JP2011219419A - Optically active (+)-1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1h-1,2,4-triazole and noxious organism-controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a triazole compound exhibiting remarkably excellent noxious organism-controlling activity and to provide (+)-1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole.SOLUTION: The optically active (+)-1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole is represented by formula (I). The compound is obtained by optical resolution of a racemic mixture of 1-[2,4-dimethyl-5-(2,2,2- trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole.

Description

  The present invention relates to optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, The present invention relates to 4-triazole and a pest control agent containing it as an active ingredient.

The pest control agent used against pests is generally applied to pests, useful plants or useful crops, or the soil where the useful plants or useful crops are vegetated, etc. It is desired to be a drug that exhibits a sufficient control effect on a wide range of pests and can maintain the effect for a certain period of time. In particular, in recent years, development of a pest control agent that is safer and has a superior pest control activity at a low dose is desired due to environmental problems.
On the other hand, Patent Document 1 and Patent Document 2 include 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1, 2,4-Triazole is disclosed, which describes that the compound is useful as a pest control agent. However, although the compound has an asymmetric sulfur atom and the presence of an optical isomer is expected, these Patent Documents 1 and 2 have no description regarding the optical isomer.

WO99 / 55668 International Publication Specification WO2009 / 100822 International Publication Specification

  The present invention has been made in view of such circumstances, and has an optical activity (+)-1- [2,4-dimethyl-5- (2,2,2) having excellent pest control activity at a low dose. 2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole.

As a result of intensive studies, the present inventors have found that the compound described in Patent Document 1 is (+)-1- [2,4-dimethyl-5- (2), which is a specific optical isomer (enantiomer). , 2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole unexpectedly has another corresponding optical isomer (enantiomer) or The present inventors have found that the pest control activity is far superior to the corresponding racemate.
The present invention is based on such knowledge and has the following gist.

で表わされる光学活性（＋）−１−［２，４−ジメチル−５−（２，２，２−トリフルオロエチルスルフィニル）フェニル］−３−（トリフルオロメチル）−１Ｈ−１，２，４−トリアゾール。 (1) Formula (I):

Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4 -Triazole.

(2) (+)-1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H- described in (1) above A pest control agent comprising 1,2,4-triazole as an active ingredient.
(3) The pests include grasshopper pests, thrips pests, stink bugs, coleopteran insects, flies eye pests, butterfly pests, bee pests, terrestrial pests, spotted pests, cockroach pests, termites In the above (2), which are pests, pterodidae pests, whitefly pests, lice pests, plant parasitic mites, plant parasitic nematodes, plant parasitic molluscs, unpleasant animals, sanitary pests, or parasites The pest control agent described.
(4) The pest control agent according to (2), wherein the pest is a plant parasitic mite.
(5) Optical activity (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl)-described in (1) above A method for controlling pests using 1H-1,2,4-triazole.
(6) Optical activity (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4 -Triazole production method comprising 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4 -A production method characterized by optically resolving a racemate of triazole.

  Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, according to the present invention , 4-triazole is its optical isomer, optically active (−)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoro Methyl) -1H-1,2,4-triazole and racemic 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoro Compared with methyl) -1H-1,2,4-triazole, it exhibits a significantly superior pest control activity at a low dose, and is therefore useful as a pest control agent.

Hereinafter, the present invention will be described in detail.
In the present invention, “(+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, In the case of “, 4-triazole”, it is desirable that it is only the (+) isomer. However, depending on the method of optical resolution, the (−) isomer that is the optical isomer may not be completely separated, and in such a case, about 1 to 20% (−) isomer may be included.

  (+)-1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole of the present invention (Hereinafter also simply referred to as the compound of the present invention) is generally represented by the formula (II):

で表わされるラセミ体を光学分割することにより製造できる。その光学分割方法としては、例えば、光学異性体分離用高速液体クロマトグラフィー用カラムを利用することにより、（＋）光学異性体と（−）光学異件体とに分割することができる。光学異性体分離用高速液体クロマトグラフィー用カラムは一般に市販されており、例えば、ダイセル化学工業株式会社が製造・販売するキラルパックエーディー（ＣＨＩＲＡＬ ＰＡＫ ＡＤ）を使用することができる。

Can be produced by optical resolution. As the optical resolution method, for example, by using a high performance liquid chromatography column for optical isomer separation, it can be divided into (+) optical isomer and (−) optical isomer. The column for high-performance liquid chromatography for optical isomer separation is generally commercially available, and for example, CHIRAL PAK AD manufactured and sold by Daicel Chemical Industries, Ltd. can be used.

  Examples of the solvent used in the optical resolution include aliphatic hydrocarbons such as hexane and heptane; alcohols such as methanol, ethanol, propanol, 2-propanol and butanol; halogenated hydrocarbons such as dichloromethane and chloroform. Examples thereof include ethers such as diethyl ether, 1,2-dimethoxyethane, diisopropyl ether, tetrahydrofuran or dioxane; nitriles such as acetonitrile; acetic acid, water, or a mixed solvent thereof.

  The temperature and time in the optical resolution can vary widely. In general, the temperature is -20 to 60 ° C, preferably 5 to 50 ° C. The time is 0.01 hours to 50 hours, and preferably 0.1 hours to 2 hours.

When the compound of the present invention is used as an active ingredient of a pest control agent, the compound of the present invention may be used as it is, but a carrier, surfactant, or other auxiliary agent generally used for formulation as an agricultural chemical adjuvant. Formulated in various forms such as emulsion, powder, granule, tablet, wettable powder, water solvent, liquid, flowable powder, wettable powder, aerosol, paste, oil, smoke To do.
In these cases, the compounding ratio of the compound of the present invention is usually 0.1 to 90% by mass, preferably 1 to 70% by mass, based on the total amount (100% by mass) of the pest control agent, Agrochemical adjuvant is 10-99.9 mass%, Preferably it is 20-90 mass%.

  Carriers used for formulation can be divided into solid carriers and liquid carriers. Examples of solid carriers include animal and vegetable powders such as starch, activated carbon, soybean flour, wheat flour, wood flour, fish flour and milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, ammonium sulfate, urea. Inorganic powders such as Examples of the liquid carrier include water; alcohols such as isopropyl alcohol and ethylene glycol; ketones such as cyclohexanone, methyl ethyl ketone and isophorone; ethers such as dioxane and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and light oil; xylene and trimethyl. Aromatic hydrocarbons such as benzene, tetramethylbenzene, methylnaphthalene and solvent naphtha; Halogenated hydrocarbons such as chlorobenzene; Acid amides such as dimethylacetamide; Esters such as glycerin esters of fatty acids; Nitriles such as acetonitrile A sulfur-containing compound such as dimethyl sulfoxide;

  Examples of the surfactant include alkylbenzene sulfonic acid metal salt, dinaphthylmethane disulfonic acid metal salt, alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, Examples thereof include polyoxyethylene sorbitan monoalkylate, salt of naphthalene sulfonic acid formalin condensate and the like.

  Other adjuvants include, for example, sticking agents or thickeners such as carboxymethylcellulose, gum arabic, sodium alginate, guar gum, tragacanth gum and polyvinyl alcohol; antifoaming agents such as metal soaps; fatty acids, alkyl phosphates, silicones, paraffins Physical property improvers such as colorants and the like can be used.

  In actual use of these preparations, they can be used as they are or diluted to a predetermined concentration with a diluent such as water.

  Application of various preparations containing the compound of the present invention, or dilutions thereof, is generally carried out by a commonly used application method, ie, spraying (for example, spraying, misting, atomizing, dusting, dusting, water surface application, box Application), soil application (eg, mixing, irrigation, etc.), surface application (eg, application, powder coating, coating, etc.), immersion, poison bait, smoke application, etc.

  It is also possible to feed the livestock with the active ingredient in a feed to control the occurrence and growth of harmful insects, particularly harmful insects, in the excreta.

  It can also be applied by the so-called ultra-high concentration and small quantity spraying method. The mixing ratio of the active ingredient in the pest control agent in the ultra-high concentration small amount spraying method is appropriately selected as necessary, but in the case of powder or granule, 0.1 to 20% by mass, preferably 0.5 to In addition, in the case of using an emulsion and a wettable powder, it is 1 to 80% by mass, preferably 10 to 50% by mass.

  When the pest control agent of the present invention is used after being diluted with a diluent, it is generally used at an active ingredient concentration of 0.1 to 5000 ppm. When the preparation is used as it is, the application amount per unit area is 0.1 to 5000 g per ha, preferably 5 to 2000 g as an active ingredient compound, but is not limited thereto.

  In addition, it goes without saying that the compound of the present invention is sufficiently effective alone, but if necessary, other agricultural chemicals and fertilizers such as insecticides, acaricides, nematicides, fungicides, antivirals It can be mixed and used in combination with agents, attractants, herbicides, plant growth regulators, etc., and in this case, a more excellent effect may be exhibited.

The compound of the present invention is a grasshopper pest, a thrips pest, a stink bug, a coleopteran insect, a fly eye pest, a butterfly pest, a bee eye pest, a stag beetle pest, a spotted pest, a cockroach pest, a termite pest, For pests such as eye pests, whitefly pests, lice pests, plant parasitic mites, plant parasitic nematodes, plant parasitic molluscs, other harmful animals, unpleasant animals, sanitary pests, parasites, etc. It exhibits an excellent control effect, and particularly has an excellent activity against plant parasitic mites.
Examples of plant parasitic mites include, for example, Penthaleus major, Mite mite (Phytonemus pallidus), Mite mite (Polyphagotarsonemus latus), and a kind of lice mite (Siteroptes sp.) , Red spider mites (Brevipalpus lewisi), nymphalid spider mites (Tuckerella pavoniformis), etc. Tetranychus kanzawai, etc., Trisetacus pini, etc. Etc. Two family Ilex crenata eriophyid mites (Diptacus crenatae), Mugikonadani of mites family (Aleuroglyphus ovatus), Tyrophagus (Tyrophagus putrescentiae), the bulb mite, Rhizoglyphus (Rhizoglyphus robini), etc. can be exemplified.

  The compound of the present invention also exhibits a controlling effect on the pests exemplified above, which have acquired resistance to existing pest controlling agents.

  The compound of the present invention can be used for plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance by genetic recombination, artificial mating, etc., and further, organophosphorus compounds, carbamate compounds, synthetic pyrethroids It is also effective against pests that are resistant to existing insecticides and acaricides, such as compounds and acylurea compounds.

  Next, the production method, formulation method and use of the compound of the present invention will be specifically described by way of examples, but are not construed as being limited thereto.

Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, which is a compound of the present invention , 4-triazole can be produced by the method shown in the following examples.
(+)-1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole (Compound No. Preparation of I) Racemic 1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole ( Compound No. II) 0.3 g was dissolved in acetone (10 mL). The solvent was evaporated under reduced pressure, and a mixed solvent (1000 mL) of n-hexane / 2-propanol = 90/10 was added immediately before crystals were precipitated.

  Chiral Pak AD (CHIRAL PAK AD; manufactured and sold by Daicel Chemical Industries, Ltd.) (inner diameter 2 cm × length 25 cm) is used for the column, and a mixed solvent of n-hexane / 2-propanol = 90/10 is used as the mobile phase. The sample was subjected to high performance liquid chromatography at a flow rate of 7.0 mL / min at room temperature and analyzed with an ultraviolet absorption detector (270 nm). The peak at 30 minutes (peak 1) and the peak at 35 minutes were observed. (Peak 2) was obtained.

Each peak component was repeatedly collected, and the collected solution was vacuum concentrated at 60 ° C. to obtain 0.101 g and 0.100 g of crystals corresponding to peak 1 and peak 2, respectively. When each optical rotation was measured, the component of peak 1 was [α] _D ²⁵ = + 94.0 ° (C = 0.20 / methanol), and the component of peak 2 was [α] _D ²⁵ = −95.6 ° ( The specific light intensity of C = 0.20 / methanol was shown.

The peak 1 is the target (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1, 2,4-triazole (Compound No. I),
The peak 2 is (-)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, 4-triazole (Compound No. III).

¹ H-NMR data of Compound No. I (CDCl ₃ / TMS δ (ppm) value):
2.32 (3H, s), 2.45 (3H, s), 3.43-3.51 (2H, m), 7.33 (1H, s), 7.96 (1H, s), 8 .39 (1H, s)

¹ H-NMR data (CDCl ₃ / TMS δ (ppm) value) of Compound No. III:
2.32 (3H, s), 2.45 (3H, s), 3.43-3.51 (2H, m), 7.33 (1H, s), 7.96 (1H, s), 8 .39 (1H, s)

(Method for producing racemate)
<Reference Example 1>
Preparation of 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole:
(1) Production of 5-acetylthio-2,4-dimethylacetanilide To 168 g of chlorosulfonic acid, 78.4 g of 2,4-dimethylacetanilide was added at 50 ° C. or lower and further stirred at 70 ° C. for 1 hour. The reaction mixture was poured into a mixture of ice water and ethyl acetate, the organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 72 g of a solid residue. The obtained solid residue was dissolved in 550 ml of acetic acid, 25.6 g of red phosphorus and 4.0 g of iodine were added, and the mixture was heated to reflux for 4 hours. After cooling at room temperature, the insoluble material was filtered off, acetic acid was concentrated under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 47.5 g of 5-acetylthio-2,4-dimethylacetanilide.

(2) Production of 2,4-dimethyl-5-mercaptoaniline 700 ml of 10% potassium hydroxide aqueous solution was heated to 70 ° C., 47.5 g of 5-acetylthio-2,4-dimethylacetanilide was added, and the mixture was further heated under reflux for 10 hours. did. The resulting reaction mixture was cooled, concentrated hydrochloric acid and citric acid were added to pH 5, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 30 g of 2,4-dimethyl-5-mercaptoaniline.

(3) Production of 2,4-dimethyl-5- (2,2,2-trifluoroethylthio) aniline 2,4-dimethyl-5-mercaptoaniline 20 g, potassium carbonate 24 g, Rongalit (formaldehyde sodium sulfoxylate) After adding 41 g of 2,2,2-trifluoroethyl iodide dropwise to a mixture of 4.0 g and N, N-dimethylformamide 150 ml, the mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to remove 2,4-dimethyl-5- (2,2,2 -Trifluoroethylthio) aniline 29 g was obtained.

¹ H-NMR data (CDCl ₃ / TMS δ (ppm) value): 2.13 (3H, s), 2.34 (3H, s), 3.32 (2H, q), 3.52 (2H, s), 6.84 (1H, s), 6.91 (1H, s)

(4) Production of trifluoroacetaldehyde [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] hydrazone In 96 g of 40% sulfuric acid, 8.8 g of sodium nitrite at 30 ° C. or less. Little by little, then 46 ml of acetic acid was added dropwise at 30 ° C. or lower. To this mixture, a solution of 27.4 g of 2,4-dimethyl-5- (2,2,2-trifluoroethylthio) aniline in 50 ml of acetic acid was added dropwise at 5 ° C. or lower over 30 minutes, and further at 0 ° C. for 2 hours. Stir. This reaction solution was poured into a solution of 44 g of tin chloride in 200 ml of 6N hydrochloric acid at −30 to 0 ° C., and further stirred at 10 ° C. for 30 minutes. To this reaction solution, 22.6 g of trifluoroacetaldehyde methyl hemiacetal, 300 ml of water, and 100 ml of diisopropyl ether were added and stirred at 50 ° C. for 1 hour. The reaction mixture was extracted with diisopropyl ether, the organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography to obtain 32.7 g of trifluoroacetaldehyde [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] hydrazone.

(5) Production of N- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] trifluoroacetohydrazonoyl bromide Trifluoroacetaldehyde [2,4-dimethyl-5- ( 2,2,2-trifluoroethylthio) phenyl] hydrazone (5.5 g) was dissolved in 50 ml of N, N-dimethylformamide, 3.0 g of N-bromosuccinimide was added at 0 ° C., and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with diisopropyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.5 g of N- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] trifluoroacetohydrazonoyl bromide.

(6) 1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazol-5-amine N- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] trifluoroacetohydrazonoyl bromide 4.1 g, S-methylisothiourea hydrogen iodide salt 3.3 g, To a mixture of 20 ml of tetrahydrofuran, 3.1 g of triethylamine was added dropwise, and the mixture was further stirred at 60 ° C. for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography to obtain 1- [2,4-dimethyl-5- (2,2,2-trimethyl) as pale yellow crystals (melting point: 176-178 ° C.). 3.2 g of fluoroethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine was obtained.

(7) Production of 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole 1.0 g of [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazol-5-amine was added to tetrahydrofuran. It melt | dissolved in 20 ml, 1.6 g of t-butyl nitrites were dripped under heating-refluxing, and also it heated and refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by column chromatography. 1- [2,4-dimethyl-5- (2,2,2-trifluoro) of pale yellow crystals (melting point: 85-86 ° C.) 0.82 g of ethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole was obtained.

(8) Production of 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole 1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole 0.52 g was dissolved in 10 ml of chloroform. At 0 ° C., 0.34 g of m-chloroperbenzoic acid (purity 75%) was added, and the mixture was further stirred at 0 ° C. for 1 hour. The organic layer was washed with an aqueous sodium thiosulfate solution, then with an aqueous sodium hydrogen carbonate solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoro) of pale yellow crystals (melting point: 149 to 150 ° C.). 0.48 g of methyl) -1H-1,2,4-triazole was obtained.
¹ H-NMR data (CDCl ₃ / TMS δ (ppm) value): 2.32 (3H, s), 2.45 (3H, s), 3.39-3.55 (2H, m), 7. 33 (1H, s), 7.96 (1H, s), 8.39 (1H, s)

  Next, the preparation method will be specifically described with reference to typical preparation 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, “parts” means parts by mass.

[Formulation Example 1] Emulsion Compound No. I 30 parts Cyclohexanone 20 parts Polyoxyethylene alkyl aryl ether 11 parts Calcium alkylbenzenesulfonate 4 parts Methylnaphthalene 35 parts

[Formulation Example 2] Wetting agent Compound of Compound No. I 10 parts Naphthalenesulfonic acid formalin condensate sodium salt 0.5 parts Polyoxyethylene alkylaryl ether 0.5 parts Diatomaceous earth 24 parts Clay 65 parts Evenly mixed This was pulverized into a wettable powder.

[Formulation Example 3] Powder Compound of Compound No. I Compound 2 parts Diatomaceous earth 5 parts Clay 93 parts The above was mixed and ground uniformly to obtain a powder.

[Formulation Example 4] Granule Compound of Compound No. I 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethylcellulose 2 parts Clay 86 parts The above was uniformly mixed and ground. The mixture was kneaded with an equivalent amount of 20 parts of water, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to give granules.

  Next, the effect of the pest control agent comprising the compound of the present invention as an active ingredient will be described with test examples.

[Test Example 1] Insecticidal activity against leaf mite (susceptible strain) (leaf disc spraying test)
About half of the water was put into a plastic cup with a capacity of 60 mL, a perforated lid was placed, absorbent cotton was put into the hole and water was soaked, and two filter papers were placed on top of it. On top of that, two leaves of Phaseolus vulgaris cut into a circle with a diameter of 2 cm are placed, and 10 female adults of the susceptible strain of the spider mite (Tetranychus urticae) are inoculated one by one and kept at 25 ° C. (photoperiod condition: light period) (16 hours / dark period 8 hours). After removing the abnormal insects and dead insects, the test compound formulated according to Formulation Example 2 was sprayed with a drug whose dilution was adjusted as shown in Table 1 (2 mg / cm ² ). Two days after the treatment, the number of dead insects was counted, and the rate of killing insects was calculated using Equation 1. The test was conducted in a two-track system.

Formula 1

[Table 1]
―――――――――――――――――――――――――――――――――――――――
Test compound Concentration (ppm) Insecticide rate (%)
―――――――――――――――――――――――――――――――――――――――
Compound No. I (+)-enantiomer 0.39 100
Compound No. II Racemate 0.39 6.3
Compound No. III (-)-enantiomer 50 0
―――――――――――――――――――――――――――――――――――――――

[Test Example 2] Osmotic transfer activity against soil spider mite (complex resistant strain) (soil irrigation cup test)
A plastic cup planted soybean (Glycine max) was inoculated with 35 female adults of the compound resistant strain Nite spider mite (Tetranychus urticae) and placed in a constant-temperature greenhouse photoperiod condition at 25 ° C. (light period 16 hours / dark period 8 hours) overnight. It was. The test compound formulated according to Formulation Example 2 was diluted with a reagent adjusted to the prescribed concentration shown in Table 2 (5 mL / strain), and after 13 days, the number of surviving insects was counted. The value was calculated. The test was conducted in a two-track system.

Formula 2

[Table 2]
―――――――――――――――――――――――――――――――――――――――
Test compound concentration (ppm) Control value ―――――――――――――――――――――――――――――――――――――――
Compound No. I (+)-enantiomer 50 100
Compound No. II Racemate 50 0
Compound No. III (-)-enantiomer 50 0
―――――――――――――――――――――――――――――――――――――――

[Test Example 3] Penetration activity against urticae (composite resistant strain) (soybean: cup test)
The test compound formulated according to Formulation Example 2 is diluted to the prescribed concentration shown in Table 3, and this diluted solution is applied to the leaf surface of soybean (Glycine max) seedlings that are planted in plastic cups. Ten female adults of the resistant strain Nite spider mite (Tetranychus urticae) were inoculated. Six days after the treatment, the number of dead insects was counted, and the rate of killing insects was calculated according to Formula 1. The test was conducted in a constant temperature room at 25 ° C. The test was conducted in a two-track system.

[Table 3]
―――――――――――――――――――――――――――――――――――――――
Test compound Concentration (ppm) Insecticide rate (%)
―――――――――――――――――――――――――――――――――――――――
Compound No. I (+)-enantiomer 50 100
Compound No. II Racemate 50 25
Compound No. III (-)-enantiomer 100 20
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[Test Example 4] Penetration activity against citrus spider mite (composite resistant system) (citrus: greenhouse pot test)
Test compounds formulated according to Formulation Example 2 are diluted to the prescribed concentrations listed in Table 4, and this diluted solution is applied to the leaf surface of citrus (Citrus unshiu) planted in an unglazed pot, and the compound resistant strain is applied to the back of the leaf. Ten female nymphs (Panonychus citri) were inoculated and placed in a greenhouse. Six days after the treatment, the number of dead insects was counted, and the rate of killing insects was calculated according to Formula 1. The test was conducted in a two-track system.

[Table 4]
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Test compound Concentration (ppm) Insecticide rate (%)
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Compound No. I (+)-enantiomer 3.13 100
Compound No. II Racemate 3.13 0
Compound No. III (-)-enantiomer 50 11.1
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  Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, according to the present invention 4-Triazole is useful as a pest control agent because it exhibits a significantly excellent pest control activity at a low dose.

Claims (6)

Formula (I):

Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2, 4-triazole.   The optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1, according to claim 1. A pest control agent comprising 2,4-triazole as an active ingredient.   Pests include butterfly insects, thrips insect insects, stink bug insects, coleopteran insects, fly eye insects, butterfly insect insects, bee insect insects, terrestrial insect insects, insect eye insects, cockroach insect insects, termite insect insects The pest control according to claim 2, which is a pest, a whitefly pest, a lice pest, a plant parasitic mite, a plant parasitic nematode, a plant parasitic mollusc, an unpleasant animal, a sanitary pest, or a parasite Agent.   The pest control agent according to claim 2, wherein the pest is a plant parasitic mite.   The optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1, according to claim 1. Pest control method using 2,4-triazole.   Optically active (+)-1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole A process for the preparation of 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -3- (trifluoromethyl) -1H-1,2,4-triazole A production method comprising optically resolving a racemate.