JPH0559017A - 1,2,3-triazole derivative, its production and noxious organism controlling agent - Google Patents

Abstract

PURPOSE:To obtain new 1,2,3-triazole derivatives having remarkable controlling activity against noxious organisms. CONSTITUTION:1,2,3-Triazole derivatives expressed by formula I [R<1> is H, halogen, 1-6C alkyl or phenyl; R<2> is 1-15C alkyl, benzyl, CH2COOR<5> (R<5> is alkyl), CH2CON(R<5>)2, pyridyl, 3-5C alkyenyl, 3-5C alkynyl, 1-4C alkyl, CH2CH2OR<5> or CH2CH2OCH2CH2OR<5>; R<3> is H, 1-4C alkyl or phenyl; R<4> is H or 1-4C alkyl or R<4> and R<5> alkylene which may have O; n is 0-2], e.g. 1-(N,N- dimethylcarbamoyl)-5-methylmercapto-1,2,3-triazole. The compound in which n is 0 in the compounds expressed by formula I is obtained by reacting a compound expressed by formula II with a compound expressed by formula III.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel 1,2,3-triazole derivative useful as a pest control agent and a method for producing the same.

[0002]

Description of the Prior Art Since the 1,2,3-triazole derivative of the present invention is a novel compound, its pest control activity is not known.

[0003]

The object of the present invention is to provide a novel
The object of the present invention is to provide a 2,3-triazole derivative, a method for producing the same, and a pest control agent containing the same as an active ingredient.

[0004]

Means for Solving the Problems As a result of intensive research to solve the above problems, the present inventors
The inventors have found that the 3-triazole derivative has a remarkable control activity against pests, and have completed the present invention. That is, the present invention is as follows. The first invention is
Compound (I) of the following formula:

[0005]

[Chemical 8]

(Wherein R ¹ is a hydrogen atom, a halogen atom,
Represents an alkyl group having 1 to 6 carbon atoms or a phenyl group which may have a substituent; R ² represents 1 to 15 carbon atoms
Alkyl group, a benzyl group which may have an alkyl group having 1 to 6 carbon atoms _of, -CH _² COOR _5, -CH ²
CON (R ⁵ ) ₂ , halogen atom or carbon atom 1
~ 4 pyridyl group optionally having a haloalkyl group,
An alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms which may have a cyano group,- CH ₂ CH ₂ oR ^5, or _-CH 2 CH ₂
Represents OCH ₂ CH ₂ OR ⁵ (provided that R ⁵ represents an alkyl group having 1 to 4 carbon atoms); R ³ has a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a halogen atom. Optionally represents a phenyl group; R ⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or, R ³ and R ⁴ represent a carbon which may have one oxygen atom. It represents an alkylene group having 2 to 6 atoms; n represents 0, 1, or 2. ) Related to the 1,2,3-triazole derivative. The second invention relates to a compound (I
I):

[0007]

[Chemical 9]

(Wherein R ¹ and R ² have the same meanings as described above) and the compound of the following formula (II
I):

[0009]

[Chemical 10]

(Wherein R ³ and R ⁴ have the same meanings as described above; X represents a leaving group), and the compound represented by the above formula (I) is reacted. In the following formula (I-1):

[0011]

[Chemical 11]

The present invention relates to a process for producing a 1,2,3-triazole derivative represented by the formula (wherein R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above). A third invention is a compound (II) represented by the following formula:

[0013]

[Chemical formula 12]

(Wherein R ¹ and R ² are as defined above) and the compound (IV) of the following formula:

[0015]

[Chemical 13]

(Wherein R ³ has the same meaning as described above), the compound represented by the formula (I) is represented by the following formula (I-2):

[0017]

[Chemical 14]

The present invention relates to a method for producing a 1,2,3-triazole derivative represented by the formula (wherein R ¹ , R ² and R ³ are as defined above).

A fourth aspect of the present invention is characterized in that the 1,2,3-triazole derivative represented by n in the above-mentioned formula (I) is reacted with a peroxide. The present invention relates to a method for producing a 1,2,3-triazole derivative in which n in 1) is 1 or 2.

A fifth aspect of the present invention relates to a pest control agent containing the 1,2,3-triazole derivative represented by the above formula (I) as an active ingredient.

The present invention will be described in detail below. The novel 1,2,3-triazole derivative [compound (I)], which is the above-mentioned target compound, and a raw material for the production thereof
I), compound (III) and compound (IV)], R ¹ , R ² , R ³ , R ⁴ , X and n are as follows.

R ¹ is a hydrogen atom, a halogen atom,
Examples thereof include a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group which may have a substituent and the like; a halogen atom (for example, a chlorine atom, an iodine atom,
(Bromine atom, fluorine atom, etc.), preferably chlorine atom, bromine atom;
4 is preferable, preferably methyl group, ethyl group, n-
Propyl group and t-butyl group are preferred.

R ² is an alkyl group having 1 to 15 carbon atoms, a benzyl group optionally having an alkyl group having 1 to 6 carbon atoms, —CH ₂ COOR ⁵ , or —CH ₂ CON.
(R ⁵ ) ₂ , a pyridyl group optionally having a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, and a carbon atom. C1-4 haloalkyl group, or an alkyl group having 1 to 4 carbon atoms which may atoms have a cyano _{^{group, -CH 2 CH 2 oR 5,}} -CH 2 CH 2 OCH 2 C
And the like H ₂ OR ⁵ (provided that, ^{R 5} represents an alkyl group having 1 to 4 carbon atoms.).

The alkyl group, alkenyl group and alkynyl group for R ² may be linear or branched; and the alkyl group having 1 to 15 carbon atoms is preferably carbon atom. The alkyl group optionally having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms; the benzyl group may have 1 to 5 carbon atoms, more preferably t-butyl. The basis is good.

As the halogen atom (eg, chlorine atom, iodine atom, bromine atom, fluorine atom, etc.) which may be possessed by the pyridyl group of R ² , chlorine atom is preferred; Optionally 1 to 1 carbon atoms
4 haloalkyl groups (eg, chlorine atom, iodine atom,
As the linear or branched one having a halogen atom such as a bromine atom or a fluorine atom, a linear or branched one having 1 to 4 carbon atoms is preferable, and a trifluoromethyl group is more preferable. As the alkenyl group having 3 to 5 carbon atoms (for example, allyl group, 1- or 2-butenyl group, 1- or 2-methylallyl group, 2-pentenyl group, isoprenyl group, etc.), an allyl group is preferable. The alkynyl group having 3 to 5 carbon atoms (eg, 1- or 2-propynyl group, 2-butynyl group, etc.) is preferably 2-propynyl group.

Here, R ⁵ has 1 to 4 carbon atoms.
The straight-chain or branched alkyl group (for example, the alkyl group described above) can be mentioned, but preferably has 1 to 3 carbon atoms, and more preferably has 1 to 2 carbon atoms. Is good.

R ³ is a hydrogen atom or a carbon atom of 1 to 1
4 alkyl group, a phenyl group which may have a halogen atom and the like can be mentioned; the alkyl group having 1 to 4 carbon atoms (for example, the alkyl groups described above) is preferably a carbon atom. The one having 1 to 3 carbon atoms, more preferably the one having 1 to 2 carbon atoms is preferable; the halogen atom which the phenyl group may have (for example, the halogen atom described above) is preferably a chlorine atom. Is good.

R ⁴ is a hydrogen atom or a carbon atom number of 1 to
4 alkyl groups and the like; 1 carbon atom
The alkyl group having 4 to 4 (for example, the alkyl groups described above) preferably has 1 to 3 carbon atoms, and more preferably 1 to 2 carbon atoms.

Alternatively, R ³ and R ⁴ are alkylene groups having 2 to 6 carbon atoms which may have one oxygen atom (eg, tetramethylene, pentamethylene, 3-oxapentamethylene, 2 , 4-dimethyl-3-oxapentamethylene, etc.); the number of oxygen atoms is preferably 1; the number of carbon atoms is preferably 3 to 5, more preferably 4 to 5 Is good.

The leaving group X is not particularly limited, and includes, for example, a halogen atom (eg, iodine halogen atom described above), an alkylthio group (eg, methylthio, ethylthio, propylthio, butylthio, etc.), halogen. Examples of the optionally substituted alkanesulfonyloxy group (eg, methanesulfonyloxy, ethanesulfonyloxy, trifluoromethanesulfonyloxy, etc.), arylsulfonyloxy group (eg, benzenesulfonyloxy, p-toluenesulfonyloxy, etc.) You can

As n, an integer of 0 to 2 can be mentioned, and 0 is preferable.

The compound (I) can be synthesized by the production method A, B or C. (Production Method A) In order to synthesize the target compound (I), the starting compound (II) and compound (III) are usually used as a solvent in order to facilitate the reaction by capturing the eliminated compound H-X. The reaction can be carried out in a medium or in the absence of a solvent (in the absence of a solvent, these raw materials are dissolved by heating); preferably, the reaction is carried out in a solvent in the presence of a base.

The solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroine, hexane, chlorobenzene, dichlorobenzene, methylene chloride, Chlorinated or unchlorinated aromatics such as chloroform, dichloromethane, dichloroethane, trichloroethylene, cyclohexane, aliphatics,
Alicyclic hydrocarbons; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc .; ketones such as acetone, methyl ethyl ketone, etc .; nitriles such as acetonitrile, propionitrile, etc .;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and the like; organic bases such as triethylamine, pyridine, N, N-dimethylaniline and the like; 1,3-dimethyl-2-imidazolidinone; dimethyl Sulfoxide; a mixture of the above solvents and the like can be mentioned.

The amount of the solvent used is the compound (I
The compound (II) can be used so that the concentration of I) falls within the range of 5 to 80% by weight, preferably the compound (II).
It is preferable to use it so that the concentration thereof is 10 to 70% by weight.

Examples of the base include organic bases such as triethylamine, pyridine and N, N-dimethylaniline; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; sodium amide, sodium hydroxide and water. Inorganic bases such as potassium oxide, potassium carbonate, sodium carbonate, sodium hydride and the like can be mentioned.

The amount of the compound (II) used can be 0.5 to 5 times mol.

The reaction temperature is not particularly limited, but is usually within the temperature range from room temperature to the boiling point of the solvent used,
It is preferable to heat within the temperature range below the boiling point. The reaction time varies depending on the above concentration and temperature, but is usually 1
~ 5 hours.

The amount of the raw material compound used is 0.5 to 2 times the molar amount of the compound (III) with respect to the compound (II).
It is preferably 0.8 to 1.5 times the molar amount.

The compound (II) used in the present invention is, for example, 5-mercapto- in a solvent such as anhydrous tetrafuran.
Salts of 1,2,3-triazole derivatives and haloalkyl groups [for example, those having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms (the halogen atom is preferably iodine atom or bromine atom)] It can be obtained by reacting with. After completion of the reaction, the compound (II) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration, and optionally purified by a known means such as recrystallization and various chromatography. can do.

As the compound (II), for example, Table 4 to
Each compound (I) consisting of the type of each substituent shown in 11
[Referred to as compounds 1-60. ] Each compound (II) [compound (II) ₁ to (I
I) ₆₀ . ] Can be mentioned [for example,
Compound (II) corresponding to Compound 1 is converted to Compound (II) ₁
Called. The compound (II) ₁ is the compound (I
In the formula I), R ¹ is a hydrogen atom and R ² is CH.
Means ₃ . ].

Compound (III) can be prepared according to, for example, J. Or
g. Chem. , Vol. 5, p. 306 (1940), according to the method. As the compound (III), for example, each compound (III) consisting of the kinds of substituents corresponding to the compounds 1, 2, 4, 15, 18, 28, 31, 32, etc. shown in Tables 4 to 11.
[Compound (III) ₁ , (III) ₂ , (III) ₄ ,
(III) ₁₅ , (III) ₁₈ , (III) ₂₈ ,
_These are referred to as (III) ₃₁ , (III) _{32 and the} like. ] (For example, compound (III) corresponding to compound ₁ is referred to as compound (III) ₁ . Further, the compound (III) ₁ means that in the formula represented by the compound (III), R ³ and R ⁴ are CH ₃ , and X is a leaving group (for example,
Halogen atom such as chlorine atom) is meant. ].

The desired compound (I) produced as described above is a 1,2,3-triazole derivative in which n is 0, and after the completion of the reaction, it is usually subjected to extraction, concentration, filtration and the like. After the treatment, it can be appropriately purified by a known means such as recrystallization and various chromatographies, if necessary.

(Production Method B) The target compound (I) is synthesized by
Using compound (IV) instead of compound (III),
It can be carried out by reacting under the same conditions as in production method A. In addition, triethylamine or the like can be used as a catalyst to accelerate the reaction.

Compound (IV) can be prepared according to, for example, J. Am. C
hem. Soc. , 72, 1888 (1950)
It can be easily produced according to the method described in 1.
Examples of the compound (IV) include, for example, compounds (IV) [compounds (IV) ₃ and (IV) ₁₆ consisting of the types of substituents corresponding to the compounds 3 and 16 shown in Tables 4 to 11 and the like.
And so on. ] [For example, the compound (IV) corresponding to the compound ₃ is referred to as the compound (IV) ₃ . The compound (IV) ₃ is the compound (IV)
It means that R ^{3 in the} formula represented by is CH ₃ . ].

The desired compound (I) produced as described above is a 1,2,3-triazole derivative in which R ⁴ is a hydrogen atom. After completion of the reaction, it is usually extracted, concentrated, filtered or the like. After the post-treatment, it can be appropriately purified by known means such as recrystallization and various chromatographies, if necessary.

(Production Method C) The target compound (I) is synthesized by
It can be produced by reacting a 1,2,3-triazole derivative represented by n of 0 with a peroxide in a solvent. The peroxide is not particularly limited, and examples thereof include hydrogen peroxide, m-chloroperbenzoic acid, sodium metaperiodate, potassium permanganate, sodium hypochlorite and the like.

As the solvent, the same solvent as in the production method A can be used. The reaction temperature may be within the temperature range from -10 ° C to the boiling point of the solvent used or less, preferably -10 ° C to room temperature.

The desired compound (I) produced as described above is a 1,2,3-triazole derivative in which n is 1 or 2, and is usually extracted, concentrated, filtered or the like after completion of the reaction. After the post-treatment, it can be appropriately purified by known means such as recrystallization and various chromatographies, if necessary.

Examples of the target compound (I) produced by these production methods A, B or C include, for example, each compound (I) [compound 1 consisting of the kind of each substituent shown in Tables 4 to 11]. -60. ] Can be mentioned [for example,
Compound 1 means that in the formula represented by the compound (I), R ¹ is a hydrogen atom, R ² is CH ₃ , R ³ and R ⁴ are CH ₃ , and n is 0. ].

The pests which can be controlled by the compound (I) of the present invention include agricultural and horticultural pests [eg, Hemiptera (Plants, leafhoppers, aphids, whiteflies, etc.), Lepidoptera (Beetle beetles). , Diamondback moth, leaf beetle, leaf moth, scabbard beetle, etc.), Coleoptera (Galloridae, Weevil, Chrysomelidae, Chafer, etc.) )], Sanitary pests (for example, flies, mosquitoes, cockroaches, etc.), stored-grain pests (Beetle beetles, bean weevils, etc.), root-knot nematodes, pine wood nematodes, mite, and the like. For example, wheat leaf rust, barley powdery mildew, cucumber downy mildew, rice blast, toma Epidemics, etc.) can be mentioned.

The pest control agent of the present invention is used for remarkable insecticidal
It has acaricidal and bactericidal effects and contains one or more compounds (I) as active ingredients. Compound (I)
Can be used alone, but is usually mixed with a carrier, a surfactant, a dispersant, an auxiliary agent, etc. by a conventional method (for example, powders, emulsions, fine granules, granules, wettable powders, oily preparations). (Prepared as a composition such as a suspension or an aerosol) is preferably used.

Examples of the carrier include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonization. Hydrogen (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene) Liquid carriers such as glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection) out and the like.

Examples of surfactants and dispersants that can be used to improve the performance of the present agent such as adhesion to animals and plants, improvement of absorption, dispersion of drug, emulsification, spread and the like include, for example, alcohol sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethyl cellulose, polyethylene glycol, gum arabic or the like can be used as an auxiliary agent.

In the production of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in suitable combination according to the purpose.
The concentration of the active ingredient in the case where the compound (I) of the present invention is formulated is usually 1 to 50% by weight in an emulsion and 0.3 in a powder.
25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, usually 0.5 to 5% by weight for oils, usually 0.1 to 5% by weight for aerosols. is there.

These formulations can be diluted to an appropriate concentration and sprayed on the foliage of plants, soil, water surface of paddy fields or directly applied for various purposes depending on the purpose.

[0056]

EXAMPLES The present invention will be specifically described below with reference to examples and examples. It should be noted that these examples do not limit the scope of the present invention. Reference Example 1 [Synthesis of Compound (II)]

(1) 5-Methylmercapto-1,2,3
-Synthesis of triazole (raw material compound 1) 5-mercapto-1,2,3-triazole sodium salt (30.0
g) was dissolved in anhydrous tetrahydrofuran (250 ml), methyl iodide (27.0 g) was added dropwise under stirring at room temperature, and the mixture was further stirred for 1 hr to cause reaction. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 27.0 g of the target raw material compound 1 as reddish brown crystals.

(2) 5-propylmercapto-1,2,
Synthesis of 3-triazole (raw material compound 4) 5-Mercapto-1,2,3-triazole sodium salt (5.0 g) was added to anhydrous tetrahydrofuran (20 ml).
And propyl iodide (5.9 g) was added dropwise with stirring at room temperature, and the mixture was further heated under reflux for 1 hour for reaction.
After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate =
(9: 1 elution) to obtain 4.4 g of the desired starting material compound 4 as a colorless oil.

(3) 5-n-octyl mercapto-1,
Synthesis of 2,3-triazole (raw material compound 7) 5-mercapto-1,2,3-triazole sodium salt (4.9 g) was added to anhydrous tetrahydrofuran (20 ml).
And n-octyl bromide (8.5
After g) was added dropwise, the mixture was heated under reflux for 3 hours for reaction. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. By adding n-hexane to the obtained oily matter, 6.3 g of the desired starting material compound 7 as a colorless crystal was obtained.

(4) Synthesis of 4-methyl-5-methylmercapto-1,2,3-triazole (starting compound 15) 4-Methyl-5-mercapto-1,2,3-triazole (1.15 g) Anhydrous tetrahydrofuran (20m
It was dissolved in 1), triethylamine (1.21 g) and methyl iodide (1.15 g) were added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, wash this extract with water,
After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was isolated by silica gel column chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 4: 1) to obtain 1.1 g of the desired starting material compound 15.

(5) Synthesis of other raw material compounds (II) in Tables 1 to 3 Raw material compounds (II) were synthesized in the same manner as the synthesis method of any one of the above (1) to (4).

[0062]

[Table 1]

[0063]

[Table 2]

[0064]

[Table 3]

Example 1 [Synthesis of Compound (I)] The starting compound (II) obtained in Reference Example 1 was used to synthesize the target compound (I) by the production method A, B or C. (1) Synthesis of 1- (N, N-dimethylcarbamoyl) -5-methylmercapto-1,2,3-triazole (Compound 1) In Production Method A, the target compound (I-1) was prepared as follows. I was able to get it. 5-methyl mercapto-1,2,3
-Triazole (1.2g) in acetonitrile (20m
l), potassium carbonate (2.2 g) and N, N-dimethylcarbamoyl chloride (1.23 g) were added,
The mixture was heated under reflux for 5 hours with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 9: 1 elution) to obtain 1.55 g of the target compound 1 as a pale yellow oily substance.

(2) 4-Brom-1- (N, N-dimethylcarbamoyl) -5-methylmercapto-1,2,3
-Synthesis of Triazole (Compound 2) With Production Method A, the target compound (I) could be obtained as follows. 4-Brom-5-methylmercapto-
1,2,3-triazole (1.5 g) was dissolved in N, N-dimethylformamide (20 ml), potassium carbonate (1.6 g) and N, N-dimethylcarbamoyl chloride (0.91 g) were added, The mixture was heated under reflux at 100 ° C. for 5 hours with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene:
Ethyl acetate = 9: 1 elution) to obtain 1.6 g of the target compound 2 as a pale yellow oily substance.

(3) 2- (N-methylcarbamoyl)-
Synthesis of 5-Methylmercapto-1,2,3-triazole (Compound 6) By the production method B, the target compound (I-2) could be obtained as follows. 5-methyl mercapto-1,2,3
-Triazole (1.15g) in acetonitrile (10
ml) and methylisocyanate (0.68 g)
Was added. Then, a catalytic amount of triethylamine was added and stirred at about 40 ° C. for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wakogel C-200, toluene:
Ethyl acetate = 9: 1 elution) to obtain 0.55 g of the target compound 6 as colorless crystals.

(4) Synthesis of 1- (N, N-dimethylcarbamoyl) -5-n-octylmercapto-1,2,3-triazole (Compound 15) In Production Method A, the target compound ( I) could be obtained. 5-n-octyl mercapto-1,2,
3-triazole (1.5 g) was added to acetonitrile (20
ml), potassium carbonate (1.45 g) and N, N
-Dimethylcarbamoyl chloride (0.86 g) was added, and the mixture was heated under reflux for 3 hours with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate.
Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C
-200, toluene: ethyl acetate = 9: 1 elution) to obtain the target compound 15 as a pale yellow oily substance in 1.4.
5 g was obtained.

(5) 5-benzylmercapto-1-
Synthesis of (N, N-dimethylcarbamoyl) -1,2,3-triazole (Compound 18) With the production method A, the target compound (I) could be obtained as follows. 5-benzylmercapto-1,2,3-
Triazole (2.0 g) with acetonitrile (20 m
1) dissolved in potassium carbonate (2.14 g) and N, N-
Dimethylcarbamoyl chloride (1.24 g) was added, and the mixture was heated under reflux for 3 hours with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate.
Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained oily substance was subjected to silica gel column chromatography (Wako Gel C
-200, eluting with toluene: ethyl acetate = 9: 1) to obtain 2.2 of the target compound 18 as a pale yellow oily substance.
3 g was obtained.

(6) 1- (N, N-dimethylcarbamoyl) -5- (2-ethoxyethyl) mercapto-1,
Synthesis of 2,3-triazole (Compound 28) By the production method A, the target compound (I) could be obtained as follows. 5- (2-Ethoxyethyl) mercapto-1,2,3-triazole (1.15 g) was dissolved in acetonitrile (20 ml), and potassium carbonate (2.0
g) and N, N-dimethylcarbamoyl chloride (1.1
8 g) was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was isolated by silica gel column chromatography (Wakogel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 1.0 g of the target compound 28.

(7) 1- (N-pyrrolidinocarbamoyl) -5-methylmercapto-1,2,3-triazole (Compound 31) and 2- (N-pyrrolidinocarbamoyl) -5-methylmercapto-1, Synthesis of 2,3-triazole (Compound 32) By the production method A, the target compound (I) could be obtained as follows. 5-Methylmercapto-1,2,3-triazole (2.3 g) was added to acetonitrile (30 ml).
Was dissolved in water, potassium carbonate (4.0 g) and N-pyrrolidinocarbamoyl chloride (2.94 g) were added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, after washing this extract with water and drying with anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure. The obtained residue was isolated by silica gel column chromatography (Wako Gel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 1.4 g of the target compound 31 and 1.0 g of the target compound 32.

(8) 1- (N-carbamoyl) -5-methylmercapto-1,2,3-triazole (Compound 3
Synthesis of 6) By the production method B, the target compound (I) could be obtained as follows. 5-Methylmercapto-1,2,3-triazole (1.15 g) was mixed with acetic acid (20 ml) and water (1
It was dissolved in a mixed solution with 0 ml), sodium isocyanate (0.71 g) was added, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the produced precipitate was filtered, washed with water and dried to obtain 0.8 g of the target compound 36.

(9) 1- (N, N-dimethylcarbamoyl) -4-methyl-5-methylmercapto-1,2,3
-Synthesis of Triazole (Compound 4) In the production method A, the target compound (I) could be obtained as follows. 4-methyl-5-methylmercapto-
1,2,3-triazole (1.29 g) was dissolved in acetonitrile (20 ml), potassium carbonate (2.0 g)
And N, N-dimethylcarbamoyl chloride (1.18
g) was added and the mixture was stirred at room temperature for 5 hours. After the reaction,
The solvent was distilled off under reduced pressure, and the target compound was extracted with ethyl acetate. Then, this extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was isolated by silica gel column chromatography (Wako Gel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 1.90 g of the target compound 4.

(10) 1- (N, N-dimethylcarbamoyl) -5-methylsulfinyl-1,2,3-triazole (Compound 39) and 1- (N, N-dimethylcarbamoyl) -5-methylsulfonyl- Synthesis of 1,2,3-triazole (Compound 40) By the production method C, the target compound (I) could be obtained as follows. 1- (N, N-dimethylcarbamoyl)
-5-Methylmercapto-1,2,3-triazole (2.0 g) was dissolved in dichloromethane (20 ml),
M-Chloroperbenzoic acid (3.48 g) was added under ice-cooling stirring, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the deposited precipitate was filtered off, and the filtrate was extracted with dichloromethane. The extract was washed with a saturated sodium hydrogen carbonate solution and then with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was isolated by silica gel column chromatography (Wako gel C-200, toluene: ethyl acetate = 1: 1, then ethyl acetate) to isolate 1.90 g of the desired compound 39 and 40 of the desired compound.
Was obtained.

(11) Synthesis of other compounds (I) in Tables 4 to 11 The desired compound (I) was synthesized in the same manner as in the synthesis method of any one of the above (1) to (10).

[0076]

[Table 4]

[0077]

[Table 5]

[0078]

[Table 6]

[0079]

[Table 7]

[0080]

[Table 8]

[0081]

[Table 9]

[0082]

[Table 10]

[0083]

[Table 11]

Example 2 [Preparation of preparation] (1) Preparation of granules 5 parts by weight of compound 1, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of neoperex powder (trade name; manufactured by Kao Corporation) And 2 parts by weight of sodium lignin sulfonate were uniformly mixed, and then a small amount of water was added and kneaded, then granulated and dried to obtain a granule.

(2) Preparation of wettable powder 10 parts by weight of compound 1, 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) and demol (product) Name; manufactured by Kao Co., Ltd.)
Then, it was pulverized to obtain a wettable powder.

(3) Preparation of emulsion To 20 parts by weight of compound 1 and 70 parts by weight of xylene, 10 parts by weight of toxanone (trade name; manufactured by Sanyo Kasei Co., Ltd.) were added and uniformly mixed and dissolved to obtain an emulsion. ..

(4) Preparation of Dust Preparation 5 parts by weight of compound 1, 50 parts by weight of talc and 4 of kaolin
A powder was obtained by uniformly mixing 5 parts by weight.

Example 3 [Efficacy test] (1) Efficacy test against female adult worms of the genus Nami, each wettable powder of compound (I) shown in Tables 4 to 11 prepared according to Example 3 was treated with a surfactant (0. Diluted to 1000 ppm with water containing 0.01%) and added 10% to each of these chemicals.
Each kidney bean leaf piece (20 mm in diameter) infested with adult female adults of the head mite was immersed for 15 seconds. Next, these leaf pieces were left in a constant temperature room at 25 ° C., and three days later, the number of live and dead insects in each leaf piece was counted to determine the miticidal rate. The evaluation of the drug effect is carried out in four stages (A: 100
%, B: 99-80%, C: 79-60%, D: 59%
Below). The results are shown in Table 12.

[0089]

[Table 12]

(2) Control efficacy test against wheat leaf rust (preventive effect) Ten wheat (cultivar: Kobushi-komugi) was grown in a plastic flower pot with a diameter of 6 cm per plant, and seedlings at 1.5 leaf stage were grown. A wettable powder of the compound (I) shown in Tables 4 to 11 prepared according to Example 2 was mixed with a surfactant (0.01
%) And dilute it to 500ppm with 2% per pot.
Sprayed with 0 ml. After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then the plants were uniformly spray-inoculated with a spore suspension of wheat leaf rust fungus. After inoculation, it was grown in a glass greenhouse for 1 week, and the degree of wheat leaf rust lesions appearing on the first leaf was investigated. Evaluation of the drug effect was performed in 6 levels (0: whole disease, 1: lesion area 60%, compared with the degree of lesions in the untreated area.
Degree 2: The lesion area is about 40%, 3: The lesion area is 20
%, 4: lesion area is 10% or less, 5: no lesion). The results are shown in Table 13.

[0091]

[Table 13]

(3) Control efficacy test against rice blast (preventive effect) Ten rice plants (cultivar; Nihonbare) were cultivated in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were grown. Each wettable powder of the compound (I) shown in Tables 4 to 11 prepared according to Example 2 was diluted to 500 ppm with water containing a surfactant (0.01%), and sprayed at 20 ml per pot. did. After spraying, it was cultivated in a glass greenhouse for 2 days, and then a conidiospore suspension of rice blast fungus prepared from diseased leaves was uniformly spray-inoculated onto plant leaves. 5 days after inoculation 28
The degree of rice blast lesions appearing on the leaves was investigated after growing in a humidity chamber at ℃. The results are shown in Table 14 by the 6-step evaluation method described in (2) above.

[0093]

[Table 14]

(4) Efficacy test against sweet potato root-knot nematodes A wettable powder of the compound (I) shown in Tables 4 to 11 prepared according to Example 2 was diluted to 200 ppm with water. Then, put 0.5 ml of the drug solution in a test tube, and
~ 0.5 liquid containing 40 sweet potato nematodes
ml was added. Two days after being left in a constant temperature room at 25 ° C, the number of live and dead insects was counted under a microscope to determine the mortality rate. The evaluation of the drug effect is divided into four stages (A: 10
0-90%, B: 89-80%, C: 79-60%,
D: 59% or less). The results are shown in Table 15.

[0095]

[Table 15]

[0096]

INDUSTRIAL APPLICABILITY The novel 1,2,3-triazole derivative of the present invention is a pesticide useful as a pest controlling agent.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shoji Shikida 5 1978, Kogushi, Ube, Ube City, Yamaguchi 5 Ube Kosan Co., Ltd. Ube Laboratory

Claims (5)

[Claims] 1. The following formula: (In the formula, R ¹ is a hydrogen atom, a halogen atom, or a carbon atom number 1
To an alkyl group having 6 to 6 or a phenyl group which may have a substituent; R ² may have an alkyl group having 1 to 15 carbon atoms or an alkyl group having 1 to 6 carbon atoms. _{^{benzyl, -CH 2 COOR 5, -CH 2}} CON (R
⁵ ) ₂ , a pyridyl group optionally having a halogen atom or a haloalkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, and 1 carbon atom An alkyl group having 1 to 4 carbon atoms which may have a haloalkyl group or a cyano group,
-CH ₂ CH ₂ OR ^5, or _-CH 2 _CH 2 _OCH 2 C
Represents H ₂ OR ⁵ (provided that R ⁵ represents an alkyl group having 1 to 4 carbon atoms); R ³ represents hydrogen atom, 1 carbon atom
~ 4 alkyl group or a phenyl group optionally having a halogen atom; R ⁴ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; or R ³ and R ⁴ are 1
Represents an alkylene group having 2 to 6 carbon atoms which may have 1 oxygen atom; n represents 0, 1, or 2. ) 1,2,3-triazole derivative represented by 2. The following formula: (Wherein R ¹ and R ² have the same meanings as described in claim 1) and a compound represented by the following formula: (In the formula, R ³ and R ⁴ have the same meanings as defined in claim 1;
X represents a leaving group. In the formula (I) according to claim 1, characterized in that the compound represented by the formula: (In the formula, R ¹ , R ² , R ³ and R ⁴ have the same meanings as defined in claim 1.) A process for producing a 1,2,3-triazole derivative represented by the formula. 3. The following formula: (Wherein, R ¹ and R ² have the same meanings as described in claim 1.) and a compound represented by the following formula: (Wherein R ³ has the same meaning as described in claim 1.) In the formula (I) according to claim 1, the compound represented by the following formula: (In formula, R < ¹ >, R < ² > and R < ³ > is synonymous with the description of Claim 1.) The manufacturing method of the 1,2,3-triazole derivative shown by these. 4. In the formula (I) according to claim 1, n is 0.
The 1,2,3-triazole derivative represented by the formula (1) is reacted with a peroxide, and the 1,2,3-triazole derivative represented by the formula (I) according to claim 1 wherein n is 1 or 2. Manufacturing method. 5. A compound represented by formula (I) according to claim 1,
A pest control agent containing a 2,3-triazole derivative as an active ingredient.