JPH0442376B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a novel N-benzyl-cyclopropane carboxamide derivative, a method for producing the same, and a fungicide for agricultural and horticultural use. More specifically, the present invention relates to an N-benzyl-cyclopropane carboxamide derivative represented by the following formula (1). General formula: In the formula, X represents a halogen atom, n represents 1 or 2, ^R1 represents a hydrogen atom or a halogen atom, ^R2 represents a lower alkyl group or a halogen-substituted lower alkyl group, where ^R When is a hydrogen atom, R ² represents a halogen-substituted lower alkyl group, when R ¹ is a halogen atom, R ² represents a lower alkyl group, and R ³ represents a lower alkyl group. The compound of the above general formula () can be produced, for example, by the following method, and the present invention also relates to this production method. Manufacturing method (): - General formula: In the formula, X and n are the same as above, and a compound represented by the general formula: N-benzyl- of the general formula (), characterized in that it is reacted with a compound represented by: where R ¹ , R ² and R ³ are the same as above, and A represents a hydroxyl group or a halogen atom. A method for producing a cyclopropane carboxamide derivative. The present invention also relates to an agricultural and horticultural fungicide containing the N-benzyl-cyclopropane carboxamide derivative of the general formula () as an active ingredient. Japanese Unexamined Patent Application Publication No. 1983-1979, which is a publication known before the filing date of the present application.
In the specification of Publication No. 66555, the general formula: (In the formula, R ₁ represents a hydrogen atom or a lower alkyl group, R ₂ represents an alkyl group or a cycloalkyl group, and R ₁ and R ₂ may form a ring.) - It is stated that the acetamide derivative has herbicidal activity, and the specification includes, for example, the formula A compound represented by is described. However, the above-mentioned general formula (A) does not include the compound of the above-mentioned general formula () specified in the present invention, and furthermore, there is no description of any sterilizing use. Similarly, Japanese Patent Application Laid-Open No. 58-26847, which was publicly known before the filing date of the present application,
The specification of the publication contains the general formula: (In the formula, R ₁ is an α-branched alkyl group, R ₂ is a hydrogen atom, a lower alkyl group or a lower alkenyl group, or R ₁ and R ₂ are an alkylene group, and X is a halogen atom or a lower alkyl group. , a lower alkoxyl group, a cyano group, or a nitro group, and n represents an integer of 1 to 3). For example, the book contains A compound represented by is described. However, the above general formula (B) does not include the compound of the above general formula () specified in the present invention. The present inventors have carried out synthesis and biological activity screening in order to create novel compounds with biological activity. As a result, we succeeded in synthesizing a novel N-benzyl-cyclopropane carboxamide derivative of the general formula (), and further discovered that this compound has, for example, excellent fungicidal activity for agricultural and horticultural purposes. According to the research conducted by the present inventors, the N-benzyl-cyclopropane carboxamide derivative of the general formula () of the present invention is a novel compound that has not been described in any publications known before the filing date of the present application. It was also found that the compound of formula () of the present invention exhibits excellent control efficacy suitable for the purpose of controlling plant diseases, and in particular, exhibits optimal and excellent efficacy for controlling rice blast disease. Such pesticidal efficacy is significantly superior to that of known compounds having similar chemical structures, such as the compounds of formula (A-1) and formula (B-1) described in the above-mentioned known literature. It was found that it brings about The superior biological activity of the compounds of the present invention is due to the correlation with the chemical structure of the compounds. That is, the structural characteristics of the compound of the present invention are that a halogen-substituted -α-methylbenzyl group is bonded to the nitrogen atom in the acid amide bond, and a substituted cyclopropyl group is bonded to the carbon atom of the carbonyl group as shown in the general formula (). It is at the point where the groups are bonded. In the substituted cyclopropyl group, the combination of R ¹ and R ² as specified in the general formula (), that is, when R ¹ is a hydrogen atom, R ²
is a halogen-substituted lower alkyl group, and
When R ¹ is a halogen atom, R ² is a lower alkyl group. General formula () of the present invention having the above structural features
It has been discovered that the compound exhibits extremely significant bactericidal effects that are not observed in other related compounds. The plant disease control activity of the compound of the present invention also exhibits a more significant effect in terms of its residual effect. For example, especially when controlling rice blast disease,
In relation to the fact that rice blast is the most important disease for control in rice cultivation, the residual effectiveness of the control agent is the most important factor due to the relationship between the appropriate time for treatment of the agent and the time of outbreak of rice blast. The practical value of a compound is determined by its residual effect.
The compound of the present invention was found to be an excellent biologically active compound that also satisfies these requirements. The compound of the general formula (), which is an intermediate for the production of the compound of the general formula () of the present invention, is a novel compound that has not been described in any known literature prior to the filing date of the present application. As described above, this compound is highly useful industrially as an intermediate of the general formula () of the present invention, which is useful for controlling various agricultural and horticultural diseases. Therefore, an object of the present invention is to provide an N-benzyl-cyclopropane carboxamide 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 can be safely used without causing phytotoxicity to plants, and exhibits excellent control efficacy against a wide range of plant diseases in addition to the rice blast disease, and has excellent residual efficacy. Since it also has the same characteristics, it can be advantageously and conveniently applied to control a wide range of plant diseases. The bactericidal spectrum of the compounds of the present invention includes, for example, archaeal fungi (Archimycetes), algal fungi (Phycomycetes), ascomycetes (Ascomycetes), basidiomycetes (Basidiomycetes), incomplete It can be effectively used against various plant diseases caused by fungi (Fungi Imperfecti) and other bacteria. Representative examples of the fungicidal spectrum of the compounds of the present invention include, for example, rice blast disease (Pyricularia oryzae),
Anthracnosis of cucurbits (Colletotrichum lagenarium)
etc., but the bactericidal spectrum should not be limited to these. The N-benzyl-cyclopropane carboxamide derivative of the general formula () of the present invention can be prepared, for example, by the following method. It can be easily manufactured. Manufacturing method (): (In the formula, X, n, R ¹ , R ² , R ³ and A are the same as above.) In the above reaction formula, 2, R ¹ is a hydrogen atom or
It represents a halogen atom similar to the above examples, and R ² is a lower alkyl group such as methyl, ethyl, propyl, isoprolyl, n-(iso-, sec-, or tert-)butyl, or the same as the above examples. A lower alkyl group substituted with a halogen atom such as those exemplified above, such as mono-(di- or tri)chloromethyl, mono(di- or tri)fluoromethyl, mono(di- or tri)bromomethyl, 1
-(or 2-)chloro(promo, or fluoro)
Ethyl, 1,1-(1,2 or 2,2)di-chloro(bromo or fluoro)ethyl, 1,1,1-
(1,1,2-, 1,2,2- or 2,2,2-)
Indicates trichloro(bromo or fluoro)ethyl, etc. However, if R ¹ here represents a hydrogen atom, R ²
represents a halogen-substituted lower alkyl group, and
When R ¹ represents a halogen atom, R ² represents a lower alkyl group. A represents a hydroxyl group or a halogen atom as exemplified above. In the process for producing the compound of the general formula () of the present invention shown in the above reaction formula, specific examples of the compound of the general formula () as a raw material include, for example, 4-chloro-
Examples include α-methylbenzylamine, 4-bromo-α-methylbenzylamine, 2-chloro-α-methylbenzylamine, and 3,4-dichloro-α-methylbenzylamine. Similarly, specific examples of compounds of general formula () which are raw materials include 2,2-dichloro-(trans)-3-chloromethyl-(cis)-3-methylcyclopropanecarboxylic acid, 1,2, 2-Trichloro-3,3-dimethylcyclopropanecarboxylic acid, 1,2,2-trichloro-3,3-diethylcyclopropanecarboxylic acid, 2,2-dichloro-
(trans)-3-bromomethyl-(cis)-3-methylcyclopropanecarboxylic acid, 2,2-dichloro-(trans)-3-trifluoromethyl-(cis)
-3-Methylcyclopropanecarboxylic acid, 1-bromo-2,2-dichloro-3,3-dimethylcyclopropanecarboxylic acid, 2,2-dichloro-1-
Fluoro-3,3-dimethylcyclopropanecarboxylic acid, 2,2-dichloro-(trans)-3-
(2,2,2-trifluoroethyl)-(cis)-3
-Methylcyclopropanecarboxylic acid, 2,2-dichloro-(trans)-3-(2-chloroethyl)-
(cis)-3-methylcyclopropanecarboxylic acid and the like can be exemplified. Furthermore, instead of the above-mentioned carboxylic acids, their acid halides, such as acid chlorides and acid bromides, can be exemplified. Next, the above manufacturing method will be specifically explained using representative examples. The above manufacturing method can be carried out desirably using a solvent or a diluent. All inert solvents and diluents can be used for this purpose. Examples of such solvents or diluents include water; aliphatic, cycloaliphatic and aromatic hydrocarbons (optionally 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, diiso-propyl ether, diptyl ether, propylene oxide, dioxane, tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, methyl-iso-propyl ketone, methyl-iso-butyl ketone; = tolyles such as acetonitrile,
Propioniloryl, acritonitrile; 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 dimethylsulfoxide, sulfolane; and bases such as pyridine. The reaction of the invention can also 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. . In addition, in the above method, when a carboxylic acid is used as a raw material of the general formula (), a dehydration condensation agent can be used, examples of which include N,
An example is N'-dicyclohexylcarbodiimide. The method of the invention can be carried out within a wide temperature range. It can generally be carried out between about -20°C and the boiling point of the mixture, preferably between about 0 and about 100°C.
Can be carried out between ℃. 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. Further, the compound of general formula () can be easily produced, for example, by the following method. Manufacturing method (): − [In the formula, (R ² )′ represents a halogen-substituted lower alkyl group, and Hal ¹ represents a halogen atom. ] Manufacturing method ()-: (In the formula, R ² , R ³ and Hal ¹ are the same as above, and Hal ² represents a halogen atom.) Specific examples of the compound of general formula () which is the starting material in the above production method () include 2,2 -dichloro-(trans)-3-chloromethyl-(cis)-
3-methylcyclopropane methanol, 2,2-
dichloro-(trans)-3-bromomethyl-(cis)-3-methylcyclopropane methanol, 2,
2-dichloro-(trans)-3-trifluoromethyl-(cis)-3-methylcyclopropane methanol, 2,2-dichloro-(trans)-3-(2,
2,2-trifluoroethyl)-(cis)-3-methylcyclopropane methanol, 2,2-dichloro-(trans)-3-(2-chloroethyl)-(cis)-3-methylcyclopropane methanol, etc. I can give an example. Further, specific examples of the compound of general formula () which is the starting material in the above production method () include methyl 2-chloro-crotonate, methyl 2-promocrotonate, methyl 2-fluorocrotonate, methyl 2-chloro-crotonate, Examples include methyl chloro-3-ethyl-2-pentenoate. Further, other alkyl esters can be used instead of the methyl ester represented by the general formula (). In the production method (), instead of sodium trichloroacetate which reacts with the compound of general formula (),
For example, a phase transfer catalyst such as 50% sodium hydroxide and triethylbenzylammonium chloride in chloroform can be reacted. Typical examples are shown below, and the above manufacturing methods () and ()
will be explained respectively. In order to carry out the above method, the above manufacturing method ()
Using the same inert solvent or diluent as above, the desired product can be obtained with high purity and high yield. It can also be carried out within a wide temperature range, for example between about -20°C and the boiling point of the mixture, desirably between about 0 and about 100°C. Although it is preferable to carry out the operation under normal pressure, it is also possible to operate under increased pressure or reduced pressure. When the compound of formula () of the present invention is used as a fungicide for agriculture and horticulture, it can be used as is by diluting it directly with water, or it can be used as is, as is generally done in the agricultural chemical manufacturing field, by using an agricultural chemical adjuvant. Depending on the method, it can be used in various formulation forms. In actual use, these various formulations 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 glycol]; 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 can be mentioned. Extending agents or carriers include, for example, slaked lime, magnesium lime, gypsum, calcium carbonate,
Inorganic granules such as silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. pyrophyllite, talc, montmorinite, beidellite, vermiculite, kaolinite, mica), etc. For example, vegetable powder such as shell powder, starch, modified starch, sugar, glucose, crushed plant stems, etc.; For example, synthetic resin powder such as phenolic resin, urea resin, vinyl chloride resin, etc.; can be mentioned. Examples of the surfactant include anionic surfactants such as alkyl sulfate esters (e.g., sodium lauryl sulfate), aryl sulfonic 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.
Sulfite, zinc powder, dicyandiamide]: Oxygen supply agent [e.g. chlorate]: Efficacy extender: Dispersion stabilizer [e.g. casein, tragacanth, carboxymethylcellulose (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 the active ingredient in about
0.1 to about 95% by weight, preferably about 0.5 to about 90% by weight
It can contain. 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 compound of the present invention may also be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators, attractants [e.g. Monophosphoric acid ester compounds, carbamate compounds, diothi (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds, triazines compound] or/and fertilizer etc. may also be present. 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 (e.g., spraying, misting, atomizing, dusting, granulation, water surface application, and pouring): Fumigation: soil application (e.g., mixing, sprinkling, vaporing, irrigation); surface application (e.g., spreading, banding, dressing, coating): application by dipping, etc. I can do it. 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, for example, about 0.03 to about 10 kg, preferably about 0.3 to about 6 kg of active compound per hectare. However, in special cases, exceeding these ranges may be
or lower is possible, and sometimes 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 (Intermediate synthesis) 2,2-ziruro-(trans)-3-chloromethyl-(cis)-3-methylcyclopropane methanol (8 g) was added to a mixed solvent of acetic acid (30 ml) and water (6 ml). Suspend and add sodium bromite hydrate (approximately 60% sodium bromite content) (16 g) at room temperature. After the addition, the reaction temperature is raised to 40°C.
After a total reaction time of 8 hours, the reaction mixture was poured into ice water;
After adjusting the pH to 5 with dilute hydrochloric acid, extract with ether. The ether layer is washed with aqueous hypo solution and dried over anhydrous sodium sulfate. The ether is distilled off under reduced pressure and the residue is recrystallized from hexane to obtain the desired 2,2-dichloro(trans) represented by the following formula.
-3-chloromethyl-(cis)-3-methylcyclopropanecarboxylic acid (3.2 g) is obtained.
mp.118~120℃ (Compound No.-1) Example 2 (Intermediate synthesis) Compound No.-1 (3.0
g) with thionyl chloride (1.0 ml) at 60°C. The reaction mixture was distilled under reduced pressure to obtain the desired 2,2-dichloro-(trans)-3-chloromethyl-(cis)-3-methylcyclopropanecarboxylic acid chloride (2.8 g) represented by the following formula.
is obtained. bp.105～10℃/20mmHg (Compound No.-2) Example 3 (Intermediate Synthesis) Compounds of the general formula () of the present invention shown in Table 1 below were synthesized by the same method as in Examples 1 and 2 above.

【table】

[Table] Example 4 (Intermediate synthesis) Methyl 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylate (10 g) was dissolved in formic acid (20 ml), and concentrated sulfuric acid (0.1 g) was added. The mixture is heated gently to reflux for 12 hours. After cooling, add water (60 ml) to the thread and collect the precipitated crystals. When this crystal is recrystallized from hexane, the desired 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylic acid (3.4 g) represented by the following formula is obtained. mp.148~150℃ (Compound No.-11) 1, 2, used as a raw material in Example 4 above,
A reference example of the synthesis of methyl 2-trichloro-3,3-dimethylcyclopropanecarboxylate is shown below. Synthesis reference example To methyl 2-chloro-3-methyl-2-butenoate (15.5g), sodium trichloroacetate (55g)
is added over 5 hours at 100-120°C. After addition,
Stirring is continued at the same temperature for an additional 2 hours. After cooling,
The reaction mixture is extracted with ether, and the ether layer is washed with water and dried over anhydrous sodium sulfate. After distilling off the ether under reduced pressure, the residue is distilled under reduced pressure to obtain the desired 1,2,2-trichloro-
Methyl 3,3-dimethylcyclopropanecarboxylate (10.3 g) is obtained. bp.156～159℃/23mm
Hg Example 5 (Intermediate synthesis) 1,2,2-triclo-2,2-dimethylcyclopropanecarboxylic acid (3.0 g) synthesized in Example 4 above and thionyl chloride (1.0 ml) were mixed and heated at 60°C. React with. The reaction mixture was distilled under reduced pressure to obtain the desired 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylic acid chloride (2.8 g) represented by the following formula. bp.100
℃／20mmHg (Compound No.-12) Example 6 (Intermediate synthesis) The results are shown in Table 2 below using the same method as in Examples 4 and 5 above. A compound of the general formula () of the present invention was synthesized.

【table】

[Table] Example 7 [General formula () synthesis example] 4-chloro-α-methylbenzylamine (15.6
g), triethylamine (10.1 g) was dissolved in toluene (150 ml), and while stirring, 0 to 10
1,2,2-trichloro-3,3-dimethylcyclopropanecarboxylic acid chloride (23.6 g) at °C.
Add dropwise a solution of toluene (30 ml). After the dropwise addition was completed, the mixture was stirred at room temperature for 2 hours. Pour the reaction solution into ice water, and extract the aqueous layer with toluene. The toluene layers are combined, washed sequentially with 1% aqueous hydrochloric acid, 1% aqueous sodium hydroxide, and water, and dried over anhydrous sodium sulfate. When toluene is distilled off under reduced pressure, the desired colorless crystals N-(4-chloro-
α-methylbenzyl)1,2,2-trichloro-
3,3-dimethylcyclopropanecarboxamide (32 g) is obtained. mp.138~139℃ (Compound No. 1) Example 8 The compounds of the present invention synthesized according to the same method as above are shown in Table 3 below.

[Table] Example 9 (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 Three parts of sodium sulfonate formalin condensate were ground and mixed to prepare a wettable powder. This is diluted with water and sprayed onto locations where pathogens and/or their outbreaks and crop diseases occur. Example 10 (Emulsion) Compound No. 1 of the present invention, 30 parts, xylene, 55 parts, polyoxyethylene alkyl phenyl ether, 8
part, alkylbenzenesulfone part calcium, 7
Mix and stir 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 11 (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 12 (Powder) 1.5 parts of Compound No. 1 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 13 (Powder) To a mixture of 10 parts of the present compound No. 7, 30 parts of bentonite (montmorillonite), 58 parts of talc, and 2 parts of lignin sulfonate, 25 parts of water was added, After kneading well, using an 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 14 (Granule) 95 parts of clay mineral particles having a particle size distribution of 0.2 to 2 mm were placed in a rotary mixer, and while rotating, 5 parts of Compound No. 1 of the present invention dissolved in an organic solvent was sprayed evenly. After soaking, dry at 40-50℃ to form granules. This is sprinkled on areas where pathogens and/or their outbreaks and crop diseases occur. Example 15 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 A wettable powder is prepared by grinding and mixing the above-mentioned amounts of the active compound, carrier and emulsifier, and diluting the prescribed amount with water. Test method Paddy rice (variety: Asahi) was cultivated in clay pots with a diameter of 12 cm, and during the 3rd to 4th period, 50 ml of a diluted solution of the test compound at a predetermined concentration prepared as above was sprayed per 3 pots.
The next day, a suspension of artificially cultured rice blast fungus 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. Morbidity Spot area percentage 0 0 0.5 2 or less 1 3 to 5 2 6 to 10 3 11 to 20 4 21 to 40 5 41 or more control value (%) = (morbidity in untreated area - morbidity 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 4.

[Table] Through the same test as in Example 15 above, it was confirmed that compounds of the present invention other than those exemplified above also exhibited similar effects. Example 16 Test method for residual effect test against rice blast Paddy rice (variety: Asahi) was grown in clay pots with a diameter of 12 cm, and at the 3rd to 4th leaf stage, a test compound prepared in the same manner as in Example 15 was applied. 50 ml of the diluted solution at a predetermined concentration was sprayed per three pots. Five days after spraying, a suspension of artificially cultured rice blast fungus spores was spray inoculated (twice), and 25
The animals were kept in a humid room at 100% relative humidity and infected.
Seven days after inoculation, the degree of disease per pot was graded and evaluated in the same manner as in Example 15, and the control value (%) was determined. The results are shown in Table 5.

[Table] Through the same test as in Example 16 above, it was confirmed that, for example, Compound No. 10 also exhibited excellent residual efficacy. Example 17 Test method for controlling anthracnose disease in cucumber Cucumber cultivated in a 9 cm clay pot (variety: Yotsuba)
Then, 25 ml of a diluted solution of the test compound in the form of an emulsion prepared at a predetermined concentration was sprayed into each of three pots according to the example.
One day after spraying, the spore liquid of this pathogen was spray inoculated and 23
It was kept in a constant temperature room at 90% humidity or higher for one day. After 6 days of standing, the disease severity was graded and evaluated based on the lesion area ratio according to the following criteria, and the control value (%) was determined. Morbidity Spot area percentage (%) 0 0 0.5 2 or less 1 3-5 2 6-15 3 16-30 4 31-50 5 Control value of 51 or more (%) = (Mobility of untreated area - treated area Morbidity/
Morbidity in untreated area) x 100 The results are shown in Table 6.

【table】

Claims (1)

[Claims] 1. General formula: In the formula, X represents a halogen atom, n represents 1 or 2, R ¹ represents a hydrogen atom or a halogen atom, and R ²
represents a lower alkyl group or a halogen-substituted lower alkyl group, where R ¹ is a hydrogen atom, R ² represents a halogen-substituted lower alkyl group, and when R ¹ is a halogen atom, R ² is a lower alkyl group. and ^R3 represents a lower alkyl group. 2 formula: N-4 described in claim 1 expressed as
-Chloro-α-methylbenzyl 1,2,2-trichloro-3,3-dimethylcyclopropanecarboxamide. 3 formula: N-4 described in claim 1 expressed as
-chloro-α-methylbenzyl2,2-dichloro-(trans)-3-chloromethyl-(cis)-3-
Methylcyclopropanecarboxamide. 4 General formula: In the formula, X is a halogen atom, and n represents 1 or 2, and a compound represented by the general formula: In the formula, R ¹ represents a hydrogen atom or a halogen atom, R ² represents a lower alkyl group or a halogen-substituted lower alkyl group, where when R ¹ is a hydrogen atom, R ² represents a halogen-substituted lower alkyl group. , R ¹ is a halogen atom, R ² is a lower alkyl group, R ³ is a lower alkyl group, and A is a hydroxyl group or a halogen atom. The general formula is: A method for producing an N-benzyl-cyclopropane carboxamide derivative represented by the following formula, where X, n, R ¹ , R ² and R ³ are the same as above. 5 General formula: In the formula, X represents a halogen atom, n represents 1 or 2, ^R1 represents a hydrogen atom or a halogen atom, ^R2 represents a lower alkyl group or a halogen-substituted lower alkyl group, where ^R is a hydrogen atom, R ² represents a halogen-substituted lower alkyl group, when R ¹ is a halogen atom, R ² represents a lower alkyl group, and R ³ represents a lower alkyl group. An agricultural and horticultural fungicide containing a benzyl-cyclopropane carboxamide derivative as an active ingredient.