JPH0495091A - Indazole sulfonamide derivative, its production and herbicide containing the derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R<1> is H or lower alkyl; R<2> is H, lower alkyl(thio), lower (halo)alkyl, lower alkynyloxy, halogen or (halogen- substituted) phenoxy; X and Y are lower (halo)alkyl, lower (halo)alkoxy or halogen; Z is CH or N]. EXAMPLE:N-(1,3-dimethyl-indazol-4-ylsulfonyl)-N'-4(4,6-dimethoxypyrimi din-2-yl) urea. USE:A herbicide. PREPARATION:The objective compound can be produced by reacting a compound of formula II with a compound of formula III optionally in a solvent (e.g. hexane) and, as necessary, in the presence of a base (e.g. pyridine) at 20-40 deg.C for 1-1.5hr. The amount of the compound of formula III and the base is preferably 1-1.2 equivalent each based on 1 equivalent of the compound of formula II.

Description

[Detailed Description of the Invention] Industrial Application Fields The present invention provides novel indazole sulfonamide derivatives,
This article relates to the Br method and herbicide S containing it as an active ingredient.

<Prior Art> It has been known that a number of sulfonamide derivatives such as sulfometuron methyl are used as herbicides.

<5irii that the invention is about to pass> However,
These compounds may have insufficient herbicidal efficacy or
The selectivity of miscellaneous TL; ζ is inferior, so it cannot be said that Δ is necessarily satisfactory.Means for solving the problem> The present inventors have solved the above situation by As a result of investigation, it was discovered that a sulfonamide derivative having an indazole ring is an excellent herbicide that has high herbicidal activity at a low dose and does not cause any harmful effects on crop plants.The present invention has been made. reached.

That is, in the present invention, in the general formula c, R represents a hydrogen atom or a lower alkyl group,
R2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group,
Represents a lower alkylthio group, a halo-lower alkoxy group, a lower alkynyloxy group, a halogen atom, or a phenoxy group optionally substituted with a halogen atom,
are the same or different and represent a lower alkyl group, a lower alkoxy group, a halogen atom, a halo-lower alkyl group or a halo-lower alkoxy group, and represents ZIiCHl--N. ] An indazole sulfonamide derivative (hereinafter referred to as
This invention relates to the compound of the present invention), its production method, and herbicides containing it as an active ingredient.

First, the method 1ζ for producing the compound of the present invention will be explained.

(Manufacturing method 1) The compound of the present invention is a membrane bag [wherein R and R2 have the same meanings as above]. ] and -membrane bag [wherein X, Y and 2 represent the same meanings as above. ] It can be produced by reacting the compound shown below.

The reaction is usually carried out without solvent or with 1! Planning, necessary power °
)1 The amount of the reagent used in the reaction is 1 to 1.5 equivalents, preferably 1 to 1.5 equivalents of the compound represented by the general formula C1) per 1 equivalent of the compound represented by the general formula [C]. 2 equivalents, and the base is 1 to 1.5 equivalents, preferably 1 to 1.2 equivalents. Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether;
Aromatic hydrocarbons such as benzene, toluene, xylene,
Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene,
Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofradi, diethylene glycol dimethyl ether, methanol, ethanol,
Alcohol bases such as Impropatol, t-butanol, octatool, cyclohexanol, methyl cellosolve, diethylene glycol, and glycerin, ester necks such as ethyl acetate and butyl acetate, nitro compounds such as nitroethane and nitrobenzene, acetonitrile, and imbutylene. Examples include nitriles such as nitrile, amides such as formamide, N,N-dimethylformamide, and acetamide, and sulfur compounds such as dimethyl sulfoxide and sulfolane.

Examples of the base include pyridine, triethylamine, 1
．． 4-Diazabicyclo(2,2,2)octane, 1.5
-diazabicyclo(4,,3,0)non-5-ene, 1
．． Organic bases such as 5-diazabicyclo[5,4゜0]undec-5-ene, N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium Examples include alkali metal alkoxides such as methoxide and sodium ethoxide.

After the reaction is complete, pour the reaction solution into water to make it neutral to acidic.
The desired compound of the present invention can be obtained by filtering the precipitated crystals or subjecting them to conventional post-treatments such as organic solvent extraction and concentration.

Further, if necessary, it can be purified by operations such as chromatography and recrystallization.

(Manufacturing method 2) The compound of the present invention is a membrane bag [wherein R and R2 represent the above-mentioned QWt taste. ]
A compound represented by the general formula [wherein, X%Y and 2 represent the same meanings as above]. ] It can be produced by reacting with the compound shown below.

The reaction is usually carried out without a solvent or in a solvent, if necessary in the presence of a base, the reaction temperature ranges from -20 to 120°C, preferably 20 to 40°C, and the reaction time ranges from 0.5 to 24°C.
The reaction time is preferably 1 to 1.5 hours, and the amount of the reagent used in the reaction is 1 to 1.5 hours for the compound represented by membrane bag [IV] per 1 equivalent of the compound represented by general formula (V). 1.5 equivalents, preferably 1 to 1.2 equivalents, and the base is 1 to 1.5 equivalents, preferably 1 to 1.2 equivalents.

Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene. halogenated hydrocarbons such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol, isopropanol, t-butanol, octatool,
Alcohols such as cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, ethyl acetate,
Ester compounds such as butyl acetate, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, amides such as formamide, N,N-dimethylformamide, acedo, sulfur such as dimethyl sulfoxide and sulfolane. Examples include compounds.

Examples of the base include pyridine, triethylamine, 1
．． 4-DiazabicycloC2,2,2]octane, 1.5
-Diazabicyclo I: 4.8.0) non-5-ene, 1.5-diazabicyclo(5-4-0) undec-5
- Organic bases such as di-, N, N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc. can give.

After the reaction is complete, pour the reaction solution into water to make it neutral to acidic.
The desired compound of the present invention can be obtained by filtering the precipitated crystals or subjecting them to conventional post-treatments such as organic solvent extraction and concentration.

Further, if necessary, it can be purified by operations such as string chromatography and recrystallization.

(Manufacturing method 8) The compound of the present invention comprises - a compound represented by a membrane bag [1 piece], and -
In the membrane bag c formula, X, Y and 2 have the same meanings as above. ] It can be produced by reacting with the compound shown below.

The reaction is usually carried out without a solvent or in a solvent, if necessary in the presence of a base, and the reaction temperature ranges from 0 to 110°C, preferably from 25 to 50°C, and the reaction time ranges from 0.5 to 24°C.
The reaction time is preferably 1 to 1.5 hours, and the amount of the reagent used in the reaction is 1 to 1.5 hours for the compound represented by the general formula [VI] per 1 equivalent of the compound represented by the general formula [1]. 5 equivalents, preferably 1 to 1.2 equivalents, base 1 to 1.5 equivalents,
Preferably it is 1 to 1.2 equivalents.

Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene. halogenated hydrocarbons such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol, isopropanol, t-butanol, octatool,
Alcohols such as cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, ethyl acetate,
Esters such as butyl acetate, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and imbutyronitrile, amides such as formamide, N,N-dimethylformamide and acedeamide, sulfur lambda compounds such as dimethyl sulfoxide and sulfolane etc. can be mentioned.

Examples of the base include pyridine, triethylamine, 1
．． 5-diazabicycloi" 5.4.0) undec-
Organic bases such as 5-ene, N, N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc. can be given.

After the reaction is complete, pour the reaction solution into water to make it neutral to acidic.
The desired compound of the present invention can be obtained by filtering the precipitated crystals or subjecting them to conventional post-treatments such as organic solvent extraction and concentration.

Further, if necessary, it can be purified by operations such as chromatography and recrystallization.

The incyanate conductor represented by the general formula [VI] used in this reaction is disclosed in Swiss Patent No. 5.790.
No. 62, United States Patent Division No. 3,919°228,
U.S. Pat. No. 3.732.221 and Ang.
evt, chem, Mt, Ed, 10.40
2 (1976).

(II Production Method 4 The compound of the present invention is produced by reacting the compound represented by -membrane bag c in formula 81 and R2 have the same meanings as above) with the compound represented by general formula [■] You can.

The reaction is usually carried out without a solvent or in a solvent, if necessary in the presence of a base, the reaction temperature ranges from 0 to 110°C, preferably 25 to 50°C, and the reaction time ranges from 0.5 to 24 hours. Preferably for 1 to 1.5 hours, the hardware is 1 to 1.5 equivalents,
Preferably it is 1 to 1.2 equivalents, and the base is 1 to 1.5 equivalents, preferably 1 to 1.2 equivalents.

Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene. halogenated hydrocarbons such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, methanol, ethanol, isopropanol, t-butanol, octatool,
Alcohols such as cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, ethyl acetate,
Esters such as butyl acetate, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, amides such as formamide, N,N-dimethylformamide, acedo, sulfur such as dimethyl sulfoxide and sulfolane. Examples include compounds.

Examples of the base include pyridine, triethylamine, 1
．． Organic bases such as 5-diazabicyclo[5,4,OEundec-5-ene, N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, sodium methoxy and alkali metal alkoxides such as sodium ethoxide.

After the reaction is completed, the reaction solution is poured into water (neutral to acidic), and the precipitated crystals are filtered or subjected to conventional post-treatments such as organic SaC extraction and concentration to obtain the desired compound of the present invention. I can do it.

Further, it can be purified from the required lζ by operations such as chromatography and recrystallization.

(Production method 5) Among the compounds of the present invention, -membrane bag [In the formula, R represents a lower alkyl group, Yl represents a chlorine atom or OR'', and R1, R2, and 2 represent the same meanings as above.] The sulfonamide derivative is -membrane bag [wherein R
1, R2 and 2 have the same meanings as above. [In the formula, M represents an alkali metal and R3 has the same meaning as above. ] It can be produced by reacting with the compound shown below.

The reaction is usually carried out in a solvent, and the reaction temperature ranges from 1 to 1.
The temperature is 0 to 80°C, preferably 25 to 80°C, the reaction time ranges from 0.5 to 24 hours, preferably 4 to 6 hours, and the amount of reagent used in the reaction is determined by the general formula [DD]. The amount of the compound represented by the general formula [X) is 2 equivalents or more per 1 equivalent of the sulfonamide island conductor.

Examples of the solvent used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, and petroleum ether, benzene, aromatic hydrocarbons such as luene and xylene, chloroform, carbon tetrachloride, dichloroethane, Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and diethylene glycol dimethyl ether, nitro compounds such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, formamide, N, N-
Examples include amides such as dimethylformamide and acetamide, and sulfur compounds such as dimethyl sulfoxide and sulfolane.

After the reaction is complete, pour the reaction solution into water to make it neutral to acidic.
The desired compound of the present invention can be obtained by filtering the precipitated crystals or subjecting them to conventional post-treatments such as organic solvent extraction and concentration. Further, if necessary, it can be purified by operations such as chromatography and recrystallization.

Table 1 shows some of the compounds of the present invention produced according to the above production method.

Table 1: 2 Compounds represented by the general formula (phantom), which are raw material compounds for producing the compounds of the present invention, can be produced, for example, by the following route.

Ho-81 In formula C, 14 and R represent a halogen atom, and R1 and R2 have the same meanings as above. ] Furthermore, the compound represented by general membrane bag ff) can be produced by the following reaction.

In addition, the compound represented by -membrane bag [Higashi] can be produced by one of the following reactions.

The compound of the present invention can be used to treat wet weeds that are problematic in foliar and soil treatments in fields, such as purslane, chickweed, whiteweed, blueberry, buckwheat, and Japanese knotweed.
Japanese radish, Japanese radish, shepherd's purse, American hornwort, Japanese radish, Japanese radish, Japanese goldenrod, field pansies, Japanese morning glory, Japanese morning glory, European bindweed, Japanese radish, hotokenoza, white-spotted morning glory, Japanese Physalis, Japanese giant pufferfish, Japanese fir, sunflower, dog chamomile,
Broad-leaved weeds such as corn marigolds, barnyard grass, and barnyard grass,
The compound of the present invention has a herbicidal effect on grasses of the Poaceae family, such as hackberry grass, grasshopper, grasshopper, grasshopper, oat, oat, Seiban sorghum, grasshopper, blackberry grass, grasshopper, and goldenrod. It does not cause any harmful effects on major crops such as wheat, barley, rice, soybean, cotton, and sugar beet.

In addition, the compound of the present invention can be used to control mild weeds that are problematic in the flooding treatment of rice fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, japonica, and chickweed, as well as cypress cyperus, scallops, sycamore, and cypress japonica. It has a herbicidal effect against weeds of the Cyperaceae family, Cyperaceae, Cyperaceae, etc., and does not cause any harmful effects on rice.

When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, 11-grain wettable powders, and the like.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.01 to 90%, preferably 0.05 to 80%.

As solid carriers, fine powders or granules such as kaolin clay, tabalgite clay bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, analite, kuru 2 shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide are used. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, and vegetable oils such as soybean oil and cottonseed oil. , dimethyl sulfoxide, N,
Examples include N-dimethylformamide, acetonitrile, water and the like.

Surfactants used for emulsification, dispersion, wet layering, etc. include alkyl iut ester salts, alkyl sulfonates, and alkylaryl sulfone salts.

Anionic surfactants such as dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid esters, poly Examples include nonionic surfactants such as oxyethylene sorbitan fatty acid ester.

As formulation adjuvants, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC
(carboxymethyl cellulose), PAP (m-isopropyl phosphate), and the like.

The compound of the present invention is usually formulated and treated with earthen walls, foliage, or waterlogging before or after the emergence of weeds. Soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes treatment from above the plant body, as well as local treatment that treats only weeds so that they do not attach to crops.

When using an uninvented compound as an active ingredient of a herbicide, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target weeds, target crops, etc., but usually 1.
lof to 50αOf per hectare, preferably 2
0f to 4000f, and emulsions, wettable powders, suspension agents, granule wettable powders, etc. are usually used at a prescribed amount of 10% per hectare.
0su.

The granules are diluted with 1000 liters of water (to which auxiliary agents such as spreading agents are added if necessary) and treated, and granules and the like are usually treated as they are without any dilution.

Examples of the spreading agent include, in addition to the above-mentioned surfactants, polyoxyethylene 411iI ester, lignidisulfonate, abietate, dinaphthylmethane disulfonate, paraffin, and the like.

Furthermore, the compound of the present invention can be used as a herbicide in rice fields, upland fields, fruit SV+, pastures, lawns, forests, non-agricultural lands, etc., and can also be used in combination with other herbicides to control weeds. It is expected that the efficacy will be increased. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.

<Examples> Next, the present invention will be described in more detail with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples.

First, a manufacturing example will be shown.

Production example 1.3-dimethyl-4-aminosulfonylisitasol 200M9 and 2-phenoxycarbonylamino-4,6
-Dissolve 270 Mg of cymethoxypyrimidine in anhydrous acetonitrile of 10-l,5-diazabicyclo-[5,
4,0]] Add 135"P of undecar 5-e at room temperature.
Stir for hours. Next, the 1ζ reaction solution was poured with water, acidified with dilute salt, and then extracted with chloroform. The resulting residue was subjected to thin layer chromatography (developing solvent: ethyl acetate:hexane=1) under reduced pressure.
:1) to give N-(1,3-dimethyl-indazole-(yield 60%).

Melting point: 148.8°C 121" Table 2 shows some of the compounds of the present invention produced according to the above production method.

Second! [- Next, a formulation example is shown. The compounds of the present invention are represented by the compound numbers in Table 2, and parts represent parts by weight.

Formulation Example 1 Compound (2) of the present invention, 50 parts each of lignin sulfoshishun calcium, 2 parts sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 5 parts each of the compounds (1), (2, (8), (4)) of the present invention,
Toxanone P13L■ (Sanyo Chemical Industries ■Toshusho II) 1
5 parts of cyclohexanone and 80 parts of cyclohexanone were thoroughly mixed to obtain an emulsion.

Formulation Example 3 Compounds of the present invention (1), (2 parts each of J, 2 parts of synthetic hydrated silicon 1'FA, 2 parts of calcicalcium lignosulfonate, 30 parts of tonite, and 65 parts of S kaolin clay were thoroughly ground and mixed, and water was added. After kneading the mixture thoroughly, the mixture is granulated and dried to obtain grain tips.

Formulation Example 4 25 parts each of the compounds (1) and (3) of the present invention, 8 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water were mixed and wet-pulverized until the particle size became 5 microns or less. Obtain a clouding agent.

Formulation Example 5 10 parts of the compound (2) of the present invention, 1 part of polyoxyethylene styrylphenyl ether, and 89 parts of water are mixed to obtain a liquid preparation.

Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. Note that the compound of the present invention is
The compounds used for comparison iζ are indicated by the compound numbers in Table 3.

Table 8 In addition, #herb efficacy and phytotoxicity are determined by visually observing the degree of budding and growth inhibition of test plants during the survey, and those with no or almost no difference from those in which no compound is tested are classified as "0".
'', and if the test plant is dead or its growth is completely inhibited, it is ``5'', and there are 6 stages from θ to 5! ζP value,
0,1.2.3.4.5.

Test Example 1 Field soil stem leaf treatment test diameter 1011. Field soil was filled in a cylindrical plastic pot with a depth of IIMII, and barnyard grass, radish, Japanese radish, and Japanese morning glory were kept at a layer temperature and grown in a greenhouse for 8 days. Thereafter, the test compound was made into an emulsion Jζ according to Formulation Example 2, a predetermined amount of it was diluted with water containing a spreading agent equivalent to 10 liters per are, and the entire stem and leaf area was coated from the upper part of the plant using an automatic injector. was uniformly treated with Sζ.

After treatment, the plants were grown indoors for 19 days and their herbicidal efficacy was investigated.

The results are shown in Table 4.

Table 4 Test Example 2 Paddy field flooding treatment test A cylindrical plasti kubot with a diameter of 8 ann and a depth of 12 was filled with paddy soil, and 1 to 2 pieces of Japanese millet and firefly were placed in it.
It was mixed to a depth of cI11. After flooding and creating a paddy field, tubers of Urikawa were buried at a depth of 1 to 2 cN1.
Grown in a greenhouse. After 6 days (early stage of occurrence of each vehicle), the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was added to 2.
It was diluted with 5 milliliters of water and applied to the water surface. After treatment, the plants were grown in a greenhouse for 19 days and their herbicidal efficacy was investigated. The results are shown in Table 1.

@5 table test example 3 Field soil layer treatment test surface @ a 3 x 23exs2, depth: ” 1151 (
7) Yes h IC field land was packed with ±1, layered with wheat, barley, chickweed, pansies, wildflowers, and foxtail, and covered with soil to a thickness of 1 to 23. The test compound was emulsified according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per area, and the mixture was uniformly treated over the entire earthen surface using an automatic grating machine. After treatment, the plants were grown in a greenhouse for 25 days and their herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 6.

Table 6 Test Example 4 Field soil, stem, and leaf treatment test surface 983X28a11. A vat with a depth of 113 cm was filled with field sand, and wheat, chickweed, stagweed, and staghorn grass were kept at a layer temperature and grown for 31 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water equivalent to 10 liters per are, and the emulsion was uniformly applied to the entire stem and leaf area from the top of the plant using an automatic sprayer. At this time, the growth conditions of weeds and crops vary depending on the grass, but they are in the 1-4 leaf stage and the plant height is 8-25 cm! It was 11. Herbicidal efficacy and phytotoxicity were investigated 25 days after treatment. The results are shown in Table 7. Note that this test was conducted in a greenhouse throughout the entire period.

Table 7 Test Example 5 Paddy field flooding treatment test A 115,000 are Wagner pot was filled with paddy soil, and seeds of Japanese millet and broad-leaved weeds (Azeena, Azalea, Lythium chickweed, Japanese Lythrum) were mixed in at a depth of 1 to 2 m. After flooding the rice field and making it into a paddy field, tubers of Cyperus spp. 11 days later (Tainubie's 2
During the leaf stage, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with IOE liter of water and applied to the water surface to a water depth of 4 crn. After treatment, the plants were grown in a greenhouse for 20 days, and their herbicidal efficacy and phytotoxicity were investigated. The results are shown in the 8th section.
Shown in the table. In this test, water leakage was performed in an amount equivalent to a water depth of 8 cIn per day for two days from the day after the treatment.

Table 8 <Effects of the Invention> The compounds of the present invention have excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment of upland fields, as well as in flooding treatment of paddy fields, and have excellent herbicidal efficacy against various weeds that are problematic in soil treatment and foliage treatment in upland fields, as well as in flooding treatment of rice fields. Since it exhibits excellent selectivity for herbicides, it can be used in a variety of applications as an active ingredient in herbicides.

Claims (3)

[Claims] (1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents a hydrogen atom or a lower alkyl group, and R^2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group. , represents a halo-lower alkoxy group, a lower alkynyloxy group, a halogen atom or a phenoxy group optionally substituted with a halogen atom, X and Y are the same or different, and a lower alkyl group, a lower alkoxy group, a halogen atom, a halo-lower It represents an alkyl group or a halo-lower alkoxy group, and Z represents CH or N. ] An intazole sulfonamide derivative represented by (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 represents a hydrogen atom or a lower alkyl group, and R^2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group. , represents a halo-lower alkoxy group, a lower alkynyloxy group, a halogen atom, or a phenoxy group optionally substituted with a halogen atom. ] There are compounds represented by the general formula ▲ mathematical formulas, chemical formulas, tables, etc. represents an alkoxy group, Z is CH
Or represents N. The method for producing an intazole sulfonamide derivative according to claim 1, which comprises reacting the intazole sulfonamide derivative with a compound represented by the following. (3) A herbicide comprising the intazole sulfonamide derivative according to claim 1 as an active ingredient.