Tetrazolinone compound and application thereof

A tetrazolinone compound represented by formula (1): wherein X represents CR6 or a nitrogen atom, R1, R2, R3, R4, and R6 each independently represents a halogen atom, a C1-C4 alkyl group optionally having one or more halogen atoms, etc., and R5 represents a C1-C4 alkyl group optionally having one or more halogen atoms, a C3-C4 cycloalkyl group optionally having one or more halogen atoms, etc., has excellent control activity against pests.

TECHNICAL FIELD

The present invention relates to a tetrazolinone compound and application thereof.

BACKGROUND ART

Heretofore, various chemicals have been developed so as to control pests and provided in practice use, but in some cases, these chemicals may not exert enough activity.

Meanwhile, there have been known, as compounds for controlling pests, compounds having a tetrazolinone ring represented by the following formula (A):

The present invention provides compounds having excellent control activity against pests.

DISCLOSURE OF THE INVENTION

The present inventors have intensively studied so as to find compounds having excellent control activity against pests, and found that a tetrazolinone compound represented by the following formula (1) has excellent control activity against pests, thus leading to the present invention.

The present invention includes the followings [1] to [4].[1] A tetrazolinone compound represented by formula (1):

wherein X represents CR6or a nitrogen atom,R1, R2, R3, R4, and R6each independently represents a halogen atom, a hydrogen atom, a cyano group, a C1-C4 alkyl group optionally having one or more halogen atoms, or a C1-C4 alkoxy group optionally having one or more halogen atoms, andR5represents a halogen atom, a C1-C4 alkyl group optionally having one or more halogen atoms, a C3-C4 cycloalkyl group optionally having one or more halogen atoms, or a C1-C4 alkoxy group optionally having one or more halogen atoms.[2] The tetrazolinone compound according to [1], wherein X is CR6.[3] The tetrazolinone compound according to [1], wherein X is a nitrogen atom.[4] The tetrazolinone compound according to [3], wherein R3and R4are hydrogen atoms.[5] A pest control agent comprising the tetrazolinone compound according to any one of [1] to [4].[6] A method for control pests, which comprises applying an effective amount of the tetrazolinone compound according to any one of [1] to [4] to plants or soil.[7] Use of the tetrazolinone compound according to any one of [1] to [4] for controlling pests.

According to the present invention, pests can be controlled.

MODE FOR CARRYING OUT THE INVENTION

In the present invention, a tetrazolinone compound represented by formula (1) is referred to as the present compound, and a pest control agent containing the present compound is referred to as the present control agent.

Substituents as used herein will be mentioned below.

The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the C1-C4 alkyl group optionally having one or more halogen atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a fluoromethyl group, a chloromethyl group, a dichloromethyl group, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2,2,2-trifluoroethyl group, and a 1-trifluoromethyl-2,2,2-trifluoroethyl group.

Examples of the C3-C4 cycloalkyl group optionally having one or more halogen atoms include a cyclopropyl group, a cyclobutyl group, a 2,2-dichlorocyclopropyl group, and a 2,2-difluorocyclopropyl group.

Examples of the C1-C4 alkoxy group optionally having one or more halogen atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, a trifluoromethoxy group, a difluoromethoxy group, a 2-fluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3-chloro propyloxy group, and a 3-chlorobutyloxy group.

Examples of Aspect of the present compound include the following compounds.A tetrazolinone compound in which R5is a halogen atom in formula (1).A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R5is a C3-C4 cycloalkyl group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R5is a C1-C4 alkoxy group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R1is a hydrogen atom in formula (1).A tetrazolinone compound in which R1is a halogen atom in formula (1).A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R1is a C1-C4 alkoxy group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R2is a hydrogen atom in formula (1).A tetrazolinone compound in which R2is a halogen atom in formula (1).A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R2is a C1-C4 alkoxy group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R3is a hydrogen atom in formula (1).A tetrazolinone compound in which R3is a halogen atom in formula (1).A tetrazolinone compound in which R3is a C1-C4 alkyl group optionally having one or more halogen atoms in formula (1).A tetrazolinone compound in which R4is a hydrogen atom in formula (1).A tetrazolinone compound in which R4is a halogen atom in formula (1).A tetrazolinone compound in which R4is a C1-C4 alkyl group optionally having one or more halogen atoms in formula (1).
[Aspect 1]A tetrazolinone compound represented by formula (1a):

wherein symbols are the same as defined above.A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 1].A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 1].A tetrazolinone compound in which R1is a hydrogen atom or a halogen atom in [Aspect 1].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 1].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 1].A tetrazolinone compound in which R5is a halogen atom in [Aspect 1].A tetrazolinone compound in which R5is a methyl group in [Aspect 1].A tetrazolinone compound in which R5is an ethyl group in [Aspect 1].A tetrazolinone compound in which R5is a methoxy group in [Aspect 1].A tetrazolinone compound in which R5is a cyclopropyl group in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, R1and R2are each independently a hydrogen atom, a halogen atom, a cyano group, or a C1-C4 alkoxy group optionally having one or more halogen atoms, and R3and R4are each independently a hydrogen atom or a halogen atom in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, and R1, R2, R3, R4, and R6are each independently a hydrogen atom, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, and R1, R2, R3, R4, and R6are each independently a hydrogen atom, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, R1and R4are each independently a hydrogen atom or a C1-C4 alkoxy group optionally having one or more halogen atoms, R3and R6are hydrogen atoms, and R2is a halogen atom in [Aspect 1].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, R1, R3, R4, and R6are hydrogen atoms, and R2is a halogen atom in [Aspect 1].
[Aspect 2]A tetrazolinone compound represented by formula (1b):

wherein symbols are the same as defined above.A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 2].A tetrazolinone compound in which in R1is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 2].A tetrazolinone compound in which R1is a hydrogen atom or a halogen atom in [Aspect 2].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 2].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 2].A tetrazolinone compound in which in R5is a halogen atom in [Aspect 2].A tetrazolinone compound in which R5is a methyl group in [Aspect 2].A tetrazolinone compound in which R5is an ethyl group in [Aspect 2].A tetrazolinone compound in which R5is a methoxy group in [Aspect 2].A tetrazolinone compound in which R5is a cyclopropyl group in [Aspect 2].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, R1and R2are each independently a halogen atom, a cyano group, or a C1-C4 alkoxy group optionally having one or more halogen atoms, and R3and R4are each independently a halogen atom in [Aspect 2].
[Aspect 3]A tetrazolinone compound represented by formula (1c):

wherein symbols are the same as defined above.A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 3].A tetrazolinone compound in which R1is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 3].A tetrazolinone compound in which R1is a hydrogen atom or a halogen atom in [Aspect 3].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, or a hydrogen atom in [Aspect 3].A tetrazolinone compound in which R2is a C1-C4 alkyl group optionally having one or more halogen atoms, a halogen atom, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 3].A tetrazolinone compound in which R5is a halogen atom in [Aspect 3].A tetrazolinone compound in which R5is a methyl group in [Aspect 3].A tetrazolinone compound in which R5is an ethyl group in [Aspect 3].A tetrazolinone compound in which R5is a methoxy group in [Aspect3].A tetrazolinone compound in which R5is a cyclopropyl group in [Aspect 3].A tetrazolinone compound in which R5is a C1-C4 alkyl group optionally having one or more halogen atoms, and R1and R2are each independently a halogen atom, a cyano group, or a C1-C4 alkoxy group optionally having one or more halogen atoms in [Aspect 3].

Next, a process for producing the present compound will be described.

The present compound represented by formula (1) can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as the compound (A1)) with a compound represented by formula (A2) (hereinafter referred to as the compound (A2)) in the presence of a base:

wherein R1, R2, R3, R4, R5and X are the same as defined above, and Z11represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a p-toluenesulfonyloxy group.

The reaction is usually performed in a solvent.

Examples of the base to be used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide; alkali metal halides such as sodium fluoride, potassium fluoride, and cesium fluoride; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; and alkali metal alkoxides such as sodium tert-butoxide and potassium tert-butoxide.

The compound (A1) to be used in the reaction is produced in accordance with Reference Production Process A of WO 2013/162072 A.

In the reaction, the compound (A2) is usually used in the proportion within a range of 1 to 10 mols, and the base is usually used in the proportion within a range of 0.5 to 5 mols, based on 1 mol of the compound (A1).

The reaction temperature of the reaction is usually within a range of −20 to 150° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

In the reaction, if necessary, sodium iodide, tetrabutylammonium iodide, and the like may be added, and these compounds are usually used in the proportion within a range of 0.001 to 1.2 mols based on 1 mol of the compound (A1)

After completion of the reaction, the present compound represented by formula (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound can also be purified by chromatography, recrystallization, and the like.

The compound (A2) can be produced by reacting the compound (AA2) with a sulfurizing agent:

wherein symbols are the same as defined above.

The reaction is usually performed in a solvent.

Examples of the solvent to be used in the reaction include hydrocarbons such as toluene and xylene; ethers such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, and anisole; acid amides such as N,N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; nitriles such as acetonitrile; mixtures thereof, and mixtures of water and these solvents.

Examples of the sulfurizing agent to be used in the reaction include phosphorous pentasulfide, Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide), and the like.

In the reaction, the sulfurizing agent is usually used in the proportion within a range of 0.5 to 10 mols based on 1 mol of the compound (AA2).

The reaction temperature of the reaction is usually within a range of 20 to 250° C. The reaction time of the reaction is usually within a range of 0.1 to 50 hours.

After completion of the reaction, the compound (A2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (A2) can also be purified by chromatography, recrystallization, and the like.

Although a form used for the present compound may be the present compound as itself, the present compound is usually used after mixing with solid carriers, liquid carriers, surfactants, and the like, and optionally adding auxiliary agents for formulation, such as stickers, dispersers, and stabilizers to thereby formulate into wettable powders, water dispersible granules, flowables, granules, dry flowables, emulsifiable concentrates, aqueous solutions, oil solutions, smoking agents, aerosols, microcapsules, and the like. In these formulations, the present compound is usually contained within a range of 0.1 to 99%, and preferably 0.2 to 90% by weight.

The method for applying the present control agent is not particularly limited, as long as the applying form is a form by which the present control agent can be applied substantially, and includes, for example, an application to plants such as a foliage application; an application to area for cultivating plants such as a submerged treatment; and an application to seeds such as seed disinfection.

The present compound can also be used as a mixture with other fungicides, insecticides, acaricides, nematicides, and plant growth regulators, or simultaneously therewith.

The application dose of the present control agent varies depending on weather conditions, dosage forms, timing of application, methods of application, areas to be applied, target diseases, target plants, and the like, and the amount of the present compound in the present control agent is usually within a range of 1 to 500 g, and preferably 2 to 200 g, per 1,000 m2of the area to be applied. The emulsifiable concentrate, the wettable powder, or the suspension concentrate is usually applied by diluting with water. In this case, the concentration of the present compound after dilution is usually within a range of 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight. The dust formulation or the granular formulation is usually applied, as itself without dilution. In the application to seeds, the amount of the present compound in the present control agent is usually within a range of 0.001 to 100 g, and preferably 0.01 to 50 g, per 1 kg of the seeds.

Also, in another embodiment, for example, the present compound or the present control agent can be administered to the inside (inside of the body) or the outside (body surface) of the below-mentioned vertebrate to thereby exterminate systemically or unsystemically the living things or parasites which are parasitic on the vertebrate. Examples of a method of the internal administration include oral administration, anal administration, transplantation, or administration via injection subcutaneously, intramuscularly, or intravenously. Examples of a method of the external administration include transdermal administration. Also, the present compound can be ingested to a livestock animal so as to exterminate sanitary insects which occur in the excrement of the animal.

When the present compound or the present control agent is applied to the animals such as the livestock animal and pets on which pests are parasitic, the dose varies depending on the administration method etc., and it is desirable to administer the present compound so that a dose of the active ingredient (present compound) is generally within a range of 0.1 mg to 2,000 mg, and preferably 0.5 mg to 1,000 mg, per 1 kg of body weight of the animal.

The present compound or the present control agent can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, and orchards. The present compound can control diseases occurred in the agricultural lands for cultivating the following plants.

The above-mentioned plants include genetically modified crops.

The pests which can be controlled by the present compound include plant pathogens such as filamentous fungus, as well as harmful arthropods such as harmful insects and harmful mites, and nemathelminth such as nematodes, and specifically include the following examples, but are not limited thereto.

The present control agent containing at least one selected from the group consisting of the above-mentioned known fungicides, insecticide, acaricides, nematicides, and plant growth regulators may be directly applied to a plant body to be protected from pests, or may be applied to soil for fix planting of the plant body, and seeds.

At least one selected from the group consisting of the above-mentioned known fungicides, insecticide, acaricides, nematicides, and plant growth regulators may be applied to the plant body, simultaneously or separately, when using together with the present control agent. When applying separately, an application date may be different and a different dosage form may be used.

It is possible to combine an application of the present control agent to seeds of the plant with an application of at least one selected from the group consisting of the above-mentioned known fungicides, insecticide, acaricides, nematicides, and plant growth regulators to the plant, or soil for fix planting of the plant. It is also possible to combine an application of at least one selected from the group consisting of known fungicides, insecticide, acaricides, nematicides, and plant growth regulators to seeds of the plant with an application of the present control agent to the plant, or soil for fix planting of the plant. An application to the plant, or soil for fix planting of the plant may be performed before, on, or after fix planting.

This application method is preferably applied to cultivation of corn, wheat, and rice.

It is possible to combine an application of the present control agent to a plant body, or soil on which the plant body is cultivated or to be cultivated (for example, soil of paddy fields, crop fields, orchards, or non-cultivated lands) with an application of at least one selected from known herbicides to the soil. The pest control agent of the present invention and herbicides can be applied simultaneously or separately. When applying separately, the application maybe performed on the same or different day.

Examples of the herbicide, which can be used together with the present control agent, include glyphosate, salts of glyphosate, glufosinate, salts of glyphosate, 2,4-D, salts of 2,4-D, dicamba, salts of dicamba, and flumioxazin.

EXAMPLES

The present invention will be described in more detail below by way of Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to these Examples.

First, Production Examples will be described.

Production Example 1

A mixture of 3 g 1-(4-chlorophenyl)-1H-pyrazol-3-ol (produced in accordance with WO 2013/162072 A), 10.3 g of di-phosphorus pentasulfide, and 100 ml of xylene was stirred at 150° C. for 24 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was diluted with ethyl acetate and then filtered through silica gel. The filtrate was concentrated under reduced pressure to obtain 1.17 g of a crude product containing 1-(4-chlorophenyl)-1H-pyrazole-3-thiole. A mixture of 1.10 g of 1-(2-bromomethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (produced in accordance with WO 2013/162072A), 1.17 g of the crude product containing 1-(4-chlorophenyl)-1H-pyrazole-3-thiole, 2.09 g of potassium carbonate, and 10 ml of acetonitrile was stirred at 80° C. for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.50 g of 1-(2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]thiomethyl}-3-methy1phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 1).

In accordance with the process mentioned above, it is possible to obtain compounds HA1001-001 to HA1012-333. The above-mentioned compounds HA1001-001 to HA1012-333 (hereinafter referred to as the present compound A) are aromatic compounds shown below [wherein Q represents any one of the below-mentioned substituent numbers 1 to 333]. In the following [substituent number; Q], 3-Py represents pyridin-3-yl, Ph represents phenyl, F represents fluoro, Cl represents chloro, Br represents bromo, CN represents cyano, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, CF3 represents trifluoromethyl, OMe represents methoxy, OEt represents ethoxy, OPr represents propoxy, Oi-Pr represents isopropoxy, di represents di, and tri represents tri.

HA1006-006 represents a group in which Q is represented by the substituent number 006 in formula (HA1006), and specifically represents a compound represented by the following formula.

Formulation Examples will be shown below.

Formulation Example 1

Fifty parts (50 parts) of any one of the present compounds

A, 3 parts of calcium ligninsulfonate, 2 parts of laurylmagnesium sulfate, and 45 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain each formulation.

Formulation Example 2

Twenty parts (20 parts) of any one of the present compounds A and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture was finely ground by a wet grinding method. Then, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto and 10 parts of propylene glycol is further added, followed by stirring and mixing to obtain each formulation.

Formulation Example 3

Two parts (2 parts) of any one of the present compounds A, 88 parts of kaolin clay, and 10 parts of talc are thoroughly ground and mixed to obtain each formulation.

Formulation Example 4

Five parts (5 parts) of any one of the present compounds A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are thoroughly mixed to obtain each formulation.

Formulation Example 5

Two parts (2 parts) of any one of the present compounds A, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are thoroughly ground and mixed. After the addition of water, the mixture is thoroughly kneaded and further granulated and dried to obtain each formulation.

Formulation Example 6

Ten parts (10 parts) of any one of the present compounds A, 35 parts of white carbon containing 50 parts of a polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and finely ground by a wet grinding method to obtain each formulation.

Next, Test Examples will be shown.

Test Example 1

Each of plastic pots was filled with soil and barley (cultivar: MIKAMO GOLDEN) was sowed and grown in a greenhouse for 7 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (500 ppm) of the present compound 1 was sprayed over stems and leaves of the barley so that it sufficiently adhered to the surface of the leaves of the barley. After spraying, the plant was air-dried. After 2 days, an aqueous suspension containing spores of barley net blotch fungus (Pyrenophora teres) was sprayed to inoculate the spores. After completion of the inoculation, the plant was placed for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 7 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with of the present compound was 30% or less of that on an untreated plant.

Test Example 2

Each of plastic pots was filled with soil and kidney bean (cultivar: NAGAUZURA SAITOU) was sowed and grown in a greenhouse for 8 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (500 ppm) of the present compound 1 was sprayed over stems and leaves of the kidney bean so that it sufficiently adhered to the surface of the leaves of the kidney bean. After spraying, the plant was air-dried and a PDA medium containing hyphae of the kidney bean stem rot fungus (Sclerotinia sclerotiorum) was placed on the leaves of the kidney bean. After the inoculation, all kidney beans were placed under high humidity condition only at night. Four days after the inoculation, the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

Test Example 3

Each of plastic pots was filled with soil and wheat (cultivar: APOGEE) was sowed and grown in a greenhouse for 10 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (500 ppm) of the present compound 1 was sprayed over stems and leaves of the wheat so that it sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried. After 4 days, an aqueous suspension containing spores of wheat leaf blotch fungus (Septoria tritici) was sprayed over the wheat to inoculate the spores. After completion of the inoculation, the plant was placed at 18° C. under high humidity condition for 3 days and then placed under illumination for 14 to 18 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

Test Example 4

Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed and grown in a greenhouse for 12 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (500 ppm) of the present compound 1 was sprayed over stems and leaves of the cucumber so that it sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then inoculated by sprinkling with spores of cucumber powdery mildew fungus (Sphaerotheca fuliginea, a QoI-resistant strain in which, among the genes encoding cytochrome b, the amino acid residue at position 143 of cytochrome b is mutated from glycine to alanine). After the inoculation, the plant was cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 8 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

Test Example 5

Each of plastic pots was filled with soil and wheat (cultivar: SHIROGANE) was sowed and grown in a greenhouse for 9 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (200 ppm) of the present compound 1 was sprayed over stems and leaves of the wheat so that it sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried and cultivated at 20° C. for 5 days under illumination, and then inoculated by sprinkling with spores of wheat rust fungus (Puccinia recondita). After the inoculation, the plant was placed at 23° C. for one day under dark and high humidity condition, and cultivated under illumination at 20° C. for 8 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

Test Example 6

Each of plastic pots was filled with soil and barley (cultivar: MIKAMO GOLDEN) was sowed and grown in a greenhouse for 7 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (200 ppm) of the present compound 1 was sprayed over stems and leaves of the barley so that it sufficiently adhered to the surface of the leaves of the barley. After spraying, the plant was air-dried. After 2 days, an aqueous suspension containing spores of barley scald fungus (Rhynchosporium secalis) was sprayed to inoculate the spores. After completion of the inoculation, the plant was placed for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 7 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with of the present compound was 30% or less of that on an untreated plant.

Test Example 7

Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed and grown in a greenhouse for 19 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (50 ppm) of the present compound 1 was sprayed over stems and leaves of the cucumber so that it sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then, after 1 day, an aqueous suspension containing spores of cucumber anthracnose fungus (Colletotrichum lagenarium) was sprayed to inoculate the spores. After the inoculation, the plant was placed at 23° C. for one day under high humidity condition, and then cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 6 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

Test Example 8

Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed and grown in a greenhouse for 19 days. Then, each water dilution prepared by adjusting so as to contain a predetermined concentration (200 ppm) of the present compound 1 was sprayed over stems and leaves of the cucumber so that it sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then, after 1 day, an aqueous suspension containing zoospores of cucumber downy mildew fungus (Pseudoperonospora cubensis) was sprayed to inoculate the zoospores. After the inoculation, the plant was placed stand at 23° C. for one day under high humidity condition, and then cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 6 days, and then the area of lesion was investigated. As a result, the area of lesion on the plant treated with the present compound was 30% or less of that on an untreated plant.

The present compound has control activity against pests and is useful as an active ingredient of a pest control agent.