JPH09309885A - Pyridylpyrrole compound, its production and germicide for agriculture and horticulture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a pyridylpyrrole compound useful for prevention of every kind of plant disease as a germicide for an agriculture and a horticulture. SOLUTION: This pyridylpyrrole compound is represented by formula I [R<1> is cyano, carbamoyl, formyl, hydroxyiminomethyl, etc.; R<2> is H, an alkylcarbonyloxymethyl, benzoyloxymethyl, alkoxycarbonyl, etc.; X is H, a halogen, an alkyl, an alkoxy, etc.; Y is H, a halogen, an alkyl, an alkoxy, etc.; Z is H, a halogen or an alkyl; (m) is 0 to 5; (n) is 0 to 4], e.g. 2-(3- chlorophenyl)-3-(2-pyridyl)-5-formylpyrrole. The compound of formula I is obtained by reacting phenylglycines of formula II with an acid anhydride of the formula (R<1> 'CO)2 O [R<1> ' is H, a 2-4C alkenyl (substituted by a halogen) or a 2-4C alkynyl] and ethynylpyridines of formula III (Z' is H or a 1-6C alkyl) in the presence of a tri-valent phosphorous compound and a dehydrating agent. The pyridylpyrrole compound is effective for preventing downy mildews of a cucumber and a grape and an epidemic of a potato.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a novel pyridylpyrrole compound, a process for producing the same, and a fungicide for agricultural and horticultural use.

[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, USP. No. 5,106,985 states that the following compounds are useful as insecticides.

[0003]

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[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel pyrrole compound which can be synthesized industrially advantageously, is a safe and effective fungicide for agricultural and horticultural use.

[0005]

The present invention provides a compound of the general formula (I)

[0006]

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[0007] wherein, R ¹ represents a cyano group, a carbamoyl group, a thiocarbamoyl group, a formyl group, hydroxyimino methyl group, a methoxy amino methyl, ethoxy imino-methyl, C ₁ such as propylene alkoximinoalkyl amino methyl, isopropoxycarbonyl alkoximinoalkyl amino methyl _-6 alkoxyiminomethyl group, vinyl, 1-propenyl, chlorovinyl, 1-chloropropenyl, 2-chloropropenyl, 3-chloropropenyl,
Halogen such as 1-chloro-2-butenyl, 1-chloro-3-butenyl 2-chloro-2-butenyl, 2-chloro-3-butenyl, 3-chloro-2-butenyl, 3-chloro-3-butenyl group A C _2-4 alkenyl group optionally substituted with an atom, a C _2-4 alkynyl group _optionally substituted with a halogen atom such as ethynyl, 1-propynyl, propargyl, chloropropargyl group, -C (= S = O) NH
₂ , -C (= NOH) NH ₂ , C _1-4 haloalkylsulfonyl group such as trifluoromethylsulfonyl group, or C _1-4 which may be substituted with a halogen atom such as acetyl, trichloroacetyl, trifluororoacetyl group. Represents an alkylcarbonyl group. R ² is a hydrogen atom, a C _1-6 alkylcarbonyloxymethyl group such as acetoxymethyl or propionyloxymethyl group, or benzoyloxy (which may have a substituent such as a halogen atom, a methyl group, a methoxy group or a nitro group) C _1-6 alkoxycarbonyl group such as methyl group, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl and isopropoxycarbonyl group, C _1-6 alkylsulfonylmethyl group such as methylsulfonylmethyl, ethylsulfonylmethyl and propylsulfonylmethyl group, formyl Groups, C _1-6 alkylcarbonyl groups such as acetyl and propionyl groups, (halogen atoms such as fluorine, chlorine and bromine, C _1-6 alkyl groups such as methyl and ethyl groups, C ₁ such as methoxy and ethoxy groups) _-6 alkoxy group, which may have a substituent such as a nitro group A) a benzoyl group. X is a hydrogen atom, a halogen atom such as fluorine, chlorine or bromine, a cyano group, a C _1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl or t-butyl group, methoxy, ethoxy,
C _1-6 alkoxy groups such as propoxy, isopropoxy, butoxy, t-butoxy groups, chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluroromethyl, trichloromethyl, tribromomethyl, trifluoromethyl, trifluoroethyl groups, etc. Represents a C _1-6 haloalkoxy group such as a C _1-6 haloalkyl group, a trifluoromethoxy group, trifluoroloethoxy, a trichloromethoxy group or a C _1-6 alkylthio group such as a methylthio, methylthio, propylthio, isopropylthio or butylthio group. . Y is a hydrogen atom, a halogen atom such as fluorine, chlorine and bromine, a C _1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl and t-butyl group, methoxy, ethoxy, propoxy, isopropoxy, butoxy, t. - represents C _1-6 alkoxy group or chloromethyl such butoxy, fluoromethyl, bromomethyl, dichloromethyl, Jifururoromechiru, trichloromethyl, tribromomethyl, trifluoromethyl, a C _1-6 haloalkyl group such as trifluoroethyl group . Z represents a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine or iodine, or a C _1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl or t-butyl group. 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. ] The compound represented by these, its manufacturing method, and an agricultural and horticultural germicide.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced, for example, by the method shown below. (Production method-1)

[0009]

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(In the formulae, X, Y, Z ', R ¹ ', m and n have the same meanings as described above.) The compound of the general formula (II) and the general formula (III) and the general formula (IV) The compound is reacted with or without a solvent in a suitable organic solvent at 0 to 150 ° C. in the presence of a trivalent phosphorus compound and a dehydrating agent. Solvents that can be used include hydrocarbons such as benzene and toluene, ethers such as tetrahydrofuran (THF) and dioxane, N, N
Examples include amides such as dimethylformamide (DMF), esters such as ethyl acetate, N, N-dimethylsulfoxide (DMSO), acetonitrile, nitromethane and the like.

Examples of the trivalent phosphorus compound include trialkylphosphines such as trimethylphosphine, triethylphosphine, tripropylphosphine and tributylphosphine, optionally substituted triphenylphosphine, trimethylphosphite, triethylphosphite and tripropyl. Examples thereof include trialkylphosphites such as phosphite and tributylphosphite, and tributylphosphine is particularly preferable. As a dehydrating agent,
Examples thereof include acid anhydrides and dicyclohexylcarbodiimide, and the compound of the general formula (III) is preferably used.

The amount used is 1 to 5 equivalents of the compound of the general formula (III), 1 to 3 equivalents of the compound of the general formula (IV) to 1 equivalent of the compound of the general formula (II), and 0 to 3 equivalents of the trivalent phosphorus compound. ．
It is 5 to 5 equivalents and 1 to 5 equivalents of the dehydrating agent, and a combination of the compounds around the equivalents is particularly preferable. (Production method-2)

[0013]

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(In the formula, X, Y, Z ', R ¹ ', m and n have the same meanings as described above.) A method for producing the compound of the general formula (V) and the general formula (IV)-
Similarly to 1, the reaction is carried out at 0 to 150 ° C. in the presence of a trivalent phosphorus compound and a dehydrating agent in a solvent-free or organic solvent. (Production method-3)

[0015]

[Chemical 21]

(Where X, Y, Z ', V, R ¹ ', m,
n has the same meaning as described above. ) A compound of the general formula (VI) and a compound of the general formula (VII) are reacted at -20 to 150 ° C in the absence of solvent or a suitable organic solvent. At this time, the reaction yield is improved by coexisting the amines or the trivalent phosphorus compound. Examples of amines include tertiary amines such as triethylamine and ethyldiisopropylamine, and 1,8-diazabicyclo [5,4,0] -undecene (DBU). As the solvent and the trivalent phosphorus compound which can be used in the reaction, the same ones as those in the production method-1 can be mentioned. (Production method-4)

[0017]

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(Where X, Y, Z ', V, R ¹ ', m,
n has the same meaning as described above. ) General formula (II), general formula (III) and general formula (VI)
-20 to 1 in the presence of a dehydrating agent and an amine or a trivalent phosphorus compound in a solvent-free or organic solvent with the compound of I).
React at 50 ° C. As the solvent, dehydrating agent and trivalent phosphorus compound which can be used, the same ones as those in the production method-1 can be mentioned. Moreover, as the amines, the same ones as in the production method-3 can be mentioned. (Production method-5)

[0019]

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(In the formula, X, Y, Z ', m and n have the same meanings as described above.) In the general formula (I), the compound in which R ¹ is cyano is PCT.
/ JP95 / 02479 wherein R ¹ is a trifluoromethyl group [general formula (VIII)] can be produced by reacting with ammonia in the presence or absence of a base in a suitable solvent. If no base is used, the reaction is carried out in an autoclave at 100-200 ° C. As the base, metal hydroxide salts such as sodium hydroxide and metal carbonate salts such as sodium carbonate can be used. The amount of base used is 1 to 10 equivalents. When the reaction is carried out in the presence of a base, the reaction proceeds at -20 to 50 ° C under normal pressure. Ammonia can be used in the form of ammonia gas or ammonia water. Examples of the solvent used in the reaction include water, alcohols such as methanol and ethanol, ethers such as THF and dioxane, esters such as ethyl acetate, acetonitrile, DMF, DMSO.
And the like. (Production method-6)

[0021]

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(In the formula, X, Y, Z ', V, m and n have the same meanings as described above.) The compound represented by the general formula (IX) in which R ¹ is cyano can be prepared by a conventional synthetic chemical method. By various methods, R ¹ can be derived to a compound having thiocarbamoyl, amidoxime, or acetyl group. A compound in which R ¹ is thiocarbamoyl can be converted to a compound in which —C (═S═O) NH ₂ is further oxidized. (Production method-7)

[0023]

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[0024] (wherein, X, Y, Z ', m, n are as defined above, R ³ represents a hydrogen atom or a C ₁ ~ ₆ alkyl group.) Represented by the general formula (X) A compound in which the 5-position is a hydrogen atom is P
Its manufacturing method is described in CT / JP95 / 02479. That is, by carrying out the Vilsmeier reaction, the compound of the general formula (X) is converted into the formyl derivative of the general formula (XI), and further reacted with hydroxyamine or alkoxyamines to give the general formula (I).
Wherein R ¹ is a hydroxyiminomethyl group or C _1-6
Compounds of the alkoxyiminomethyl group can be prepared. Further, by reacting the compound of the general formula (X) with trifluoroacetic anhydride in the presence of dimethylaniline, a compound of the general formula (I) in which R ¹ is trifluoroacetyl can be produced.

In any case of carrying out the reaction, the desired product can be obtained by carrying out a usual post-treatment after the completion of the reaction. The structure of the compound of the present invention was determined from IR, NMR, two-dimensional NMR, MS and the like.

[0026]

The present invention will be described in more detail with reference to the following examples, which should not be construed as limiting the invention thereto.

Example 1 2- (3-chlorophenyl) -3- (2-pyridyl)-
Synthesis of 5-formylpyrrole (Compound No. 16)

[0028]

[Chemical formula 26]

DMF 17.23 ml, phosphorus oxychloride 1.
After adding 04 ml (11.12 ml) and heating at 40 degreeC for 20 minutes, it cooled to room temperature. 2- (3-chlorophenyl) -3- (2-pyridyl) pyrrole 2.06 g (8.0
9 mmol) of DMF in 6 ml was added dropwise at room temperature to give 6
After heating at 0 ° C for 2 hours, it is cooled and sodium acetate 17.
32 ml of 22 g aqueous solution was added dropwise. After stirring at room temperature for 20 minutes, water and ethyl acetate were added, the layers were separated, the organic layer was washed with water, dehydrated and concentrated, and the obtained residue was purified by silica gel column chromatography to obtain the desired 5-formyl. In addition to 1.25 g of body, 0.97 g of 4-formyl body was obtained. 5
-55% yield of formyl compound, m.p. p. 156-8 ° C.

Example 2 2- (3-chlorophenyl) -3- (2-pyridyl)-
5-methoxyiminomethylpyrrole (Compound No. 14,
15) Synthesis

[0031]

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2- (3-chlorophenyl) -3- (2-
Pyridyl-5-formylpyrrole 0.28 g (0.99 m
mol) and methoxyamine hydrochloride 0.1 g (1.19 mmo)
l) was added to 10 ml of acetic acid, and sodium acetate 0.1
0 g (1.19 mmol) was added. After stirring at room temperature for 2 hours, water and ethyl acetate were added and the layers were separated. The organic layer was washed with an aqueous sodium carbonate solution, dehydrated and concentrated, and the resulting residue was purified by silica gel column chromatography to isolate two isomers of the target compound. syn form, 0.06 g, yield 19%, m.p. p. 134
-6 ° C. Anti body, 0.17 g, yield 55%, m.p. p.
170-2 ° C.

Example 3 Synthesis of 2- (3,5-dimethylphenyl) -3- (2-pyridyl) -5-cyanopyrrole (Compound No. 3)

[0034]

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2- (3,5-dimethylphenyl) -3-
(2-Pyridyl) -5-trifluoromethylpyrrole 1.
0 g (3.16 mmol) was dissolved in 20 ml of acetonitrile, and 0.81 g (20.3 mmo of sodium hydroxide was added to this solution.
A solution prepared by dissolving l) in 20 ml of concentrated aqueous ammonia was added dropwise at room temperature with stirring. The reaction solution was stirred at room temperature for 1 hour, acetonitrile was distilled under reduced pressure, water and ethyl acetate were added, and the layers were separated. The organic layer was washed with water, dehydrated, and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to obtain 0.74 g of the desired compound. Yield 80%, m.p.
p. 180-2 ° C. When this reaction is carried out at a reaction temperature of 120 to 180 ° C. in an autoclave in the absence of a base, 2- (3,5-dimethylphenyl) -3-with the target compound is obtained.
(2-Pyridyl) -5-carbamoylpyrrole (Compound No. 9) was by-produced.

Example 4 2- (3,5-Dimethylphenyl) -3- (2-pyridyl) -5-thiocarbamoylpyrrole (Compound No. 1
Synthesis of 3)

[0037]

[Chemical 29]

2- (3,5-dimethylphenyl) -3-
(2-pyridyl) -5-cyanopyrrole 1.00 g (3.6
6 mmol) was dissolved in 15 ml of THF, and 0.32 g of triethylamine and 1.23 ml of pyridine were added thereto. Hydrogen sulfide was slowly bubbled in for 2.5 hours with stirring. 3 more
After stirring for an hour, nitrogen gas was blown in to remove excess hydrogen sulfide. Water and ethyl acetate were added to the reaction mixture, the layers were separated, the organic layer was washed with water, dried and concentrated, and the obtained residue was purified by silica gel column chromatography to obtain the desired product.
0.47 g was obtained. Yield 42%, m.p. p. 207-21
2 ° C.

Representative examples of the compounds of the present invention, including the above-mentioned Examples, are shown in Table 1.

[0040]

[Table 101]

[0041]

[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 that occur during cultivation of agricultural and horticultural crops including grass and grass. For example, rice yellow dwarf (Phytophthora macrospora) barley brown snow rot (Pythium spp.) Wheat brown snow rot (Pythium spp.) ) Tobacco blight (Phytophthora parasitica) Sugar beet seedling blight (Pythium spp.) Cucumber downy mildew (Pseudoperonospora cubensis) Tomato blight (Phytophthora infestans) Chinese cabbage downy mildew (Peronospora brassicae) Cabbage downy mildew (Peronospora brassicae) (Phytophthora porri) Rakkyo White plague (Phytophthora porri) Spinach downy mildew (Peronospora spinaciae) Pumpkin plague (Phytophthora capsici) Strawberry plague (Phytophthora nicotianae) Grape downy mildew (Plasmoider aphis) Can be used for control.

Further, in recent years, resistance to acylalanine agents has been developed in various pathogenic bacteria, resulting in insufficient efficacy of these agents, and a drug effective for pathogenic bacteria of resistant strains is desired. The compounds of the present invention are not only sensitive strains,
It is a drug that has an excellent bactericidal effect against pathogenic bacteria of the acylalanine resistant strain. Diseases more preferably applied include downy mildew of cucumber, downy mildew of grapes, and blight of potato. 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 with paints, fibers, etc., it can be used as an antibacterial and antifungal agent for walls, bathtubs, shoes and clothes.

[0044]

[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 agent thus obtained are diluted with water to a predetermined concentration to give a suspension or emulsion, and powders and granules are used as they are for spraying on plants. To be done. The compound of the present invention exerts a sufficient effect when used alone, but may be used in combination with one or more kinds of various fungicides, insecticides, acaricides, or synergists. Fungicides, insecticides, acaricides, nematicides, and plant growth regulators that 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.

Organophosphorus agent: IBP, EDDP, tolclofos-methyl, pyrazophos, fosetyl, etc. Benzimidazole agent: thiophanatemethyl, benomyl, carbendazim, thiabendazole, etc. Dicarboximide agent: iprodione, vinclozolin, procymidone, fluoroimide, etc. Carboxamide agent: oxycarboxy , Mepronil, flutolanil, teclophthalam, trichlamide, pencyclone, etc. Acyl alanine agents: metalaxyl, oxadixyl, furalaxyl, etc.

SBI agents: triadimefon, triadimenol, bitertanol, microbutanyl, hexaconazole, propiconazole, trifumizole, prochloraz, pefurazoate, phenalimol, pyrifenox, triphorin, flucylazole, etaconazole, diclobutrazole, fluotrimazole. , Flutriaphene, Penconazole, Diniconazole, 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: Organophosphorus 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, fenpropatrine, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitrinate, etholin. Fenprox, cycloprotrin, tromethrin, silafluofen, profenprox, acrina suri, etc. Benzoylurea and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, puprofezin, pyriproxyfen, methoprene, benzoepin, diafenthiuron,
Acetamipsodo, imidacloprid, nitenpyram, fipronil, nicotine sulfate, rotenone, cartap, thiocyclam, bensultap, methaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic virus.

Nematicides: fenamiphos, fosthiazate 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 regulators: gibberellins (eg gibberellin A ₃ , gibberellin A ₄ , gibberellin A ₇ ) IAA, NA
A.

[0053]

【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 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalene sulfonate 3 parts Active ingredient 40 by mixing the above uniformly and finely pulverizing
% Wettable powder.

Example Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts By mixing and dissolving the above, an emulsion containing 30% of the active ingredient is obtained.

Example 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 Wet the above and mix until the particle size becomes 1 micron or less Grinding gives a suspension with 10% active ingredient.

[0056]

Next, it is shown in Test Examples that the compounds of the present invention are useful as effective components of various plant disease controlling agents. Regarding the control effect, the control effect was determined by visually observing the degree of growth of lesions and bacterial flora that appeared on the leaves and stems during the survey. 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. Compound No. 1, 2, 3, 4, 5, 6, 6, 7, 8, 1
1, 12, 13

Test Example 2 Grape downy mildew control test Leaves of field-grown 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 ) was spray-inoculated with a suspension of zoospores and kept in a thermostatic chamber (20 ° C.) under illumination for 10 days. 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. Compound No. 1, 2, 3, 4, 5, 6, 7, 8, 13

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yokota cause Odawara, Kanagawa 345 Takada, Odawara Research Institute, Nippon Soda Co., Ltd.

Claims (7)

[Claims] 1. A compound represented by the general formula (I): [Wherein R ¹ is a cyano group, a carbamoyl group, a thiocarbamoyl group, a formyl group, a hydroxyiminomethyl group, C
_1-6 alkoxyiminomethyl group, C _2-4 alkenyl group optionally substituted with halogen atom, C _2-4 alkynyl group optionally substituted with halogen atom, -C (= S = O) NH
_{2, -C (= NOH) NH} 2, C 1-4 haloalkylsulfonyl group or C _1-4 optionally substituted by a halogen atom
Represents an alkylcarbonyl group. R ² is a hydrogen atom, C _1-6
Alkylcarbonyloxymethyl group, (halogen atom,
C _1-6 alkyl group, C _1-6 alkoxy group, optionally substituted by nitro group) benzoyloxymethyl group, C _1-6
Alkoxycarbonyl group, C _1-6 alkylsulfonylmethyl group, formyl group, C _1-6 alkylcarbonyl group or (even if substituted with a halogen atom, C _1-6 alkyl group, C _1-6 alkoxy group, nitro group (Good) represents a benzoyl group which may have a substituent. X represents a hydrogen atom, a halogen atom, a cyano group, a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _1-6 haloalkyl group, a C _1-6 haloalkoxy group or a C _1-6 alkylthio group. Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group or a C _1-6 haloalkyl group. Z represents a hydrogen atom, a halogen atom or a C _1-6 alkyl group. 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. ] The compound represented by these. 2. A compound of the general formula (II) (In the formula, X and m have the same meanings as described above) and the general formula (III) (R ¹ 'CO) ₂ O (III) (wherein R ¹ ' is a hydrogen atom). , A C _2-4 alkenyl group or a C _2-4 alkynyl group which may be substituted with a halogen atom) and a general formula (IV): (In the formula, Y and n have the same meanings as described above, Z ′ represents a hydrogen atom or a C _1-6 alkyl group.), And a trivalent phosphorus compound and a dehydrating agent. Of the general formula (1 ′), characterized by reacting in the presence of (In the formula, X, Y, Z ′, R ¹ ′, m, and n have the same meanings as described above.) A process for producing a pyridylpyrrole compound. 3. A compound represented by the general formula (V): (In the formula, X, R ¹ ′ and m have the same meanings as described above.) And an N-acylglycine represented by the general formula (IV): (In the formula, Y, Z ′, and n have the same meanings as described above.) An ethynylpyridyl compound represented by the formula is reacted in the presence of a trivalent phosphorus compound and a dehydrating agent. (1 ') [Chemical 7] (In the formula, X, Y, Z ′, R ¹ ′, m, and n have the same meanings as described above.) A process for producing a pyridylpyrrole compound. 4. A compound represented by the general formula (VI): (In the formula, X, R ¹ ', and m have the same meanings as described above.) And an oxazolone represented by the general formula (VII) (In the formula, Y, Z ′, n have the same meanings as described above, and V represents a halogen atom.) And a halovinylpyridine represented by the general formula (1 ′) Chemical 10] (In the formula, X, Y, Z ′, R ¹ ′, m, and n have the same meanings as described above.) A process for producing a pyridylpyrrole compound. 5. A compound represented by the general formula (II): (Wherein, X and m have the same meanings as described above) and a phenylglycine represented by the general formula (3) (R ¹ 'CO) ₂ O (III) (wherein R ¹ ' is as defined above). And the same meanings), an acid anhydride represented by the general formula (VII): (In the formula, Y, V, Z ', and n have the same meanings as described above.)
A halovinylpyridine represented by the formula (I) and a dehydrating agent are reacted in the presence of an amine or a trivalent phosphorus compound. (In the formula, X, Y, Z ′, R ¹ ′, m, and n have the same meanings as described above.) A process for producing a pyridylpyrrole compound. 6. A compound represented by the general formula (VIII): (Wherein X, Y, Z ′, m, and n have the same meanings as described above), and reacting 5-trifluoromethylpyrroles with ammonia in the presence or absence of a base. Characterized by the general formula (IX): (In the formula, X, Y, Z ′, m and n have the same meanings as described above.) A process for producing a pyridylpyrrole compound. 7. A compound represented by the general formula (I): (Wherein R ¹ , R ² , X, Y, Z, m, and n have the same meanings as described above) and one or more of the pyridylpyrrole compounds or salts thereof are contained as an active ingredient. A fungicide for agricultural and horticultural use characterized by: