JPH0559900B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention is based on the general formula () The present invention relates to an amide-substituted fluoroethoxyacetonitrile derivative represented by the formula (wherein A is an unsubstituted or substituted phenyl group), a method for producing the same, and a herbicide for paddy fields or a fungicide for agriculture and horticulture containing the same as an active ingredient. [Prior Art] A great deal of research has been carried out on amide derivatives useful in agriculture and horticulture, and many compounds exhibiting characteristic physiological activities have been discovered and put into practical use.
For example, as substituted benzamide derivatives, ethyl-N-benzoyl-N-(3,4-
Dichlorophenyl)-2-aminopropionate (benzoylpropethyl), 2 as a fungicide
-Methyl-N-(3-isopropoxyphenyl)
Benzamide (mepronil) is known. Further, as amide-substituted acetonitrile derivatives, JP-A-57-167978, 57-176938 and 58-
Publication No. 69866 discloses herbicides and fungicides. Among these, although amide-substituted ethoxyacetonitrile derivatives are disclosed in JP-A-57-176938, there is no description of amide-substituted fluoroethoxyacetonitrile derivatives.
Regarding amide-substituted ethoxyacetonitrile derivatives, only two benzoylamino-β,β,β-trifluoroethoxyacetonitrile derivatives are disclosed. Furthermore, JP-A-57-176938 mentions the use of these compounds as fungicides and herbicides. Herbicides are tested for their herbicidal activity before and after germination, as well as for their phytotoxicity against sugar beets, rapeseed, cotton, soybeans, corn, wheat, and rice. Selective crops include cotton, sugar beet, rapeseed, lettuce, and peas, and it is specified that these compounds are useful for Asteraceae and leguminous crops, but there is no selective use for rice. However, rice is considered to be a crop to which these compounds cannot be applied. Although many herbicides such as amide compounds, thiol carbamate compounds, and diphenyl ether compounds have been developed and put into practical use as herbicides for paddy fields, their performance is still not sufficient. The amide compound butachlor is used before and after rice planting, but chemical damage to rice caused by temperature conditions has always been a problem. The use of the thiol carbamate compound molinate is regulated due to fish toxicity. Furthermore, Benthiocarb poses a problem of phytotoxicity to paddy rice under reducing soil conditions. Diphenyl ether compounds, like butachlor, are used immediately after rice planting, but their activity decreases dramatically if the treatment is delayed. All of these herbicides have excellent performance in some respects, and are therefore widely used in reality. There is a strong demand for a herbicide for paddy rice that has excellent performance. On the other hand, the compound described in JP-A-57-176938 is said to be effective as a fungicide against downy mildew of grapes and late blight of tomato. For late blight and downy mildew of various crops, use captafor, TPN, captan,
Alternatively, dithiocarbamate drugs have been widely used and have contributed to increased crop production. However, all of these compounds mainly have a preventive effect against late blight and downy mildew, and no therapeutic effect can be expected at all. Therefore, it has a major drawback in that sufficient effects cannot be expected even when the occurrence of disease is recognized. In reality, when considering the spraying of chemicals to control crop diseases, they are more or less sprayed after the disease has appeared, and it is difficult to completely control the disease with these compounds. In order to improve these points, research into new pest control agents has continued, and currently N-phenylalanine ester derivatives, such as metalaxyl [N-
(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester] and the like have been developed and are being put into practical use worldwide. However, these N-phenylalanine ester derivatives have already become a problem because of their drug-resistant bacteria. [Problems to be Solved by the Invention] The present invention overcomes the drawbacks of the prior art described above, and provides compounds, manufacturing methods, and effective methods for use as herbicides for paddy rice and fungicides for agriculture and horticulture that have extremely excellent properties. It provides pesticides as ingredients. In other words, as a herbicide for paddy rice, it has a wider range of suitable periods and is harmless, and as a fungicide for agriculture and horticulture, it has not only a preventive effect but also a therapeutic effect on various plant diseases such as late blight, downy mildew, and various types of seedling blight. together with
We also aim to find excellent compounds that are free from cross-resistance against drug-resistant bacteria, which is currently a problem. [Means and effects for solving the problem] As a result of intensive research on amide-substituted acetonitrile derivatives to solve the above problem, it was found that benzoylamino-β-fluoroethoxyacetonitrile derivative has physiological activity that could not be predicted from the above-mentioned published patent exemplified compounds. It has a wide range of suitable periods as a herbicide for paddy rice, and has little toxicity to paddy rice.
It is not toxic to fish, and as a fungicide it has both preventive and therapeutic effects against late blight, downy mildew, etc. of various plants, and also prevents seedling blight of various plants and root galls of Brassicaceae plants. The present invention was completed by discovering that soil treatment has an excellent control effect against the disease. The amide-substituted fluoroethoxyacetonitrile derivative according to the present invention has the general formula () (In the formula, A represents an unsubstituted or substituted phenyl group.)
When A is a substituted phenyl group, examples of the substituent include a halogen atom, lower alkyl, lower haloalkyl, lower alkoxy group, methylenedioxy group, nitro group, and cyano group. The number of substituents is 1 or more, and when it is 2 or more, the substituents may be the same or different. Furthermore, the present invention also provides a method for producing the amide-substituted fluoroethoxyacetonitrile derivative represented by the general formula () according to the present invention. That is, the acid chloride represented by the general formula () A-COCl () (in the formula, A indicates the above meaning) is reacted with aminoacetonitrile to form the general formula () A-CONHCH ₂ CH () (in the formula , A indicates the above-mentioned meaning) is obtained, and this is treated with a halogenating agent to obtain the general formula (). This is a production method characterized by obtaining an intermediate represented by the formula (wherein A has the above meaning and X represents a halogen atom) and then reacting this with monofluoroethanol. The production method of the present invention is shown in a reaction scheme and explained below. reaction scheme (In the formula, X represents a halogen atom) Acylaminoacetonitrile ( obtain. When this is treated with a halogenating agent in a suitable solvent, a halogenated intermediate () is obtained. These solvents include aliphatic halides such as dichloromethane, chloroform, carbon tetrachloride, and 1,4-dichloroethane, aliphatic carboxylic acid esters such as methyl acetate, ethyl acetate, isopropyl acetate, and ethyl propionate, and carbon disulfide. However, good results can be obtained by using aliphatic carboxylic acid esters, especially ester solvents such as ethyl acetate. Halogenating agents include bromine, chlorine, phosphorus oxychloride,
Sulfuryl chloride, phosphorus tribromide, etc. are used. The reaction temperature is in the range of 0 to 120°C, preferably room temperature. Note that this reaction may be performed in an inert gas atmosphere. Since the halogenated intermediate () is unstable, it is used immediately after preparation. This halogenated compound () is reacted with 2-fluoroethanol. This reaction can be carried out in the presence of an acid acceptor. Examples of acid acceptors include organic bases such as triethylamine, dimethylaniline, pyridine,
Inorganic bases include, but are not limited to, ammonia, potassium carbonate, sodium carbonate, sodium bicarbonate, sodium hydroxide, and ammonium carbonate. This reaction is preferably carried out in a solvent or diluent. Pyridine can be used both as a solvent and as an acid acceptor. This reaction is not desirable at very high temperatures because the thermal stability of the intermediate is poor, and since it is an exothermic reaction, it is desirable to conduct it under cooling. At low temperatures, reaction intermediates tend to precipitate, slowing down the reaction rate and making it impractical, so it is desirable to carry out the reaction at -30 to 50°C, preferably -20 to 20°C. The desired amide-substituted fluoroethoxyacetonitrile derivative thus obtained can be easily isolated and purified by conventional methods such as recrystallization and column chromatography. Furthermore, the present invention provides a herbicide and a fungicide for rice fields, which contain the amide-substituted fluoroethoxyacetonitrile derivative represented by the general formula () according to the present invention as an active ingredient. When using the compound of the present invention as a herbicide for paddy rice, the application amount varies depending on the growth stage of the weed, the type of weed, the dosage form of the preparation, the application method, various environmental conditions, etc., but is usually 0.1 per are. ~100g
is suitable, preferably 0.5 to 25 g. Its weed activity is characteristically strong against gramineous weeds, but it exhibits a strong suppressive effect on other weeds even when not killed. These characteristics are considered to be extremely advantageous when considering application by mixtures or tank mixes in some cases. Especially against weeds of the Cyperaceae family, such as Cyperaceae, Firefly, etc.
Similar trends are also observed for other weeds, although the strength varies depending on the type of weed. Furthermore, the timing of application of the compound of the present invention is wide ranging from before the emergence of weeds to the growing season. Compared to the known amide compound butachlor and the thiol carbamate compound bentiocarb, the compound of the present invention has a much wider usability range and has superior features not seen before. Can be easily used as a weed killer. The weed activity against Japanese millet naturally varies depending on the treatment period, but while bentiocarb and butachlor are insufficiently effective against Japanese millet at the 3.5-leaf stage at practical doses, the compounds of the present invention They exhibit sufficient activity for practical use at doses lower than their practical doses. The compound of the present invention has extremely low phytotoxicity to transplanted paddy rice no matter when it is used at any time of treatment. When the compound of the present invention is used as an agricultural and horticultural fungicide, it is not only effective against late blight and downy mildew of various crops caused by algal fungi, but also effective against various plant pathogenic fungi. It is also effective against diseases that occur. The main diseases to be controlled are potato late blight, tomato late blight, tobacco late blight, strawberry late blight, adzuki bean stem blight, grape downy mildew, cucumber downy mildew, hops downy mildew, downy mildew or clubroot of cruciferous plants. Alternatively, various crop seedling damping-off diseases caused by bacteria of the genus Afuanomyces, bacteria of the genus Pythium, etc. can be mentioned. Methods for applying the compound of the present invention include seed disinfection, foliage spraying, soil treatment, etc., but any application method commonly used by those skilled in the art will exhibit sufficient efficacy. The application amount and concentration are determined by the target crop,
Although it varies depending on the target disease, the degree of disease occurrence, the dosage form of the compound, the method of application, and various environmental conditions, etc.
When spraying, it is appropriate to use 5 to 200 g per oar, preferably 10 to 100 g per oar.
The appropriate spray concentration is 20 to 1000 ppm, preferably 50 to 500 ppm. The herbicides and agricultural and horticultural fungicides of the present invention can be mixed with other biologically active compounds, such as other fungicides, insecticides, herbicides, plant growth regulators, agricultural chemicals, soil conditioners, or fertilizing substances. Not only can they be used, but also mixed preparations with these are possible. Although the compounds of the invention may be applied neat, they are preferably applied in the form of a composition mixed with a carrier, including solid or liquid diluents. As used herein, carrier means an inorganic or organic substance, synthetic or natural, which is incorporated to aid in the delivery of the active ingredient to the site to be treated and to facilitate storage, transport and handling of the active ingredient compound. Suitable solid carriers include clays such as montmorillonite and kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean flour,
Examples include vegetable organic substances such as sawdust and flour, and urea. Suitable liquid carriers include toluene, xylene,
Aromatic hydrocarbons such as cumene, paraffinic hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, Examples include alcohols such as methanol, propanol, and ethylene glycol, dimethylformamide, dimethyl sulfoxide, and water. In order to further enhance the efficacy of the compounds of the present invention,
Depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.
The following adjuvants can also be used individually or in combination. Water-soluble bases such as lignin sulfonates,
Nonionic surfactants such as alkylbenzene sulfonates and alkyl sulfate esters, lubricants such as calcium stearate and wax, stabilizers such as isopropylhydrodiene phosphate, and other methylcellulose, carboxymethylcellulose,
Examples include casein and gum arabic. However, these components are not limited to the above. The amount of active ingredients in the composition of the compound of the present invention is usually 0.5 to 20% by weight for powders, 10 to 90% by weight for wettable powders,
0.1 to 20% by weight for granules, 5 to 20% by weight for emulsions,
In flowable agents, it is 10 to 90% by weight. [Example] Table 1 shows representative examples of the amide-substituted fluoroethoxyacetonitrile derivatives represented by the general formula () according to the present invention.

【table】

[Table] Next, the method for producing the compound () of the present invention will be specifically explained by giving a synthesis example. Synthesis Example 1 Synthesis of 2-benzoylamino-2-(2-fluoroethoxy)acetonitrile (compound number-1) A solution of 4.0 g of benzoylaminoacetonitrile synthesized from benzoyl chloride and aminoacetonitrile in a conventional manner in 200 ml of ethyl acetate at room temperature. 4.0 g of bromine was added all at once. When the color of bromine in the reaction solution disappears, the reaction solution is brought to 0 to 5°C, and 1.9 g of 2-fluoroethanol and 5.6 g of triethylamine are added.
was dissolved in 10 ml of ethyl acetate, and added dropwise to the previously cooled ethyl acetate solution. After the dropwise addition was completed, the reaction was continued at room temperature for an additional 30 minutes. Triethylamine bromate was filtered off, and the liquid was distilled under reduced pressure to remove the solvent. The residue was purified by isilica gel column chromatography. It was eluted from a hexane-ethyl acetate system to obtain 3.9 g of 2-benzoylamino-2-(2-fluoro)ethoxyacetonitrile as a solid.
Yield 70.3% mp 75-77℃ NMRδ ^CDCl3 _TMS (ppm): 3.70 (1H, m): 4.15 (2H,
m): 4.93 (1H, m): 6.30 (1H, d): 7.2-8.3
(6H, m) Note that the residue after the above-mentioned solvent distillation can be used as it is as a herbicide or fungicide. Synthesis Example 2 2-(3,5-dichloro)benzoylamino-
Synthesis of 2-(2-fluoro)ethoxyacetonitrile (compound number-9) Add bromine to a solution of 4.0 g of 3,5-dichlorobenzoylaminoacetonitrile in 100 ml of ethyl acetate at room temperature.
2.8g was added all at once. After stirring until the color of bromine in the reaction solution disappeared, the reaction solution was cooled to 0 to 5°C. A mixture consisting of 1.3 g of 2-fluoroethanol, 3.5 g of triethylamine, and 20 ml of tetrahydrofuran was cooled to 0 to 5° C. in an ice bath, and the previously prepared ethyl acetate solution of the bromine compound was added dropwise while stirring. After the dropwise addition was completed, the reaction was continued for 30 minutes under ice cooling, and then 100 ml of water was added to dissolve the precipitated triethylamine bromate. Separate the oil layer,
After washing with water and drying, the solvent was distilled off under reduced pressure. The residual solid was suspended in ethyl ether, filtered, washed, and dried to obtain the desired 2-(3,5-dichloro).
3.2 g of benzoylamino-2-(2-fluoroethoxy)acetonitrile was obtained as a white solid. Yield 63.0%. mp 135-138℃ NMRδ ^{CDCl3-DMSO-d6} _TMS (ppm): 3.75 (1H, m):
4.20 (2H, m): 4.98 (1H, m): 6.32 (1H,
d): 7.4-8.0 (3H, m): 9.28 (1H, m) The acylaminonitriles used as starting materials can be easily produced by reacting acyl halides and aminoacetonitrile in a conventional manner. . For example, a 10% aqueous sodium hydroxide solution is cooled in ice water, and aminoacetonitrile sulfate is added and dissolved while stirring. A toluene solution of acid halide is added dropwise to this solution under ice cooling, and after the addition is complete, the mixture is further stirred at the same temperature. The precipitated crystals were collected through a suction port, and the resulting crystals were washed with toene and water, and then dried, and used. Next, the formulation method of the herbicide or agricultural and horticultural fungicide of the present invention will be explained using formulation examples. The active ingredient compounds are shown by compound numbers in Table 1 above. "Part" represents "part by weight." Formulation example 1 Powder Compound (1): 3 parts, diatomaceous earth: 20 parts, white clay: 30
and 47 parts of talc were uniformly ground and mixed to obtain 100 parts of a powder. Formulation example 2 Wettable powder Compound (2): 30 parts, diatomaceous earth: 44 parts, white clay: 20
1 part of sodium ligninsulfonate and 2 parts of sodium alkylbenzenesulfonate were uniformly ground and mixed to obtain 100 parts of a wettable powder. Formulation Example 3 Emulsion 40 parts of compound (3), 10 parts of cyclohexane, 30 parts of xylene, and 20 parts of Solpol (a surfactant manufactured by Toho Chemical Co., Ltd.) were uniformly dissolved and mixed to obtain 100 parts of an emulsion. Formulation Example 4 Granule Compound (4): 1 part, bentonite: 78 parts, talc: 20 parts, and sodium ligninsulfonate:
After mixing 1 part, adding an appropriate amount of water and kneading, the mixture was granulated by a conventional method using an extrusion granulator, and after drying, 100 parts of granules were obtained. Formulation Example 5 Granules Compound (10): 7 parts, polyethylene glycol nonyl phenyl ether: 1 part, polyvinyl alcohol: 3 parts and clay: 89 parts were mixed uniformly, and after hydrogranulation, it was dried to obtain 100 parts of granules. Obtained. Formulation Example 6 Powder 2 parts of compound (6), 40 parts of calcium carbonate, and 58 parts of clay were uniformly ground and mixed to obtain 100 parts of a powder. Formulation Example 7 Wettable powder Compound (5): 50 parts, talc: 40 parts, sodium lauryl phosphate: 5 parts, and sodium alkylnaphthalene sulfonate: 5 parts were mixed to obtain 100 parts of a wettable powder. Formulation example 8 Wettable powder Compound (6): 50 parts, Sodium ligninsulfonate:
10 parts, sodium alkylnaphthalene sulfonate: 5
10 parts of white carbon and 25 parts of diatomaceous earth were mixed and ground to obtain 100 parts of a wettable powder. Formulation example 9 Flowable agent Compound (7): 40 parts, carboxymethylcellulose: 3 parts, sodium ligninsulfonate: 2
1 part of dioctyl sulfosuccinate sodium salt and 54 parts of water were wet ground in a sand grinder to obtain 100 parts of a flowable agent. Next, the efficacy of the compounds of the present invention as herbicides will be explained using test examples. Test Example 1 Pre-emergence weeding test in a rice field Filled with soil in a 1/5000 Ahr Wagner pot, seeds of Japanese millet, broad-leaved weeds (e.g. Kikashigusa, azalea, Japanese cypress, etc.), bulrush, cypress, and cypress were sown, and the pot was submerged in water. Two paddy rice seedlings (2-3 leaf stage) that had been raised in advance were used as one plant, and the two plants were transplanted and grown in a greenhouse. One day after transplanting paddy rice and before the emergence of weeds, a predetermined amount of each test compound was submerged in water using granules prepared according to the method described in Formulation Example 5 above. Thirty days after treatment, weed growth and chemical damage to paddy rice were investigated. The results are shown in Table-2. In the table, the degree of chemical damage to crops and the weed effect on weeds are expressed by comparing the state of emergence or growth of crops or weeds with the air dry weight in the case of no treatment, and according to the evaluation criteria below. The test compounds are shown in the table above.
1 (the same applies hereinafter). Evaluation criteria 0: Survival rate expressed as air dry weight ratio vs. untreated area
91-100% 1: 〃 71-90% 2: 〃 41-70% 3: 〃 11-40% 4: 〃 6-10% 5: 〃 0-5%

[Table] Test Example 2 Rice paddy growing season weed test A/5000 Wagner pots were filled with soil, and seeds of Japanese millet, broad-leaved weeds (Kikashigusa, Azena, Japanese cypress, etc.), bulrush, Japanese cypress, and Japanese cypress were sown and kept in a flooded state. Two paddy rice seedlings (2-3 leaf stage) that had been raised in advance were used as one plant, and the two plants were transplanted and grown in a greenhouse. During the weed growth period 12 days after transplanting paddy rice, a predetermined amount of each test compound was submerged in water using granules prepared according to the method described in Production Example 4 above. process
After 30 days, weed growth conditions and chemical damage to paddy rice were investigated, and the results are shown in Table 3. In this table, the degree of chemical damage to crops and the growth status of weeds were expressed according to the method shown in Test Example 1.

[Table] From Tables 2 and 3, it is clear that the compounds of the present invention do not cause any phytotoxicity to paddy rice as weed agents for paddy fields, and have weed effects against various weeds over a wide range of suitable periods. Moreover, from the information disclosed in JP-A-57-176938, the application of the compound of the present invention as a weed agent for paddy fields is completely unpredictable. Next, the efficacy of the agricultural and horticultural fungicide of the present invention as a fungicide will be explained using test examples. In this section, a comparative test with an amide-substituted allyloxyacetonitrile derivative, which is a compound considered to have a relatively similar structure to the compound according to the present invention, was shown. Test example 3 Potato late blight control test (preventive effect) Potatoes grown in pots in a greenhouse (variety:
A spray gun (1.0 kg/approx. cm ² ) using 50ml per 3 pots
Spread and air dry. 7 on the potato section in advance
A zoospore suspension was prepared from Phytophthora blightum that had been cultured for one day. This suspension was spray inoculated onto the drug-sprayed potato plants, and the test plants were heated to 17-19℃.
After maintaining the humidity at 95% or higher for 6 days, the degree of lesion formation was investigated. The disease severity index was determined by observing and evaluating the lesion area ratio for each leaf, and the disease severity was determined for each plot using the following formula. Morbidity = 4n ₄ +3n ₃ +2n ₂ +1n ₁ +0・n ₀ /〓N The evaluation criteria are as follows. Disease severity index 0: Lesion area ratio 0% 1: 〃 1-5% 2: 〃 6-25% 3: 〃 26-50% 4: 〃 51% or more n ₀ : Number of leaves with disease severity index 0 n ₁ : 〃 1 〃 n ₂ : 〃 2 〃 n ₃ : 〃 3 〃 n ₄ : 〃 4 〃 The results are shown in Table-4.

【table】

[Table] Test example 4 Potato late blight control test (therapeutic effect) Potatoes grown in pots in a greenhouse (variety:
A zoospore suspension of Phytophthora Phytophthora fungi prepared in the same manner as in Test Example 3 was spray inoculated onto a male goat (plant height approximately 25 cm). After maintaining the temperature at 17-19℃ and humidity above 95% for 20 hours, spray a drug at a specified concentration (each test compound was made into a wettable powder using the method of Formulation Example 2 and diluted to a specified concentration). Spraying was performed using a gun (1.0 Kg/cm ² ). After air drying, 17-19℃ again, humidity 95
% or higher for 5 days, the degree of lesion formation was investigated. The evaluation criteria and disease severity display method were as shown in Test Example-3. The results are shown in Table-5.

【table】

[Table] Test Example 5 Downy mildew control test on cucumbers (preventive effect) A predetermined concentration of the drug (formulation example of each test compound) was applied to cucumbers grown in pots in a greenhouse (variety: Sagami Hanshiro, 2 true leaves developed). A hydrating agent prepared by method 2 and diluted with water to a predetermined concentration) was sprayed in 30 ml per three pots using a spray gun (1.0 Kg/cm ² ) and air-dried. Downy mildew bacteria were collected from lesions on cucumber leaves infected with downy mildew, a spore suspension was prepared with demineralized water, and the suspension was sprayed for inoculation. The inoculated pots were immediately kept at 18-20°C and a humidity of 95% or higher for 24 hours, then transferred to a greenhouse (room temperature 18-27°C), and after 7 days, the degree of lesion formation was examined. The evaluation criteria and disease severity display method were as shown in Test Example 3. The results are shown in Table-6.

【table】

[Table] Test Example 6 Downy mildew control test on cucumbers (therapeutic effect) A suspension of downy mildew fungi on cucumbers similar to those used in Test Example 5 was prepared and inoculated by spraying. After maintaining the temperature at 18-20°C for 24 hours and a humidity of 95% or higher, the drug is prepared at a predetermined concentration (each test compound is made into a wettable powder by the method of Example 1, and this is diluted with water to a predetermined concentration). Using a spray gun (1.0 Kg/cm ² ), 30 ml of the mixture was sprayed per 3 pots. Greenhouse (temperature 18-27
After 6 days, the degree of lesion formation was examined. The evaluation criteria and disease severity display method were as shown in Test Example 3. The results are shown in Table-7.

【table】

[Table] As shown in Tables 4, 5, 6 and 7, the compound group of the present invention is effective against zinc ethylene bis(dithiocarbamate) or tetrachloroisophthalate, which is currently commercially available against late blight of potato and downy mildew of cucumber. It is clear that it is effective at an extremely low dose compared to nitrile, and also has therapeutic effects that the above two drugs do not have. The compound group of the present invention is the compound group disclosed in JP-A-57-176938, that is, N-(α-ethoxy-α-cyano)methylbenzamide, N-
(α-ethoxy-α-cyano)methyl-3,4-
Methylenedioxybenzamide or N-{α
It is clear that it has an excellent control effect that cannot be expected from -(2,2,2-trifluoroethoxy)-α-cyano}methyl-4-chlorobenzamide and the like. Test Example 7 Chinese cabbage clubroot disease control test Soil contaminated with clubroot fungi of cruciferous plants 1
Add the powder prepared according to the method of Formulation Example 1 to Kg to a predetermined dose, mix well with the entire amount of soil, and then pack into a pot with a diameter of 18 cm.
20 seeds were sown. The plants were grown in a greenhouse (15 to 28°C), and the diseased state of the roots was examined 7 weeks after sowing. The results are shown in Table-8. Control rate (%) = Number of healthy plants in each treatment area / Number of tested plants in each treatment area x 100

[Table] Commercially available drugs as disinfectants.
As shown in Table 8, it is clear that the compounds of the present invention are highly effective against clubroot disease of cruciferous vegetables. Moreover, the matter disclosed in JP-A-57-176938 is that the application of the compound of the present invention to clubroot disease of cruciferous vegetables is completely unpredictable. Test Example 8 Antibacterial activity test against soil pathogens and others by agar dilution method An agar medium containing a predetermined amount of the compound of the present invention was prepared, and the growth state of pathogens on the medium was observed. The test bacteria are as follows. Phytophthora infestans (PI) Phytophthora parasitica var.parasitica (PP) Pythium debaryanum (PD) Aphanomyces raphani (AR) The results are shown in Table 9. The numerical value indicates the minimum inhibitory concentration (MIC) of the compound against each test bacterium.

[Table] -Methoxyacetylalanine methyl ester <Effects of the invention> As is clear from the above explanation, the production method of the present invention allows the production of the general formula () of the present invention. An amide-substituted fluoroethoxyacetonitrile derivative represented by the formula (wherein A represents an unsubstituted or substituted phenyl group) can be obtained in substantially one step. In addition, the amide-substituted fluoroethoxyacetonitrile derivative according to the present invention can be used as a herbicide for paddy fields in a wide range of periods, and is excellent against paddy weeds, where conventional herbicides have a narrow range of suitable herbicides and cannot be expected to have sufficient herbicidal effects. It exhibits herbicidal action, and as a control agent for diseases caused by algae and fungi on various crops, such as plague and downy mildew, it has a preventive effect at a lower dose than conventional agents, and has a therapeutic effect that conventional agents could not have. It has excellent properties, showing excellent control effects against moawasemochi and soil diseases. Pesticides containing these provide useful herbicides and fungicides for agriculture and horticulture.

Claims (1)

[Claims] 1 General formula () (In the formula, A represents a phenyl group that is unsubstituted or substituted with one or more of a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, or a cyano group, and the substituent may be the same or different if the number is 2 or more. 2 General formula () A-COC1 () (wherein A is unsubstituted or one or more of a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, or a cyano group) (represents a substituted phenyl group, and when the number of substituents is 2 or more, they may be the same or different.) is reacted with aminoacetonitrile to form the general formula () A-CONHCH ₂ Acylaminoacetonitrile represented by CN () (in the formula, A indicates the above meaning) is obtained, and this is treated with a halogenating agent to obtain the general formula (). A general formula () characterized by obtaining an intermediate represented by (wherein A has the above meaning and X represents a halogen atom) and then reacting this with monofluoroethanol. A method for producing an amide-substituted fluoroethoxyacetonitrile derivative represented by the formula (wherein A has the above meaning). 3 General formula () (In the formula, A represents a phenyl group that is unsubstituted or substituted with one or more of a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, or a cyano group, and the substituent 2 or more, they may be the same or different. 4 General formula () (In the formula, A represents a phenyl group that is unsubstituted or substituted with one or more of a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, or a cyano group, and the substituent If the number is 2 or more, they may be the same or different.