JPS61280466A - Formamide oxime derivative, production thereof and agricultural and horticultural fungicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (X and Y are H, halogen, lower alkyl, lower alkenyl, etc.; R is lower alkyl, lower alkenyl, etc.; R' is lower alkyl, lower alkenyl, lower alkynyl, H, etc.). EXAMPLE:N-( 3-Chloro-4-ethoxy-5-methoxymethylphenyl )-N'-methoxyformamidi ne. USE:Fungicide for agricultural and horticultural use. It exhibits strong fungicidal activity against various resistant pathogens of e.g. powdery mildew, scab, etc., of apple. Furthermore, it is effective for the control of rice blast regardless of the resistance of the pathogen. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II (R'' is lower alkyl) with the compound of formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [I] [wherein X and Y are hydrogen atoms, , cyano group, or general formula -
ARr.

-CH20R2, -C-R2, -COOR2.

-CHcoN-0R4, -NH-C-A'-R1.

-NH-C-R1 or -NHCH=N-ORi (where R1 is a lower alkyl group,
represents a lower alkenyl group, lower alkynyl group or lower haloalkyl group, =Rz and R8 represent a lower alkyl group, R4 represents a hydrogen atom or a lower alkyl group, A
and A' represents an oxygen atom or a sulfur atom, n is 2,
3 or 4), provided that X and Y do not simultaneously represent a hydrogen atom or a halogen atom.

R is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or the general formula -A"-R5゜-C-Ra or -C
H20Rs (wherein, Rs represents a hydrogen atom, a lower alkyl group-lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, or a lower haloalkyl group, and A'' represents an oxygen atom or represents a sulfur atom, and R6 represents a lower alkyl group).

R' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower heteroalkyl group, a lower haloalkenyl group,
A formamide oxime derivative (hereinafter referred to as the compound of the present invention) represented by a lower haloalkynyl group, a lower cya, a noalkyl group, or a hydrogen atom, and a method for producing the same, and a fungicide for intestinal horticulture containing the same as an active ingredient. It is something.

Formamide oxime derivatives represented by the general formula [=I] include benomyl [methyl 1-(butylcarbamoyl)benzimidazole-2-ylbamate], fuberidazole C2-(2-furyl)benzimidazole], thiabendazole C2-(4 -thiazolyl)benzimidazole], carpendazim [methyl benzimidazole-2-ylbamate], thiophanate methyl [
1,2-bis(3-methoxycarbonyl-2-thioureido)benzene], thiophanate [1,2-bis(3
-Ethoxylic and procymidone CN-<3', 5'
-dichlorophenyl)-1,2-dimethylcyclobrono-1,2-dicarboximide], iprodione C
3-(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2,4-dione],
Vinclozolin [3-(3', 5'-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,
4-dione], ethyl (R5”) -3-(3',
For plant pathogenic bacteria and other filamentous fungi (hereinafter referred to as drug-resistant bacteria) that are resistant to cyclic imide fungicides such as 5'-dichlorophenyl)-5-methyl-2,4-dioxoxazolidine-5-carboxylate. On the other hand, it is characterized by showing a selectively strong bactericidal effect.

The inventors of the present invention have conducted extensive studies on bactericidal agents that exhibit a bactericidal effect against drug-resistant bacteria, and as a result, have discovered the compound of the present invention represented by the general formula [■].

Examples of drug-resistant bacteria for which the compound of the present invention exhibits a strong bactericidal effect include powdery mildew of apples (Podosphae
ra 1eucotricha), Sclerosis fungus (Ve
nturia 1naequalis), Venturia nashicola, Scle-rotinia ma
li), oyster anthracnose (Gloeospori-u)
m kaki), peach gray layer disease fungus (Sclerotin)
iacinerea), Cladospo
botrytis cinerea), Botrytis cinerea.

Black rot fungus (Eisinoe ampelina)
, late rot fungus (Glomerella cingulat)
a) , f
pora beticola), beannut brown spot disease value (Cercospora arachidicola)
), Cercospora person
ata), barley powdery mildew fungus (Erysiph
e graminis f-sp-hordei), eye-spot fungus (Cercosporella he
rpotri-choides), Red 3 rot fungus (F
usarium n1vale), wheat powdery mildew (Erysiphe graminis f-sp,
tritici), Kyu IJ (7) 5 and A,
C7M1li (Sphaerotheca fulig)
inea), Mycosphaerell
a melonis), botrytis fungus (Botryt
is cinerea), Cladospo
C1adosp-orium fulvum, Botrytiscinerea, Sphaeroth-eca hu
muli), *-y BotrY-
tis cinerea), powdery mildew of tobacco (
Erysiphecichoracearum), Rose scab fungus (Dipl.

carpon rosae), tangerine scab fungus (
E 1 s inoefawcetii), Penicillium 1talic-um
, Penicillium digita
tum), etc.

As a result of further studies, it was found that the compound of the present invention is effective against the rice blast fungus (Pyricu-1aria), regardless of the presence or absence of drug resistance.
It was found to be effective in controlling insects such as S. oryzae).

Examples of the compounds of the present invention are shown in the qX-table.

Table 1 The compounds of the present invention can be produced, for example, by the method shown in the following reaction formula.

■ [■] [■] engineering [I) [In the formula, X, Y, R and R' are as described above.

R″ represents a lower alkyl group.] ■ In the general formula CI), when R is a substituent represented by the general formula -A″ R's [Iv] [v] In the C formula, X, Y, R' and A'' is as described above. R's represents a lower alkyl group, lower alkenyl group, lower alkynyl group, lower alkoxyl group, or lower haloalkyl group. Z represents a leaving group.] As the above leaving group is, for example, a mesyloxy group, a tosyloxy group, or a halogen atom.

■ In the general formula [I], when the substituent R' is represented by R''' [wherein, X, Y, R and Z are as described above.
″′ is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkenyl group,
Represents a lower haloalkynyl group or lower cyanoalkyl group. ] In other words, in the method shown in reaction formula (III), general formula CII)
The compound represented by the formula [m] is reacted with the compound represented by the general formula [m] in an organic solvent.

Polar solvents such as methanol and ethanol are used as the organic solvent. The reaction is carried out for 0.5 to 1 hour at a temperature range from room temperature to the boiling point of the solvent.

When the reaction is carried out using a compound in which R is -OH or R' is a hydrogen atom in the method, the general formula [rV]
Alternatively, a compound represented by C'VI'l can be produced. The compound represented by the general formula [rV) or [vI] can be prepared using the general formula [rV] or [vI] by the method shown in the reaction formula ■ or ■.
v) Alternatively, the compound of the present invention can be obtained by reacting a compound represented by the general formula [■]. The reaction is usually carried out.

Inert solvents such as dimethylformamide, tetrahydrofuran, acetonitrile, chloroform, and toluene are used as organic solvents, and sodium hydride, triethylamine, pyridine, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate are used as acid binders. Organic or inorganic bases such as the following are used.

The compound represented by the general formula [ID] can be produced, for example, by reacting the corresponding aniline with ethyl orthoformate as shown in the reaction formula below.

The structure of the compound was determined from the results of spectrum analysis such as IR and NMR-MASS.

Compounds represented by the general formula [''] are illustrated in Table 2.

Table 2 Next, the manufacturing method of the present invention will be explained in more detail with reference to manufacturing examples.

Production Example O-methyl hydrochloride and 2.0Of droxyamine were added at 0°C to a methanol solution of sodium methoxide prepared from sodium o, ssy and 5Q'ml of methanol. To this was added 6.491 ml of ethyl N-(3-chloro-4-ethoxy-5-methoxymethylphenyl)formimidate obtained in the reference production example described later.

After stirring at room temperature for 1 hour, the mixture was poured into ice water and extracted with ethyl acetate. After washing the excavated layer with water and drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was
It was purified by column chromatography using basic alumina, toluene and ethyl acetate, and N-(3-chloro-4
-Ethoxy-5-methoxymethylphenyl)-N'-methoxyformamidine 2.891 was obtained.

2B, 0 nDl, 5580 The structure of the compound was determined from the results of spectrum analysis such as IR, NMR, and MASS. Furthermore, the compound of the present invention includes two types of tautomers shown below, each of which includes 8 and 2 geometric isomers. The compounds of the present invention include any isomers.

The compound produced based on such production method 1ζ was mixed with reference production example 3-chloro-4-nitoxy-5-methoxymethylaniline 14.81f, ethyl orthoformate 20.71 and ethyl acetate 160-70 to 80% while stirring and mixing. The mixture was heated to 0.degree. C., and ethanol produced during the reaction was distilled off as an azeotrope with ethyl acetate at normal pressure. When the distillate almost disappeared, the reaction temperature was raised to 100°C, and heating, stirring, and distillation were continued for about 1 hour.

Thereafter, excess ethyl orthoformate was distilled off at 15-20 mHl and 50-60°C to obtain the crude intermediate ethyl N-(3-chloro-4-ethoxy-5-methoxymethylphenyl)formimidate. This was purified by column chromatography using basic alumina and toluene to obtain the target compound 14.2N.

, ga,.

Table 4 shows compounds represented by the general formula ("n) obtained by the production method having the physical constant nDi, 527.

When actually applying the compound of the present invention obtained as described above, it can be used as it is without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. Forms such as powders, wettable powders,
It is formulated into oils, emulsions, tablets, granules, fine granules, air seals, flowables, etc. and applied.

Examples of formulations are shown below. Table of Contents/Preparation Example 1 Powder 2 parts of the compound of the present invention (3), 88 parts of clay, and 1 part of talc
0 parts were thoroughly ground and mixed to obtain a powder having a base ingredient content of 2%.

Formulation Example 2 Wettable powder 30 parts of the compound of the present invention (4), ±45 parts of diatom, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate) and 2 parts of dispersing agent (calcium lignin sulfonate) were thoroughly ground and mixed. A hydrating agent having a base ingredient content of 3096% is obtained.

Formulation Example 3 Wettable powder Compound of the present invention (3) 50 parts, diatomaceous earth 45 parts, wetting agent (
285 parts of calcium alkylbenzenesulfonate) and 285 parts of a dispersant (calcium ligninsulfonate) were thoroughly ground and mixed to obtain a wettable powder containing 150% of the base ingredient.

Formulation Example 4 Emulsion 10 parts of the compound of the present invention (4), 80 parts of cyclohexanone, and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) are mixed to obtain an emulsion with a base agent content of 10%.

Generally active compounds in the above preparations! 1.0~
95.0%, preferably 2.0 to 80.096,
The application rate is usually 10 to 100'f per 10 are. Furthermore, the concentration used is preferably in the range of o, oos to 0.5%, but these usage amounts and concentrations vary depending on the dosage form, time of application, method, location, target disease, target crop, etc., so they are not limited to the above range. There is no problem in increasing or decreasing the amount without any problem.

Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.

Next, a test example will be given to further clarify the usefulness of the compound of the present invention as a horticultural fungicide.

Note that the control compounds are indicated by the common names shown in Table 5.

Notes (1) Commercially available herbicides Sho (2) Commercially available fungicides Test example 1 Cucumber powdery mildew control effect Cucumber seedlings were obtained in 90-capacity plastic pots with a sandy loam floor. A water-diluted solution of the test compound in the form of an emulsion or a wettable powder was sprayed on the foliage of the seedlings until a sufficient amount of droplets adhered to the leaf surface. After air-drying the chemical solution, seedlings were infected with chemical-resistant or sensitive cucumber powdery mildew fungus (Sphaerothecaful 1g1ne).
The conidial suspension of a) was inoculated by spraying. After cultivating this in a greenhouse for 10 days to develop disease, the disease state was observed.

The disease severity was calculated by the following method.

That is, depending on the appearance of lesions on the investigated leaves,
．． The disease was classified into an index of 2.4, and the disease severity was calculated using the following formula.

(Incidence index) (Infection state) 0...No bacterial flora or lesions observed on the leaf surface.

0, 5...Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area.

1: Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area.

2: Bacterial flora or lesions are observed on the leaf surface in less than 50% of the leaf area.

4...Bacterial flora or lesions are observed on the leaf surface over 50% of the leaf area.

Next, the control value was calculated using the following formula.

As a result, as shown in Table 6, the compound of the present invention has an excellent control effect against drug-resistant bacteria. did not show.

Table 6 Test Example 2 Effect on controlling sugar beet brown spot disease A 90-volume plastic pot was filled with sand wall soil, and 31 sugar beets (variety: Detroit Darkle 9do) were placed there.

After 20 days of cultivation in a greenhouse, the resulting seedlings were sprayed with a water-diluted solution of the test compound in the form of an emulsion or wettable powder until the droplets fully adhered to the leaf surface. After air-drying the chemical solution, seedlings were infected with drug-resistant or susceptible sugar beet brown spot fungus (Cercospo
ra beticola) conidial a#R solution was spray inoculated. After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, the disease state was observed.

The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As shown in Table 7, similar to the results of Test Example 1, the compound of the present invention showed an excellent control effect against drug-resistant bacteria. All agents showed almost no control effect.

Test Example 3 Pear scab control effect A 90-sized Blasti pot was filled with mixed soil of peat moss and sandy loam, and seeds collected from pear fruits (variety: Chojube) were sown.

This was cultivated in a greenhouse for 20 days, and a water diluted solution of the test compound in the form of an emulsion or wettable powder was sprayed on the foliage of the seedlings until the droplets sufficiently adhered to the leaf surface. After air-drying the chemical solution, seedlings were infected with drug-resistant or susceptible pear scab fungus (Venturia na.
A conidial suspension of C. shicola was inoculated by spraying. This was placed under humid conditions at 20°C for 3 days, and then
The plants were cultivated under fluorescent lighting for 20 days to induce disease.

The disease onset detection method and control value calculation were the same as in Test Example 1.
did.

As a result, as shown in Table 8, the compound of the present invention showed an excellent control effect against drug-resistant bacteria, but the commercially available fungicides benomyl and thiophanate methyl did not show a control effect.

Test Example 4 Effect on controlling bean nut brown spot disease A 100-volume plastic pot was filled with sandy loam, and bean nuts (variety: Nichiba semi-erect) were sown. 14 in the greenhouse
After cultivation for one day, a water-diluted solution of the test compound in the form of an emulsion or wettable powder was sprayed on the foliage of the seedlings at 10 times per pot. After air-drying the chemical solution, the seedlings are infected with the drug-resistant or susceptible "Cercospora arach" fungus.
idieola) was inoculated by spraying.

After cultivating this in a greenhouse for 10 days under humid conditions by covering it with a vinyl cover, the disease state was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As a result, as shown in Table 9, the compounds of the present invention showed an excellent control effect against drug-resistant bacteria, but the commercially available fungicides benomyl and thiophanate methyl did not show a control effect.

Table 9 Test Example 5 Cucumber gray mold control effect A 90-volume plastic pot was filled with sandy loam, and cucumbers (variety:
Sumo Hanpaku) was sown. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. A water diluted solution of the test compound in the form of an emulsion or wettable powder was added to the seedlings at 10 d per pot.
It was sprayed on foliage and foliage. After the chemical solution is air-dried, the seedlings are infected with the chemical-resistant or sensitive gyucurly gray mold fungus (Botrytis).
cinerea) was inoculated by gluing (5 pieces in diameter) onto the leaf surface. The mice were placed in a humid environment at 20° C. for 3 days to develop disease, and then the state of disease development was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As a result, as shown in Table 10, the compound of the present invention showed an excellent control effect against these drug-resistant bacteria, but the commercially available fungicides benomyl and thiophanate methyl did not show a control effect.

Test Example 6 Cucumber vine blight control effect A 90rnl plastic port was filled with sandy loam, and cucumbers (variety: Sagami Hanshiro) were sown. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. A water diluted solution of the test compound in the form of an emulsion or a wettable powder was applied to the seedlings at 1 drop per pot.
0 - Sprayed on grass leaves. After air-drying the chemical solution, seedlings are infected with drug-resistant or sensitive cucumber vine blight fungus (Mycosphaere).
Ila melonis) was inoculated by pasting a cut plate (51 m in diameter) on the leaf surface. The mice were placed in a humid environment at 20° C. for 3 days to develop disease, and then the state of disease development was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1.

As a result, as shown in Table 11, the compound of the present invention showed an excellent control effect against drug-resistant bacteria, but the commercially available fungicides benomyl and thiophanate methyl did not show a control effect.

@Table 11 Test Example 7 Control effect on citrus back mold disease After washing tangerine fruit (variety: Unshu) thoroughly with water and air drying, the emulsion of the compound of the present invention or a control commercially available drug was diluted with water and added to a predetermined concentration to form a chemical solution. Soaked for 1 minute. After air-drying, a drug-resistant or sensitive citrus fungus (Penicillum ita)
licum) conidia were suspended in water and inoculated by spraying onto the fruit surface.

After inoculation, the seeds were kept in a humid room for 14 days, and the degree of disease onset was investigated using the disease index of 0.1.2.3.4.5 as shown below.

(Infection status) (Infection index 0 No lesions observed O20% of fruit surface area
Lesions are observed in less than 1# Lesions are observed in less than 2Nθ% 2# 4NO% 13 I 6 houses 40% 48
Lesions are observed in 0% or less 5 The severity and control value were calculated in the same manner as in Test Example 1.

As a result, as shown in Table 12, one compound of the present invention showed an excellent control effect against drug-resistant bacteria, whereas commercially available fungicides benomyl and thiophanate methyl did not show a control effect.

Table 12 Test Example 8 Phytotoxicity test on crops A 150-volume plastic pot was filled with sandy loam, and wheat (product name: Norin No. 61), apple (product temperature: Kogyoku), and peanut (variety Nichiba Hantatsu) 4 seeds of each species) were sown and cultivated in a greenhouse. A water-diluted solution of the test compound in the form of an emulsion or wettable powder was sprayed on the stems and leaves of the obtained seedlings. After spraying, the plants were returned to the greenhouse, and after cultivation for 10 days, the presence or absence of phytotoxicity was investigated using the following criteria.

Standards for degree of drug damage (Severity) (Symptom) -No abnormalities.

10. Abnormalities due to chemical damage are observed in some of the crops.

→G Abnormalities due to chemical damage are observed throughout the crop.

＋　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　Death.

As a result, as is clear from Table 13, the compound of the present invention had no harmful effect on crops, whereas the commercially available herbicide with a chemical structure similar to that used as a control had the same harmful effect.

Table 13

Claims (5)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a nitro group, Cyano group, or general formula -AR_1, -
CH_2OR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
, -COOR_2, ▲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. ▼ Or -NHCH
Represents a substituent represented by =N-OR_2 (where R
_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 and R_3 represent a lower alkyl group, R_4 represents a hydrogen atom or a lower alkyl group, and A and A' represent an oxygen atom or a sulfur group. represents an atom,
n represents 2, 3 or 4. ). However, X and Y do not represent a hydrogen atom or a halogen atom at the same time. R is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or the general formula -A″-R_5, ▲numerical formula,
There are chemical formulas, tables, etc. ▼ or -CH_2OR^6
(where R_5 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, or a lower haloalkyl group, and A'' represents an oxygen atom or R' represents a sulfur atom, and R_6 represents a lower alkyl group.) R' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group, or hydrogen. Represents an atom.] A formamide oxime derivative represented by (2) General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, X and Y are hydrogen atoms, halogen atoms, lower alkyl groups, lower alkenyl groups, lower alkynyl groups, lower haloalkyl groups, General formula ▲ Numerical formulas, Chemical formulas, tables, etc. are available ▼ Nitro group, cyano group, or general formula -AR_1, -CH_
2OR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -C
OOR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH=N-OR_4, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc. Yes▼Or-NHCH
Represents a substituent represented by =N-OR_2 (where R
_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 and R_3 represent a lower alkyl group, R_4 represents a hydrogen atom or a lower alkyl group, A and A' are an oxygen atom or sulfur represents an atom, n is 2
, 3 or 4. ). However, X and Y do not represent a hydrogen atom or a halogen atom at the same time. R is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or the general formula -A″-R_5, ▲numerical formula,
There are chemical formulas, tables, etc. ▼ or -CH_2OR_6
represents a substituent represented by (here, R_5 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, or a lower haloalkyl group, and A'' represents an oxygen atom or (R_6 represents a lower alkyl group.) R″ represents a lower alkyl group. ] A compound represented by the general formula R'-ONH_2 [wherein R' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group] Or represents a hydrogen atom. [In the formula, X, Y, R and R' are as described above. ] A method for producing a formamide oxime derivative represented by: (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are hydrogen atom, halogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, nitro group, cyano group , or general formula -AR_1, -CH_
2OR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -C
OOR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH=N-OR_4, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc. Yes▼Or-NHCH
Represents a substituent represented by =N-OR_2 (where R
_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 and R_3 represent a lower alkyl group, R_4 represents a hydrogen atom or a lower alkyl group, and A and A' represent an oxygen atom or a sulfur group. n represents an atom; n represents 2, 3 or 4; )
. However, X and Y do not represent a hydrogen atom or a halogen atom at the same time. A" represents an oxygen atom or a sulfur atom. R" represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group, or a hydrogen atom. . ] A compound represented by the general formula R'_5-Z [wherein R'_5 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, or a lower haloalkyl group. Z represents a leaving group. [In the formula, X, Y, R', A'' and R'_5 are as described above. ] A method for producing a formamide oxime derivative. (4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are hydrogen atom, halogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, nitro group, cyano group , or general formula -AR_1, -CH_
2OR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -C
OOR_2, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, -CH=N-OR_4, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas, tables, etc. ▼ Or represents a substituent represented by -NHCH=N-OR_2 (where R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, and R_2 and R_3
represents a lower alkyl group, R_4 represents a hydrogen atom or a lower alkyl group, A and A' represent ■■■■■■■■, an oxygen atom or a sulfur atom, and n represents 2, 3 or 4) . However, X and Y do not represent a hydrogen atom or a halogen atom at the same time. R is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or the general formula -A″-R_5, ▲There are numerical formulas, chemical formulas, tables, etc.▼ or -CH_2OR_
6 (where R_5 is a hydrogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group,
Represents a lower alkoxyalkyl group, lower cyanoalkyl group, or lower haloalkyl group, A'' represents an oxygen atom or a sulfur atom, and R_6 represents a lower alkyl group.)
. A compound represented by the general formula R''-Z [wherein R'' is a lower alkyl group, a lower alkenyl group,
Represents a lower alkynyl group, lower haloalkyl group, lower haloalkenyl group, lower haloalkynyl group or lower cyanoalkyl group. Z represents a leaving group. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by Method for producing formamide oxime derivatives. (5) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are hydrogen atom, halogen atom, lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, nitro group, cyano group, or general formula -AR_1, -CH_
2OR_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -C
OOR_2, ▲ 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, chemical formulas There are tables, etc. ▼ or -NHCH
Represents a substituent represented by =N-OR_2 (where R
_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 and R_3 represent a lower alkyl group, R_4 represents a hydrogen atom or a lower alkyl group, A and A' are an oxygen atom or a sulfur atom , where n is 2
, 3 or 4. ). However, X and Y are not hydrogen atoms or halogen atoms at the same time. R is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or the general formula -A″-R_5, ▲numerical formula,
There are chemical formulas, tables, etc. ▼ or -CH_2OR_6
represents a substituent represented by (here, R_5 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, or a lower haloalkyl group, and A″ represents an oxygen atom or Represents a sulfur atom, R
_6 represents a lower alkyl group. ). R' represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group, or a hydrogen atom. ] An agricultural and horticultural fungicide characterized by containing a compound represented by the following as an active ingredient.