JPH0245457A - Amide derivative, production thereof and plant disease injury controlling agent containing said derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R1 is 3-5C alkyl or 3-5C alkenyl; R2 is methylthio, methylsulfinyl, nitro, etc.; X and Y are H or chloro; Z is chloro, bromo or tritluoromethyl). EXAMPLE:N-[1-(4-Bromophenyl)ethyl]-3,3-dimethyl-2-methylthio-pentenamide. USE:A plant disease injury controlling agent having excellent foliar preventive and systemic translocating disease injury controlling effects especially on blast of rice plant. PREPARATION:An alpha-methylbenzylamine derivative expressed by formula II is reacted with a carboxylic acid expressed by formula III or a reactive derivative thereof (e.g., acid anhydride or chloride) to provide the compound expressed by formula I. The reaction is carried out by using, as necessary, a reaction assistant, such as dicyclohexylcarbodiimide.

Description

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

<Conventional technology> Various plant disease control agents have been developed so far.
It is unfortunate that we cannot necessarily be fully satisfied in terms of effectiveness, etc.

<Problems to be Solved by the Invention> The purpose of the present invention is to develop a compound having excellent control efficacy against plant diseases.

Means for Solving the Problem> In order to achieve the above object, the present inventors have made extensive studies and found that - ritual [wherein R1 is an alkyl group having 8 to 6 carbon atoms or an alkyl group having 8 to 6 carbon atoms] 8-5 alkenyl group, R1 is a methylthio group, methylsulfinyl group, mesyl group, nitro group, methoxy group, methoxycarbonyl group, carbamoyl group, N-
Represents methyl carbamoyl group or hydroxy group 1X
and Y are the same or different and represent a hydrogen atom or a chloro atom, and 2 represents a chloro atom, a bromo atom or a trifluoromethyl group. ] (hereinafter referred to as the compound of the present invention).

) was found to have particularly biased foliage preventive disease control efficacy and systemic disease control efficacy against rice blast disease, leading to the present invention.

The compound of the present invention is particularly suitable for rice potato fli (Pyricu-
1aria oryzae) lc, but other plant diseases that can also be controlled include Cochliobolus leaf blight (Cochliobolus
m1ya-beanus), apple scab disease (Ve
nturia 1nae-qualis), pear scab (Venturia nashicola), persimmon scab (Gloeosporium kaki),
Anthracnose disease of cucurbits (CCo11etotrichu l)
agenarium), bean anthracnose (Colle
totrichum lindemuthianum
), groundnut black astringency (Mycosphaerell)
apersonatum), brown spot disease (Cercospo
ra arachidi-cola), Colletotrichum tabacum,
Cercosporabetico
la), etc.

Next, the method for producing the compound of the present invention will be explained in detail.

For the compound of the present invention represented by the general formula [1], the following manufacturing methods Φ to 0 may be mentioned depending on the type of R3.

Production method (1) [In the formula, x, Y and Z have the same meanings as above. ] An α-methylbenzylamine derivative represented by the general formula % [[] [wherein R1 represents the same meaning as above, and R8 represents a methylthio group, a methylsulfinyl group, a mesyl group, a nitro group, a methoxy or methoxycarbonyl group. ] with the carboxylic acid or its reactive derivative,
It can be obtained by reacting in the presence of a reaction aid if necessary.

In the above reaction, the carboxylic acid represented by -mathematical cap] or its reactive derivative includes the corresponding carboxylic acid, acid anhydride, acid chloride, acid bromide, carboxylic acid methyl ester, carboxylic acid ethyl ester, etc. Examples of reaction aids include dicyclohexycarbodiyl, 1-ethyl-8-(8- dimethylaminopropyl) carbodiimide hydrochloride, 1.1'-carbonyldiimidazole,
Phosphorus pentachloride, phosphorus trichloride, phosphorus oxychloride, thionyl chloride, phosgene, sodium hydroxide, potassium hydroxide, sodium methylate, sodium ethylate, triethylamine, pyridine, quinoline N.

N-dimethylaniline, N, N-diethylaniline, N
-Methylmorpholine and the like.

In the above reaction, the reaction temperature is typically 0 to 200°
The C1 reaction time is 0.1 to 24 hours, and the amount of reagent used for the reaction is based on 1 mole of the carboxylic acid represented by the general formula [1] or its reactive derivative.
The α-methylbenzylamine derivative represented by 1 to 1
．． 2 mol, and the reaction aid is 1 mmol to 1.5 mol.

In the above reaction, although a reaction solvent is not necessarily required, it is generally carried out in the presence of a solvent.

Usable solvents include aliphatic hydrocarbons such as hexane, heptane, and ligroin, aromatic hydrocarbons such as benzene, toluene, and xylene, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane,
Ethers such as diethylene glycol dimethyl ether, dichloromethane, chloroform, carbon tetrachloride, 1.2
Examples include halogen atom-containing solvents such as dichloroethane and chlorobenzene, solvents such as dimethylformamide, dimethylsulfoxide, acetonitrile, and water, and mixtures thereof.

After completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as filtration, extraction, concentration, etc., and subjecting it to operations such as column chromatography and recrystallization, if necessary. The α-methylbenzylamide derivative represented by the general formula [13], which is one of the raw material compounds for producing the compound of the present invention, is, for example, an organic
Reactions, Mo1. L 801-880
(1949), the other raw material compound, the general formula (1
The carboxylic acid represented by 1 or its reactive derivative is
For example, J, Am, Chetr+, Soc,, 1
02, 2125 (1980), J. Am. Chem.
Soc, 79, 2507 (1957), Ch.
Em, Ber, 119, 1196 (1986) and conventional derivatization methods, i.e., hydrolyzing a carboxylic acid ester to obtain a carboxylic acid, converting the obtained carboxylic acid into an acid halide to obtain a carboxylic acid. It can be synthesized by a method of obtaining a halide.

Manufacturing method ■ general formula [In the formula, X, Y and 2 represent the same meanings as above. ] It can be synthesized from the compounds shown below.

[In the formula, R□, X%Y and Z have the same meanings as above. ]

α-Bromoacetylamide derivative and general formula represented by %formula%[] [In the formula, R4 represents a methylthio group or a nitro group.

] It can be obtained by reacting with the nucleophilic reactant shown in the following in the presence of a reaction aid if necessary. Examples of reaction aids include phloroglucinol.

In the above reaction, the reaction temperature is typically O~200″
C1 reaction time is 1 to 240 hours, and the amount of reagent used for the reaction is 1 mole of α-bromoacetic acid derivative:
- The nucleophilic reactant of formula (V) is from 1 to 10 mol, and the reaction aid is from 1 mmol to 5 mol.

The above reaction is generally carried out in the presence of a solvent.

Examples of solvents that can be used include dimethylformamide,
Examples include dimethyl sulfoxide.

After completion of the reaction, the desired compound of the present invention can be obtained by carrying out usual post-treatments such as filtration, extraction, and concentration, and subjecting it to operations such as 01 column chromatography and recrystallization as necessary. In addition, α-bromoacetamide represented by the general formula (IYI), which is a raw material compound for producing the compound of the present invention, is represented by, for example, J, Pe5ticideSci,
, 12, 79-84 (1987).

Manufacturing method ■ i Ritual [In the formula, R,, X, Y and 2 have the same meanings as above. ] It can be obtained by oxidizing the α-methylthioacetate derivative shown. Examples of oxidizing agents that can be used include m-chloroperbenzoic acid.

In the above reaction, the reaction temperature is typically O~100°
The C1 reaction time is 1 to 24 hours, and the amount of the oxidizing agent used in the reaction is 1 to 3 moles per mole of the α-methylthioacetamide derivative.

After completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as filtration, extraction, concentration, etc., and subjecting it to operations such as column chromatography and recrystallization, if necessary. Note that the α-methylthioacetate derivative represented by the general formula [Vll, which is a raw material compound for producing the compound of the present invention, is included in the compound of the present invention and can be obtained by the production method or (2).

Manufacturing method■ In general formula 1, R6 represents a methoxycarbonyl group, and X1Y
and Z have the same meanings as above. ] An amide 3 conductor represented by the general formula % formula % [] [wherein R'1 represents a primary or secondary alkyl group having 8 to 5 carbon atoms or an alkenyl group having 8 to 5 carbon atoms, and L
represents a leaving group represented by a chloro atom, a bromo atom, an iodo atom, or a methanesulfonyloxy group or a p-)luenesulfonyloxy group. ] It can be obtained by reacting the alkylating agent or alkenylating agent shown in the following in the presence of a reaction aid if necessary.

Examples of reaction aids include bases such as sodium hydride.

In the above reaction, the reaction temperature is typically 0 to 100°C.
, the reaction time is 1 to 24 hours, and the amount of reagents used for the reaction is - Amide derivative 1 shown in the formula [VII]
Per mole, the alkylating or alkenylating agent, denoted by formula [Vll, is 1,1 to 2 mol, and the reaction aid is 1 mmol to 5 mol.

Examples of solvents that can be used in the above reaction include dimethylformamide.

After completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as filtration, extraction, concentration, etc., and subjecting it to operations such as column chromatography and recrystallization, if necessary. In addition, when producing the compound of the present invention, one of the raw material compounds is the general formula (denoted by Vll [in the formula,
x and ylz have the same meanings as above. ] α-Methylbenzylamine derivative shown and CH30
It can be obtained by reacting with 0C-CR2-COOH or its reactive derivative or diketene.

Manufacturing method ■ General formula [wherein R1, X%Y and 2 represent the same meanings as above. ] A carboxylic acid or a reactive derivative thereof represented by the general formula %) [wherein R7 represents a hydrogen atom or a methyl group]. ] It can be obtained by reacting the amine shown in the following in the presence of a reaction aid if necessary. Examples of reaction aids that can be used include 1,1'-carbonylsiimidazole.

In the above reaction, the reaction temperature is typically 0 to 100°.
The C1 reaction time is 1 to 240 hours.For the general formula R, the amine derivative represented by the -ritual [X] is
The amount of the reaction aid is 1 to 50 mol, and the amount of the reaction aid is 1 to 2 mol. Examples of solvents that can be used include tetrahydrofuran and dimethylformamide.

After completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as filtration, extraction, concentration, etc., and subjecting it to operations such as column chromatography and recrystallization, if necessary. In addition, the carboxylic acid represented by the general formula [IX] which is one of the raw material compounds for producing the compound of the present invention is a compound of the present invention represented by the formula [11], in which R2 is a methoxycarbonyl group. It can be obtained from compounds.

Production method (1) [In the formula, xlY and Z have the same meanings as above. ] Incyanide derivatives represented by the formula % and 2 represented by the general formula % ([wherein R1 represents the same meaning as above]
It can be obtained by reacting the compound with a 'rudehyde derivative in the presence of a reaction aid if necessary. Examples of reaction aids include sulfuric acid.

In the above reaction, the reaction temperature is typically 0 to 50°C.
One reaction time is o, i ~ 24 hours, and the amount of reagents used for the reaction is -1 mole of the incyanide derivative shown in the -ritual [XI], and the aldehyde derivative shown in the -ritual [■] , 1 to 50 mol, and the reaction aid is 1 mmol to 5 mol.

Examples of solvents that can be used include water.

After completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as filtration, extraction, concentration, etc., and subjecting it to operations such as column chromatography and recrystallization, if necessary. The isocyanide derivative represented by the general formula [XI], which is one of the raw material compounds for producing the cough compound of the present invention, is, for example, Angew.

Chem-Int, Ed-10 #182 (1971), the general formula [wherein, X, Y and Z represent the same meanings as above] is obtained. ] It can be synthesized from the compounds shown in the following.

When using the compounds of the present invention that can be obtained by the above production methods ① to ① as an active ingredient of a plant disease control agent, they may be used as they are without adding any other ingredients, but usually solid carriers, liquid It is used by mixing with carriers, surfactants, and other formulation auxiliaries to formulate emulsions, wettable powders, suspensions, granules, powders, etc.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99%, preferably 0.2 to 95%.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, corn husk 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, isophorone-derived ketones, soybean oil, cottonseed oil, etc. Examples include vegetable oil, dimethyl sulfoxide, acetonitrile, water, etc.

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 polyoxybrobylene block copolymers Examples include nonionic surfactants such as sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester.

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

These preparations can be used as is, or diluted with water and sprayed on foliage or on the soil. ! I) ζ Sprinkle, sprinkle and mix, or apply to soil. Furthermore, by mixing it with other plant disease control agents, it can be expected that the control efficacy will be enhanced.

Furthermore, it can be used in combination with insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, and the like.

When the compound of the present invention is used as an active ingredient of a plant disease control agent, the treated fleas may be affected by climatic conditions, formulation form, treatment timing,
Although it varies depending on the method, location, target disease, logarithmic crop, etc., it is usually 0.05 to 200 f per are, preferably 0.1 to 100 y, and emulsions, wettable powders, suspensions, etc. When applied diluted, the application concentration is 0.00
005-0.5% preferably 0.0001-0.2'
/S, and granules, powders, etc. are applied as they are without any dilution.

<Effects of the Invention> The compound of the present invention has excellent effects against plant diseases caused by various plant pathogens including rice blast, and therefore can be used in various applications as an active ingredient of plant disease control agents.

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

First, a manufacturing example will be shown.

Production Example 1 (Compound (15), Production Method ■) 1-(4-bromophenyl)ethylamine 0,60 t (8 mmo
l) and triethylamine 0,87 f (8,6 mm
ol) All anhydrous x-te,! L/R: m Cooled on ice. 8.8-Dimethyl-2-methylthio-4-pentenoyl chloride was added dropwise to this while stirring. A water cooling bath was taken, and the mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were added to separate the layers, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain crude product 1.111. This was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate = 8:1) to obtain compound (15), that is, N-(1-(4-bromophenyl)ethyl]-8,8-dimethyl-2 -Methylthio-4-bentenamito o,sop was obtained.

mp 100-104℃' H-NMR (CDC1,/TMS, δ(pI)m
)).

0.9-1.7 (m, 9H) 1.90 and 2.08 (each S1 total 8H).

3.08 and 8.10 (each S9 combined IH).

4.65~5.85 (m, 8H) j5.6~6
．． 2 (m, LH) #6.75 (br d, LH).

6.95-7.6 (m, 4H) Production Example 2 (Compound (1), Production Method ■) N-[1-(4
-Chlorophenyl)ethyl]-2-bromo8.8-Dimethylbutanamide 6,65 F (20 mmol) was dissolved in 80 ml of dichlorophenylform, and a 16% aqueous solution of methyl mercaptan sodium salt 28 F (60
mmol) and heated at a bath temperature of 180 to 140°C for 8 hours. After cooling, add water and extract with ethyl acetate.
The ethyl acetate layer was washed twice with brine. After drying over anhydrous magnesium sulfate, the mixture was subjected to 3-of-3 drying to obtain 6.899 of a crude product. This was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate 5:1), and the
Compound (1) of No. 1, ie, N-(1-[4-chlorophenyl)ethyl]-2-methylthio-8°8-dimethylbutanamide, was obtained.

mpH7-119℃'H-NMR (CDC113/'I'MS, δ
(1) 1) Irl)) 1.00 and 1.06 (each S9 combined 9H).

1.46 (d, J=7Hz, 8H) 1.88 and 2.01 (each S, 8H in total)
.

2.98.8.01 (each S2 together with IH).

4.75~5.80 (m, IH) *6.55~
7.0 (brd, IH).

7.0-7.26 (m, IH).

Mass spectrum (m/e, 70eV) 299 (1'vI+), 253,248,288,19
6゜154.189,117,105. IOR production example 8
(Compound (3), production method ■) N-(1-(4-chlorophenyl)ethyl]-2-methylthio-8,8-dimethylbutanamide 0.6 Of (2 mmol) 'y
It was dissolved in 20 ml of A, and 1.08 (4.4 mmol) of m-dichloroperbenzoic acid was added little by little to this solution. After stirring at room temperature for 1 hour, deuterated water was added, extracted with chloroform, washed with brine, and concentrated to obtain 0.92N of a crude product. This was subjected to preparative thin chromatography (elution solvent; hexane: iii at ethyl =
2:1) to obtain 0,849 compound (8
) i.e. N-El -(4-chlorophenyl)ethyl]-
2-methylsulfonyl-8,8-dimethylbutanamide was obtained.

mp 140-145°C IH-NMR (CDC, g, /TMS, δ(1)Pm)
) 1.20 and 1.28 (each 80 total 9H
).

1.45 (d − J = 7 Hz e 8 H) −
2,95 (s, 8H).

8.54 and 8.58 (8*IH) s4.70-5.
f30 (m, IH).

6.95-7.40 (m, 511) Production Example 4 (
Compound (10), Production method ■) 1.02f (4 mmol) of N-(1-(4-chlorophenyl)ethyl]-2-(methoxycarbonyl)acetamide was anhydrous.
The mixture was dissolved in 5 d of Xh k A7 solution and cooled on ice. Under a nitrogen atmosphere, 0.17 f (4.2 mmol) of sodium hydride (60% oil desparate bottle) was added little by little, and the mixture was stirred for 80 minutes under water cooling. To this was added 0.581 (4.2 mmol) of 5ee-butyl bromide, and the mixture was stirred for 80 minutes under water cooling, and further stirred for 1 hour at room temperature.

Water was added 1, extracted with ethyl acetate, and washed twice with brine. The residue obtained by concentrating the methyl acetate layer was further separated between hexane and acetonitrile, and the acetonitrile layer was concentrated to obtain a crude product of 0.882. This was subjected to silica gel column chromatography (elution solvent; hexane: ethyl acetate = 8
: 1) to give 0.64 f of the compound (1
0) i.e. N-[1-(4-chlorophenyl)ethyl]-
8-Methyl-2-(methoxycarbonyl)pentana [
I got a de.

mp 76-78°C sH-NMR (CD (J3/TMS, δ(1)pm))
0.6-2.4 (m, 12H).

2.85-8.25 (m, IH).

8.67 (s, 8H).

4.7-5.8 (m, tH)s 6.75-7.85 (m, 5H) Production Example 6 (Compound (18), Production Method ■) N-[1-(
4-chlorophenyl)ethyl]-8-methyl-2-(methoxycarbonyl)butanamide 0.80 f (1 m
mol) was dissolved in 8 ttl of DMF, 8 at of a 40% aqueous solution of methylamine was added, and the mixture was stirred at room temperature for 5 days. Water was added, the resulting white sediment was collected by filtration, washed with water and then with a small amount of cold ethanol, and compound (18), that is, N-(1-(
0.15' of 4-chlorophenyl)ethyl]-8-methyl-2-(methylaminocarbonyl)butanamide was obtained.

mp 221-224℃'H-NMR (DMSO-d, /TMS, δ(1)1)
m)) 0.6-1.1 (m, 6H).

1.88 (d, J=7Hz, 8H).

1.7-2.4 (m, IH).

2.6-2.95 (m, IH).

8.29 (s, 8H).

4.5-5.2 (m, IH).

? , i ~ q, 96 (me 5H) *8.05~
8.55 (m, I H) mass spectrum (m/e,
70eV) 2.96 (M+), 281,268,288,224゜222.154,149 Production Example 6 (Compounds (8) and (9), !!!Preparation method ■
) 1-(4-chlorophenyl)ethyl isocyanide 0.
88 f (5 mmol) in 5 ml of hyalaltehyde
and cooled on ice. To this, 0.52 f concentrated sulfuric acid (
A solution of 5 mmol) dissolved in 5 ml of water was added dropwise. After stirring at room temperature for 1 hour, the ethyl acetate was washed with aqueous potassium carbonate solution, and then with brine. After drying with anhydrous sodium sulfate, it was concentrated to obtain a crude product of 1.48
I got f. This was subjected to silica gel chromatography. By elution with a mixed solvent of hexane:ethyl acetate=8:1, 0.47% of compound (8), that is, N-[
1-(4-chlorophenyl)ethyl]-2-hydroxy-8°8-dimethylbutanamide was obtained.

mp, 102°C 'H-NMR (TMS, 'CDCl3.δ (ppm))
0.94 (8,9H), 1.41 (d, J=7
H2, aH) e8.25-8.75 (m, 2H),
4.7-5.8 (m, IH).

6.5-6.85 (m, IH), 7.0-7.4
(m, 4H) Furthermore, hexane: ethyl acetate = 1; 1
Compound (9) of 0.45F was obtained by elution with a mixed solvent of .

mp159℃'H-NMR (7MS/CDC1, δ(1)rim))
0.98(8,tH)e 1.45(d, J=7Hz.

8H), 8.8-8.8 (m, 2H), 4.7
5-5.85 (m, IH), 6.5-6.9 (m
, tH), 7.0-7,4 (m I 4 H) Next, formulation examples are shown. The compounds of the present invention are indicated by compound numbers in Table 1. Parts represent parts by weight.

Formulation Example 1 60 parts each of the compounds (1) to (18) of the present invention, 8 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide were thoroughly ground and mixed to form a hydrating agent for each of the compounds of the present invention. get.

Formulation Example 2 26 parts each of the compounds (1) to (18) 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 6 microns or less. A suspension of each of the compounds of the present invention is obtained.

Formulation Example 8 2 parts each of the compounds (1) to (18) of the present invention, 88 parts of kaolin clay, and 10 parts of talc were ground and mixed to obtain a powder for each of the compounds of the present invention.

Formulation Example 4 20 parts each of the compounds (1) to (18) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 60 parts of xylene
Mix well to form an emulsion of each compound of the present invention.

Formulation Example 6 2 parts each of the compounds (1) to (18) 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 are thoroughly ground and mixed, and water may be added. After kneading, the mixture is granulated and dried to obtain granules of each compound of the present invention.

Next, test examples demonstrate that the compounds of the present invention are useful as plant disease control agents. 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 The control efficacy is determined by visually observing the disease 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, the rating is ``5''; If around 10 copies are accepted, it will be ``4'', if around 80 copies are accepted, it will be ``8J'', if around 50 copies are accepted, it will be ``-24'', and if around 70 copies are accepted, it will be ``1''.
'', and if there is no difference from the disease onset state when no compound is tested, it is evaluated as rOJ and evaluated on a 6-level scale, and indicated as 5.4.8.2.1 and O, respectively.

Test Example 1 Rice blast control test (preventive effect) A plastic pot was filled with sandy loam soil, sown with rice (Kinki No. 88), and grown in a greenhouse for 20 days. A test chemical prepared as a hydrating powder according to Formulation Example 1 was diluted with water to a predetermined concentration, and sprayed on rice seedlings so as to sufficiently adhere to the leaf surface. After spraying, the plants were sprayed with an air-dried spore suspension of the blast fungus and inoculated. After inoculation, the plants were grown for 4 days at 28° C. in darkness and high humidity, and their control efficacy was investigated. The results are shown in Table @8.

After weighing gK8 for 4 days, the control efficacy was investigated. The result is the fourth
Shown in the table.

Test Example 2 Rice blast control test (osmotic transfer effect) A plastic pot was filled with sandy loam, and rice (Kinki No. 88) was sown and grown in a greenhouse for 14 days. A test drug prepared as an emulsion according to Formulation Example 4 was diluted with water and a predetermined amount of the drug was sprinkled onto the soil of rice seedlings. After irrigation, the plants were grown in a greenhouse, and a spore suspension of the blast fungus was sprayed and inoculated. After inoculation, inside Sumitomo Chemical Co., Ltd., 4-2-1 Ichitakaji, at 28°C, in darkness and high humidity.

Claims (9)

[Claims] (1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents an alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, and R_2 represents a methylthio group, methylsulfinyl group, mesyl group, nitro group,
represents a methoxy group, methoxycarbonyl group, carbamoyl group, N-methylcarbamoyl group or hydroxy group, X and Y are the same or different and represent a hydrogen atom or a chloro atom, and Z is a chloro atom, a bromo atom or a trifluoro atom; Represents a methyl group. ] An amide derivative represented by. (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom, or a trifluoromethyl group. . ] α-Methylbenzylamine derivatives represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. R_3 is a methylthio group, a methylsulfinyl group, a mesyl group, a nitro group,
Represents a methoxy group or a methoxycarbonyl group. ] A general formula characterized by reacting with a carboxylic acid or its reactive derivative represented by ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1, R_3, X, Y and Z have the same meanings as above. represents. ] A method for producing an amide derivative represented by. (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents an alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, and X and Y are the same or different. Differently, represents a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom or a trifluoromethyl group. ] An α-bromoacetamide derivative represented by the general formula NaR_4 [wherein R_4 represents a methylthio group or a nitro group. [In the formula, R_1, R_4, X, Y and Z have the same meanings as above. ] A method for producing an amide derivative represented by. (4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents an alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, X and Y are the same or different, It represents a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom or a trifluoromethyl group. ] There are general formulas, mathematical formulas, chemical formulas, tables, etc. that are characterized by the oxidation of the amide derivative represented by or mesyl group. ] A method for producing an amide derivative represented by. (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_6 represents a methoxycarbonyl group,
and Y are the same or different and represent a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom or a trifluoromethyl group. ] An amide derivative represented by the general formula R'_1-L [wherein R'_1 represents a primary or secondary alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms,
L represents a chloro atom, a bromo atom, an iodo atom, or a leaving group such as a methanesulfonyloxy group or a p-toluenesulfonyloxy group. ] A general formula characterized by reacting with an alkylating agent or an alkenylating agent represented by ▲ There are mathematical formulas, chemical formulas, tables, etc. express the same meaning. ] A method for producing an amide derivative represented by. (6) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 represents an alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, and X and Y are the same or different, It represents a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom, or a trifluoromethyl group. ] A carboxylic acid or its reactive derivative represented by the general formula R_7-NH_2 [wherein R_7 represents a hydrogen atom or a methyl group. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the amine shown by ▼ [In the formula, R_1, Represents a carbamoyl group or a carbamoyl group. ] A method for producing an amide derivative represented by. (7) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a hydrogen atom or a chloro atom, and Z represents a chloro atom, a bromo atom, or a trifluoromethyl group. . ] An isocyanide derivative represented by the general formula R_1-CHO [In the formula, R_1 represents an alkyl group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms. [In the formula, R_1, X, Y and Z have the same meanings as above. ] A method for producing an amide derivative represented by. (8) A plant disease control agent containing the amide derivative according to claim 1 as an active ingredient. (9) A rice blast control agent containing the amide derivative according to claim 1 as an active ingredient.