JPH0519551B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel carbamoylimidazole derivative, a method for producing the same, and a fungicide for agricultural and horticultural use. More specifically, the present invention relates to a carbamoylimidazole derivative represented by the following formula (). General formula: In the formula, ^R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, ^R2 represents a fluoro-substituted lower alkyl group, and X represents an oxygen atom or a sulfur atom. , Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, 3, 4, 5 or 6. The compound of the above general formula () can be produced, for example, by the method described below, and the present invention also relates to such a production method. Manufacturing method: - General formula: In the formula, R ² , X, Y, m and n are the same as above,
And Hal represents a halogen atom, and a compound represented by the general formula: R ¹ -NH ₂ () where R ¹ is the same as above is reacted, and then N,
A method for producing a carbamoylimidazole derivative of the general formula (), which comprises reacting N'-carbonyldiimidazole. The present invention also relates to an agricultural and horticultural fungicide containing the carbamoylimidazole derivative of the general formula () as an active ingredient. Publication known before the filing date of the present application, JP-A-50-31047
The specification of the publication contains the general formula: In the formula, X is oxygen or sulfur, R ¹ is an optionally substituted alkyl group,
... R ² is an optionally substituted phenoxyalkyl group, and it is described that compounds including compounds represented by the following have fungicidal activity. The general formula () of the present invention is conceptually included in the general formula (A) above. However, in the specification of the publication, in the compound specified by the above general formula () of the present invention, a group corresponding to R ² of the above formula (A):

[Formula] is conceptually included, but not only is there no specific description of the group, but there is also no description that suggests such a group. The present inventors carried out synthesis and biological activity screening to create a new compound with excellent control activity against various crop diseases, and as a result, we have now discovered carbamoylmidazole represented by the general formula (). We succeeded in synthesizing a derivative, and discovered that, as will be described in detail later, this compound exhibits a complete control effect at a lower dose than the compound described in the specification of the cited publication. The present invention has been completed based on this discovery. According to the knowledge obtained by the inventors of the present invention, in detail, the compound of the general formula () of the present invention has the general formula The compound (A) is conceptually included. However, in the specification of the publication, in the general formula () specified in the present invention, the group which is the most characteristic:

There is no general disclosure or specific description regarding [Formula], nor any suggestion whatsoever. That is, the group specified by the general formula () of the present invention:

Specific descriptions in the specification of the above publication corresponding to the substituent: -X-R ² in [Formula] are halogen atom, alkoxy group, alkyl group, trihalomethyl group, cyano group, alkylthio group, nitro group, alkyl Only those selected from sulfonyl group, acetyl group, acetamido group, amino group, and dialkylamino group. The compound of general formula () of the present invention is compared with the compound described in the specification of the above-mentioned publication, and as illustrated in the product test examples listed later, the comparative compound exhibits effects against plant diseases. It is a unique compound that maintains extremely excellent bactericidal activity at a low drug concentration that is impossible to achieve, and also exhibits completely unexpected and surprising control efficacy. The compounds of the present invention can be used to treat, for example, rice blast, rice sesame leaf blight, tomato late blight, cucumber anthracnose,
Against powdery mildew of cucumbers and bakanae disease of rice,
Compared to the compounds described in the specifications of the above-mentioned publications, it exhibits extremely superior, unexpected and surprising pesticidal efficacy. Therefore, according to the research of the present inventors,
Although the compound of formula (), which No. 31047 does not specifically disclose or suggest, may be conceptually included in the formula (A), it does not include the compounds mentioned in the specification of the publication. It has been found that this compound achieves a new technical effect that was completely unrecognized in the specification of the publication, in that it exhibits a completely unexpected and surprisingly excellent bactericidal effect at a certain dosage. Therefore, an object of the present invention is to provide a carbamoylimidazole derivative of the general formula (), a method for producing the same, and its use as an agricultural and horticultural fungicide. The above objects and many other objects and advantages of the present invention will become more apparent from the following description. The compound of the present invention has strong bactericidal activity against a wide range of plant pathogenic bacteria at low doses, and can control a wide range of plant diseases, not only on agricultural and horticultural crops but also on general plants. It can be applied to The bactericidal spectrum of the compounds of the present invention includes, for example, archaeal fungi (Archimycetes), algal fungi (Phycomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes), incomplete Fungi
Imperfecti)] and various other plant diseases caused by bacteria. As a representative example of the fungicidal spectrum of the compound of the present invention, rice blast disease (Pyricularia
oryzae), rice sesame leaf blight (Ophiobolus
miyabeanus), Gibberella fujikuroi of rice, Sclerotinia sclerotiorum of various crops, Alternaria brassicae, powdery mildew (Sphaerotheca fuliginea), Botrytiscinerea, charcoal of cucurbits Examples include Colletotrichnm lagenarium and Phytophthora infestans. The compound of general formula () of the present invention can be easily produced, for example, by the following method. In the formula, R ¹ , R ² , X, Y, m, n and Hal are the same as above. In the above reaction formula, R ¹ is specifically methyl,
Ethyl, propyl, isopropyl, n-(iso-,
lower alkyl groups such as sec- or tert-)butyl,
a lower alkoxy-lower alkyl group or cyclopropyl having the same lower alkyl group as exemplified above;
Represents a cycloalkyl group having 3 to 8 carbon atoms such as cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl, R ² represents a fluoro-substituted lower alkyl group,
Specifically, trifluoromethyl, 2,2,2-
Examples include trifluoroethyl; represents 0, 1 or 2, n represents 2, 3, 4, 5 or 6, and Hal represents the same halogen atom as in the above example,
Preferably it represents chlor or brome. In the method for producing the compound of the present invention represented by the above reaction formula, specific examples of the compound of general formula () as a raw material include, for example, 2-[4-(2,2,2-trifluoroethylthio)phenoxy]ethyl Bromide, 2-[4-(2,2,2-trifluoroethylthio)-2-troxy]ethyl bromide, 2-[4-(2,2,2-trifluoroethylthio)-3,5-xyloxy ] Ethyl bromide, 2-[2-chloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide, 2-[2,6-dichloro-4-(2,2,2-trifluoro ethylthio)phenoxy]ethyl bromide, 3-[4-(2,2,2-trifluoroethylthio)phenoxy]propyl bromide, 3-[2,6-dichloro-4-(2,2,2-trifluoro Ethylthio)phenoxy]propyl bromide, 4-[4-(2,2,2-trifluoroethylthio)phenoxy]butyl bromide, 4-[4-(2,2,2-trifluoroethylthio)-2- Troxy]butyl bromide, 4-[4-(2,2,2-trifluoroethylthio)-3,5-xyloxy]butyl bromide, 4-[2-chloro-4-(2,2,2-trifluoro Ethylthio)phenoxy]butyl bromide, 5-[4-(2,2,2-trifluoroethylthio)phenoxy]pentyl bromide, 5-[2,6-dichloro-4-(2,2,2-trifluoro Ethylthio)phenoxy]pentyl bromide, 6-[4-(2,2,2-trifluoroethylthio)phenoxy]hexyl bromide, 2-(4-trifluoromethylthiophenoxy)
Ethyl bromide, 2-(2-chloro-4-trifluoromethylthiophenoxy)ethyl bromide, 2-(2,6-dichloro-4-trifluoromethylthiophenoxy)ethyl bromide, 3-(4-trifluoro methylthiophenoxy)
Propyl bromide, 3-(2-chloro-4-trifluoromethylthiophenoxy)propyl bromide, 3-(2,6-dichloro-4-trifluoromethylthiophenoxy)propyl bromide, 4-(4-trifluoro methylthiophenoxy)
Butyl bromide, 4-(2-chloro-4-trifluoromethylthiophenoxy)butyl bromide, 5-(4-trifluoromethylthiophenoxy)
Pentyl bromide, 5-(2-chloro-4-trifluoromethylthiophenoxy)pentyl bromide, 5-(2,6-dichloro-4-trifluoromethylthiophenoxy)pentyl bromide, 2-(4-trifluoro methoxyphenoxy)
Ethyl bromide, 2-(2-chloro-4-trifluoromethoxyphenoxy)ethyl bromide, 2-(2,6-dichloro-4-trifluoromethoxyphenoxy)ethyl bromide, 3-(4-trifluoro methoxyphenoxy)
Propyl bromide, 3-(2-chloro-4-trifluoromethoxyphenoxy)propyl bromide, 3-(2,6-dichloro-4-trifluoromethoxyphenoxy)propyl bromide, 5-(4-trifluoro methoxyphenoxy)
Examples include pentyl bromide, 5-(2-chloro-4-trifluoromethoxyphenoxy)pentyl bromide, 5-(2,6-dichloro-4-trifluoromethoxyphenoxy)pentyl bromide, and the like. In addition, chloride forms thereof can also be mentioned instead of bromide forms. Similarly, specific examples of compounds of the general formula () which are raw materials include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, 2-ethoxyethylamine, cyclopentylamine, and cyclohexylamine. etc. can be exemplified. Next, a representative example will be shown and the above manufacturing method will be specifically explained. The above method for producing the compound of formula () of the present invention) can be carried out desirably using a solvent or a diluent. All inert solvents and diluents can be used for this purpose. Such solvents or diluents include water, aliphatic, cycloaliphatic and aromatic hydrocarbons (which may optionally be chlorinated), such as hexane,
Cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride and trichloroethylene, chlorobenzene; other ethers such as diethyl ether, methyl ethyl ether, di-iso-propyl ether, di- Butyl ether, dioxane, teirahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl-iso-propyl ketone,
Methyl-iso-butylketone; Nitriles e.g.
Acetonitrile, propionitrile, acrylonitrile; alcohols such as methanol, ethanol, iso-propanol, butanol, ethylene glycol; esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones,
Sulfoxides such as dimethyl sulfoxide,
and bases such as pyridine. Furthermore, as described above, the reaction of the present invention can be carried out in the presence of an acid binder. Such acid binders include commonly used alkali metal hydroxides, carbonates, bicarbonates, alcoholates, etc., and tertiary amines such as triethylamine, diethylaniline, pyridine, etc. . The above method can be carried out within a wide temperature range. Generally, it can be carried out between about -20°C and the boiling point of the mixture, preferably between 0 and about 100°C. Further, although it is preferable to carry out the reaction under normal pressure, it is also possible to operate under increased pressure or reduced pressure. The above production method) can be carried out after separating the compound of general formula () as an intermediate product, or can be carried out by continuous reaction without separation. Alternatively, the compound of the present invention can also be produced by the method shown in the following reaction formula. In the formula, R ¹ , R ² , X, Y, m and n are the same as above, and M represents a hydrogen atom or an alkali metal atom. In the above reaction formula, trichloromethylchloroformate (Cl ₃ ) is used instead of phosgene (COCl ₂ ).
COCOCl) can also be reacted. When the compound of formula () of the present invention is used as a fungicide for agriculture and horticulture, it can be used as it is by diluting it directly with water, or by using a method commonly used in the agricultural chemical manufacturing field using an agricultural chemical auxiliary. It can be used in various formulations. In actual use, these various preparations can be used directly or diluted with water to a desired concentration. Examples of agrochemical auxiliaries mentioned here include diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants,
wetting agents), stabilizers, fixing agents, propellants for aerosols,
Mention may be made of synergists. Examples of solvents include organic solvents in addition to water, such as hydrocarbons [e.g., n-hexane, petroleum ether, naphtha, petroleum fractions (paraffin wax, kerosene, light oil, middle oil, heavy oil), benzene, toluene] , xylenes]; halogenated hydrocarbons [e.g., chloromethylene, carbon tetrachloride, trichloroethylene, ethylene chloride, ethylene dibromide, chlorobenzene, chloroform]; alcohols [e.g., methyl alcohol, ethyl alcohol, propyl alcohol, ethylene Ethers [e.g. ethyl ether, ethylene oxide, dioxane]; Alcohol ethers [e.g. ethylene glycol monomethyl ether]; Ketones [e.g. acetone, isophorone]; Esters [e.g. ethyl acetate, amyl acetate]; Amides [for example, dimethylformamide, dimethylacetamide]; sulfoxides [for example, dimethyl sulfoxide]; and the like. Extending agents or carriers include, for example, slaked lime, magnesium lime, gypsum, calcium carbonate,
Inorganic powder particles such as silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. pyrophyllite, talc, montmorillonite, beidellite, vermiculite, kaolinite, mica), etc. For example, vegetable powder such as grain flour, starch, modified starch, sugar, glucose, crushed plant stems, etc.; For example, synthetic resin powder such as phenol resin, urea resin, vinyl chloride resin, etc.; can be mentioned. Examples of the surfactant include anionic surfactants such as alkyl sulfates (e.g., sodium lauryl sulfate), arylsulfonic acids (e.g., alkylaryl sulfonate, sodium alkylnaphthalene sulfonate),
Succinates, polyethylene glycol alkylaryl ether sulfate salts; cationic surfactants, such as alkylamines [such as laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride], polyoxyethylene alkylamine nonionic surfactants, such as polyoxyethylene glycol ethers [e.g., polyoxyethylene alkylaryl ethers and condensates thereof], polyoxyethylene glycol esters [e.g.
polyoxyethylene fatty acid ester], polyhydric alcohol esters [e.g., polyoxyethylene sorbitan monolaurate]; amphoteric surfactants;
etc. can be mentioned. In addition, stabilizers, fixing agents [e.g., agricultural soap, caseinate lime, sodium alginate, polyvinyl alcohol (PVA), vinyl acetate adhesives, acrylic adhesives], propellants for aerosols [e.g.
Trichlorofluoromethane, dichlorofluoromethane, 1,2,2-trichloro-1,1,2-trifluoroethane, chlorobenzene, LNG, lower ether]; Combustion regulator (for smoking agents) [e.g.
Nitrite, zinc powder, dicyandiamide]: Oxygen supply agent [e.g. chlorate]: Efficacy extender: Dispersion stabilizer [e.g. casein, tragacanth, carboxymethyl cellulose (CMC), polyvinyl alcohol (PVA)]: Synergist can be mentioned. The compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Forms of preparations include emulsions, oils, wettable powders, aqueous solutions, suspensions, powders, granules, powders, smoking agents, tablets, aerosols, pastes, capsules, etc. can. The agricultural and horticultural fungicide of the present invention contains, for example, about 0.1 to about 95% by weight of the active ingredient, preferably about 0.5 to about 90% by weight.
% by weight. In actual use, the various formulations and spray preparations described above (ready-to-use)
The active compound content in the preparation is generally approximately
0.0001 to about 20% by weight, preferably about 0.005 to about 10
A range of weight percent is suitable. The content of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and disease occurrence situation. The compounds of the present invention may further be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators, attractants [e.g. Phosphate ester compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds, triazine compounds [compound] or/and fertilizer etc. can also be made to coexist. Various formulations or ready-to-use preparations containing the active ingredients of the invention are available.
Preparation) refers to application methods commonly used in the field of agrochemical manufacturing, such as spraying, spraying, misting, atomizing, dusting, surface application, and pouring. Fumigation: soil application, [e.g.
Admixture, sprinkleling, vaporing, irrigation]: surface application [e.g.
Banding, dressing, coating]: Can be applied by dipping, etc. It can also be applied by the so-called ultra-low-volume spraying method. In this way it is possible to have 100% active ingredient content. The application rate per unit area can be selected as appropriate, e.g. from about 0.03 to about
An example is 10 kg, preferably about 0.1 to about 6 kg.
However, in special cases it is possible to exceed or fall below these ranges.
And sometimes it's even necessary. According to the present invention, it contains a compound of the general formula () as an active ingredient, and a diluent (solvent and/or filler and/or carrier) and/or
Alternatively, an agricultural and horticultural fungicidal composition containing a surfactant and, if necessary, a stabilizer, a fixing agent, and a synergist can be provided. Furthermore, according to the present invention, the compound of the general formula () is applied to pathogens and/or their outbreaks and crop disease outbreak sites either alone or by diluents (solvents and/or fillers and/or carriers) and/or A method for controlling crop diseases can be provided in which a surfactant and, if necessary, a stabilizer, a fixing agent, and a synergist are mixed and applied. EXAMPLES Next, the content of the present invention will be specifically explained with reference to Examples, but the present invention should not be limited thereto. Example 1 To 2-[2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide (2.38 g), n-propylamine (5
g) was added, and after stirring at room temperature for 8 hours and under reflux for 3 hours, excess n-propylamine was distilled off. Water (20ml) and 5% potassium hydroxide aqueous solution (20ml) to the residue
and toluene (100 ml), stir, and separate the organic layer. After washing the organic layer with water, it is dried over anhydrous sodium sulfate. The residue (2.16 g) obtained by distilling off low-boiling substances under reduced pressure is N with a refractive index of n ²⁰ _D 1.5210.
-{2-[2,6-dichloro-4-(2,2,2-
trifluoroethylthio)phenoxy]ethyl}
-N-propylamine, but without purification, this residue (2.16 g) was mixed with toluene (10 ml) and N,N'-
Add carbonyldiimidazole (1.7g),
Stir at 50° C. for 3 hours and under reflux for 6 hours. After cooling, add toluene (60 ml), wash with water, and dry with anhydrous sodium sulfate. When toluene is distilled off, the desired 1-{N-2-[2,
6-dichloro-4-(2,2,2-trichloroethylthio)phenoxy]ethyl-N-propylcarbamoyl}imidazole (2.2 g) is obtained. Compounds of the present invention synthesized in the same manner as in the above examples are shown in Table 1 below.

【table】

【table】

【table】

[Table] 2 used as a synthetic raw material in Example 1 above
A synthesis example of -[2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide is shown below as a reference example. Reference example Metallic sodium (0.7g) in ethanol (50ml)
2,6-dichloro-4-(2,2,2
-Trifluoroethylthio)phenol (8.9g)
and ethylene bromide (20 g) were added, and the mixture was stirred at 40°C for 2 hours and under reflux for 4 hours. The residue obtained by distilling off ethanol and excess ethylene bromide is taken up in toluene (150 ml), washed successively with a 5% aqueous potassium hydroxide solution and water, and dried over anhydrous sodium sulfate. After distilling off toluene, distillation was performed under reduced pressure to obtain 2-[2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide (7.2 g) represented by the following formula. It will be done. bp.124～126℃/0.8mmHg By the same method as in the above reference example, the above general formula () which is a raw material for synthesis of the compound of the general formula () of the present invention
The compound was synthesized. The results are shown in Table 2 below.

【table】

[Table] Example 2 (Wettable powder) Compound No. 1 of the present invention, 15 parts, mixture of powdered diatomaceous earth and powdered clay (1:5), 80 parts, sodium alkylbenzenesulfonate, 2 parts, alkylnaphthalene Sodium sulfonate formalin condensate,
Three parts were ground and mixed to form a wettable powder. This is diluted with water and sprayed onto locations where pathogenic bacteria and/or their outbreaks and crop diseases occur. Example 3 (Emulsion) Compound No. 2 of the present invention, 30 parts, xylene, 55 parts, polyoxyethylene alkyl phenyl ether, 8
part, calcium alkylbenzenesulfonate, 7
Mix and stir the two parts to form an emulsion. This is diluted with water and sprayed onto pathogenic bacteria and/or locations where pathogens and/or crop diseases occur. Example 4 (Powder) 2 parts of Compound No. 3 of the present invention and 98 parts of powdered clay were pulverized and mixed to prepare a powder. This can be used as pathogens and/or
Or, sprinkle the powder on the areas where the outbreak and crop diseases occur. Example 5 (Powder) 1.5 parts of the compound No. 4 of the present invention, 0.5 parts of isopropyl hydrogen phosphate (PAP), and 98 parts of powdered clay were ground and mixed to make a powder, and a powder was prepared to investigate pathogenic bacteria and/or their occurrence, and crops. Sprinkle powder on diseased areas. Example 6 (Granules) To a mixture of 10 parts of the present compound No. 3, 30 parts of bentonite (montmorillonite), 58 parts of talc, and 2 parts of lignin sulfonate, 25 parts of water was added. , knead well and use extrusion type granulator.
Form into granules of 10 to 40 mesh and dry at 40 to 50°C to make granules. This is sprinkled on areas where pathogens and/or their outbreaks and crop diseases occur. Example 7 Preparation of test compound for foliar spray efficacy test against rice blast disease Active compound: 50 parts by weight Carrier: Mixture of diatomaceous earth and kaolin (1:5)
45 parts by weight Emulsifier: polyoxyethylene alkyl phenyl ether 5 parts by weight The above-mentioned amounts of the active compound, carrier and emulsifier are ground and mixed to form a wettable powder, which is prepared by diluting the prescribed amount with water. Test method Paddy rice (variety: Asahi) was grown in clay pots with a diameter of 12 cm, and at the 3rd to 4th leaf stage, 50 ml of a diluted solution of the test compound prepared as above at a predetermined concentration was sprayed per 3 pots. The next day, a suspension of artificially cultured rice blast fungus (Pyricularia oryzae) spores was spray inoculated (twice) and kept in a humid room at 25°C and 100% relative humidity to allow infection. Seven days after inoculation, the degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. At the same time, drug damage was also investigated. Susceptibility level lesion area ratio (%) 0 0 0.5 2 or less 1 3-5 2 6-10 3 11-20 4 21-40 5 41 or more Control value (%) = (Sorbidity of untreated area - Treatment area Morbidity/
Morbidity in untreated plot) x 100 This test is the result of 3 pots in 1 plot. The results are shown in Table 3.

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[Table] Example 8 Tomato blight control test Tomatoes grown in 9cm clay pots (variety: Awahara)
Then, the test compound in the form of an emulsion prepared according to Example 3 was sprayed using a spray gun. One day after spraying, inoculate with a spore suspension of this disease bacterium and store at 22℃ and humidity 90℃.
% or more in a constant temperature room overnight, and after 5 days, the degree of disease was graded and evaluated based on the lesion area ratio according to the following criteria, and the control value was determined. Susceptibility level lesion area ratio (%) 0 0 0.5 2 or less 1 3-5 2 6-15 3 16-30 4 31-50 5 51 or more control value (%) = (Severity of untreated area - treated area Morbidity/
Morbidity in untreated area) x 100 The results are shown in Table 4.

[Table] Example 9 Cucurbita anthracnose control test: - Test method: A test compound in the form of an emulsion prepared in accordance with Example 8 was sprayed on two-leaf stage cucumbers (variety Yotsuba) grown in a 9 cm clay pot. It was sprayed using a gun. One day after spraying, this pathogen (Colletotrichum
After inoculating the spore liquid of A. lagenarium by spray and leaving it overnight in a constant temperature room at 23°C and 90% humidity, after 6 days, the degree of disease was determined based on the lesion area percentage and the control effect was calculated in the same manner as in Example 8. did. The results are shown in Table 5.

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[Table] Example 10 Powdery mildew control test on cucumbers Test method: A test compound in the form of an emulsion prepared according to Example 3 was sprayed on two-leaf stage cucumbers (variety: Tokiwa Jizo) grown in a 9 cm clay pot. It was sprayed using a gun. One day after spraying, this pathogen (Sphaerotheca
fuliginea) was spray-inoculated and left in a constant temperature room at 23°C. After 10 days, the disease severity was determined based on the lesion area ratio in the same manner as in Example 8, and the control effect was calculated. The results are shown in Table 6.

【table】

[Table] Example 11 Efficacy test of foliar spraying against rice sesame leaf blight Paddy rice (variety: Kusabue) was grown in clay pots with a diameter of 12 cm, and preparations were made according to Example 2 at the 3rd to 4th leaf stage. 50ml of diluted solution of the test compound at the specified concentration per 3 pots.
ml was sprayed. The next day, a suspension of artificially cultured rice and sesame leaf blight fungus spores was spray inoculated (twice) and kept in a humid room at 25°C and 100% relative humidity to allow infection. 7 days after vaccination,
The degree of disease per pot was graded and evaluated according to the following criteria, and the control value (%) was determined. Morbidity level 0 No disease onset 1 Slight 2 Slight 3 Medium 4 High 5 Severe control value (%) = (Mobility level in untreated area - Morbidity level in treated area/
Morbidity in untreated plot) x 100 This test is the result of 3 pots in 1 plot. The results are shown in Table 7.

[Table] Example 12 Rice seedling sesame leaf blight control test (seed treatment) Rice seedling sesame leaf blight fungus (Helminthosporium
Seeds (variety: Koshihikari) that were naturally infected with a high rate of E. oryzae) were treated with a diluted solution of a predetermined concentration prepared in accordance with Example 2 at the concentration and method shown in the following table.
The next day, the seeds were sown in seedling boxes, and the seedlings were raised and managed in the usual manner. 15 days after sowing, all the seedlings were taken out and classified into diseased seedlings and healthy seedlings, and the control value was calculated from the ratio of healthy seedlings to the number of sown seeds using the following formula, and the results are shown in Table 8. Control value (%) = 100 - [100 - (healthy seedling rate in treatment area) / 10
0 - (Percentage of healthy seedlings in untreated area) x 100] In the table, the treatment method section indicates the following method. M-1: Soaked for 1/6 hours M-2: Soaked for 20 hours M-3: Seed dressing

[Table] Example 13 Rice Gibberella fujikuroi control test (seed treatment) Seeds (variety: Koshihikari) naturally infected with Gibberella fujikuroi were treated according to Example 2 at the concentrations and methods shown in the table below. After seed disinfection, the seeds were immersed in a diluted solution of a predetermined concentration, and after the seed sterilization treatment was completed, they were air-dried, sown in rice seedling boxes, and the seedlings were raised and managed in the usual manner, and diseased seedlings were sampled and investigated over time until 20 days after sowing. The control value (%) was calculated using the following formula, and the results are shown in Table 9. Control value (%) = 100 - diseased seedling rate in treated area / diseased seedling rate in untreated area x 100 The control value shows the average value of 3 test areas with 300 seeds per area.

【table】

[Table] Example 14 Resistant rice bakanae disease test (seed treatment) MBC-resistant Bakanae bacterium [In against benomyl
Example 13: A immersion disinfection test was conducted on infected seeds obtained by spray inoculating rice (cultivar: Koshihikari) with a vitro MIC value (minimum inhibitory concentration) of 800 ppm during the flowering stage.
It was carried out in a similar manner. The results are shown in Table 10. The control value shows the average value of 3 test plots with 300 grains per plot. Note) MBC-resistant bacteria include benomyl,
This refers to bacteria that are resistant to thisphanatemethyl and its related compounds.

[Table] The present invention described above in the detailed description section is summarized as follows. (1) General formula: In the formula, ^R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, ^R2 represents a fluoro-substituted lower alkyl group, and X represents an oxygen atom or a sulfur atom. , Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, 3, 4, 5 or 6. A carbamoylimidazole derivative represented by the following. (2) General formula: In the formula, R ² , X, Y, m and n are the same as above,
And Hal represents a halogen atom, and a compound represented by the general formula: R ¹ −NH ₂ (), where R ¹ is the same as above, is reacted, and then,
A method for producing a carbamoylimidazole derivative of the general formula (), which comprises reacting N,N'-carbonyldiimidazole. (3) An agricultural and horticultural fungicide containing the carbamoylimidazole derivative of the general formula () as an active ingredient. (4) The carbamoylimidazole derivative of the general formula () may be used alone or in the presence of a diluent (solvent and/or filler and/or carrier) and/or surfactant, and if necessary, a stabilizer, a fixing agent, and a co-agent. A crop disease control method that involves applying a mixture with a virulent agent.

Claims (1)

[Claims] 1. General formula: In the formula, ^R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, ^R2 represents a fluoro-substituted lower alkyl group, and X represents an oxygen atom or a sulfur atom. , Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, 3, 4, 5 or 6. A carbamoylimidazole derivative represented by the following. 2 formula: 1-{N-2[2,6-dichloro-4
The carbamoylimidazole derivative according to claim 1, which is -(2,2,2-trifluoroethylthio)phenoxy]ethyl-N-propylcarbamoyl}imidazole. 3 formula: 1-[N-2-(2,6-dichloro-
The carbamoylimidazole derivative according to claim 1, which is 4-trifluoromethylthiophenoxy)ethyl-N-propylcarbamoyl]imidazole. 4 formula: 1-[N-2-(2,6-dichloro-
4-Trifluoromethoxyphenoxy)ethyl-
The carbamoylimidazole derivative according to claim 1, which is N-propylcarbamoyl]imidazole. 5 General formula: In the formula, ^R2 represents a fluoro-substituted lower alkyl group, X represents an oxygen atom or a sulfur atom, Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, n represents 2, 3, 4, 5, or 6, and Hal represents a halogen atom, and a compound represented by the general formula: R ¹ -NH ₂ where R ¹ is a lower alkyl group, a lower alkoxy-lower alkyl group, or a carbon A compound represented by 3 to 8 cycloalkyl groups is reacted, and then N,
General formula characterized by reacting N′-carbonyldiimidazole: A method for producing a carbamoylimidazole derivative represented by the following formula, wherein R ¹ , R ² , X, Y, m and n have the same meanings as above. 6 General formula: In the formula, ^R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, ^R2 represents a fluoro-substituted lower alkyl group, and X represents an oxygen atom or a sulfur atom. , Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, 3, 4, 5 or 6. Horticultural fungicide.