JPH0649676B2 - Sulfonamide compound - Google Patents

Description

TECHNICAL FIELD The present invention provides a novel sulfonamide compound useful as a herbicide and a fungicide, and a herbicide and a fungicide containing the sulfonamide compound as an active ingredient. Is.

(Problems to be Solved by Prior Art and Invention) Conventionally, many sulfonamide compounds have been synthesized. For example, U.S. Pat. (Wherein X represents a methyl group, a phenyl group, etc., and X'represents a hydrogen atom, an alkyl group), a method for producing the same, and the sulfonamide compound as a raw material for synthesizing a polymer compound. It has been described as useful. The compound represented by the general formula (A) is considered to be a styrene derivative having a functional group, and thus it can be easily analogized that it can be used as a raw material for synthesizing a polymer compound, but other applications, for example, as a medical or agricultural chemical The application and the like cannot be expected at all, and thus, until now, no research has been conducted on the physiological activity of the sulfonamide derivative represented by the general formula (A).

(Means for Solving Problems) The present inventors have studied a sulfonamide compound having a high herbicidal activity and safe for paddy rice and exhibiting so-called excellent selective herbicidal activity. As a result, certain sulfonamide compounds show high herbicidal activity in a wide range of grass species,
It was also confirmed that they can be excellent herbicides that are safe against rice, and that these compounds have strong antibacterial activity and can be excellent fungicides, and have completed the present invention.

That is, the present invention has the general formula (1) [Wherein R is a substituted or unsubstituted phenyl group, a naphthyl group, a heteroaryl group having 3 to 9 carbon atoms or an alkyl group containing a 5- or 6-membered ring having sulfur, oxygen or nitrogen as a hetero atom] Therefore, the substituent is selected from a halogen atom, a cyano group, a nitro group, an alkylamino group, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylthio group and a haloalkyl group.

R ¹ and R ² are the same or different hydrogen atoms or alkyl groups.

R ³ is a hydrogen atom, or a substituted or unsubstituted phenyl group, phenylalkyl group, heteroarylalkyl group (the heteroaryl group is the same as R), an alkyl group or an alkenyl group, and the substituent is a halogen atom. , Cyano group, nitro group, alkyl group, alkoxy group, alkenyloxy group, alkoxyalkyl group, haloalkyl group and alkylthio group.

R ⁴ each represents a haloalkyl group. ] And a herbicide and a fungicide containing the sulfonamide compound as an active ingredient.

In the present invention, in the above general formula (1), the substituted or unsubstituted phenyl group and naphthyl group represented by R are not particularly limited and may be used. When any one of the above groups has a substituent, the substituent is a halogen atom, a cyano group, a nitro group, an alkylamino group, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylthio group, a haloalkyl group, or the like. Specific examples of the halogen atom include chlorine, bromine, fluorine and iodine atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group and an n-butyl group. In addition, these alkyl groups may have a part or all of hydrogen substituted by a substituent such as a halogen atom, and specific examples thereof include chloromethyl group, bromomethyl group, fluoromethyl group, iodomethyl group, dichloromethyl group. Group, difluoromethyl group, trichloromethyl group, trifluoromethyl group, chloroethyl group, fluoroethyl group, dichloroethyl group, trifluoroethyl group, cyanomethyl group, hydroxymethyl group and the like. The alkoxy group is not particularly limited, but specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group and the like. Further, the alkylthio group is not particularly limited, but representative examples thereof include a methylthio group, an ethylthio group, an n-propylthio group and an iso-propylthio group. Further, specific examples of the alkylamino group include a methylamino group, a dimethylamino group, a diethylamino group and the like. Furthermore, the above alkoxy group is not particularly limited. To show a specific example,
Examples thereof include methoxymethyl group, methoxyethyl group, methoxypropyl group and ethoxymethyl group. The number of substituents of the substituted aryl group represented by R, R ³ and R ⁴ is preferably 1 to 3 from the viewpoint of easy availability of raw materials. When the number of substituents is plural, the substituents may be the same or different from each other.

In the general formula (1), among the groups represented by R, the heteroaryl group is a heteroaryl group having a carbon number of 3 to 9 and containing a 5- or 6-membered ring having sulfur, oxygen or nitrogen as a hetero atom ( Hereinafter, this may be simply referred to as “heteroaryl group” and may be used with or without further substituents without particular limitation. Specific examples of the unsubstituted heteroaryl group include furyl group, thienyl group, pyrrolyl group, pyridyl group, benzofuryl group, benzothienyl group,
Examples thereof include indolyl group, quinolyl group, and pyrazolyl group. Further, as the kind and the number of the substituents of the above-mentioned substituted heteroaryl group, the kind and the number of the substituents exemplified in the above-mentioned substituted aryl group are similarly adopted.

R ¹ and R ² in the general formula (1) are the same or different hydrogen or alkyl groups.

R ³ is a hydrogen atom or a substituted or unsubstituted phenyl group, phenylalkyl group, heteroaryl group (comprising sulfur or oxygen as a hetero atom), an alkyl group or an alkenyl group, and these groups are present in these groups. As the substituent which may be present, a halogen atom, a cyano group, a nitro group, an alkyl group, an alkoxy group, an alkenyloxy group,
It is selected from an alkoxyalkyl group, a haloalkyl group, an alkylthio group and the like.

In the general formula (1), the alkyl groups represented by R, R ¹ , R ² and R ³ are not particularly limited, and straight-chain or branched alkyl groups are used. The number of carbon atoms is not particularly limited, but is preferably 1 to 6 from the viewpoint of easy availability of raw materials. Specific examples of the alkyl group are methyl group, ethyl group, n
-Propyl group, iso-propyl group, n-butyl group, n-
A hexyl group and the like can be mentioned. As the substituted alkyl group represented by R and R ³ , all or part of hydrogen in the above-mentioned unsubstituted alkyl group is a halogen atom, an alkoxy group, an alkylthio group, a cyano group, an alkenyl group, an alkenyloxy group. Those substituted with an aryl group, a heteroaryl group, or the like are preferable. Specific examples of such a substituted alkyl group include chloromethyl group, bromomethyl group, fluoromethyl group, iodomethyl group, dichloromethyl group, chlorodifluoromethyl group, difluoromethyl group, trichloromethyl group, trifluoromethyl group, chloroethyl group. Group, bromoethyl group, fluoroethyl group, dichloroethyl group, dibromoethyl group, difluoroethyl group, trichloroethyl group, trifluoroethyl group, perfluoroethyl group, perfluorobutyl group, perfluorohexyl group, methoxymethyl group, ethoxy Methyl group,
Methoxyethyl group, ethoxyethyl group, methoxypropyl group, allyloxyethyl group, methylthioethyl group, ethylthioethyl group, cyanomethyl group, cyanoethyl group,
Allyl group, allyloxyethyl group, phenylmethyl group,
Furylmethyl group, thienylmethyl group and the like can be mentioned,
In the case of an alkyl group substituted with an aryl or heteroaryl group, such as a phenylmethyl group, a furylmethyl group or a thienylmethyl group, the aryl or heteroaryl group may have a substituent and is represented by R and R ³ . The conditions of the substituent of the substituted phenyl group can be applied as they are.

Examples of the haloalkyl group represented by R ⁴ include those in which a part or all of the hydrogen atoms in the above-mentioned alkyl group are substituted with halogen atoms. The halogen atom is not particularly limited, but chlorine, bromine or fluorine is preferable.
Specific examples thereof include the haloalkyl groups exemplified as the substituted alkyl group.

The structure of the sulfonamide compound represented by the general formula (1) of the present invention can be confirmed by the following means.

(B) by measuring the infrared absorption spectrum (IR), based on a double bond of a vinyl group in 1600～1650Cm ^-1 absorption, 1370~1320cm ^-1 and 1180-11
At 50 cm ^-1 , absorption based on the sulfonyl bond of the sulfonamide group can be observed. As a typical example, N-
(2,2-Dimethyl-1-phenyl) ethenyl-N-
The infrared absorption spectrum of (2'-methoxyethyl) trifluoromethanesulfonamide is shown in FIG.

(B) Measure each mass spectrum (MS) and observe each
(Generally, sulfur molecular weight m is divided by ion charge number e)
(The number expressed in m / e)
And the molecular weight of the compound used for measurement and the molecule.
It is possible to know the bonding mode of each atomic group within. Immediately
Then, the sample used for the measurementIn general, the molecular ion peak (hereinafter M When
Abbreviated) is the number of halogen atoms contained in the molecule
Depending on the intensity ratio according to the isotope abundance ratio,
The molecular weight of the compound used for the measurement can be determined.
For the compound represented by the above general formula, M , M -R^Four, M -SO₂R^Four，R³ The characteristic peaks corresponding to
You can know the binding mode of.

By measuring the (c) ¹ H- nuclear magnetic resonance spectra ⁽¹ H-NMR), it is possible to know the binding mode of the hydrogen atoms present in the compounds of the present invention represented by the general formula.
As a representative example of ¹ H-NMR (δ ppm; tetramethylsilane standard, deuterated chloroform solvent) of the compound, N- (2,
2-Dimethyl-1-phenyl) ethenyl-N- (2'-
The ¹ H-NMR diagram of (methoxyethyl) trifluoromethanesulfonamide is shown in FIG. The analysis results are as follows.

That is, single lines corresponding to three protons were observed at 1.64 ppm and 1.96 ppm, respectively, which can be attributed to the methyl groups (d) and (e). A single line corresponding to 3 protons was observed at 3.29 ppm, which can be attributed to the methyl group (a). Multiple lines corresponding to four protons were observed at 3.3 to 3.6 ppm, which can be attributed to the methylene groups (b) and (c). A single line corresponding to 5 protons was observed at 7.24 ppm, and the protons (f) substituted on the benzene ring
It can be attributed to ~ (j).

(D) By elemental analysis, find each weight% of carbon, hydrogen, nitrogen, sulfur (and halogen when halogen is included),
By further subtracting the sum of the perceived weight percentages of each element from 100, the weight percentage of oxygen can be calculated and thus the composition formula of the compound can be determined.

The sulfonamide compound of the present invention has R, R
^Although the properties vary depending on the types of ^{1 to} R ⁴ , generally, at room temperature and normal pressure, it is a colorless, light yellow, or light brown solid or liquid, and tends to decompose at a certain temperature or higher.

The compound of the present invention is soluble in general organic solvents such as benzene, ether, acetone, alcohol, chloroform, acetonitrile, N, N-dimethylformamide, and dimethylsulfoxide, but is hardly soluble in water.

The method for producing the sulfonamide compound represented by the general formula (1) of the present invention is not particularly limited, and any method may be used. A particularly preferable manufacturing method is as follows.

General formula (However, R represents a substituted or unsubstituted aryl group, heteroaryl group or alkyl group, R ¹ and R ² are the same or different hydrogen atoms or alkyl groups, R ³ is a hydrogen atom, substituted or unsubstituted aryl Group or an alkyl group) and a general formula R ⁴ SO ₂ Z or (R ⁴ SO ₂ ) ₂ O ... (3) (wherein R ⁴ represents a haloalkyl group and Z is a halogen atom). ) Is reacted with a sulfonic acid halide or a sulfonic acid anhydride to obtain the sulfonamide compound represented by the general formula (1).

In the reaction, the charged molar ratio of the imine compound and the sulfonic acid halide or sulfonic acid anhydride may be appropriately determined as needed, but usually an equimolar amount or a slight excess of the sulfonic acid halide or sulfonic acid anhydride is used. It is generally used. In addition, it is generally preferable to use an organic solvent for the reaction, and benzene, toluene, methylene chloride, chloroform, N, N-dimethylformamide and the like are preferably used. In the reaction, hydrogen halide or sulfonic acid is by-produced. This hydrogen halide or sulfonic acid reacts with the imine compound represented by the general formula (2) in the reaction system and causes a decrease in the yield of the product, so it is usually trapped in the reaction system. It is preferable that the agent coexists. The hydrogen halide scavenger is not particularly limited, and known ones can be used, but as the hydrogen halide scavenger which is generally and preferably used, trimethylamine,
Trialkylamines such as triethylamine; pyridine;
Diazabicyclooctane; sodium alcoholate; sodium carbonate, potassium carbonate and the like. The order of adding the raw materials in the reaction is not particularly limited, but generally, the imine compound represented by the general formula (2) is dissolved in a solvent and charged into a reactor, and is represented by the general formula (3) dissolved in the solvent. It is advisable to add the sulphonic acid halide or the sulphonic anhydride with stirring. Of course, it is also possible to continuously add the raw materials to the reaction system and continuously take out the produced reaction product from the reaction system. The reaction temperature can be selected from a wide range, and it is generally sufficient to select it in the range of -20 ° C to 150 ° C, preferably 0 ° C to 100 ° C. The reaction time varies depending on the type of raw material, but it is usually 5 minutes to 10 days, preferably 1 to 40 hours. Also, during the reaction,
It is preferable to perform stirring.

The method for isolating and producing the desired product, that is, the sulfonamide compound represented by the general formula (1) from the reaction system is not particularly limited, and a known method can be adopted. For example, after removing the excess reaction reagent and the generated salt from the reaction solution, the residue is extracted with an organic solvent such as benzene, toluene, chloroform and the like. The organic layer is dried with a drying agent such as Glauber's salt and calcium chloride, and then the organic solvent is distilled off to obtain the desired product.
The refining means may be carried out as necessary, but recrystallization, chromatographie, vacuum distillation and the like can be preferably used.

In the reaction, when R ³ is a hydrogen atom, in addition to the compound represented by the general formula (1), the following general formula [However, R, R ¹ , R ² and R ⁴ are the same as in the general formula (1). ] The compound represented by the following may be formed.

In the present invention, the compound represented by the general formula (1) is a novel compound, and these compounds are 100 g / 10a
Alternatively, it is safe for paddy rice to kill the weeds in paddy fields such as Nobie, firefly, and azena with a dose less than that and to use it at a high concentration of 1000 g / 10a. Thus, the compound represented by the general formula (1) is useful as a herbicide because it has two characteristics that it has a higher herbicidal activity and is superior in selective herbicidal activity as compared with conventionally known sulfonamide-type herbicides. Is.

The sulfonamide compound exerts an excellent herbicidal effect on paddy field weeds, but in particular, shows a remarkable herbicidal effect on the treatment of submerged soil before and after germination of Cyperaceae weeds, broadleaf weeds and perennial weeds. For example, it shows an excellent herbicidal effect not only at the time of germination but also at the growth stage against the highly harmful weeds such as firefly, eel, and azena in the paddy field. It also has high safety in seedling transplantation.

The amount of the sulfonamide compound applied to the paddy field is generally 2 g to 1000 g, preferably 1 g per 10 ares.
It suffices to use 0 g to 500 g as the active ingredient amount.

In the sulfonamide compound represented by the general formula (1), R
Is a substituted or unsubstituted aryl group or heteroaryl group, and R ³ is a hydrogen atom, and is suitable for exhibiting strong herbicidal activity regardless of the types of R ¹ , R ² and R ⁴ .
Furthermore, in the general formula (1), a compound in which R is a substituted or unsubstituted alkyl group and R ³ is a substituted or unsubstituted aryl group is more preferable because it exhibits stronger herbicidal activity.

Examples of paddy weeds in which the sulfonamide compound represented by the general formula (1) exhibits herbicidal effects are as follows.

In particular, it has a high herbicidal effect on cyperaceae weeds such as firefly, cyperus edulis, and cyperus edulis, and it has a significant herbicidal effect on broad-leaved weeds, such as yellow cypress, azalea, konagi, and azalea. Following these, it has a herbicidal effect on grass weeds, but it is better to increase the amount of the active ingredient used or to use a known herbicide such as an amide herbicide or a carbamate herbicide in combination. Results may be obtained. Weeds that can be particularly effectively weeded include, for example, barnyardgrass, Taenia cinerea, barnyard grass, Pleurotus cornucopiae, Pleurotus sp.
Pine pine, Koukinagara, Omodaka, Aginashi, Heraomodaka, Urikawa, Hirumushiro, Denjisou, Seri, Yanagitade, Kokonagi, Warbler, Hokusaku, Mizohakoba,
Red-winged stiletto, Yellow-spotted squirrel, Red hornbill, Hymezin, Pteris chinensis, Azemushiro, Takasaburo, Taukogi, Astragalus serrata, Scutellaria baicalensis, Sweet pepper,
Paddy field weeds such as Abeno, Azena and Pepper.

Further, since the sulfonamide compound represented by the general formula (1) has a high degree of selectivity between paddy field weeds and paddy rice, it can be applied in a long-term growth stage from the germination of rice to the growing season. It is possible and has an excellent advantage that the suitable treatment period is remarkably long. In addition, the advantage that the sulfonamide compound can be applied to flooded direct-seeded rice very safely is a great feature of the sulfonamide compound.

Furthermore, since it exerts a selective herbicidal effect when used as a herbicide for upland fields, wheat, barley, corn,
It can be safely applied not only to grasses such as upland rice but also to broad-leaved crops such as soybean, cotton and beet.

Further, since the sulfonamide compound represented by the general formula (1) of the present invention affects the growth of plants, it can be used as a defoliant, a germination inhibitor, and a growth regulator.

The use mode of the sulfonamide compound represented by the general formula (1) of the present invention is not particularly limited, and the use mode of a known herbicide can be used as it is. For example, an inert solid carrier, a liquid carrier, an emulsifying dispersant or the like may be used to form an arbitrary dosage form such as granules, powders, emulsions, wettable powders, tablets, oils, aerosols and smoke agents. Of course, auxiliary agents in the formulation, such as spreading agents, diluents, surfactants, materials, etc., can be appropriately mixed.

Further, the sulfonamide compound represented by the general formula (1) of the present invention has a strong antibacterial activity against plant pathogens such as fungi and wilt disease fungi, athlete's foot fungi and E. coli,
It is also useful as a germicide. These properties have not been recognized with known sulfonamide compounds. The bactericidal activity is found in almost all of the compounds of the general formula (1), but in particular, R is a substituted or unsubstituted aryl group or heteroaryl group, and R ³ is a hydrogen atom or a substituted or unsubstituted alkyl group. Is suitable for showing stronger bactericidal activity.

The compound of the present invention can be widely applied to various pathogens belonging to, for example, basidiomycetes, soybean fungi, ascomycetes, incomplete fungi and bactericides. In particular, the sulfonamide compound of the present invention exhibits excellent bactericidal activity against Bacillus subtilis, sesame leaf blight fungus, wilt disease fungus, white bacterium, Escherichia coli and the like.

(Examples) In order to describe the present invention more specifically, examples will be described below, but the present invention is not limited to these examples.

Example 1 α-isopropyl-benzylidene-2-methoxyethylamine 2.0 g (0.0098 mo) of chloroform (10 m
) Triethylamine 1.50m (0.011mo) in solution
3.03 g of trifluoromethanesulfonic anhydride
A solution of (0.011mo) in chloroform (15m) was added dropwise. After stirring overnight, the reaction solution was poured into ice water and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate, chloroform was distilled off, and the residue was purified by silica gel column (benzene: acetone = 30: 1) to obtain 1.36 g of a colorless liquid. This thing I
The result of measuring R is as shown in FIG.

The elemental analysis values are C50.09%, H5.38%, N4.20
% And the composition formula C₁₄H₁₈F₃NO₃For S (337.36)
To calculated values of C49.84%, H5.38%, N4.15%
Well matched Also, when MS was measured, M / e337
Corresponding to the peak, M at m / e 268 -CF₃Corresponding to
M at peak, m / e 204 -SO₂CF₃Corresponding to the peak,
to m / e131Each peak corresponding to Also¹1 H-NMR (δ:
ppm; tetramethylsilane standard, deuterated chloroform solvent)
The result of the measurement is shown in FIG. The analysis result is
It was on the street.

Single lines corresponding to three protons are shown at 1.64 ppm and 1.96 ppm, which correspond to the methyl protons of (e) and (d). 3.
A single line corresponding to three protons was shown at 29 ppm, which corresponded to the methyl proton in (a). Multiple lines corresponding to four protons were shown at 3.3 to 3.6 ppm, which corresponded to the methylene protons of (b) and (c). A single line of 5 protons was shown at 7.24 ppm, which corresponds to the proton of the benzene ring in (f).

From the above results, it became clear that the isolated product was N- (2,2-dimethyl-1-phenyl) ethenyl-N- (2'-methoxyethyl) trifluoromethanesulfonamide. The yield was 41.3%.

Example 2 α-isopropyl- (2-thienyl) methylideneamine
Triethylamine 5.0m (0.036mo) was added to a solution of 5.0g (0.033mo) in chloroform (25m), and trifluoromethanesulfonic anhydride 10.14g (0.036mo) was added.
) In chloroform (25 m) was added dropwise. After stirring overnight, the reaction solution was poured into ice water and extracted with chloroform. After drying the chloroform layer over anhydrous sodium sulfate,
Chloroform was distilled off and the residue was purified by silica gel chromatography (benzene: acetone = 30: 1) to obtain 2.48 g of a light brown liquid.

The elemental analysis values are C37.93%, H3.54%, N4.72
% And the composition formula C₉H_TenF₃NO₂S₂Against (285.30)
To calculated values of C37.89%, H3.53%, N4.91%
Well matched Moreover, when MS was measured, m / e 28
5 to M Corresponding to the peak, M at m / e 152 -SO₂C
F₃To the peak corresponding to m / e131Each peak corresponding to

In addition, ¹ H-NMR (δ: ppm; tetramethylsilane standard, deuterated chloroform solvent) was measured, and the analysis results were as follows.

Single lines corresponding to three protons are shown at 1.86 ppm and 1.95 ppm, respectively, which correspond to the methyl protons of (a) and (b). 6.
A broad single line for one proton is shown at 7 to 6.8 ppm, (c)
Corresponding to the proton of the amino group. 6.8-7.0ppm and 7.9
Shows multiple lines of 2 and 1 protons of ~ 8.0 ppm,
This corresponds to the proton of the thiophene ring in (d).

The above results revealed that the isolated product was N- [2,2-dimethyl-1- (2'-thienyl)] ethenyl-trifluoromethanesulfonamide. The yield was 26.6%.

Further, in the above reaction, in addition to the above compounds, a thin spot was observed at a R _f value of 0.7 to 0.8 in thin layer chromatography (solvent system; benzene: acetone = 30: 1). (The R _f value of the above compound was 0.4 to 0.5.) The compound at this spot was isolated and purified by silica gel column chromatography in the same manner as above to obtain 1.65 g of a light brown liquid.

The elemental analysis values are C37.85%, H3.50%, N5.01%
And composition formula C₉H_TenF₃NO₂S₂Total for (285.30)
The calculated values are C37.89%, H3.53%, N4.91%.
Agreed Moreover, when MS was measured, it was m / e285.
To M Corresponding to the peak, M at m / e 152 -SO₂CF₃
Each peak corresponding to

In addition, ¹ H-NMR (δ: ppm; tetramethylsilane standard, deuterated chloroform solvent) was measured, and the analysis results were as follows.

A double line for 6 protons is shown at 1.23 ppm, (a) and (b)
Corresponding to the methyl proton of. A quadruple line for one proton is shown at 3.29 ppm and 3.41 ppm, which corresponds to the proton of (c). Multiple lines of two and one protons were shown at 6.9 to 7.3 ppm and 7.5 to 7.7 ppm, which corresponded to the protons of the thiophene ring of (d).

From the above results, the isolated product is α-isopropyl-
(2-thienyl) methylidene-trifluoromethanesulfonylamine, and it was revealed that the above compound was also produced in the reaction. The yield was 17.8%.

Example 3 Various compounds represented by the following general formula by the same method as in Example 1 and Example 2, (However, R and R ^{1 to} R ⁴ are described in Table 1.) were synthesized. The yield and elemental analysis values of the synthesized compounds are shown in Table 1.

The abbreviations in Table 1 are as shown below.

Et: ethyl group, n-Pr; normal propyl group, i-Pr and
iso-Pr; isopropyl group, n-Bu; normal butyl group, se
c-Bu; secondary butyl group, iso-Bu; isobutyl group,
n-Hex; normal hexyl group.

Formulation Example 1 (Granule) 2 parts by weight of the compound synthesized in Example 1, 1 part by weight of dioctyl succinate, 3 parts by weight of sodium lignin sulfonate,
30 parts by weight of bentonite and 64 parts by weight of talc were well mixed and pulverized, water was added and kneaded, and then granulated and dried.
The particle size was adjusted to ˜32 mesh to obtain 2% granule.

Formulation Example 2 (wettable powder) 10 parts by weight of the compound synthesized in Example 1, 2 parts by weight of polyoxyethylene nonylphenyl ether, fine clay 40
Parts by weight and 48 parts by weight of Sieglite were crushed and mixed with a hammer mill to obtain a 10% wettable powder.

Formulation Example 3 (emulsion) 20 parts by weight of the compound synthesized in Example 2, 70 parts by weight of xylene, 5 parts by weight of polyoxyethylene alkyl allyl ether, and 5 parts by weight of sodium alkylbenzene sulfonate are mixed and dissolved to obtain a 20% emulsion. It was

Example 4 A rice pot of 1/8850 ares was filled with paddy soil (alluvial loam soil) which was stirred by adding water, and rice seedlings (cultivar: Akinishiki) at the 3-leaf stage after seeding paddy weeds to a depth of 2 cm. After transplanting, water was added to make a 2 cm submerged state. Next, a predetermined amount of the water-diluted solution of the wettable powder of each compound obtained in Example 1, Example 2 and Example 3 was dropped at the time of germination of weeds. After the treatment, the plants were grown in a greenhouse at an average temperature of 25 ° C., and the herbicidal effect of each test compound was investigated 3 weeks later. The results are shown in Table 2.
However, what is meant by broad leaves in the table is Azena, Prickly Pear, or Pepper. The evaluation was made into 6 levels, and the evaluation of herbicidal efficacy was expressed by the numbers 0 to 5 as follows.

0 ...... Weed control rate 0-9% 1 …… 〃 10-29% 2 …… 〃 30-49% 3 …… 〃 50-69% 4 …… 〃 70-89% 5 …… Weed control rate 90-100% Regarding the phytotoxicity of transplanted rice, the plant height, the number of divisions, and the total weight (air dry amount) relative to the untreated plots were calculated, and the worst one of the three factors was taken and evaluated from 0 to 5.

0 …… to untreated area ratio 100% 1 …… 〃 90-99% 2 …… 〃 80-89% 3 …… 〃 60-79% 4 …… 〃 40-59% 5 …… 〃 0-39% The following two compounds as the known compounds represented by (A) were evaluated in the same manner as above, and the results are shown in Table 2 as a comparative example.

Example 5 A nutrient medium containing 1.5% agar was sterilized by heating at 121 ° C. for 15 minutes, cooled to 50 ° C., and a suspension of pre-grown bacterial cells or spores in sterile water was added. It was mixed well, poured into a dish and solidified into a flat plate. N- [2,2-dimethyl-1- (4 'synthesized in Example 3
-Methoxyphenyl)] ethenyl-trifluoromethanesulfonamide (compound NO.3) was immersed in a methanol solution containing about 15%, and circular paper rolls having a diameter of 8 mm were soaked and solidified by removing the excess on the paper rolls. Place on agar. About 3
After culturing at 0 ° C. for 24 to 48 hours, the diameter of the inhibition circle was measured.

As a mold for control sterilization, Essieria Richia coli B
(Escherichia coli B), Bacillus subtilis (Bati
llus niger), Aspergillus
niger), Cochliobolus (Cochliobolu)
s miyabeanus), Trichophyton Rubram (Trichoph
yton rubrum), Fusarium oxysvolum (Fusariu)
m oxysporum). The results of the antibacterial test are shown in Table 3.

Example 6 The compounds synthesized in Example 1, Example 2 and Example 3 were
An antibacterial test was conducted in the same manner as in Example 5, and the diameter of the inhibition circle was measured. The results are shown in Table 4.

[Brief description of drawings]

1 and 2 show the IR spectrum and ¹ H-NMR spectrum of the sulfonamide compound obtained in Example 1, respectively.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Office reference number FI Technical indication location A01N 43/36 A 9159-4H 43/38 9159-4H 43/40 101 C 9159-4H 43/56 C 9159-4H C07D 207/335 8314-4C 209/14 9284-4C 213/36 231/12 307/52 307/81 333/20 333/58

Claims (3)

[Claims] 1. A general formula [Wherein R is a substituted or unsubstituted phenyl group, a naphthyl group, a heteroaryl group having 3 to 9 carbon atoms or an alkyl group containing a 5- or 6-membered ring having sulfur, oxygen or nitrogen as a hetero atom] Therefore, the substituent is selected from a halogen atom, a cyano group, a nitro group, an alkylamino group, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylthio group and a haloalkyl group. R ¹ and R ² are the same or different hydrogen atoms or alkyl groups. R ³ is a hydrogen atom, or a substituted or unsubstituted phenyl group, phenylalkyl group, heteroarylalkyl group (the heteroaryl group is the same as R), an alkyl group or an alkenyl group, and the substituent is a halogen atom. , Cyano group, nitro group, alkyl group, alkoxy group, alkenyloxy group, alkoxyalkyl group, haloalkyl group and alkylthio group. R ⁴ represents a haloalkyl group. ] A sulfonamide compound represented by 2. General formula [Wherein R is a substituted or unsubstituted phenyl group, a naphthyl group, a heteroaryl group having 3 to 9 carbon atoms or an alkyl group containing a 5- or 6-membered ring having sulfur, oxygen or nitrogen as a hetero atom] Therefore, the substituent is selected from a halogen atom, a cyano group, a nitro group, an alkylamino group, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylthio group and a haloalkyl group. R ¹ and R ² are the same or different hydrogen atoms or alkyl groups. R ³ is a hydrogen atom, or a substituted or unsubstituted phenyl group, phenylalkyl group, heteroarylalkyl group (the heteroaryl group is the same as R), an alkyl group or an alkenyl group, and the substituent is a halogen atom. , Cyano group, nitro group, alkyl group, alkoxy group, alkenyloxy group, alkoxyalkyl group, haloalkyl group and alkylthio group. R ⁴ represents a haloalkyl group. ] A herbicide containing a sulfonamide compound represented by 3. General formula [Wherein R is a substituted or unsubstituted phenyl group, a naphthyl group, a heteroaryl group having 3 to 9 carbon atoms or an alkyl group containing a 5- or 6-membered ring having sulfur, oxygen or nitrogen as a hetero atom] Therefore, the substituent is selected from a halogen atom, a cyano group, a nitro group, an alkylamino group, an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylthio group and a haloalkyl group. R ¹ and R ² are the same or different hydrogen atoms or alkyl groups. R ³ is a hydrogen atom, or a substituted or unsubstituted phenyl group, phenylalkyl group, heteroarylalkyl group (the heteroaryl group is the same as R), an alkyl group or an alkenyl group, and the substituent is a halogen atom. , Cyano group, nitro group, alkyl group, alkoxy group, alkenyloxy group, alkoxyalkyl group, haloalkyl group and alkylthio group. R ⁴ represents a haloalkyl group. ] A fungicide containing a sulfonamide compound represented by