JPH089601B2 - N-Indanylcarboxylic acid amide derivative and agricultural and horticultural fungicide containing the same - Google Patents

Description

TECHNICAL FIELD The present invention relates to an N-indanylcarboxylic acid amide derivative and an agricultural and horticultural fungicide containing the N-indanylcarboxylic acid amide derivative as an active ingredient.

[Problems to be Solved by Prior Art and Invention]

Conventionally, it is known that certain carboxylic acid amide derivatives have biological activity such as a bactericidal effect. For example, It has been confirmed that such compounds have bactericidal activity.
However, these compounds are not always sufficiently effective as agricultural and horticultural fungicides, as is clear from the test examples described below.

Benomyl [methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate] and thiophanate methyl [1,2-bis (3-methoxycarbonyl-2-
Thioimidazole) benzene] and other benzimidazoles
The thiophanate fungicides have excellent control effects against various pathogenic fungi parasitic on agricultural and horticultural crops, and have been widely used as agricultural and horticultural fungicides since the 1970s. However, pathogenic bacteria resistant to these fungicides (hereinafter referred to as drug-resistant bacteria) have become widespread, and a situation has arisen in which they cannot be practically used.

Procymidone [N- (3,5-dichlorophenyl) -1,2
-Ditylcyclopropane-1,2-dicarboximide]
Cyclic imide fungicides such as these have been widely used in place of this because they showed activity against such drug-resistant Botrytis cinerea, but in recent years, pathogens that are also resistant to such cyclic imide fungicides It has become widespread, and in fact, there are often situations in which it cannot be used.

The N-phenylcarbamate compounds described in JP-A-58-126856 and the like are reported to exhibit high activity against such resistant bacteria. However, since the N-phenylcarbamate compound has no effect on drug-susceptible bacteria, it may not be used alone.

[Means for solving problems]

As a result of intensive investigations by the present inventors in view of the above problems,
A compound having a strong bactericidal effect against both drug-sensitive bacteria and drug-resistant bacteria has been found, and the present invention has been completed.

That is, the gist of the present invention is the following general formula (I) [In the above formula, A is a group, Represents

[In the group, X represents a halogen atom, a methyl group or a trifluoromethyl group, and Y represents a hydrogen atom, a halogen atom other than a chlorine atom, a lower alkyl group other than a methyl group, a mercapto group or a lower alkylthio group. ) R represents a lower alkyl group, and n- represents an integer of 1 to 6. ] It exists in the N-indanyl carboxylic acid amide derivative shown by these, and the fungicide for agriculture and horticulture which uses this as an active ingredient.

 Hereinafter, the present invention will be described in detail.

 The compound of the present invention is represented by the general formula (I) shown above.

In formula (I), A is a group, And preferably Is.

In the group, X is a halogen atom, a methyl group or a trifluoromethyl group, and Y is a hydrogen atom, a halogen atom other than a chlorine atom, a lower alkyl group other than a methyl group, a mercapto group or a lower alkylthio group. Y is preferably a hydrogen atom or a lower alkyl group, and particularly preferably a hydrogen atom or a lower alkyl group.

In the formula (I), R is a lower alkyl group, preferably a C ₁ -C ₃ lower alkyl group, and a methyl group is particularly preferable. n is an integer of 1 to 6, preferably 1 to 4
Is an integer. When n is an integer of 2 to 6, Rs in the formula (I) may be the same or different from each other. The one in which R is substituted at the 3-position of the indane skeleton is particularly preferable because it shows effective activity against Botrytis cinerea.

Specific examples of the compound of the present invention represented by formula (I) include those shown in Table-1 to Table-3.
The compounds of the present invention are not limited to these.

The compounds of the present invention are all novel compounds and are produced, for example, according to the following reaction formula.

(In the above reaction formula, A, R and n have the same meanings as those of the general formula (I) shown above.) The above reaction is carried out by the thiazole-5 represented by the general formula (II).
A carboxylic acid or a reactive derivative thereof and a compound represented by the general formula (II
It is carried out by reacting with the aminoindane derivative represented by I) in the presence or absence of a solvent inert to the reaction.

The thiazole-5-carboxylic acid represented by the general formula (II) or a reactive derivative thereof used in the reaction is 0.5 to 0.5 with respect to the aminoindane derivative represented by the general formula (III).
It is used in the range of 1.5 equivalents, preferably 0.9 to 1.1 equivalents. This reaction can be carried out in the temperature range of -70 ° C to the boiling point of the solvent used, preferably -40 ° C to the boiling point of the solvent.

Examples of carboxylic acids represented by the general formula (II) or reactive derivatives thereof include reactive carboxylic acids, acid anhydrides, acid halides such as salt oxides, and carboxylic acid esters.

Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene; halogenated hydrocarbons such as carbon tetrachloride and chloroform; aromatic halogenated hydrocarbons such as chlorobenzene; diethyl ether, tetrahydrofuran. , Ethers such as dioxane; ester such as ethyl acetate; polar solvents such as dimethyl sulfoxide, dimethylformamide, water and the like.

In order to allow this reaction to proceed smoothly, an appropriate reaction aid can be used depending on the kind of the carboxylic acid represented by the general formula (II) or the reactive derivative thereof.

Examples of the reaction aid include a dehydrating agent such as ethoxyacetylene, dicyclohexylcarbodiimide and phosphorus pentoxide when using carvone as (II), and N-methylmorpholine or triethylamine such as N-methylmorpholine when using an acid anhydride. Tertiary amines such as: pyridine, picoline, N, N-
An aromatic base such as diethylaniline, a tertiary amine such as triethylamine when an acid halide is used; an aromatic base such as pyridine or picoline; an alkali metal water such as sodium hydroxide or potassium hydroxide. Oxides; alkali metal hydrides such as sodium hydride;
Alternatively, alkali metal alcoholates such as sodium ethylate, and when carboxylic acid esters are used, alkali metal alcoholates such as sodium ethylate can be used.

These reaction auxiliaries can be used generally in 0.01 to 2.0 equivalents, preferably 0.9 to 1.1 equivalents, relative to the aminoindane derivative represented by the general formula (II).

The compound of the present invention can be optionally produced by using the rearrangement reaction described below.

(In the above reaction formula, A, R, and n have the same meanings as those of the general formula (I) shown above.) In the above reaction, the acyltetrahydroquinoline derivative represented by the general formula (IV) is added in the presence of an acid catalyst at -40 ° C to 200 ° C
It is preferably carried out by rearrangement at 0 ° C to 150 ° C.

Examples of the acid catalyst include sulfuric acid, phosphoric acid, polyphosphoric acid, Lewis acid and the like, and the amount thereof can be used from 0.001 equivalent to a large excess with respect to the acyltetrahydroquinoline derivative.

In some cases, the compound of the present invention can be produced according to the following reaction scheme.

(In the above reaction formula, X, Y, R and n have the same meanings as described above.) In the above reaction, the thioamide derivative or thiourea derivative represented by the general formula (V) and the chloroacetamide derivative represented by the general formula (VI) And are reacted in the presence of a solvent inert to the reaction.

The thioamide derivative or thiourea derivative represented by the general formula (V) used in the reaction is used in the range of 0.5 to 1.5 equivalents, preferably 0.9 to 1.2 equivalents, relative to the chloroacetamide derivative represented by the general formula (VI). . This reaction is from -70 ° C to the boiling point of the solvent used, preferably -40 ° C.
To the boiling point of the solvent.

Examples of the solvent used in the reaction include aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether and tetrahydrofuran; polar solvents such as dimethyl sulfoxide, dimethylformamide and water; alcohols such as methanol and ethanol; Nitriles such as acetonitrile; ketones such as acetone and methyl ethyl ketone; and the like.

The compounds of the present invention thus obtained are all novel and have excellent bactericidal activity. In particular, it has an excellent control power against disease fungi of various plants and is useful as an agricultural and horticultural fungicide.

In using the compound of the present invention as an agricultural and horticultural fungicide, this compound may be used as it is, in order to effectively disperse the active ingredient in the application scene, an auxiliary agent is added according to a conventional method, It is preferably used in the form of emulsion, wettable powder, powder and the like.

Examples of the solvent that is one of the auxiliary agents in the agricultural and horticultural germicide of the present invention include water, alcohols (methyl alcohol, ethyl alcohol, ethylene glycol, etc.), kents (ascent, methyl ethyl ketone, cyclohexanone, etc.), ethers ( Ethyl ether, dioxane, cellosolves, etc.), aliphatic hydrocarbons (kerosene, kerosene,
Fuel oil, etc., aromatic hydrocarbons (benzene, toluene,
Xylene, solvent naphtha, methylnaphthalene, etc.),
Halogenated hydrocarbons (dichloroethane, trichlorobenzene, carbon tetrachloride, etc.), acid amides (dimethylformamic acid), esters (ethyl acetate, butyl acetate, glycerin esters of fatty acids, etc.), nitriles (acetonitrile, etc.), etc. Suitably, one or a mixture of two or more thereof is used.

Further, as the extender, clays such as kaolin and bentonite, talc such as talc and pyrophyllite, diatomaceous earth, mineral powders such as oxides of white carbon and soybean powder, plants such as carboxymethylcellulose (CMC) Suitable are powdery powders and the like, and one kind or a mixture of two or more kinds thereof is used.

Moreover, you may use surfactant as a spreading agent, a dispersing agent, an emulsifier, and a penetrating agent. Examples of the surfactant include nonionic surfactants (polyoxyethylene alkylallyl ether, polyoxyethylene sorbitan monolaurate, etc.), cationic surfactants (alkyldimethylbenzyl ammonium chloride, alkylpyridinium chloride, etc.), Examples include anionic surfactants (alkylbenzene sulfonate, lignin sulfonate, higher alcohol sulfate), amphoteric surfactants (alkyl dimethyl betaine, dodecylaminoethylglycine, etc.).

These surfactants are used as one kind or as a mixture of two or more kinds depending on the application.

In applying the agricultural and horticultural fungicide of the present invention, when used in the form of an emulsion, the compound of the present invention 10 to 50 parts, the solvent 10 to
A mixture of 80 parts and 3 to 20 parts of a surfactant in an appropriate ratio is used as a stock solution, which is diluted with water to a predetermined concentration before use and applied by a method such as spraying.

When used in the form of a wettable powder, the compound of the present invention 5
-80 parts and 10-90 parts of the extender and 1-20 parts of the surfactant are mixed in an appropriate ratio, and the mixture is diluted with water or the like as in the case of the emulsion and used.

When used in the form of a powder, the compound of the present invention is usually mixed uniformly with 95 to 99 parts by weight of a bulking agent such as kaolin, bentonite or talc.

The agricultural and horticultural fungicide of the present invention can also be used as a mixture with other active ingredients that do not inhibit the fungicidal effect of the present active ingredient, such as fungicides, insecticides and acaricides.

The method of applying the agricultural and horticultural fungicide of the present invention can be suitably applied to both foliar application and water surface application. In the case of foliar application, the emulsion or wettable powder is usually diluted with water so as to contain 10 to 1000 ppm, and 10 to 500 liters may be applied per 10 ares.

〔The invention's effect〕

The compounds of the present invention are all novel and have excellent bactericidal activity. For example, rice wilt disease (Rhizoctonia Solan
i), various rust diseases of wheat (Puccinia recondita), snow rot disease (Typhula incarnate, T.ishikariensis), leaf rot of grass and grass (Rhizoctonia solani), gray mold of various crops (Botrytis cinerea), Rice blast (Pyriculari)
a oryzae) and powdery mildew of various crops (Erysiphe gramini
s) and fungal diseases of various crops (Sclerotinia sclerotiorum)
It has a strong bactericidal effect against. Among them, for gray mold, even for bacteria susceptible to Bayesimidazole / thiophanate fungicides and cyclic imide fungicides,
It also has extremely high activity against resistant bacteria,
It is useful as a fungicide for agriculture and horticulture.

Further, the compound of the present invention, even though it has systemic permeability, has almost no harmful effect on plants, and has low toxicity to human livestock or fish.
It is extremely useful for controlling plant diseases.

〔Example〕

Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples unless it exceeds the gist.

In the above, "part" means "part by weight". The structures of the compounds of the present invention synthesized in Production Examples were confirmed by elemental analysis, 1R spectrum, NMR spectrum and the like.

Production Example 1 Synthesis of 2-amino-N- (1,1-dimethylindan-4-yl) -4-methylthiazol-5-carboxamide 2-aceto-2 in a solution of 0.45 g (5.9 mmol) of thiourea in 10 ml of water. A solution of 0.95 g (3.4 mmol) of -chloro-N- (1,1-dimethylindan-4-yl) acetamide in 10 ml of ethanol was added, and the mixture was refluxed for 2 hours. After allowing to cool, 5N sodium hydride aqueous solution was added to the reaction solution to make it alkaline, and the precipitated crude crystals were taken. The obtained crude crystals were recrystallized with ether to give 0.95 g of pale yellow crystals (compound N shown in Table 4).
o.1) was obtained. The yield was 93%.

2-aceto-2-chloro-N- (1,1,3-
Inventive compound No. 3 shown in Table 4 was produced in the same manner except that trimethylindan-4-yl) acetamide was used.

Production Example 2 2,4-Dimethyl-N- (1,1,3-trimethylindane-
Synthesis of 4-yl) thiazol-5-carboxamide 2-aceto-2-chloro-N- (1,1,3-trimethylindan-4-yl) acetamide 1.02 g (3.5 mmol) in benzene 50 ml solution thioacetamide 0.32 g (4.3 mmol) was added, and the mixture was heated under reflux for 1.5 hours. After allowing to cool, the reaction solution was washed with a saturated aqueous solution of water, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (eluting solvent: ethyl acetate / hexane = 1/2) to give white crystals (1.05 g, compound No. shown in Table 4).
2; mp117-118 ° C) was obtained. The yield was 96%.

Inventive compound No. 5 shown in Table 4 was produced in the same manner except that the raw materials were changed.

Production Example 3 4-Methyl-N- (1,1,3-trimethylindane-4
-Yl) Synthesis of thiazole-5-carboxamide 4-methyl-5-thiazolecarboxylic acid 1.7 g (10.3 mm
10 ml of thionyl chloride was added to (ol) and the mixture was heated under reflux for 1 hour. Excess thionyl chloride was distilled off under reduced pressure, and the residue was mixed with 10 ml of ethyl acetate.
Dissolved in. 1.8 g (10.3 mmol) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine were added to this solution.
Was added to a 10 ml solution of ethyl acetate and stirred at room temperature for 3 hours.
The reaction solution was washed successively with water, aqueous sodium hydrogen carbonate solution, water and saturated brine. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1 /
Separation and purification in 2) gave 1.6 g of amorphous solid (Compound No. 6 shown in Table 4). The yield was 50.2%.

Inventive compounds No. 4 and No. 9 shown in Table 4 were produced in the same manner except that the raw materials were changed.

Production Example 4 Synthesis of 2-mercapto-4-methyl-N- (1,1,3-trimethylindan-4-yl) thiazol-5-carboxamide 2-aceto-2-chloro-N- (1,1,3 -Trimethylindan-4-yl) acetamide (1.8 g, 6 mmol) in 10 ml of acetone was added with 0.75 g of ammonium dithiocarbamate.
(6 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. Then, the mixture was heated under reflux for 1 hour. After allowing to cool, add water and ethyl acetate,
The insoluble material was separated and separated. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate / n-hexane = 1/2),
The crystals were recrystallized from n-hexane-ethyl acetate to obtain 0.8 g of pale yellow crystals (Compound No. 7 shown in Table 4).
The yield was 45%.

Inventive compound No. 8 shown in Table 4 was produced in the same manner except that the raw materials were changed.

Production Example 5 3-Chloro-N- (1,1,3-trimethylindane-4
-Yl) pyrazine-2-carboxamide 3-hydroxypyrazine-2-carboxylic acid 0.5 g (3.57
mmol) and 3 ml of phosphorus oxychloride and 1 drop of pyridine,
The mixture was heated under reflux for 3 hours. Distill off excess phosphorus oxychloride,
5 ml of ethyl acetate was added to the obtained residue. This solution
4-Amino-1,1,3-trimethylindane 0.53 g (3 mmo
l) and 0.4 g (3.96 mmol) of triethylamine were added dropwise to 10 ml of an ethyl acetate solution. After stirring at room temperature for 2 hours, water,
Top washing was performed with sodium hydrogen carbonate, water and saturated saline. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure, and the obtained residue was separated and purified by silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1/4) to give 0.58 g of pale yellow crystals (Table- Compound No. 10) described in No. 5 was obtained. The yield was 61%.

Inventive compounds Nos. 11, 12 and 13 shown in Table 5 were produced in the same manner except that the raw materials were changed.

Production Example 6 4-Methyl-N- (1,1,3-trimethylindane-4
-Yl) Synthesis of 1,2,3-thiadiazole-5-carboxamide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid 1.5 g (10.4 mmol) in thionyl chloride 5 ml and pyridine 1
A drop was added and the mixture was heated under reflux for 1 hour. Excess thionyl chloride was distilled off under reduced pressure, and the residue was dissolved in 10 ml of ethyl acetate. 1.7 g of 4-amino-1,1,3-trimethylindane (9.7 mm
ol) and 4 ml of triethylamine were added to a 10 ml solution of ethyl acetate, and the mixture was stirred at room temperature for 3 hours. The reaction solution was top-washed with water, aqueous sodium hydrogen carbonate solution, water, and saturated saline. After drying over magnesium sulfate, the mixture was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (elution solvent:
Separation and purification with ethyl acetate / n-hexane = 1/9) gave 2.17 g of white crystals (Compound No. 14 in Table 6). The yield is
It was 69.1%.

Compound Nos. 15 and 16 shown in Table 6 were produced in the same manner except that the raw materials were changed.

Production Example 1 20 parts of Compound No. 1, 75 parts of diatomaceous earth, and 5 parts of a surfactant containing alkylbenzenesulfonic acid as a main component were uniformly pulverized and mixed to obtain a wettable powder.

Production Example 2 40 parts of compound No. 10, white carbon 10 parts, diatomaceous earth 4
7 copies, "Solpol" 5039 (trademark of Toho Chemical Industry Co., Ltd.,
3 parts of a surfactant containing polyoxyethylene alkylaryl ether sulfonate as a main component was uniformly pulverized and mixed to obtain a wettable powder.

Production Example 3 Compound No. 15 (30 parts), "Solpol" 3005X (trademark of Toho Chemical Industry Co., Ltd., mixture of nonionic surfactant and anionic surfactant), 15 parts, xylene 25 parts, dimethylformamide An emulsion was obtained by mixing and dissolving 30 parts.

Formulation Example 4 2 parts of compound No. 1 and 98 parts of N, N-kaolin clay (manufactured by Tsuchiya Kaolin Co., Ltd.) were mixed and pulverized to obtain a powder.

Next, the usefulness of the compound of the present invention as an agricultural / horticultural fungicide is clarified by giving test examples.

The compounds of the present invention are shown by the compound numbers in Tables 4, 5 and 6, and the compounds used for comparison and control are shown by the compound symbols in Table 7.

Test Example 1 Drug-sensitive cucumber gray mold control effect test Cucumber at the cotyledon stage (variety:
A water dispersible powder prepared in the same manner as in Preparation Example 1 was diluted to a predetermined concentration with water and sprayed on foliage at a rate of 10 ml per pot. After air-drying the drug solution, spray-inoculated drug-sensitive Botrytis cinerea (Botrytis cinerea) was sprayed and inoculated and kept in a humid chamber at 23 ° C for 4 days after the inoculation, and then the disease state was investigated.
The survey method was as follows. That is, the degree of disease is 0, 1, or
The number of leaves n ₀ , which is classified into an index of 3 and 5 and corresponds to the name disease index,
n ₁ , n ₃ , and n ₅ were investigated and calculated by the following formula. (N is the total number of leaves in the survey) The control value was calculated by the following formula.

The results are shown in Table-8.

Test Example 2 Drug-resistant cucumber gray mold control effect test Cucumber (variety:
A water dispersible powder prepared in the same manner as in Preparation Example 1 was diluted to a predetermined concentration with water and sprayed on foliage at a rate of 10 ml per pot. After air-drying the drug solution, a drug-resistant Botrytis cinerea (Botrytis cinerea) was spray-inoculated and kept in a humid chamber at 23 ° C for 4 days after the inoculation, and then the disease state was investigated. The survey method was as follows. That is, the degree of disease is 0, 1, or
Number of leaves n ₀ , which is classified into 3 and 5 indices and corresponds to the disease index,
n ₁ , n ₃ , and n ₅ were investigated and calculated from the following formula. (N is the total number of leaves in the survey) The control value was calculated by the following formula.

The results are shown in Table-9.

Test Example 3 Wheat Powdery Mildew Control Effect Test A wettable powder prepared in the same manner as in Formulation Example 1 was added to water at a predetermined concentration in 1-2 leaf stage wheat (variety: Norin 61) grown in pots with a diameter of 6 cm. Diluted and sprayed on foliage at a rate of 10 ml per pot. After air-drying the chemicals, spray inoculate with a spore suspension obtained from wheat leaves affected by wheat powdery mildew (Erysiphe graminis) and then inoculate it in a greenhouse.
Left for ~ 10 days.

For evaluation, the diseased area ratio of each leaf was evaluated and the control value was calculated by the following formula.

Test Example 4 Rice crest blight control effect test A wettable powder prepared in the same manner as in Formulation Example 1 was diluted with water to a prescribed concentration in the 3-4 leaf stage rice (cultivar: Nihonbare) grown in a pot with a diameter of 6 cm. The foliage was sprayed at a rate of 10 ml per pot. After air-drying the drug solution, spray inoculate the mycelium suspension of Rhizoctonia solani , which was cultivated in YG medium, and keep it in a humid chamber at 29 ° C for 40 hours, then leave it in a greenhouse water tank for 3 days. Then, the degree of onset of the lesions appearing was measured and the control value was calculated by the following formula. The results are shown in Table-11.

Test Example 5 Wheat leaf rust control effect test For a 1-2 leaf stage wheat (variety: Norin 61) grown in a pot with a diameter of 6 cm, a wettable powder prepared in the same manner as in Test Example 1 was made to have a predetermined concentration with water. Diluted and sprayed on foliage at a rate of 10 ml per pot.

After air-drying the chemicals, spray-inoculate with a spore suspension obtained by grinding wheat infected with wheat rust Puccinia recondita and keeping it in a humid chamber at 22 ° C for 15 hours, then in a greenhouse water tank. Left for 7 days.

For the evaluation, the lesion area ratio of each leaf was evaluated and the control value was calculated by the following formula.

The results are shown in Table-12.

Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location A01N 43/78 CD 43/80 102 43/828 C07D 275/03 277/56 285/06 (72) Inventor Hirofumi Tomita 1000 Kamoshida-cho, Midori-ku, Yokohama-shi, Kanagawa Sanryo Kasei Co., Ltd.Institute of Research (72) Nobuyuki Nonaka 1000 Kamoshida-cho, Midori-ku, Yokohama, Kanagawa Sanryo Kasei Co., Ltd.

Claims (2)

[Claims] 1. The following general formula (I): [In the above formula, A is a group, Represents (In the group, X represents a halogen atom, a methyl group or a trifluoromethyl group, and Y represents a hydrogen atom, a halogen atom other than a chlorine atom, a lower alkyl group other than a methyl group, a mercapto group or a lower alkylthio group.) R Represents a lower alkyl group, and n represents an integer of 1 to 6. ] The N-indanyl carboxylic acid amide derivative shown by these. 2. The following general formula (I) [In the above formula, A is a group, Represents (In the group, X represents a halogen atom, a methyl group or a trifluoromethyl group, and Y represents a hydrogen atom, a halogen atom other than a chlorine atom, a lower alkyl group other than a methyl group, a mercapto group or a lower alkylthio group.) R Represents a lower alkyl group, and n represents an integer of 1 to 6. ] The agricultural and horticultural fungicide containing the N-indanyl carboxylic acid amide derivative shown by these as an active ingredient.