JPH07149701A - Itaconic acid derivative - Google Patents

Abstract

PURPOSE:To obtain a new itaconic acid derivative useful as a germicide having ability to control developing diseases in crops, causing no chemical injuries and presenting excellent effect of bringing crop harvest improvement. CONSTITUTION:This itaconic acid derivative is of formula I[R1 is (substituted) phenyl or (substituted) benzyl; R2 is H, 1-3C alkyl or 2-3C alkenyl; Q is 2-4C alkylene or 2-7C (substituted) alkenylene, excepting that R1 is 3,5-dichlorophenyl or 3,4-dichlorophenyl; R2 is methyl and Q is alpha-methylethylene], e.g. 2-[N-(2,4- dichlorophenyl) carbamoylmethyl]-2-propenoic methyl ester. The compound of formula I can be obtained, for example, by reaction of an aniline or amine of formula R1-NH2 with an acid anhydride of formula II in the presence of a inert solvent.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel compound useful as a bactericide.

[0002]

2. Description of the Related Art As a compound similar to the itaconic acid derivative of the present invention, for example, there is a compound disclosed in EP-0034556. However, except for a part, the compound of the present invention is a substituent in a substituted phenyl group. In different positions or types, and the compounds described in this patent are not described as fungicides.

[0003]

The high productivity of today's agriculture is ensured by using fertilizers, agricultural chemicals and various agricultural materials. On the other hand, emergence of drug-resistant bacteria due to continuous application of pesticides and disease caused by continuous cultivation of region-intensive single crops are becoming serious problems.

[0004]

Under these circumstances, there is a strong demand for the development of highly safe drugs, and the present invention provides a general formula [Chemical formula 1] as a means for solving the problems.

[0005]

[Chemical 3]

(In the formula, R ₁ is a phenyl group or a substituted phenyl group (the substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, and the number of substituents is 1 to 5)) A benzyl group or a substituted benzyl group (the substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, and the number of substituents is 1 to 5), and R ₂ is hydrogen or carbon. Represents an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, Q is an alkylene group having 2 to 4 carbon atoms, an alkenylene group having 2 to 7 carbon atoms or a substituted alkenylene group (the substituent is a carbon atom). 1 to 3 alkoxy group, 1 to 3 carbon atoms
Of alkoxyimino group, naphthyl group, phenyl group, or 1 to 5 positions are halogen atoms, alkyl groups having 1 to 3 carbon atoms, and substituted phenyl groups substituted with haloalkyl). However, compounds in which R ₁ is a 3,5-dichlorophenyl group or a 3,4-dichlorophenyl group, R ₂ is a methyl group and Q is an α-methyleneethylene group are excluded. The present invention provides an itaconic acid derivative represented by (4) and a fungicide containing the same as an active ingredient.

Specific compounds of the present invention are shown below. Hereinafter, this compound No. will be used to represent individual compounds. [No.1] 2- [N- (2,4-dichlorophenyl) carbamoylmethyl] -2-propenoic acid methyl [No.2] 2- [N- (4-chlorophenyl) carbamoylmethyl] -2-propenoic acid methyl [No. 3] 2- [N- (2-chlorophenyl) carbamoylmethyl] -2-propenoic acid methyl [No. 4] 2- [N- (3-chlorophenyl) carbamoylmethyl] -2-propenoic acid methyl [No. .5] Methyl 2- [N- (4-methylphenyl) carbamoylmethyl] -2-propenoate [No.6] Methyl 2- [N- (3,5-dichlorophenyl) carbamoylmethyl] -2-propenoate ( This compound is not a novel compound) [No.7] 2- [N- (2,3-dichlorophenyl) carbamoylmethyl] -2-propenoic acid methyl [No.8] 2- [N- (3,4 Methyl dichlorophenyl) carbamoylmethyl] -2-propenoate (This compound is not a novel compound) [No. 9] 2- [N- (4-trifluoromethylphenyl) carbamoylmethyl] -2-propenoic acid methyl [No. 10] 2- [N- (3,5-difluorophenyl)
Carbamoylmethyl] -2-propenoic acid [No.11] 2- [N- (2,3-dichlorophenyl) carbamoylmethyl] -2-propenoic acid isopropyl [No.12] 2- [N- (2,3-dichlorophenyl) ) Carbamoylmethyl] -2-propenyl 2-propenyl [No.13] 2- [N- (4-methoxyphenyl) carbamoylmethyl] -2-propenoic acid methyl [No.14] 2- [N- (4- Methyl nitrophenyl) carbamoylmethyl] -2-propenoate [No.15] 2- [N- (4-trifluoromethylphenyl) carbamoylmethyl] -2-propenoic acid [No.16] 2- [N- ( Methyl 4-chlorobenzyl) carbamoylmethyl] -2-propenoate [No.17] Methyl 2- [N- (2-chlorobenzyl) carbamoylmethyl] -2-propenoate [No.18] -[N- (3,5-Di (trifluoromethyl) phenyl) carbamoylmethyl] -2-propenoic acid [No. 19] 3- [N- (3,5-dichlorophenyl) carbamoyl] -2-propenoic acid methyl ester Methyl [No. 20] 3- [N- (3,5-dichlorophenyl) carbamoyl] propionate [No. 21] 2- [N- (2-Fluoro-4-chloro-5
-(2-propoxy) phenyl) carbamoylmethyl]
Methyl-2-propenoate [No.22] 2- [N- (2-fluoro-4-chloro-5
-(2-propoxy) phenyl) carbamoylmethyl]
-2-Propenoic acid [No. 23] 3- [N- (2-fluoro-4-chloro-5
Ethyl-(2-propoxy) phenyl) carbamoyl] propionate [No.24] 2- [N- (2-fluoro-4-chloro-5
-(2-propoxy) phenyl) carbamoylmethyl]
Methyl -4-methyl-2-pentenoate [No. 25] 2- [N- (2-Fluoro-4-chloro-5
-(2-propoxy) phenyl) carbamoylmethyl]
Ethyl-3- (1-naphthyl) -2-pentenoate [No. 26] 2- [N- (2-Fluoro-4-chloro-5
-(2-propoxy) phenyl) carbamoylmethyl]
Ethyl-3- (2-methylphenyl) -2-pentenoate.

Among the specific compounds according to the present invention described above, more preferable compounds as fungicides are shown in [Table 1] together with their physical properties.

[0009]

[Table 1]

[0010]

[Table 2]

[0011]

[Table 3]

[0012]

[Table 4]

The compounds of the present invention are all novel compounds and can be produced by the methods shown below.

Aniline and amines represented by the general formula [Chemical Formula 6] (R ₁ --NH ₂ [Chemical Formula 6]) (in the formula, R 1 is a phenyl group, a substituted phenyl group (substituent is a halogen atom, carbon number is 1 ~ 3 alkyl group, haloalkyl group, alkoxy group or nitro group, the number of substituents is 1 to 5), benzyl group or substituted benzyl group (substituent is a halogen atom, alkyl group having 1 to 3 carbon atoms, haloalkyl group, An alkoxy group or a nitro group, the number of substituents of which is 1 to 5)) and an acid anhydride represented by the general formula [Chemical Formula 4]

[0016]

[Chemical 4] (In the formula, Q is an alkylene group having 2 to 4 carbon atoms and 2 carbon atoms.
To 7 alkenylene group or substituted alkenylene group (substituent is an alkoxy group having 1 to 3 carbon atoms, an alkoxyimino group having 1 to 3 carbon atoms, a naphthyl group, a phenyl group, or a halogen atom at 1 to 5 positions, a carbon atom). Represents a 1 to 3 alkyl group, a substituted phenyl group substituted with haloalkyl). ) Are reacted with each other in the presence of an inert solvent to give an amide or carboxylic acid derivative represented by the general formula [Chemical Formula 5].

[0017]

[Chemical 5] Can be obtained. However, in this case, R ₂ in the general formula [Formula 1] is limited to a hydrogen atom.

In this reaction, 1 to 2 mol of aniline and amine [Chemical formula 6] are used per 1 mol of acid anhydride [Chemical formula 4],
It is carried out by stirring at a temperature of -10 to 200 ° C, preferably 30 to 100 ° C for several hours.

As the solvent, any solvent can be used so long as it is inert to the reaction. For example, acetone, acetonitrile, toluene, N, N-dimethylformamide, dimethylsulfoxide, dioxane, tetrahydrofuran,
An aprotic solvent such as toluene or xylene is preferably used. In this reaction, an amide and a carboxylic acid derivative [Chemical formula 5] can be easily obtained by reacting [Chemical formula 6] and [Chemical formula 4] in the above-mentioned organic solvent. Triethylamine, 4,4-dimethylaminopyridine, 1,8-diazabicyclo [5,4,4]
In some cases, an organic base such as 0] -7-undecene (DBU) is added.

After completion of the reaction, the solvent is distilled off to obtain the desired product. It can also be obtained by adding an organic solvent such as n-hexane, toluene, petroleum ether, and the like to separate the target product and distill off the solvent.

Further, in the general formula [Chemical formula 1], the compound in which R ₂ is other than a hydrogen atom is produced by the following two methods. One is manufactured by the following reaction formula.

That is, the amide or carboxylic acid derivative represented by the above general formula [Chemical formula 5] is converted into the general formula [Chemical formula 7] (R ₂
-OH [Chemical formula 7] (in the formula, R ₂ is hydrogen, and the carbon number is 1 to 3)
Represents an alkyl group or an alkenyl group having 2 to 3 carbon atoms. By esterifying with an alcohol represented by the formula (1), a compound of the general formula [Chemical Formula 1] is obtained.

This reaction is carried out by adding an amide or carboxylic acid derivative in a solvent of alcohols to a catalytic amount of concentrated sulfuric acid or an organic acid such as p-toluenesulfonic acid or trifluoroacetic acid, and refluxing the mixture for several hours. In general, a hydrocarbon such as toluene or xylene is used as a solvent, and 1 to 3 mol of an alcohol [Chemical formula 7] is used for 1 mol of an amide or a carboxylic acid derivative [Chemical formula 5]. It is also carried out by adding an amount of concentrated sulfuric acid or an organic acid such as p-toluenesulfonic acid or trifluoroacetic acid, refluxing for several hours, and removing water generated.

After completion of the reaction, the solvent is distilled off and the compound of the general formula [Chemical formula 1] is obtained by purification by means such as chromatography.

In addition to the above methods, these compounds can be produced by the following reaction formula.

That is, the amide or carboxylic acid derivative represented by the above general formula [Chemical formula 5] is converted into the general formula [Chemical formula 8] (R ₂
-X [Chemical Formula 8]) (wherein R ₂ represents hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms), and a basic condition The compound of the general formula [Chemical Formula 1] can be produced by alkylating under the following conditions.

In this reaction, 1 to 3 mol of an alkyl halide [Chemical Formula 8] is used with respect to 1 mol of an amide or carboxylic acid derivative [Chemical Formula 5], and -20 to 200 ° C, preferably 30 to 10 C
It is carried out by stirring at a temperature of 0 ° C. for several hours.

This reaction is preferably carried out under basic conditions, and as such a base, for example, sodium hydride, potassium carbonate, sodium carbonate, potassium hydroxide, sodium hydroxide and the like are preferably used. As the solvent, any solvent can be used as long as it is inert to the reaction.
N-dimethylformamide, dimethyl sulfoxide, dioxane, tetrahydrofuran, ethylene glycol diethyl ether and the like are preferably used.

After completion of the reaction, the solvent is distilled off and the product is purified by a means such as chromatography to obtain [Chemical formula 1]
Is obtained.

[0030]

EXAMPLES The present invention will be specifically described below with reference to Examples (Synthesis Examples, Formulation Examples and Test Examples), but the present invention is not limited to these. Hereinafter, the present invention will be specifically described with reference to synthesis examples.

Synthesis Example 1 2- [N- (3,5-difluorophenyl) carbamoylmethyl] -2-propenoic acid (Compound No. 10) 3,5-difluoroaniline 1.3 g (0.01 mo)
l) and itaconic anhydride 0.79 g (0.007 m)
ol) was dissolved in 30 ml of acetone, and the reaction was carried out at room temperature with stirring for 2 hours. After removing the solvent, the precipitated crystals were recrystallized from toluene to give 0.9
5 g was obtained. mp. 164-166 ° C Yield: 56%

[Synthesis Example 2] Methyl 2- [N- (2,4-dichlorophenyl) carbamoylmethyl] -2-propenoate (Compound No. 1) 2,4-dichloroaniline 1.62 g (0.01 mo)
l) and itaconic anhydride 0.79 g (0.007 mo
l) is dissolved in 30 ml of acetone and stirred at room temperature.
The reaction was carried out for 2 hours. After removing the solvent, the reaction mixture was redissolved in 30 ml of methanol without purification, a catalytic amount of concentrated sulfuric acid was added, and the mixture was refluxed for 2 hours. The reaction mixture was poured into cold water and the oil that separated was extracted with ethyl acetate,
The extract was washed with water, dried over magnesium sulfate, evaporated to remove the solvent, and recrystallized from toluene to obtain 1.25 g of the desired product. mp. 93.5-94 ° C. Yield (Tota
l): 62.5%

Synthesis Example 3 Methyl 3- [N- (3,5-dichlorophenyl) carbamoyl] -2-propenoate (Compound No. 19) 2,4-Dichloroaniline 1.62 g (0.01 mo)
l) and maleic anhydride 0.69 g (0.007 mo
l) is dissolved in 30 ml of acetone and stirred at room temperature.
The reaction was carried out for 3 hours. After removing the solvent, the precipitated crystals were recrystallized from toluene to obtain 1.40 g (yield: 78%) of an intermediate amide and carboxylic acid. Next, 1.40 g (5.4 mmo) of this amide and carboxylic acid
1) was dissolved in 30 ml of N, N, -dimethylformamide, 0.92 g (6.5 mmol) of methyl iodide was added dropwise at room temperature in the presence of 0.97 g (7.0 mmol) of potassium carbonate, and then 2 hours. It was made to react. The reaction mixture was poured into cold water, the oily substance that separated was extracted with ethyl acetate, the extract was washed with water, dried over magnesium sulfate, the solvent was distilled off, and the target product was purified by column chromatography. 11 g (yield: 75%) was obtained. mp. 172 to 174 ° C. Yield (Tota
l): 58%

When the fungicide of the present invention is used, the compound is mixed with various carriers and additives according to the purpose by a general agricultural chemical production technique to prepare a wettable powder, an emulsion, a powder, It can be used in various forms such as granules and flowable agents.

Of the carriers to be added, the liquid carrier is
Conventional organic solvents are used. Usual clay minerals, pumice, etc. are used as the solid carrier. Further, a surfactant can be added in order to impart emulsifiability, dispersibility, spreadability and the like to the formulation. Furthermore, it can be used by mixing with agricultural chemicals such as fertilizers, herbicides, insecticides and other fungicides.

In order to use it as a bactericide, it is necessary to apply the active ingredient compound sufficiently so that the desired effect is exhibited. The application amount can be applied in the range of 20 to 2000 g / ha, but preferably 100
A range of up to 1000 g / ha is suitable. It is used by formulating it in the form of a wettable powder, an emulsion, a powder, a granule and a flowable agent with the content of the active ingredient being 0.1 to 50%.

Emulsions can be prepared by dissolving the active ingredient in an agriculturally usable organic solvent and adding a solvent-soluble emulsifier. As the solvent, xylene, orthochlorotoluene, cyclohexanone, isophorone, N, N
-Dimethylformamide, dimethylsulfoxide, or mixtures thereof can be used. A particularly suitable solvent is a mixed solvent of an aromatic hydrocarbon, a ketone and a polar solvent. The surfactant used as an emulsifier is used in an amount of 1 to 20% by weight of the emulsion. Further, as the type, any of anionic, cationic and nonionic can be used. The concentration of active ingredient is 0.5-50
A range of 5% by weight, preferably 5 to 30% by weight is suitable.

Specific examples of the above-mentioned surfactant are as follows. Examples of the anionic surfactant include alkyl sulfate ester, alkyl diphenyl ether disulfonate, naphthyl methane sulfonate, lignin sulfonate, alkyl sulfosuccinate, alkyl benzene sulfonate and alkyl phosphate. Examples of cationic surfactants include alkylamine salts and quaternary ammonium salts. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, and polyoxyethylene fatty acid ester. To be

A wettable powder is prepared by adding an active ingredient to an inert finely divided solid carrier and a surfactant. The active ingredient is in the range of 2 to 50% by weight, and the surfactant is 1 to 20%.
It is common to mix in wt%. As inert finely divided solid carriers, naturally occurring clay, silicates, silica and carbonates of alkaline earth metals can be used. Representative examples of these are kaolin, sieglite, talc, diatomaceous earth, magnesium carbonate, calcium carbonate and dolomite. As the emulsifier, the spreading agent, and the dispersant, generally used anionic surfactants, nonionic surfactants, and mixtures thereof can be used. As the system of each surfactant, the same system as that used for the emulsion can be used.

Dust agents include talc, finely divided clay, pyrophyllite,
Formulation is carried out by incorporating the active ingredient into an inert carrier commonly used for the production of powders such as diatomaceous earth and magnesium carbonate. The concentration of the active ingredient is 0.1 to 20% by weight
In particular, the range of 0.5 to 5% by weight is suitable.

Granules are prepared by mixing the active ingredient with an inert finely divided carrier such as bentonite, diatomaceous earth, kaolin clay or talc, kneading with water and using a granulator. Alternatively, granulate in advance to a particle size range of 15
~ 30 mesh granular carrier, natural pumice stone,
It can also be prepared by adhering a solution in which the active ingredient and the spreading agent are dissolved to a granular mineral in which the acid clay and zeolite are crushed to adjust the particle size range. The active ingredient concentration of such granules is 0.2 to 20% by weight, especially 1
A range of from 10% by weight is suitable.

The flowable agent is obtained by pulverizing the active ingredient into a fine powder and mixing it with a surfactant and water. The surfactant used here is an anionic surfactant or cationic surfactant listed for the emulsion. Both the agent and the nonionic surfactant are used alone or in combination. The amount used is generally 1 to 20% by weight. The active ingredient is suitably in the range of 1 to 50% by weight, preferably 2 to 20% by weight.

Due to its excellent antibacterial activity, the compound of the present invention represented by the above-mentioned general formula [Chemical Formula 1] exerts an effect as a fungicide for agricultural and horticultural use against plant diseases caused by a wide range of microorganisms. For example, tomato late blight, downy mildew, various powdery mildew, apple scab, wheat rust, wheat rot, rice blast, rice blight, various gray molds, rice wilt, cucumber. It shows an excellent control effect against spotted bacterial diseases. Further, since the compound of the present invention has not only an excellent preventive effect but also an excellent therapeutic effect, it is possible to control diseases by treatment after infection.

Hereinafter, the composition of the present invention will be specifically shown as formulation examples according to dosage forms. {Formulation Example 1 (Emulsion)} Compound No. 12 20 parts Orthochlorotoluene 40 parts Cyclohexanone 35 parts Solpol 900B 5 parts "Solpol": Toho Chemical Industry Co., Ltd. Trademark The above ingredients are uniformly mixed and dissolved to obtain the emulsion of the present invention. Obtained.

[Formulation Example 2 (wettable powder)] Compound No. 6 25 parts Kaolin clay 57 parts Solpol 5039 9 parts Solpol 5060 9 parts The above components were mixed and ground to obtain the wettable powder of the present invention.

[Formulation Example 3 (powder)] Compound No. 19 5 parts Kaolin clay 95 parts The above components were mixed and ground to obtain the powder of the present invention.

[Formulation Example 4 (Granule)] Compound No. 9 6 parts Bentonite 44 parts Talc 44 parts Lignin sulfonate soda 6 parts The above components are uniformly mixed and pulverized, and water is added to the mixture to knead and granulate. It was dried to obtain the granule of the present invention.

[Formulation Example 5 (flowable agent)] Compound No. 2 10 parts Ethylene glycol 6 parts Solpol 3078 6 parts Solpol 7512 1 part Water 77 parts The above ingredients were uniformly mixed and pulverized to obtain the flowable agent of the present invention.

[Formulation Example 6 (Emulsion)] Compound No. 3 10 parts Isophorone 22 parts Orthochlorotoluene 28 parts Xylene 22 parts Solpol 900A 9 parts Solpol 900B 9 parts The above ingredients are uniformly mixed and dissolved to obtain the emulsion of the present invention. It was

Hereinafter, the control effect of the compound of the present invention against filamentous fungi will be specifically described with reference to test examples.

[Test Example 1] Tomato epidemic preventive effect test Each test sample prepared in accordance with Formulation Example 1 when tomato (variety: strong rice longevity) was cultivated in a plastic cup having a diameter of 7 cm and the leaf stage reached the 2 leaf stage. The compound was adjusted to 200 ppm, and 10 ml of the test compound drug solution was sprayed using a spray gun. For each test compound, two plants in one section were treated in a double loop. One day after the chemical treatment, each plant was infected with Phytophthora infestans (Phytophtho), which causes tomato epidemics.
ra infestans) was spray-inoculated with a conidia suspension. After this inoculation, the tomato plants were left in a water-saturated condition at 20 ° C in the dark for 1
Culturing was carried out for 2 hours and then at 20 ° C. for 12 hours and for 6 days. Seven days after the inoculation, the lesion rates of the first and second leaves were investigated. At the same time, the test was conducted under the same conditions for the control without drug treatment. The control value was determined by the formula of [Equation 1], and the results are shown in [Table 2].

[0052]

[Equation 1]

[0053]

[Table 5]

[Test Example 2] Wheat powdery mildew prevention effect test Wheat (variety: Norin 6
No. 1) was cultivated, and when reaching the 2-leaf stage, each test compound prepared according to Formulation Example 2 was prepared at 100 ppm, and 10 ml of the test compound drug solution was sprayed using a spray gun. With respect to each test compound, 13 plants in 1 group were treated in duplicate. One day after the drug treatment, each plant was treated with Erysiphe graminis, which causes wheat powdery mildew.
minis) conidia. After this inoculation, the wheat plants were cultivated at 20 ° C. in the dark for 12 hours, and then at 20 ° C. for 12 hours with a photoperiod of 6 days. Seven days after the inoculation, the lesion rates of the first and second leaves were investigated. At the same time, the test was conducted under the same conditions for the control without drug treatment. The control value was determined by the formula of [Equation 1], and the results are shown in [Table 3].

[0055]

[Table 6]

[Test Example 3] Wheat leaf rust prevention effect test Wheat (variety: Norin 6
No. 1) was cultivated, and when reaching the 2-leaf stage, each test compound prepared according to Formulation Example 6 was prepared to 100 ppm, and 10 ml of the test compound drug solution was sprayed using a spray gun.
For each test compound, 13 plants in 1 group were treated in duplicate. One day after the chemical treatment, each plant was infected with Puccinia reco
ndita) conidial suspension. After this inoculation, the wheat plants were cultivated in a water-saturated condition at 20 ° C. in the dark for 24 hours, and then cultivated at 20 ° C. for 12 hours and a photoperiod of 6 days.
Seven days after the inoculation, the lesion rates of the first and second leaves were investigated. At the same time, the test was conducted under the same conditions for the control without drug treatment. The control value was determined by the formula of [Equation 1], and the results are shown in [Table 4].

[0057]

[Table 7]

Test Example 4 Wheat Rot Blight Prevention Effect Test Wheat (variety: Norin 6
No. 1) was cultivated, and when reaching the 2-leaf stage, each test compound prepared according to Formulation Example 2 was prepared at 200 ppm, and 10 ml of the test compound drug solution was sprayed using a spray gun.
For each test compound, 13 plants in 1 group were treated in duplicate. One day after the chemical treatment, Leptosphaerinodrum (Leptospha), which causes wheat rot, was planted on each plant.
eria nodorum) was inoculated with a conidia suspension. After this inoculation, the wheat plants were cultivated in a water-saturated condition at 20 ° C. in the dark for 48 hours, and then cultivated at 20 ° C. for 12 hours with a photoperiod of 6 days. Seven days after the inoculation, the lesion rate of the first and second leaves was investigated. At the same time, the test was conducted under the same conditions for the control without drug treatment. The control value was determined by the formula of [Equation 1], and the results are shown in [Table 5].

[0059]

[Table 8]

[0060]

INDUSTRIAL APPLICABILITY As described above, the novel compound of the present invention, when used as a fungicide, has the ability to suppress disease occurrence in crops, exhibits no medicinal damage, and exerts an excellent effect of improving yield. To do.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location C07C 233/29 7106-4H 235/06 7106-4H 235/08 7106-4H (72) Inventor Kasahara Iku, 45, Miyukigaoka, Tsukuba, Ibaraki Hodogaya Chemical Industry Co., Ltd., Tsukuba Research Institute (72) Inventor, Kisho Yokoyama, 45, Miyukigaoka, Tsukuba, Ibaraki Prefectural Tsukuba Research Institute, Ltd. (72) Inventor Katsuya Yamaguchi 45 Miyukigaoka, Tsukuba City, Ibaraki Hodogaya Chemical Industry Tsukuba Research Institute

Claims (3)

[Claims] 1. A general formula [Chemical formula 1] (In the formula, R ₁ is a phenyl group, a substituted phenyl group (the substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, the number of substituents is 1 to 5), a benzyl group Or a substituted benzyl group (a substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, and the number of substituents is 1 to 5), R ₂ is hydrogen, and the number of carbon atoms is 1 To an alkyl group having 3 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, Q is an alkylene group having 2 to 4 carbon atoms, an alkenylene group having 2 to 7 carbon atoms or a substituted alkenylene group (the substituent has 1 carbon atom). ~ 3 alkoxy group, C1 to C3 alkoxyimino group, naphthyl group, phenyl group, or 1 to 5 positions substituted with a halogen atom, C1 to C3 alkyl group, haloalkyl A substituted phenyl group), provided that
R ₁ is a 3,5-dichlorophenyl group or a 3,4-dichlorophenyl group, R ₂ is a methyl group, and Q is α.
-Excluding compounds that are methylene ethylene groups. ) Itaconic acid derivative represented by. 2. An itaconic acid derivative represented by the general formula [Chemical Formula 1] is methyl 2- [N- (2,4-dichlorophenyl) carbamoylmethyl] -2-propenoate, 2- [N-
Methyl (4-chlorophenyl) carbamoylmethyl] -2-propenoate, methyl 2- [N- (2-chlorophenyl) carbamoylmethyl] -2-propenoate, 2- [N
-(3-Chlorophenyl) carbamoylmethyl] -2-
Methyl propenoate, 2- [N- (4-methylphenyl)
Carbamoylmethyl] -2-propenoic acid methyl, 2-
Methyl [N- (2,3-dichlorophenyl) carbamoylmethyl] -2-propenoate, methyl 2- [N- (4-trifluoromethylphenyl) carbamoylmethyl] -2-propenoate, 2- [N- (3 , 5-Difluorophenyl) carbamoylmethyl] -2-propenoic acid, 2-
[N- (2,3-dichlorophenyl) carbamoylmethyl] -2-isopropyl-propenoate, 2- [N- (2,
3-Dichlorophenyl) carbamoylmethyl] -2-propenyl 2-propenyl, 2- [N- (4-methoxyphenyl) carbamoylmethyl] -2-propenoic acid methyl, 2- [N- (4-nitrophenyl) carbamoylmethyl ] -2-Methyl propenoate, 2- [N- (4-trifluoromethylphenyl) carbamoylmethyl] -2-
Methyl propenoate, 2- [N- (4-chlorobenzyl)
Carbamoylmethyl] -2-propenoic acid methyl, 2-
[N- (2-chlorobenzyl) carbamoylmethyl]-
2-Methyl 2-propenoate, 2- [N- (3,5-di (trifluoromethyl) phenyl) carbamoylmethyl] -2
-Propenoic acid, 3- [N- (3,5-dichlorophenyl) carbamoyl] -2-propenoic acid methyl, 3- [N
Methyl-(3,5-dichlorophenyl) carbamoyl] propionate, methyl 2- [N- (2-fluoro-4-chloro-5- (2-propoxy) phenyl) carbamoylmethyl] -2-propenoate, 2- [ N- (2-Fluoro-4-chloro-5- (2-propoxy) phenyl) carbamoylmethyl] -2-propenoic acid, 3- [N- (2-
Fluoro-4-chloro-5- (2-propoxy) phenyl) carbamoyl] propionate ethyl, 2- [N-
(2-Fluoro-4-chloro-5- (2-propoxy)
Phenyl) carbamoylmethyl] -4-methyl-2-pentenoate methyl, 2- [N- (2-fluoro-4-chloro-5- (2-propoxy) phenyl) carbamoylmethyl] -3- (1-naphthyl) -2-Pentenoic acid ethyl, 2- [N- (2-fluoro-4-chloro-5- (2-
Propoxy) phenyl) carbamoylmethyl] -3-
The itaconic acid derivative according to claim 1, which is ethyl (2-methylphenyl) -2-pentenoate. 3. A general formula [Chemical formula 1] (In the formula, R1 is a phenyl group, a substituted phenyl group (a substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, and the number of substituents is 1 to 5), a benzyl group or A substituted benzyl group (the substituent is a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group, an alkoxy group or a nitro group, and the number of substituents is 1 to 5), R ₂ is hydrogen, and the number of carbon atoms is 1 to 1; 3 represents an alkyl group having 3 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, Q represents an alkylene group having 2 to 4 carbon atoms, an alkenylene group having 2 to 7 carbon atoms or a substituted alkenylene group (the substituent has 1 to 3 carbon atoms). 3 alkoxy group, alkoxyimino group having 1 to 3 carbon atoms, naphthyl group, phenyl group, or substituted at 1 to 5 positions with a halogen atom, alkyl group having 1 to 3 carbon atoms, haloalkyl A bactericide containing an itaconic acid derivative represented by (representing a substituted phenyl group) as an active ingredient.