JPH09227501A - Sulfonamide derivative and insecticide, acaricide and nematicide containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new sulfonamide derivative which has strong insecticidal activity as well as potent acaricidal and nematicidal activities against a variety of pests troublesome in agriculture. SOLUTION: This sulfonamide derivative is represented by formula I (R<1> and R<2> are each H or a lower haloalkyl; R<3> is a lower alkoxy; X and Y are each phenoxy; m and n are each 1-3), typically N-propargyl-3,5-dichloro-N-(4- trifluoromethylphenyl)benzenesulfonamide. The compound of formula I is prepared by reaction of 1 mole of a sulfonyl chloride represented by formula II (X<1> is halogen) with 0.5-2 moles of an aniline of formula III at 130-200 deg.C for 3-15 hours to form a sulfonamide of formula IV, then allowing 1 mole of the product compound of formula IV to react with about 0.5-4 moles of a halide of formula V in the presence of a base such as sodium carbonate in a suitable solvent such as an ether at 0 deg.C - the boiling point of the solvent for about 1-8 hours.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a sulfonamide derivative and insecticides, acaricides and nematicides containing the derivative.

[0002]

To date, various compounds having biological activity are known among sulfonamide derivatives. For example, in Japanese Patent Laid-Open No. 3-258771,
It is described that a sulfonamide derivative having a 1,2,4-oxadiazole group has herbicidal activity. However, the above publication does not teach or suggest that the compounds described in the publication have insecticidal activity, acaricidal activity and nematicidal activity. Also French Patent No. 957
No. 493 describes the general formula

[0003]

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[In the formula, p represents an integer of 1 to 3. ] It is disclosed that the sulfonamide derivative represented by the following formula has acaricidal activity. However, in the French patent specification, a sulfonamide derivative represented by the above general formula,
No teaching is given as to whether or not it has biological activity such as insecticidal activity or nematicidal activity other than acaricidal activity.

[0005]

SUMMARY OF THE INVENTION One object of the present invention is to provide:
It is intended to provide a drug having excellent biological activity for agriculture.

[0006] Another object of the present invention is to provide a sulfonamide derivative having extremely strong insecticidal activity against various agricultural harmful insect pests.

Another object of the present invention is to provide a sulfonamide derivative having a strong acaricidal activity and nematicidal activity.

The present inventors have conducted various studies on sulfonamide derivatives in order to develop a drug having excellent biological activity for agriculture. As a result, the compound represented by the following general formula (1) causes various agricultural problems. It was found that they have extremely strong insecticidal activity against pests as well as strong acaricidal activity and nematicidal activity. The present invention has been completed based on such findings.

The sulfonamide derivative of the present invention is a novel compound not described in the literature,

[0010]

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[In the formula, R ¹ and R ² are the same or different and each represents a hydrogen atom, a lower haloalkyl group or a halogen atom. R ³ represents an ethynyl group, a cyano group, a lower alkoxy group or a lower alkoxycarbonyl group. X and Y
Are the same or different, a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group,
Lower haloalkoxy group, phenoxy group which may have a substituent, phenyl group which may have a substituent, pyridyloxy group which may have a substituent, cyano group, nitro group, lower alkylthio group or lower alkylsulfonyl group Indicates. m and n each represent an integer of 1 to 3. ] It is a sulfonamide derivative represented by these.

The sulfonamide derivative of the present invention has a strong insecticidal activity as well as a strong acaricidal and nematicidal activity, and is useful as an insecticide, acaricide and nematicide.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Each group shown in the present specification is specifically as follows.

Examples of the lower haloalkyl group include trifluoromethyl, trichloromethyl, chloromethyl, bromomethyl, fluoromethyl, iodomethyl, difluoromethyl, dibromomethyl, 2-chloroethyl, 2,
2,2-trifluoroethyl, 2,2,2-trichloroethyl, 3-bromopropyl, 3-chloropropyl,
2,3-dichloropropyl, 4,4,4-trichlorobutyl, 4-fluorobutyl, 5-chloropentyl, 3-
Chloro-2-methylpropyl, 5-bromohexyl,
As a substituent such as a 5,6-dichlorohexyl group, a linear or branched alkyl group having 1 to 3 halogen atoms and 1 to 6 carbon atoms can be exemplified.

Examples of the halogen atom include a fluorine atom,
Examples include a chlorine atom, a bromine atom and an iodine atom.

Examples of the lower alkoxy group include linear or branched alkoxy groups having 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy and hexyloxy groups. it can.

The lower alkoxycarbonyl group is, for example, a straight chain or branched chain having 1 to 6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl and t-butoxycarbonyl group. An example is a linear alkoxycarbonyl group.

As the lower alkyl group, for example, methyl,
Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms, such as ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, and hexyl groups.

The lower haloalkoxy group is, for example,
Trifluoromethoxy, trichloromethoxy, chloromethoxy, bromomethoxy, fluoromethoxy, iodomethoxy, difluoromethoxy, dibromomethoxy, 2-
Chloroethoxy, 2,2,2-trifluoroethoxy,
2,2,2-Trichloroethoxy, 3-bromopropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 4,4,4-trichlorobutoxy, 4-fluorobutoxy, 5-chloropentyloxy, 3-chloro- 2-
Methylpropoxy, 5-bromohexyloxy, 5,6
Examples of the substituent such as -dichlorohexyloxy group include a linear or branched alkoxy group having 1 to 3 halogen atoms and 1 to 6 carbon atoms.

Examples of the phenoxy group which may have a substituent include phenoxy, 2-methylphenoxy,
3-methylphenoxy, 4-methylphenoxy, 2-ethylphenoxy, 3-propylphenoxy, 4-butylphenoxy, 2-pentylphenoxy, 3-hexylphenoxy, 3,4-dimethylphenoxy, 3,4,5-
Trimethylphenoxy, 2-methoxyphenoxy, 3-
Methoxyphenoxy, 4-methoxyphenoxy, 2-ethoxyphenoxy, 4-ethoxyphenoxy, 3-propoxyphenoxy, 4-propoxyphenoxy, 4-butoxyphenoxy, 2-pentyloxyphenoxy, 3
-Hexyloxyphenoxy, 2,4-dimethoxyphenoxy, 3,4-diethoxyphenoxy, 3,4,5-
Trimethoxyphenoxy, 2-hydroxyphenoxy,
3-hydroxyphenoxy, 4-hydroxyphenoxy, 2,4-dihydroxyphenoxy, 3,4-dihydroxyphenoxy, 2,4,6-trihydroxyphenoxy, 2-acetyloxyphenoxy, 3-propionyloxyphenoxy, 2-benzyloxy Phenoxy,
3-benzyloxyphenoxy, 4-benzyloxyphenoxy, 2- (2-phenylethoxy) phenoxy,
3- (3-phenylpropoxy) phenoxy, 4- (4
-Phenylbutoxy) phenoxy, 3- (1-phenylethoxy) phenoxy, 2- (5-phenylpentyloxy) phenoxy, 3- (6-phenylhexyloxy) phenoxy, 2,4-dibenzyloxyphenoxy, 3,4 -Dibenzyloxyphenoxy, 3,4,5
-Tribenzyloxyphenoxy, 4-butyryloxyphenoxy, 2-pentanoyloxyphenoxy, 4-
Hexanoyloxyphenoxy, 2,4-diacetyloxyphenoxy, 2,6-diacetyloxyphenoxy, 3,4,5-triacetyloxyphenoxy, 2-
Trifluoromethoxyphenoxy, 3- (2-chloroethoxy) phenoxy, 2- (3-bromopropoxy) phenoxy, 4-iodomethoxyphenoxy, 2- (2,
3-dichloropropoxy) phenoxy, 3- (4-fluorobutoxy) phenoxy, 4- (3-chloro-2-methylpropoxy) phenoxy, 2- (5-bromohexyloxy) phenoxy, 3- (5,6-dichloro Hexyloxy) phenoxy, 4- (2,2,2-trichloroethoxy) phenoxy, 2,4-bistrifluoromethoxyphenoxy, 2,4,6-tri (trifluoromethoxy) phenoxy, 2-aminomethoxyphenoxy, 3
-(1-Aminoethoxy) phenoxy, 4- (3-aminopropoxy) phenoxy, 2- (4-aminobutoxy) phenoxy, 3- (5-aminopentyloxy) phenoxy, 4- (6-aminohexyloxy) phenoxy , 2-methylaminomethoxyphenoxy, 3- (2-
Propylaminoethoxy) phenoxy, 2- (3-isopropylaminopropoxy) phenoxy, 4- (4-butylaminobutoxy) phenoxy, 2- (5-pentylaminopentyloxy) phenoxy, 3- (6-hexylaminohexyloxy) Phenoxy, 4-dimethylaminomethoxyphenoxy, 2- (N-ethyl-N-propylaminomethoxy) phenoxy, 2-methyl-4-methoxyphenoxy, 2-methyl-6-hydroxyphenoxy, 4-methyl-2- (3 -Bromopropoxy) phenoxy, 4-methoxy-2- (3-isopropylaminopropoxy) phenoxy, 2-phenylphenoxy, 3
-Phenylphenoxy, 4-phenylphenoxy, 2-
Nitrophenoxy, 3-nitrophenoxy, 4-nitrophenoxy, 2,3-dinitrophenoxy, 2,4,6
-Trinitrophenoxy, 2-aminophenoxy, 3-
Aminophenoxy, 4-aminophenoxy, 2,4-diaminophenoxy, 3,4,5-triaminophenoxy, 4-acetylaminophenoxy, 2-propionylaminophenoxy, 3-butyrylaminophenoxy, 4
-Pentanoylaminophenoxy, 4-hexanoylaminophenoxy, 2,3-diacetylaminophenoxy, 2,4,6-triacetylaminophenoxy group and the like, which has a straight chain having 1 to 6 carbon atoms or a substituent on the phenyl ring. A branched alkyl group, a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, a straight-chain or branched alkanoyloxy group having 1 to 6 carbon atoms, and a halogen atom as a substituent
A linear or branched alkoxy group having 1 to 6 carbon atoms or a nitro group, an amino group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms as a substituent,
A phenyl group and a linear or branched alkoxy group having 1 to 6 carbon atoms having an amino group which may have 1 to 2 linear or branched alkyl groups having 1 to 6 carbon atoms as a substituent Examples thereof include a phenoxy group which may have 1 to 3 groups selected from the group consisting of

As the phenyl group which may have a substituent, for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-propylphenyl, 4-butylphenyl, 2 −
Pentylphenyl, 3-hexylphenyl, 3,4-dimethylphenyl, 3,4,5-trimethylphenyl, 2
-Methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 4-ethoxyphenyl, 3-propoxyphenyl, 4-propoxyphenyl, 4-butoxyphenyl, 2-pentyloxyphenyl, 3-hexyloxyphenyl , 2,4-dimethoxyphenyl, 3,4-diethoxyphenyl, 3,4,5
-Trimethoxyphenyl, 2-hydroxyphenyl, 3
-Hydroxyphenyl, 4-hydroxyphenyl, 2,
4-dihydroxyphenyl, 3,4-dihydroxyphenyl, 2,4,6-trihydroxyphenyl, 2-acetyloxyphenyl, 3-propionyloxyphenyl, 2-benzyloxyphenyl, 3-benzyloxyphenyl, 4-benzyloxy Phenyl, 2- (2-phenylethoxy) phenyl, 3- (3-phenylpropoxy) phenyl, 4- (4-phenylbutoxy) phenyl, 3- (1-phenylethoxy) phenyl, 2- (5
-Phenylpentyloxy) phenyl, 3- (6-phenylhexyloxy) phenyl, 2,4-dibenzyloxyphenyl, 3,4-dibenzyloxyphenyl,
3,4,5-tribenzyloxyphenyl, 4-butyryloxyphenyl, 2-pentanoyloxyphenyl,
4-hexanoyloxyphenyl, 2,4-diacetyloxyphenyl, 2,6-diacetyloxyphenyl,
3,4,5-Triacetyloxyphenyl, 2-trifluoromethoxyphenyl, 3- (2-chloroethoxy)
Phenyl, 2- (3-bromopropoxy) phenyl, 4
-Iodomethoxyphenyl, 2- (2,3-dichloropropoxy) phenyl, 3- (4-fluorobutoxy) phenyl, 4- (3-chloro-2-methylpropoxy) phenyl, 2- (5-bromohexyloxy) Phenyl,
3- (5,6-dichlorohexyloxy) phenyl, 4
-(2,2,2-trichloroethoxy) phenyl, 2,
4-bistrifluoromethoxyphenyl, 2,4,6-
Tri (trifluoromethoxy) phenyl, 2-aminomethoxyphenyl, 3- (1-aminoethoxy) phenyl, 4- (3-aminopropoxy) phenyl, 2- (4
-Aminobutoxy) phenyl, 3- (5-aminopentyloxy) phenyl, 4- (6-aminohexyloxy) phenyl, 2-methylaminomethoxyphenyl, 3
-(2-propylaminoethoxy) phenyl, 2- (3
-Isopropylaminopropoxy) phenyl, 4- (4
-Butylaminobutoxy) phenyl, 2- (5-pentylaminopentyloxy) phenyl, 3- (6-hexylaminohexyloxy) phenyl, 4-dimethylaminomethoxyphenyl, 2- (N-ethyl-N-propylaminomethoxy) ) Phenyl, 2-methyl-4-methoxyphenyl, 2-methyl-6-hydroxyphenyl, 4-
Methyl-2- (3-bromopropoxy) phenyl, 4-
Methoxy-2- (3-isopropylaminopropoxy)
Phenyl, 2-phenylphenyl, 3-phenylphenyl, 4-phenylphenyl, 2-nitrophenyl, 3-
Nitrophenyl, 4-nitrophenyl, 2,3-dinitrophenyl, 2,4,6-trinitrophenyl, 2-aminoethyl, 3-aminophenyl, 4-aminophenyl, 2,4-diaminophenyl, 3,4 , 5-triaminophenyl, 4-acetylaminophenyl, 2-propionylaminophenyl, 3-butyrylaminophenyl,
4-pentanoylaminophenyl, 4-hexanoylaminophenyl, 2,3-diacetylaminophenyl,
A linear or branched alkyl group having 1 to 6 carbon atoms or a linear or branched alkoxy group having 1 to 6 carbon atoms as a substituent on a phenyl ring such as a 2,4,6-triacetylaminophenyl group. A group, a hydroxyl group, a linear or branched alkanoyloxy group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 3 carbon atoms having 1 to 3 halogen atoms as a substituent,
A nitro group, an amino group which may have a linear or branched alkanoyl group having 1 to 6 carbon atoms as a substituent, a phenyl group, and a linear or branched alkyl group having 1 to 6 carbon atoms as a substituent A phenyl group which may have 1 to 3 groups selected from the group consisting of a linear or branched alkoxy group having 1 to 6 carbon atoms and having an amino group which may have 1 or 2 groups can be exemplified. .

Examples of the pyridyloxy group which may have a substituent include 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy, (3-methyl) -2-pyridyloxy and (4-methyl) -2. -Pyridyloxy,
(5-methyl) -2-pyridyloxy, (2-methyl)
-3-Pyridyloxy, (4-methyl) -3-pyridyloxy, (5-methyl) -3-pyridyloxy, (2-
Methyl) -4-pyridyloxy, (3-methyl) -4-
Pyridyloxy, (3-butyl) -2-pyridyloxy, (4-butyl) -2-pyridyloxy, (5-butyl) -2-pyridyloxy, (2-butyl) -3-pyridyloxy, (4- Butyl) -3-pyridyloxy,
(5-butyl) -3-pyridyloxy, (2-butyl)
-4-pyridyloxy, (3-butyl) -4-pyridyloxy, (3-trifluoromethyl) -2-pyridyloxy, (4-trifluoromethyl) -2-pyridyloxy, (5-trifluoromethyl) -2-pyridyloxy, (2-trifluoromethyl) -3-pyridyloxy, (4-trifluoromethyl) -3-pyridyloxy, (5-trifluoromethyl) -3-pyridyloxy, (2-trifluoro Methyl) -4-pyridyloxy, (3-trifluoromethyl) -4-pyridyloxy, (3-trichloromethyl) -2-pyridyloxy,
(4-trichloromethyl) -2-pyridyloxy, (5
-Trichloromethyl) -2-pyridyloxy, (2-trichloromethyl) -3-pyridyloxy, (4-trichloromethyl) -3-pyridyloxy, (5-trichloromethyl) -3-pyridyloxy, (2-trichloro) Methyl) -4-pyridyloxy, (3-trichloromethyl)
Pyridyl which may have 1 to 3 groups selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms and a halogen atom as a substituent on the pyridine ring such as -4-pyridyloxy group. An oxy group can be exemplified.

Examples of the lower alkylthio group include linear or branched alkylthio groups having 1 to 6 carbon atoms such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio and hexylthio groups. .

Examples of the lower alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl,
Examples thereof include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, such as tert-butylsulfonyl, pentylsulfonyl, and hexylsulfonyl groups.

The sulfonamide derivative represented by the general formula (1) includes a sulfonamide derivative represented by the following general formula (1a) and a sulfonamide derivative represented by the general formula (1b).

[0026]

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[In the formula, R ¹ , R ² , X, Y, m and n are the same as defined above. ]

[0028]

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[In the formula, R ³ 'represents a cyano group, a lower alkoxy group or a lower alkoxycarbonyl group. X'represents a hydrogen atom, a halogen atom, a lower haloalkyl group or a cyano group. Y'represents a hydrogen atom, a halogen atom, a lower haloalkyl group, a cyano group or a nitro group. m and n are the same as above. Typical examples of the sulfonamide derivative represented by the general formula (1a) are shown below.

X is a halogen atom, Y is a lower haloalkyl group, R ¹ and R ² are hydrogen atoms, m is an integer of 1 to 3,
Compound of the general formula (1a) in which n is 1 or 2, X is a halogen atom, Y is a lower haloalkyl group, R ¹ is a hydrogen atom, R ² is a halogen atom, m is an integer of 1 to 3, n is 1 Or a compound of the general formula (1a), wherein X is a cyano group, Y is a lower haloalkyl group, R ¹ and R ² are hydrogen atoms, and m is 1, n is 1 or 2 Compound X is a cyano group, Y is a lower haloalkyl group, R ¹ is a hydrogen atom, R ² is a halogen atom, m is 1, n is 1 or 2
A compound of the general formula (1a) wherein X is a lower haloalkyl group, Y is a lower haloalkyl group, R
A compound of the general formula (1a) in which ¹ and R ² are hydrogen atoms, and m and n are 1 or 2, and typical examples of the sulfonamide derivative represented by the general formula (1b) are shown below. .

A compound of the general formula (1b) in which X'is a halogen atom, Y'is a lower haloalkyl group, m is 1 to 3 and n is 1 or 2, X'is a lower haloalkyl group and Y'is a lower haloalkyl group. a group, m and n is 1 or 2 formula (1b) of the compounds wherein R ³ formula is a lower alkoxy group 'is and R ³ in formula is a cyano group (1b)' of (1b) Compound.

The sulfonamide derivative of the present invention is produced, for example, by the method shown in the following reaction formula-1.

Reaction formula-1

[0034]

[Chemical 6]

[Wherein R ¹ , R ² , R ³ , X, Y, m, n
Is the same as above. X ¹ represents a halogen atom. That is, according to the above Reaction Scheme-1, the compound of the present invention represented by the general formula (1) comprises a sulfonyl chloride represented by the general formula (2) and an aniline represented by the general formula (3). It is produced by reacting and then reacting the obtained sulfonamide of the general formula (4) with the halide of the general formula (5) in the presence of a base.

The reaction between the sulfonyl chlorides of the general formula (2) and the anilines of the general formula (3) is described in JP-A-4-145.
It is carried out according to the method described in JP-A No. 060. That is, the sulfonyl chlorides of the general formula (2) and the anilines of the general formula (3) are usually used in a proportion of 0.5 to 2 mols, preferably 0.7 to 1 mols, relative to 1 mol of the former. It is preferable to set it to 3 mol. This reaction is usually performed in an organic solvent. As the organic solvent, conventionally known ones can be widely used, for example, benzene, toluene, aromatic hydrocarbons such as xylene, dichloromethane, chloroform,
Examples thereof include halogenated hydrocarbons such as carbon tetrachloride and the like, and mixed solvents thereof. This reaction is advantageously carried out in the presence of a basic compound such as β-picoline and γ-picoline. The amount of the basic compound used is usually 0.01 to 1 per mol of the sulfonyl chlorides of the general formula (2).
It is preferable that the amount is 0.1 mol, preferably 0.1 to 0.5 mol.
The above reaction is usually 130 to 200 ° C., preferably 140.
The reaction proceeds suitably at ˜180 ° C., and generally the reaction is completed in about 3 to 15 hours.

The reaction of the sulfonamides of the general formula (4) with the halide of the general formula (5) can usually be carried out in the presence of a base in a suitable solvent. Examples of the solvent used include ethers such as diethyl ether and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol and ethanol, dimethylformamide and dimethylacetamide. Examples thereof include amides and mixed solvents thereof. Examples of the base to be used include anhydrous alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride. Examples thereof include compounds. These bases may be used alone or in combination of two or more. The amount of such base is represented by the general formula (4)
It is usually about 1 to 5 times, preferably about 1 to 2 times the molar amount of the sulfonamide.
The sulfonamides of the general formula (4) and the halides of the general formula (5) are usually used in a ratio of 0.
It is about 5 to 2 times mol, preferably about 1 to 1.2 times mol. The reaction usually proceeds well at 0 ° C to the boiling point of the solvent used, and is generally completed in about 1 to 8 hours. In the above reaction, as the halide of the general formula (5) used as a starting material, a commercially available product can be used as it is.

The compound of the present invention represented by the general formula (1) obtained by the above-mentioned method can be obtained from a reaction mixture by a conventional separation means such as a solvent extraction method, a recrystallization method and a column chromatography method. It is easily isolated and purified.

According to the production method shown in the above reaction formula-1,
The compound of the present invention can be produced in high yield and high purity.

The compound of the present invention effectively acts against various pests which are widely problematic in agriculture, and examples of pests which act particularly effectively include, for example, Lepidoptera such as Spodoptera litura and Plutella xylostella, Aphis gossypii and Pleurotus sp. The hemiptera of the above, spider mites such as the spider mites, citrus spider mites, and nematodes such as sweet potato nematodes and the like can be exemplified.

When the compounds of the present invention are used as insecticides, acaricides and nematicides, they are emulsions, wettable powders, water-soluble solvents, granules, fine granules, granules, powders, coating agents, spray formulations,
Aerosol formulation, microcapsule formulation, fumigation formulation,
It can be used in a form such as a smoke preparation. In preparing these preparations, various surfactants can be used for emulsification, dispersion, suspension, and foaming. Specific examples of the surfactant include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester, etc. as the nonionic surfactant, and alkylbenzene sulfonate, alkylsulfone, etc. as the anionic surfactant. Examples thereof include succinate, alkyl sulfate, polyoxyethylene alkyl sulfate, allyl sulfonate, and lignin sulfite. As the dissolving agent, the diluent and the carrier, various organic solvents, various aerosol propellants, various natural minerals and various synthetic compounds can be used.
As the organic solvent, for example, benzene, toluene, xylene, ethylbenzene, chlorobenzene, alkylnaphthalene, chloroethylene, cyclohexanone, methyl ethyl ketone, methyl isobutyl ketone, alcohols,
Cellosolves, dimethylformamide, dimethylsulfoxide, acetonitrile, mineral oil fractions, water and the like can be preferably used. Examples of the aerosol propellant include, for example, propane, butane, halogenated hydrocarbon, nitrogen, carbon dioxide and the like. These preparations may be colored with an organic or inorganic dye.

In producing the above various preparations in the present invention, the compound of the present invention can be formulated to contain about 0.1 to 95% by weight, preferably about 0.5 to 90% by weight.

The above-prepared preparation may be used as it is or diluted with a carrier or water, but it can be freely diluted within the range of about 0.0001 to 100% by weight, preferably 0.001 depending on the purpose. It is preferable to use it by diluting it so as to contain 10% by weight of the active ingredient.

[0044]

[Examples] The following are production examples of raw material compounds as reference examples.
The present invention will be further clarified by listing the production examples of the compound of the present invention as examples and further adding test examples.

Reference Example 1 Preparation of 3,5-dichloro-N- (4-trifluoromethylphenyl) benzenesulfonamide p-aminobenzotrifluoride (1.61 g, 0.
01 mol) and pyridine (0.8 g, 0.011 mol)
Into a solution of toluene (45 ml) under stirring with 3,5-
Dichlorophenylbenzenesulfonyl chloride (2.4
Toluene (5 ml) solution of 6 g, 0.01 mol)
After the dropping, the reaction mixture was stirred at room temperature for 16 hours. Next, ethyl acetate (100 ml) was added, and the mixture was washed with 5% hydrochloric acid, then 5% sodium hydrogen carbonate, and finally with brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, the remaining solid was washed with n-hexane,
After suction filtration, it is dried to give the above-mentioned desired product (3.2
g, 85.8%) was obtained.

Reference Example 2 Preparation of 2,4,5-trichloro-N- (4-trifluoromethylphenyl) benzenesulfonamide p-Aminobenzotrifluoride (1.61 g, 0.
01 mol) and pyridine (0.8 g, 0.011 mol)
Into a solution of toluene (45 ml) under stirring 2,4,5
A solution of trichlorophenylbenzenesulfonyl chloride (2.82 g, 0.01 mol) in toluene (5 ml) was added dropwise at 10 ° C or lower, and after the addition, the reaction mixture was stirred at room temperature for 16 hours. Next, ethyl acetate (100 ml) was added, followed by washing with 5% aqueous hydrochloric acid solution, then 5% aqueous sodium hydrogen carbonate solution, and finally with brine, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the remaining solid was washed with n-hexane, suction-filtered and dried to obtain the above-mentioned desired product as white crystals in a yield of 73%.

Example 1 Preparation of N-propargyl-3,5-dichloro-N- (4-trifluoromethylphenyl) benzenesulfonamide 3,5-dichloro-N- (4-trifluoromethylphenyl) benzenesulfonamide (2.22 g, 0.00
6 mol) to 60% sodium hydride (0.27 g, 0.
(006 mol) was added little by little to a suspension of dimethylformamide (15 ml) at 10 ° C or lower. After adding the whole amount,
After stirring at room temperature for 30 minutes, propargyl bromide (1.18 g, 0.01 mol) in anhydrous benzene (5 m
1) The solution was added dropwise, and after the addition, the reaction mixture was stirred at room temperature for another 6 hours. Next, cold water was poured into the reaction system, the oil layer was extracted with benzene, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 1) to obtain the desired product (2.1
g, 85.4%).

¹ H-NMR (CDCl ₃ ) δ ppm; 2.
30 (1H, t), 4.48 (2H, d), 7.20-
7.78 (7H, m).

The compounds of Examples 2 to 45 below were obtained in the same manner as in Example 1 using appropriate starting materials.

Example 2 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a hydrogen atom, and Y is a trifluoromethyl group (4th position): Yellow oily ¹ H-NMR (CDCl ₃ ). δppm; 2.14 (1H,
t), 4.36 (2H, d), 6.96-7.78 (9
H, m).

Example 3 Compounds of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a hydrogen atom and Y is a chlorine atom (4th position): melting point 81-82 ° C. ¹ H-NMR (CDCl ₃ ) Δppm; 2.18 (1H,
t), 4.42 (2H, d,), 7.20-7.80.
(9H, m).

Example 4 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is hydrogen atom, and Y is chlorine atom (positions 3 and 5): melting point 99-101 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.24 (1H,
t), 4.42 (2H, d), 6.82-7.90 (8)
H, m).

Example 5 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is hydrogen atom and Y is fluorine atom (4th position): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.20 (1H,
t), 4.42 (2H, d), 6.78-7.86 (9
H, m).

Example 6 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a hydrogen atom, and Y is a nitro group (4th position): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.24 (1H,
t), 4.52 (2H, d), 7.24-8.32 (9
H, m).

Example 7 Compound of the general formula (1a) in which R ¹ is hydrogen atom, R ² is chlorine atom (2-position), X is hydrogen atom and Y is nitro group (4-position): Yellow oil ¹ H- NMR (CDCl ₃ ) δ ppm; 2.26 (1H,
t), 4.48 (2H, d), 7.20-8.38 (8)
H, m).

Example 8 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is chlorine atom (4th position), and Y is trifluoromethyl group (4th position): melting point 67-68 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.24 (1H,
t), 4.48 (2H, d), 7.22-7.78 (8)
H, m).

Example 9 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is chlorine atom (3-position) and Y is trifluoromethyl group (4-position): Yellow oil ¹ H-NMR (CDCl ₃ ) δppm; 2.30 (1H,
t), 4.48 (2H, d), 7.02-7.82 (8
H, m).

Example 10 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a methoxy group (4th position) and Y is a trifluoromethyl group (4th position): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.22 (1H,
t), 3.80 (3H, s), 4.48 (2H, d),
7.02-7.82 (8H, m).

Example 11 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a cyano group (4th position) and Y is a trifluoromethyl group (4th position): melting point 108-110 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm; 2.26 (1H,
t), 4.48 (2H, d), 7.24-7.76 (8)
H, m).

Example 12 R ¹ and R ² are hydrogen atoms, and X is a tert-butyl group (4
Position), Y is a trifluoromethyl group (4th position), a compound of the general formula (1a): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 1.30 (9H,
s), 2.26 (1H, t), 4.48 (2H, d),
7.24-7.76 (8H, m).

Example 13 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a nitro group (4th position) and Y is a trifluoromethyl group (4th position): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.26 (1H,
t), 4.52 (2H, d), 7.26-8.48 (8)
H, m).

Example 14 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 4).
Position), and a compound of the general formula (1a) in which Y is a trifluoromethyl group (4th position): melting point 97-99 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.28 (1H,
t), 4.48 (2H, d), 7.20-7.90 (7)
H, m).

Example 15 Compounds of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 2, 4 and 5) and Y is a trifluoromethyl group (position 4): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 2.30 (1 H,
t), 4.58 (2H, d), 7.38-7.78 (5
H, m), 8.0 (1H, s).

Example 16 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 5).
Position), and a compound of the general formula (1a) in which Y is a nitro group (4th position): melting point 96-97 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.50 (2H, d), 7.38-8.32 (7)
H, m).

Example 17 In the general formula (1a), R ¹ is a hydrogen atom, R ² is a fluorine atom (4th position), X is a chlorine atom (3rd and 5th positions), and Y is a nitro group (3rd position). Compound: melting point 94-95 ° C ¹ H-NMR (CDCl ₃ ) δppm; 2.26 (1H,
t), 4.50 (2H, d), 7.12-7.96 (6
H, m).

Example 18 R ¹ is a hydrogen atom, R ² is a chlorine atom (4th position), X is a chlorine atom (3rd and 5th positions), and Y is a trifluoromethyl group (3rd position).
A compound of the general formula (1a) which is: Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 2.33 (1 H,
t), 4.48 (2H, d), 7.26-7.80 (6
H, m).

Example 19 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (3 and 5
Position), Y is a trifluoromethyl group (3-position), a compound of the general formula (1a): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.34 (1H,
t), 4.48 (2H, d), 7.20-7.80 (7)
H, m).

Example 20 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 5)
Position) and Y is a fluorine atom (positions 3 and 4) (1)
Compound of a): Melting point 97-98 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.42 (2H, d), 6.92-7.62 (6)
H, m).

Example 21 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (3 and 5
Position) and Y is a fluorine atom (positions 2 and 4) (1)
Compound of a): melting point 81-82 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.28 (1H,
t), 4.40 (2H, d), 6.62-7.22 (6
H, m).

Example 22 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (3 and 5
Position), Y is a trifluoromethoxy group (4th position), a compound of the general formula (1a): melting point 87-89 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.48 (2H, d), 7.06-7.70 (7
H, m).

Example 23 A compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a chlorine atom (2-position, 4-position and 5-position), and Y is a trifluoromethyl group (3-position): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 2.32 (1 H,
t), 4.62 (2H, d), 7.20-8.22 (6)
H, m).

Example 24 In general, R ¹ is a hydrogen atom, R ² is a chlorine atom (4th position), X is a chlorine atom (2nd, 4th and 5th positions), and Y is a trifluoromethyl group (3rd position). Compound of formula (1a): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 2.30 (1 H,
t), 4.52 (2H, d), 7.38-8.10 (5
H, m).

Example 25 A compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a chlorine atom (2-position, 4-position and 5-position), and Y is a fluorine atom (2-position and 4-position). : Melting point 72-73 ° C ¹ H-NMR (CDCl ₃ ) δppm; 2.34 (1H,
t), 4.62 (2H, d), 6.62-8.04 (5
H, m).

Example 26 A compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a chlorine atom (2-position, 4-position and 5-position), and Y is a fluorine atom (3-position and 4-position). : Melting point 83-84 ° C ¹ H-NMR (CDCl ₃ ) δppm; 2.30 (1H,
t), 4.52 (2H, d), 6.80-8.06 (5
H, m).

Example 27 A general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a chlorine atom (2nd, 4th and 5th) and Y is a trifluoromethyl group (3rd and 5th). Compound: Melting point 99-100 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm; 2.40 (1 H,
t), 4.60 (2H, d), 6.40-8.26 (5
H, m).

Example 28 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 4)
Position), Y is a trifluoromethyl group (3 position), a compound of the general formula (1a): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.26 (1H,
t), 4.46 (2H, d), 7.26-7.90 (7)
H, m).

Example 29 R ¹ is hydrogen atom, R ² is chlorine atom (4th position), X is chlorine atom (3rd and 4th positions), Y is trifluoromethyl group (3rd position)
Compound of general formula (1a) which is: Melting point 112-114 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.30 (1H,
t), 4.44 (2H, d), 7.28-7.90 (6
H, m).

Example 30 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 4)
Position) and Y is a fluorine atom (positions 2 and 4) (1)
Compound of a): melting point 90-91 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.28 (1H,
t), 4.42 (2H, d), 6.68-7.96 (6)
H, m).

Example 31 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (3 and 4 positions).
Position), Y is a trifluoromethoxy group (4th position), a compound of the general formula (1a): melting point 101-102 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.24 (1H,
t), 4.40 (2H, d), 7.06 to 7.78 (7)
H, m).

Example 32 A general formula (R ¹ is a hydrogen atom, R ² is a fluorine atom (4th position), X is a chlorine atom (3rd, 4th and 5th positions), and Y is a nitro group (3rd position) ( Compound of 1a): melting point 118-119 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.56 (2H, d), 7.06-8.14 (5
H, m).

Example 33 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (2 and 5
Position), and a compound of the general formula (1a) in which Y is a trifluoromethyl group (position 4): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.30 (1H,
t), 4.62 (2H, d), 7.22 to 8.02 (7)
H, m).

Example 34 R ¹ and R ² are hydrogen atoms, and X is a trifluoromethyl group (3
Position), Y is a trifluoromethyl group (4th position), the compound of the general formula (1a): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.23 (1H,
t), 4.48 (2H, d), 7.20-8.10 (8
H, m).

Example 35 R ¹ and R ² are hydrogen atoms, and X is a trifluoromethyl group (3
Of the general formula (1a) in which Y is a trifluoromethyl group (4th position): melting point 128-130 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.42 (1H,
t), 4.56 (2H, d), 7.10-8.40 (8
H, m).

Example 36 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a fluorine atom (4th position) and Y is a trifluoromethyl group (4th position): melting point 57-58 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm; 2.22 (1H,
t), 4.48 (2H, d), 6.94-7.90 (8
H, m).

Example 37 Compound of the formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a fluorine atom (4th position), and Y is a fluorine atom (2nd and 6th positions): Yellow oil ¹ H- NMR (CDCl ₃ ) δppm; 2.18 (1H,
t), 4.36 (2H, d), 6.70-8.10 (6
H, m).

Example 38 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is cyano group (4th position) and Y is trifluoromethyl group (3rd position): melting point 103-104 ° C. ¹ H-NMR (CDCl ₃ ) δ ppm; 2.30 (1H,
t), 4.50 (2H, d), 7.30-7.88 (4
H, m).

Example 39 Compound of the general formula (1a) in which R ¹ is hydrogen atom, R ² is chlorine atom (4th position), X is cyano group (4th position), and Y is trifluoromethyl group (3rd position): Melting point 135-137 ° C ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.48 (2H, d), 7.38-7.68 (3
H, m), 7.78 (4H, s).

Example 40 Compound of the general formula (1a) in which R ¹ and R ² are hydrogen atoms, X is a cyano group (4th position) and Y is a fluorine atom (3rd and 4th positions): melting point 116-118 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.26 (1H,
t), 4.46 (2H, d), 6.98-7.80 (6
H, m).

Example 41 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 5)
Position) and Y is a (4-trifluoromethyl) -2-pyridyloxy group (4th position), a compound of the general formula (1a): melting point 108-111 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 2.20 (1H,
t), 4.42 (2H, d), 6.90-7.95 (9
H, m), 8.35 (1H, bs).

Example 42 R ¹ and R ² are hydrogen atoms, X is a chlorine atom (positions 3 and 4)
Position), Y is a (4-trifluoromethyl) -2-pyridyloxy group (4th position), a compound of the general formula (1a): melting point 140-141 ° C ¹ H-NMR (CDCl ₃ ) δppm; 2.32 (1H,
t), 4.42 (2H, d), 7.00-8.10 (9
H, m), 8.40 (1H, bs).

Example 43 R ¹ is a trifluoromethyl group (3rd position), R ² is a hydrogen atom,
X is a chlorine atom (4th position), Y is a trifluoromethyl group (3
Compound of the general formula (1a), which is a yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 2.30 (1H,
t), 4.48 (2H, d), 7.02-7.82 (7)
H, m).

Example 44 R ¹ and R ² are hydrogen atoms, and X is a trifluoromethyl group (3
Position and 5 position), Y is a trifluoromethyl group (3 position and 5 position)
A compound of the general formula (1a) which is a yellow oily yellow ¹ H-NMR (CDCl ₃ ) δ ppm; 2.28 (1 H,
t), 4.46 (2H, d), 7.02-7.92 (7)
H, m).

Example 45 R ¹ and R ² are hydrogen atoms, and X is a chlorine atom (3-position and 5-position).
Position), Y is a trifluoromethyl group (positions 3 and 5), a compound of the general formula (1a): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 2.30 (1 H,
t), 4.43 (2H, d), 6.98-7.88 (7)
H, m).

Example 46 N-Cyanomethyl-2,4,5-trichloro-N- (4
-Trifluoromethylphenyl) benzenesulfonamide 2,4,5-trichloro-N- (4-trifluoromethylphenyl) benzenesulfonamide (2.35 g,
0.006 mol) with 60% sodium hydride (0.2
7 g, 0.006 mol) of dimethylformamide (15
ml) was added little by little to the suspension solution at 10 ° C or lower. After adding the whole amount and stirring at room temperature for 30 minutes, bromoacetonitrile (1.20 g, 0.01 mol) of anhydrous benzene (5 m
1) The solution was added dropwise, and after the addition, the reaction mixture was stirred at room temperature for 5 hours. Next, cold water was poured into the system, the oil layer was extracted with benzene, and the extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (benzene: ethyl acetate = 20: 1) to obtain the desired product (3.02 g, 70%) as a pale yellow oil.

¹ H-NMR (CDCl ₃ ) δ ppm;
90 (2H), 7.62-8.02 (6H).

Using the appropriate starting materials and in the same manner as in Example 46, the compounds of Examples 47 to 65 below were obtained.

Example 47 R ³ 'is an ethoxy group and X'is a chlorine atom (3 and 5
Position), Y'is a fluorine atom (positions 3 and 4) and is represented by the general formula (1b): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 1.22 (3
H), 3.52 (2H), 4.96 (2H), 6.92
-7.70 (6H).

Example 48 R ³ 'is an ethoxy group and X'is a chlorine atom (3-position and 4-position).
Position), Y ′ is a trifluoromethyl group (positions 3 and 5), a compound of the general formula (1b): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 1.22 (3
H), 3.58 (2H), 5.04 (2H), 7.38
-8.10 (6H).

Example 49 R ³ 'is an ethoxy group and X'is a chlorine atom (3 and 4
Position), Y ′ is a chlorine atom (4th position) and a trifluoromethyl group (5th position), a compound of the general formula (1b): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 1.22 (3
H), 3.58 (2H), 5.04 (2H), 7.28
-7.90 (6H).

Example 50 Compound of the formula (1b) in which R ³ 'is an ethoxy group, X'is a chlorine atom (2nd, 4th and 5th) and Y'is a fluorine atom (3rd and 4th) : Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 1.22 (3
H), 3.62 (2H), 5.14 (2H), 6.82.
-7.96 (5H).

Example 51 Compound of the general formula (1b) in which R ³ 'is an ethoxy group, X'is a cyano group (4th position) and Y'is a trifluoromethyl group (3rd and 5th positions): Yellow oil ¹ 1 H-NMR (CDCl ₃ ) δppm; 1.20 (3
H), 3.52 (2H), 5.02 (2H), 7.20
-7.98 (7H).

Example 52 R ³ 'is an ethoxy group, X'is a chlorine atom (2nd, 4th and 5th positions) and Y'is a trifluoromethyl group (3rd and 5th positions).
A compound of the general formula (1b) which is: Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 1.24 (3
H), 3.68 (2H), 5.20 (2H), 7.60.
-8.08 (5H).

Example 53 R ³ 'is a methoxy group and X'is a trifluoromethyl group (3
Position and 5 position), a compound of the general formula (1b) in which Y ′ is a trifluoromethyl group (4 position): Yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 3.42 (3
H), 4.96 (2H), 7.02-8.46 (7)
H).

Example 54 R ³ 'is an ethoxy group and X'is a trifluoromethyl group (3
Compounds of the general formula (1b) in which Y ′ is a trifluoromethyl group (4th position): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 1.20 (3
H), 3.62 (2H), 5.20 (2H), 7.02.
-8.42 (7H).

Example 55 R ³ 'is a cyano group, X'is a chlorine atom (positions 3 and 5),
Y'is a chlorine atom (4th position) and a trifluoromethyl group (5
A compound of the general formula (1b), which has a melting point of 113-115 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 4.76 (2)
H), 7.32-7.90 (6H).

Example 56 R ³ 'is a cyano group and X'is a chlorine atom (2-position, 4-position and 5-position).
Position), Y ′ is a trifluoromethyl group (positions 3 and 5) of the general formula (1b): melting point 117-119 ° C. ¹ H-NMR (CDCl ₃ ) δppm; 4.90 (2
H), 7.42-8.26 (5H).

Example 57 Compound of the general formula (1b) in which R ³ 'is a cyano group, X'is a trifluoromethyl group (positions 3 and 5), and Y'is a trifluoromethyl group (position 4): melting point 124-126 ° C ¹ H-NMR (CDCl ₃ ) δppm; 4.90 (2
H), 7.02-8.10 (7H).

Example 58 A compound represented by the general formula (1) in which R ³ 'is a cyano group, X'is a trifluoromethyl group (positions 3 and 5), and Y'is a cyano group (position 4)
Compound of b): Yellow pasty ¹ H-NMR (CDCl ₃ ) δppm; 4.92 (2
H), 6.98-8.12 (7H).

Example 59 A compound represented by the general formula (1) in which R ³ 'is a cyano group, X'is a trifluoromethyl group (positions 3 and 5), and Y'is a nitro group (position 4)
Compound of b): Yellow pasty ¹ H-NMR (CDCl ₃ ) δppm; 4.92 (2
H), 7.04-8.26 (6H).

Example 60 R ³ 'is a cyano group, X'is a trifluoromethyl group (positions 3 and 5), and Y'is a trifluoromethyl group (positions 3 and 5).
Compound of the general formula (1b), which is a yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 4.90 (3
H), 7.20-8.42 (6H).

Example 61 R ³ 'is a cyano group and X'is a trifluoromethyl group (4
Position), Y ′ is a chlorine atom (2 position) and a nitro group (4 position), a compound of the general formula (1b): yellow pasty ¹ H-NMR (CDCl ₃ ) δppm; 4.90 (2
H), 7.22-8.38 (7H).

Example 62 R ³ 'is a cyano group and X'is a trifluoromethyl group (4
Position), Y ′ is a trifluoromethyl group (position 4), a compound of the general formula (1b): yellow oily ¹ H-NMR (CDCl ₃ ) δppm; 4.90 (2
H), 7.28-8.43 (8H).

Example 63 R ³ 'is an ethoxycarbonyl group and X'is a chlorine atom (2
Position, 4 position and 5 position), Y'is a trifluoromethyl group (3
Compound of the general formula (1b) which is in the 1-position and 5-position): Yellow pasty ¹ H-NMR (CDCl ₃ ) δppm; 1.20 (3
H), 4.10 (2H), 4.50 (2H), 7.60
-8.06 (5H).

Example 64 A compound of the general formula (1b) in which R ³ 'is an ethoxycarbonyl group, X'is a trifluoromethyl group (positions 3 and 5), and Y'is a trifluoromethyl group (position 4): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 1.22 (3
H), 4.10 (2H), 4.52 (2H), 7.04.
-8.40 (7H).

Example 65 A compound of the general formula (1b) in which R ³ 'is a methoxycarbonyl group, X'is a trifluoromethyl group (positions 3 and 5) and Y'is a trifluoromethyl group (position 4): Yellow oily ¹ H-NMR (CDCl ₃ ) δ ppm; 3.98 (3
H), 4.52 (2H), 7.02-8.40 (7
H).

Test Example 1 (Test on Nite Mites) 2 parts by weight of the compound of the present invention was dissolved in 98 parts by weight of acetone. This was diluted to a predetermined concentration with an aqueous solution containing 0.04% spreader (Nippon Pesticides Shin-Rinoh) to prepare a solution. Potted kidney beans were inoculated with adults of the spider mite, and then the solution prepared above was sprayed until dripping. The death rate after 4 days was measured, and the results are shown in Table 1 and Table 2.
Shown in Test compound Nos. In these tables Corresponds to the example number. The same applies to Tables 3 to 5 below.

[0117]

[Table 1]

[0118]

[Table 2]

Test Example 2 (Test on diamondback moth) 2 parts by weight of the compound of the present invention was dissolved in 98 parts by weight of acetone. This was diluted to a predetermined concentration with an aqueous solution containing 0.04% spreader (Nippon Pesticides Shin-Rinoh) to prepare a solution. 7
A piece of cabbage leaf of cm × 7 cm was immersed in the solution prepared above for 10 seconds. Put 4th instar larvae of Plutella xylostella along with the leaf pieces treated above in a plastic cup having a diameter of 13 cm,
It was left standing in a thermostatic chamber at 25 ± 1 ° C. The death rate after 2 days and the emergence suppression rate after 7 days were measured, and the results are shown in Tables 3 and 4.
Shown in The evaluation of the emergence suppression rate was A: 100%, B:
90% or more and less than 100%, C: 50% or more and less than 90%, and D: less than 50%.

[0120]

[Table 3]

[0121]

[Table 4]

Test Example 3 (Test on Sweetpotato Nematodes) 1 mg of the compound of the present invention was dissolved in 100 μl of acetone.
9900 μl of an aqueous solution containing 0.1% Tween 80
Was added to prepare 10 ml of solution.

100 to 20 mesh sand (river sand) 8 dried in a 10 ml sample bottle at 120 ° C. for 3 hours
g, 2nd stage larvae of Lactobacillus subtilis (L2) 5
1 ml of a nematode suspension containing 00 individuals and 1 ml of the above-prepared solution (concentration of the compound of the present invention: 100 ppm) were placed in that order, and left in a thermostat (dark) at 25 ° C. for 24 hours. Then, the tomato seedlings from which the root system was removed (when the first true leaf was developed) were inserted into the sand for a few mm and allowed to stand in a 25 ° C assay chamber. Processing 1
Four days later, the roots were washed with water, the number of root knots was investigated, and the control rate was calculated. Table 5 shows the results.

[0124]

[Table 5]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location C07C 321/28 C07C 321/28 (72) Inventor Seiichi Wakizaka 615 Satoura-cho, Satoura-cho, Naruto-shi, Tokushima Prefecture Address: Otsuka Chemical Co., Ltd., Naruto Laboratory (72) Inventor, Hisashi Takao, 615, flower face, Satoura-cho, Satoura-cho, Naruto City, Tokushima Prefecture

Claims (2)

[Claims] 1. A compound of the general formula [Wherein R ¹ and R ² are the same or different and each represents a hydrogen atom,
A lower haloalkyl group or a halogen atom is shown. R ³ is
An ethynyl group, a cyano group, a lower alkoxy group or a lower alkoxycarbonyl group is shown. X and Y may be the same or different and each may have a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a phenoxy group which may have a substituent, or a substituent. A phenyl group, a pyridyloxy group which may have a substituent, a cyano group, a nitro group, a lower alkylthio group or a lower alkylsulfonyl group is shown. m and n each represent an integer of 1 to 3. ] The sulfonamide derivative represented by these. 2. An insecticidal, acaricidal and nematicidal agent containing the sulfonamide derivative according to claim 1 as an active ingredient.