JPS62103056A - Acylaminobutenyl derivative, production thereof and herbicide, agricultural and horticultural fungicide containing same - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [A is (substituted) phenyl or naphthyl; R<1> is H or lower alkyl; R<2> and R<3> are H, lower alkyl or halogen]. EXAMPLE:2-(3,5-Dichlorobenzoylamino)-3-pentenonitrile. USE:A herbicide and an agricultural and horticultural fungicide. It has broad application period as a herbicide for paddy field and has low phytotoxicity to paddy rice plant and fish toxicity. It exhibits fungicidal effect against the blight and downy mildew, etc., of various crops and excellent activity to soil blight such as damping-off. PREPARATION:The compound of formula I can be produced by reacting an acid chloride of formula A-COCl with an alpha-aminobutenylnitrile derivative of formula II in the presence of an acid acceptor (e.g. triethylamine) under cooling.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention relates to compounds of the general formula (I) (wherein A represents a phenyl group, a substituted phenyl group or a naphthyl group, and R1 represents a hydrogen atom or a lower alkyl group) , R2 and P each represent a hydrogen atom, a lower alkyl group or a halogen atom), a method for producing the same, and a herbicide for paddy fields or a fungicide for agricultural and horticultural purposes containing them as active ingredients. It is something.

[Prior art]

A great deal of research has been carried out on amide derivatives used in agriculture and horticulture, and many compounds exhibiting characteristic physiological activities have been discovered and put into practical use.

For example, as a W-benzamide derivative, ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate (benzoylprop-ethyl) is used as a herbicide, and 2-methyl-N- (3-isopropoxyphenyl)benzamide (mepronyl) and the like are known.

However, acylaminobutenyl nitrile derivatives and their physiological activities as shown in the present invention are not known.

Chemical Abs
According to the Journal of the Chemical Society (t-racts), there are only a few examples of synthesis of acylaminobutenyl nitrile derivatives and closely related acylamino saturated aliphatic derivatives as shown in the present invention.
J,Chew,Soc,), 1963.2143-2
150 pages, and Synthesis
) 2-benzoylaminobutyronitrile or buretane
Delasociétiques de Français (Bull, S
oc, Chim.

Fr, ) + Tannami, No. 11, pages 4108-4111,
and Justus Liebigs Ann, Chem.
), ■72.764. Pages 69 to 93 give an example of the synthesis of 2-benzoylaminopropionitrile. However, these documents do not mention at all the physiological activities of the compounds described.

Conventionally, 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, but the performance of the amide compound butachlor is still insufficient. 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 treatment is delayed.

All of these herbicides have excellent performance in some respects, so they are widely used and widely used, but their shortcomings and problems have gradually become apparent.
There is a strong need for a new herbicide for rice fields that is easier to use and has superior performance.

On the other hand, compounds with various chemical structures have been used as agricultural and horticultural fungicides, but captafor, TPN, cabtan, or dithiocarbamate drugs are effective against late blight and downy mildew of various crops. It has been widely used and has contributed to increased crop production. However, all of these compounds mainly have a preventive effect against late blight and mildew, and cannot be expected to have any therapeutic effect.
They have a major drawback in that they cannot be expected to be sufficiently effective once disease outbreaks are observed.

In reality, when considering the spraying of chemicals for crop disease control, they are more or less sprayed after the disease appears, and it is difficult to completely control the disease with these compounds.

Furthermore, the concentration of compounds that exhibit pesticidal effects is extremely high, which is also viewed as a problem in terms of the safe use of pesticides. In order to improve these points, research into new insecticides has continued, and currently N-phenylalanine ester derivatives, such as meraxyl (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 due to their drug-resistant bacteria.

[Problem to be solved by the invention]

The present invention overcomes the drawbacks of the prior art described above and provides a compound having extremely excellent properties as a herbicide for paddy fields and a fungicide for agriculture and horticulture, a method for producing the same, and a noxious weed control agent containing the same as an active ingredient. The objective is to provide a harmful microorganism control agent.

In other words, as a herbicide, it can be used throughout the year in paddy fields, has little phytotoxicity to paddy rice, and has low toxicity to fish, and as a fungicide, it has preventive and therapeutic effects on late blight and downy mildew of various crops. New compounds with a wide range of applications that have both of the above and also have an excellent control effect on soil diseases such as seedling damping-off of various crops, simple and high-yielding methods for producing these new compounds, and It is an object of the present invention to provide useful agrochemical compositions containing them.

[Means and effects for solving the invention] As a result of intensive research on acylaminoalkenyl nitrile derivatives to solve the above-mentioned problems, it was found that acylaminobutenyl nitrile derivatives exhibit physiological activities that could not be predicted from the above-mentioned prior art. As a herbicide for rice fields, it has a wide range of suitable periods, and is less harmful to paddy rice and less toxic to fish.As a fungicide, it has preventive and therapeutic effects against late blight and downy mildew of various crops. We have completed the present invention by discovering that the present invention has both of the following and also exhibits excellent control effects against soil diseases such as seedling damping-off of various crops.

The acylaminobutenyl nitrile derivative according to the present invention has the general formula (1) (wherein A represents a phenyl group, a substituted phenyl group, or a naphthyl group, R1 represents a hydrogen atom or a lower alkyl group, and R2 and R3 each represent This is a novel compound represented by a hydrogen atom, a lower alkyl group, or a halogen atom.

When 8 is a substituted phenyl group, examples of the substituent include a halogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a nitro group, and a cyano group. The number of carbon atoms in lower alkyl groups, etc. is 1
~6. When there is a plurality of substituents, II R'% which may be the same or different. When R2 and R1 are lower alkyl groups, the number of carbon atoms is 1 to 6.

Furthermore, as a result of intensive study on the method for producing the acylaminobutenyl nitrile derivative represented by the general formula (1), the present invention was completed by discovering a method for obtaining the desired product in high yield.

That is, the method for producing an acylaminobutenyl nitrile derivative, which is an acylamino derivative according to the present invention, is based on the general formula (I
I) Reacting the acid chloride represented by A-cocl(If) (wherein A has the above meaning) with the α-aminobutenyl nitrile derivative represented by the general formula (T[I)) This is a unique manufacturing method.

The method for producing the compound of the present invention represented by general formula (1) will be explained below using reaction scheme A.

Reaction Scheme A An aldehyde represented by the general formula (tV) is reacted under Schedrecker reaction conditions in the presence of HCN and ammonia to obtain α-7 minoptenyl nitrile derivative (111)6. react with acid chloride (n) in the presence of body. Examples of acid acceptors include organic bases such as triethylamine, dimethylaniline, pyridine, ammonia,
potassium carbonate, sodium carbonate, sodium bicarbonate,
Indefinite bases include, but are not limited to, sodium hydroxide, ammonium carbonate, and the like.

This reaction is preferably carried out in a solvent or diluent; pyridine can be used both as a solvent and as an acid acceptor. In this reaction, the intermediate α-aminobutenyl nitrile has poor thermal stability, so it is not desirable to react at too high a temperature.
Furthermore, since it is an exothermic reaction, it is desirable to carry out the reaction under cooling. The desired acylaminobutenyl nitrile derivative thus obtained can be easily isolated and purified by conventional methods such as recrystallization and column chromatography. In addition,
Due to its chemical structure, the acylaminobutenyl nitrile derivative represented by the general formula N) obtained by the production method according to the present invention has the following properties:
Regarding the double bond, it may contain two types of geometric isomers, 2 and E, but these geometric isomers can be easily separated and purified by column chromatography or the like.

Furthermore, the present invention provides a herbicide for paddy fields and a fungicide for agriculture and horticulture, which contain the acylaminobutenyl nitrile 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 fields, the amount applied will vary 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 it is usually 0 per area. ．．
1 to 100g is appropriate, preferably 0.0g per area.
It is 5-25g. Its herbicidal activity is characteristically strong against grass weeds, but it also shows a strong suppressive effect on other weeds, although the degree varies depending on the type.

Weeds of the Cyperaceae family, for example Cyperaceae, are particularly strongly suppressed. Such properties are extremely advantageous when considering mixed application with conventional agents that are weak against grass weeds, such as in mixtures or tank mixes.

In addition, the application period of the compound of the present invention is much broader than that of the known amide compound butachlor and thiol carbamate compound bentiocarb, which have a wide range of application timing from before the emergence of weeds to the growing season. It has excellent characteristics that have not been seen before, and can be an easy-to-use herbicide with fewer restrictions on treatment timing. Although the practical dose of herbicidal activity against Japanese millet naturally depends on the treatment period, Bentocarb and butachlor are insufficiently effective at practical doses against Japanese millet at the 3.5 leaf stage, whereas 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 diseases caused by various other plant pathogenic fungi. It is also effective. Moreover, it has both preventive and therapeutic effects.

The main diseases to be controlled are potato late blight, tomato late blight, tobacco late blight, locust late blight, adzuki bean stem blight, grape rot, cucumber rot, hoppe rot, shungikube rot, and various diseases caused by Acupnomyces sp., Bicillum sp. One example is crop seedling damping-off.

Methods for applying the compound of the present invention include seed disinfection, foliage spraying,
Examples include soil treatment, but any application method commonly used by those skilled in the art will exhibit sufficient efficacy. The amount and concentration of application will vary depending on the target crop, target disease, degree of disease occurrence, dosage form of the compound, application method, various environmental conditions, etc., but when spraying, 5 to 200 g
g is suitable, preferably 10 to 100 g per are.
It is. The spraying concentration is 20-1, OOOppm
is suitable, preferably 50 to 500 pp-.

The herbicides and agricultural and horticultural fungicides of the present invention can of course be used in combination with other fungicides, insecticides, herbicides, agricultural chemicals such as plant growth regulators, soil conditioners, or fertilizing substances. Mixed preparations are also possible.

The compounds of the invention may be applied as such, but are preferably applied in the form of a composition mixed with a carrier, including a solid or liquid diluted carrier. means an inorganic or organic substance, synthetic or natural, that is incorporated to aid in the access of ingredients or to facilitate the storage, transport and handling of active ingredients.

Suitable solid carriers include clays such as montmorillonite and kaolinite; inorganic substances such as diatomaceous earth, clay, curcum, vermiculite, gypsum, calcium carbonate, silica gel, and ammonium sulfate; vegetable organic substances such as soybean flour, sawdust, and wheat flour; and urea.

Suitable liquid carriers include aromatic hydrocarbons such as toluene, quinolene, and cumene; paraffinic hydrocarbons such as kerosene and mineral oil; halogenated hydrocarbons such as carbon tetrachloride, chloroform, and dichloroethane; acetone, methyl ethyl ketone, etc. ketones; ethers such as dioxane and tetrahydrofuran; alcohols such as methanol, propatool, and ethylene glycol; dimethylformamide; dimethyl sulfoxide; and water.

Furthermore, in order to enhance the efficacy of the compound of the present invention, various adjuvants may be used individually or in combination depending on the purpose, taking into account the dosage form of the preparation, the application situation, etc.For example, emulsification, For purposes of dispersion, spreading, wetting, binding, stabilization, etc., water-soluble bases such as lignin sulfonates; anionic surfactants such as alkylbenzene sulfonates; alkyl sulfate esters, polyoxyalkylene alkyl Ether, polyoxyalkylene alkylaryl ether, polyoxyalkylene alkyl amine, polyoxyalkylene alkyl amide, polyoxyalkylene alkyl thioether, polyoxyalkylene fatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxy Nonionic surfactants such as propylene polyoxyethylene block polymers; lubricants such as calcium stearate and wax; stabilizers such as isopropylhydrodiene phosphate; and other additives such as methylcellulose, carboxymethylcellulose, casein, and gum arabic. be done. However, it goes without saying that the use is not limited to these.

The amount of active ingredient in the composition of the compound of the present invention is usually 0 when used as a powder.
．． 5 to 2% by weight, emulsions from 5 to 30% by weight, wettable powders from 10 to 90% by weight, granules from 0.1 to 20% by weight, and flowables from 10 to 9% by weight.

〔Example〕

Representative examples of the acylaminobutenyl nitrile derivatives represented by the general formula (T) according to the present invention are shown in Table-1.

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-(3,5-dichlorobenzoylamino)-3-pentenonitrile (Compound No.-4) 10.0 g of ammonium fluoride, 6.0 g of sodium cyanide, and 50 g of water
151.28% ethyl ether and 10% aqueous ammonia were added thereto. Cool to 5°C in a water bath,
Crotonaldehyde 7 and Og were added dropwise under the pressure of a, and the mixture was further stirred at the same temperature for 24 hours. After the reaction was completed, the ether layer was separated, and the aqueous layer was extracted with ether three times. The ether layers were combined and dried over sodium sulfate. . The ether layer was concentrated under reduced pressure, and 100 ml of ethyl ether was added to the residue.
Cooled to ~5°C.

Next, after adding 5.1 g of triethylamine, 6.2 g of 3.5-dichlorobenzoyl chloride was added dropwise while stirring. After the dropwise addition was completed, stirring was continued at the same temperature for an additional hour.

50 ml of water was added to dissolve the precipitated triethylamine hydrochloride. The ether layer was separated, washed with water, dried, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography.

Elute from hexane-ethyl acetate system to obtain the desired 2-(3,
4.8 g of 5-dichlorobenzoylamino)-3-pentenonitrile was obtained as a white solid. Yield 56.8%m,
p, 109-111°C NMRδCII”x (ppm): 1.76 (31+, d
), 5.3-6.5 (3H, m), 9.2 (IH, d)
, 7.4-7.8 (3H, m) Synthesis Example 2 Synthesis of 2-(3,5-dichlorohensyylamino)-4-methyl-3-pentenonitrile (Compound No. 27) Ammonium chloride 8°3g1 Sodium cyanide 5.0
Dissolve g in water SOn+1 and add ethyl ether 15
ml, 8 nl of 28% aqueous ammonia was added. In the water bath 5
7. Cool to 0.degree. C. and add 3-methyl-2-butynal under stirring.
0 g was added dropwise, and the mixture was further stirred at the same temperature for 24 hours.

After the reaction was completed, the ether layer was separated, the aqueous layer was extracted with ether three times, and the ether layers were combined and dried over sodium sulfate. The ether layer was heated under reduced pressure for 74 m, 100 ml of ethyl ether was added to Ml, and the mixture was cooled to 0 to 5°C.

Next, 4.2 g of triethylamine was added, and 5.2 g of di-3,5-dichlorobenzoyl chloride was added dropwise while stirring. After completion of the dropwise addition, stirring was continued at the same temperature for an additional hour.

50 ml of water was added, and the precipitated triethylamine hydrochloride was filtered off with suction, and the filtrate was distilled under reduced pressure to remove the solvent. The residue was recrystallized from hexane-ethyl acetate system to obtain the desired 2-
(3,5-dichlorobenzoylamino)-4-methyl-
4.7 g of 3-pentenonitrile was obtained. Yield 63.0% m, p, 92-94°C δ””3 (ppm): 1.93 (6H, s), 5.3
~6.0 (2H, +*) Mj 7.4 ~ 8.1 (48, m) Synthesis Example 3 2-(3,5-dichlorobenzoylamino)-4-chloro-3-pentenonitrile (compound no. 39 and 42
) Synthesis of ammonium chloride 6.7g, sodium cyanide 4.0
Dissolve g in 50 ml of water and add 15 ml of ethyl ether to this.
7 ml of 28% ammonia water was added. 5℃ in water bath
7.0% of 3-chloro-2-butinal under stirring.
g was added dropwise thereto, and the mixture was further stirred at the same temperature for 12 hours.

After the reaction was completed, the ether layer was separated, the aqueous layer was extracted with ether three times, and the ether layers were combined and dried over sodium sulfate. The ether layer was concentrated under reduced pressure, 50 ml of tetrahydrofuran was added to the residue, and the mixture was cooled to 0 to 5°C. Then, 3.4 g of triethylamine was added, and 3.5 ml of tetrahydrofuran was added to the residue with stirring.
After 0 dropwise addition of 4.2 g of -dichlorobenzoyl chloride, stirring was continued at the same temperature for an additional hour. The precipitated triethylamine hydrochloride was separated by suction filtration, and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Eluted from hexane-ethyl acetate system, 1.6 g (yield 32.9%) of 8 desired 2-(3,5-dichlorobenzoylamino)-4-chloro-3-pentenonitriles (compound number 39) , 2 bodies (
Compound No. 42) 2.1 g (yield 42.6%) was obtained.

8-body (compound number 39) n, p, 127 ~ 130'C δCDCl3-DH3°-6≦(ppm): 2.17
(3)1. s), 5.81 (2H, dd), 7.4 ~
7.9 (3H, m), 9.1 (LH, d) 2 bodies (compound number 42) m, p, 150-152°C δ"cFj -""-'l (ppm): 2.17 (3
H, s), 5.82 (2H, dd), 7.4-7.9 (3)1, m), 9. Hllll, d) Note that: 3-chloro-2-butinal used as a raw material was published in the Journal of Organic Chemistry (J, Or.
g, Chem, ), vol, 30.1126 (19
65)".

Next, the method for producing the herbicide for paddy fields or the fungicide for agriculture and horticulture of the present invention will be explained using formulation examples.

The active ingredient compounds are shown by the compound numbers in Table 1 above, and "parts" are "parts by weight."

Formulation Example 1 Powder compound +11: 3 parts, diatomaceous earth: 20 parts, white clay:
30 parts 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: 47 parts, clay: 20 parts, sodium ligninsulfonate: 1 part, and sodium alkylbenzenesulfonate: 2 parts were uniformly ground and mixed to make a wettable powder of 100 parts. I got the department.

Formulation Example 3 20 parts of emulsion compound +31, 10 parts of cyclohexanone, 50 parts of xylene, and 20 parts of Tulpol (surfactant manufactured by Toho Chemical Co., Ltd.) were uniformly dissolved and mixed to obtain 100 parts of an emulsion.

Formulation Example 4 Granule compound (4171 parts, bentonite: 78 parts, talc:
20 parts and sodium ligninsulfonate: 1 part were mixed, an appropriate amount of water was added and kneaded, and the mixture was granulated in a conventional manner using an extrusion granulator, and after drying, 100 parts of granules were obtained.

Formulation Example 5 017 parts of a granule compound, 1 part of polyethylene glycol nonylphenyl ether, 3 parts of polyvinyl alcohol, and 289 parts of clay were uniformly mixed, hydrogranulated, and dried to obtain 100 parts of granules.

Formulation Example 6 Powder Compound 161: 2 parts, calcium carbonate = 40 parts, and clay = 58 parts were uniformly mixed to obtain 100 parts of a powder.

Formulation Example 7 Wettable powder Compound +51: 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 lignin sulfonate, 210 parts, alkylnaphthalene sulfonium = 5 parts, white carbon: 10 parts, diatomaceous earth: 25 parts were mixed and ground, and 100 parts of the wettable powder was added. Obtained.

Formulation Example 9 Flowable agent Compound +71: 40 parts, carboxymethyl cellulose: 3 parts, sodium ligninsulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part and 54 parts of water were wet-pulverized with a sand grinder to form 100 parts of a flowable agent. I got it.

Next, the efficacy of the compounds of the present invention as herbicides and as insecticides for agriculture and horticulture will be specifically explained using test examples. In addition, the following compounds were used as controls in the test examples.

Control compound A: 2-benzoylaminopropionitrile Bl-benzoylaminobutyronitrile C: 2-chloro-2°. 6
゛-Diethyl-N-(butoxymethyl)acetanilide [butachlor] D-diethylthiocarbamate S-p
-Chlorobenzyl [benthiocarb] E: Zinc ethylene bis(dithiocarbamate) [Zineb] F: Tetrachloroisophthalonitrile (TPN) Control compounds A and B are compounds known in the above-mentioned literature, and C is a pre-development treatment. As a herbicide for paddy fields, D is a commercially available herbicide for paddy fields for treatment during the growing season. E and F are commercially available herbicides for potato late blight, cucumber rot, etc.

Test Example 1 Pre-emergence weeding test in a rice field Pack soil into an R 15,000 Wagner pot, sow seeds of Japanese grasshopper, broad-leaved weeds (Kikashigusa, Azena, Konagi, etc.), firefly, Helaomodaka, and Kumagayari.
It was in a flooded state. Paddy rice seedlings (2
~3-leaf stage) were used as one plant, and the two plants were transplanted and grown in a greenhouse. One day after transplanting paddy rice and before weeds emerged, a predetermined amount of the test compound was submerged in water using granules prepared according to the method described in Formulation Example 5 above. Thirty days after the 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 herbicidal effect on weeds are expressed by comparing the emergence or growth of crops or weeds with that of the untreated air-dried type according to the evaluation criteria below. The test compounds were indicated by compound numbers in Table 1 above (the same applies hereinafter).

Evaluation criteria 0: Survival rate expressed as air dry weight ratio vs. untreated area 91-100χ1:
71~90χ2:
41~70χ3:
11~40χ4: 6
~IOX52 0~5z
jJ1' Experimental Example 2 Rice paddy growing season weeding test R 15,000 Wagner pots were filled with soil, and seeds of Japanese millet, broad-leaved weeds (Kikashigusa, Azena, Konagi, etc.), firefly, Helaomodaka, and Kumagayari were sown,
It was in a flooded state. Two paddy rice seedlings (2-3 leaf stage) that had been grown 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 the test compound was submerged in water using granules prepared according to the method described in Formulation Example 4 above. Processing 30
A day later, weed growth and chemical damage to paddy rice were investigated. The results are shown in Table-3.

In the table, the degree of chemical damage to crops and the growth status of weeds are expressed according to the method shown in Test Example 1.

From the results shown in Tables 2 and 3, it is clear that the compounds of the present invention can be used both in pre-emergence treatments against various harmful weeds that are a problem in rice fields, and in treatments during the growing season where it has been difficult to achieve herbicidal effects. It is clear that it is an excellent compound that exhibits a wide range of herbicidal activities and has almost no phytotoxicity to paddy rice.

In addition, the two compounds described in the above-mentioned document whose chemical structures are relatively similar
-benzoylaminopropionitrile, 2-benzoylaminobutyronitrile, etc. have almost no herbicidal effect, and it is clear that the compounds of the present invention have excellent properties that could not be expected based on any previous knowledge.

Test Example 3 Potato late blight control test Potatoes (variety: Baron, plant height approximately 251) grown in pots in a greenhouse were treated with a predetermined concentration of the drug (test compound) to prepare a wettable powder according to the method of Formulation Example 8 above. , diluted with water to a predetermined concentration) with a spray gun (1.0 g/
ci) was used to spray 50ml per 3 pots and air dry.

A zoospore suspension was prepared from Potato Phytophthora blight which had been previously cultured on potato sections for 7 days. This suspension was spray inoculated onto the potato plants sprayed with the drug, and the test plants were kept at 17-19°C and humidity of 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.

The evaluation criteria are as follows.

Disease severity index 0: Lesion area ratio 0χl: 1~5z 2: 6~25χ 3: 〃26~50χ 4: 4512 or more no: Number of leaves with disease severity index 0 n, HHl #n,: #2 〃n : 〃 3 〃 n, , H4If N” nl + nI + nl + n2 +
The na results are shown in Table 4.

Test Example 4 Cucumber and disease control test Cucumbers grown in pots in a greenhouse (Product N: Sagami Hanshiro, 2 leaves, 2 to 3 plants per pot) were treated with a prescribed concentration of the drug (test compound in the formulation example above). Prepare a hydrating powder according to method 8 and dilute it with water to the specified concentration)
Using a spray gun (1.0 kg/aJ), 30 ml of the material was applied to each of three pots and air-dried. Downy mildew bacteria were collected from diseased spots on leaves of Chie cucumber infected with downy mildew, a spore suspension was prepared with demineralized water, and the suspension was inoculated by spraying. The inoculated pots were immediately kept at 18-20° C. and a temperature 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 results are shown in Table-5.

The evaluation criteria and disease severity display method were as shown in Test Example 3.

The results shown in Tables 4 and 5 show that the compounds of the present invention are significantly more effective than commercially available insecticides that have been widely used in the past against plant diseases caused by algal fungi, such as potato late blight and cucumber blight. It is clear that it has a high pesticidal effect.

In addition, 2-benzoylaminopropionitrile described in the above-mentioned literature, which has a relatively similar chemical structure, or 2-
Benzoylaminobutyronitrile has almost no disease control effect, and it is clear that the compound of the present invention has excellent properties that could not be expected based on any previous knowledge.

[Effects of the Invention] As is clear from the above explanation, the acylaminobutenyl nitrile derivative according to the present invention has an excellent herbicidal effect as a herbicide for rice fields with a wide range of suitable periods, which was not expected with conventional herbicides. In addition, as an agricultural and horticultural fungicide, it has excellent control effects against various diseases caused by algae and fungi on various crops, including soil diseases, at a low dose and concentration, where conventional commercially available drugs cannot be expected to be effective. . The agricultural chemical containing the acylaminobutenyl nitrile derivative according to the present invention has excellent properties and is useful as a herbicide and a fungicide for agriculture and horticulture.

Claims (4)

[Claims] (1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a phenyl group, substituted phenyl group, or naphthyl group, and R^1 represents a hydrogen atom or a lower alkyl group. and R^2 and R^3 each represent a hydrogen atom, a lower alkyl group, or a halogen atom). (2) A patent claim in which, in general formula (I), A is a phenyl group 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. range 1
The acylaminoptenyl nitrile derivative described in Section 1. (3) Acid chloride represented by general formula (II) A-COCl(II) (in the formula, A represents a phenyl group, substituted phenyl group, or naphthyl group) and general formula (III) ▲Mathematical formula, chemical formula, table, etc. ▼(III) (In the formula, R^1 represents a hydrogen atom or a lower alkyl group, and R^2 and R^3 represent a hydrogen atom, a lower alkyl group, or a halogen atom, respectively.) General formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (I) (In the formula, A, R^1, R^2 and R^3 are respectively the above-mentioned A method for producing an acylaminoptenyl nitrile derivative represented by (4) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, A represents a phenyl group, substituted phenyl group, or naphthyl group, and R^1 represents a hydrogen atom or a lower alkyl group. and R^2 and R^3 each represent a hydrogen atom, a lower alkyl group, or a halogen atom) as an active ingredient. disinfectant.