed, for example, by oxidizing with an oxidizing agent in a suitable solvent.

The oxidizing agents used here include hydrogen peroxide, potassium permanganate, inorganic oxidizing agents such as chromic acid, peracetic acid, m
-Organic oxidizing agents such as chloroperbenzoic acid can be mentioned, and examples of the solvent used in this case include methylene chloride, chloroform, acetone, acetic acid, water, etc., or warm solvents thereof. The reaction temperature is suitably 0 to 50°C, but depending on the type of solvent or the progress of the reaction, heating or cooling can be performed as appropriate.

The starting compounds of formula (1) are novel per se, except those in which 8 represents an unsubstituted phenyl, nitrophenyl, nitroaminophenyl, dinitrophenyl, diaminophenyl and aminophenyl group. , forming part of the present invention. In order to produce this compound (1), for example, a compound of the following formula (1) and 13-<2-chloro-4-trifluoro is added to a compound of the formula: A -Z (wherein A has the above meaning). and Z represents a halogen atom) is reacted in an appropriate solvent. Also, to the compound -N
It can also be obtained by dissolving 112 in concentrated hydrochloric acid, adding NaNO2 and using it as a diazonium salt solution, and adding compound (2) therein.

The solvent used here may be any solvent as long as it is inert to the reaction components, and for example, those described above such as dimethylformamide can be used.

The reaction temperature is 20 to 2 when using Katani A-Z.
00°C, preferably 50 to 150°C, and compound A
-NH2 When using H2, the temperature is 0 to 100°C, preferably 0 to 70°C.

The present invention will be explained in more detail with reference to Examples below.

The following Examples 1 to 6 show the starting compounds of the invention represented by formula 9! ! This is an example regarding the method of sending.

Add 80 g of the sodium salt of 3-mercapto-1,2,4-t-lyazole to 150 dimethylformamide. This suspension contains 3,4-dichlorobencitrifluoride 1011? was added, and the mixture was stirred and reacted for 25 hours under continuous flow. After cooling, when 500 J of water is added to the reaction solution, an oily substance separates. This oil is extracted with ethyl acetate, and the extract is washed successively with N hydrochloric acid, water, 5 Sl≦aqueous sodium bicarbonate, and water, and then dried over magnesium sulfate. When the solvent is distilled off, an oil remains. Purified by silica gel chromatography (solvent: chloroform), 3-(2-
Chlor-4-trifluorophenylthio)-1,2,4
-)-Riazole crystals ss, ay are obtained.

Yield: 44.5 $, melting point: 109-110.5°C.

Elemental analysis value (%): C,ll5Cj!F,N,5 (814279,8f3)
As CIt N Calculated value 38.65 1.80 15.03 Analyzed value 3
8.55 1.20 15.02CsllsCj! F+
CIIN as N3N35 (21f, 674) Calculated value 45.39 2.86 19.85 Analysis value 4
5.43 2.72 19.73 Dissolve 3.8 g of 1-chloroaniline in 5 companies' concentrated hydrochloric acid and 5 g of crushed ice, and heat to 0°
Under cooling at C, 2.2. 5 aqueous solutions of sodium nitrite are added gradually at a rate not exceeding 4°C. Add this solution to 4
．． A solution of 5 g of potassium salt of 3-mercap 1--1.2.
℃ and stirred for an additional 30 minutes at the same temperature.

After cooling, the product is extracted with chloroform, washed with water and dried over magnesium sulfate. The solvent is distilled off, and the remaining oil is purified by silica gel chromatography (elution solvent: chloroform) to obtain 4.3 g of an oil. Yield: 68
%.

HN M R (CD C M) δ near, 2 to 7. (3(4
11, m), 8.8 (III, s), 12.0 (I
II, br, s) Elemental analysis value (%).

3g of acetone 3-(2-chloro-4-trifluoromethylphenylthio)-1,2,4-)riazole 3'
200mj of 2N-sulfuric acid in solution from 00 companies! Add. 2
While maintaining the temperature at 5° C. or lower, 40 y of a saturated aqueous solution of potassium permanganate is added dropwise to react.

After the addition, the mixture was further stirred at room temperature for 2 hours, and then a saturated aqueous solution of sodium bisulfite was added until the solution became colorless.

The generated crystals are collected and dried.

Recrystallization from ethyl acetate yields 21.3 g of white crystals. Yield: 54.6 $, melting point 222-223.5°C.

Elemental analysis value (%): c, II, CtlF3N, O□S (14M 311.6
8) as CII N calculation 1st shift 34.68 1.82 13.4
8 analysis value 34,90 1.72 13.61: iJ4
M±3 (7A:L 1 2 4 h') azole 3-amino-1,2,4-triazole 12g at 40%
Dissolved in sulfuric acid 26, and while keeping the temperature below 5°C, a solution of 11.9 g of sodium sulfite dissolved in 36 ml of water was added dropwise. The pH is then adjusted to 4-5 by adding saturated aqueous sodium acetate solution. This solution was mixed with thiophenol 11.
6ml, sodium hydroxide 4.72g and water 30+*
Add to the solution consisting of 1 over 1.5 hours under water cooling. After another 0.5 hours of stirring at room temperature and 1.5 hours of stirring at 40-50°C, the product was extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and the solvent was distilled off to form an oil. Things remain. This is purified by silica gel chromatography (solvent: chloroform-2% methanol) to obtain 12.88 g of an oil. Yield: 642 inches.

1-1- NMR data (CDCf3) δ near, 0 to 7.5 (511, m>, 7.90 (111,
s), 13.1 (ill, br, s) elemental analysis value (%)
: C, Il, N, 5 (814177,234> as CI
I N Calculated value 54.22 3.98 23.71 Analysis value 5
4.38 3.78 23. [Immerse a 39,200 ml flask in a water bath and add 5 mt' of (P4 hydrochloric acid and 20 g of crushed ice. While stirring, add 3.6.-2.
．． Add 6-dimethylaniline slowly. The mixture was cooled to 0°C and 2.2g of sodium nitrite was added at 51°C.
A cold solution of 111 in water is added at such a rate as to keep the temperature below 4°C.

On the other hand, a solution of 4.5FI potassium salt of 3-mercaptotriazole in 50n+1 water at 40-50°C is prepared, and the solution of the diazonium salt prepared earlier is added to this solution through a dropping funnel. This mixture was then diluted with 3 more
After stirring at 50-60° C. for 0 minutes and returning to room temperature, the organic layer is extracted with chloroform, washed with water, and dried over magnesium sulfate. The solvent is distilled off, and the remaining recrystallization is recrystallized from ethyl acetate-n-hexane. Melting point: 126-7°C. Collection
14.49 (F! Near 1%).

Elemental analysis value (%): Cl0I+,, CH'N as N5S (814205,288> Calculated value 58.5+ 5.40 20.47 Analysis value
l1i8.40 5.51 20.563-(2-methyl-6-ethylphenylthio)1.2.4-triazole zt, 9y in vinegar! ! ! Dissolve to 120 ml and heat to 70°C with stirring. Add this to 50ml of 35% hydrogen peroxide solution
was added dropwise, and after completion of the addition, stirring was continued at 100°C for 3 hours. Thereafter, it was left to stand overnight at room temperature, and the precipitated crystals were washed with P. Yield 1
(yield near 2%), reconsolidated with ethyl acetate, melting point 180~
181°C0 elemental analysis value (%): Cl +lI+ Jz02S (Ml'1251.31>
CHN Calculated value 52,57 5.21 16.72 Analysis value 5
2.61 5.18 16.60 Examples 7 to 13
is an example of the method for producing the final compound of the invention.

Preparation of Ru (Compound No. (67)) 3-(2-nitrophenylthio)-1,2,4-)riazole 411 and diethylcarbamoyl chloride 2
．． Dissolve 71g in acetone (Oml) and add carbonic acid.
Add 5.5 g of x and react for 5 hours under stirring and reflux.

After cooling, 100 ml of water was added to the reaction solution, and the target product precipitated out in the form of crystals. After drying, acetic acid ethyl ester-
Recrystallization from 〇-hexane gives the title 1-(diethylcarbamoyl)-3-(2-nitrophenylthio)-1,
5.08 g of 2,1-triazole are obtained. Yield: 8
7.8L? 11 points: 101-103°C.

Elemental analysis value (%); CII N Calculated value as CICl31115NSO3S (321,37) 48.59 4.71 21.86 Analysis value 4
8.41 4.65 21.7215 Lalal. yield,
92.5g, M point 105.5-107°C.

Elemental analysis value (%): C,, 11,, CIF, N, 0. S (M 410.82
) as CII N Calculated value 35.08 3.44 13.64 Analyzed value 3
5.15 3.41 13.58 (20)) Production of 3-(2-chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-1-riazole 3.12 g
and 1.62 g of diethylcarbamoyl chloride were dissolved in 10 ml of pyridine and reacted at 50°C for 5 hours. After the reaction is completed, 50 ml of water is added to the reaction solution, and the product is extracted twice with 100 ml of ethyl acetate. Ethyl acetate with N
- Washing with hydrochloric acid and then water, drying over magnesium sulfate, and concentrating to give crystals. Recrystallized from benzene-〇-hexane to obtain the title 1-(diethylcarbamoyl)
-3(2-chloro-4-trifluoromethylphenylsul)onyl)-1,2,4-triazole3. SO,,
(65)) Production of 1-(diethylcarbamoyl)-3-(2-chloro-4
-trifluoromethylphenylthio)1.2.4-) 3.7h of lyazole in 100ml of chloroform! 1.739 m-chloroperbenzoic acid was added little by little over 10 minutes while keeping the temperature below 10°C with ice water, and the mixture was further reacted at 10°C for 2 hours and at room temperature for 10 hours. The chloroform solution was washed twice with 100 ml of a 10% aqueous potassium carbonate solution and then with water, dried over magnesium sulfate, and the solvent was distilled off, leaving an oily substance. This oil was purified by silica gel chromatography (solvent: chloroform-rhexane 1:1).
) to obtain the title 1-(diethylcarbamoyl)3
2.73 of -(2-chloro-4-trifluoromethylphenylsulfinyl)-1,2,4-triazole are obtained as an oil. Yield: 68.4$ Elemental analysis value (%): c, 4++, , CIF, N, O□5 (814394
,815) as CII N Calculated value 42.59 3.57 14.19 Analysis value 4
2.71 3.46 14.30 No. (20)) Production of 1-(diethylcarbamoyl)-3-(2-chloro-4
-trifluoromethylphenylthio)=1 2.4-1
- Dissolve 3.79 g of Riazole in chloroform 100 and add 5y of 111-chloroperbenzoic acid little by little while keeping the temperature below 10°C with ice water.

The reaction is carried out by heating at 10°C for 2 hours, at room temperature for 10 hours, and then at 50°C for 2 hours. The chloroform solution is washed twice with a 10% aqueous potassium carbonate solution, dried over magnesium sulfate, and the solvent is distilled off to obtain crystals. benzene-11
- recrystallized from hexane to give the title 1-(diethylcarbamoyl)-3-(2chloro-4-trifluoromethylphenylsulfonyl)-1,2,4-)riazole 3.
．． Obtain 50g.

Yield: 85.2$, melting point 105.5-107°C.

-Production of (compound number (1)) 3-(2,6-dimethylphenylthio)-1,2,4-
)-2 g of lyazole are dissolved in 50 ml of pyridine, and 1.4 g of diethylcarbamoyl chloride is added dropwise to this solution. After stirring for 1 hour at room temperature and 2 hours at 70°C, pyridine is distilled off. The residue was extracted with chloroform and dried over magnesium sulfate to give 1-(diethylcarbamoyl)-
3-(2,6-dimethylphenylthio)-1,2,4-
A product of triazole is obtained. Cool this to 0℃ and
g m-ri roll overvalue 6. Add aromatic acid and stir at room temperature for 4 hours and 1 m.

The product is then washed with a 10% aqueous potassium carbonate solution, dried over magnesium sulfate, and recrystallized from ethyl n-hexane acetate under evaporated flame. Melting point = 111~2℃,
Yield: 2.4y (yield near 2%).

Elemental analysis value (%): CHN as C, 511□, N, O, S (MW 336.408) Calculated value 53.56 5.99 16.65 Analysis value 5
3.41 5.85 16.70 No. (187)) Preparation of 3-(2,4,5-1-limethyl-6-methoxyphenylthio)-1,2,4-triazole 2.51? 6゜m
Dissolve Z in pyridine, and dropwise add 1.49 g of diethylcarbamoyl chloride. 1 hour at room temperature, 70
After stirring for 2 hours at °C, the pyridine is distilled off. The residue was extracted with chloroform and dried over HH magnesium to give 1-(
A crude product of diethylcarbamoyl)-3(2,4,5-trimethyl-6-methoxyphenylthio)-1,2,4-triazole is obtained. This was cooled to 0°C, and 4g of [auto-chloride]5. Add aromatic acid and leave at room temperature for 2 hours, then 60
Stir at 'C for 2 hours. The product is then washed with a 10% aqueous potassium carbonate solution, dried over magnesium sulfate, the solvent is distilled off, and then recrystallized from 11-hexane-ethyl acetate. Yield: 2.6g (yield near 4%) Melting point: 138-9
℃.

Elemental analysis value (%): CIf N Calculated value as C, 71121N, 02S (M14348.471) 58.60 6.94 16.08 Analysis value 5
8.52 6.90 15.95 sword 1 3-(2-methyl-6-ethylphenylsulfonyl)-
25.1 g of 1,2,4-triazole and 14 g of diethylcarbamoyl chloride were dissolved in 20 (1 MF) acetone, 14 y of potassium carbonate was added, and the mixture was stirred and refluxed for 3 hours. After the reaction was completed, the precipitate was separated, and the mother liquor was concentrated. A crude product of the desired product is obtained. This product is purified by silica gel chromatography (n-hexane-ethyl acetate) to obtain an oily desired product.

NMR, δ: 1.10 to 1.41 (911, 11+
), 2.67(31(,s), 3.12(211,
q), 3.48 (411, q), 7.02-7.4
5 (in 311, +), 8.72 (111, s) - This oil becomes crystals when left in a cold place, and reconsolidates with I + hexane-ethyl acetate (1,:1) to give a melting point of 82-83.
℃.

Elemental analysis value (%): C+ aHz2N, 0*S (MW 350.44>)
-Cite CII N Calculated value 54.84 6.33 15.99 Analysis value 5
4.91 6.25 15.82 General 2 I in the following table 1
The compound was similarly synthesized from the corresponding starting materials.

The compound of the present invention can be used as a herbicide for weeding water, fields, orchards, etc., or non-agricultural land.

The timing of its use can be selected as appropriate, such as before crop sowing, at the time of seeding, at the time of transplantation, seedling stage, and growing season, and the method of use can be selected as appropriate from among water surface treatment, soil treatment, soil mixing treatment, foliage treatment, etc. be able to.

When actually using the compound of the present invention, solids used in the preparation of general agricultural chemicals,
It can be mixed with various liquid carriers to produce wettable powders, emulsions, oils, powders, granules, flowables, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, spreading agents, wetting agents, adsorbents, thickeners, 11v foaming agents, and antifreeze agents may be added to the drug.

The carrier referred to herein may be either solid or liquid, or a combination thereof. Examples include talc, clay, bentonite, kaolin, diatomaceous earth, calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene, cyclohexane,
Methylnaphthalene, benzene, acetone, dimethylformamide.

Examples include glycol ether and N-methylpyrrolidone.

Examples of the adjuvant include polyoxyenalene alkylphenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfone Pi salt, sorbitan ester, soaps, sulfated oils, alkyl sulfate ester salts, Petroleum sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonic acids, aliphatic amine salts, quaternary
class ammonium salts, alkylpyridinium l-salts,
Examples include alkyl dimethyl betaine, alkylaminoethyl glycine, polyglycol sulfate, alkylamine sulfonic acid, isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose, ethylene glycol, and xanthan gum.

In formulation, the mixing ratio of the monster of the present invention can be freely selected within the range of 0.05X to 951% by weight, but preferably 1 to 70%. 5 carrier 70-99%, preferably 40-90%
, formulations containing 0 to 20%, preferably 1 to 7% of adjuvants are preferred. In addition, a wider range of effects can be expected by mixing with other fungicides, herbicides, plant growth regulators, insecticides, acaricides, and other agricultural chemicals, fertilizers, and the like.

When actually using the compound of the present invention, it is necessary to appropriately select the amount used depending on the time of use), weather conditions, method of use, dosage form, place of use, target weeds, target crops, etc. As will be clear to those skilled in the art, the dosage used is generally between 5 and 500 per 10 ares of the compound of the present invention.
g, preferably 10 to 200 ft per 10 are.

Next, the usefulness of the compounds of the present invention as herbicides will be explained using test examples.

Trial@Example 1 Fill a 115,000 are Wagnerbot with paddy soil (planting soil), add 3 liters of water, and plow through the water.
Seeds of Aspergillus japonica, broad-leaved weeds (Azaena, Apsyllium, Kikashigusa, and Japanese chickweed) and Firefly were sown, and tubers of Cyperus japonica were placed on the surface, and then three rice plants at the two-leaf stage were planted at a depth of 2cn.

The chemical treatment was carried out by manually scattering prescribed violets of granules obtained in accordance with Preparation Example 1 described later on the water surface at the time of germination of wild plants. Management 5 Cultivation is carried out in a greenhouse, and the drug treatment f'Jl! After 4 weeks, the herbicidal effect and phytotoxicity of rice were investigated. The results are shown in Table 2.

The numerical values in the table indicate the herbicidal effect and the chemical damage to the test crops, and are specifically as follows.

Numerical value Weeding effect Crop damage 5 100
% control (Weed Fi 0% Death 4 80% control (Weed amount 20% Severe damage 3 60% control (Weed amount 40%)
Nakayoshi 2 40% control (weed amount 60%) Low damage l
2096 control (weed amount 80%, slight damage 0)
(B≦Control (weed amount 100%) Harmless In addition, the following compounds in Table 2 were used as control compounds for comparison: Ratio 1!2I (See US Pat. No. 4,280,831) Comparison Reference) Comparison■ (Refer to JP-A No. 59-39880) Comparison ■Refer to No. 39880) Comparison VRefer to No. 77030) Table 3 Test @ Example 2 A 115,000 are Wagner pot was filled with paddy soil (planting soil). , add water and scrape,
Seeds of aspergillus and broad-leafed weeds (Azeena, Japanese aphrodisiac, Kikashigusa, and Lythrum) were sown, and 2c1 of rice was grown at the two-leaf stage.
Three plants were planted at a depth of 1. The water depth was 3 cm. To treat the chemical, at the 2nd leaf stage to 2.5th leaf stage of wildflowers, weigh out a predetermined amount of the wettable powder obtained according to Formulation Example 2 below, dilute it to 5 mZ of water per pot, and spray it on the water surface. did. The plants were managed and grown in a greenhouse, and 4 weeks after the chemical treatment, the herbicidal effect and chemical damage to rice were investigated. The results are shown in Table 3.

The meaning of the philtral value and the soft control compound are the same as those shown in Test Example 1.

Trial @ ('A3 A 115,000 are Wagnerbot was filled with field soil (planting soil), wheat and soybean seeds were sown, and the soil was covered with field soil containing weed seeds to a depth of 2 cm. After that. Immediately, a predetermined amount of the emulsion obtained according to Pillar Example 3 described below was weighed, diluted with 5 val of water per pot, and sprayed on the soil surface.Management and cultivation were carried out in a greenhouse, and 4 After a week, the herbicidal effect and phytotoxicity of wheat and soybean were investigated.

The results are shown in Table 4. The numerical values in Table 0 are the same as those shown in Test Example 1.

Table 4 Next, formulation examples of the herbicide of the present invention will be shown.

Formulation Example 11 Compound No. 2 1.5 parts by weight Sodium ligninsulfonate 2 parts by weight Bentonite
30 heavy wall talc 66.5
Parts by Weight These ingredients are thoroughly warmed until homogeneous and granulated to obtain granules.

Formulation Example 2 Sappakufu No. 20 50 parts by weight Sodium alkyl sulfate 2.5 parts by weight Polyoxyethylene alkyl phenyl ether 2.5 type Sobe clay
45 parts by weight These ingredients are thoroughly mixed until homogeneous and pulverized to obtain a wettable powder.

Formulation Example 3 Compound No. 6 20 parts by weight Alkylbenzene sulfonate: (parts by weight Polyoxyethylene alkylaryl ether 10 parts by weight Kijirol 671R) These ingredients are mixed well until homogeneous and dissolved to obtain an emulsion. .

Claims (1)

[Claims] 1. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 and R_2 are the same or different,
It represents a lower alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, or R_1 and R_2 together with the nitrogen atom to which they are bonded represent an azacycloalkane having 4 to 6 carbon atoms, and A is the following formula: ▲Formula , chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Represents the group ▼ where X is a hydrogen atom or a lower alkyl group that may be substituted with a hydroxyl group, a cycloalkyl group, or an alkoxy group , an alkoxycarbonyl group, an alkylcarbonyl group, a phenoxy group, a benzyl group, an α-hydroxybenzyl group, a halogen, a nitro group, an amino group, or a trifluoromethyl group, and R_3 represents a hydrogen atom or a lower alkoxy group. m represents the number 0, 1, 2, 3 or 4, and n is 0
, represents the number 1 or 2, and p and q are 2, 3, and 4, respectively.
Or represents the number 5. ) A triazole compound represented by 2. General formulas: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, A is the following formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Represents a group of R_3 represents a hydrogen atom or a lower alkoxy group. and n represents the number 0, 1, 2, 3 or 4, n represents the number 0, 1 or 2, p,
q represents the number 2, 3, 4 or 5, respectively. ) Compound represented by. 3. General formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, A and n represent the meanings given in claim 1.) The compound represented by the following formula: ▲ Mathematical formula , chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 represent the meanings given in claim 1, and Y represents a halogen.) The compounds shown in the formula are reacted, and if necessary, the product is General formulas characterized by oxidizing: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (wherein A, R_1, R_2 and n represent the meanings given in claim 1). ) A method for producing a triazole compound represented by 4. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, A, n, R_1 and R_2 represent the meaning given in claim 1.) Triazole compound represented by A herbicide composition containing as an active ingredient.