JPH0655705B2 - Acylaminovaleronitrile derivatives, a method for producing the same, herbicides and agricultural / horticultural fungicides containing them - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention provides compounds represented by general formula (I) (In the formula, A represents a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, a furyl group, a substituted furyl group, a thienyl group, a substituted thienyl group or a naphthyl group), and an acylaminovaleronitrile derivative thereof, The present invention relates to a production method and a paddy field herbicide or an agricultural and horticultural fungicide containing them as an active ingredient.

[Prior art]

Many studies have been conducted on amide derivatives useful in agriculture and horticulture, and many compounds showing characteristic physiological activity have been found and put to practical use. For example, as a substituted benzamide derivative, ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate (benzoylpropethyl) is used as a herbicide, and 2-methyl-N- (3 is used as a fungicide. -Isopropoxyphenyl) benzamide (mepronil) and the like are known.
However, nothing is known about the acylaminovaleronitrile derivatives as shown in the present invention and their physiological activity.

According to Chemical Abstracts, there are only a few examples of the synthesis of acylamino saturated aliphatic derivatives closely related to the acylaminobutenylnitrile derivative as shown in the present invention. For example, Journal of the Chemical Society (J.Chem.Soc.), 19
63 , pages 2143 to 2150, and Synthesis, 1972 , No. 11, pages 622 to 624, 2-benzoylaminobutyronitrile, or Bulletin de la Societe Simique Francais (Bull.Soc.Chim). .Fr.), 1969 , No. 11, 4108
~ 4111 pages, and Justus Liebigs Ann.Che
m.), 1972 , 764, pp. 69-93 exemplifies the synthesis of 2-benzoylaminopropionitrile. However, these references do not mention the physiological activity of the compounds described.

Conventionally, many herbicides such as amide compounds, thiol carbamate compounds, and diphenyl ether compounds have been developed and put to practical use as herbicides for paddy fields, but their performance is still insufficient. The amide compound butachlor is used before and after rice planting, but phytotoxicity to rice caused by temperature conditions and the like has always been a problem. The use of thiol carbamate compound molinate is regulated due to the problem of fish toxicity. Bench-o-curve has a problem of chemical damage to paddy rice under reducing conditions of soil.

Although diphenyl ether compounds are used immediately after rice planting like butachlor, their activity becomes extremely low when the treatment time is delayed.

All of these herbicides are widely used in practice because they have excellent performance in one aspect, and are used, but defects and problems are gradually becoming apparent,
There is a strong demand for new herbicides for paddy fields that have superior performance and are easier to use.

On the other hand, compounds having various chemical structures have been put to practical use as agricultural and horticultural fungicides, but captafol, TPN, captan, or dithiocarbamate drugs are used for plague and downy mildew of various crops. It is widely used and has contributed to increased crop production. However, all of these compounds have a prophylactic effect against plague and downy mildew, and no therapeutic effect can be expected at all. For that reason,
It has a major drawback that a sufficient effect cannot be expected when the occurrence of disease is recognized. Considering the actual application of chemicals for controlling crop diseases, the chemicals will be applied more or less after the occurrence of the disease, and complete disease control is difficult with these compounds.

In addition, the concentration of the compound having a controlling effect is also extremely high, which is regarded as a problem from the safe use of the controlling agent. In order to improve these points, research on new control agents has been earnestly continued, and at present, N-phenylalanine ester derivatives, such as metalaxyl [N- (2,6-dimethylphenyl) -N-], which also show excellent therapeutic effects. (2'-methoxyacetyl) alanine methyl ester] and the like have been developed and are being put to practical use worldwide. However, drug resistance of these N-phenylalanine ester derivatives has already been regarded as a problem.

[Problems to be Solved by the Invention]

The present invention overcomes the drawbacks of the prior art described above, a compound having extremely excellent properties as a herbicide for paddy fields and a fungicide for agricultural and horticultural use, its production method and harmful weed control agents containing them as active ingredients and harmful An object is to provide a microbial control agent.

In other words, as a herbicide, it has a wide suitable period for paddy fields, has little phytotoxicity to paddy rice, and has low fish toxicity. As a fungicide, it has prophylactic and therapeutic effects against epidemics and downy mildews of various crops. A new compound having a broad application range, which has both of them and has an excellent control effect against soil diseases such as seedling wilting of various crops, a simple and high-yield method for producing the novel compound, and them. An object of the present invention is to provide a useful agrochemical composition containing

[Means and Actions for Solving the Problems]

As a result of diligent research on an acylaminoalkylnitrile derivative to solve the above-mentioned problems, the acylaminovaleronitrile derivative has a physiological activity that cannot be predicted at all from the prior art, and as a paddy herbicide, It has a wide suitable period, less phytotoxicity to paddy rice, and low fish toxicity. On the other hand, as a fungicide, it has both preventive and therapeutic effects against epidemics and downy mildews of various crops. The present invention has been completed by finding that it also exhibits an excellent control effect against soil diseases such as seedling blight of crops.

The acylaminovaleronitrile derivative according to the present invention has the general formula (I) (Wherein A represents a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, a furyl group, a substituted furyl group, a thienyl group, a substituted thienyl group or a naphthyl group).

The present invention has further earnestly studied a novel method for producing an acylaminovaleronitrile derivative represented by the general formula (I), and as a result, has found a method for obtaining a target product in high yield and completed the present invention.

That is, the method for producing an acylaminovaleronitrile derivative, which is an acylamino derivative according to the present invention, comprises the acid chloride represented by the general formula (II) A-COCl (II) (wherein A represents the above meaning). Formula (III) A method for producing an acylaminovaleronitrile derivative represented by the general formula (I), which comprises reacting with α-aminovaleronitrile represented by

The method for producing the compound of the present invention represented by the general formula (I) will be described below with reference to a reaction scheme.

Reaction scheme (In the formula, A has the above-mentioned meaning.) N-Butyraldehyde is reacted with HCN to obtain α-hydroxyvaleronitrile, and further treated with ammonia to obtain α-aminovaleronitrile. This is then reacted with acid chloride (II) in the presence of acid acceptor.
Examples of acid acceptors include, but are not limited to, organic bases such as triethylamine, dimethylaniline, pyridine, and inorganic bases such as ammonia, potassium carbonate, sodium carbonate, sodium hydrogen carbonate, sodium hydroxide, ammonium carbonate. Not something. This reaction is preferably carried out in a solvent or diluent. Pyridine can be used as both a solvent and an acid acceptor. This reaction is an intermediate α
Since the thermal stability of -aminovaleronitrile is not good, the reaction at a very high temperature is not desirable, and since it is an exothermic reaction, it is desirable to perform it under cooling. The desired acylaminovaleronitrile derivative thus obtained can be easily isolated and purified by a conventional method such as recrystallization or column chromatography.

Furthermore, the present invention provides a paddy field herbicide and agricultural and horticultural fungicide characterized by containing the acylaminovaleronitrile derivative represented by the general formula (I) according to the present invention as an active ingredient. is there. When the compound of the present invention is used as a herbicide for paddy fields, its application amount varies depending on the growth stage of weeds, the type of weeds, the dosage form of the formulation, the application method and various environmental conditions, etc. -10
0g is suitable, preferably 0.5 to 25g per are
Is. Its herbicidal activity is characteristically strong against grass weeds and also against other weeds, and shows a strong inhibitory effect even when they are not killed. On the contrary, such characteristics are advantageous when considering the mixed application with a conventional agent weak against grass weeds or a mixed agent such as a tank mix. In particular, similar tendencies are observed with respect to weeds of Cyperaceae, for example, cyperus edulis, firefly, and the like, although there are strengths depending on the types of other weeds.

Further, the application period of the compound of the present invention varies widely from before the emergence of weeds to the growing season. Compared with the known amide compound butachlor and thiol carbamate compound Benchiocarb, the compound of the present invention has a much wider suitable period of use, and has excellent characteristics not present in the prior art, and there are few restrictions on the treatment time. Can be an easy-to-use herbicide. The herbicidal activity against Taenia japonicum naturally varies in practical dose depending on the treatment time, but Bentocarb and butachlor are insufficiently effective in practical dose in the 3.5 leaf stage Taenia japonica, whereas the compound of the present invention is Amounts below those practical doses show sufficient activity to withstand practical use.

The compound of the present invention has a very low phytotoxicity to transplanted paddy rice regardless of the treatment time.

When using the compound of the present invention as an agricultural and horticultural fungicide,
It is effective not only against plague and downy mildew of various crops caused by algae, but also against diseases caused by other various plant pathogenic fungi.
Moreover, it has both preventive and therapeutic effects.

Major diseases to be controlled are potato disease, tomato disease, tobacco disease, strawberry disease, adzuki bean disease, grape downy mildew, cucumber downy mildew, hop downy mildew, sungiku downy mildew, or Aphanomyces spp., Pythium spp. Examples include various crop seedling blight caused by fungi and the like.

As a method of applying the compound of the present invention, seed disinfection, foliage spray,
Soil treatment and the like can be mentioned, but any application method usually used by those skilled in the art is sufficiently effective. The applied amount and applied concentration are target crop, target disease, degree of disease occurrence,
It varies depending on the formulation of the compound, the method of application and various environmental conditions, but when sprayed, it is 5 to 200 g per are.
Is suitable, and is preferably 10 to 100 g per are. A suitable spray concentration is 20 to 1,000 ppm, preferably 50 to 500 ppm.

Herbicides and agricultural and horticultural fungicides of the present invention include other fungicides and insecticides, herbicides, plant growth regulators and other pesticides, as well as mixed use with soil improvers or fertilizers, with these, Mixed preparations of are also possible.

The compounds of the present invention may be applied as such, but are preferably applied in the form of a composition in admixture with a carrier including a solid or liquid diluent. As used herein, the term carrier means a synthetic or natural inorganic or organic substance that is formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transportation, 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, sawdust, plant organic substances such as flour, and the like. Examples include urea.

Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene and cumene, paraffin 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, alcohols such as methanol, propanol and ethylene glycol, dimethylformamide, dimethylsulfoxide and water.

Further, in order to enhance the efficacy of the compound of the present invention, the following auxiliary agents can be used alone or in combination according to the purpose in consideration of the dosage form of the preparation, the application scene and the like.

For the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc., water-soluble bases such as lignin sulfonate, nonionic surfactants such as alkylbenzene sulfonate, alkyl sulfate, calcium stearate, wax etc. Lubricants, stabilizers such as isopropylhydrodiene phosphate, and others such as methyl cellulose, carboxymethyl cellulose, casein, and gum arabic. However, these components are not limited to the above.

The amount of the active ingredient in the composition of the compound of the present invention is usually 0 in powder.
5-20% by weight, 5-30% by weight for emulsions, 10-90% by weight for wettable powders, 0.1-20% by weight for granules, 10-90% by weight for flowable agents.

〔Example〕

Representative examples of the acylaminovaleronitrile derivative represented by the general formula (1) according to the present invention are shown in Table-1.

Next, the method for producing the compound of the present invention will be specifically described with reference to synthetic examples.

Synthesis Example 1 Synthesis of 2- (3-dichlorobenzoylamino) valeronitrile (Compound No.-2) 1-1. Synthesis of α-aminovalerotonitrile 250 g of n-butyraldehyde and 0.18 g of sodium acetate
Was added, and the mixture was cooled to 0 to 5 ° C in an ice bath. HCN under stirring
133m is dripped in about 1 hour, and further 12 hours,
Stirring was continued at the same temperature. After introducing nitrogen gas all day and night to drive off excess HCN, 800 m of methanol was added, the internal temperature was cooled to -10 ° C in a dry ice-methanol bath, and 400 m of liquid ammonia was added. 0-5 ° C
The mixture was stirred for 4 hours. Excess ammonia and methanol were removed under reduced pressure to give crude α-aminovaleronitrile 28
6 g was obtained. This was used for the next reaction without further purification operation.

1-2. Synthesis of 2- (3-chlorobenzoylamino) valeronitrile (Compound No.-2) 5.0 g of α-aminovaleronitrile obtained in 1-1 is dissolved in 50 m of ethyl ether and cooled to 0-5 ° C. did. After adding 6.1 g of triethylamine, 8.8 g of m-chlorobenzoyl chloride was added dropwise with stirring. After completion of dropping, the mixture was further stirred at the same temperature for 1 hour. 50m of water was added to dissolve the precipitated triethylamine hydrochloride. Separate the ether layer,
After washing with water and drying, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography. Elution from a hexane-ethyl acetate system to give the desired 2- (3-chlorobenzoylamino) valeronitrile as a solid, 6.7 g.
Obtained. Yield 56.6%.

Synthesis Example 2 Synthesis of 2- (3-methoxybenzoylamino) valeronitrile (Compound No. -20) 5.0 g of α-aminovaleronitrile obtained in 1-1 was dissolved in 100 m of tetrahydrofuran and cooled to 0 to 5 ° C. 10.0 g of potassium carbonate was added, and 8.5 g of m-methoxybenzoyl chloride was added dropwise with stirring. 3 more after dropping
Stir for hours. The precipitated crystals were separated and the solution was distilled under reduced pressure to remove the solvent. The residue was recrystallized from cyclohexane to give the desired 2- (3-methoxybenzoylamino)
7.2 g of valeronitrile was obtained as a white solid. Yield 62.0
%.

Next, the method for producing the paddy field herbicide or agricultural / horticultural fungicide of the present invention will be described with reference to formulation examples.

The active ingredient compounds are shown by the compound numbers in Table 1 above.
"Part" means "part by weight".

Formulation Example 1 Dust Compound (1): 3 parts, diatomaceous earth: 20 parts, white clay: 30 parts and talc: 47 parts are uniformly pulverized and mixed to obtain Dust 10
I got 0 copies.

Formulation Example 2 Wettable powder Compound (2): 30 parts, diatomaceous earth: 44 parts, clay: 20
Parts, sodium ligninsulfonate: 1 part and sodium alkylbenzenesulfonate: 2 parts were uniformly pulverized and mixed to obtain 100 parts of a wettable powder.

Formulation Example 3 Emulsion Compound (3): 20 parts, cyclohexanone: 10 parts, xylene: 50 parts and Sorpol (surfactant manufactured by Toho Kagaku Co., Ltd.) 20 parts were uniformly dissolved and mixed to obtain 100 parts of an emulsion.

Formulation Example 4 Granules Compound (4): 1 part, bentonite: 78 parts, talc: 2
0 parts and 1 part of sodium lignin sulfonate were mixed, an appropriate amount of water was added and kneaded, and then granulated by an ordinary method using an extrusion granulator and dried to obtain 100 parts of granules.

Formulation Example 5 Granules Compound (10): 7 parts, polyethylene glycol nonylphenyl ether: 1 part, polyvinyl alcohol: 3 parts and clay: 89 parts are uniformly mixed, hydrolyzed and dried to obtain 100 parts of granules. It was

Formulation Example 6 Dust Compound (6): 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 (5): 50 parts, talc: 40 parts, sodium lauryl phosphate: 5 parts, sodium alkylnaphthalenesulfonate: 5 parts were mixed to obtain 100 parts of a wettable powder.

Formulation Example 8 Wettable powder Compound (6): 50 parts, sodium lignin sulfonate:
10 parts, sodium alkylnaphthalene sulfonate: 5
Parts, white carbon: 10 parts, and diatomaceous earth: 25 parts were mixed and pulverized to obtain 100 parts of a wettable powder.

Formulation Example 9 Flowable agent Compound (7): 40 parts, carboxymethyl cellulose: 3
Parts, sodium lignin sulfonate: 2 parts, dioctyl sulfosuccinate sodium salt: 1 part and 54 parts of water are wet-ground with a sand grinder to give a flowable agent 10
I got 0 copies.

Next, the efficacy of the compound of the present invention as a herbicide and an agricultural / horticultural fungicide will be described with reference to Test Examples. In the test examples, the following compounds were used as controls.

Control compound A: benzoylaminopropionitrile B: 2-benzoylaminobutyronitrile C: 2-chloro-2 ', 6'-diethyl-N- (butoxymethyl) acetanilide [butachlor] D: diethylthiocarbamic acid s- p-chlorobenzyl [benchocarb] E: zinc ethylene bis (dithiocarbamate) [dineb] F: tetrachloroisophthalonitrile [TPN] Control compounds A and B are compounds known in the above literature, and C is generated. For pretreatment, D is a commercially available herbicide for paddy field treatment for growing season. E and F are commercially available agents for controlling potato epidemics and cucumber downy mildew.

Test Example 1 Pre-emergence weeding test Earl / 5000 Wagner pots were filled with soil, and seeds of rice barley, broad-leaved weeds (Cygnus serrata, azena, eel, etc.), firefly, Heraomodaka, and Tamagaya periwinkle were sown,
It was flooded. Two rice seedlings (2 to 3 leaf stage) that had been raised in advance were used as one strain, and the two strains were transplanted and grown in a greenhouse. One day after the transplantation of paddy rice and before the emergence of weeds, a predetermined amount of the test compound was treated under flooding with the granules prepared according to the method described in Formulation Example 5 above. After 30 days from the treatment, the occurrence of weeds and the chemical damage to paddy rice were investigated. The results are shown in Table-2.

In the table, the degree of phytotoxicity against crops and the herbicidal effect against weeds were expressed according to the following evaluation criteria by comparing the generation or growth state of the crops or weeds with the wind dry weight in the case of no treatment. The test compounds are shown by the compound numbers in Table 1 above (the same applies hereinafter).

Evaluation criteria 0: Survival rate 91 to 100 in terms of air-dry weight ratio to untreated plot
% 1: 〃 71 to 90% 2: 〃 41 to 70% 3: 〃 11 to 40% 4: 〃 6 to 10% 5: 〃 0 to 5% Test Example 2 Paddy field weeding weeding test Earl / 5000 Wagner pots were filled with soil, and seeds of Taenia japonicus, broad-leaved weeds (European grass, Azena, Konagi, etc.), fireflies, Heraomodaka, and Tamagaya periwinkle were sown,
It was flooded. Two paddy rice seedlings (2 to 3 leaf stage) that had been raised in advance were used as one strain, and the two strains were transplanted and grown in a greenhouse. During the weed growth period 12 days after transplanting the paddy rice, a predetermined amount of the test compound was treated under flooding with the granules prepared according to the method described in Formulation Example 4 above. Processing 30
The day after day, we investigated the occurrence of weeds and phytotoxicity to paddy rice. The results are shown in Table-3.

In the table, the degree of phytotoxicity to crops and the growth state of weeds are shown according to the method shown in Test Example 1.

From the results shown in Tables 2 and 3, the compounds of the present invention show a wide range of herbicidal activity in the pre-emergence treatment against various harmful weeds that are a problem in paddy fields, and the herbicidal effect is difficult to be exhibited until now. It is clear that it is an excellent compound which shows herbicidal activity even during the growing season treatment and has almost no phytotoxicity to paddy rice.

In addition, 2 described in the above-mentioned literature, which has a relatively similar chemical structure
Almost no herbicidal effect was observed with -benzoylaminopropionitrile, 2-benzoylaminobutyronitrile and the like, and it is clear that the compounds of the present invention have excellent properties that cannot be predicted from the facts known so far.

Test Example 3 Potato epidemic control test Potato (variety: baron, plant height of about 25 cm) grown in a pot in a greenhouse was prepared with a drug having a predetermined concentration (test compound was made into a wettable powder according to the method of the above Preparation Example 8). Was diluted with water to a predetermined concentration) and sprayed with 50 m for 3 pots using a spray gun (1.0 kg / cm ² ) and air dried. A zoospore suspension was prepared from potato blight that had been previously cultured on potato slices for 7 days. This suspension was spray-inoculated onto the potato plants sprayed with chemicals to give 17 to 1 test plants.
After keeping at 9 ° C. and humidity of 95% or more for 6 days, the degree of formation of lesions was investigated.

The lesion area ratio was observed and evaluated for each leaf to determine the disease degree index, and the disease degree was calculated for each plot by the following formula.

The evaluation criteria are as follows.

Disease severity index 0: Disease area ratio 0% 〃 1: 〃 1-5% 〃 2: 〃 6-25% 〃 3: 〃 26-50% 〃 4: 〃 51% or more n ₀ : Disease severity index 0 Number of leaves n ₁ : 〃 1 〃 n ₂ ： 〃 2 〃 n ₃ ： 〃 3 〃 n ₄ ： 〃 4 〃 N = n ₀ ＋ n ₁ ＋ n ₂ ＋ n ₃ ＋ n _{4 The} results are shown in Table-4.

Test Example 4 Cucumber downy mildew control test Cucumbers grown in pots in a greenhouse (variety: Sagamihanjiro,
A spray gun (1.0 kg / cm ² ) was applied to 2 leaves of true leaf) with a drug having a predetermined concentration (the compound to be tested was made into a wettable powder by the method of Preparation Example 8 and diluted with water to a predetermined concentration). ) Was used to spray 30 m per 3 pots and air dried. The downy mildew fungus was collected from the spotted cucumber leaf spot affected by downy mildew, a spore suspension was prepared with demineralized water, and spray-inoculated. The inoculated pot was directly kept at a temperature of 18 to 20 ° C. and a humidity of 95% or more for 24 hours, then transferred to a greenhouse (room temperature 18 to 27 ° C.), and after 7 days, the degree of formation of lesions was examined.

The evaluation criteria and morbidity display method are the same as those described in Test Example 3.

The results are shown in Table-5.

From the results shown in Table-4 and Table-5, the compounds of the present invention are compared with commercially available fungicides which have been widely used conventionally against plant diseases caused by algae such as potato epidemic, cucumber downy mildew and the like. It is clear that it has a very high control effect. Further, 2-benzoylaminopropionitrile or 2-benzoylaminobutyronitrile or the like described in the above-mentioned literature, which has a relatively similar chemical structure, shows almost no disease control effect, and the compound of the present invention is It is clear that it has excellent properties that cannot be predicted from any knowledge.

〔The invention's effect〕

As is clear from the above description, the acylaminovaleronitrile derivative according to the present invention exhibits an excellent herbicidal effect with a wide suitable period which is not expected as a herbicide for paddy fields and which is conventional. Further, as a fungicide for agricultural and horticultural use, it has an excellent control effect against various diseases caused by algae fungi of various crops including soil diseases at a low dose and a low concentration that cannot be expected to be achieved by conventional commercial drugs. The pesticide containing the acylaminovaleronitrile derivative according to the present invention is useful as a herbicide and a fungicide for agricultural and horticultural use because of its excellent properties.

Continuation of front page (51) Int.Cl. ⁵ Identification code Office reference number FI Technical indication location C07C 253/30 C07D 213/81 213/82 307/68 317/60 333/38 (72) Inventor Shunichi Inami Kanagawa 2070 Iijima-cho, Totsuka-ku, Yokohama-shi, Japan (72) Inventor Shoken Hojo 2882 Iijima-cho, Totsuka-ku, Yokohama-shi, Kanagawa (72) Inventor ▲ Sakaki ▼ Masahiro Hara 4-5-45, Kamakura-shi, Kanagawa Examiner Kazuko Nishikawa

Claims (4)

[Claims] 1. A general formula (I) (In the formula, A represents a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, a furyl group, a substituted furyl group, a thienyl group, a substituted thienyl group or a naphthyl group). 2. In the general formula (I), A is a halogen atom,
A lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a methylenedioxy group, a phenyl group substituted with one or more of a nitro group or a cyano group, or a pyridyl group which may be substituted with a halogen atom or a lower alkyl group. The acylaminovaleronitrile derivative according to claim 1, which is a furyl group or a thienyl group. 3. General formula (II) A-COCl (II) (wherein A is a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, a furyl group, a substituted furyl group, a thienyl group, a substituted thienyl group or A naphthyl group) and the formula (III) General formula (I) characterized by reacting with α-aminovaleronitrile represented by (In the formula, A has the above meaning) A method for producing an acylaminovaleronitrile derivative. 4. The general formula (I) (Wherein A represents a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group, a furyl group, a substituted furyl group, a thienyl group, a substituted thienyl group or a naphthyl group) is effective. A herbicide for paddy fields and a fungicide for agricultural and horticultural use, which is contained as an ingredient.