WO2002085852A1 - Pyrrole compound and agricultural or horticultural bactericide - Google Patents

Abstract

A pyrrole compound represented by the formula (1) (1) [wherein R1 represents hydrogen, C¿1-6? alkyl, (C1-6 alkoxy)C1-6 alkyl, (C1-12 alkyl)carbonyl, [(C1-6 alkoxy)C1-6 alkyl]carbonyl, etc.; and A represents a group represented by the following formula (a1) or (a2)] (a1) (a2) or a salt of the compound; and an agricultural or horticultural bactericide containing the compound as the active ingredient.

Description

 Specification

 Compounds and fungicides for agricultural and horticultural use

Technical field:

 The present invention relates to a pyrrole compound or a salt thereof, and a fungicide for agricultural and horticultural use containing the compound as an active ingredient.

Background technology:

 In the cultivation of agricultural and horticultural crops, a large number of control agents are used against crop diseases, but their control efficacy is insufficient, and their use is limited by the emergence of drug-resistant pathogens. From the viewpoint of causing phytotoxicity or contamination of the plant body, or toxicity to humans and fishes and environmental impact, there are not many satisfactory control agents. Therefore, there is a strong demand for a drug that can be used safely with few such disadvantages.

 The pyrrole compounds according to the present invention are described in US Pat. No. 3,876,660 as synthetic intermediates of 4,5-dihalopyrrole derivatives having bactericidal activity. Further, EP206, 523 describes as a synthetic intermediate of a pyrrolyl acrylate compound having a bactericidal activity, but does not disclose that these intermediate compounds have a bactericidal activity. DISCLOSURE OF THE INVENTION:

An object of the present invention, the effect is as providing agricultural and horticultural fungicides reliable and safe to use _c present invention has the formula (1)

[In the formula, R ¹ represents a hydrogen atom, an alkyl group, ₆ alkoxy group, C _l _ _{1 2} alkyl group, Ci-e alkoxy Ci ₆ alkyl group, Jiarukiru force Rubamoiru group, ₆ alkylsulfonyl group, substituted An optionally substituted phenylsulfonyl group, an optionally substituted benzoyl group or an optionally substituted C ₃ _ ₆ cycloalkylcarbonyl group,

A represents a group represented by the following formula, a 1 or a 2,

(Wherein R ² is a nitro group, Shiano group, a halogen atom, C - ₆ alkyl group, C ₂ - ₆ alkenyl le group, C ₂ - ₆ alkynyl group, a mono- or di-alkylamino group, a carboxyl group, d

_ ₆ alkoxycarbonyl group or c ₆ haloalkyl group,

R ³ represents a hydrogen atom, a nitro group, Shiano group, a halogen atom, _ _{1 2} alkyl group, (: I ^ § alkoxy group, C ₂ one ₂ alkenyl groups, ₂ alkynyl group, C ₃ one ₆ cycloalkyl group, Ji A silyl group which may be substituted with a ₁₆ alkylamino group, a ₁₆ haloalkyl group, a phenyl group which may be substituted or an alkyl group,

m represents 0 or an integer of 1 to 4, n represents 0 or an integer of 1 to 3, and when m or n is an integer of 2 or more, R ³ may be different. )

 Q represents an oxygen atom, a sulfur atom, or a nitrogen atom which may be substituted,

 W represents a sulfur atom or an oxygen atom.

However, a compound in which R ¹ is a hydrogen atom and A is an unsubstituted phenyl group, or a compound in which A is 2-methylphenyl or 2-halogenophenyl and R ¹ is a hydrogen atom or a methyl group is excluded. . ] A pyrrole compound or a salt thereof,

 And the general formula (1 ')

[In the formula, R ¹ represents a hydrogen atom, C i-s alkyl group, ₆ alkoxy alkyl group, ₂ alkylcarbonyl groups, C ie alkoxy C _i-6 alkyl Cal Poni group, ₍₆ Jiarukiru force Rubamoiru groups, C Bok ₆ alkyl It represents a sulfonyl group, an optionally substituted off We sulfonyl sulfonyl group, an unsubstituted or may Benzoiru group or may be substituted C ₃ one ₆ cycloalkyl group,

 A represents a group represented by the following formula, a 1 or a 2,

 a1

(Wherein R ² is a nitro group, Shiano group, a halogen atom, - 6 alkyl group, C ₂ - ₆ alkenyl le group, C ₂ - ₆ alkynyl group, a mono- or di-alkylamino group, a carboxyl group, C i — ₆ alkoxycarbonyl group or ds haloalkyl group,

R ³ represents a hydrogen atom, a nitro group, Shiano group, a halogen atom, chromatography Arukiru group, C ^ - _{1 2} § alkoxy group, C _{2 2} alkenyl groups, Ji ₂ - _{1 2} Arukiniru group, C ₃ one ₆ Shikuroarukinore group, d_ 6 alkylamino group, C _1-6 haloalkyl group, optionally substituted phenyl group or C 丄 _ ₆ alkyl optionally substituted silyl group,

m represents 0 or an integer of 1 to 4, n represents 0 or an integer of 1 to 3. When m or n is an integer of 2 or more, R ³ may be different. )

 Q represents an oxygen atom, a sulfur atom, or a nitrogen atom which may be substituted,

W represents a sulfur atom or an oxygen atom. ] It is a fungicide for agricultural and horticultural use, characterized in that it contains one or more kinds of pyrrole compounds or salts thereof represented by the formula:

 In the present invention,

R ¹ is hydrogen atom, methyl, Echiru, propyl, isopropyl, heptyl, sec- heptyl, Isopuchiru, t one heptyl, pentyl and its isomers, hexyl and its isomers, etc. Flip丄- ₆ alkyl group, main Tokishimechiru , Methoxyxethyl, ethoxymethyl, propoxymethyl, alkoxy d-6 alkyl groups such as 3-methoxy-1,2,2-dimethylpropionyl, acetyl, propionyl, butyryl, isoptyryl, 2-methylpentanoyl, 2- Echirupuchi Lil, pivaloyl, Heputanoiru, alkylcarbonyl group lauroyl, main Toki Shiasechiru, ethoxy § cetyl, C WINCH ₆ alkoxy C ^ 6 § Le kill carbonyl group such as main Toki ciprofibrate propionyl group, dimethylcarbamoyl, Jefferies Ji carbamoyl, di propylcarbamate Mor, Jib C ₆ dialkyl force Rubamoiru groups carbamoyl such as methylsulfonyl, E Chirusuruhoniru, propylsulfonyl, C ₆ alkylsulfonyl group such as a butyl sulfonyl, tosyl, any position substituted benzene rings, such as 4 one black port full We sulfonyl sulfonyl A benzoyl group which may be substituted at any position on the benzene ring, such as a phenylsulfonyl group, 2-toluoyl, 3-toluoyl, 4-toluoyl, 4-chlorobenzoyl, or cyclopropylcarbonyl , cyclohexyl carbonyl cyclohexane, it may also be substituted, such as 1-methyl cyclopropane one 1 one carboxymethyl sulfonyl! ^ represents C ₃ _ ₆ cycloalkyl carbonylation Le group.

R ² is a nitro group, a cyano group, a halogen atom such as fluorine, chlorine, bromine or iodine, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isoptyl, t-butyl, pentyl and isomers thereof. cyclohexyl and alkyl groups of the isomers thereof, Eteniru, § Lil, C ₂ of cyclohexenyl, etc., to 2 - ₆ alkenyl group, Echiniru, C ₂ propynyl, etc. - ₆ Arukini group, Mechiruamino, Jimechiruamino, Echiruamino, Jechiruamino, Mechiruechiruami A mono- or di-alkylamino group such as phenyl, carbonyl group, methoxycarbonyl, ethoxycarbonyl or the like; or a C-s haloalkyl group such as trifluoromethyl or chloromethyl.

R ³ is a halogen atom such as 7j elemental atom, nitro group, cyano group, fluorine, chlorine, bromine, iodine, etc. Methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, hexyl and its isomers, heptyl and its isomers, nonyl and its isomers, dodecyl, etc. C ^ -alkyl group, methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, t-butoxy, etc., 2-alkoxy group, ethenyl, 1-probenyl, 2-probenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methynole _ 2-butenyl, 2-methyl-1-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexyl C ₂ one i ₂ alkenyl groups such as alkenyl, Echiniru, 1 one propynyl, 2 - propynyl, 1 one heptynyl, 2-heptynyl, 3-Buchuru, 1 one methyl one 2-propynyl, 2-methyl-one 3-heptynyl, 1 C ₂ such as 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1_methyl-2-butynyl, 2-methyl-13-pentynyl, 1-hexynyl, 1,1-dimethyl-12-butynyl one i ₂ alkynyl group, a cyclopropyl, 1 Mechirushiku port propyl, 2, 2, 3, 3-tetramethyl-cyclopropylcarbamoyl Honoré, cyclobutyl, cyclopentyl Le, cyclohexyl 1-methylcyclopentyl, cyclohexyl, into 1-methylstyrene cycloalkyl, 4 one methyl substituent optionally C ₃ _ ₆ cycloalkyl group which may have a cyclohexyl like cyclohexane, Mechiruamino, Echiru amino, n- Puropiruamino, isopropyl § Mino, C ₆ alkylamino groups such as n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-pentylamino, chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, C haloalkyl groups such as trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl and pentafluoroethyl; phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4 An optionally substituted phenyl group such as -methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl or 4-methoxyphenyl; or methyl, ethyl such as trimethylsilyl, triethylsilyl, dimethylbutylsilyl, etc. It represents propyl, isopropyl, blanking chill, sec- heptyl, Isopuchiru, t one-butyl, pentyl and C i _ ₆ a silyl group optionally substituted with Arukiru its isomers such as its isomers, hexyl contact and.

Q represents an oxygen atom, a sulfur atom, or a hydroxy group, methyl, ethyl, propyl, isopyl, butyl, sec-butyl, isoptyl, t-butyl, pentyl and its isomers, hexyl and its isomers alkyl group, main butoxy, ethoxy, Purobokishi, iso-propoxy, butoxy, sec- butoxy, isobutoxy, C IS alkoxy group such as t- butoxy, 2 _ propenyl Niruokishi, 3- Buteniruokishi C 2 one ₆ Arukeniruokishi such Group, benzyloxy, 2-chlorobenzyloxy, 4-chlorobenzyloxy, 2-methylbenzyloxy, 4-methylbenzyloxy, etc. which may be substituted at any position. To W represents a sulfur atom or an oxygen atom.

m represents 0 or an integer of 1 to 4; n represents 0 or an integer of 1 to 3; when m or n is an integer of 2 or more, R ³ may be different.

 In addition, the salt of the compound according to the present invention refers to a salt that is acceptable in agriculture and horticulture, and is not particularly limited as long as it is a salt that is acceptable in agriculture and horticulture. For example, salts of alkaline earth metals such as magnesium and calcium, metal salts such as iron, copper, zinc, nickel, cobalt, tin and manganese, and salts of acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, and acetic acid. No. Embodiment of the invention:

 The compound according to the present invention can be produced by a conventionally known method and is not particularly limited. For example, it can be produced as follows. Manufacturing method 1

(In the formula, A represents the same meaning as defined above, R ¹ 'is 7] with the exception of the c atom represents the same meaning as R ^1, X, Y and Z represents a halogen atom.) I spoon The reaction between the compound (2) and the compound (3) is performed, for example, in an ether solvent such as getyl ether, dibutyl ether, and tetrahydrofuran (THF) at a reaction temperature of 50 ° C to 50 ° C. The compound (1-1) according to the present invention can be produced. Further, the compound (1-1) is treated at a temperature of 120 ° C. in a solvent such as acetone or N, N-dimethylformamide (DMF) in the presence of a base such as potassium carbonate or sodium hydrogen chloride. The compound of the present invention (1-2) can be produced by reacting with R ¹ 'Z (4) at 110 ° C. Manufacturing method 1

(5) (1 -3) (In the formula, A represents the same meaning as described above, R ¹ ″ represents a protecting group such as a phenylsulfonyl group, and Y represents a halogen atom.) Compound (1-1) according to the present invention is I匕合compound (5) with the compound reaction with (3), for example, the presence of a Lewis acid such as boron trifluoride 'Jechirue one ether complex, dichloromethane. Jikuroroe chlorinated solvent such as Tan, one ² After reacting at 0 ° C to 40 ° C to obtain the conjugate (1-3), the mixture is further refluxed in a solvent such as methanol and water in the presence of a base such as sodium hydroxide. Can be produced by deprotection.

 The salt of the compound according to the present invention can be produced by a conventionally known method. Since the compound of the present invention has excellent bactericidal activity against a wide variety of filamentous fungi, it can be used for controlling various diseases which occur during the cultivation of agricultural and horticultural crops including flowers, turf and pasture. . In particular, it is suitable as a controlling agent for common bean gray mold (Botry ti cs i c i n e r e a).

 The compound of the present invention can also be used as an antifouling agent for preventing 7j living organisms from adhering to underwater contacts such as ship bottoms and fish nets.

 Further, by mixing the compound according to the present invention into paints, fibers, and the like, it can be used as an antibacterial and antifungal agent for walls and bathtubs, shoes and clothes.

When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be in a form that can be taken by a general pesticide for the purpose of use as a pesticide, that is, a wettable powder, a granule, a powder, It can also be used in the form of emulsions, aqueous solvents, suspensions, flowables, wettable powders and the like. When solid additives are used as additives and carriers, vegetable powders such as soybean grains, flour, etc., and mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc. Organic and inorganic compounds such as powder, sodium benzoate, urea, and sodium sulfate are used. For liquid dosage forms, kerosene, xylene and petroleum-based aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trifluoroethylene, methyl iso- Use butyl ketone, mineral oil, vegetable oil, water, etc. as solvents. In order to obtain a uniform and stable form in these preparations, a surfactant may be added, if necessary. Examples of the surfactant include, but are not limited to, alkyl phenyl ether to which polyoxyethylene is added, alkyl ether to which polyoxetylene is added, higher fatty acid ester to which polyoxetylene is added, and polyoxyethylene. Nonionic surfactants such as sorbitan higher fatty acid esters added with xixylene, tristyryl ether added with polyoxetylene, and ester sulfates of alkylphenyl ethers added with polyoxetylene Salts, Alkylbenzene Sulfonates, Higher Alcohol Sulfates, Alkyl Naphthalene Sulfonates, Polycarboxylates, Lignin Sulfonates, Alkyl Naphthalenesul Examples include a formaldehyde condensate of folate and a copolymer of isoptylene-maleic anhydride. Further, the amount of the active ingredient is preferably from 0.01 to 90% by weight, more preferably from 0.05 to 85% by weight. The wettable powders, emulsions and flowables thus obtained are used as a suspension or emulsion by diluting them to a predetermined concentration with water, and the powders and granules are used as they are sprayed on plants.

 Although the compound according to the present invention exerts a sufficient effect by itself, it can 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 in combination with the compound of the present invention include the following.

 Fungicide:

Copper agent:

 Basic copper chloride, basic copper sulfate, etc.

Sulfur agent:

 Thiuram, maneb, mancozeb, polycarbamate, propineb, ziram,

Zineb etc.

Polyhaloalkylthio agent:

 Captan, dichlorfluanid, phorpet, etc.

Organic chlorine agent:

 Chlorothalonil, fthalide, etc.

Organic phosphorus agent:

 IBP, EDDPP, Torque mouth phosmethyl, pyrazophos, Josetyl, etc.

Benzimidazole agent:

 Thiophanemethyl, Benominole, Carbendazim, Thiabendazole, etc.

Dicarboximide agent:

 Iprodione, vinclozolin, procymidone, fluorimide, etc.

Carboxamide agent:

 Oxycarboxin, mepronil, flutranil, techmouth phthalam, tricl

 Mid, Pencyclone, etc.

Asylalanine agent:

 Metalaxinole, Oxazidizole, Furalaxizole, etc.

 SBI agent:

 Triadimefon, Triadimenol, Vitelenol, Microbutanil, Heki

Saconazole, Propiconazole, Trifmizol, Prochloraz, Difrazoe

, Fenarimozore, pyrifenox, trifolin, fursilazole, etaco

Nazole, diclobutrazol, fluotrimazole, flutriaphen, pen Conazole, dicononazole, cyproconazole, imazalil, tridemorph, fenpropimorph, butiobeto, epoxyconazole, metconazole, etc. Antibiotics:

 Polyoxin, blasticidin S, kasugamycin, paridadamycin, dihydrostreptomycin sulfate, etc.

Other:

 Propamocalp hydrochloride, quintozene, hydroxyisoxazolyl, metasulfocarb, anilazine, isoprothiolane, probenazol, quinomethionate, dithianone, dinocab, diclomedine, mepanipyrim, pherimson, fluazinam, pyroquilonate, tricyclazolone , Dithianone, iminoctadine sulphate, simoxanil, pyrrolnitrin, metasulfocarb, jetfencarp, pinapacryl, lecithin, baking soda, phenaminosulf, dozine, dimetmorph, phenazine oxide, etc.

 Insecticide · Acaricide:

Organophosphorus and carbamate insecticides:

 Fenthion, phennitrothion, diazinon, chlorpyrifos, ESP, palmidothion, fentoate, dimethoate, formotione, marathon, trichlorfon, thiomethone, phosmet, dichlorvos, acepheito, EPBP, methyl parathion, methyl parathion. Ethion, salithion, cyanophos, isoxathion, pyridafunthion, hosalon, methidathion, sulfophos, chlorfenvinphos, tetrachlorovinphos, dimethylvinphos, propaphos, isofanphos, ethylthiomethone, propinophos, pyraclophos, monoclothophos. , Azinphos-methyl, aldicarb, methomil, thiodicarp, carbofuran, carbosulfan, benfracarb, fratiocar , Provo sake, B P M C, MTM C, M I P C, force Rubariru, pirimicarb, Echiofu Wenkarupu, Fuenokishikarupu like.

 Pyrethroid insecticides:

 Permethrin, cypermethrin, deltamethrin, humvalerate, phenpropratrine, pyrethrin, arethrin, tetramethrin, resmethrin, dimesulin, propasulin, phenothrin, prothrin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cyclophenitol , Tralomethrin, silafluofundin, acrinasuri, etc.

Benzoylurea and other insecticides:

Difluvenzuron, chlorfurezuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, puprofezi , Pyriproxyfen, methoprene, benzepin, diafenthiuron, acetamipsod, imidacloprid, ditenviram, fipronizole, nicotine sulfate, rotenone, cartap, thiocyclam, bensultap, metaldehyde, mechanical oil, BT and insect pathogen Microbial pesticides such as viruses.

Nematicide:

 Fenamiphos, phosthiazetate, etc.

Acaricide:

 Chlorbenzylate, phenylisobromolate, dicophor, amitraz, BPP

S, benzomate, hexithiax, acid fenibutatin, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin

, Clofentetine, sihexatin, pyridaben, fenpyroximate, tebufenvirad, pyrimidifene, pentochalp, dienochlor and the like.

Plant growth regulator:

 Gibberellins (eg gibberellin A3, gibberellin A4, gibberellin A7),

 I AA, NAA. BEST MODE FOR CARRYING OUT THE INVENTION:

 Next, examples of the compound according to the present invention will be described.

Example 1

 Preparation of 2- (2-trifluoromethylbenzoyl) pyrrol (Compound No. 18)

To a solution of 8.23 g (0.123 mol) of pyrrole in 123 ml of dry THF, 4 lml of a 3.0 M getyl ether solution of ethylmagnesium bromide was added dropwise at 0 ° C under a nitrogen atmosphere. After stirring at room temperature for 30 minutes, this solution is added to a dry THF 123 ml solution of 2-trifluoromethylbenzoic acid chloride at 0 ° C under a nitrogen atmosphere. After stirring at room temperature for 2 hours, a saturated aqueous solution of ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 1) to obtain 12.58 g of the desired product. Yield 43%, n _D ^I = l. 5521 Example 2 Production of 1-phenylsulfonyl-2- (2-methylbenzoyl) piper (Compound No. 1-36)

A solution of 1.0 g (4.76 mmol) of 1-benzenesulfonylpyrrole and 0.72 g (4.76 mmol) of 2-methylbenzoyl chloride in 1 Om1 of dichloromethane 3. 7 g (48 mmol) was added, and the mixture was stirred at room temperature for 7 days. The reaction solution was carefully poured into water, extracted with chloroform, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 5: 1) to obtain 1.45 g of the desired product. Yield 89%, mp. 212-215. C Example 3 Production of 2- (2-methylbenzoyl) pyrrole (Compound No. 1-1)

To a solution of 13.90 g (42.7 mmol) of 1-phenylsulfonyl-2- (2-methylbenzoyl) pyrrole in 42 ml of methanol was added an aqueous solution of sodium hydroxide (8.54 g (213.5 mmol) of sodium hydroxide. · 42m1) of water was added, and the mixture was heated under reflux for 2 hours. After cooling, the reaction solution was added to saturated aqueous sodium bicarbonate, extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium bicarbonate and saturated saline, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel gel chromatography- (n-hexane: ethyl acetate = 5: 1) to obtain 5.48 g of the desired product. 70% yield, mp. 63-65 ° C

 Representative examples of the compounds according to the present invention produced according to the above Examples are shown in Tables 1 and 2.

The abbreviations in the table have the following meanings.

Me: methyl, Etethyl, Pr: propyl, Bu: butyl, Ph: phenyl, c: shik, t: tertiary, Morph: morpholino table

Table 1 (continued)

Table (continued)

Table 2

Table 1 (continued)

Table I (continued)

Ή-NMR τ - data (CDC1 ₃₎ δ

Compound No. 2-9

 2.40 (s, 3H), 6.40 (m, lH), 6.87 (m, lH), 6.95 (d, lH), 7.28 (m, lH), 7.40 (d, lH), 9.72 (br, lH) Compound number 2-20

 1.28 (s, 9H), 6.32 (m, lH), 7.15 (m, lH), 7.26 (m, lH), 7.42 (s, lH), 9.93 (br, lH) Compound No. 2-21

 1.25 (s, 9H), 6.32 (m, lH), 7.15 (m, lH), 7.28 (m, lH), 9.94 (br, lH) Compound No. 2-28

 3.75 (s, 3H), 6.18 (m, lH), 6.74-7.05 (m, 7H), 7.18-7.31 (m, 2H), 7.52 (d, lH), 9.77 (br, lH) Compound No. 2-63

 2.43 (s, 3H), 6.33 (t, lH), 6.94 (d, lH), 7.05 (d, lH), 7.33 (d, lH), 7.40-7.60 (m, 4H), 7.79 (d, 2H) Compound No. 2-72

6.32 (m, lH), 6.85 (m, lH), 7.14 (d, lH), 7.18 (m, lH), 7.28 (d, lH), 10.6 (br, lH)

(Agricultural and horticultural fungicides)

 Next, some examples of the germicidal 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 over a wide range. Parts in Formulation Examples indicate parts by weight. Formulation Example 1 wettable powder

 Compound of the present invention 40 parts

 Clay 4 8 parts

 Dioctyl sulfosuccinate sodium salt 4 parts

 Lignin sulfonic acid sodium salt 8 parts

If the above are uniformly mixed and finely pulverized, a wettable powder with an active ingredient of 40% is obtained. Formulation Example 2 Emulsion

 10 parts of the compound according to the present invention

 Solbesso 2 0 0 5 3 parts

 Cyclohexanone 2 6 parts

 Dodecylbenzenesulfonic acid calcium salt 1 part

 Polyoxyethylene alkylaryl ether 10 parts

By mixing and dissolving the above, an emulsion containing 10% of the active ingredient is obtained. Formulation Example 3 Suspension

 10 parts of the compound according to the present invention

 Sodium lignin sulfonate 4 parts

 Sodium dodecylbenzenesulfonate 1 part

 Xanthan gum 0.2 parts

 Water 84.8 parts

If the above ingredients are mixed and wet-pulverized until the particle size becomes 1 qu or less, the active ingredient 10

% Suspension is obtained. Industrial applicability:

Test examples show that the compounds according to the present invention are useful as active ingredients of various plant disease controlling agents. The control effect was determined by visually observing the diseased state of the test plant at the time of the survey, that is, the degree of growth of the diseased flora that appeared on the leaves, stems, and the like, and comparing it with the untreated one to determine the control effect. Test example 1 Apple scab control test (prevention test) The emulsion of Example 5 was sprayed on apples (variety “Kunimitsu”, 3-4 leaf stage) grown in unglazed pots at a concentration of 200 Ppm of the active ingredient. After air drying at room temperature, conidia of the apple scab (Venturiainaequa 1 is) were inoculated and kept in a high humidity constant temperature room (20 ° C) where light and dark were repeated every 12 hours for 2 weeks. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed excellent control values of 75% or more. The compound number corresponds to the compound number in Tables 1 and 2.

 Compound number: 1—2, 1—13, 1—30, 2—5, 2—7, 2—19, 2—22, 2—23, 2—26, 2—41, 2—43, 2—65 , 2-68, 2-90, 2-91 Test Example 2 Test for controlling bean gray mold (prevention test)

 The flowers of the kidney beans (variety “Nagauzura”) cultivated in the nursery vat were excised, and the emulsion of Example 5 was immersed in a chemical solution adjusted to a concentration of 200 Ppm of the active ingredient. After immersion, it was air-dried at room temperature and spray-inoculated with a spore suspension (containing glucose and yeast extract) of Botrytis cinerea. The inoculated flowers were placed on untreated bean leaves and kept in a high-humidity constant temperature room (20 ° C) where light and dark were repeated every 12 hours for 7 days. The lesion diameter on the leaves was compared with that of untreated leaves, and the control effect was determined. As a result, the following i-danied products showed excellent control values of 75% or more. Incidentally, the compound numbers correspond to the compound numbers in Tables 1 and 2.

 Compound No .: 1-1, 1-2, 1-1-3, 1-18, 1-19, 1-110, 1-11, 1-113, 1-114, 1-15, 1-119, 1-20 , 1-22, 1-123, 1-124, 1-126, 1-130, 1-131, 1-134, 1-147, 1--48, 1-151, 1-152, 1-154, 1 1 55, 1 1 58, 1-61, 1 1 66, 2-2, 2-3, 2-4, 2-5, 2_6, 2-7, 2-8, 2-9, 2-11, 2 -12, 2-16, 2-22, 2-26, 2-30, 2-3 1, 2-33, 2-35, 2-37, 2-38, 2-41, 2-43, 2- 51, 2-60, 2-61, 2-63, 2-64, 2-65, 2_66, 2-67, 2-68, 2-69, 2-71, 2-72, 2-73, 2- 74, 2-75, 276, 2-77, 2-80, 2-81, 2-83, 2-88, 2-89 Test Example 3 Grape downy mildew control test (prevention test)

 The emulsion of Example 5 was sprayed on the grape seedlings (variety “Koshu”, 2 leaf stage) grown in an unglazed pot at a concentration of 200 ppm of the active ingredient. After air drying at room temperature, grape downy mildew (Pla sm

A zoosporang suspension of 0 paravititicola) was spray-inoculated and kept in a high humidity constant temperature room (20 ° C) where light and dark were repeated every 12 hours for 10 days. The appearance of lesions on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds showed excellent control values of 75% or more. Incidentally, the compound numbers correspond to the compound numbers in Tables 1 and 2.

 No .: 1 30, 30, 40, 1 49, 2-1, 2-19, 2-70, 2-89

Claims

 The scope of the claims

Equation (1)

[Wherein, R ¹ is a hydrogen atom, a ₆ alkyl group, a d- ₆ alkoxy ₆ alkyl group,

₂ alkylcarbonyl group, C i_ ₆ alkoxy alkyl group, C - ₆ Jiarukiru force Rubamoiru group, d-6 alkylsulfonyl group, an optionally substituted off We sulfonyl sulfonyl group, it may also be substituted, Benzoinore group, substituted and also good C ₃ one ₆ cycloalkyl carboxymethyl sulfonyl group which may be substituted represents an Tenoiru group,

 A represents a group represented by the following formula, a 1 or a 2,

 a2

 a1

(Wherein R ² is a nitro group, Shiano group, a halogen atom, C i-s alkyl group, C ₂ - ₆ alkenyl le group, C ₂ one ₆ alkynyl group, a mono- or di-Ji Bok ₆ Arukiruamino group, a carboxyl group, C ₁ _ ₆ alkoxycarbonyl group or C haloalkyl group,

R ³ represents a hydrogen atom, a nitro group, Shiano group, a halogen atom, ₂ an alkyl group, _{1 2} § alkoxy group, C ₂ Iche ₂ alkenyl groups, C ₂ _ _{1 2} alkynyl group, C ₃ - ₆ cycloalkyl group, ₆ alkylamino group, C i-open alkyl group, phenyl group which may be substituted or silyl group which may be substituted with C ₆ alkyl group,

m represents 0 or an integer of 1 to 4, n represents 0 or an integer of 1 to 3, and when m or n is an integer of 2 or more, R ³ may be different. )

 Q represents an oxygen atom, a sulfur atom, or a nitrogen atom which may be substituted,

 W represents a sulfur atom or an oxygen atom.

However, a compound in which R ¹ is a hydrogen atom and A is an unsubstituted phenyl group, or a compound in which A is 2-methylphenyl or 2-octanogenophenyl and ¹ is a hydrogen atom or a methyl group is excluded. . And a salt thereof.

2. Equation (1 ')

[Wherein, R ¹ is a hydrogen atom, a ₆ alkyl group, a C ₆ alkoxy C— ₆ alkyl group, a C! _! ₂ alkylcarbonyl group, a C alkoxy C i—e alkyl carbonyl group, a C ₆ alkylalkyl group] It represents ₆ cycloalkyl group, - Rubamoiru group, one ₆ alkylsulfonyl group, an optionally substituted off We sulfonyl sulfonyl group, which may be also good Benzoiru or substituted substituted C ₃

 A represents a group represented by the following formula, a 1 or a 2,

(Wherein R ² is a nitro group, Shiano group, a halogen atom, - 6 alkyl group, C ₂ - ₆ alkenyl le group, C ₂ one ₆ alkynyl group, a mono- or di - 6 alkylamino group, a carboxyl group, C i one ₆ alkoxy force Ruponiru group or C i_ ₆ haloalkyl group,

R ³ represents a hydrogen atom, a nitro group, Shiano group, a halogen atom, _{1 2} alkyl group, Ji § alkoxy group, c ₂ one _{1 2} alkenyl group, c ₂ - _{1 2} alkynyl group, c ₃ _ ₆ cycloalkyl group, c —

_{A 6} alkylamino group, a Cie haloalkyl group, an optionally substituted phenyl group, or a —6 alkyl optionally substituted silyl group,

m represents 0 or an integer of 1 to 4, n represents 0 or an integer of 1 to 3. When m or n is an integer of 2 or more, R ³ may be different. )

 Q represents an oxygen atom, a sulfur atom, or a nitrogen atom which may be substituted,

W represents a sulfur atom or an oxygen atom. ] A fungicide for agricultural and horticultural use, characterized in that the fungicide comprises one or more of a pyrrole compound or a salt thereof represented by the formula: