JPH0656801A - Alkenyltriazole derivative and pest control agent - Google Patents

Abstract

(57) [Summary] [Purpose] Excellent against various harmful insects, especially paddy rice pests such as planthoppers and leafhoppers, and horticultural pests such as Lepidoptera, aphids, and spider mites without adversely affecting crops. Provided is a pest control agent having a killing control effect. [Structure] General formula [Chemical formula 1] (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, X represents a halogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an alkoxy group, or the like, and n represents 0 or an integer of 1 to 5. Show, n
When is 2 or more, the same kind or different kinds of combination may be arbitrarily used. Y represents an alkenyl group having 3 or more carbon atoms which may be substituted with 1 to 4 halogen atoms. ) The triazole derivative represented by.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to an alkenyl-substituted triazole derivative and a pest control agent containing the same as an active ingredient.

[0002]

2. Description of the Related Art So far, 5- (O-chlorophenyl)
-3-Cyclohexyl-1-methyl-1H-1,2,4
-Triazole and the like are known to have activity against spider mite eggs, larvae, and aphid larvae (JP-A-56)
-154464 gazette specification).

[0003]

In recent years, the continuous use of insecticides for many years for controlling pests of agricultural and horticultural crops has caused a decrease in the sensitivity of the pests to the chemicals, making it difficult to control them with conventional pesticides. There is. This problem is particularly serious in pests of the order Hemiptera and Lepidoptera, including spider mites, and is a worrying situation. On the other hand, the insecticidal and acaricidal activities of the triazole derivatives specifically described in the above-mentioned publications cannot be said to be sufficient, and development of a pest control agent having a new action and a high control effect is desired.

[0004]

[Means for Solving the Problems] In order to cope with such a situation, the present inventors have synthesized various triazole derivatives and conducted repeated studies on their insecticidal activity. As a result, the triazole derivative has a halogen atom or the like at a specific position. Compounds that bind substituted phenyl groups and alkenyl groups that may be substituted with halogen atoms, etc. The present invention has been completed by finding out that it exhibits insecticidal activity against.

That is, the alkenyltriazole derivative of the present invention has the general formula [I]

[0006]

[Chemical 2]

(In the formula, R is an alkyl group having 1 to 4 carbon atoms,
X represents a halogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, an alkoxy group, a nitro group, a cyano group or a trifluoromethyl group, n represents 0 or an integer of 1 to 5, and n is 2 In the above case, the same kind or different kinds of combination may be arbitrarily used. Y represents an alkenyl group having 3 or more carbon atoms which may be substituted with 1 to 4 halogen atoms. ). The pest control agent of the present invention contains the above-mentioned triazole derivative as an active ingredient.

As a preferred compound in the present invention, R in the above general formula is a methyl group or an ethyl group,
When X is a halogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a methoxy group, a cyano group, a nitro group, a trifluoromethyl group, n is an integer of 1 to 5, and n is 2 or more. X may be any of the same or different combinations thereof, and examples thereof include compounds in which Y represents a 2-chloro-1-alkenyl group or a 2-bromo-1-alkenyl group having 3 or more carbon atoms.

The compound of the present invention can be prepared according to the following methods, but is not limited to these methods. Manufacturing method <A>

[0010]

[Chemical 3]

(In the formula, A represents a sulfur atom or an oxygen atom, B represents an alkyl group having 1 to 4 carbon atoms, R, X, n
And Y have the same meaning as described above. )

That is, the compound of the present invention represented by the general formula [I] is an N-acyl imido ester derivative or thioimidic acid ester derivative represented by the general formula [II] and a hydrazine derivative represented by the general formula [III]. Can be obtained by reacting in an inert solvent. As the solvent that can be used, any solvent that does not inhibit the reaction may be used, and examples thereof include ethers such as diethyl ether, tetrahydrofuran, dioxane and diglyme, aromatic hydrocarbons such as benzene, toluene and chlorobenzene, pentane, hexane and petroleum ether. Aliphatic hydrocarbons such as, dichloromethane, dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, nitriles such as acetonitrile, aprotic polar solvent such as dimethylformamide, dimethylacetamide, dimethylsulfoxide and water, and A mixed solvent obtained by combining solvents selected from these can also be used.

The amount of the reaction reagent used is usually represented by the general formula [I
The amount of the compound represented by the general formula [III] is 1.0 to 5.0 mol per 1 mol of the compound represented by I]. The reaction temperature is arbitrary between 0 ° C and the boiling point of the solvent, but preferably 0 ° C to 5 ° C.
The reaction is carried out in the range of 0 ° C. Although the reaction time varies depending on the compound, the purpose can usually be reached in 1 hour to 72 hours. Details of this reaction can be found, for example, in Synthesis (Synthesi
s), p. 483 (1983).

Further, the compound represented by the general formula [II], which is a raw material, can be produced according to the following method. Manufacturing method <B>

[0015]

[Chemical 4]

[Wherein W represents a halogen atom, A,
B, X, n and Y have the same meanings as described above. That is, the compound of general formula [II] can be produced by reacting the compound of general formula [IV] with the compound of general formula [V] in the presence of a base in an inert solvent. The compound of the general formula [IV] may be in the form of an acid addition salt, for example, a salt with boron tetrafluoride, hydrogen chloride, hydrogen bromide, hydrogen iodide and the like.

As the base, inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium hydroxide and potassium hydroxide, and organic bases such as diethylamine, triethylamine, pyridine and 4-N, N-dimethylaminopyridine. A class can be used. As the solvent that can be used, ketones such as acetone and methyl ethyl ketone, ethers such as diethyl ether, tetrahydrofuran, dioxane and diglyme, aromatic hydrocarbons such as benzene, toluene and chlorobenzene, pentane,
Hexane, aliphatic ethers such as petroleum ether, dichloromethane, dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, nitriles such as acetonitrile, dimethylformamide, dimethylacetamide,
An aprotic polar solvent such as dimethyl sulfoxide and water, and a mixed solvent obtained by combining a solvent selected from these can also be used.

The amount of the reaction reagent used is usually 0.1 mol of the compound of the general formula [V] per mol of the compound of the general formula [IV].
It is 8 to 1.3 mol. The amount of base used is of the general formula [I
V] is 1.0 to 2.0 times the equivalent amount to 1 mol of the compound. The reaction time varies depending on the compound, but is usually 1 hour to 2
The range is 4 hours. The reaction temperature is between 0 ° C. and the boiling point of the solvent. Details of this reaction can be found, for example, in The Journal of Organic Chemistry (J. Org. Che.
m.) 33, 1679 (1968) and the like.

[0019]

EXAMPLES The compounds of the present invention represented by the general formula [I] are shown in Tables 1 to 4. Regarding the geometrical isomerism of alkenes in the table, E is the entgegen body and Z is the tsumen body.
It is abbreviated as, and a single substance of E and Z and a mixture of E and Z are also included in the present invention. In addition, the compound numbers are referred to in the following description.

[0020]

[Table 1]

[0021]

[Table 2]

[0022]

[Table 3]

[0023]

[Table 4]

Next, the manufacturing method will be specifically described. Example 1 (E) -5- (2-chloro-1-methyl-1)
Synthesis of -propenyl) -3- (2-chlorophenyl) -1-methyl-1H-1,2,4-triazole (Compound 6) Ethyl 2-chlorobenzimidate (2.80 g), triethylamine (1.70 g) Was dissolved in toluene (50 ml) and (E) -3-chloro-
2-Methyl-2-butenoyl chloride was added dropwise, and after the addition, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, toluene (150 ml) was added to the reaction mixture, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Wakogel C-200: Wako Pure Chemical Industries, Ltd.) using a hexane-ethyl acetate mixed solution (10: 1) as a developing solvent, and an oily ethyl (E)- N- (3-chloro-1-methyl-2-butenoyl) -2-chlorobenzimidate (2.37 g) was obtained.

The obtained N-acylimidate was dissolved in toluene (50 ml), methylhydrazine (1.0 g) was added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (Wakogel C-200) using a hexane-ethyl acetate mixed solution (10: 1) as a developing solvent to obtain the desired product 1. 67 g of a pale yellow viscous liquid (refractive index: n ²⁰ =
1.5880).

NMR data (400 MHz, CDCl ₃ solvent, δ value, ppm) 2.09 (3H, q, J = 1.60Hz) 2.18 (3H, q, J = 1.60Hz) 3.84 (3H , s) 7.30 to 7.50 (3H, m) 7.85 to 7.91 (1H, m)

Example 2 (E) -5- (2-chloro-1)
-Methyl-1-propenyl) -3- (4-chloro-2-
Synthesis of fluorophenyl) -1-methyl-1H-1,2,4-triazole (Compound 27) Ethyl 4-chloro-2-fluorobenzimidate (3.0 g), triethylamine (1.5 g), (E) -3
-Chloro-2-methyl-2-butenoyl chloride (2.
3 g) was dissolved in toluene (100 ml), stirred at room temperature for 1 hour, and further heated under reflux for 4 hours. After completion of the reaction, water was added to the reaction mixture and the toluene layer was dried over anhydrous magnesium sulfate. Methylhydrazine (1.0 g) was added to this reaction solution.
Was added and stirred at room temperature for 48 hours. After the reaction was completed, it was washed with a dilute hydrochloric acid solution, further washed with water, dried over anhydrous magnesium sulfate and concentrated. This was purified by silica gel column chromatography using a hexane-ethyl acetate mixed solution (10: 1) as a developing solvent to obtain 1.75 g of the desired product as colorless needle crystals (melting point 75-77 ° C).

NMR data (60 MHz, CDCl ₃ solvent, δ value, ppm) 1.80 to 2.30 (6H, m) 3.81 (3H, s) 7.00 to 8.15 (3H, m)

Example 3 5- (1-Butyl-2-chloro-1-propenyl) -3- (2-chlorophenyl) -1
Synthesis of -Methyl-1H-1,2,4-triazole (Compound 57) Ethyl 2-chlorobenzimidate (2.02 g), potassium carbonate (1.52 g), (E, Z) -3-chloro-2
-Butyl-2-butenoyl chloride (2.55 g) was dissolved in acetone (50 ml), and the mixture was stirred with heating under reflux for 4 hours. After the reaction was completed, water (150 ml) was added to the reaction mixture,
It was extracted twice with ether (200 ml), washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrate was dissolved in dioxane (50 ml) and methylhydrazine (1.3
0 g) was added and the mixture was stirred at room temperature for 48 hours. After the reaction,
Toluene (250 ml) was added to the reaction mixture, which was washed with a dilute hydrochloric acid solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography using a hexane-ethyl acetate mixed solution (10: 1) as a developing solvent to obtain the target compound 1.3.
1 g was obtained as a pale yellow viscous liquid (refractive index: n ²⁰ = 1.5614).

NMR data (60 MHz, CDCl ₃ solvent, δ value, ppm) 0.88 (3H, t) 1.20 to 1.52 (4H, m) 2.04 (3H, s) 2.62 (2H , t) 3.84 (3H, s) 7.22 to 8.10 (4H, m)

Example 4 5- (2-chloro-1-octyl-1-propenyl) -3- (2-chlorophenyl)-
Synthesis of 1-methyl-1H-1,2,4-triazole (Compound 73) Ethyl 2-chlorobenzimidate (1.93 g),
(E, Z)-[EorZ] 3-chloro-2-octyl-
2-butenoyl chloride (2.52 g) was added to toluene (30
ml), and triethylamine (0.85 g) was added dropwise with stirring at 5 ° C to 10 ° C. After the addition, the mixture was stirred at room temperature for 4 hours. After the reaction was completed, toluene (150 ml) was added to the reaction mixture.
Was added, and the mixture was washed with a dilute hydrochloric acid solution and saturated saline and then dried over anhydrous magnesium sulfate. Methylhydrazine (1.0 g) was added to the obtained reaction solution, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was washed with a dilute hydrochloric acid solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
The concentrate was purified by silica gel column chromatography (Wakogel C-200) using a hexane-ethyl acetate mixed solution (15: 1) as a developing solvent to obtain the desired product 1.
12 g of a pale yellow viscous liquid (refractive index: n ²⁰ = 1.5446)
Got as.

NMR data (60 MHz, CDCl ₃ solvent, δ value, ppm) 0.85-1.70 (15H, m) 2.03 (3H, s) 2.64 (2H, t) 3.86 (3H , s) 7.13 to 8.03 (4H, m)

Example 5 Synthesis of 5- (2-chloro-1-dodecyl-1-propenyl) -3- (2,6-difluorophenyl) -1-methyl-1H-1,2,4-triazole (compound 78) Ethyl 2,6-difluorobenzimidate (1.50
g) and triethylamine (0.85 g) with toluene (30 m
l) and dissolved under stirring at a temperature between 5 ° C and 10 ° C (E, Z)-
3-Chloro-2-dodecyl-2-butenoyl chloride (2.50 g) was added dropwise, and after the addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, toluene (150 ml) was added to the reaction mixture, washed with a dilute hydrochloric acid solution and saturated saline, and dried over anhydrous magnesium sulfate. Methylhydrazine (0.8 g) was added to the obtained reaction solution, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was washed with a dilute hydrochloric acid solution and saturated saline,
The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Wakogel C-200) using a hexane-ethyl acetate mixed solution (15: 1) as a developing solvent, and 0.83 g of the desired product was pale yellow viscous liquid (refractive index: n ²⁰ = 1.5095).

NMR data (60 MHz, CDCl ₃ solvent, δ value, ppm) 0.85-1.70 (23H, m) 2.05 (3H, s) 2.63 (2H, t) 3.87 (3H , s) 7.10 to 7.90 (3H, m)

The agricultural and horticultural insect pest control agent of the present invention comprises a triazole derivative represented by the general formula [I] as an active ingredient. In order to use the compound of the present invention as a pest control agent, the compound of the present invention may be used as it is, but it is a powder formulation by incorporating a carrier, a surfactant, a dispersant or an auxiliary agent or the like generally used for formulation. It is also possible to use it by formulating it into a wettable powder, an emulsion, a fine granule or a granule.

As the carrier used for formulation, a solid carrier such as Sieglite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea, isopropyl alcohol, xylene, cyclohexanone, methylnaphthalene. Liquid carriers and the like. Surfactants and dispersants include alkylbenzene sulfonic acid metal salts, dinaphthylmethane disulfonic acid metal salts, alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers. , Polyoxyethylene sorbitan monoalkylate and the like.
Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like.

The mixing ratio of the active ingredient is appropriately selected according to need, but in the case of powder or granule, it is 0.05
~ 20% (weight), preferably 0.1% to 10% (weight) in range. When used as an emulsion or wettable powder, it is 0.5 to 80% (weight), preferably 1 to 60%.
It is preferable to appropriately select from the range of% (weight).

In use, it is diluted to an appropriate concentration and then sprayed or applied directly. The pest control agent of the present invention can be used by foliage application, soil application, nursery box application, water surface application, or the like. The application rate varies depending on the type of compound used, target pests, occurrence tendency, degree of damage, environmental conditions, dosage form used, etc., but when used as it is, such as powders and granules, per 10 are as an active ingredient 0.0
It may be appropriately selected from the range of 5 g to 5 kg, preferably 0.1 g to 1 kg. Further, when it is used in a liquid state such as an emulsion or a wettable powder, it is appropriately selected from the range of 0.1 to 5000 ppm, preferably 1 to 1,000 ppm.

The pest control agent of the present invention can be used by mixing with other insecticides, fungicides, fertilizers and plant growth regulators.

Next, the formulation method will be specifically described with reference to typical formulation examples. The types and compounding ratios of the compounds and additives are not limited to these and can be changed in a wide range. In the following description,% indicates weight percentage.

Formulation Example 1 Emulsion Emulsion was prepared by uniformly dissolving 30% of compound (2), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzene sulfonate and 35% of methylnaphthalene. It is diluted with water and applied.

Formulation Example 2 Wettable powder Compound (67) 40%, diatomaceous earth 15%, clay 15%,
White carbon 25%, dinaphthylmethane disulfonate sodium 2% and lignin sulfonate sodium 3
% Was uniformly mixed and pulverized to obtain a wettable powder. It is diluted with water and applied.

Formulation Example 3 Dust Powder 2% of compound (51), 5% of diatomaceous earth and 93% of clay were uniformly mixed and ground to give a powder. Apply this directly.

Formulation Example 4 Granules Compound (57) 5%, lauryl alcohol sulfate sodium salt 2%, sodium lignin sulfonate 5
%, Carboxymethylcellulose 2% and clay 86%
Are uniformly mixed and pulverized. 100 parts by weight of this mixture are mixed with 2 parts of water.
Add 0 parts by weight and knead.
It was processed into 32 mesh granules and then dried to obtain granules. Apply this directly.

[0045]

INDUSTRIAL APPLICABILITY The triazole derivative of the present invention is a planthopper such as a brown planthopper, a white-necked planthopper and a brown leafhopper, a leafhopper such as a green leafhopper and a green leafhopper, an aphid such as a cotton aphid, a peach aphid, a peach aphid, and a whitefly whitefly. , Insects such as scale insects such as stag beetles and stink bugs such as spider helicopter, insects of the order Lepidoptera such as diamondback moth, Pleurotus spp. It is effective for the control of Coleoptera pests such as, and Orthoptera pests such as American cockroaches and German cockroaches, as well as spider mites such as Nami mites, Kanzawa mites and citrus mites.

In particular, a compound group in which Y has a 2-chloro-1-alkenyl group having 3 to 8 carbon atoms in the general formula is effective against lepidopteran pests such as diamondback moth, and Y has 2 to 9 carbon atoms. A group of compounds having a -chloro-1-alkenyl group shows excellent effects on citrus red mite.

Next, the effect of the compound of the present invention will be described with reference to test examples. In the test, the compounds described in the following JP-A-56-154464 were used as comparative agents.

Comparative drug A 5- (o-chlorophenyl)
-3-Cyclohexyl-1-methyl-1H-1,2,4-
Triazole comparative drug B 5- (o-chlorophenyl) -3-ethyl-1-methyl-1H-1,2,4-triazole comparative drug C 3,5-bis (o-chlorophenyl) -1
-Methyl-1H-1,2,4-triazole Comparative drug D 5- (o-chlorophenyl) -1-methyl-3- (m-tolyl) -1H-1,2,4-triazole

Test Example 1 Testimony for killing brown planthopper A wettable powder prepared according to Formulation Example 2 was used with an active ingredient of 500 pp.
It was diluted with water to a concentration of m. Rice foliage was soaked in the drug solution, air-dried, and then allowed to stand in a test tube. Ten larvae of the brown planthopper were released therein and capped with absorbent cotton. Then, place it in a constant temperature room at 25 ° C, and check the number of dead insects 6 days later.
Mortality was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 5.
Shown in.

[0050]

[Table 5]

Test Example 2 Black leafhopper insecticidal test A wettable powder prepared according to Formulation Example 2 was used with an active ingredient of 500 pp.
Diluted with water to a concentration of m. Rice foliage was soaked in the drug solution, air-dried, and then allowed to stand in a test tube. Five larvae of the leafhopper leafhoppers were released therein and capped with absorbent cotton. Then 25
The sample was placed in a thermostatic chamber at ℃ for 5 days, the number of dead insects was investigated, and the dead rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 6.

[0052]

[Table 6]

Test Example 3 Cotton Aphid Insecticidal Test A wettable powder prepared according to Formulation Example 2 was used with an active ingredient of 100 pp.
Diluted with water to a concentration of m. Cucumber seedlings, which had been inoculated with cotton aphid nymphs in advance, were immersed in the drug solution and air-dried. The treated cucumber seedlings were placed in a constant temperature room at 25 ° C., and the number of dead insects was investigated 3 days later, and the dead insect rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 7.

[0054]

[Table 7]

Test Example 4 Nymphalid mites ovicidal test: Female adult mites of the genus Nematoda were released in advance on three kidney leaf discs (15 mm in diameter) to lay eggs for 24 hours, and then the female worms were removed. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the active ingredient had a concentration of 100 ppm, and sprayed on a leaf disk in a sufficient amount. 2 leaf disks after treatment
It was placed in a thermostatic chamber at 5 ° C., and after 7 days, the number of unhatched eggs was examined and the ovicidal rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 8.

[0056]

[Table 8]

Test Example 5 Citrus mites ovulation test Two citrus leaf pieces (diameter 10 m
After laying eggs in m) for 2 days to lay eggs, female adults were removed. A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 100 ppm, and citrus leaf pieces were immersed for 10 seconds. The treated citrus leaf pieces were placed in a thermostatic chamber at 25 ° C., and after 7 days, the number of unhatched eggs was examined and the ovicidal rate was calculated. The test was conducted in two consecutive cycles. The results are shown in Table 9.

[0058]

[Table 9]

Test Example 6 Diamondback moth insecticidal test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Cabbage leaves were dipped in the chemical solution, air-dried, and then placed in a vinyl chloride cup. Ten larvae of Plutella xylostella were released therein and the lid was covered. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was investigated and the dead insect rate was calculated.
The test was conducted in two consecutive cycles. The results are shown in Table 10.

[0060]

[Table 10]

[0061]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Reijiro Honami, Inventor Reijiro Honami 1 Shioshinta, Fukuda-cho, Iwata-gun, Shizuoka Prefecture, Keio Research Institute Co., Ltd. (72) (72) Takashi Yumeda Shiinta, Fukuda-cho, Iwata-gun, Shizuoka No. 408 No. 1 at KA Laboratories, Inc. (72) Inventor Yuyuki Yano 1809 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Naokazu Minokuchi 1809 Kamo, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Norihiko Izawa 5-17-1 Aobadai, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Tadami Hirano 2-9-3 Katsurugaoka, Kakegawa City, Shizuoka Prefecture

Claims (2)

[Claims] 1. A general formula: (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, X represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group, a nitro group, a cyano group or a trifluoromethyl group, and n is 0. Or an integer of 1 to 5, and when n is 2 or more, n may be the same or different combination, and Y is an alkenyl group having 3 or more carbon atoms which may be substituted with 1 to 4 halogen atoms. The triazole derivative represented by. 2. A pest control agent containing the alkenyltriazole derivative according to claim 1 as an active ingredient.