JPH02175A - N-indanylcarboxylic acid amide derivatives and agricultural and horticultural fungicides containing the same as active ingredients - Google Patents

Abstract

NEW MATERIAL:The N-indanylcarboxylic acid amide derivative of formula I [A is group of formula II-V; X is halogen, methyl or trifluoromethyl; Y is H, halogen, lower alkyl, amino, mercapto or lower alkylthio; R is lower alkyl; n is 1-6]. EXAMPLE:2-Amino-N-(1,1-dimethylindan-4-yl)-4-methylthiazole-5-ca-rboxa mide. USE:Useful as an agricultural and horticultural fungicide. It exhibits excellent controlling action against pathogenic fungi of various plants and is harmless to plant. It has low toxicity to human, animal and fish. PREPARATION:The objective compound of formula I can be produced by reacting a thiazole-5-carboxylic acid compound of formula VI or its reactive derivative with an aminoindane derivative of formula VII. The amount of the compound of formula VI is preferably 0.5-1.5 equivalent based on the compound of formula VII.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an N-indanylcarboxylic acid amide derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

[Problems to be solved by conventional technology and invention]

Conventionally, certain carboxylic acid amide derivatives have been known to have biological activities such as bactericidal effects, and other compounds have been confirmed to have bactericidal activities. However, as is clear from the test examples described below, the efficacy of these compounds as agricultural and horticultural fungicides is not always sufficient.

Benzimidazole/thiophanate fungicides such as benomyl [methyl l-(butylcarbamoyl) penzimidazole-ylcarbamate] and thiophanate methyl [Z, It shows excellent control effects against various pathogenic bacteria parasitic on agricultural and horticultural crops, and has been widely used as an agricultural and horticultural fungicide since the 1970s.

However, pathogenic bacteria that are resistant to these disinfectants (hereinafter referred to as drug-resistant bacteria) have become widespread, making them virtually impossible to use.

Cyclic imide fungicides such as glosimidone [N-(3,s-dichlorophenyl)-to-λ-diethylcyclopropane-hakojirupoximide] have been shown to be active against such drug-resistant botrytis fungi, and have therefore been recommended as an alternative. However, in recent years, pathogenic bacteria that are resistant to such cyclic imide fungicides have become widespread, and situations have often arisen where they are virtually impossible to use.

It has been reported that N-phenyl carbamate compounds described in JP-A-726356 and the like exhibit high activity against such resistant bacteria.

However, N-phenyl carbamate compounds are
Since ξ- shows no effect on drug-sensitive bacteria, it may not be possible to use it alone.

Means for Solving Problem E] As a result of intensive studies in view of the above problems, the present inventors have discovered a compound that has a strong bactericidal effect on both drug-susceptible and drug-resistant bacteria, and have completed the present invention. reached.

That is, the gist of the present invention is that the following general formula (I) (in the group,
represents a halogen atom, a methyl group or a trifluoromethyl group, and Y represents a hydrogen atom, a halogen atom, a lower alkyl group, an amine group, a mercapto group or a lower alkylthio group. ) R represents a lower alkyl group, and n represents an integer from 1 to O. ] The present invention relates to an N-indanylcarboxylic acid amide derivative represented by the following and an agricultural and horticultural fungicide containing the same as an active ingredient.

The present invention will be explained in detail below.

The compound of the present invention is represented by the general formula (1) shown above.

In the group, X is a halogen atom, a methyl group or a trifluoromethyl group, and Y is a hydrogen atom, a halogen atom, a lower alkyl group, an amino group, a mercapto group or a lower alkylthio group. Preferably, Y is a hydrogen atom, a lower alkyl group, or an amino group, particularly preferably a hydrogen atom or a lower alkyl group. The lower alkyl group is most preferably a methyl group.

In formula (I), R is a lower alkyl group, preferably a G-Cs lower alkyl group, and a methyl group is particularly preferred. n is an integer of /-A, preferably 7 to
is an integer of In the case of n or an integer from λ to B, R in formula (1) may be equal to or different from each other. Those in which R is not substituted at the 3-position of the indane skeleton are particularly preferred because they exhibit effective activity against botrytis.

Specific examples of the compounds of the present invention represented by general formula (1) include those shown in Tables 7 to 3, but the compounds of the present invention are not limited to these.

Table/Table - Table All of the compounds of the present invention are new compounds, for example,
It is produced according to the reaction formula below.

(fln (old) (I) (
In the above reaction formula, A, R and n have the same meanings as in the forepaw general formula (1). ) The above reaction is carried out using thiazole-carboxylic acids represented by the general formula (It) or reactive derivatives thereof, and the general formula (I
This is carried out by reacting the aminoindan derivative represented by I) in the presence or absence of a solvent inert to the reaction.

The thiazole-5-carboxylic acids represented by the general formula (II) or reactive derivatives thereof used in the reaction are represented by the general formula (
o for the aminoindan derivative represented by fl[),
s-i, s equivalent, preferably used in the range of 0.9 to /, /equivalent. This reaction can be carried out in a temperature range from -70° C. to the boiling point of the solvent used, preferably from -10° C. to the boiling point of the solvent.

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

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

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

Examples of reaction aids include dehydrating agents such as ethoxyacetylene, dicyclohexylcarbodiimide, and phosphorus pentoxide when using carvone as (■), and N-methylmorpholine and triethylamine when using acid anhydrides. Tertiary amines such as pyridine, picoline, N, N-
Aromatic bases such as diethylaniline, tertiary amines such as triethylamine when acid halides are used; aromatic bases such as pyridine and picoline; alkali metal waters such as sodium hydroxide and potassium hydroxide. Oxide: Alkali metal hydride such as sodium hydride;
Alternatively, an alkali metal alcoholade such as sodium ethylate can be used, and when a carboxylic acid ester is used, an alkali metal alcoholade such as sodium ethylate can be used.

These reaction aids are usually o, oi to 2.0 equivalents, preferably o, q to /,!, relative to the aminoindan derivative represented by the general formula (fl). Equivalent amounts can be used.

The compound of the present invention can also be produced using the following rearrangement reaction, depending on the case.

(■) (1) (In the above reaction formula, A, R and n have the same meanings as in the above general formula (1).) In the above reaction, the acyltetrahydroquinoline derivative represented by the general formula (IV) is Bottom, -gθ℃～koo
This is carried out by rearrangement at 0°C, preferably 03-750°C.

Examples of the acid catalyst include sulfuric acid, phosphoric acid, polyphosphoric acid, Lewis acid, etc., and the amount thereof can be from 0.00/equivalent to a large excess relative to the acyltetrahydroquinoline derivative.

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

(IV) (V) (In the above reaction formula, X, Y, R and n have the same meanings as above.) The reaction is carried out by reacting the indicated chloracetamide derivatives 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 has a θ·s-i, s equivalent, preferably 0.9 to 1, to the chloroacetamide derivative represented by the general formula (n). .2 equivalents are used. This reaction is carried out at temperatures ranging from -70°C to the boiling point of the solvent used, preferably -y.

It can be carried out at a temperature range from °C to the boiling point of the solvent.

Examples of solvents 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.

All of the compounds of the present invention thus obtained are novel and have excellent bactericidal activity. In particular, it has excellent control power against various plant pathogens and is useful as a fungicide for agriculture and horticulture.

When using the compound of the present invention as an agricultural and horticultural fungicide, the compound may be used as it is, but in order to effectively disperse the active ingredient at the time of application, an adjuvant may be added according to a conventional method. It is preferable to use it in the form of an emulsion, an aqueous solution, a powder, etc.

Examples of solvents that are one of the auxiliary agents in the agricultural and horticultural fungicides of the present invention include water, alcohols (methyl alcohol, ethyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), and ethers ( ethyl ether, dioxane, cellosolves, etc.], aliphatic hydrocarbons (kerosene, kerosene, fuel oil, etc.), aromatic hydrocarbons (benzene, toluene, xylene, turbentane, methylnaphthalene, etc.), halogenated hydrocarbons (dichloroethane, 1) chlorobenzene, carbon tetrachloride, etc.), acid amides (dimethylformamide, etc.), esters (ethyl acetate, butyl acetate, glycerin esters of fatty acids, etc. 9, 2)!M (acetonitrile, etc.) etc., and a mixture of seven or two or more of these may be used.

1. As fillers, mineral powders such as clays such as kaolin and bentonite, talcs such as talc and pyrophyllite, oxides such as diatomaceous earth and white carbon, soybean powder, carboxymethyl cellulose (CMC), etc. Vegetable powders and the like are suitable, and mixtures of seven or more of these are used.

Additionally, surfactants may be used as spreading agents, dispersants, emulsifiers, and penetrants. Examples of the surfactant include nonionic surfactants (polyoxyethylene alkyl allyl ether, polyoxyethylene sorbitan monolaurate, etc.), cationic surfactants (alkyldimethylbenzylammonium chloride, alkylpyridinium chloride, etc.) , anionic surfactants (alkylbenzenesulfonates, ligninsulfonates, higher alcohol sulfates), amphoteric surfactants (alkyldimethylbetaine, dodecylaminoethylglycine, etc.).

These surfactants are used as a mixture of 7 types or 2 or more types depending on the purpose.

When applying the agricultural and horticultural fungicide of the present invention in the form of an emulsion, 10 to 60 parts of the compound of the present invention and 1 part of a solvent are used.
A stock solution is prepared by mixing 10 parts of O-1 and 0 parts of surfactant J-J in an appropriate ratio, diluted with water to a predetermined concentration before use, and applied by a method such as spraying.

In addition, when used in the form of an irrigation agent, the compound s of the present invention
-go part and extender io-'yo part and surfactant/
-20 parts are mixed in an appropriate ratio, and the mixture is diluted with water or the like in the same manner as in the case of emulsions.

When used in the form of a powder, the compound of the present invention is usually mixed with 7 to 5 parts of a bulking agent such as kaolin, bentonite, Merck, etc. Use a uniform mixture of

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

The agricultural and horticultural fungicide of the present invention can be suitably applied by either foliar spraying or water surface application.

In the case of foliage spraying, the emulsion or irrigation agent is usually applied at a rate of 10 to 10%
It is sufficient to dilute it with water to contain 000 ppm and apply it to lθR/0-3001.

[Effects of the Invention] All of the compounds of the present invention are novel and have excellent bactericidal activity. For example, rice sheath blight (Rh1zoctonia)
5olani), various rust diseases of wheat (Puc
cinia recondita), snow rot (Typ.
hulaincarnate, T, 1shikari
ensis), leaf rot disease of lawns, grasses, etc. (Rh1zoc
tonia 5olani) - gray mold (Botrytis cinerea) of various crops, rice blast (Pyricularia oryzae)
and powdery mildew of various crops (Erysiphe gram
inis) and sclerotia of various crops (5clerotin
It has a strong bactericidal effect against bacteria such as Ia sclerotiorum. In particular, it has extremely high activity against gray mold, both against bacteria susceptible to benzimidazole-thiophanate fungicides and cyclic imide fungicides, and against bacteria that are resistant to them. It is useful as a fungicide.

In addition, although the compounds of the present invention have permeability to plants, they have almost no harmful effects on plants, and have low toxicity to humans, livestock, and fish, so they are generally useful for controlling plant diseases. .

〔Example〕

Next, the present invention will be explained in more detail by giving examples.
The present invention is not limited to the following examples unless it exceeds the gist thereof.

Note that hereinafter, "parts" indicate "parts by weight." In addition, the structures of all the compounds of the present invention synthesized in the production examples were confirmed by elemental analysis, IR spectra, NMR spectra, etc.

Production Example 1 Synthesis of co-amino-N-(/,/-dimethylindan-dayl]-termethylthiazole-j-carboxamide Thiourea o, tt s ji (s, 9 rrmol
) was added with an ethanol/Oml solution of 0.95 t (J, 1I mmol) of coaceto-chloro N-(/,/-dimethelindan-daleyl)acetamide, and the mixture was heated under reflux for 2 hours. After cooling, a 5N aqueous sodium hydroxide solution was added to the reaction solution to make it alkaline, and the precipitated crude crystals were filtered off. The obtained crude crystals were recrystallized with ether to give pale yellow crystals o, qs.
? (Compound A/ listed in Table 1) was obtained. Yield is 93%
Met.

Compound &3 of the present invention described in Table 1 was produced in the same manner except that coaceto λ-chloro-N-(ham-3-trimethylindan-guyl)acetamide was used as the raw material.

Production example Coco, Synthesis of lI-dimethyl-N-(Ham J-)liethyl indan-yl]thiazole-5-carboxamide Oy to acetamide (3,
smmol) of thioacetamide in some benzene solution. (1), j mmol) was added, and the mixture was heated under reflux for /, S hours. After cooling, the reaction solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate/hexane = / /
Separation and purification in step 2) yielded white crystals in step 1. OS? (Table-
Compound 1fx2; m, p, / / 7-/
/g″C) was obtained. The yield was a barrel.

All of the compounds of the present invention &5 described in Table-&i/(2) were produced in the same manner except that the raw materials were changed.

Production Example 3 Synthesis of goomethyl-N-(/,/,,?-trimethylindan-gooyl)thiazole-5-carboxamide goomethyl-5-thiazolecarboxylic acid/, 7f (/
(1),,? mmol) K thionyl chloride 10
ml was added and heated under reflux for 7 hours. Excess thionyl chloride was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate toml. This solution was mixed with 1.
10 ml of ethyl acetate solution containing 100 ml of triethylamine (IO, smmol) and 3 ml of triethylamine at room temperature.
Stir for hours. The reaction solution was washed successively with water, an aqueous solution of hydrogen carbonate, water, and saturated brine. After drying magnesium sulfate, it was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (elution solvent: ethyl acetate/
Separation and purification using n-hex 7=//2) gave an amorphous solid Aff (compound && listed in Table 1).

The yield is! I was in charge of 0.2.

Compounds jFx4' and A9 of the present invention shown in Table 1 were produced in the same manner except that the starting materials were changed.

Preparation Example D11 Synthesis of merkabutodermethyl-N-(/,/,,?-triethylindan-thalylnoteazole-!-carboxamide) 2-aceto-r,2-chloro-N-(ham 3-trimethyl (A m
0.7 s t (A mmo!) of ammonium dithiocarbamate in 10 ml of acetone solution (A mmo!)
was added and stirred at room temperature for 30 minutes. The mixture was then heated under reflux for 1 hour. After cooling, add water and ethyl acetate to remove insoluble matter.
The liquid was separated. The organic layer was washed with saturated brine, dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/n-hexane=//j), and further n
-hexane-ethyl acetate? Recrystallization was carried out using the following methods to obtain pale yellow crystals o and gt (compounds &7 listed in Table D). The yield was Das%.

The hardware according to the invention shown in Table 9 was manufactured in the same manner except that the raw materials were changed.

Preparation Example S Synthesis of 3-chloro-N-(/,/,,?-)lyntylindan-guyl)virazine-cocarpoxamide 3-hydroxyvirazine-cocarboxylic acid θ,s 9
(j, s 7 mmol), phosphorus oxychloride, 7
277 drops of at and piri were added, and the mixture was heated under reflux for 3 hours.

Excess phosphorus oxychloride was distilled off, and s ml of ethyl acetate was added to the resulting residue. This solution was mixed with 0.532 (3 mmol) of teramino-ham 3-trimethylindan.
, triethylamine 0. lI'? (,3,91゜mmo
It was added dropwise to 1 ml of ethyl acetate solution of 1).

After stirring for several hours in a chamber, add water, sodium bicarbonate,
It was washed successively with water and saturated saline. After drying magnesium sulfate, it was concentrated under reduced pressure, and the resulting residue was separated and purified using silica gel column chromatography (eluent: ethyl acetate/n-hexane) to obtain 0.5 g of pale yellow crystals.
? (Compound A/0 listed in Table-5) was obtained. The yield was 67 cm.

Compounds of the present invention A//, /2 and /3 listed in Table 5 were produced in the same manner except that the raw materials were changed.

Production Example 6 Synthesis of goomethyl 7-N (/, /, J) ethyl indan-hiro-yl]-heco, 3-thiadiazole-5-carboxamide Hiro-methyl-/, 2,7-thiadiazole-5-carvone Thionyl chloride s me and 1 drop of pyridine were added to acid s t (/0.1 mmol), 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 ethyl acetate IQ! n/! dissolved in. This solution was mixed with guamino-ham 3-trimethylindan/, 72 (9,7 mmo
l ) and triethylamine ml of ethyl acetate io
ml solution and stirred at room temperature for 3 hours. Add the reaction solution to water,
It was washed successively with an aqueous sodium hydrogen carbonate solution, water, and saturated brine. After drying magnesium sulfate, it was concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (elution solvent: ethyl acetate/n-hexane = //9) to obtain white crystals! , /7F (Compound A listed in Table-6
/4') was obtained. The yield was bq, 7%.

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

A wettable powder was obtained by uniformly pulverizing and mixing 20 parts of Formulation Example/Compound Chamber/, ±75 parts of diatoms, and 5 parts of a surfactant containing alkylbenzenesulfonic acid as a main component.

Formulation Example Co-Compound A/0 was mixed with 1 part of Hiro θ, 1 part of White Carbon, 7 parts of Diatomaceous Earth, and "Tsurpol 3039 (Toho Chemical Co., Ltd.)
A wettable powder was obtained by uniformly grinding and mixing 3 parts of polyoxyethylene alkylaryl ether sulfonetra (a surfactant based on Polyoxyethylene Alkylaryl Ether Sulfonetra).

Formulation Example 3 30 parts of Compound Room 15, 75 parts of 'Tsurpol, yoos An emulsion was obtained by mixing and dissolving.

Formulation Example Compound A/ was mixed and pulverized with a part and a part of N, N-force olin clay (manufactured by Saturn Kaolin Co., Ltd.) to obtain a powder.

Next, by giving a test example, the usefulness of the compound of the present invention as a fungicide for agricultural and horticultural purposes will be clarified.

The compounds of the present invention are indicated by compound numbers in Tables G, 5 and O, and the compounds used for comparison are indicated by compound symbols in Table 7.

Test Example / Effect test on gray mold disease control on drug-sensitive cucumbers Cotyledon-stage cucumbers (variety Niyoyoba) grown in pots with a diameter of 6crIL were treated with sea bream agent example / A wettable powder prepared in the same manner as in the above was added to a specified concentration with water. It was diluted and sprayed on foliage at a rate of 10 ml per bot. After air-drying the chemical solution, the drug-susceptible botrytis fungus (
Botrytis cinerium
ea) was spray-inoculated and kept in a greenhouse at 23°C for several days after inoculation to investigate the late-onset disease state. The investigation method was as follows.

In other words, the disease severity is determined by calculating the percentage of diseased area of the examined leaves, and depending on the degree, 0. /,,7,! The number of leaves nO, nl % n3, n5 corresponding to each disease index was investigated and calculated using the following formula. (n is the total number of leaves surveyed) The control value was calculated using the following formula.

Table of results-g Shown below.

Test Example K: Drug-resistant cucumber gray mold control effect test Cotyledon stage cucumber (variety: four-leaf) seedlings grown in pots with a diameter of 6 cTL. A wettable powder prepared in the same manner as Km Preparation Example/ was diluted with water to a specified concentration. The mixture was sprayed on foliage at a rate of 10 ml/bot. After air-drying the chemical solution, a drug-resistant gray mold fungus (Botrytis cinerea
) was spray-inoculated and kept in a greenhouse at 70°C for several days after inoculation to investigate the late-onset disease state. The investigation method was as follows. In other words, the disease severity is calculated by calculating the percentage of diseased area of the investigated leaves, and depending on the degree, 0, /, J,! ; The number of leaves, nl, nl, n, corresponding to each disease index was investigated and calculated using the following formula. (n is the total number of leaves surveyed) The control value was calculated using the following formula.

The results are shown in Table-9.

table? Test Example 3 Wheat powdery mildew control effect test diameter 6cIIL
Wheat seedlings were grown in pots at the single-leaf stage (variety: Norin 6)
/ No.) An irrigation agent prepared in the same manner as VC formulation example / was diluted with water to a predetermined concentration and sprayed on foliage at a rate of 10 ml per 1 pot. After air-drying the chemical solution, wheat powdery mildew (Erici 7)
Erysiphe graminis
) After spraying inoculation with a spore suspension obtained from leaves of wheat infected with the disease, the plants were left in a greenhouse for 7 to 10 days.

For evaluation, the diseased area ratio of each leaf was assessed and the pest control value was calculated using the following formula.

Test Example G Rice sheath blight control effect test A hydrating powder prepared in the same manner as Formulation Example/ was diluted with water to a predetermined concentration on rice (variety: Nipponbare) from the 3rd to Hiroba stages grown in pots with a diameter of AC1rL. The mixture was sprayed on foliage at a rate of 10 ml per pot/pot. After air-drying the chemical solution, Rh1zoctonia 5 was cultured on YG medium.
olani) was spray-inoculated and heated at 29°C.
After keeping the plants in a greenhouse for 70 hours, they were left in an aquarium in the greenhouse for 3 days, the severity of the lesions that appeared was measured, and the pest control plot was calculated using the following formula. The results are shown in Table-7/.

Test Example j Wheat rust control effect test Seedlings were grown in pots with a diameter of 6CrIt/-j leaf stage wheat (variety: Norin 61)
No.), a hydrating powder prepared in the same manner as in Test Example 1 was diluted with water to a predetermined concentration and sprayed on foliage at a rate of pioml per 1 pot.

After the chemical solution was air-dried, a spore suspension obtained by grinding wheat infected with wheat rust (Puccinia recondita) was spray inoculated.
After keeping it in a greenhouse at 22°C for 15 hours, it was left in a greenhouse aquarium for 7 days.

For evaluation, the lesion area ratio on each leaf was assessed and the control value was calculated using the following method.

The results are shown in Table 1.

Mitsubishi Chemical Industries, Ltd.

Claims (2)

[Claims] (1) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・(
I) [In the above formula, A is a group, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas, chemical formulas, tables, etc. etc. 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, a lower alkyl group, an amino group, a mercapto group or a lower alkylthio group.) R represents a lower alkyl group. where n represents an integer from 1 to 6. ] N-indanylcarboxylic acid amide derivative represented by these. (2) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・(
I) [In the above formula, A is a group, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Mathematical formulas, chemical formulas, tables, etc. etc. 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, a lower alkyl group, an amino group, a mercapto group or a lower alkylthio group.) R represents a lower alkyl group. where n represents an integer from 1 to 6. ] An agricultural and horticultural fungicide characterized by containing the following N-indanylcarboxylic acid amide derivative as an active ingredient.