JPS63135364A - Amide-substituted acetonitrile derivative, production thereof and agricultural and horticultural germicide - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [A is a group expressed by formula III (R1 is H, lower alkyl, halogen, etc.; n is 0-4); B is a group expressed by formula VI (R4 is H, lower alkyl, methoxy, etc.; p is 0-5); Y and W are H or lower alkyl]. EXAMPLE:alpha-(Nicotinylamino)-(3-fluorophenyl)acetonitrile. USE:An agricultural and horticultural germicide having both preventive and blight treating effects, capable of exhibiting remarkable effects on blights of algal fungi represented by downy mildew of cucumber with extremely low phytotoxicity. PREPARATION:An aldehyde derivative expressed by formula II is subjected to the Strecker reaction in the presence of an amine expressed by the formula Y-NH2 and an alkali cyanide, e.g. sodium cyanide, etc., to provide a compound expressed by formula IV, which is then reacted with an acid chloride expressed by formula V to afford the aimed compound expressed by formula I.

Description

[Detailed Description of the Invention] [Industrial Application Field] One of the important problems in agricultural production, particularly in the cultivation of fruit trees and vegetables, is plant diseases that depend on the country of origin. Diseases caused by these bacteria are difficult to control due to the physiological and ecological special characteristics of the bacteria, and the development of excellent control agents is desired. Many crops are affected by downy mildew and late blight, and the damage caused is extremely large.

The compound of the present invention is a new compound, but it is effective against mildew,
The present invention was completed based on the discovery that it is highly effective against epidemics.

[Problems to be solved by conventional techniques and inventions] At present, diseases caused by plant pathogenic bacteria are
Cabtan, captafor, dithiocarbamate fungicides, and chlorothalonil are widely used.

However, these fungicides mainly have a preventive effect and can hardly be expected to have a curative effect, so they have the major drawback that they cannot be expected to be fully effective if used only when a disease outbreak is observed. have.

Recently developed and put into practical use, acylalanine compound fungicides, such as metalaxyl, are
Although it has both the effect of curing disease, resistant bacteria have already become a problem, and its effectiveness as a control has begun to be questioned.

Conventionally, regarding amide-substituted acetonitrile derivatives, JP-A-57-167978 and JP-A-57-1769 have been published.
No. 38, JP-A-58-69866, JP-A-Sho 6
0-25579, JP 60-139672, JP 60-169405, JP 60-1
No. 69454, Japanese Patent Application Laid-Open No. 174754/1986,
Although reported in Japanese Patent Application Laid-Open No. 61-44857, the current situation is that these techniques do not necessarily provide sufficient effects on the above-mentioned problems.

[Problem that the invention seeks to solve]

An object of the present invention is to provide a fungicide that has preventive, penetrating, and curative activity against diseases caused by plant pathogenic bacteria that belong to the same category, and does not cause chemical damage to crops.

[Means and actions for solving the problem] As a result of intensive research on amide-substituted acetonitrile derivatives in order to solve the above problem, the following compound group of general formula (1) has been found to be effective against late blight, downy mildew, etc. of various plants. The present inventors have completed the present invention by discovering that they have both preventive and curative effects and exhibit extremely low phytotoxicity to crops. That is, (3) general formula CI]: W A-CONC-CN (1) R2Rz R2R2 (R,).

(Rl　)n (RI), (RI),.

(R+),.

R,R.

R2R2 Rz RzRz
RzRz
l(R1),.

R2 shows.

R1 and R1 represent a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a phenyl group optionally substituted with a halogen atom, an alkoxy group, a cyano group, a methylthio group, or a nitro group.

m and n each independently represent a number selected from integers from 0 to 4.

However, when a plurality of R1 and R3 exist, they may be the same or different.

R2 represents a hydrogen atom, a lower alkyl group, a phenyl group optionally substituted with a halogen atom, or a pyridyl group optionally substituted with a halogen atom.

M represents an oxygen atom or a sulfur atom.

B is shows.

R4 and R1 represent a hydrogen atom, a lower alkyl group, a halogenated alkyl group, a methoxy group, a trialkylsilyl group, or a triphenylsilyl group.

p and q represent integers selected from 0 to 5.

However, when a plurality of R4 and R9 exist, they may be the same or different.

Y and W represent a hydrogen atom or a lower alkyl group. The amide-substituted acetonitrile derivative represented by is a new compound. The present invention further provides a method for producing the amide-substituted acetonitrile derivative represented by the general formula (1). That is, general formula (n): B-C=O(n)(
B indicates the above meaning);
A Strecker reaction is carried out in the presence of an amine of general formula YNHt (In) and an alkali cyanide to obtain an aminonitrile derivative represented by (B represents the above meaning), which is converted into a general formula (V): A-COCl (V) Provides a production method characterized by reacting with an acid chloride represented by (A represents the above meaning).

The production method of the present invention is shown in a reaction scheme and explained below.

Cover (n) (TV) ACON
CCN CI) First, the first step, the Strecker reaction, involves the starting materials of an aldehyde derivative, an alkylamine, aqueous ammonia or ammonium chloride, and sodium cyanide.

Combining alkali cyanide such as potassium cyanide with ethers such as ethyl ether and tetrahydrofuran, benzene,
The reaction is carried out in a binary solvent system of aromatic hydrocarbons such as toluene and water. Reaction temperature is usually 0-100℃
Preferably nearby.

Next, in the second step, the aminoacetonitrile derivative (■) obtained in the first step is reacted with an acid chloride represented by the general formula (V) in the presence of an acid acceptor.

Examples of acid acceptors include organic bases such as triethylamine, dimethylaniline, and pyridine, ammonia, potassium carbonate, and sodium carbonate.

Examples include inorganic bases such as ammonium hydrogen carbonate, sodium hydroxide, and ammonium carbonate.

This reaction is preferably carried out in the presence of a solvent, such as ethers such as diethyl ether, tetrahydrofuran, diisopropyl ether, methyl acetate,
Esters such as ethyl acetate, halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, etc. can be used.

Since the reaction is an exothermic reaction, the reaction temperature is preferably carried out under cooling, preferably from around -30°C to around 50°C, and practically preferably around -20 to 30°C.

The amide-substituted acetonitrile derivative thus obtained is
A pure product can be obtained by conventional purification methods such as recrystallization and column chromatography.

Next, the method for producing the compound of the present invention will be explained using specific examples, but the present invention is not limited to these.

On a large scale (synthesis of compound 7) Ammonium chloride (NH, tl) l O, 7g
(200mmoJ), potassium cyanide (KCN) 6
．． 8 g (104 mmol), 12.1 g of m-fluorobenzaldehyde dissolved in 75 g of toluene at 0° C. with stirring in a mixture of 80 ml of 28% aqueous ammonia
(97.5 mmol) was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was further stirred at room temperature overnight. After the reaction was completed, the toluene layer was separated, and the aqueous layer was extracted twice with toluene. Combine the toluene layers and add saturated sodium bicarbonate solution, followed by 11
After washing with □0 and drying, the solvent was distilled off under reduced pressure to obtain 12.0 g of α-(3-fluorophenyl)ami'noacetonitrile as an orange oil (yield: 82.0 %). The obtained α-(3-fluorophenyl)aminoacetonitrile was used in the next reaction without further purification.

Next, 1.5 g (10.0 mmol) of α-(3-fluorophenyl)aminoacetonitrile and 2.1 g (20.8 mmoJ) of triethylamine were dissolved in 15 mf of acetonitrile, and 1.5 g (10.0 mmol) of α-(3-fluorophenyl)aminoacetonitrile and 2.1 g (20.8 mmoJ) of triethylamine were dissolved in 15 mf of acetonitrile, and 1.5 g (1.5 g) of nicotinic acid chloride hydrochloride was added at 0°C with stirring. 75 g (9.8 mmol) were added.

The reaction mixture was stirred for an additional 30 minutes under water cooling, and then continued to stir at room temperature overnight. After the reaction was completed, 100 ml of water was added, and the mixture was extracted three times with chloroform. The chloroform layer was washed with a saturated NaHCO3 aqueous solution and then dried, and the solvent was distilled off under reduced pressure to obtain the desired α-cotinylamino)-(3-fluorophenyl)acetonitrile as a flesh-colored solid.
98 g was obtained.

(Yield 77.7%). This product was further recrystallized from ethyl ether-n-propanol to obtain m, p,
It became white needle-like crystals with a temperature of 120-121°C.

The compounds of the present invention synthesized in the same manner are shown in Table 1 below.

[Margin below]

Table l YW A-CON CCN Compound A B
YW Melting point 16 A-2-2HB-
2-12,4-CIRHH181-18217
A-2-2HB-2-12-C11, HHgJ, 5-4
2.518 A-2-2HB-2-13-CII
+ HH131,5S-13419A-2-28B
-2-14-Of, HH154~1572OA-
2-2HB-2-12-CI+, OHH138-138
, 5218-2-28B-2-13-C1l, 0HH1
05-10622A-2-28B-2-14-C1hO
HH135, C~136.523 A-2-28
B-2-12-CF, HH153-154.52
4 A-2-2HB-2-13-CFs H
H135=13625 A-2-2HB-2-1
4-G', HH13B-13926A-2-2H
B-1-I HHH134-13527
A-2-2HB-3-I HHH17B, Sea 1
79.528 A-2-2HB-3-2HHH1
50-15129A-2-2HB-2-14-NO,H
H2OA-3-I HB-2-I HH
H74~7831 ^-4-I HB-2-
I HHI (Beauty example 32 A-2-25-B
r B-2-I HHHI87-1883
3 A-2-22-Original 12 B-2-I
HHH164~lω34 ^-2-3 HB-2
-I HHH liquid 35 A-2-22-C4B-
2-I HHH147-149 Compound A
B YW
Melting point compound A B
YW Melting point 56 A-11-28B
-2-I HHH57A-11-34-CN
B-2-I HHH Glassui Genmu 58
A-12-I HB-2-I HH
H59A-12-2HB-2-I HHH60A
-13-I HB-2-I HHH1 illusion~
12561 A-13-22,5-(CIlJz
B-2-I HHH167-16862
A-13-32,5-(01,), B-2-I
HHH13! )-14163A-13-33-
013B-2-I HHH118,! y=119
．． 564 A-13-35-C4B-2-I
HHH123~13165 A-13~4
HB-2-I HHH147-14866
A-14-I HB-2-I H
HH157-15867 A-14-2HB-2
-I HHH 6th Roux 15-IHB-2-IHH
H113-11569A-15-2HB-2-I
HHH152,5-154,570^-16-I
HB-2-I HHH71A-17-I
HB-2-I HHH1 field ~185.572
^-17~2 HB-2-I HH
H73A-18-I HB-2-I HH
H74A-19-I HB-2-I HH
H75A-19-2HB-2-I HHH compound A B Y
W Melting point 76 A-20-I H
B-2-I HHH77A・21-1 t-
C, HI B-2-I HHH788-2
2-2t-C, HeB-2-IHHH79A-Two I
HB-2-I HHH80A-5-I
HB-2-I HHH151-15281
A-Add-I HB-2-I HHH
155-15682 A-27-I HB
-2-I HHH838-15-38B-2~I
HHH liquid 84 A-28-I HB-2
-I HHH85A-2-2'HB-4-I
HHH86^-2-2 8 B-4-
28HH Above, A-1-1 to A-28-1 in Table 1,
8-1-1 to B-4-2 are represented by the following structural formulas (R, , R, and n have the above meanings) CM.

A-9-I A-9-2A-10-I
A-10-3A-10-4A -10-5-1-■--
-1-■■--eyelids---1--■--■■-Lee----
A-10-6A-11-L A-11-2
A-11-3 A-13-I A-13-2A-13-3A
45-I A-15-2A-15
-3A-16-I A-17-I A-17-2A-I
B-I A-19-LA -19-
2A -20-1 A-2LI A-21-2A-
22-I A -22-2A-
24-I A-25-IA-26
-I A-27-1A-28-I
B -1-I B -2-
IB-3-IB-3-2
B-4-I B-4-2 I) I-NMR data of the main compounds listed in Table 1
Shown in the table.

Compound Solvent δ(ppm) Compound Solvent δ(ppm) Compound Solvent δ(ppm) Compound Solvent δ(ppm) Magnetic The present invention further provides compounds represented by the general formula (1) according to the present invention. This is an agricultural and horticultural fungicide characterized by containing 834 amide-substituted acetonitrile compounds as an active ingredient.

The agricultural and horticultural fungicide of the present invention is not only effective against downy mildew and late blight of various crops, but also effective against other diseases. The main diseases are cucumber downy mildew, downy mildew, lettuce downy mildew, Chinese cabbage downy mildew, blight downy mildew of potatoes, late blight of potatoes, late blight of tomatoes, gray blight of cucumbers, late blight of green peppers, and mildew of tomatoes and cowries caused by Pythium blight. These include seedling damping-off of tomatoes and cucumbers caused by rice seedlings, and beet fungus damping-off caused by Aphanomyces bacteria.

Methods for applying the agricultural and horticultural fungicide of the present invention include seed treatment, foliar spraying, soil application, and the like.

When spraying, 10-20001)I)II+ can be applied, preferably 25-11000pp, and further 50-20000pp.
A range of 500 ppm is preferred.

Furthermore, since the agricultural and horticultural fungicide of the present invention has both preventive and curative effects, it has a wide range of suitable periods for preventive spraying, spraying after the onset of disease, and the timing of the spraying. .

The agricultural and horticultural fungicides of the present invention may contain other biologically active compounds, such as similar or complementary fungicides, or agricultural chemicals such as insecticides, herbicides, and plant growth regulators, as well as fertilizing substances, and the above-mentioned improvements. Not only can it be used in combination with other agents, but also mixed preparations with these agents are also possible.

Next, formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient will be shown, but the agricultural and horticultural fungicides of the present invention are not limited to these. In addition, in the following formulation examples, "parts" mean parts by weight.

Jusuke Masuami Wettable powder Compound of the present invention 25 parts Siegrite A 69 parts (Kaolin clay: Sieglite Kogyo ■Product name) Tsurupol 5039
・・・・・・ 3 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■Product name) Carplex (anti-caking agent) ・・・・・・ 3 parts (
White carbon: Shionogi &Co.'s product name) The above is mixed and pulverized uniformly to make a wettable powder. When used, the above-mentioned hydrating agent is diluted 250 to 25,000 times.

Anal dispersion emulsion Compound of the present invention 50 parts Xylene 25
1 part dimethylformamide 20 parts Tsurupol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical brand name) Mix the above evenly. and make an emulsion. When used, the above emulsion is diluted 500 to 50,000 times.

Muko 1 example - Powder Compound of the present invention 10 parts
し - ・・・・・・90
A powder containing 10% of the active ingredient is obtained by uniformly mixing 10% of the active ingredient.

Example 5 Granules Compound of the present invention 5 parts Bentonite 25 parts Tal
After uniformly mixing and pulverizing 70 parts or more, adding a small amount of water, stirring and kneading, granulating with an extrusion granulator, and drying to form granules.

Next, the effects of the compounds of the present invention in biological tests will be specifically described.

On the trial team: Cucumber and disease prevention effect test. 50% of the test compound in emulsion form prepared according to the above formulation example 2 was added to cucumbers (Sumo Hanshiro 1-2 leaf stage) grown in pots with a diameter of 70mm.
Adjust to 0 ppm and add 20 per pot using a spray gun.
Sprayed m1.

The day after spraying, cucumbers and diseased bacteria (Pseudoperono)
sporacubensis spore suspension (X150
15 pieces/field of view) and placed in an inoculation box at a temperature of 25° C. and a humidity of 95% or higher overnight. Afterwards, the leaves were allowed to stand at room temperature, and the ratio of lesions formed 7 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula.

The results of this test are shown in Table 3.

Wiping spot 1 Cucumber and disease treatment effect test diameter 7 crn
Cucumbers grown in pots (Sumo Hanshiro 1-2 leaf stage)
Cucumber and Pseudoper-onosp
ora cubensis) spore suspension (150x.

15 pieces/field of view) and placed in an inoculation box at a temperature of 25° C. and a humidity of 95% or higher overnight for inoculation. The next day, 500p of the test compound in emulsion form prepared according to Formulation Example 2 was added.
Adjust to pm and use a spray gun to spray 20m per port.
I scattered it. Afterwards, the leaves were allowed to stand at room temperature, and the ratio of lesions formed 7 days after inoculation to the inoculated leaves was measured, and the control value was calculated according to the following formula.

The results of this test are shown in Table 4.

Table 4 00ppm Compound Prevention Value Zineb 0 rI Harm Test] Cucumber grown in a pot with an I diameter of 7 cm (Sumo Hanpaku 2
to the third leaf stage), the test compound in the form of an emulsion prepared according to Formulation Example 2 was adjusted to a predetermined concentration and sprayed at 20 ml per pot using a spray gun.

After growing this cucumber in a greenhouse for 7 days, the degree of chemical damage was investigated according to the following criteria.

Margin below Judgment Criteria C] Table 5 1 Q A 332 B 333 C210 D 333 However, the control compounds A to D in the table are the following compounds, respectively.

As is clear from the above biological test results, the compound of the present invention has both preventive and curative effects, is highly effective against fungal diseases such as downy mildew of cucumbers, and is superior to conventional compounds. It is a compound that causes extremely little drug damage as seen in A-D.

Claims (3)

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R_1 and R_3 are a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a phenyl group optionally substituted with a halogen atom, an alkoxy group, a cyano group,
Indicates a methylthio group or a nitro group. m and n each independently represent a number selected from integers of 0 to 4. However, if a plurality of R_1 and R_3 exist, they may be the same or different. R_2 represents a hydrogen atom, a lower alkyl group, a phenyl group optionally substituted with a halogen atom, or a pyridyl group optionally substituted with a halogen atom. M represents an oxygen atom or a sulfur atom. B is ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc. Indicates ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. R_4 and R_5 represent a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a methoxy group, a trialkylsilyl group, or a triphenylsilyl group. p and q represent integers selected from 0 to 5. However, if a plurality of R_4 and R_5 exist, they may be the same or different. Y and W represent a hydrogen atom or a lower alkyl group. ] Amide-substituted acetonitrile derivative. (2) General formula [II]: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] [In the formula, B is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ Mathematical formulas, There are chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Indicates. R_4 and R_5 represent a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a methoxy group, a trialkylsilyl group, or a triphenylsilyl group. p and q represent integers selected from 0 to 5, R_4 and R_5
If there are multiple , they may be the same or different. W represents a hydrogen atom or a lower alkyl group. ] Aldehyde derivatives represented by the general formula [III]: Y-NH_2 [II
I] [Y represents a hydrogen atom or a lower alkyl group. ] The Strecker reaction is carried out in the presence of an amine represented by amine and an alkali cyanide, and the general formula [IV]: ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ [IV] [In the formula, B, W, and Y are the same as above. Indicates the meaning of ] After obtaining the aminonitrile derivative represented by the formula [V
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R_1 and R_3 are a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a phenyl group optionally substituted with a halogen atom, an alkoxy group, a cyano group,
Indicates a methylthio group or a nitro group. m and n each independently represent a number selected from integers of 0 to 4. However, if a plurality of R_1 and R_3 exist, they may be the same or different. R_2 represents a hydrogen atom, a lower alkyl group, a phenyl group optionally substituted with a halogen atom, or a pyridyl group optionally substituted with a halogen atom. M represents an oxygen atom or a sulfur atom. ] General formula [I] characterized by reacting with an acid chloride represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] express meaning. ]
A method for producing an amide-substituted acetonitrile derivative represented by (3) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] [A in the formula is ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼▲Mathematical formulas, There are chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ Mathematical formulas, There are chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, tables, etc. ▼▲ There are mathematical formulas, chemical formulas, 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R_1 and R_3 are a hydrogen atom, a lower alkyl group, a halogen atom, a halogenated alkyl group, a phenyl group optionally substituted with a halogen atom, an alkoxy group, a cyano group,
Indicates a methylthio group or a nitro group. m and n each independently represent a number selected from integers of 0 to 4. However, if a plurality of R_1 and R_3 exist, they may be the same or different. R_2 represents a hydrogen atom, a lower alkyl group, a phenyl group optionally substituted with a halogen atom, or a pyridyl group optionally substituted with a halogen atom. M represents an oxygen atom or a sulfur atom. B is ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc.▼▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc. Indicates ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. R_4 and R_5 represent a hydrogen atom, a lower alkyl group, a halogenated alkyl group, a methoxy group, a trialkylsilyl group, or a triphenylsilyl group. p and q represent integers selected from 0 to 5. However, if a plurality of R_4 and R_5 exist, they may be the same or different. Y and W represent a hydrogen atom or a lower alkyl group. ] An agricultural and horticultural fungicide containing an amide-substituted acetonitrile derivative represented by the following as an active ingredient.