JPS62249966A - N-indanylamide derivative and fungicide containing same as active ingredient - Google Patents

Abstract

NEW MATERIAL:An N-indanylamide derivative of formula I (R<1>, R<2> are H, halogen, methyl, trifluoromethyl; R<3> is H, methyl; X is O, S, NCH3). EXAMPLE:2-Methyl-N-(1,1-dimethylindan-4-yl)furan-3-carboxamide. USE:A fungicide which has preventive and curative effect against a variety of plant disease-causative microorganisms, especially against plant diseases caused by microorganisms in Basidiomycetes. PREPARATION:The reaction of an acid halide of formula II (Y is halogen) with 4-aminoindane gives the compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel N-indanilamide derivative and a sedative containing the same as an active ingredient.

<Prior Art> Hitherto, it has been known that anilide derivatives such as carboxin, mepronic acid and fenrum can be used as active ingredients in fungicides.

<Problems to be Solved by the Invention> However, it cannot be said that these anilide derivatives are necessarily sufficient as effective ingredients for fungicides.

Means for Solving the Problems> In view of the above circumstances, the present inventors conducted various studies to develop a compound with excellent bactericidal activity, and as a result, an N-indanyl heteroaromatic carboxylic acid amide compound was found. It was discovered that this compound has excellent bactericidal activity, leading to the present invention.

That is, the present invention provides a compound of the general formula CI"J [wherein R1 and R2 are the same or different and represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and R8 represents a hydrogen atom or a methyl group,
X is an oxygen atom, a sulfur atom, or a methylimino group (〉N
-CH,). ] The present invention provides an N-indanilamide derivative represented by the following and a fungicide containing the same as an active ingredient.

The compound of the present invention has preventive and therapeutic bactericidal effects against plant diseases caused by various plant pathogens, particularly microorganisms belonging to the Basidiomycetes, and is therefore used as an active ingredient of fungicides.

Plant diseases for which the compound of the present invention has excellent efficacy include:
For example, rice sheath blight (Rh1zoctoniasola
ni), pseudosheath blight (Rh1zoctonia or
yzae.

R, 5olani l type B), wheat rust (Pu
cciniastriformis, P. grami
nis, P. recondita, P.

hordei), snow rot (Typbula 1ncar)
nata, T.

1shikariensis), Usti
lag.

tritici, U, nuda), damping-off of various crops (Rhizoctonia 5olani),
Corticium rolfsii, potato and beet diphtonia (Rh1zocto)
nia 5olani), pear red star disease (Gyn+no
sporangium haraeanum), apple scab (Venturia 1naequaris)
) % Leaf rot disease of grasses, lawns, etc. (Rh1zoctoni
a 5olani), Corticium r.
olfsii), leaf rust (Uromyceatrif
olii), W rot (Typhula 1ncarn)
ata.

T, 1shikariensis) and the like.

When using the compound of the present invention as an active ingredient of a fungicide,
Although it may be used as is without adding any other ingredients, it is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to form emulsions, wettable powders, suspensions, and granules. , powder,
It is used by formulating it into a liquid formulation, etc.

The content of the compound of the present invention as an active ingredient in these preparations is 0.1 to 99.9%, preferably 0.2% in terms of gravity ratio.
It is in the range of ~80%.

In the above formulation, the solid carriers include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate,
Examples include fine powders or granules such as synthetic hydrous silicon oxide, and liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropynol, ethylene glycol, and cellosolve, acetone, cyclohexanone, and isophorone. ketones, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile,
Water etc. can be given.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Anionic surfactants such as sulfonates, sialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyenalene alkyl ethers, polyoxyethylene polyoxypropylene blocks Examples include nonionic surfactants such as copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.

As formulation adjuvants, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC
(carboxymethylcellulose), F'AP (isopropyl acid phosphate), and the like.

The formulation is applied directly to plants or to soil, either undiluted or diluted with water, for example.

More specifically, it is used in various forms, such as by spraying or dusting on plants, scattering, dusting or granulating on the soil surface, or further mixing with soil if necessary.

Furthermore, by mixing it with other fungicides, it can be expected to increase the bactericidal efficacy. Furthermore, it can also be used in combination with insecticides, acaricides, nematicides, plant growth regulators, fertilizers, and soil conditioners.

The compound of the present invention can be applied to rice fields, upland fields, orchards,
It can be used as an active ingredient in fungicides for lawns, etc.

When the compound of the present invention is used as an active ingredient of a fungicide, the application amount varies depending on weather conditions, formulation form, application timing, method, location, target disease, target crop, etc., but usually 1.
0.5-100g per are, preferably 1g-5
0g, and when applying emulsions, wettable powders, suspensions, solutions, etc. diluted with water, the application concentration is 0.001% to 1%.
%, preferably 0.005% to 0.5%, and granules, powders, etc. are applied as they are without any dilution.

Examples of the compounds of the present invention include the following.

2-Methyl-N-(1,1-dimethylindan-4-yl)furan-8-carboxamide 2-methyl-N-(1
,1,8-trimethylindan-4-yl)furan-8
-Carboxamide 2-trifluoromethyl-N-(1,1-dimethylindan-4-yl)furan-8-Carboxamide 2-trifluoromethyl-N-(1,1,8-trimethylindan-4-yl)furan -8-carboxamide 2,5-dimethyl-N-(1,1-dimethylindan-
4-yl)furan-8-carboxamide 2,5-dimethyl-N-(1,1,8-)dimethylindan-4-yl)furan-8-carboxamide 5-methyl-2-trifluoromethyl-N-( 1,1-
dimethylindan-4-yl)furan-8-carboxamide 5-methyl-2-trifluoromethyl-N-(1,1,
8-Trimethylindan-4-yl)furan-8-carboxamide 2-methyl-N-(1,1-dimethylindan-4-yl)thiophene-8-carboxamide 2-methyl-N-(1,1,8- Trimethylindan-4-yl)thiophene-8-carboxamide 8-methyl-N-(1,1-dimethylindan-4-yl)thiophene-2-carboxamide 8-methyl-N-(1,1,8-trimethylindan −
4-yl)thiophene-2-carboxamide 2,5-dimethyl-N-(1,1-dimethylindane-
4-yl)thiophene-8-carboxamide 2,5-dimethyl-N-(1,1,8-trimethylindan-4-yl)thiophene-8-C10) carboxamide 8,5-dimethyl-N-(1,1 -dimethylindan-
4-yl)thiophene-2-carboxamide 8,5-dimethyl-N-(1,1,8-)dimethylindan-4-yl)thiophene-2-carboxamide 2-trifluoromethyl-N-(1,1- dimethylindan-4-yl)thiophene-8-carboxamide 2-trifluoromethyl-N-(1,1,8-drimethylindan-4-yl)thiophene-8-carboxamide 3-trifluoromethyl-N-(1 ,1-dimethylindan-4-yl)thiophene-2-carboxamide 8-trifluoromethyl-N-(1,1,8-trimethylindan-4-yl)thiophene-2-carboxamide 5-methyl-2-trifluoro Methyl-N-(1,l-
dimethylindan-4-yl)thiophene-8-carboxamide 5-methyl-2-trifluoromethyl-N-(1,1,
8-)-Dimethylindan-4-yl)thiophene-8
-carboxamide 5-methyl-8-trifluoromethyl-N-(1,1-
dimethylindan-4-yl)thiophene-2-carboxamide 5-methyl-8-trifluoromethyl-N-(1,1,
8-)-dimethylindan-4-yl)thiophene-2
-carboxamide 1-methyl-N-(1,1-dimethylindan-4-yl)pyrrole-2-carboxamide 1-methyl-N-(
1,1,8-)dimethylindan-4-yl)pyrrole-2-carboxamide 1,8-dimethyl-N-(1,1-dimethylindan-
4-yl)pyrrole-2-carboxamide 1,8-dimethyl-N-(1,1,8-trimethylindan-4-yl)pyrrole-2-carboxamide 1,4-dimethyl-N-(1,1-dimethyl Indan
4-yl)pyrrole-2-carboxamide 1,4-dimethyl-N-(t,1.8-)dimethylindan-4-yl)pyrrole-2-carboxamide 1,4-dimethyl-N-(1,1- Dimethyl indane
4-yl) pyrrole-8-carboxamide 1,4-dimethyl-N-(1,1,8-trimethylindan-4-yl) pyrrofure 8-carboxamide The compound of the present invention has, for example, the general formula [11 In the formula, R1, R2 and X have the same meanings as above, and Y represents a halogen atom. ] and the carboxylic acid halide represented by the general formula [厘] [wherein R8 represents the same meaning as above. ] It can be produced by reacting with 4-aminoindanes shown in the following.

In this case, 4- is generally represented by the general formula [Otori].

An appropriate solvent for 1 equivalent of aminoindanes, such as hydrocarbons such as benzene, toluene, xylene, halogenated hydrocarbons such as chlorobenzene, methylene chloride, chloroform, carbon tetrachloride, diisopropyl ether, tetrahydrofuran, dioxane, etc. Ethers, acetone, ketones such as methyl ethyl ketone, esters such as ethyl acetate, nitriles such as acetonitrile, dimethyl sulfoxide, dimethyl formamide, water, etc. are added or in the absence of a solvent, usually 0.4 to 1.5 equivalents, preferably is 0.5~
1.1 A carboxylic acid halide represented by the general formula CD is reacted.

In addition, the above-mentioned solvents may be used for the carboxylic acid halide represented by the general formula [■], or the general formula [ll[1
It is also possible to add and react the 4-aminoindanes represented by.

The reaction can be carried out at a temperature ranging from the freezing point to the boiling point of the solvent, preferably from 0° C. to the boiling point of the solvent, and can be heated or cooled as necessary.

Id etc. can be given.

Further, in the reaction, sodium hydroxide, potassium hydroxide, triethylamine, N-methylmorpholine, triethylamine, pyridine, etc. can be used as a deoxidizing agent.

These deoxidizing agents are usually used in a catalytic amount to 2 equivalents, but preferably 0.95 to 1.1 equivalents can carry out the reaction.

The compound of the present invention obtained by the above production method can also be purified by recrystallization or column chromatography, if necessary.

<Examples> The compounds of the present invention will be explained in more detail below using production examples, formulation examples, and test examples.

Production Example 1.1-dimethyl-4-aminoindan 822-y and viridi'/1t:l(Dl-runxnlQm
A solution of 289 μl of 2-methylfuran-8-carboxylic acid chloride in 8 toluene was quenched with stirring at room temperature, and then stirred at room temperature for 12 hours. Next, the reaction solution was poured into cold water, and after separation, the aqueous layer was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off.

2-Methyl-N-(1,1-dimethylindan-4-yl)furan-8-carboxamide 44 was obtained by recrystallizing the residue using a toluene/n-hexane mixed solvent.
I got 5 da.

mp, 170.1° C. Some representative compounds of the present invention obtained by such a production method are shown in Table 1.

\, -9 ・\) Next, a formulation example is shown. The compounds of the present invention are shown by the compound numbers in Table 1, where "M" stands for "part".

Formulation Example 1 5 parts each of the compounds (1) to (10) of the present invention, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfonate
1 part and 45 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain a hydrating powder.

Formulation Example 2 10 parts each of the compounds (1) to (10) of the present invention, 14 parts of polyoxyethylene methylin phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 70 parts of xylene are thoroughly mixed to obtain an emulsion.

Formulation Example 8 2 parts each of the compounds (1) to (10) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 65 parts of kaolin clay were thoroughly ground and mixed, and water was added. After thoroughly kneading, the mixture is granulated and dried to obtain granules.

Formulation Example 4 25 parts each of the compounds (1) to (10) of the present invention, 8 parts of polyoxyethylene sorbitan monooleate, 8 parts of CMC, and 69 parts of water were mixed and wet-pulverized until the particle size became 5 microns or less. Obtain a suspension.

Formulation Example 5 2 parts each of the compounds (1) to (10) of the present invention, 88 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder.

Next, test examples will show that the compounds of the present invention are useful as active ingredients of fungicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.

Table 2 Test Example 1 Rice sheath blight prevention effect test Plastic pots filled with sandy loam and rice (Kinki No. 88)
were sown and grown in a greenhouse for 60 days. 6-7 leaves are displayed υ
A test compound prepared as an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration, and sprayed on the leaves of rice seedlings so that it would sufficiently adhere to the leaf surface. Four hours after the spraying, a patch of edible agar containing rice sheath blight bacteria was inoculated.

After inoculation, the plants were grown for 4 days at 28°C under humid conditions, and their pesticidal efficacy was investigated.

The results are shown in Table 3.

In addition, the control efficacy is determined by visually observing the diseased state of the test plants at the time of investigation, that is, the degree of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed, it is evaluated as "5", 1O%. If you accept the degree,
4", if it is found in about 80%, it is "2", if it is found in about 50%, it is "I-I J", if it is found in about 70%, it is I-I J, and if there is no difference from the disease onset state when no compound is tested. "0" is evaluated in 6 stages from 0 to 5, and 0.
1.2.8.4.5.

Table 3 Test Example 2 Wheat Rust Treatment Efficacy Test A plastic pot was filled with sandy loam, and Komu (Norin No. 78) was sown.
It was grown in a greenhouse for 10 days. Wheat seedlings with 2nd to 8th leaves developed were inoculated with the wheat rust fungus.

After inoculation, the test compound was grown for 1 day at 28°C and under high humidity, and the test compound prepared as a wettable powder was mixed with Formulation Example 1, diluted with water to a predetermined concentration, and sprayed on the foliage so that it adhered sufficiently to the leaf surface. did. After spraying, the plants were grown for 7 days under lighting at 28°C, and their pesticidal efficacy was investigated.

The results are shown in Table 4.

Test Example 3: Apple scab preventive effect test A plastic pot was filled with sandy loam, and apple seeds were sown and grown in a greenhouse for 80 days. The test compound made into a hydrating powder by applying Formulation Example 1 is diluted with water to a specified concentration, and sprayed on the foliage of apple seedlings that have developed the fifth true leaf so that it adheres sufficiently to the leaf surface. did. Four hours after the spraying, a spore suspension of apple scab fungus was spray inoculated. After inoculation, the plants were grown for 14 days at 15°C under humid conditions, and their pesticidal efficacy was investigated.

The results are shown in Table 5.

<Effects of the Invention> The compounds of the present invention have excellent efficacy against plant diseases caused by various plant pathogenic bacteria, especially microorganisms belonging to the Basidiomycetes. Therefore, it is extremely useful as an active ingredient in disinfectants.

(28 completed)

Claims (4)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom, a halogen atom, a methyl group, or a trifluoromethyl group, 8 represents a hydrogen atom or a methyl group, and X represents an oxygen atom, a sulfur atom or a methylimino group (N-CH_3). ] An N-indanilamide derivative represented by the following. (2) The derivative according to claim 1, wherein in the N-indanilamide derivative represented by the above general formula, R^1 and R^2 are the same or different and represent a hydrogen atom, a methyl group, or a trifluoromethyl group. . (3) General formula [wherein R^1 and R^2 are the same or different and represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and R^3 represents a hydrogen atom or a methyl group, X represents an oxygen atom, a sulfur atom, or a methylimino group (N-CH_3). ] A disinfectant characterized by containing the N-indanilamide derivative shown as an active ingredient. (4) The sterilization method according to claim 3, wherein in the N-indanilamide derivative represented by the above general formula, R^1 and R^2 are the same or different and represent a hydrogen atom, a methyl group, or a trifluoromethyl group. agent.