JPH01121263A - Amide-substituted derivative and antigermicide for agriculture and horticulture - Google Patents

Abstract

NEW MATERIAL:An amide substituted derivative expressed by formula I [A is formula II, formula III, formula IV, formula V, formula VI, etc.; D is cyano; thiocarbamoyl or acylthiocarbamoyl each expressed by the formula -CN, -CSNH2 or -CSNHCOR7; R1 and R2 are H, 1-4C alkyl or halogen; R3 is H, 1-4C (halogenated)alkylphenyl, tolyl, pyridyl, etc.; R4, R5 and R6 are H, 1-4C (halogenated)alkyl, halogen, 1-4C alkoxy, cyano, etc.; R7 is 1-4C alkyl, cylohexyl or phenyl]. EXAMPLE:N-(1-Cyano-2-butenyl)-pyridine-3-carboxyamide. USE:Useful as a germicide for agriculture and horticulture having preventing and treating effect to epidemic of various kind of plants, downy mildew, etc. as well as having no phylotoxicity to crops. PREPARATION:For example, an aldehyde expressed by formula VII used as a raw material is reacted with an alkali cyanide and the resultant product is reacted with an acid halide to provide the compound expressed by formula I.

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a novel amide-substituted derivative and an agricultural and horticultural fungicide containing the derivative as an active ingredient. [Prior art and problems] One of the important problems in agricultural production, especially in the cultivation of fruit trees and cane vegetables, is the problem of diseases caused by plant pathogenic bacteria belonging to the fungi class (e.g., downy mildew, late blight, etc.). be. 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. Currently, cabtan (common name), captafor (common name),
Dithiocarbamate fungicides such as zineb (generic name) and chlorothalonil (generic name) 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 if they are used only when a disease outbreak is observed, sufficient effects cannot be expected. There is. Antibacterial agents containing acylalanine compounds that have been recently developed and put into practical use, such as metalaxyl (generic name), have both preventive and curative effects, but resistant bacteria have already emerged. However, its control effect has been considerably reduced. Conventionally, amide-substituted acetonitrile derivatives, amide-substituted thioacetamide derivatives, and amide-substituted N-acylthioacetamide derivatives that are chemically similar to the compounds of the present invention have been reported in JP-A-60-103056, etc.; The prior art cannot be said to be sufficient as a practical fungicide for agricultural and horticultural purposes, and the chemical may cause chemical damage to useful crops, which remains a major unresolved problem. [Problems to be Solved by the Invention] The present invention has a preventive effect and a curative effect against diseases caused by plant pathogenic bacteria belonging to the fungi class (e.g., downy mildew, late blight, etc.) and is useful. The aim is to provide a fungicide that does not harm crops. [Means and effects for solving the problem] As a result of intensive research on the above-mentioned amide derivatives to solve the above-mentioned problem, the group of compounds of the general formula [1] shown below have been found to be effective against late blight and downy mildew on various plants. The present invention has been completed based on the discovery that it has both preventive and curative effects on plants, and has extremely low phytotoxicity to crops. The compound of the present invention is a new compound that has not been described in any literature. That is, the present invention provides a novel amide-substituted derivative represented by the general formula [1]: and an agricultural and horticultural fungicide containing the derivative as an active ingredient. (Hereafter, margin)

[In the above formula, A is R3R3 R3R11R3 + 1 lR3R3R3 p. Is RI R3 D -CN, -C5NH2 or -C5NHCOR?
represents a cyano group, thiocarbamoyl group or acylthiocarbamoyl group. Here, R8 and R2 each independently represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a halogen atom. Here, R1 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a phenyl group optionally substituted with a halogen atom, tolyl group, pyridyl group, or pyrimidyl group. represent. R4, R3, and R each independently represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a halogen atom, or a halogen atom having 1 to 4 carbon atoms.
4 represents a halogenated alkyl group, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a lower alkylthio group having 1 to 4 carbon atoms. R7 represents a lower alkyl group having 1 to 4 carbon atoms, a cyclohexyl group, or a phenyl group. ] Next, a method for producing the compound of the present invention will be shown in a reaction scheme and explained below. Reaction soil 2k [Production method 1] ■ R1-C=Cl-R2R+-C=C)l-Rz (5)
(7)

[In the formula, A, R+
, R2 and R9 have the above meanings, and X represents a halogen atom. [Production method 1] The intermediate aminoacetonitrile derivative [3] in the first step is synthesized by two methods. Method a-1 is a method for obtaining by Strecker reaction. The starting material aldehyde [2], ammonia water and/or ammonium chloride, and an alkali cyanide such as sodium cyanide or potassium cyanide are combined with ethers such as ethyl ether or tetrahydrofuran, or aromatic hydrocarbons such as benzene or toluene, and water. The reaction is carried out in a binary solvent system. The reaction temperature is usually preferably around 0 to 100'C. In method a-2, the starting material aldehyde [2] and a trialkylsilylnitrile represented by trimethylsilylnitrile are reacted in the presence of a catalytic amount of a Lewis acid such as zinc iodide as necessary to form an intermediate [10]. obtain. Subsequently, the aminoacetonitrile derivative [3] is obtained by reacting with ammonia dissolved in a solvent such as methanol or ethanol. Next, in the second step, the aminoacetonitrile derivative [3] obtained in the first step is reacted with the acid halide represented by the general formula [4] in the presence of an acid acceptor. Examples of acid acceptors include organic bases such as triethylamine, dimethylaniline, and pyridine, and inorganic bases such as ammonia, potassium carbonate, sodium carbonate, ammonium bicarbonate, sodium hydroxide, and ammonium carbonate. . Further, this reaction is preferably carried out in the presence of a solvent, such as esters represented by diethyl ether, tetrahydrofuranthyl esters, methyl acetate, ethyl acetate, methylene chloride, chloroform, 1,2-dichloroethane, etc. Representative halogenated hydrocarbons, acetonitrile, and the like can be used. Since the reaction is an exothermic reaction, the reaction temperature is preferably carried out under cooling, and is preferably from around -30°C to around 50°C.
Practically speaking, a temperature around -20 to 30°C is desirable. In this way, the desired amide-substituted acetonitrile derivative is obtained. [Production method 2] A method in which the starting material carboxylic acid derivative [6] and the aminoacetonitrile derivative [3] obtained in [Production method 1] are dehydrated and condensed in the presence of a dehydrating agent to obtain the desired amide-substituted acetonitrile derivative. be. As a dehydrating agent, dicyclohexylcarbodiimide (D
Particularly preferred are carbodiimides such as CC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, and inorganic dehydrating agents such as silicon tetrachloride. [Production method 3] The desired product can be obtained by reacting the amide-substituted acetonitrile derivative [5] obtained in [Production method 1] or [Production method 2] with hydrogen sulfide in the presence of a tertiary amine such as triethylamine or pyridine. A thioamide derivative [7] is obtained. [Production method 4] The objective is achieved by reacting the thioamide derivative [7] obtained in [Production method 3] with the acid halide derivative [8], optionally in the presence of an effective amount of a tertiary amine such as triethylamine or pyridine. Acylthioamide derivatives

[9]
is obtained. Examples of acid halide derivatives include lower alkylcarboxylic acid halides such as acetyl chloride and propionyl chloride, and cyclic acid halides such as cyclohexylcarbonyl chloride and benzoyl chloride. The amide derivative thus obtained can be made into a pure product 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. Synthesis of 0-N-(1-cyano-2-butenyl)-pyridine-3-carboxamide (compound No. 2) Add 10.0 g of ammonium chloride and 8.0 g of potassium cyanide to 50 g of water.
mA, and in this aqueous solution 25 m of diethyl ether,
Add 28% Lord ammonia water and stir. To this was added dropwise 7.0 g of crotonaldehyde while cooling with water, and the mixture was further stirred at the same temperature for 9 hours, after which the ether layer was separated. The aqueous layer is extracted twice with diethyl ether Loom, then 50 g of common salt is added and extracted once again with LooIRl diethyl ether. The ether layers were combined, dehydrated and dried in order of saturated brine, then anhydrous sodium sulfate, and the ether layer was distilled off under reduced pressure to obtain a yellowish solid. Dissolve this oil in 100 d of tetrahydrofuran, add 10.2 g of triethylamine under water cooling, and further add 5.4 g of nicotinic acid chloride hydrochloride. After continued stirring for 4 hours under water cooling, the precipitated triethylamine hydrochloride was filtered off, and the filtrate was concentrated under reduced pressure to obtain a reddish color. This oil is purified by silica gel column chromatography eluting with chloroform and then ethyl acetate to give an orange color. This oil is triturated with isopropyl ether, and the precipitated crystals are converted into isopropyl ether:
By washing with diethyl ether 3:5, N-(
1.8 g (yield: 29.5%) of flesh-colored crystals of 1-cyano-2-butenyl)-pyridine-3-carboxamide are obtained. m, p, 10B-109°C'N-NMR (CDCj2a, TMS): δ
Cppm)=1. T2 (d, 3H, J=6Hz),
5.19-6.40 (m, 3H), 7.30 (dd
, 18. J = 7.8Hz, 5.4Hz). 7.92-8.29 (m, IH), 8.32 (d,
II, J=7.81(z). 8.35-8.73 (n+, IH), 8.74-9
．． 04 (m, IH). Synthesis of N-(1-cyano-2-butenyl)-1-methylpyrazole-4-carboxamide (compound No. 39) containing real JidL 10.0 g of ammonium chloride was dissolved in 50 g of water, and 8 g of potassium cyanide was added to this aqueous solution. ．． Add Og and stir. After adding 20 parts of diethyl ether and 10 parts of 28% aqueous ammonia, crotonaldehyde 7.
0g was added dropwise. After stirring at the same temperature for 10 hours, the ether layer was separated, and the aqueous layer was extracted three times with diethyl ether. The ether layers are combined and dried by dehydration in the order of saturated brine and then anhydrous sodium sulfate, and the ether is distilled off under reduced pressure at 20° C. to obtain a yellow-brown ofl. This oil was dissolved in tetrahydrofuran Loo II 11, and 5.0 g of triethylamine was added under water cooling, and then 4.3 g of 1-methylpyrazole-4-carbonyl chloride was added under stirring at the same temperature, and stirring was continued for 3 hours under water cooling. After the reaction, the precipitated triethylamine hydrochloride '22 was filtered off and the filtrate was concentrated under reduced pressure to give a reddish-brown oil1.
I get it. This oil was purified by silica gel column chromatography eluting with chloroform and then ethyl acetate to yield 2.1 g of a skin-colored solid of N-(1-cyano-2-butenyl)-1-methylpyrazole-4-carboxamide (yield 34 .2%) was obtained. m, p, 137-140″C′HNMR (CDCj!i, TMS): δ(p
pm)=1.75 (d, 3H, J=6Hz), 3.
84 (s, 3H). 5.17-6.33 (m, 3H), 7.84 (s, L
H), 7.91 (s, IH), 8.42 (d, 1■
, J=7.8Hz). Synthesis of N-(1-cyano-2-butenyl)-1,3-dimethylpyrazole-5-carboxamide (Compound No. 59) Ammonium chloride I O,Og was dissolved in 50 d of water, and in this aqueous solution Add 8.0 g of potassium cyanide and stir. Add 15mj of diethyl ether to this! After adding 10 ml of 28% aqueous ammonia, 7.0 g of crotonaldehyde was added dropwise with stirring while cooling with water. After continuing stirring at the same temperature for 10 hours, the ether layer was separated, and the aqueous layer was extracted three times with diethyl ether. The ether layers were combined, dehydrated and dried using saturated brine, then sodium sulfate, and the ether was distilled off under reduced pressure to obtain a yellowish color. This oil was dissolved in 100 d of tetrahydrofuran, and 5.1 g of triethylamine was added under water cooling. Next, 1,3-dimethyl and 4.7 g of lab-ru-5-carbonyl chloride were added while stirring at the same temperature, and stirring was continued for an additional 4 hours. After the reaction is complete, the precipitated triethylamine hydrochloride is filtered off, and the filtrate is concentrated under reduced pressure to obtain a reddish color. This oil was subjected to silica gel column chromatography eluting with chloroform and then ethyl acetate, followed by thin layer chromatography (Merck Art, 5717, CH
By purifying with Cl23: Ac0Et 10:1), N-(1-cyano-2-butenyl)-1
, 12.63 g (yield: 40.2%) of orange-red oil of 3-dimethylpyrazole-5-carboxamide was obtained. 'H-N million R (CDCl2., TMS): δ(
ppm)=1.74 (d, 3H, J=6Hz), 2
．． 16 (s, 3H). 4.00 (s, 3H), 5.13-6.23 (m,
3H), 6.30 (s, 1■), 7.01 (d,
(LH, J=8.0Hz) Table 1 shows the compounds of the present invention that can be synthesized in the same manner. (Hereafter, blank space) Table 1 No. A R3R4R5RI R2
DNo, A R3R4R5RI
R2D66 A6 CH3CH3I
CHI5 HCN67 A6 C
H3CH3CH3HII CN68 A6
CI3 C1b CH3HCH3CN
69 86 CH3CHs C
H3CH3HCN7〇 86 CH3
CH3C11l l (C2H5CN73
A6 CI3 C1■ HCO
, CN74 A6 CH3' CI
HHCH3C3NH2No, A R
s Ra Rs RI To
D102 86 CxH
6CI HCHs CH3CN103
86 CJs CI
HHCJs CN104 A6 C
Js CI HCJs HCN105
A6 CzHs CN HHC
H3CN106 A6 CJs CF
3 HHCH3CN107 ^6 Cz)
Is Ch HCH3HCN108 A
6 CJs CF+ HCH3CFI3C
N109 A6 CzllsCJs
HHC1 (3CN110 A6 CJsCz
Hs HCH3HCN111 A6 C
H2F Hl(Hl(CN112 A6
C) lzF HHHCH, 1CN113
A6 CHJ HHCHs HCN11
4 ^6 CH2F HH■ C2
1 (S CN115 A6 CH2F
HHCH3CL CN116 A6
cn2FHHCI, H8HCN117 86 CHFz HHHHCN118
A6 CHF2 HHHCH3CN11
9 A6 CHF2 HHCTo
)I CN120 ^6 CHF2H
H)l C2H5CN121 A6 C
HF2 II ) I CH3GHz
CN122 A6 CHF2 H
HCJS ■ CN137 86
CHh CI HHCHs
CNN No. A Rs R4
R5RI R2D138 A6 C
HF2 CI HCHs HCN139
A6 CHz CH3Hll
CI CN140 A6 CH3
CHs HCH3CI CN141
A6 CH3CI HHCI C
N142 A6 CH3CI HC
HI CI CN143 A6
CH3CH3)I HCI C3N
Hz144 A6 CF3 CI
HHCH3CN145 A6CH2CF3
CH3Hl(CH:+CN146 A6
CToCHzCICHs Hl(CH3CN
147 ^6 NI C) 13 H
HCH,1CN148 A6 N2CHi
HHCH3CN149 A6 N
5CTo HHCH3CN150 A6
N4CHs HHCH3CN151
A6 N5CH3HHCHs CN15
2 86 N6CHs HH
CH3CN153 86 N7CH2
HHCH, 3CN154 A6 N8CH
i HHCH3CN155 86
N9CHs HHCH:l CN
156 A7 HHHHHCN157
A7 HHHCH3HCN158 A
7 HHHHCH3CN159 87
HHHC2H5HCN160 87HHHCH3CH3CN161 A7
HHHHCHI5 CN162 A7
CHs l(H11HCN163 A7
CL HHCHs HCN164
87 CH3■ HHCL
CN165 A7 CL HHCH
I5 HCN166 87 CH
3HHCHHz CHa CN167
A7 C)13 HHHC2H5CN
168 A7 CJs HHHHCN1
69 ^7 C2F15 II
■c■s HCN17〇87
CJs HHHCH3CN171
A7 C1Hs HHCJs HC
N172 A7 CxH8HHCHI
C)+3 CN173 ^7 CJ
s HHEI C2H5CNNo,
8 lh R4R5RI
Ih DNo, A R
,R4R,R,DNo, A R4R5
RI R2DNo, A R4
R5R, R, D However, A1 to A 29 in Table 1 above
and each symbol of N1 to N9 is represented by the following structural formula. (R1-R1 has the same meaning as above.)AI
A2 A3 A4 A
5 A6A7 A8
A9AIOAll A121? . Al 3 Al 4 A
l 5I R3R3 Al 6 Al 7 Al
BA19 A20 A21A
22 A23 A24A25
A26 A27A28
A29 N4 N5 N6N
7 N8 N9 (hereinafter referred to as blank space) The present invention further provides an agricultural and horticultural fungicide characterized by containing the amide-substituted derivative represented by the general formula (1) according to the present invention as an active ingredient. It is. 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 include cucumber downy mildew, grape downy mildew, lettuce downy mildew, Chinese cabbage downy mildew, hop downy mildew, potato late blight, tomato late blight, cucumber gray late blight, green pepper late blight, tomatoes caused by Pythium blight,
These include seedling damping-off of cucumbers and rice, and seedling damping-off of beets caused by the fungus Afbunomyces. Application methods for the agricultural and horticultural fungicide of the present invention include seed treatment, foliage spraying, soil application, and the like. The amount and concentration of application will vary depending on the target crop, target disease, degree of disease occurrence, application method, etc., but when spraying, the amount of active ingredient should be 2 to 2 per hectare.
Applicable at 2000g, preferably 10-1000g. It can be applied at a spraying concentration of 1 to 11,000 pp.
5 to 500 ppm is desirable. In addition, since the agricultural and horticultural fungicide of the present invention has both preventive and curative effects, it can be applied both preventively and after the onset of disease, and there is a wide range of suitable times for its application. have. The agricultural and horticultural fungicides of the present invention may optionally contain other biologically active compounds, such as similar or complementary fungicides, or agricultural chemicals such as insecticides, herbicides, plant growth regulators, and fertilizers. Not only can it be used in combination with effective substances, soil conditioners, etc., but also mixed formulations with these are also possible. The agricultural and horticultural fungicide of the present invention can be prepared using a suitable carrier, such as a solid carrier such as clay, talc, bentonand, diatomaceous earth, or water, alcohol M (methanol, ethanol, etc.), aromatic hydrocarbons (benzene, toluene, xylene, etc.). ), chlorinated hydrocarbons, ethers, ketones, esters (
ethyl acetate, etc.). It can be applied by mixing with a liquid carrier such as acid amides (dimethylformamide, etc.), and if desired, an emulsifier, a dispersant, a suspending agent, a penetrating agent, a spreading agent, a stabilizer, etc. are added.
Emulsions, oils, hydrating agents, powders. It can be put to practical use in any dosage form such as granules or flowables. Next, the range of each component and the type of each component in formulation examples of these compositions will be shown, but the agricultural and horticultural fungicide of the present invention is not limited to these. In addition, in the following formulation examples, "parts" mean parts by weight. (1) Wettable powder Compound of the present invention: 5 to 75 parts Solid portion: 9 to 86 parts Surfactant
・・・・・・ Parts 5 to 10 Others
.... Calcium carbonate, kaolinite, ziecrite A, ziecrite PFP as the 1- to 5-hedral carrier. Examples include diatomaceous earth and talc. As surfactants, Lunonx 1ooo c, Tsurupol 5039, Tsurupol 5050, Tsurupol 00
Examples include 50° Trupol 5029-0, calcium sulfonate, and sodium dodecyl sulfonate. Other components include Carplex 1180 and the like. (2) Emulsion Compound of the present invention: 5 to 50 parts Liquid carrier: 35 to 90 parts Surfactant
・・・・・・ 5 to 15 parts As a liquid carrier,
xylene, dimethylformamide, methylnaphthalene,
Examples include isophorone. Examples of the surfactant include Tsurupol 2680, Tsurupol 3005X, and Tsurupol 3346. (3) Flowable agent Compound of the present invention: 5 to 75 parts Liquid carrier: 14.5 to 68 parts Surfactant: 5 to 10 parts Others
... 5 to 10 parts Water is used as the liquid carrier. Examples of the surfactant include Lunox 100OC, Tulpol 3353, Sorbohol PL, Nirapol, Agrisol S-710, sodium ligninsulfonate, and the like. Other ingredients include ethylene glycol, propylene glycol, xanthan gum, and the like. (4) Powder Compound of the present invention: 0.03 to 3-hedral carrier: 94-98.97 parts Others: 1- to 3-hedral carrier: carbonic acid; Calcium, kaolinite, gicrite,
Examples include talc. Other ingredients include diisopropyl phosphate,
Examples include Carplex #80. (5) Granules Compound of the present invention: 0.3 to 10 parts Solid part: 92 to 98.7 parts Others: 1 to 5 parts As a hedral carrier: , calcium carbonate, kaolinite, bentonite, talc, etc. Other ingredients include calcium lignin sulfonate, polyvinyl alcohol, and the like. Next, specific formulation examples of the agricultural and horticultural fungicide containing the amide substituted derivative represented by the general formula (1) according to the present invention as an active ingredient will be shown. ,
It is not limited only to these. In addition, in the following formulation examples, "parts" mean parts by weight. 1 dish per plate Wettable powder Compound of the present invention 25 parts Sieglite PPP 69
(Mixture of kaolinite and sericite: Sieglite Industries ■Product name) Tsurupol 5039 3
1 part (mixture of anionic surfactant and white carbon: Toho Chemical ■trade name) Carplex #80 ... 3 parts (white carbon: Shionogi & Co., Ltd. ■trade name) or more are uniformly mixed and pulverized. Use as a hydrating agent. When using, add the above hydrating agent to 500~
It is diluted 50,000 times and applied so that the amount of active ingredient is 10 to 1000 g per hectare. Anal salmon emulsion Compound of the present invention 50 parts Xylene 25 parts N
, N-dimethylformamide 10
Part Tsurupole 3346 ・・・・・・
15 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical ■ trade name) The above was mixed uniformly to form an emulsion. When used, the emulsion is diluted 1,000 to 100,000 times and applied so that the amount of active ingredient is 10 to 1,000 g per hectare. u■ Powder Compound of the present invention: 10 parts Clay: 90 parts or more are mixed uniformly to obtain a powder. When used, the above-mentioned powder is sprayed as is at an amount of active ingredient of 10 to 1000 g per hectare. Ice ■ Cited Example" Granules Compound of the present invention 5 parts Bentonite 25 parts
・・・・・・ After uniformly mixing and pulverizing 70 parts or more,
Add a small amount of water, stir and mix, granulate using an extrusion granulator, and dry to form granules. When used, the above-mentioned granules are sprayed as is at an amount of active ingredient of 10 to 1000 g per hectare. Next, the effects of the compounds of the present invention in biological tests will be specifically described. m soil Cucumber and disease prevention effect test When cucumbers (variety: Sumo Hanshiro) grown in pots with a diameter of 7 marks reached the 1st to 2nd leaf stage, the test compound in the form of an emulsion prepared according to Formulation Example 2 above was applied. Dilute with water to 500p
Adjust to pm and use a spray gun to add 20mj per pot.
! Spread. The day after spraying, cucumbers and diseased bacteria (Pseudo)
peronospora cubensis) spore suspension (2x 105 spores/ml) was sprayed at 25°C.
1. The seeds were placed in an inoculation box with a humidity of 95% or higher overnight. Thereafter, the plants were placed in a greenhouse, 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 test results are shown in Table 2. Compound No., Control value Zineb 65 The trade name of Zineb in Table 2 is Daisen, and the chemical name is:
Zinc ethylene bisdithiocarbamate. Cucumber and disease bacterium (P
seudoper-onospora cubensi
A spore suspension (2 x 10' spores/ml) of s) was sprayed on the spores, and the spores were placed in an inoculation box at a temperature of 25° C. and a humidity of 95% or higher overnight for inoculation. The next day, the test compound in emulsion form prepared according to Formulation Example 2 was diluted with water to give a concentration of 50 ppm.
Adjust to 20mI per pot using a spray gun! ,
It was scattered. Thereafter, the plants were placed in a greenhouse, 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. (Hereinafter, blank space) Table 3 (Treatment concentration: 500 ppm) Compound No. Control value Zineb O As is clear from the above biological test results, the compound of the present invention has both preventive and curative effects and is effective against cucumber paste. It is a compound that is highly effective against algae and fungal diseases, such as the common fungal disease. Patent applicant Nissan Chemical Industries, Ltd.

Claims (2)

[Claims] (1) General formula [1]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] Amide substituted derivatives represented by. [In the above formula, A is ▲Mathematical formula, chemical formula, table, etc.▼, ▲Mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, Represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, D is -CN, -CSNH_2 or -CSNHCOR
Represents a cyano group, thiocarbamoyl group, or acylthiocarbamoyl group represented by _7. Here, R_1 and R_2 each independently represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a halogen atom. It represents an alkyl group, a halogenated alkyl group having 1 to 4 carbon atoms, a phenyl group optionally substituted with a halogen atom, a tolyl group, a pyridyl group, or a pyrimidyl group. R_4, R_5, and R_6 are each independently a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a halogen atom, a halogenated alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or Represents a lower alkylthio group having 1 to 4 carbon atoms. R_7 represents a lower alkyl group having 1 to 4 carbon atoms, a cyclohexyl group, or a phenyl group. ] (2) General formula [1]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] An agricultural and horticultural fungicide containing one or more of the amide-substituted derivatives represented by the following as an active ingredient. [In the above formula, A is ▲Mathematical formula, chemical formula, table, etc.▼, ▲Mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, Represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, D is -CN, -CSNH_2 or -CSNHCOR
Represents a cyano group, thiocarbamoyl group, or acylthiocarbamoyl group represented by _7. Here, R_1 and R_2 each independently represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a halogen atom. It represents an alkyl group, a halogenated alkyl group having 1 to 4 carbon atoms, a phenyl group optionally substituted with a halogen atom, a tolyl group, a pyridyl group, or a pyrimidyl group. R_4, R_5, and R_6 are each independently a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a halogen atom, a halogenated alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or Represents a lower alkylthio group having 1 to 4 carbon atoms. R_7 represents a lower alkyl group having 1 to 4 carbon atoms, a cyclohexyl group, or a phenyl group. ]