JPH0276845A - Cyanoacetmide derivative, production thereof and plant disease injury controlling agent containing the same as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula l (R is 2-6C primary or secondary alkyl, 4-6C cycloalkyl, 2,6-dimethylpropyl, 3-6C alkenyl and alkynyl; X and Y are H, F or Cl; Z is H, halogen, CF3, lower fluoroalkoxy, cyano, nitro, CH3, OCH3 or SCH3). EXAMPLE:N-[1-(4-Chlorophenyl)ethyl]-2-cyano-3,3-dimethyl-pentenamide. USE:An active ingredient of plant disease injury controlling agents, having excellent foliar preventive disease injury controlling effects and systemic translocating disease injury controlling effects on plant disease injuries caused by various plant disease injury germs and especially useful for controlling blast of rice plant. PREPARATION:For example, an alpha-methylbenzylamine derivative expressed by formula II is reacted with an alpha-substituted cyanoacetic acid expressed by formula III or a reactive derivative thereof, as necessary, in the presence of a solvent and a reaction assistant, such as 1,1'-carbonyldiimidazole, to afford the compound expressed by formula I.

Description

[Detailed Description of the Invention] <Industrial Application Field> The present invention relates to a cyanoacetamide derivative, a method for producing the same, and a plant disease control agent containing the same as an active ingredient. Plant disease control agents have been developed, but
It is difficult to say that it is necessarily fully satisfactory in terms of efficacy, etc.

<Problems to be Solved by the Invention> The present invention aims to develop a compound that exhibits excellent control efficacy against plant diseases. Means for Solving the Problems> The present inventors have In order to achieve the above objective, as a result of intensive studies, we found that the general formula , 2.2-
represents a dimethylpropyl group or an alkenyl group or alkynyl group having 8 to 1 carbon atoms; X and Y are the same or different and represent a hydrogen atom, a fluorine atom, or a chlorine atom; A cyanoacetamide derivative (hereinafter referred to as the compound of the present invention) represented by ] representing a methyl group, a lower fluoroalkoxy group, a cyano group, a nitro group, a methyl group, a methoxyle group, or a methylthio group (hereinafter referred to as the compound of the present invention) is an excellent foliage preventive and disease control agent. The present inventors have discovered that this compound has efficacy and systemic disease control efficacy, and have arrived at the present invention.

The compound of the present invention is particularly useful for rice blast disease (Pyri-c).
ularia oryzae), but other plant diseases that can be controlled include rice sesame leaf blight (Cochl 1obolus m1y).
abean-us), apple black mania (Venturi)
a 1naequalia), Nashinokuroya disease (Vent
uria naahicola), oyster carbonaceous disease (Gl
oaosporium kaki), cucurbit anthracnose (
Colletotrichum lagenarium
), kidney bean anthracnose (Colletotrich
um lindemuthianum), groundnut black bitter disease (tviycosphaerel la per
so-natum), Q spot (Cercospora
arachidicola), tobacco anthracnose (Co
lletotrichum tabacum),? 4M disease (Cercospora beti)
cola) etc. are preferably represented by the general formula [wherein X and Y represent the same meanings as above, and R' is a secondary alkyl group having 8 to 6 carbon atoms or a
represents a secondary or tertiary methyl group or a lower fluoroalkoxy group. ] It is a cyanoacetamide derivative represented by the following.

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

The compound of the present invention comprises an a-methylbenzylamine derivative represented by the general formula [wherein X, Y and 2 have the same meanings as above] and a general formula [wherein R has the same meanings as above] ] denoted by α
- Substituted cyanoacetic acid or a reactive derivative thereof can be reacted with ξ in the presence of a reaction aid if necessary.

In the above reaction, the a-substituted cyanoacetic acid represented by the general formula [厘] or its reactive derivative includes the corresponding carboxylic acid, acid anhydride, acid chloride, acid bromide, carboxylic acid methyl ester, and carboxylic acid ethyl ester. Examples of reaction aids include dilechlorohexylcarbodiimide, l-ethyl-8 -(8-dimethylaminopropyl)carbodiimide hydrochloride, 1.1''-carbonyl dihydrochloride, phosphorus pentachloride, phosphorus trichloride, phosphorus chloride, 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°C.
, the reaction time is 0.1 to 24 hours, and the amount of reagents used for the reaction is as follows: per mole of α-substituted cyanoacetic acid or its reactive derivative represented by the general formula [臘]
The α-methylbenzylamine derivative represented by 1
~1.2 mol, and the reaction aid is 12 lmol ~ 5 mol.

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

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 the completion of the reaction, the desired compound of the present invention can be obtained by performing usual post-treatments such as extraction, concentration, and filtration, and, if necessary, subjecting it to column chromatography and re-purification. , the α-methylbenzylamine derivative represented by the formula [厘], which is one of the raw material compounds in the production of the compound of the present invention, is, for example, an organic
Rea-ctions, Mo1.5.801-88
0 (1949), X, Y and Z in the general formula C have the same meanings as above. ] It can be synthesized from the compounds shown in the following.

Also, the other raw material compound, α represented by the one-part formula [Zen]
-substituted cyanoacetic acid or its reactive derivative, for example J
*AmaChem, Soc*, 664886 (194
4), J, Organomet, Chem*,
285 +895 (1985) or J m Am, C
hem, 5acs.

108.1089 (1986) and the usual derivatization method, that is, hydrolyzing a carboxylic acid ester to obtain a carboxylic acid, and converting the obtained carboxylic acid into an acid halide to obtain a carboxylic acid halide. It can be synthesized by various methods.

Further, among the compounds of the present invention, in general formula (1), R is a primary or secondary alkyl group, or a primary or secondary alkyl group.
Compounds representing a class alkenyl group, a primary or secondary alkynyl group, or a cycloalkyl group are represented by the general formula [wherein, X, Y and Z have the same meanings as above. ] Cyanoacetamide derivatives represented by the general formula % formula % ([wherein R' is a primary or secondary alkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, 3 to 6 primary or secondary alkenyl groups, 3 carbon atoms
~6 primary or 112nd-class alkynyl groups,
L represents a chlorine atom, a bromo atom, an iodo atom, or a leaving group such as a methanesulfonyloxy group or a p-toluenesulfonyloxy group. ] It can also be obtained by reacting the compound shown in the following in the presence of a base.

Examples of the base used in the above reaction include alkali metal hydrides such as sodium hydride.

In the above reaction, the reaction temperature is typically -10 to 10
The reaction time was 0.1 to 24 hours at 0°C, and the amount of reagent used in the reaction was 1 mole of the cyanoacetamide derivative represented by the general formula (IVI) to The amount of the compound contained is 1 to 1.5 mol, and the amount of the base is 1 to 1.2 mol.
It is a mole.

Solvents that can be used in the above reaction include aliphatic hydrocarbons such as hexane, aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as tetrahydrofuran, dioxane, and 1,2-dimethoxyethane, After completion of the reaction, which includes aprotic polar solvents such as dimethyl reformamide, etc., ordinary post-treatments such as extraction, concentration, and filtration are carried out, and if necessary, operations such as column chromatography and recrystallization are carried out. By doing so, the desired compound of the present invention can be obtained.

In addition, the cyanoacetamide derivative represented by the general formula (fV), which is one of the raw material compounds for producing the compound of the present invention, is a combination of an α-methylbenzylamine derivative represented by the general formula [■] and cyanoacetic acid or its It can be obtained by reacting with a reactive derivative in the presence of a reaction aid if necessary.

In addition, the compound represented by the general formula [v], which is the other raw material compound, can be obtained by using a commercially available one or by synthesizing it from a commercially available raw material by a normal derivatization method. .

The compound of the present invention has at least four stereoisomers (optical isomers) derived from its asymmetric carbon atoms, and the present invention also includes these isomers and mixtures thereof.

When the compound of the present invention is used as an active ingredient of a plant disease control agent, it may be used as it is without adding any other ingredients, but usually a solid carrier 1, a liquid carrier, a surfactant, and other formulation aids are used. It is used by mixing it with a drug and preparing it into 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%.

As solid carriers, fine powders such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, soybean oil, and cottonseed oil. Examples include vegetable oils such as, dimethyl sulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Nonionic sulfonates, dialkyl sulfosuccinates, preoxyethylene alkyl surfactants, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan Ill fatty acid esters, etc. Examples include surfactants.

As formulation adjuvants, lignin sulfonate, flune am, polyvinyl alcohol, gum arabic, CM
Examples include C (carboxymethyl cellulose) and PAP (isopropyl acid phosphate).

These preparations can be used as is or mixed with other plant disease control agents, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. It can also be used as

When the compound of the present invention is used as an active ingredient of a plant disease control agent, the amount to be treated depends on weather conditions, formulation form, treatment time,
Although it varies depending on the method, location, target disease, target crop, etc., it is usually 0.05 to 2001. Preferably Q is 1 to 1 GOf, and when applying an emulsion, wettable powder, suspension agent, etc. diluted with water, the application concentration is 0.0000
The amount is 5 to 0.5%, preferably 0.0001 to 0.2%, and granules and powders are applied as they are without any dilution.

<Effect of the invention>.

Since the compounds of the present invention have excellent effects against plant diseases caused by various plant pathogens, they can be used for various purposes as active ingredients 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 (7)) 2-cyano-3,3-dimethino μ4-pentenoic acid 0.7
6 II (5 mmol) 0.97 F (6 mmof) of t,t'-carbonyldiimidazole was added little by little to a solution dissolved in total anhydrous tetrahydrofuran 5-, and the mixture was stirred at room temperature for 1 hour. 0.78 Da (5 mmol) of 1-(4-chlorophenyl)ethylamine was slowly added dropwise to this solution, and the mixture was stirred at room temperature for 2 hours. After the reaction, ether was added, and the mixture was washed successively with 5% hydrochloric acid, saturated deuterated water, and saturated brine. After drying the organic layer over anhydrous magnesium sulfate, the solvent was distilled off to obtain a viscous liquid of 1.14 f/. This was carried out using silica gel column chromatography (
Elution solvent; hexane: ethyl acetate = 5: L) to purify with 0.72 f of N-(1-(4-chlorophenyl)ethyl]-2-cyano 3.3-dimethyl-4-
Pentenamide was obtained.

mp102-105℃'H-NLViRCCDC1a/TMS, δ(pl)
m)) 1.0-1.6 (m, 9H), 3.28 (S, I
H), 4.6-5.8 (m, 8H), 5.5-6
．． 1 (m, IH), 6.5-6.9 (br
d, IH), 6.95–7.4 (m, 41(
) Production Example 2 (Compound (3)) N-(1-(4-chlorophenyl)ethyl]-2-cyanoacetamide 0.89F (4 mmol) was dissolved in anhydrous dimethylformamide 5- and cooled on ice. Under nitrogen atmosphere. ,
Sodium hydride (60% in oil) 0. l
7f (4.2 mmol) was added and stirred for 30 minutes under water cooling. Next, 3- Bromo! -Butyne (C561(
After adding 4.2 rnmol) and stirring for 30 minutes under water cooling, the water cooling path was removed and the mixture was further stirred for 4 hours. After the reaction, water was added to the reaction solution, extracted with ethyl acetate, and washed twice with brine. The organic layer was dried and concentrated, and the residue was separated by adding hexane and acetonitrile solutions. The acetonitrile layer was concentrated to obtain 1.25 g of a resinous compound.

This was purified by silica gel column chromatography (elution solvent: hexane: ethyl acetate = 5:1), and
．． 6 Of of N-(1-(4-chlorophenyl)ethyl']-2-Sifno-8-methyl-4-pentynamide was obtained.

mp75-77°C' H-NMR (CD(J'a/TMS, δ(ppm
)) 1.15-1.65 (rn, 6H'), 2.
15-2.85 (m.

1) (), 2.95-8.7 (m, 2H), 4.
75-5.85 (m, 1)i), 6.65-7. Q(b
r, 1) I), 7.1 to 7.4 (m, 4H) Production Example 3 (Compound (95)) 2-cyano-8,8-dimethyl-4-pentynic acid 0.4
51 (8 mmol) was dissolved in anhydrous Ti (FIC),
To this, 1,1'-carbonyldiimidazole 0.581
(8.6 mmol) was added in excess.

After stirring at room temperature for 1 hour, 1-(4-trifluoromethoxyphenyl)ethylamine 0.621 (8 mmo
l) was added. After stirring at room temperature for 4 hours, the solvent was distilled off and 1#
0.92 g of N-[1-(4-trifluoromethoxyphenyl)ethyl]-2-cyano-8°8-dimethyl-4-pentinamide was obtained.

mp 71-75°C' H-NMR (CDCI B /TMS, δ(pp
m) 1.2-1.7 (m, 9H'), 2.88 (
s, 1f(), 8.81 (8, IH), 4.8-5.4
(m, IH), 6.85-6.9 (br,
IH), 6.95-7.5 (m, 4l-I) Production Example 4 (Compound (47)) 1-(4-bromophenyl)ethylamine 0, 601
(8 dishes o1) and triethylamine 0,849 (8,
13 mmol) was dissolved in 10-acetonitrile and cooled on ice. 0.489 (3 mmol) of α-cyano-5ec-butylacetyl chloride was added dropwise to this solution, and the mixture was stirred at room temperature for 2 hours.

After the reaction, ethyl acetate was added, washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a viscous liquid of 1.07 g.
I got fi. This was purified by silica gel column chromatography (elution solvent: hexane:acetone = 5:l) to obtain 0.90jl of N-(1-(4-bromophenyl)ethyl]-2-cyano-8-methylpentanamide. Ta.

'H-NMR (CDCa/TMS, δ(ppm
))0.65-1.8 (m%11H), 1.8-2
．． 4 (m, IH), 8-8.5 (m, IH)
, 4.7-5.8 (m, IH), 6.2-6.7 (
m, IH), 6.9-7.6 (m, 4H) mass spectrum (m/e, riOev) 822CM), 807.265, 198.18
1, 104 Production Example 5 (Compound (4B)) 0.89 f (4 mmol) of N-(1-(4-chlorophenol)ethyl]-2-cyanoacetamide was dissolved in dimethylformamide 5-1 and added. Sodium hydride (60% in oil) 0.17 under nitrogen atmosphere
1 (4.2 mmol) was added thereto, and the mixture was stirred for 30 minutes under water cooling. This was followed by cyclopentyl bromide 0.7 B I (
After stirring for 80 minutes under water cooling, the water cooling bath was removed and the mixture was further stirred for 4 hours. After the reaction, water was added to the reaction solution, extracted with ethyl acetate, and diluted with brine.
Washed twice. After drying the organic J-, it was concentrated, and hexane and acetonitrile solutions were added to the residue, stirred, and then the layers were separated. 1 tIJ of acetonitrile was concentrated to obtain 1.08N of a bulk compound. This was subjected to silica gel column chromatography (elution solvent; hexane: ethyl acetate = 5 = 1
) to obtain 0.58 g of N-(1-(4-chlorophenyl)ethyl]-2-leanor-2-lecropentylethanamide.

mp 106-108℃' H-NMR (DMbO-da/TMS, δ(p
pm)) 0.8-2.0 (m, 11)I),
2.1-2.6 (m, tH), 8.60 (d,
J-9Hz, 1)1), 4.6~5.2 (m
.

IH), 7.88 (bra, 4H), 8.7
(b rd, LH) Table 1 shows some of the compounds of the present invention that can be produced by such a production method.

Next, a production example of the α-methylbenzylamine derivative represented by the general formula (1) will be shown.

Reference production example p-(t,1,2.2-tetrafluoroethoxy)acetophenone 9.44IC40■01), formamide 7
．． A mixture of 4:M (160 oi) and 90% formic acid l- was heated at 180-190°C for 5 hours and cooled. The resulting crystals were collected and washed successively with cold water and cold hexane. The obtained crystals (1 G, ?#) were suspended in 20 mm of ethanol, 20 mm of 6N hydrochloric acid was added, and the mixture was heated at 60 to 60° C. for 1 hour. The mixture was cooled on ice, water was added, and the mixture was extracted twice with methylene chloride. 40% caustic soda aqueous solution 16 while cooling the aqueous layer on ice.
After the mixture was made alkali-strengthened with -, the mixture was extracted twice with ether.

By drying with anhydrous magnesium sulfate and concentrating,
Almost pure 1-(4-(1,1,2,2
-tetrafluoroethoxy)phenyl]ethylamine 5
．． 91 (68%) was obtained.

a- represented by the general formula [■] that can be produced in this way
Some of the methylbenzylane derivatives are shown below.

Compound Represented Next, an example of the production of a cyanoacetamide derivative represented by the general formula (ff) will be shown.

Reference production example Ethyl cyanoacetate 8.65f (80 mmol)
and 1-(4-bromophenyl)ethylamine 6.0
1 (80 mmol) was heated and stirred in a bath ff1180"c! for 2 hours while removing the generated ethanol, and then cooled. The resulting crystals were recrystallized from ethanol to obtain N-(1-(4-bromophenyl). ) ethyl]-2-cyanoacedoelectrode 5.11f (yield 64%) was obtained.

mp1B6~189'0'H-NMR (CDCII/DMSO-d6, δ(p
pm)) 1.81 (d, J=7Hz, 8H), 8.81 (8,8H), 8.59 (8,2H), 4.6
~5.1 (m, IH), 6.95~7.6 (m,
4H), 8.8 to 8.8 (br d , IH) Some of the cyanoacetamide derivatives represented by the general formula (IV) that can be obtained by such a production method are shown below.

Examples of formulations of the compound shown below are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts represent parts by weight.

Formulation Example 1 50 parts each of the compounds (1) to (99) 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 form a water-particle formulation for each of the compounds of the present invention. get.

Formulation Example 2 25 parts each of the compounds (1) to (9?) of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMCa, and 69 parts of water were mixed and wet-processed until the particle size of the active ingredient became 5 microns or less. A suspension of each of the compounds of the present invention is obtained by pulverization.

Formulation Example 3 Two parts each of the compounds (1) to (9) of the present invention, 88 parts of kaolin clay, and 10 parts of talc are thoroughly 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 (9F) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 60 parts of xylene
The components are thoroughly mixed to obtain an emulsion of each compound of the present invention.

Formulation Example 5 2 parts each of the compounds (1) to (Cfi) of the present invention, synthetic water-containing a
4 [1 part of base, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 66 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, then granulated and overturned to form granules of each of the compounds of the present invention. get.

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 compound numbers in Table fs1, and the compounds used for comparison are indicated by compound symbols in Table 2.

Table 2 The control efficacy is determined by visually observing the diseased state of the test plants at the time of investigation, i.e., the degree of bacterial flora and lesions on the stems, etc., and if no bacterial flora or lesions are observed, r5J, 10%. If it is recognized to a certain extent, it is "4", if it is recognized to about 80%, it is r8J, if it is recognized to about 50%, it is r2j, and if it is recognized to about 70%, it is "1".
If there is no difference from the disease onset state when no compound is tested, it is evaluated as "0" and evaluated on a 6-level scale, which is indicated as 6, 4, 8, 2, 1, or 0, respectively.

Test Example 1 Rice blast disease control test (preventive effect) A plastic pot was filled with sandy loam, and rice (Kan F & No. 88) was sown and grown in a greenhouse for 20 days. A test chemical prepared as a hydrating powder according to Formulation Example 1 was cooled with water to a predetermined concentration, and was sprayed on the foliage of rice seedlings so as to sufficiently adhere to the 11 sides. After spraying, the plants were inoculated with 411 air-dried spore suspensions of the blast fungus. The pesticidal efficacy was investigated using a 28° C1 inoculation machine in darkness and high humidity for 4 days. The results are shown in Table 8.

Table 8 Trial example 2 Rice blast control test (penetration transfer effect) Fill plastic pots with sandy loam and use rice (Kinki No. 83)
were sown and grown in a greenhouse for 14 days. For young rice seedlings,
The test drug made into an emulsion according to Formulation Example 4 was diluted with water,
The predetermined amount was irrigated to ±1. After irrigation, the plants were grown in a greenhouse for 7 days, and then sprayed and inoculated with a spore suspension of the blast fungus. After inoculation, the plants were kept in a 28°C dark and humid environment for 4 days, and then the control efficacy was investigated. The results are shown in Table 4.

Table 4

Claims (6)

[Claims] (1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R is a primary or secondary alkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, 2,2 -dimethylpropyl group or an alkenyl group or alkynyl group having 8 to 6 carbon atoms; X and Y are the same or different and represent a hydrogen atom, a fluorine atom, or a chlorine atom; Represents a fluoromethyl group, lower fluoroalkoxy group, cyano group, nitro group, methyl group, methoxy group or methylthio group. ] A cyanoacetamide derivative represented by. (2) General formula▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [In the formula, R' is a secondary alkyl group having 3 to 5 carbon atoms, or a secondary or tertiary alkenyl group having 4 to 5 carbon atoms. or represents an alkynyl group, X and Y are the same or different and represent a hydrogen atom, a fluorine atom or a chloro atom, and Z' is a chloro atom, a bromine atom, an iodo atom,
Represents a fluoromethyl group or a lower fluoroalkoxy group. ] A cyanoacetamide derivative represented by. (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a hydrogen atom, a fluorine atom, or a chloro atom, and Z is a hydrogen atom, a halogen atom, or a trifluoromethyl group. , lower fluoroalkoxy group, cyano group, nitro group, methyl group, methoxy group, or methylthio group. ] α-Methylbenzylamine derivatives represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R is a primary or secondary alkyl group having 2 to 6 carbon atoms, cycloalkyl groups, 2,2-
Represents a dimethylpropyl group or an alkenyl group or alkynyl group having 8 to 6 carbon atoms. ] The method for producing a cyanoacetamide derivative according to item 1, which comprises reacting with an α-substituted cyanoacetic acid or a reactive derivative thereof. (4) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a hydrogen atom, a fluorine atom, or a chloro atom, and Z is a hydrogen atom, a halogen atom, a trifluoro Represents a methyl group, lower fluoroalkoxy group, cyano group, nitro group, methyl group, methoxy group, or methylthio group. ] and the general formula R''-L [wherein R'' is a primary or secondary alkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, Represents a primary or secondary alkenyl group having 8 to 6 carbon atoms or a primary or secondary alkynyl group having 8 to 6 carbon atoms,
L represents a chloro atom, a promo atom, an iodo atom, or a leaving group such as a methanesulfonyloxy group or a p-toluenesulfonyloxy group. ] General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R'', X, Y and Z have the same meanings as above.] Method for producing cyanoacetamide derivatives. (5) A plant disease control agent containing the cyanoacetamide derivative described in item 1 as an active ingredient. (6) A rice blast control agent containing the cyanoacetamide derivative described in item 1 as an active ingredient.