JPH01301681A - Amide derivative, production thereof, agricultural and horticultural fungicide comprising said derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound shown by formula I (R<1> and R<2> are H or 1-3C alkyl; R<3> is 2-furyl, 3-furyl, 2-thienyl or 3-thienyl). EXAMPLE:2-(2,4-Dimethylthiazol-5-carboxyamino)-2-(2-furyl)aceton-itrile. USE:An agricultural and horticultural fungicide. PREPARATION:1 equivalent acid halide shown by formula II (X is halogen) is reacted with preferably 1-2 equivalent aminonitrile derivative shown by formula III or salt thereof usually at -30-50 deg.C, preferably 0 deg.C-room temperature for 1-8 hours. The reaction is carried out usually in the presence of a base such as pyridine, 4-dimethylaminopyridine, triethylamine or sodium hydroxide optionally in a solvent such as hexane or benzene.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel amide derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.

<Prior Art> As agricultural and horticultural fungicides, cabtan, captafor, and dithiocarbamate drugs are known as those currently widely used, particularly in the fields of late blight and downy mildew. However, all of these drugs have only a preventive effect and do not show any therapeutic effect, and there are problems in disease control by drug treatment after the onset of the disease.

In other words, from the practical spraying situation for plant disease control,
In some cases, spraying may occur after the onset of the disease.
In particular, agents for controlling algae and fungi, where disease symptoms develop rapidly, are required to have high preventive efficacy, excellent systemic transferability, and therapeutic efficacy. Under these circumstances, metalaxyl (N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester), which has excellent permeability and therapeutic activity, was developed; Due to the emergence of resistant bacteria, its excellent therapeutic activity has not been demonstrated.

Currently, particularly in the field of grape disease control, there is a desire for the emergence of therapeutic agents that have new effects and excellent systemic transferability.

Conventionally, amide compounds with fungicidal or herbicidal activity are
Many are known. Among them, as a compound similar to the amide derivative of the present invention, USP-4482784 discloses a compound containing substituted benzene, furan, thiophene, benzofuran, and pyridine as a moiety corresponding to the thiazole ring of the following general formula [I], and USP-4515959. No. or USP-4552887 describes a compound containing substituted benzene, furan, or thiophene, and EP-174088 describes a compound containing a 4-substituted benzene, and JP-A-62-1
No. 08067 describes compounds containing alkyl, alkenyl, alkoxyalkyl, cycloalkyl, haloalkyl, and haloalkenyl.

<Problems to be Solved by the Invention> However, these compounds have poor efficacy in controlling plant diseases, especially those of algae and fungi such as downy mildew and late blight, and in terms of systemic transferability. It is difficult to say that these methods are necessarily satisfactory because they are insufficient in terms of surface area and have extremely strong phytotoxicity to the plants to be controlled.

<Means for Solving the Problems> In view of the above circumstances, the present inventors conducted various studies in order to develop a compound that has excellent efficacy against plant diseases and has less phytotoxicity, and as a result, the present inventors have developed the present invention. The inventors have discovered that amide derivatives have excellent preventive and therapeutic efficacy against plant diseases, have excellent systemic transferability, and do not exhibit phytotoxicity that could not be solved by conventional techniques, leading to the present invention.

That is, the present invention is based on the general formula [wherein R and R are the same or different and represent a hydrogen atom or a lower alkyl group having 1 to 8 carbon atoms, and R8 is 2
-furyl group, 8-furyl group, 2-thienyl group or 8-
Represents a thienyl group. The present invention provides an amide derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.

Among the compounds of the present invention, more preferable compounds in terms of their efficacy are those in the above-mentioned formula [I], where R1 is a methyl group, R2 is a methyl group or an ethyl group, and R8 is 2-
Compounds in which R1 is a methyl group, R2 is an ethyl group, and R'' is a 2-thienyl group or an 8-thienyl group are more preferred.

Next, the present invention will be explained in detail.

The compound of the present invention has the formula E, in which R1 and R2 represent the same meanings as above, and X
represents a halogen atom. ] An acid halide represented by the general formula % formula % [ [wherein R8 represents the same meaning as above. It can be obtained by reacting with an aminonitrile derivative represented by J or a salt thereof.

The reaction temperature and reaction time of the reaction are usually in the range of about -80 to about 50°C, preferably in the range of about -80°C to room temperature, and in the range of about 80 minutes to about 24 hours, preferably in the range of about 1 to about 8 hours. You can achieve that goal.

The reaction is usually carried out in the presence of a base, and examples of the base include 8th class amines such as pyridine, 4-dimethylaminopyridine, triethylamine, N,N-dimethylaniline, tributylamine, and N-methylmorpholine, and water. Examples include inorganic bases such as sodium oxide, potassium hydroxide, calcium carbonate, and sodium hydride.

The amount of the reagents used in the reaction is - 1 equivalent of the acid halide represented by the formula [■], - the amino nitrile conductor represented by the formula [1111] and the base are each about 1 equivalent.
~2 equivalents. Furthermore, the aminonitrile IP represented by the above-mentioned formula [I[] can also be used as the reaction base.

In the above reaction, a solvent is not necessarily required, but preferably a solvent is used. Examples of solvents that can be used in the reaction include aliphatic hydrocarbons such as hexane, heptane, ligroin, petroleum ether, benzene, toluene, Aromatic fF group hydrocarbons such as xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, ethers 1 such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, acetone , methyl ethyl ketone, methyl isobutyl ketone,
Ketones such as isophorone and cyclohexanone, esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate, nitrides such as nitromethane and nitrobenzene,
Nitriles such as acetonitrile and isobutylnitrile,
Formamide, N.

Examples include acid amides such as N-dimethylformamide and N,N-dimethylacetamide, and sulfur compounds such as dimethyl sulfoxide and sulfolane. In addition, when a water-prohibitive base such as sodium hydride is not used, water can also be used as a solvent. Moreover, the above-mentioned solvents can also be used in combination.

After the reaction is complete, perform normal post-treatments such as water washing and concentration.
If necessary, the desired compound can be obtained by purification by operations such as chromatography and (lO) recrystallization.

Moreover, the compound of the present invention has the following formula: - In the formula c, R1 and R2 have the same meanings as above. ] A carboxylic acid represented by the following is reacted with N,N'-thionyldiimidazole to form a compound of the general formula [wherein R1 and R2 have the same meanings as above. ] It can be obtained by obtaining an acylimidazole conductor represented by the following and then reacting this with an aminonitrile derivative represented by the above-mentioned formula [11] or a salt thereof.

In the above reaction, the reaction temperature and reaction time are usually in the range of about -80°C to about 50°C, preferably about θ°C to room temperature,
The purpose can be sufficiently achieved within the range of about 80 minutes to about 24 hours, preferably about 1 to about 8 hours.

The amount of the reagent used in the reaction is usually N, N'- with respect to 1 equivalent of the carboxylic acid represented by the formula [ff].
The thionyldiimidazole is approximately 1 equivalent and has the formula [1
The aminonitrile derivative represented by 1] is about 1 to about 2 equivalents.

In the above reaction, a solvent is not necessarily required, but examples of solvents that can be used in the reaction include the reaction between the acid halide represented by formula [111] and the aminonitrile derivative represented by formula [111]. Among the solvents used for
Extra-Mercurial solvents can be used.

After the reaction is complete, perform normal post-treatments such as water washing and concentration.
If necessary, the desired compound can be obtained by purification by operations such as chromatography and recrystallization.

Further, in the above reaction, since the acylimidazole conductor represented by formula [V] is chemically unstable, it is usually subjected to the next reaction without being isolated.

The lercarboxylic acid represented by the general formula [ff], which is the raw material compound used in the above reaction, is prepared by Ann, 250,257 (18
89) and J. Chem, Soc, 601 (
1945). If necessary, these carboxylic acids can be converted into acid halides using thionyl chloride or the like by a conventional method.

N, N'-thionyldiimidazole, Angew
.

Chem, 78.26 (1961).

Furthermore, the aminonitrile derivative represented by formula [I11] can be obtained by reacting the corresponding aldehyde compound with ammonia and potassium cyanide or sodium cyanide by Schdrecker reaction.

The obtained aminonitrile derivative can also be isolated as a salt. Examples of the salt include inorganic salts such as hydrochloride and sulfate.

The compound of the present invention has optical isomers derived from one asymmetric carbon, and these optical isomers are also included in the present invention.

The compound of the present invention can be used as an active ingredient in agricultural and horticultural fungicides without adding any other ingredients.

However, the compound of the present invention is usually used by mixing it with a solid carrier, liquid carrier, surfactant, or other formulation auxiliary agent to formulate an emulsion, wettable powder, suspension, powder, granule, or the like. In this case, the active ingredient content of the compound of the present invention as an active ingredient in the preparation is 0.1 to 99.9%, preferably 1 to 90%.
It is.

The above-mentioned solid carriers include fine particles such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, acetone, cyclohexanone,
Ketones such as isophorone, vegetable oils such as soybean oil and cottonseed oil,
Examples include dimethyl sulfoxide, acetonitrile, water, and the like.

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

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

Application methods of the compound of the present invention include foliar spraying, soil destruction treatment,
Examples include seed disinfection, but any application method commonly used by those skilled in the art can be used.

When the compound of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, the amount of the active ingredient applied should be determined based on the target crop, target disease,
Although it varies depending on the degree of disease occurrence, formulation form, application method, application period, weather conditions, etc., it is usually 0.01 per are.
~50y1 is preferably 0.05 to 10g, emulsion,
When applying wettable powders, suspending agents, etc. diluted with water, the application concentration is 0.0001 to 0.5%, preferably 0.0%.
0.005 to 0.2%, and powders, granules, etc. are applied as they are without any dilution.

Examples of plant diseases that can be controlled with the compounds of the present invention include the following diseases.

Downy mildew (Peronospora
brassicae), spinach downy mildew (Per.
onosporaspinaciae), tobacco downy mildew (Peronosporatabacina),
Cucumber downy mildew (Pseudoperonospor)
acubensis), downy mildew of grapes (Pla
smoparaviticola), apple, strawberry, and ginseng blight (Phytophthor
a cactorum), gray late blight of tomatoes and cucumbers (Phytophthora capsici),
Pineapple blight (Phytophthora ci)
nnamomi), potatoes, tomatoes, eggplants (Phytophthora infestans)
, Phytophth
ora n1cotianae var, n1cot
ianae), spinach damping-off (Pythium
sp, ), cucumber seedling damping-off (Pythium ap.
hanidermatum), wheat brown haze rot (P
ythium sp,), tobacco damping-off (Pythi
um debaryanum), soybean (D Pyt
hium rot (Pythium aphanide)
rmatum, P, debarynum, P.

irregulare, P. myiotylum,
P, ultimate).

Furthermore, the compound of the present invention can be used in fields, paddy fields, orchards, tea plantations,
It can be used as an agricultural and horticultural fungicide for pastures, lawns, etc., and can be expected to increase its bactericidal efficacy by mixing it with other agricultural and horticultural fungicides. Furthermore, it can also be used in combination with insecticides, acaricides, nematicides, herbicides, plant growth regulators, and fertilizers.

<Effects of the Invention> The compounds of the present invention have excellent effects against plant diseases caused by various plant pathogenic bacteria, especially fungi such as downy mildew and late blight.
Furthermore, since it does not cause any phytotoxicity to cover plants, it can be used in a variety of applications as an active ingredient in agricultural and horticultural fungicides.

<Examples> The present invention will be explained in more detail below using production examples, formulation examples, and test examples, but the present invention is not limited to these examples.

First, a production example of the compound of the present invention will be shown.

Production Example 1 (Compound (1) of the Present Invention) To an anhydrous tetrahydrofuran solution [(60m) containing 2.721 imidazole (40 mmoA), 1.20 f (10 mmol) of thionyl chloride was added dropwise with stirring under water cooling. After the dropwise addition, the temperature was raised to room temperature, 1.571 (10 mmoAJ) of 2,4-dimethylthiazole-5-carboxylic acid was added, and the mixture was stirred at room temperature for 80 minutes.
4-dimethyl-5-(1-imidazolylcarbonyl)thiazole was used in the next reaction without being isolated. A solution of 1.461 (12 mmolJ) of 2-(2-furyl)aminoacetonitrile in anhydrous tetrahydrofuran was added dropwise to this solution under water cooling.

After dropping, the temperature was raised to room temperature and stirred for 1 hour. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
Crude crystals were obtained. By recrystallizing this with ethanol, colorless crystals of 2 (2,4-dimethylthiazole-5
-carboxyamino)-2-(2-furyl)acetonitrile2. I got Of. (yield 78% ml) 108-1
09°C Production Example 2 (Compound of the Invention (2)) 2-(8-furyl)aminoacetonitrile 1.461
(12mmo#)! : )! J-R-Chi #7 Z:
/1.20f (12rnrrIOl) in muchtitrahydrofuran solution! (80gR1) was added 2°4-dimethylthiazole-5-carbonyl chloride 1. while stirring under water cooling.
A tetrahydrofuran solution containing 751 (10 mmon) was added dropwise. After dropping, the temperature was raised to room temperature and stirred for 8 hours. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil.

This was subjected to silica gel column chromatography (elution a).
: n-hexane/ethyl acetate (271) to obtain 1.981 of colorless crystals of 2-(2,4-dimethylthiazole-5-carboxyamino)-2-(8-furyl)acetonitrile. (Yield 74%) mp 94-96°C Production Example 8 (Present Compound (8)) Thionyl chloride 1.2011 (10 mmol) was added to an anhydrous tetrahydrofuran solution (60 m) containing 2.72 f (40 mmol) of imidazole while stirring under water cooling. ) was added dropwise. After the dropwise addition, the temperature was raised to room temperature, 1.57 F of 2,4-dimethylthiazole-5-carboxylic acid (10 liters) was added to the mixture, and the mixture was stirred at room temperature for 80 minutes. This solution was cooled on ice again, and 2-(2-thienyl)aminoacetonitrile 1.
A solution containing 659 (12 mrnol) in anhydrous tetrahydrofuran was added dropwise. After dropping, the temperature was raised to room temperature and stirred for 1 hour. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil.

This was subjected to silica gel column chromatography (eluent:
n-hexane/ethyl acetate = 271) to obtain crude crystals. This was recrystallized from n-hexane/ethyl acetate to form colorless crystals of 2-(2,4-dimethylthiazole-
1.80f of 5-carboxyamino)-2-(2-thienyl)acetonitrile was obtained. (yield 65%) mp 1
27.5-128.5”C Production Example 4 (Compound of the present invention (4
)) 1.20 g (10 mmol) of thionyl chloride was added dropwise to an anhydrous tetrahydrofuran solution (60 m) containing 2.72 f (40 mm) of imidazole with stirring under ice cooling. After dropping, the temperature was raised to room temperature and 1.57 f (10 mmo, l) of 2,4-dimethylthiazole-5-carboxylic acid was added.
) was stirred at -degrees ic, tll, t at room temperature for 80 minutes. This solution was cooled on ice again, and 2-(8-thienyl)aminoacetonitrile 1.659 (12 mmoA
! ) in anhydrous tetrahydrofuran was added dropwise.

After dropping, the temperature was raised to room temperature and stirred for 1 hour. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and ethyl acetate was distilled off under reduced pressure.
An oil was obtained.

This was subjected to silica gel column chromatography (eluent:
Purified by n-hexane/ethyl acetate-2/1),
-(2,4-dimethylthiazole-5-carboxyamino)-2-(8-thienyl)acetonitrile 1.95g
I got it. (Yield 70%) nH2j i, 56701
H-Grudge δ (, CDC71s) 2.60 (6H, 8
), 6.22 (IH.

d, J=8Hz), 7.0-7.6 (4H, m) Production Example 5 (Compound (5) of the Present Invention) Ij Anhydrous tetrahydrofuran solution (60wIt) containing Taso-Jl/2.721 (4QmmoJ) thionyl chloride 1.20f (10mmoJ) while stirring under water cooling.
) was added dropwise. After dropping, the temperature was raised to room temperature and 2-methyl-4
-ethylthiazole-5-carboxylic acid 1.71 f (
10 mmo/) was added to the mixture at a temperature of 10 mm, and the mixture was stirred at room temperature for 80 minutes. This solution was cooled on ice again, and 1.461 (12 mmo#) of 2-(2-furyl)aminoacetonitrile was added.
Anhydrous (f) lahydrofuran solution was added dropwise. After dropping, the temperature was raised to room temperature and stirred for 1 hour. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil. This was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 271) to obtain crude crystals. This was recrystallized from n-hexane/ethyl acetate to give colorless crystals of 2-(2-methyl-4-ethyldeazole-5-carboxyamino)-2-(2-
1.58 fli of acetonitrile. (Yield 57
%) mp125-126°C Production Example 6 (Compound of the present invention (6
)) Imidazo-Jl/2.72 f (40mmo#)
Add 1.20 f of thionyl chloride (10 mmail) to an anhydrous tetrahydrofuran solution (60 m) containing thionyl chloride while stirring under water cooling.
) was added dropwise. After dropping, the temperature was raised to room temperature and 2-methyl-
4-ethylthiazole-5-carboxylic acid 1.71 f
(10mm0A') and stirred at room temperature for 30 minutes. This solution was cooled on ice again, and 1.65 f (12 mmo
d) A solution containing anhydrous tetrahydrofuran was added dropwise. After dropping, the temperature was raised to room temperature and stirred for 1 hour. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil. This was subjected to silica gel column chromatography (eluent: n-hexane/ethyl acetate = 2/1).
Purification was performed to obtain crude crystals. This was recrystallized from n-hexane/ethyl acetate to give colorless crystals of 2-(2-methyl-
4-ethylthiazole-5-carboxyamino)-2-
(2-thienyl)acetonitrile1. 'I got 14f.

(Yield 60%) mp 187-188°C Production Example 7 (Compound (7) of the Invention) Thionyl chloride 1.20 f (60 st) containing 2.72 f (40 mmol) of imidazole was added with stirring under water cooling. 10 mmo,/) was added dropwise. After dropping, the temperature was raised to room temperature and 2-methyl-4-n-
Propylthiazole-5-carboxylic acid 1.85 f (
10 mm0 A') was added to the mixture at a temperature of 100 mm, and the mixture was stirred at room temperature for 1 hour. This solution was cooled on ice again, and 1.65 f (12 mmol) of 2-(2-thienyl)aminoacetonitrile was added.
A solution of anhydrous tetrahydrofuran was added dropwise. At the dropping edge, the temperature was raised to room temperature and stirred for 8 hours. After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil. This was carried out using silica gel column chromatography (
Eluate: n-hexane/ethyl acetate = 2/1) to obtain crude crystals. This was recrystallized from n-hexane/ethyl acetate to give colorless crystals of 2-(2-methyl-4-n-
Propylthiazole-5-carboxyamino)-2-(
2-thienylcoacetonitrile 1.61F was obtained. (Yield 58%) mp125-126''C Production Example 8 (Compound of the Invention (9)) Thionyl chloride 1. 20f (10 mmol) was added dropwise. After the dropwise addition, the temperature was raised to room temperature and 1.85.1 (Bmm) of 2-methyl-4-isopropylthiazole-5-carboxylic acid
ol) was added to the mixture, and the mixture was stirred at room temperature for 1 hour. This solution was cooled on ice again and 2-(2-thienyl)amino7ce)-
)' Anhydrous tetrahydrofuran solution containing 1.65 f (12 mmog) was added dropwise. After dropping, the temperature was raised to room temperature and stirred for 3 hours.

After the reaction, tetrahydrofuran was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate, and then ethyl acetate was distilled off under reduced pressure to obtain an oil. This was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate-2/1), and 2-methyl-4-isopropylthiazole-5-carboxyamino)-2-(2
-Thienyl)acetonitrile 1.49y was obtained. (Yield 49%) Dove 7
y'i-taJ″dIH-NMRδ(CDCa)
t, 26 (6H, d, J=6Hz), 2.62 (3H
,s), 3.70 (LH,sep, J=6Hz
), 6.35 (LH, d, J=8Hz), 6
, 8-7.1 (4H, m) Table 1 shows some of the compounds of the present invention that can be produced by such a production method.

Table 1 Examples of formulations are shown below. Note that parts represent parts by weight.

Formulation Example 1 50 parts each of the compounds (1) to (14) of the present invention, 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide were thoroughly ground and mixed to hydrate each of the compounds of the present invention. agent can be obtained.

Formulation Example 2 25 parts each of the compounds (1) to (14) 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 of the active ingredient became 5 microns or less. By doing so, suspensions of each of the compounds of the present invention can be obtained.

Formulation Example 8 Powders of each of the compounds of the present invention can be obtained by thoroughly pulverizing and mixing 2 parts each of the compounds (1) to (14) of the present invention, 88 parts of kaolin clay, and 10 parts of talc.

Formulation Example 4 20 parts each of the compounds (1) to (14) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 60 parts of xylene
By thoroughly mixing these parts, emulsions of each of the compounds of the present invention can be obtained.

Formulation Example 5 2 parts each of the compounds (1) to (14) of the present invention, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, and water may be added. After kneading, granules of each compound of the present invention can be obtained by granulating and drying.

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

Table 2 The control efficacy (control rate) was calculated by the following method by observing the diseased state of the test plants at the time of investigation, that is, the bacterial flora on leaves, stems, etc., and the degree of lesions.

a: Plants (or leaves) with bacterial flora and lesions of 50% or more
Number b: 〃 〃 26-50% 〃〃〃c: 〃
〃 10~25% 〃〃〃d:tt tt
Approximately 10 parts 〃〃e: 〃 〃 Not observed at all 〃 〃Test Example 1 Potato late blight control test (preventive effect) A plastic pot was filled with sandy loam, potatoes (Danshaku) were sown, and grown in a greenhouse for 20 days. . Thereafter, the test drug prepared as a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and the solution was sprayed on the leaves so as to sufficiently adhere to the leaf surface. After spraying, a spore suspension of Potato Phytophthora was sprayed and inoculated. After inoculation, the seeds were placed in a dish at 20° C. and high humidity, and then grown for 5 days under lighting, and the pesticidal efficacy was investigated.

The results are shown in Table 8.

Test Example 2 Potato Phytophthora control test (therapeutic effect) A plastic pot was filled with sandy loam, potatoes were sown, and grown in a greenhouse for 40 days. Thereafter, a spore suspension of Potato Phytophthora was sprayed and inoculated. After vaccination,
After incubation at 20°C and high humidity, the test drug made into a hydrating powder according to Formulation Example 1 was diluted with water to a predetermined wave intensity, and sprayed on the foliage to ensure sufficient adhesion to the leaf surface. . After spraying, the plants were allowed to grow for 7 days under illumination, and the pesticidal efficacy was investigated. The results are shown in Table 8.

Test Example 8 Tomato Phytophthora control test (preventive effect) A plastic pot was filled with sandy loam, tomatoes (ponchirosa) were sown, and grown in a greenhouse for 20 days. To tomato seedlings that have developed their 2nd to 8th true leaves, dilute the test chemical prepared as a hydrating powder with water to a specified concentration according to Formulation Example 1, and spray it on the foliage so that it fully adheres to the leaf surface. did.

After spraying, a spore suspension of Phytophthora tomato was sprayed and inoculated.

After inoculation, the seeds were grown for one day at 20° C. under high humidity, and then grown for 5 days under lighting, and the pesticidal efficacy was investigated. The results are shown in the 8th section.
Show it on the table.

Test Example 4 Tomato Phytophthora control test (therapeutic effect) A plastic pot was filled with sandy loam, tomatoes (ponchirosa) were sown, and grown in a greenhouse for 50 days. A spore suspension of tomato Phytophthora blight was sprayed and inoculated onto the moving surface of the tomato plant where the 6th to 7th true leaves had developed. After inoculation, after incubating for one day at 20°C and in high humidity, dilute the test drug made into a wettable powder according to Formulation Example 1 with water to a specified concentration, and spread it on the stems and leaves so that it fully adheres to the leaf surface. Spread.

After spraying, the plants were allowed to grow for 5 days under illumination, and the pesticidal efficacy was investigated. The results are shown in Table 8.

Test Example 5 Grape Vine Disease Control Test (Preventive Effect) A plastic pot was filled with sandy loam, grapes were sown, and grown in a greenhouse for 50 days. Thereafter, the test drug made into a hydrating powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and then added to the sixth sample.
The foliar spray was applied to grape seedlings that had developed ~7 true leaves so that it would fully adhere to the leaf surface. After spraying, a spore suspension of grapevine and disease fungi was sprayed and inoculated. After inoculation, 1 at 20℃ and high humidity.
After growing for 8 days under illumination, the pesticidal efficacy was investigated. The results are shown in Table 8.

Test Example 6 Grapevine disease control test (therapeutic effect) A plastic pot was filled with sandy loam, grapes were sown, and grown in a greenhouse for 50 days. A spore suspension of grapevine and disease fungi was sprayed and inoculated onto young grape seedlings in which the 6th to 7th true leaves had developed.

After inoculation, after incubating for one day at 20°C and in high humidity, dilute the test drug made into a wettable powder according to Formulation Example 1 with water to a specified concentration, and spread it on the stems and leaves so that it fully adheres to the leaf surface. Spread. After spraying, the plants were allowed to grow for 8 days under illumination, and their control efficacy was investigated.

The results are shown in Table 8.

Test Example 7 Cucumber and disease control test (preventive effect) A plastic pot was filled with sandy loam, and cucumbers (Sumo Hanshiro) were sown and grown in a greenhouse for 14 days. Then, Formulation Example 1
A test chemical prepared as a wettable powder was diluted with water to a predetermined concentration according to the above method, and the solution was sprayed on grass leaves so that it would sufficiently adhere to the leaf surface.

After spraying, a spore suspension of cucumber and disease bacteria was sprayed and inoculated. After inoculation, the seeds were grown for 1 day under humid conditions of 20"C1, and then grown for 5 days under illumination, and the pesticidal efficacy was investigated.

The results are shown in Table 8.

Test Example 8 Cucumber and disease control test (therapeutic effect) A plastic pot was filled with sandy loam, and cucumbers (Sumo half day) were sown and grown in a greenhouse for 14 days. Cucumbers at the cotyledon stage were sprayed and inoculated with a spore suspension of cucumber and disease fungi. After inoculation, after one day at 20℃ and high humidity, the test drug made into a wettable powder according to Formulation Example 1 was diluted with water to a predetermined concentration.
It was sprayed on the foliage so that it adhered sufficiently to the leaf surface. After spraying, the plants were allowed to grow for 8 days under illumination, and their control efficacy was investigated.

The results are shown in Table 8.

Test Example 9 Tomato Phytophthora control test (osmotic transfer effect) A plastic pot was filled with sandy loam, tomatoes (Ponchirosa) were sown, and grown in a greenhouse for 20 days. A test chemical prepared as a suspension according to Formulation Example 2 was diluted with water and a predetermined amount of the solution was sprinkled onto the soil of tomato seedlings in which the 2nd to 8th true leaves had developed. After irrigation, the plants were grown in a greenhouse for one day and then sprayed and inoculated with a spore suspension of tomato fungi.

After inoculation, the seeds were incubated for 1 day at 20° C. under high humidity, and then grown for 5 days under light to investigate their pesticidal efficacy. The result is the fourth
Show it on the table.

Table 4 Test Example 10 Chemical damage test A test drug made into a wettable powder according to Formulation Example 1 on young grapes, tomatoes (Ponchirosa), and cucumbers (Sumo Hanpaku) was diluted with water to a specified concentration, and was sprayed on the foliage so that it adhered sufficiently to the foliage. After spraying, the seeds were grown in a greenhouse for two weeks, and the degree of chemical damage was investigated. The results are shown in Table 5.

Plant damage was evaluated by visual observation of the degree of growth of the test plants from the time of spraying to the time of investigation, using a six-level scale of 0, 1, 2, 8, and 4°5.

"5": Severe chemical damage and no growth is observed. "0": No chemical damage is observed.

Table 5 (41 completed)

Claims (6)

[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 or a lower alkyl group having 1 to 3 carbon atoms, and R^1 represents a 2-furyl group, 3-furyl group, 2-thienyl group or 3-thienyl group. ] An amide derivative represented by. (2) R^1 is a methyl group, R^2 is a methyl group or ethyl group, and R^3 is a 2-thienyl group or 3-
The amide derivative according to item 1, which is a thienyl group. (3) The amide derivative according to item 1, wherein R^1 is a methyl group, R^2 is an ethyl group, and R^3 is a 2-thienyl group or a 3-thienyl group. (4) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, and X is a halogen represents an atom. ] There are acid halides represented by the general formula ▲ numerical formulas, chemical formulas, tables, etc. 2. The method for producing an amide derivative according to item 1, which comprises reacting the aminonitrile derivative or its salt represented by the following. (5) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R^1 and R^2 are the same or different and represent a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms. [In the formula, R^1 and R^2 have the same meanings as above. . ] Obtain an acylimidazole compound represented by the general formula ▲ Numerical formula, chemical formula, table, etc. represents a group. ] The method for producing an amide derivative according to item 1, which comprises reacting with the aminonitrile derivative or a salt thereof. (6) A fungicide for agriculture and horticulture, which contains the amide derivative described in item 1 as an active ingredient.