JPH09194477A - New pyridylpyrrole compound, its production and agricultural and horticultural germicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a new pyridylpyrrole compound useful as a safely usable agricultural and horticultural germicide, etc., having sure effects by reacting a specific phenylglycine with an acid anhydride and an ethynylpyridine in the presence of a trivalent phosphorus compound and a dehydrating agent. SOLUTION: This new pyridylpyrrole compound (salt) is represented by formula I [R<1> is H, a 1-10C alkyl, a 3-7C cycloalkyl, a 1-4C haloalkyl, etc.; R<2> is H, a 1-6C alkoxymethyl, etc.; X is H, a halogen, a 1-6C (halo)alkyl, a (substituted)phenoxy, etc.; Y is H, a 1-6C (halo)alkyl or a halogen; Z is H, a halogen, a 1-6C alkyl or nitro; (m) is 0-5; (n) is 0-4] and is useful as a safely usable agricultural and horticultural germicide, etc., having sure effects. The compound is obtained by reacting a phenylglycine represented by formula II with an acid anhydride and an ethynylpyridine represented by formula III (Z' is H or a 1-6C alkyl) in the presence of a trivalent phosphorus compound and a dehydrating agent.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyridylpyrrole compound, a production method and an agricultural / 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, USP. No. 5106985 describes 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 compound which can be synthesized industrially advantageously, can be used as a fungicide for agricultural and horticultural use with certain effects and safe use.

[0005]

The present invention is a pyridylpyrrole compound represented by the formula [I], a manufacturing method and an agricultural / horticultural fungicide.

[0006]

[Chemical 21]

[In the formula, R ¹ represents a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or other straight or branched C _1- C ₁₀ alkyl group, C _1-4 haloalkyl group such as trifluoromethyl, pentafluoroethyl, trichloromethyl, difluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl,
C _3-7 cycloalkyl group such as cyclohexyl, aralkyl group such as benzyl, C _1-6 alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, t-butoxycarbonyl, fluorine,
It represents a phenyl group which may be substituted with a halogen atom such as chlorine and bromine, and a halogen atom such as phenyl, 3-chlorophenyl and 4-chlorophenyl.

R ² is a hydrogen atom, a C _1-6 alkoxymethyl group such as methoxymethyl or ethoxymethyl, or a C _1-6 such as acetyloxymethyl or propionyloxymethyl.
_1-6 represents an alkylcarbonyloxymethyl group. X is
Hydrogen atom, halogen atom such as fluorine, chlorine and bromine, methyl, ethyl, propyl, isopropyl, butyl, t-
Linear or branched C such as butyl, pentyl, hexyl
_1-6 alkyl group, C _1-6 alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy, hexyloxy, C ₁ such as trifluoromethyl, trifluoroethyl, pentafluoroethyl, etc. _{-6 represents a} haloalkyl group or a phenoxy group which may have a substituent.

Y is a hydrogen atom, a linear or branched C _1-6 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl and hexyl, trifluoromethyl, trichloromethyl, trifluoro. It represents a C _1-6 haloalkyl group such as ethyl and pentafluoroethyl, and a halogen atom such as fluorine, chlorine and bromine. Z
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 or a nitro group. Represent m is 0
Represents an integer of 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. ]

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention can be produced by the following method. Manufacturing method (1)

[0011]

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In the formula, X, Y, m and n have the same meanings as described above, and R ¹ 'is a hydrogen atom, a C _1-10 alkyl group, a C _3-7
Represents a cycloalkyl group, an aralkyl group, a C _1-4 haloalkyl group, a C _1-6 alkoxycarbonyl group, a phenyl group (which may be substituted with a halogen atom) or a halogen atom, and Z ′ represents a hydrogen atom, a halogen atom, Represents a C _1-6 alkyl group or a nitro group. Compound [II] and compound [III
] And compound [IV] are reacted in the absence of solvent or in a suitable organic solvent at 0 ° C. to 150 ° C. in the presence of a trivalent phosphorus compound and a dehydrating agent. The reaction proceeds with the generation of CO ₂ . As a solvent that can be used in the reaction,
Examples thereof include hydrocarbons such as benzene and toluene, ethers such as THF, amides such as DMF, esters such as ethyl acetate, DMSO, acetonitrile and nitromethane.

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.

Examples of the dehydrating agent include acid anhydrides and dicyclohexylcarbodiimide.
] The compound represented by the following is preferably used. The amount of the compound [III] 1 to be used is 1 equivalent of the compound [II].
To 5 equivalents, the compound [IV] is 1 to 3 equivalents, the trivalent phosphorus compound is 0.5 to 5 equivalents, and the dehydrating agent is 1 to 5 equivalents, and a combination of the compounds before and after the equivalents is particularly preferable. Manufacturing method (2)

[0015]

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[In the formula, X, R ¹ ′, Y, Z ′, m and n have the same meanings as described above. The compound [V] and the compound [IV] are reacted at 0 to 150 ° C. in the presence of a trivalent phosphorus compound and a dehydrating agent in the absence of solvent or in the organic solvent as described above. The reaction proceeds with the generation of CO ₂ . Manufacturing method (3)

[0017]

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[Wherein X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] Compound [VI] and compound [IV] in a solvent or in an organic solvent as described above in the presence of a trivalent phosphorus compound, 0 to 150
React at ° C. Manufacturing method (4)

[0019]

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[In the formula, X, Y, R ¹ ′, V, m and n have the same meanings as described above. ] Compound [VI] and compound [VII] in the absence of solvent or in a suitable organic solvent in the presence of a trivalent phosphorus compound, 0 ° C to 150 ° C
React with. Examples of the solvent that can be used in the reaction include hydrocarbons such as benzene and toluene, ethers such as THF, amides such as DMF, esters such as ethyl acetate, DMSO, acetonitrile, nitromethane and the like. Examples of the trivalent phosphorus compound include trimethylphosphine, triethylphosphine,
Trialkylphosphine such as tripropylphosphine and tributylphosphine, and triphenylphosphine which may have a substituent, trimethylphosphite, triethylphosphite, tripropylphosphite, trialkylphosphite such as tributylphosphite and the like. To be Manufacturing method (5)

[0021]

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[In the formula, X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] Compound [II] and compound [III] and compound [VII] are reacted at 0 ° C to 150 ° C in the absence of solvent or in the organic solvent as described above in the presence of a dehydrating agent and amines or a trivalent phosphorus compound. Let Further, when Z is a nitro group or a halogen atom, it can also be produced by the following method.

[0023]

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That is, a compound in which Z is a nitro group or a halogen can be produced by nitrating or halogenating a compound in which Z is a hydrogen atom by an ordinary synthetic chemical method.

[0025]

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A compound in which R ¹ is CF ₃ is hydrolyzed and decarboxylated with an alkali to produce a compound in which both R ¹ and Z are hydrogen atoms, and further halogenated, whereby R ¹ is halogenated. Compounds can also be prepared.
The structure of the compound of the present invention has two-dimensional N
Determined by MR, IR, MS, etc.

[0027]

The present invention will be described in more detail with reference to the following examples. Example 1 5- (3-chlorophenyl) -3- (2-pyridyl)-
Synthesis of 2-trifluoromethylpyrrole (Compound No. 2)

[0028]

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4- (3-chlorophenyl) -2-trifluoromethyl-2,5-sihydrooxazolin-5-one 5.27 g (20 mmol) and 2-ethynylpyridine 2.06 g (20 mmol) were added to 20 ml of benzene. , 4.04 g of tributylphosphine with stirring (20 mm
ol) was added dropwise. The reaction mixture was heated under reflux for 20 minutes and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.52 g of the desired product. Yield 21% m. p 135-140 ° C

Example 2 5- (3-chlorophenyl) -4-nitro-3- (2-
Synthesis of Pyridyl) -2-trifluoromethylpyrrole (Compound No. 16)

[0031]

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5- (3-chlorophenyl) -3- (2-
Pyridyl) -2-trifluoromethylpyrrole 1.60
g (4.96 mmol) was dissolved in 50 ml of acetic anhydride,
0.50 ml of fuming nitric acid was added dropwise at 0 ° C. with stirring. The reaction mixture was stirred at room temperature for 1 hr, poured into ice water, neutralized with aqueous sodium hydroxide solution, and extracted with ether. The ether layer was dehydrated and concentrated, and the resulting residue was purified by silica gel column chromatography to obtain 1.52 g of the desired product. Yield 83% m. p 94-96 ° C

Example 3 5- (3-chlorophenyl) -1-ethoxymethyl-3
Synthesis of-(2-pyridyl) -2-trifluoromethylpyrrole (Compound No. 15)

[0034]

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5- (3-chlorophenyl) -3- (2-
Pyridyl) -2-trifluoromethylpyrrole 0.50
g (1.55 mmol) was dissolved in 15 ml of THF, and 0.35 g (3.1 mmo) of potassium t-butoxide under stirring.
l) was added. After stirring for 10 minutes, 0.30 g (3.1 mmol) of chloromethyl ethyl ether was added dropwise and the mixture was stirred overnight at room temperature. Water and ethyl acetate were added to the reaction solution,
The organic layer was separated, the ethyl acetate layer was dehydrated and concentrated, and the resulting residue was purified by silica gel column chromatography to obtain 0.45 g of the desired product. Yield 76% n _D ^23.4 1.573
6

Example 4 5- (3-Bromophenyl) -2-methyl-3- (2-
Synthesis of pyridyl) pyrrole (Compound No. 32)

[0037]

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3.45 g of 3-bromophenylglycine
(15 mmol), 3.06 g of acetic anhydride (30 mmo
l), 1.55 g of 2-ethynylpyridine (15 mmo
1) was added to 40 ml of toluene, and 3.03 g (15 mmol) of tributylphosphine was added dropwise with stirring. The reaction mixture was heated under reflux for 2 hours, concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.60 g of the desired product. Yield 13% m. p45-47 ° C simultaneously 2- (3-bromophenyl) -5-methyl-3-
Also isolated was 1.25 g (26.6%) of (2-pyridyl) pyrrole. m. p136-137 ° C

Example 5 5- (3-chlorophenyl) -4-methyl-3- (2-
Synthesis of Pyridyl) -2-trifluoromethylpyrrole (Compound No. 13)

[0040]

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4- (3-chlorophenyl) -2-trifluoromethyl-2,5-dihydrooxazolin-5-one 3.95 g (15 mmol), 2- (2-nitro-1)
-Propenyl) pyridine 2.46 g (15 mmol),
Triphenylphosphine (3.93 g, 15 mmol) was added to toluene (15 ml), and the mixture was heated under reflux for 3 hours. The reaction solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain 1.31 g of the desired compound. Yield 26% m. p135-137 ° C Including the above examples,
Representative examples of the compounds of the present invention are shown in Table 1 below.

[0042]

[Table 101]

[0043]

[Table 102]

[0044]

[Table 103]

[0045]

[Table 104]

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 blast ( Pyricularia oryzae ), blight ( Rhizoctonia solani ), boiled scab ( Gibberella fujikuroi), sesame leaf blight ( Cochliobolus miyabeanus ), barley brown smut ( Ustilago nuda ) wheat rust ( 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 ( Botryti s allii) Strawberry powdery mildew ( Sohaerotheca humuli ) Apple powdery mildew ( Podosphaera leucotricha) Scab ( Venturia inaequalis ) Monili ( monilinia mali ) Oyster anthracnose ( Gloeosporium kaki ) Peach ash ( Monilinia fructicola ) disease (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 ( Pennisillium italicum ) It can be used for the control of Western turf snow rot large grain sclerotia ( Sclerotinia borealis ).

Further, in recent years, resistance to benzimidazole-based agents and acylalanine-based 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. There is. The compound of the present invention is a drug having an excellent bactericidal effect not only on susceptible strains but also on pathogenic bacteria resistant to benzimidazole-based agents and acylalanine-based agents. More preferable diseases to be applied include apple scab, cucumber downy mildew, grape downy mildew and the like. The compound of the present invention, the aquatic life is the ship bottom,
It can also be used as an antifouling agent to prevent adhesion to underwater contact objects such as fishnets. 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. Further, some of the compounds of the present invention exhibit insecticidal, acaricidal and herbicidal activities.

[0048]

[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, diram, zineb, etc. Polyhaloalkylthio agent: captan, dichlorfluanid, fol Pets, etc.Organic chlorine agents: Chlorothalonil, phthalides, etc. Organic phosphorus agents: IBP, EDDP, tolclofos-methyl,
Pyrazophos, fosetyl, etc.

Benzimidazole agents: thiophanate methyl, benomyl, carbendazim, thiabendazole, etc. Dicarboximide agents: iprodione, vinclozolin, procymidone, fluorimide, etc. Carboxamide agents: oxycarboxin, mepronil, flutolanil, teclophthalam, trichlamide, pencyclone, etc. acylalanine agents : Metalaxyl, oxadixyl, furaraxyl, etc. SBI agents: triadimefon, triadimenol, bitertanol, microbutanyl, hexaconazole, propiconazole, trifumizole, prochloraz, pefrazoate, phenalimol, pyrifenox, triphorine, flucylazole, etaconazole, diclobutrazole. , Fluotrimazole, flutriafen, penconazole, di Niconazole, cyproconazole, imazalil, tridemorph, fenpropimorph, butiobate, etc.

Antibiotics: polyoxine, 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, cycloprothrin, tromethrin, silafluofen, brofenprox, acrina suri, etc. Benzoylurea and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, cartap, thiocyclam, bensultap, benzoepin, Diafenthiuron, acetamiprid, nitenpyram, imidacloprid, fipronil, nicotine sulfate, rotenone, methaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses, and the like.

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.

[0056]

【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 6 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfuric acid ester 4 parts Alkylnaphthalene sulfonate 3 parts If the above is uniformly mixed and finely ground, the active ingredient 40
% Wettable powder.

Example 7 Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts If the above components are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained.

Example 8 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.

Test Example 1 Cucumber downy mildew control test Cucumber cultivated in unglazed pot (variety "Sagamihanjiro")
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.). As a result of investigating the control effect by comparing the appearance state of lesions on the leaves with that of no treatment, the following compounds showed an excellent control effect of 75% or more. Compound No. in Table 1 2, 7,
8, 9, 13, 16, 17, 27, 32, 34, 40,
42

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) a zoosporangia suspension is spray inoculation was held for 10 days in a constant temperature chamber under illumination (20 ° C.). As a result of investigating the control effect by comparing the appearance state of lesions on the leaves with that of no treatment, the following compounds showed an excellent control effect of 75% or more. Compound No. in Table 1 32, 33, 34,
43

Test Example 3 Apple scab control test: Apple seedlings (cultivar "Kunimitsu", 3
~ 4 leaf stage), the emulsion of the compound of the present invention, the active ingredient 200p
Sprayed at a concentration of pm. After spraying, it is naturally dried at room temperature, and then scab ( Venturia inaequali)
s 2 ) inoculated with conidia and kept in a high humidity constant temperature room (20 ° C.) where light and dark are repeated every 12 hours for 2 weeks. As a result of investigating the control effect by comparing the appearance state of lesions on the leaves with that of no treatment, the following compounds showed an excellent control effect of 75% or more. Compound No. in Table 1 5, 6, 9, 32

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location (C07D 401/04 207: 42 213: 16) (C07D 401/04 207: 323 213: 61) ( (C07D 401/04 207: 325 213: 16) (72) Inventor Yokota, 345 Takada, Odawara, Kanagawa Pref., Odawara Research Institute, Nippon Soda Co., Ltd.

Claims (7)

[Claims] 1. A compound of the formula [I] [In the formula, R ¹ represents a hydrogen atom, a C _1-10 alkyl group, a C _3-7
It represents a cycloalkyl group, an aralkyl group, a C _1-4 haloalkyl group, a C _1-6 alkoxycarbonyl group, a phenyl group (which may be substituted with a halogen atom) or a halogen atom. R ² is a hydrogen atom, a C _1-6 alkoxymethyl group, C
_1-6 represents an alkylcarbonyloxymethyl group. X is
It represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _1-6 alkoxy group, a C _1-6 haloalkyl group or a phenoxy group which may have a substituent. Y is a hydrogen atom, C
_{It represents a 1-6} alkyl group, a C _1-6 haloalkyl group or a halogen atom. Z represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a nitro group. m represents an integer of 0 to 5, and when 2 or more, X may be different from each other. n is 0 to 4
Represents an integer of 2 and when Y is 2 or more, Y may be different from each other. ] The pyridyl pyrrole compound represented by these, or its salt. 2. A compound of the formula [II] [In the formula, X and m represent the same meaning as described above. And a phenylglycine represented by the formula [III] (R ¹ ′ CO) ₂ O [III] [in the formula, R ¹ ′ is a hydrogen atom, a C _1-10 alkyl group, C _{3- 7}
It represents a cycloalkyl group, a C _1-4 haloalkyl group, a C _1-6 alkoxycarbonyl group, a phenyl group (which may be substituted with a halogen atom) or an aralkyl group. ] And an acid anhydride represented by the formula [IV] [In formula, Y and n represent the same meaning as the above. Z'is
It represents a hydrogen atom or a C _1-6 alkyl group. ] The ethynylpyridines represented by the formula [I '] are characterized by reacting with a trivalent phosphorus compound and a dehydrating agent. [In the formula, X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] The manufacturing method of the pyridyl pyrrole compound represented by these. 3. The formula [V]: [In the formula, X, R ¹ ′ and m have the same meanings as described above. ] N-acylglycines represented by the formula [IV] [In the formula, Y, Z ′, and n have the same meanings as described above. ] Reacted with ethynyl pyridines represented by the formula [I ′] embedded image in the presence of a trivalent phosphorus compound and a dehydrating agent. [In the formula, X, Y, Z ′, R ¹ ′, m and n have the same meanings as described above. ] The manufacturing method of the pyridyl pyrrole compound represented by these. 4. The formula [VI]: [In the formula, X, R ¹ ′ and m have the same meanings as described above. ] And an oxazolone represented by the formula [IV] A compound represented by the formula [I '], which is characterized in that it is reacted with an ethynylpyridine represented by the following formula in the presence of a trivalent phosphorus compound. [In the formula, X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] The manufacturing method of the pyridyl pyrrole compound represented by these. 5. The formula [VI]: [In the formula, X, R ¹ ′ and m have the same meanings as described above. ] And an oxazolone represented by the formula [VII] [In the formula, Y, n, and Z'represent the same meaning as described above. ] The nitrovinylpyridines represented by the formula [I '] are characterized by reacting in the presence of a trivalent phosphorus compound. [In the formula, X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] The manufacturing method of the pyridyl pyrrole compound represented by these. 6. A formula [II]: [In the formula, X and m represent the same meaning as described above. ] And a phenylglycine represented by the formula [III] (R ¹ ′ CO) ₂ O [wherein R ¹ ′ has the same meaning as described above. ] And an acid anhydride of the formula [VII] [In the formula, Y, Z ′, and n have the same meanings as described above. ] The nitrovinyl pyridine represented by the formula and a dehydrating agent are reacted in the presence of a trivalent phosphorus compound, and the formula [I '] [In the formula, X, Y, R ¹ ′, Z ′, m and n have the same meanings as described above. ] The manufacturing method of the pyridyl pyrrole compound represented by these. 7. A compound represented by the formula [I]: [In the formula, R ¹ , R ² , X, Y, Z, m and n have the same meanings as described above. ] A fungicide for agricultural and horticultural use, comprising one or more of the pyridylpyrrole compounds represented by the following or salts thereof as an active ingredient.