JPS61291560A - Formamidoxime derivative, production thereof and agricultural and horticultural germicide containing said derivative as active constituent - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [X is halogen, lower alkyl, lower haloalkyl, nitro, cyano, etc.; Y is expressed by formula IV (A and A' are 0 or S; R1 is lower alkyl, lower alkenyl, lower alkynyl, etc.) or formula V (R2 is lower alkyl), etc.; R is H, lower alkyl, lower alkenyl, etc.; R' is lower alkyl, lower alkenyl, lower cyanoalkyl, etc.]. EXAMPLE:N-( 3-Chloro-4-allyloxy-5-methoxycarbonylaminophenyl )-N'-methoxy formamidine. USE:An agricultural and horticultural germicide capable of exhibiting selective germicidal effect on plant pathogenic germs, etc., exhibiting resistance to cyclic imide based germicides. PREPARATION:A compound expressed by formula II (R'' is lower alkyl) is reacted with a compound expressed by formula III in an organic solvent, e.g. methanol or ethanol, to afford the aimed compound expressed by formula I.

Description

Detailed Description of the Invention The present invention relates to a compound of the general formula CI) [wherein, or alkoxycarbonyl group.

Or it represents a substituent represented by -NH-CH,N-0R2 (where ^ and A' represent an oxygen atom or a sulfur atom, and R1 is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower haloalkyl group) represents,
R2 represents a lower alkyl group.

K represents a hydrogen atom, a lower cycloalkylalkyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group.

Skin 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. The present invention relates to a formamide oxime derivative (hereinafter referred to as the compound of the present invention) represented by the following formula, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.

General formula [! ] The formamide oxime derivatives represented by are benosaryl [methyl 1-(butylcarbamoyl)benzimidazole-2-yl-bamate], fuberidazole (2-(2-furyl)benzimidazole), and thiabendazole [2-(4-furyl)benzimidazole]. thiazolyl) benzimidazole], carpendazim [methyl benzyl main dacilyl 2-yl carbamate], thiophanate methyl (1
, 2-bis(3-methoxycarbonyl-2-thioureido)benzene], thiophylbenzene)(1,2-bis(3-
benzimidazole theophonate fungicides such as ethoxycarbonyl-2-thioureido)benzene], and brosielectron (N(a' m s'-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dimethyl carboxyimide], iprodione (3-(3',
5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2゜4-dione], vinclozolin (3-(3', 5'-dichlorophenyl)-5-
Methyl-5-vinyloxazolidine-2,4-dione]
, ethyl (R5) -3-(a',5'-dichlorophenyl)-5-methyl-2,4-dioxoxazolidine-5-carboxylate and other plant pathogenic bacteria that are resistant to cyclic imide fungicides and others. It is characterized by a strong selective bactericidal effect against filamentous fungi (hereinafter referred to as drug-resistant bacteria).

The present inventors 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 [I].

Examples of drug-resistant bacteria for which the compound of the present invention exhibits a strong bactericidal effect include Podophleb bacterium
ra 1eoucotr! cha), Sclerosis bacillus (Ve
Venturia nashicolm (Venturia nashicolm), Venturia nashicolm (8cl-erotinim mali), and Gloeosp.

rium kaksu, peach gray layer disease fungus (Sclerot)
iniacinere, Cladoipo
Rium carpoph-41um), Botrytiscinerea, Eisinoe simpelini, Glomerella cingulat,
Cercospora beti
cola), bean nut brown spot fungus (Cercospo
ra arachidicol, black astringent fungus (Cerc
ospora pertonatus, barley udon ξ disease fungus (Erysiphe griminis f,
sp.

hordei), eye spot fungus (Cercos
porella herpotrichoides),
Fusarium nivale, wheat powdery mildew (Erysiphegrminis)
f, sp, trit5C, cucumber powdery mildew fungus (Sph@erotheca fuligine)
Mycosphaerellsi m.
elonis), Botrytis c.
inerea), C1adospor-r.
i um cu cu mer 1 num), tomato leaf mold fungus (Cladosporlum ful
vum), Botrytis cin
Strawberry powdery mildew fungus (Sphaeroth)
eca humulli, hop gray mold fungus (Bot
rytls cinerea), tobacco powdery mildew (Erysiphe cichoracearum)
, Diplocarpon rogu
e), [Elsinoe fawc
etii), blue mold 11j (Panicilliu
mitalicum), green mold fungus (Penici)
Examples include lliumdigl (tortoise tum).

As a result of further studies, it was found that the compounds of the present invention are effective in controlling rice blast fungi (Pyricularia oryzie) and the like, regardless of the presence or absence of drug resistance.

Examples of the compounds of the present invention are shown in Table 1.

The compound of the present invention can be produced, for example, by the method shown in the reaction formula below.

CI) [In the formula, X, Y, R and the terminus are as described above.

Bi represents a lower alkyl group. 〕■ General formula〔! ], where λ is represented by 〆'' (IV) (V) CI) [In the formula,
represents a lower cycloalkylalkyl group, lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, lower alkoxyalkyl group, lower cyanoalkyl group, lower haloalkenyl group or lower haloalkynyl group. Z represents a leaving group. ] Examples of the above-mentioned leaving group include mesyloxy group, tosyloxy group, and halogen atom.

(2) In general formula (1), when ' is represented by 〆''' in the substituent [wherein, X, Y, R and Z are as described above.R
#I/# 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, or a lower cyanoalkyl group. ] That is, in the method shown in reaction formula (II), general formula (II)
The compound represented by the formula (III) is reacted with the compound represented by the general formula (III) 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.

■If the reaction is carried out using a compound in which the mouse is a hydrogen atom or the terminus is a hydrogen atom, the general formula (IV) is obtained.
Alternatively, a compound represented by [■] can be produced. The compound represented by the general formula [■] or (Vl) can be obtained by reacting the compound represented by the general formula [v] or the general formula [■] according to the method shown in the reaction formula (1) or (2). The reaction is usually carried out in an organic solvent in the presence of an acid binder at a temperature ranging from 0 to 40°C, preferably from 5°C to room temperature, for 1 to 2 hours.

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

The compound represented by the general formula (II) 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, NMR, and MASJ.

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

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

Preparation Example υ 2.0O11 of O-methylhydroxyamine hydrochloride was added 1N at 0<0>C to a methanol solution of sodium methoxide prepared from 0.55I of sodium and 50% of methanol. Here, ethyl N-(3-chloro-4-allyloxy-5-methoxycarbonylaminophenyl)formy [date 7.47
, F was added. After stirring under reflux for 1 hour, the mixture was poured into ice water and extracted with ethyl acetate.

After washing the organic layer with water and drying with anhydrous magnesium sulfate,
The solvent was distilled off under reduced pressure. The obtained crude product was purified by column chromatography using basic alumina, toluene, and ethyl acetate to obtain N-(3-chloro-4-allyloxy-5-methoxycarbonylaminophenyl)-d
-Methoxyformamidine 4.39F was obtained.

"22" 1.5698 The structure of the compound was determined from the results of spectral analysis such as IR, NMR, and MAS8. 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.

Examples of compounds produced based on such a production method are shown in Table 3.

Reference production example 3-chloro-4-allyloxy-5-methoxycarbonylaminoaniline 8.53 Jl, ethyl orthoformate 9.
851! and ethyl acetate 197- were heated to 70 to 80° C. while stirring and mixing, and ethanol produced during the reaction was distilled off as an azeotrope with ethyl acetate at normal pressure.

When there was almost no distillate, the reaction temperature was raised to 100°C, and heating, stirring, and distillation were continued for about 1 hour.
Excess ethyl orthoformate was distilled off at 5-20 mHg and 50-60°C to obtain the crude intermediate ethyl N-(3-chloro-4-allyloxy-5-methoxycarbonylaminophenyl).
Obtained formimidate. This was purified by column chromatography using a basic alkaline solution and toluene to obtain the target compound 10.9, f.

, CDCl! NMR, δ3y,7o(s,tH), 7.
26 (d.

MS IH), 6.70 (d, IH), 5.10-6
．． 40 (m, 3H), 4.50 (d, 2H).

4.30((1,2H), 3.78(1,3H)
#1.34 (t, 3H) Table 4 shows examples of compounds represented by the general formula (II) obtained by such a production method.

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 and applied in oils, emulsions, tablets, granules, microgranules, aerosols, flowables, etc.

Examples of formulations are shown below. Note that parts represent parts by weight.

Formulation Example 1 Powder 2 parts of the compound of the present invention (1), 88 parts of clay, and 1 part of talc
0 parts were thoroughly ground and mixed to obtain a powder containing 2 parts of the main ingredient.

Formulation Example 2 Wettable powder +4130 parts of the compound of the present invention, ±45 parts of diatoms, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate) and 2 parts of dispersing agent (calcium lignin sulfonate) are thoroughly ground and mixed to form a main ingredient. A quantity of 30% hydrating agent is obtained.

Formulation Example 3 Wettable powder 50 parts of the compound of the present invention, diatom ±45 parts, wetting agent (
2.5 parts of calcium alkylbenzenesulfonate) and 2.5 parts of a dispersant (calcium ligninsulfonate) were thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 50q1.

Formulation Example 4 Emulsion 10 parts of the present compound T4), 80 parts of cyclohexanone, and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) are mixed to obtain an emulsion containing 110% of the base ingredient.

The above formulations generally contain from 1.0 to 1.0% by weight of active compound.
95.0%, preferably 2.0-80.0%,
The application rate is usually 10 to 1001 I per 10 are. It is preferable that the concentration used for the bleaching agent is in the range of 0.005 to O,S*, but the amount and concentration used vary depending on the dosage form, time of application, method, location, target disease, target crop, etc. There is no problem in increasing or decreasing the amount without regard to the above.

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

Next, test examples will be given to further clarify the usefulness of the compound of the present invention as an agricultural and horticultural fungicide.

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

Table 5 Test Example 1 Cucumber Powdery Mildew Control Effect A 90-volume plastic pot was filled with sandy loam, and cucumber (variety:
Sumo Hanpaku) was sown. This was cultivated at room temperature for 8 days to obtain Chie cucumber seedlings with expanded cotyledons. 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 exposed to chemical-resistant or susceptible cucumber powdery mildew (Sph).
aerothecafuliginea) was spray inoculated with a conidial suspension. The plants were cultivated in a greenhouse for 10 days to develop the disease, and then the disease state was observed.

The disease severity was calculated by one method below.

That is, depending on the appearance of lesions on the questionnaire, 0.0.5.1
．． The disease was classified into an index of 2.4, and the disease severity was calculated using the following formula.

(Incidence Index) (Incidence U> O: 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 squares 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% or more 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 showed an excellent control effect against drug-resistant bacteria. Herbicides showed little control effect.

Table 6 Test Example 2 Effect on controlling sugar beet brown spot disease A 90-volume plastic pot was filled with sandy loam, and sugar beet (variety: Detroit Dark Red) was sown. After 20 days of cultivation in a greenhouse, the seedlings were sprayed with a water-diluted solution of the test compound in the form of an emulsion or a wettable powder until the droplets sufficiently adhered to the leaf surface. After the chemical solution is air-dried, the drug-resistant or susceptible sugar beet brown spot fungus (Cercospora
beticolm) was inoculated by spraying with a conidial suspension. Cover this with a vinyl cover to create a humid condition.
After cultivating in a greenhouse for 10 days, 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 commercially available herbicides showed almost no control effect. Table 97 Test Example 3 Effect on Pear Scotch Disease Control Effect Beetroot was cultivated in a greenhouse for 20 days in a 90 mJ plastic pot, and droplets of a water-diluted solution of the test compound in the form of an emulsion or wettable powder were applied to the seedlings obtained. It was sprayed on foliage until it fully adhered to the leaf surface. After air-drying the chemical solution, seedlings were infected with drug-resistant or susceptible pear scab fungus (Venturia na@hic).
o1m) was inoculated by spraying with a conidial suspension. The plants were placed under humid conditions at 20° C. for 3 days, and then cultivated under fluorescent lamp illumination at 20° C. for 20 days to induce disease.

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

As a result, as shown in Table 8, the compound of the present invention showed an excellent control effect against drug-resistant bacteria.
and methyl thiononate showed no control effect.

Table 8 Test Example 4 Peanut brown spot control effect A plastic pot of 100 tR capacity was filled with sandy loam, and peanut brown spot (
The cultivar Nichiba semi-erect) was sown. After 14 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 at a rate of 10 mj per pot. After air-drying the chemical solution, the seedlings are exposed to drug-resistant or susceptible peanut brown spot fungi (Cercosp raarachidicol).
λ) was inoculated by spraying with a spore suspension.

After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, the state of disease onset 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 thiono 1 nate methyl did not show a control effect.

Table 9 Test Example 5 Disease control effect on cucumber gray power A 90-volume plastic pot was filled with sandy loam soil, 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 applied to seedlings of kernels per pot.
d! , sprayed on foliage. After air-drying the chemical solution, young seedlings were exposed to the chemical-resistant or sensitive cucumber gray mold fungus (Botrytis).
cinerea) bacterial flora section (diameter 511II)
was inoculated by pasting it on the leaf surface. The mice were incubated for 3 hours under humid conditions at 20° C. to develop the disease, and then 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 10, the compounds of the present invention showed an excellent control effect against drug-resistant bacteria, but the commercially available fungicides benomyl and thiono 1 nate methyl did not show a control effect.

Table 10 Test Example 6 Cucumber vine blight control effect 90-volume plastic pots were filled with lζ sandy loam soil, 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 a wettable powder was applied to the seedlings at 10 μl per pot.
Sprayed on foliage. After air-drying the chemical solution, an animation of the drug-resistant or sensitive cucumber vine blight fungus (Mycosphaerell
A melonis) bacterial lawn section (5 m in diameter) was pasted onto the leaf surface and inoculated. 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 compounds of the present invention showed an excellent control effect against drug-resistant bacteria, but the commercially available fungicides benomyl and thiono 1 nate methyl did not show a control effect.

Table 11 Test Example 7 Effect on mandarin blue mold disease control After thoroughly washing mandarin fruits (variety: Unshu) with water and air drying,
An emulsion of the compound of the present invention or a control commercially available drug was diluted with water and immersed for 1 minute in a drug solution to a predetermined concentration. After air-drying, the drug-resistant or susceptible Penicillum fungi
mitalicum) 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.

(Disease condition) (Infection index) No lesions observed 0 Lesions observed on less than 20% of the fruit surface area 1// Lesions observed on less than 20-40% 2〃40-60% l
3 hits 60-80 hits
4. Lesions are observed in 80 inches or more. 5. The degree of attack and control value were calculated in the same manner as in Test Example 1.

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

Table 12 Test Example 8 Phytotoxicity test on crops 150-volume plastic pots were filled with sandy loam soil, and wheat (variety: Norin No. 61), apple (variety: Kogyoku), and peanuts (variety: Nichiba semi-erect) Each was 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 placed in the greenhouse again, and after cultivation for 10 days, the presence or absence of phytotoxicity was investigated according to 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.

- Abnormalities due to chemical damage are observed throughout the crop.

Bones wither and die due to chemical damage.

As a result, as is clear from Table 13, the compound of the present invention did not have a phytotoxic effect on crops, whereas a commercial herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.

Table 13

Claims (5)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, a lower alkyl group, a lower haloalkyl group, a nitro group, a cyano group, a lower alkoxy group,
Represents a lower alkoxymethyl group, acyl group or alkoxycarbonyl group. Y represents a general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or a substituent represented by -NH-CH=N-OR_2 (Here, A and A' are Represents an oxygen atom or a sulfur atom, R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 represents a lower alkyl group. R is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower Represents an alkynyl group, lower haloalkyl group, lower alkoxyalkyl group, lower cyanoalkyl group, lower haloalkenyl group, or lower haloalkynyl group. R' is a lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, lower halo represents an alkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group, or a hydrogen atom.] A formamide oxime derivative represented by the following. (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, a lower alkyl group, a lower haloalkyl group, a nitro group, a cyano group, a lower alkoxy group,
Represents a lower alkoxymethyl group, acyl group or alkoxycarbonyl group. Y represents a general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or a substituent represented by -NH-CH=N-OR_2 (Here, A and A' are Represents an oxygen atom or a sulfur atom, R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 represents a lower alkyl group. R is a hydrogen atom, a lower cycloalkylalkyl group, a lower alkyl group , represents a lower alkenyl group, lower alkynyl group, lower haloalkyl group, lower alkoxyalkyl group, lower cyanoalkyl group, lower haloalkenyl group, or lower haloalkynyl group. R'' represents a lower alkyl group.]
A compound represented by the general formula R'-ONH [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. ] General formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, X, Y, R and R' are as described above. ] A method for producing a formamide oxime derivative. (3) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, a lower alkyl group, a lower haloalkyl group, a nitro group, a cyano group, a lower alkoxy group,
Represents a lower alkoxymethyl group, acyl group or alkoxycarbonyl group. Y represents a general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or a substituent represented by -NH-CH=N-OR_2 (Here, A and A' are represents an oxygen atom or a sulfur atom; R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group; R_2 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] and a compound represented by the general formula R'''-Z [wherein R''' is lower cycloalkyl Represents an alkyl group, lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkyl group, lower alkoxyalkyl group, lower cyanoalkyl group, lower haloalkenyl group, or lower haloalkynyl group. Z represents a leaving group.] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [wherein, X, Y, R′″ and R′ are as described above], which is characterized by reacting with a compound represented by Method for producing formamide oxime derivatives. (4) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, a lower alkyl group, a lower haloalkyl group, a nitro group, a cyano group, a lower alkoxy group,
Represents a lower alkoxymethyl group, acyl group or alkoxycarbonyl group. Y represents a general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or a substituent represented by -NH-CH=N-OR_2 (Here, A and A' are Represents an oxygen atom or a sulfur atom, R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 represents a lower alkyl group. R is a hydrogen atom, a lower cycloalkylalkyl group, a lower alkyl group , a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group. ] and the compound represented by the general formula R″″-Z [ In the formula, 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 shown below ▼ [In the formula, X, Y, R and R″″ are as described above. ] A method for producing a formamide oxime derivative. (5) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X is a halogen atom, a lower alkyl group, a lower haloalkyl group, a nitro group, a cyano group, a lower alkoxy group,
Represents a lower alkoxymethyl group, acyl group or alkoxycarbonyl group. Y represents a general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or a substituent represented by -NH-CH=N-OR_2 (Here, A and A' are Represents an oxygen atom or a sulfur atom, R_1 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group, R_2 represents a lower alkyl group. R is a hydrogen atom, a lower cycloalkylalkyl group, a lower alkyl group , represents a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a lower cyanoalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group. R' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, An agricultural and horticultural fungicide characterized by containing as an active ingredient a compound represented by a lower haloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, a lower cyanoalkyl group, or a hydrogen atom.