JPH09124640A - Pyridylimidazole compound, production thereof and fungicide for agricultural and horticultural use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new compound useful as a fungicide for agricultural and horticultural use. SOLUTION: The objective compound is expressed by the formula I (R<1> is H, a 1-10C alkyl, amino, cyano, a halogen, etc.; X is H, a halogen, a 1-6C alkyl, a 1-6C alkoxy, nitro, etc.; R<2> is H, hydroxy or a 1-4C alkoxy-1-4C alkoxy; Y is H, a 1-6C alkyl, a 1-6C haloalkyl or a halogen; (m) is 0-5; etc.) or its salt, e.g., 5-(3,5-dimethylphenyl)-4-(2-pyridyl)-2-trifluoromethylimidazole. The compound of the formula I can be produced by reacting a diketone of the formula II with an aldehyde expressed by R<1> 'CHO (R<1> ' is H or a 1-10C alkyl) or a hemiacetal expressed by the formula III (R<3> is a 1-6C alkyl) and ammonia or an ammonium salt. The compound is useful for the control of blights caused by phycomycetes, e.g. downy mildew of cucumber, downy mildew of grape and late blight of potato.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyridylimidazole compound, a process for producing the same, and an agricultural and horticultural fungicide.

[0002]

2. Description of the Related Art In the cultivation of agricultural and horticultural crops, a large number of control agents are used against crop diseases, but their use is insufficient due to insufficient control effect or the emergence of drug-resistant pathogens. Due to their limitations, their potential to cause phytotoxicity and contamination of plants, and their high toxicity to humans, fish and livestock, there are not many satisfactory control agents that are not always satisfactory. Therefore, there is a strong demand for the emergence of a drug that can be used safely with few such drawbacks. As a technique related to the present invention, DE. No. 2221546 describes that the following compounds are useful as anti-inflammatory agents and analgesic / antipyretic agents.

[0003]

Embedded image

USP. The following compounds are exemplified as anti-inflammatory agents in 4503065, but the physical properties are not described.

[0005]

Embedded image

Further, none of the above-mentioned documents describes that the compounds represented by Chemical formulas 7 and 8 are useful as fungicides for agricultural and horticultural use.

[0007]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel compound which can be used as an agricultural and horticultural fungicide which can be synthesized industrially advantageously, has a certain effect, and can be used safely.

[0008]

The present invention provides a compound of formula [I] having excellent agricultural and horticultural bactericidal activity.

[0009]

Embedded image

[Wherein R ¹ is a hydrogen atom, a linear or branched C _1-10 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl. {This alkyl group is
Halogen atom such as fluorine, chlorine, bromine, methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-
C such as butoxy, pentyloxy, hexyloxy
_1-6 alkoxy group may be substituted}, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and other C _3-7 cycloalkyl groups, halogen atoms such as fluorine, chlorine and bromine, cyano groups or amino groups Represent R ² represents a hydrogen atom, a hydroxyl group, or a C _1-4 alkoxy C _1-4 alkoxy group such as an ethoxymethoxy or 1-ethoxyethoxy group. X is a hydrogen atom, a halogen atom such as fluorine, chlorine or bromine, a linear or branched C _1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl or hexyl, methoxy, C _1-6 alkoxy groups such as ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy, hexyloxy, C _1-6 haloalkyl groups such as trifluoromethyl, trifluoroethyl, pentafluoroethyl, cyano groups, C _1-6 haloalkoxy group such as nitro group, trifluoromethoxy, difluoromethoxy, trichloromethoxy, trifluoroethoxy, difluoroethoxy, pentafluoroethoxy, methylthio, ethylthio, propylthio, isopropylthio, butylthio, t-butylthio, pentylthio, Hexylch C _1-6 alkylthio group such as O, methylsulfinyl, ethylsulfinyl, propyl sulfinyl, isopropyl sulfinyl, butylsulfinyl, t- butyl sulfinyl, pentylsulfamoyl sulfinyl, C _1-6 alkylsulfinyl group such as hexyl-sulfinyl, methylsulfonyl, ethylsulfonyl , Propylsulfonyl, isopropylsulfonyl, butylsulfonyl, t-
C _1-6 alkylsulfonyl group such as butylsulfonyl, pentylsulfonyl, hexylsulfonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl,
Represents a C _1-6 alkoxycarbonyl group such as t-butoxycarbonyl. Y is a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl,
A straight or branched C _1-6 alkyl group such as hexyl, a C _1-6 alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy group, trifluoromethyl, trichloromethyl, trifluoroethyl, pentafluoroethyl, etc. C _1-6 represents a halogen atom such as haloalkyl group, fluorine, chlorine and bromine. m represents an integer of 0 to 5, and when 2 or more, X may be different from each other. n represents an integer of 0 to 4, and when 2 or more, Y may be different from each other. ] It is a pyridyl imidazole compound or its salt represented by these, a manufacturing method, and an agricultural and horticultural germicide. Examples of the salt include metal salts such as copper and mineral acid salts such as hydrochloric acid.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by the following method.

[0012]

Embedded image

(In the formula, X, Y, R ¹ ′, R ³ , m and n have the same meanings as described above.) Aldehydes of α-diketones (II) and (III) or (IV)
The hemiacetals and the ammonia reagent are reacted in the absence of solvent or a suitable organic solvent at -50 to 150 ° C. Solvents that can be used include water, alcohols, carboxylic acids such as acetic acid, ethers such as THF, esters such as ethyl acetate, amides such as DMF, hydrocarbons such as benzene and toluene, DMSO, acetonitrile. , Nitromethane and the like. As the ammonia reagent, ammonia gas, ammonia water, ammonium acetate, ammonium carbonate, ammonium chloride or the like can be used. The amount used is 0.3 to 10 equivalents of compound (III) or (IV) with respect to 1 equivalent of compound [II] Ammonia reagent 1
The combination is preferably from 20 to 20 equivalents, particularly from 1 to 5 equivalents for (III) or (IV) and 2 to 10 equivalents for the ammonia reagent. The starting material diketone [II] can be synthesized according to the method shown below.

[0014]

Embedded image

(In the formula, X, Y, m and n have the same meanings as above.) Examples of the oxidizing agent used in the reaction include selenium dioxide, nickel oxide, NBS-water, bromine-water and hypochlorous acid. Examples thereof include sodium acidate, hydrogen peroxide solution, and peracetic acid.

Further, the compound represented by the formula (I ') is a 2- (α-halophenacyl) pyridine (V) as shown below.
It can also be produced by reacting an amidine (VI) in the presence of a base.

[0017]

Embedded image

(In the formula, X, Y, R ¹ ′, m and n have the same meanings as described above, and V represents a halogen atom.) In the formula (I), R ¹ is a halogen atom such as chlorine or bromine. In this case, it can be produced by halogenating a compound in which R ¹ is a hydrogen atom by a usual method.

[0019]

Embedded image

In the formula (I), when R ¹ is an amino group, it can be produced by the following method.

[0021]

Embedded image

(In the formula, Ar represents an aromatic group.)

In the formula (I), a compound in which R ¹ is a cyano group can be produced by the following method.

[0024]

Embedded image

(In the formula, X, Y, m and n have the same meanings as described above.)

Further, in the formula (I), a compound in which R ² is a hydroxyl group or a C _1-4 alkoxy C _1-4 alkoxy group can be produced by the following method.

[0027]

Embedded image

(Wherein X, Y, R ^{1 '} , R ³ , V, m, n
Has the same meaning as described above. The compound of formula (I) can be easily produced as a corresponding metal salt by reacting an inorganic metal salt such as cupric chloride in an organic solvent such as acetone or ethanol.
The structure of the compound of the present invention was determined by NMR, IR, MS and the like.

[0029]

The present invention will be described in more detail with reference to the following examples. Example 1 Preparation of 5- (3,5-dimethylphenyl) -4- (2-pyridyl) -2-trifluoromethylimidazole

[0030]

Embedded image

1- (3,5-dimethylphenyl) -2-
(2-pyridyl) ethane-1,2-dione 1.20 g
(5.02 mmol) and ammonium acetate 3.48 g
(45.2 mmol) was added to 50 ml of acetic acid, and 3.25 g (22.6 mmol) of trifluoroacetaldehyde ethyl hemiacetal was added dropwise with stirring. The reaction mixture was heated under reflux for 2 hours, poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.33 g of the desired compound. m. p
65-67 ° C. Yield 84%

Example 2 5- (3,5-dimethylphenyl) -2-ethyl-4-
Production of (2-pyridyl) imidazole

[0033]

Embedded image

1- (3,5-dimethylphenyl) -2-
(2-pyridyl) ethane-1,2-dione 1.20 g
(5.02 mmol) and ammonium acetate 3.48 g
(45.2 mmol) was added to 50 ml of acetic acid, and 1.31 g (22.6 mmol) of propionaldehyde was stirred.
Was dripped. The reaction mixture was heated under reflux for 3 hours, poured into ice water, neutralized with an aqueous caustic soda solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified by alumina column chromatography to obtain 0.42 g of the desired compound. m. p
64-69 ° C Yield 30%

Example 3 2-Cyano-5- (3,5-dimethylphenyl) -4-
Production of (2-pyridyl) imidazole

[0036]

Embedded image

5- (3,5-dimethylphenyl) -4-
A mixture of (2-pyridyl) -2-trifluoromethylimidazole (1.08 g), dioxane (10 ml) and 28% aqueous ammonia (5 ml) was sealed in a 50 ml autoclave and heated at 150 ° C for 3 hours. After cooling to room temperature, the reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by neutral alumina column chromatography to give an intermediate 2-carboxamide body 0.32 g.
I got [IR (KBr); 1680 cm ^-1 ] This amide was heated under reflux with 3 ml of phosphorus oxychloride for 30 minutes,
It was poured into ice water, and the precipitated crystals were washed with water and ether in that order and then air-dried to obtain 0.30 g of the desired product (yield 30%).
IR (KBr); 2250 cm ^-1 (CN), mp. 2
24-229 ° C

Example 4 5 (4)-(3,5-dimethylphenyl) -4 (5)-
Production of (2-pyridyl) -1-hydroxy-2-trifluoromethylimidazole

[0039]

Embedded image

1- (3,5-dimethylphenyl) -2-
(2-pyridyl) ethane-1,2-dione 0.90 g
(3.77 mmol) and hydroxyamine hydrochloride 0.
26 g (3.77 mmol) was added to 20 ml of acetic acid, and 0.31 g (3.77 mmol) of sodium acetate was added with stirring.
Was added and the mixture was stirred overnight. 1.30 g (16.95 mmol) of ammonium acetate and 2.44 g (1 of trifluoroacetaldehyde ethyl hemiacetal) were added to the reaction mixture.
6.95 mmol) was added and heated at 90 ° C. for 3 hours.
The reaction mixture was poured into ice water, neutralized with caustic soda water, and then extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.58 g of the desired product.
mp. 145-147 ° C

Reference Example Production of 1- (3,5-dimethylphenyl) -2- (2-pyridyl) ethane-1,2-dione

[0042]

Embedded image

1- (3,5-dimethylphenyl) -2-
(2-pyridyl) ethanone 8.10 g (36 mmol)
Was dissolved in 70 ml of acetic acid, and 8.39 g of selenium dioxide (7
5.6 mmol) was added and heated at 50 ° C. for 2 hours.
The reaction mixture was concentrated under reduced pressure, water and ethyl acetate were added to the residue, and the mixture was filtered through Celite. The ethyl acetate layer was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue obtained was purified by silica gel column chromatography to obtain 4.55 g of the desired product. (Yield 53%) ¹ H-NMR (δ ppm) 2.36 (6H, s),
7.28 (1H, s), 7.54 (1H, dd), 7.
56 (2H, s), 7.95 (1H, t), 8.22
(1H, d), 8.68 (1H, d) Table 1 shows the compounds of the present invention produced as described above.

[0044]

[Table 101]

[0045]

[Table 102]

Since the compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi, it can be used for controlling various diseases caused during cultivation of agricultural and horticultural crops including flowers, grass and grass. Can be done. For example, rice blast ( Pyricularia oryzae ), blight ( Rhizoctonia solani ), boiled seedling ( Gibberella fujikuroi), sesame leaf blight ( Cochliobolus miyabeanus ), barley smut ( Ustilago nuda ), wheat red scab ( Gibberella zeae ) Puccinia recondita) Memonbyo (Pseudocercosporella herpotrichoides) glume blotch (Leptosphaeria nodorum) powdery mildew (Erysiphe graminis f. sp. tritici ) pink snow mold disease (Micronectriella nivalis) potato late blight (Phytophthora infestans) peanut brown spot disease (Mycosphaerella arachidis ) sugar beet brown spot disease (Cercospora beticola) cucumber powdery mildew (Sphaerotheca fuliginea) rot (Sclerotinia sclerotiorum) gray mold (Botrytis cinerea) downy mildew (Pseudoperonospora cubensis) tomato leaf blight (Cladosporium fulvum) plague (Pytophthora infestans ) eggplant black blight (Corynespora melongenae) onion gray rot Disease (Botrytis allii) strawberry powdery mildew (Sohaerotheca humuli) apple powdery mildew (Podosphaera leucotricha) scab (Venturia inaequalis) blossom disease (Monilinia mali) persimmon anthracnose (Gloeosporium kaki) Peach Haihoshibyo (Monilinia fructicola) Grapes powdery mildew (Uncinula necator) and downy mildew (Plasmopara viticola) without gymnosporangium (gymnosporangium asiaticum) black spot disease (Alternaria kikuchiana) tea Wamadarabyo (Pestalotia theae) and anthracnose (Colletotrichum theae-sinensis) citrus scab ( Elisinoe fawcetti) blue mold disease (Pennisillium italicum) Western Shiba snow mold large Rot (Sclerotinia borealis) can be used for the control of such.

Further, in recent years, resistance to benzimidazole agents, dicarboximide agents and acylalanine agents has been developed in various pathogenic bacteria, resulting in lack of efficacy of these agents. Is desired. The compound of the present invention is a drug having an excellent bactericidal effect not only on sensitive strains but also on pathogens resistant to benzimidazole agents, dicarboximide agents and acylalanine agents.

Diseases more preferably applied include algal fungal diseases such as cucumber downy mildew, grape downy mildew, and potato epidemic.

The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contacts such as ship bottoms and fish nets.

Further, by mixing the compound of the present invention into a paint or a fiber, it is possible to prevent bacteria on walls, bathtubs, shoes and clothes,
It can also be used as a stick mold.

Further, among the compounds of the present invention, anti-inflammatory action,
Some have analgesic / pyretic activity, insecticidal, acaricidal and herbicidal activities.

[0052]

[Means for Solving the Problems]

(Bactericide) When the compound of the present invention thus obtained is actually applied, it can be used in a pure form without adding other components, and a form that can be taken by a general pesticide for the purpose of using it as a pesticide, That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like. When a solid agent is intended as an additive or carrier, a soybean grain, vegetable powder such as flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay or other mineral fine powder, benzoic acid Organic and inorganic compounds such as soda, urea, and sodium sulfate are used. When a liquid dosage form is intended, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water Is used as a solvent.
In order to obtain a uniform and stable form in these preparations, a surfactant may be added, if necessary. The wettable powder, emulsion, and flowable powder thus obtained are diluted with water to a predetermined concentration to form a suspension or emulsion, and powders and granules are used as they are by spraying on plants. .

Although the compound of the present invention exerts sufficient efficacy alone, it can be used in combination with one or more kinds of various fungicides, insecticides, acaricides or synergists.

Examples of the fungicides, insecticides, acaricides, nematicides and plant growth regulators which can be used by mixing with the compound of the present invention include the following.

Bactericide: Copper agent: basic copper chloride, basic copper sulfate, etc. Sulfur agent: thiuram, manneb, mancozeb, polycarbamate, propineb, ziram, zineb, etc. Polyhaloalkylthio agent: captan, dichlorfluanid, fol Organic chlorine agents such as pets: chlorothalonil, phthalides, etc. Organic phosphorus agents IBP, EDDP, tolclofos-methyl, pyrazophos,
Fosetyl, etc. Benzimidazole: thiophanate methyl, benomyl, carbendazim, thiabendazole, etc. Dicarboximide: iprodione, vinclozolin, procymidone, fluorimide, etc. Carboxamide: oxycarboxin, mepronil, flutolanil, teclophthalam, trichlamide, penciclone, etc. Acylalanine: Metalaxyl, oxadixyl, furaraxyl, etc. SBI agents: triadimefon, triadimenol, bittertanol, microbutanyl, hexaconazole, propiconazole, trifumizole, prochloraz, pefurazoate, phenalimol, pyrifenox, triphorine, flucylazole, etaconazole, diclobutrazole, diclobutrazol. Fluotrimazole, Flutriafen, Penconazole, Di Conazole, cyproconazole, imazalil, tridemorph, fenpropimorph, butiobate, etc. Antibiotic agents: polyoxin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, etc. Others: propamocarb hydrochloride, quintozene, hydroxyisoxazole, metasulfocarb , Anilazine,
Isoprothiolane, probenazole, quinomethionate, dithianon, dinocab, diclomedine, mepanipyrim, ferimzone, fluazinam, pyroquilon, tricyclazole, oxolinic acid, dithianon, iminoctadine acetate, simoxanil, pyrrole nitrine, metasulfocarb, dietofencarb, fenapacryl, vinapacryl, vinapacryl, vinapacryl, vinapacryl. , Dodine, dimethomorph, phenazine oxide, etc.

Insecticides and acaricides: Organic phosphorus and carbamate insecticides: fenthion, fenitrothion, diazinon, chlorpyrifos, ES
P, bamidothion, fentoate, dimethoate, formothion, marathon, trichlorfon, thiomethone,
Hosmet, dichlorvos, acephate, EPBP,
Methyl parathion, oxydimetone methyl, ethion,
Salithion, cyanophos, isoxathion, pyridafenthion, phosalone, methithione, sulprophos, chlorfenbinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, profenophos, pyraclofos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, Carbofuran, Carbosulfan, Benfuracarb, Fratiocarb, Propoxur, BPMC,
MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb, phenoxycarb and the like. Pyrethroid insecticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, protrin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, Cycloprothrin, trolametrin, silafluofen,
Brofenprocune, Akrinasuri, etc. Benzoylurea and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, cartap, thiocyclam, bensultap, benzoepin, Diafenthiuron, acetamiprid, niranpyram, imidacloprid, fipronil, nicotine sulfate, rotenone, methaaldehyde, machine oil, microbial pesticides such as BT and insect pathogenic viruses. Nematicides: fenamiphos, phosthiazate and the like. Acaricide: chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate,
Hexthiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, phenothiocarb, dienochlor and the like.

Plant growth regulator: Gibberellins (eg, gibberellin A ₃ , gibberellin A ₄ , gibberellin A ₇ ) IA
A, NAA.

[0058]

【Example】

[Bactericide] Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, and can be varied in a wide range. Parts in Formulation Examples are parts by weight.

Example 5 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalene sulfonate 3 parts The active ingredient 40 is obtained by uniformly mixing and finely pulverizing the above components.
% Wettable powder.

Example 6 Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts The above components are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

Example 7 Suspension Compound of the present invention 10 parts Sodium lignin sulfonate 4 parts Sodium dodecylbenzene sulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts The above components are mixed until the particle size becomes 1 micron or less. Wet milling gives a suspension with 10% active ingredient.

[0062]

【The invention's effect】

Test Example 1 Cucumber downy mildew control test Cucumber cultivated in unglazed pot (variety "Sagamihanshiro")
The seedlings were sprayed with the emulsion of the compound of the present invention at a concentration of 200 ppm of the active ingredient. After spraying, air dry naturally at room temperature to remove the cucumber downy mildew ( Pseudoperonospora cu)
a spore suspension of Bensis) was sprayed and inoculated and maintained 4 days in a thermostatic chamber of repeating light and dark and wet and dry every 12 hours (25 ° C.). The appearance state of lesions on leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed an excellent control effect of 80% or more. 1, 2, 3, 4, 6, 12, 1
6, 24, 25, 26

Test Example 2 Grape downy mildew control test Leaves of open-planted grapes (cultivar "Kaiji", third grader) were punched into a disk having a diameter of 30 mm to prepare an emulsion of the compound of the present invention and a chemical solution having a concentration of 200 ppm of active ingredient. Soaked. After immersion, air-dry at room temperature, grape downy mildew ( Plasmopar)
a viticola) a zoosporangia suspension is spray inoculation was held for 10 days in a constant temperature chamber under illumination (20 ° C.). The state of appearance of lesions on the leaves was subjected to a comparative examination without treatment, and the control effect was determined. As a result, the following compounds showed an excellent control effect of 80% or more. 1, 2, 3, 4, 6, 12, 16, 25, 26

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Reference number in the agency FI technical display location (C07D 401/04 213: 16 233: 64) (72) Inventor Yokota cause 345 Takada, Odawara, Kanagawa Odawara Research Institute, Nippon Soda Co., Ltd.

Claims (3)

[Claims] 1. The formula [I]: [In the formula, R ¹ is a hydrogen atom, a C _1-10 alkyl group (which may be substituted with a halogen atom or a C _1-6 alkoxy group), a C _3-7 cycloalkyl group, an amino group, a cyano group. Alternatively, it represents a halogen atom. R ² represents a hydrogen atom, a hydroxyl group or a C _1-4 alkoxy C _1-4 alkoxy group. X is a hydrogen atom, halogen atom, C _1-6 alkyl group, C _1-6 alkoxy group, C _1-6 haloalkyl group, cyano group, nitro group, C _1-6 haloalkoxy group, C _1-6 alkylthio group , C _1-6 alkylsulfinyl group, C _1-6
It represents an alkylsulfonyl group or a C _1-6 alkoxycarbonyl group. Y is a hydrogen atom, a C _1-6 alkyl group, C
_{It represents a 1-6} alkoxy group, a C _1-6 haloalkyl group or a halogen atom. m represents an integer of 0 to 5, and when 2 or more, X may be different from each other. n represents an integer of 0 to 4,
When 2 or more, Y may be different. (However, R ¹ =
Excludes compounds of ^t Bu. )] The pyridyl imidazole compound or its salt represented by these. 2. A formula [II]: [In the formula, X, Y, m and n have the same meanings as described above. And a diketone represented by the formula [III]: embedded image R ¹ ′ CHO (wherein R ¹ ′ is a hydrogen atom, (halogen atom or C
An aldehyde represented by a C _1-10 alkyl group, which may be substituted with a _1-6 alkoxy group, or a C _3-7 cycloalkyl group) or a compound represented by the formula (IV): (Wherein R ¹ ′ has the same meaning as described above and R ³ represents a C _1-6 alkyl group) and a hemiacetal represented by the formula [I ′ ] [Chemical 5] A process for producing a pyridylimidazole compound represented by the formula [wherein X, Y, R ¹ ′, m and n have the same meanings as described above]. 3. The formula [I]: Characterized in that it contains, as an active ingredient, a viridylimidazole compound represented by the formula [wherein X, Y, R ¹ , R ² , m and n have the same meanings as described above] or a salt thereof. A fungicide for agriculture and horticulture.