JPS59167556A - N-phenylcarbamate compound, its preparation and agricultural and horticultural fungicide containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [X and Y are H, halogen, lower alkenyl, lower alkoxy, cyano, etc.; Z is H, F, or OR<5> (R<5> is lower alkenyl, lower alkynyl, etc.); A and B are O or S; R<1> is cyano, SR<6> or OR<6> (R<6> is H, lower alkenyl, naphthyl, etc.); R<2> is lower alkenyl, lower cycloalkyl, etc.]. EXAMPLE:Isopropyl N-phenylsulfenyl-N-(3,4-diethoxy-5-methylphenyl)-carbamate. USE:An agricultural and horticultural fungicide. Effective to the pathogenic fungi of powdery mildew, scab, blossom blight, etc. PREPARATION:The compound of formula I can be prepared by reacting the aniline derivative of formula II with the compound of formula III in a solvent such as benzene, tetrahydrofuran, etc. in the presence of a dehydrochlorination agent (e.g. pyridine, triethylamine, etc.) under cooling or heating at 0-150 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula CI] wherein X and Y are the same or different, a hydrogen atom,
represents a halogen atom, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxyl group, or a cyano group, or represents a lower alkyl group optionally substituted with a halogen atom, a hydroxyl group, or a cyano group, or , general formula -CH20R''-COR, -
CH=N-OR represents a substituent represented by li -CONR8R' (where R8 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower haloalkyl group).

R4 represents a hydrogen atom or a lower alkyl group.

n represents 2, 3 or 4. ). However, X and Y
except when simultaneously represents a hydrogen atom.

Z represents a hydrogen atom, a fluorine atom, or a substituent represented by the general formula -0R6 (wherein, R6 represents a lower alkenyl group or a lower alkynyl group, or a halogen atom, a lower alkoxyl group, or a lower cycloalkyl group). (Represents an optionally substituted lower alkyl group.)
.

A and B are the same or different and represent an oxygen atom or a sulfur atom.

R1 is a cyano group, or has the general formula -SR' or -
ORC7f< (here, R6 represents a hydrogen atom, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkyl group, a lower haloalkynyl group, or a naphthyl group, or a halogen atom, a cyano represents a phenyl group which may be substituted with a nitro group, a lower alkyl group, a carboxyl group or a lower alkoxyl group, or a halogen atom, a cyano group, a lower alkoxyl group, an amino group, a lower alkylamino group or a phenoxy group represents a lower alkyl group which may be substituted with (here, M'-+ represents an oxygen atom or a sulfur atom, and R represents a lower alkenyl group, a lower alkynyl group, It represents a heteroaryl group, or a phenyl group optionally substituted with a halogen atom or a lower alkyl group, or even if it is substituted with a halogen atom, a cyano group, a lower alkoxyl group, or a lower cycloalkyl group. (R represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyl group).

R2 represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group, or a halokene atom, a cyano group, a lower alkoxyl group, a lower alkenyloxy group, or a lower haloalkoxyl group! represents a lower alkyl group which may be substituted with a phenoxy group, a lower aralkyloxy group, a phenyl group, or a lower cycloalkyl group. ] Thea T < Sallehephenylcarpamate compound (
The present invention relates to compound 11 of the present invention), its production method, and an agricultural and horticultural fungicide containing it as an active ingredient.

In the compound of the present invention represented by the above general formula [1], “
"Lower" means that the number of carbon atoms is 6 or less, and "lower" means that the number of carbon atoms is 6 or less, and "
"Heteroaryl" means furyl, chenyl, pyrrolyl,
Pyrazolyl, imidazolyl, 1,2.8-triazolyl, 1,2.4-triazolyl, oxasilyl, isoxasilyl, thiazolyl, isothiazolyl, benzofuranyl, benzothiophenyl, indolyl, benzimidazolyl, imidazolyl, benzoxasilyl, l, 2 -Means a 5-membered ring, a benzene-fused 5-membered ring, or a 6-membered ring functional group such as benzoxasilyl, benzothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, etc.

The present inventors have conducted intensive studies on compounds that exhibit bactericidal effects against plant pathogenic bacteria and other filamentous fungi (hereinafter referred to as drug-resistant bacteria) that are resistant to benzimidazole/thiophanate fungicides and cyclic imide fungicides. As a result, it was found that the N-phenyl carbamate compound represented by the general formula [I] is effective against drug-resistant bacteria.

The N-phenyl carbamate compound represented by the general formula [I] is benomyl [methyl 1-(bu).

(Tylcarbamoyl) Benzyl E Tasso Jl/2-ylcarbamate], Fuberidazole [2-(2-furyl)benzimidazole], Thiabendazole [2-(' 4
-thiazolyl)benzimidazole], carpendazim [methyl benzimidazole-2-yl-bamate], thiophanate methyl [1,2-bis(3-methoxycarbonyl-2-thioureido)benzene], thiophanate [1,2-bis(8- ethoxycarbonyl-2
-benzimidazole/thiophanate acidicides such as benzene], and procymidone [N-
(8',5'-dichlorophenyl)-1-,2-dimethylcyclopropane-1,2-dicarboximide], iprodione [8-(8',5'-dichlorophenyl)-
1-isopropylcarbamoylimidazolidine-2,4
-dione], vinclozolin [3-(3', 5'-
dichlorophenyl)-5-methyl-5-vinyl-oxazolidine-2,4-dione], ethyl (R3)-s-(
3', 5'-dichlorophenyl)-5-methyl-2,
It is characterized by a strong selective bactericidal effect against plant pathogenic bacteria and other filamentous fungi that are resistant to cyclic imide fungicides such as 4-dioxoxazolidine-5-carboxylate.

As mentioned above, the compound of the present invention exhibits a strong bactericidal effect selectively against bacteria that are resistant to benzimidazole/thiophanate fungicides. Can be used to control resistant countries. For example, powdery mildew of apples (Podosphaera 1eucotrich)
a), Vencuria 1naeq
uaJjs), pear scab fungus (Venturia
nashicola), Monilia disease fungus (Scle-
rosinia mali), oyster anthracnose (Gl
oeosporiumkaki), peach blight fungus (
5clerotinia cinerea), Cladosporium carpophilu
m), Botrytis ci
nerea), Eisinoe am
pelina), late rot fungus (Glome-rell)
a cingulaza), brown spot disease of sugar beet (
Cercospora beticola ), peanut brown spot fungus (Cercospora arach
idicola), Cercospora
persOIlata), barley powdery mildew (Erysiphe graninis f.
, sp, hordei), ai, sp, NJ 丙灭
-cboides), Fusariu
zn n1vale), wheat powdery mildew (Er
ysiphe graminis f'.

sp, vritici), powdery mildew of cucumber.
(5phaerotheca ful 1g1nea
), 1aycosphaerella melonis
), Botyvis cioer
ea), Cladosporium cucu
nle r inum), tomato leaf mold fungus (C1
adosp-orium fulvum), gray mold fungus (Botrytiscjnerea), strawberry powdery mildew fungus (5phaerotbeca1+umuli)
), Botrytiscin
area), tobacco powdery mildew (Erysiph
ecchoracearum), rose scab fungus (
Diplocarponrosae), tangerine scab fungus (Elsinoe fawcetii), blue mold fungus (PeniciLIium 1taliturn)
), Penicjllium d
It can be used to control drug-resistant bacteria such as P. gitatum).

Next, examples of the compounds of the present invention represented by the general formula [I] are as follows, but the compounds of the present invention are not limited to these.

Next, a method for producing the compound of the present invention will be described.

The compound of the present invention can be produced, for example, by the following method.

Production method (a) General formula [1B [In the formula, X, Y, Z and R1 have the same meanings as above. ] Aniline conductor and general formula [岨CzC-A-R
2[J [wherein A, B and R2 represent the same meanings as above.

] A production method that involves reacting with the compound shown in

This reaction is generally carried out in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethylformamide, or a mixture thereof; By using a dehydrochlorination agent such as sodium oxide or potassium hydroxide, high yield can be achieved.

The reaction is cooled or heated (0 to 150°C) as necessary.
), the reaction can be completed within 10 hours and the desired product can be obtained in good yield.

In addition, in the general formula CI], substituent R1 is 16'6
' General formula-3R (wherein R represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group or a naphthyl group,
or represents a phenyl group optionally substituted with a halogen atom, a cyano group, a nitro group, a lower alkyl group, a carboxyl group, or a lower alkoxyl group, or
represents a lower alkyl group optionally substituted with a halogen atom, a cyano group, a lower alkoxyl group, an amino group, a lower alkylamino group, or a phenoxy group, or
Represents a group of the general formula (where M represents an oxygen atom or a sulfur atom, and R7 represents a lower alkenyl group, lower alkynyl group, or heteroaryl group, or may be substituted with a halogen atom or a lower alkyl group) R represents a phenyl group, or a lower alkyl group optionally substituted with a halogen atom, a cyano group, a lower alkoxyl group, or a lower cycloalkyl group;
8 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyl group. )
. ), the compound of the present invention can be produced, for example, by the following method.

Production method (b) General formula [IV] [In the formula, X, Y, Z, A, B and R represent the same meanings as above. ] An N-phenyl carbamate compound represented by the general formula [V] R''-3-W [v] f [wherein R represents the same meaning as above and W represents a halogen atom] A production method that involves reacting with a compound.

Furthermore, in the general formula [I], the substituent R1 is v General formula 10R (in the formula, R6 represents the same meaning as above).

), the compound of the present invention can be produced, for example, by the following method.

Manufacturing method CC) General formula [■] [In the formula, X, Y, Z, A, B and R represent the same meanings as above. ] An N-phenyl carbamate compound represented by the general formula [■] R-W [■] [In the formula, R6 represents the same meaning as above, and W represents a halogen atom. ] A manufacturing method of reacting with a compound represented by:

In the above production methods (b) and (C), the reaction is generally carried out in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethylformamide, or a mixture thereof. We use dehydrohalogenating agents such as pyridine, triethylamine, diethylaniline, sodium hydroxide, potassium hydroxide, and sodium hydride, and if necessary, phase transfer catalysts such as tetrabutylammonium bromide and benzyltriethylammonium chloride. By this, high yield can be achieved.

The reaction is cooled or heated (0°C to 150°C) as necessary.
°C), the reaction can be completed within 10 hours and the desired product can be obtained in good yield.

Next, a manufacturing example will be shown.

Production Example 1 Isopropyl hephenylsulfenyl-N-(8,
Production of 4-jethoxy-5-methylphenyl)carbamate [according to production method (a)] N-phenylsulfenyl-N-8,4-jethoxy-5-methyl)aniline3.
1.591 f of isopropyl chloroformate and 1.94 f of N-diethylaniline were added to 24 g of toluene solution (80 ml) at 25°C with stirring.

After standing for 3 hours, the reaction mixture was poured into water and extracted with toluene. The toluene layer was washed with dilute hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene-tetrahydrofuran to obtain isopropyl N-phenylsulfenyl N-(8,4-jethoxy-5-methylphenyl)carbamate s, 'ts
I got y. (Yield 96%) nDI-559.6 Production Example 2 Isopropyl N-phenylsulfenyl-N-(8-
chloro-4-ethoxy-5-methoxymethylphenyl)
Production of carbamate [according to production method (b)]
0.249 of hydrogen 4tz sodium was added. 1.50 flfz of phenylsulfenyl chloride was added to the mixture while stirring at 25°C. Further, after being left at the same temperature for 3 hours, the reaction mixture was opened and extracted with toluene.

The toluene layer was washed with dilute hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and tetrahydrofuran to obtain isopropyl N5-phenylsulfenyl-N-(8-chloroni4-ethoxy-5-methoxymethylphenyl). ) Carbamate 8.97f was obtained.

(Yield 97%) nDl, 5591 Production Example 3 Isopropyl N-acetoxy-N-(3-chloro-4
-Ethoxy-5-methoxymethylphenyl)carbamate [according to production method (e)] Isopropyl N-hydroxy-N-(3-chloro-4
-Ethoxy-5-methoxymethylphenyl)carbamate a,isp was added with 30-acetic anhydride, and while stirring, 2
The mixture was heated to reflux for an hour. The reaction mixture was cooled, poured into water, and extracted with toluene. The toluene layer was washed with aqueous sodium bicarbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed liquid medium of toluene and tetrahydrofuran to obtain isopropyl N-acetoxy-N.
-(3-chloro-4-ethoxy-5-methoxymethylphenyl)carbamate 3.06f was obtained. Yield 85X
) n:' 1.5108 The compounds of the present invention thus obtained are shown in Table 2.

When actually applying the compound of the present invention obtained in this way, 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. It is applied in the form of a powder, wettable powder, oil, emulsion, tablet, granule, i-granule, aerosol, flowable, etc.

The above formulations generally contain i, o by weight of active compound.
~95.0" However, since the amounts and concentrations used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., there is no problem in increasing or decreasing them without being limited to the above ranges.

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

Examples of formulations are shown below.

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 having a base ingredient content of 2%.

Formulation Example 2 Wettable powder: 3 parts of sodium acid and 2 parts of dispersant (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 30%.

Formulation Example 3 Wettable powder 50 parts of the compound of the present invention (5), 45 parts of diatomaceous earth, wetting agent (
2.5 parts of calcium alkylbenzenesulfonate) and 215 parts of a dispersant (calcium ligninsulfonate) were thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 50%.

Formulation Example 4 Emulsion Compound of the Invention (7) l 0 parts, cyclohexanone 80
1 part and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether).

An emulsion with a drug content of 10% is obtained.

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 shown in Table 3 in general terms.

Table 3 Notes (1) Commercially available herbicides Notes (2) Commercially available fungicides Test example 1 Cucumber powdery mildew control effect A 90-capacity plastic pot was filled with sandy loam, and cucumbers (variety: Sumo Half-day) were sown. . This was cultivated at room temperature for 8 days to obtain a cucumber surface with expanded cotyledons. An emulsion of an emulsion of the compound of the present invention below prepared as an emulsion according to Formulation Example 4 and a water-diluted solution of a hydrating powder of a control compound were sprayed onto the foliage of the seedlings until a sufficient amount of droplets adhered to the leaf surface. After the chemical solution is air-dried, the seedlings are infected with chemical-resistant or sensitive cucumber powdery mildew fungi (5phaeroth).
ecaful 1g1nea) 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,
, 2.4, and the disease severity was calculated using the following formula.

(Infection 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 4, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and wild bacteria susceptible to benzimidazole/thiophanate fungicides or cyclic imide fungicides (hereinafter referred to as drug-susceptible bacteria) ) showed no control effect. On the other hand, none of the commercially available fungicides benomyl, thiophanate methyl, and carpendazim showed any control effect when inoculated with drug-resistant bacteria, but showed excellent control effects when inoculated with drug-susceptible bacteria.

Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.

Table 4! Test Example 2 Effect on controlling sugar beet brown spot disease A 90-volume plastic pot was filled with sandy loam soil, and droplets of a water-diluted solution of an emulsion of the present compound of sugar beet (variety: Detroit dark) and a hydrating powder of a control compound were added to the pot. After the chemical solution was air-dried, the seedlings were infected with chemical-resistant or sensitive sugar beet brown spot fungus (Cercosp).
ora beticola) was inoculated by spraying. The plants were covered with a vinyl cover to create humid conditions, and after being cultivated 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 5, similar to the results of Test Example 1, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria; It showed excellent control effect when inoculated with bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.

Table 5 Test Example 3 Pear scab control effect 9 A plastic bot was filled with a 7Ju mixture of peat moss and sandy loam, and seeds collected from a pear fruit type (variety: Nagakobu) were sown.

This was cultivated in a greenhouse for 20 days, and droplets of a water-diluted solution of an emulsion of the compound of the present invention prepared below and a hydrating powder of the control compound below, prepared according to Formulation Example 4, were applied to the seedlings for 7 minutes on the leaf surface. The grass was sprayed until

After air-drying the chemical solution, a conidial suspension of Venturia nashicola, which is resistant or susceptible to the drug, was extracted from the seedlings. 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 6, the compounds of the present invention had a significantly lower control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl were superior when inoculated with drug-susceptible bacteria. It showed a pesticidal effect.

Table 6 Test Example 4 Cucumber Gray Mold Control Effect A 90m capacity plastic pot was filled with sandy loam soil, and cucumbers (variety:
Sumo half day) was sown. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. A water diluted solution of an emulsion of the compound of the present invention described below and a hydrating powder of the control compound described below, prepared according to Formulation Example 4, was sprayed onto the foliage of the seedlings in an amount of 10 ml per pot. After air-drying the chemical solution, young seedlings were infected with chemically resistant and susceptible cucumber gray mold fungus (Botrytis ciner).
A cut plate (diameter 5 m) of bacterial flora of ea ) was pasted onto the leaf surface and inoculated.

After leaving it under humid conditions at 20°C for 3 days to develop the disease,
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 7, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. Ta.

Table 7 Next, examples of mixing the compound of the present invention with a benzimidazole thiophanate fungicide and a cyclic imide fungicide will be described. Table 8 shows the benzimidazole thiophanate fungicide and cyclic imide fungicide used in Test Example No.

Table 8] □Snow 1 □■ Test Example 5 Cucumber Powdery Mildew Control Effect A 90 tnl capacity plastic pot was filled with sandy loam, and cucumbers (variety: Sumo Half Day) were sown. Cultivate this at room temperature for 8 days,
Cucumber seedlings with expanded cotyledons were obtained. A water-diluted solution of the test drug in the form of an emulsion or a wettable powder was sprayed onto the foliage of the seedlings until a sufficient amount of droplets adhered to the leaf surface.

After air-drying the chemical solution, the seedlings were infected with cucumber powdery mildew fungus (5 phae).
Rotheca fuliginea) 0) A conidial suspension obtained by selling drug-resistant bacteria and susceptible bacteria was spray inoculated. The plants were placed in a greenhouse and cultivated for 10 days 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 9, any of the compounds of the present invention and flower compounds A, B, C, D, and E.

When mixed with any of F, G, or H and sprayed, a superior pest control effect was observed compared to when they were sprayed alone.

Table 9 Test Example 6 Tomato gray mold control effect 90m7! Fill a plastic pot with sandy loam,
Tomatoes (variety: Fukuju No. 2) were sown. This in a greenhouse 4
After cultivating for a week, tomatoes at the fourth power stage were obtained. Add to this a water diluted solution of the test drug in the form of an emulsion or wettable powder at 1 oz per pot.
I sprayed nd2 life and foliage. After air-drying the chemical solution, gray mold fungus (
A conidial liquid obtained by mixing drug-resistant and susceptible bacteria of Botrytis cirierea was inoculated. The specimens were left in a humid room at 20° C. for 5 days, 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, when any of the compounds of the present invention, Compounds I, J, and L were sprayed together, a superior control effect was obtained compared to when they were sprayed alone. It was done.

Table 10 0 shots clear person Hisabe Kato Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 0 shots clear person Hiroshi Noguchi Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 0 shots Atsuya Takahashi Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 0 shots: Shigeo Yamamoto Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 0 shots clear person Yukio Oguri Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 0 shots clear person Katsuzo Kamoshita Sumitomo 4-2-1 Takashi, Takarazuka City Within Kagaku Kogyo Co., Ltd. 14C.

Claims (5)

[Claims] (1) General formula [wherein X and Y are the same or different, a hydrogen atom,
represents a halogen atom, a lower alkenyl group, a lower cyanoalkenyl i, an i-class alkynyl group, a lower alkoxyl group, or a cyan group, or represents a lower alkyl group optionally substituted with a halogen atom, a hydroxyl group, or a cyan group, Or general formula -CH20R, -COOR,
-CH(OR)2. un<訃(CH2)n, COR,' CH=
Represents a substituent represented by N OR or -CONRR (where RB represents a lower alkyl group, lower alkenyl group, lower alkynyl group or lower haloalkyl group. R4 represents a hydrogen atom or a lower alkyl group.n
represents 2, 8 or 4. ). However, this excludes the case where X and Y simultaneously represent a hydrogen atom. Z represents a hydrogen atom, a fluorine atom, or a substituent represented by the general formula -OR (wherein, R5 represents a lower alkenyl group or a lower alkynyl group, or a halogen atom, a lower alkoxyl group, or a lower cycloalkyl group). represents an optionally substituted lower alkyl group). A and B are the same or different and represent an oxygen atom or a sulfur atom. R1 is a cyan group, or has the general formula -SR or -OR
represents a group represented by represents a phenyl group which may be substituted with a nitro group, an i-class alkyl group, a carboxyl group or a lower alkoxyl group, or a norogen atom, a cyano group, a lower alkoxyl group, an amino group, a lower alkylamino group or a phenoxy Lower alk(s) which may be substituted with a group(s)
17 represents a kill group or has the general formula -CR. (where M represents an oxygen atom or a sulfur atom, R represents a lower alkenyl group, a lower alkynyl group, or a hegeloamonol group, or) substituted with 10 gene atoms or a lower alkyl group; R8 represents a phenyl group which may be substituted with a phenyl group, or a lower alkyl group which may be substituted with a norogen atom, a cyano group, a lower alkoxyl group or a lower cycloalkyl group.
represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyl group. ). ). R2 represents an alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group or a lower haloalkynyl group, or a halogen atom, a cyano group, a lower alkoxyl group, a lower alkenyloxy group,
Represents a lower alkyl group which may be substituted with a lower haloalkoxyl group, phenoxy group, lower aralkyloxy group, phenyl group, or lower cycloalkyl group. An N-phenyl carbamate compound represented by (2) General formula [wherein, X and Y are the same or different, a hydrogen atom,
represents a halogen atom, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxyl group, or a cyano group, or represents a lower alkyl group optionally substituted with a halogen atom, a hydroxyl group, or a cyano group, or , general formula -CH20K, -COO
R, -CH(OR)2. Alternatively, it represents a 1d substituent represented by -CONRR (where R represents a lower alkyl group, lower alkenyl group, lower alkynyl group or lower haloalkyl group. R represents a hydrogen atom or a lower alkyl group). n represents 2°3 or 4). Except when X and Y simultaneously represent a hydrogen atom. Z represents a hydrogen atom, a fluorine atom, or a substituent represented by the general formula -OR (wherein, I represents a lower alkenyl group or a lower alkynyl group, or a halogen atom, a lower alkoxyl group, or a lower Represents a lower alkyl group that may be substituted with a cycloalkyl group.)
. R1 is a cyano group, or has the general formula -SR or -OR
represents a group represented by represents a phenyl group which may be substituted with a nitro group, a lower alkyl group, a carboxyl group or a lower alkoxyl group, or a halogen atom, a cyano group, a lower alkoxyl group, an amino group, a lower alkylamino group or a phenoxy group (here, M represents an oxygen atom or a sulfur atom, R represents a lower alkenyl group, a lower alkynyl group, or a heteroaryl group, or a halogen atom or a lower Represents a phenyl group optionally substituted with an alkyl group, or a lower alkyl group optionally substituted with a halogen atom, cyan group, lower alkoxyl group, or lower cycloalkyl group, and R is a hydrogen atom, a lower represents an alkyl group, lower alkenyl group, lower alkynyl group or lower alkoxyl group). ] Aniline derivatives represented by the general formula % [In the formula, A and B are the same or different, and each oxygen atom represents a sulfur atom. R2 represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group, or a halogen atom, a cyano group, a lower alkoxyl group, a lower alkenyloxy group, a lower haloalkoxyl group, Represents a lower alkyl group which may be substituted with a phenoxy group, a lower aralkyloxy group, a phenyl group, or a lower cycloalkyl group. [In the formula, X, Y, Z, A, B, R and R have the same meanings as above. ] A method for producing an N-phenyl carbamate compound. (3) General formula [wherein X and Y are the same or different, a hydrogen atom,
represents a halogen atom, a lower alkenyl group, a-class cyanoalkenyl group, a lower alkynyl group, a lower alkoxyl group, or a cyano group, or represents a lower alkyl group optionally substituted with a halogen atom, a hydroxyl group, or a cyano group, Or general formula -CH20R, -COOR,
-CH(OR)2. or represents a substituent represented by -C(JI', lRR (where R8 represents a lower alkyl group, lower alkenyl group, lower alkynyl group or lower haloalkyl group; R4 represents a hydrogen atom or a lower alkyl group). n represents 2°3 and 4).However, this excludes the case where X and Y both represent a hydrogen atom.Z represents a hydrogen atom, a fluorine atom, or a substituent represented by the general formula -OR (herein, A and B are the same or different; , represents an oxygen atom or a sulfur atom. R2 represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl a, aS haloalkenyl group or a lower haloalkynyl group, or a halogen atom, a cyan group, a lower alkoxyl group, a lower represents a lower alkyl group optionally substituted with an artenyloxy group, a lower haloalkoxyl group, a phenoxy group, a lower aralkyloxy group, a phenyl group, or a lower cycloalkyl group. Formula [wherein R6' represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a naphthyl group, or a halogen atom, a cyano group, a nitro group, or a lower alkyl group. represents a phenyl group which may be substituted with a group, a carboxyl group or a lower alkoxyl group, or is substituted with a halogen atom, a cyano group, a lower alkoxyl group, an amino group, a lower alkylamino group, or a fluorine or nitrogen group. or a group having the general formula -CR7, where M represents an oxygen atom or a sulfur M atom, and R represents a lower alkenyl group, a lower alkynyl group, or a heteroaryl group; or represents a phenyl group which may be substituted with a halogen atom or a lower alkyl group, or represents a lower alkyl group which may be substituted with a halogen atom, cyan group, lower alkoxynyl group or lower cycloalkyl group ,R
represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyl group. ),
W represents a halogen atom. N-phenyl represented by the general formula [wherein X, Y, Z, A, B, R2 and R'' have the same meanings as above.'' Method for producing carbamate compounds. (4) General formula [wherein, X and Y are the same or different, a hydrogen atom,
Does it represent a halogen atom, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxyl group, or a cyano group, or a lower alkyl group optionally substituted with a halogen atom, a hydroxyl group, or a cyano group , or general formula -CH20R, -COOR
, -CH(OR)2. Alternatively, it represents a substituent represented by -CONRR (where R represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group. R represents a hydrogen atom or a lower alkyl group. n is 2゜represents 3 or 4). However, this excludes the case where X and Y simultaneously represent a hydrogen atom. Z represents a hydrogen atom, a fluorine atom, or a substituent represented by the general formula -OR (where R represents a lower alkenyl group or a lower alkynyl group, or a halogen atom, a lower alkoxyl group, or a lower cycloalkyl group) represents an optionally substituted lower alkyl group). A and B are the same or different and represent an oxygen atom or a sulfur atom. R represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, or a lower haloalkynyl group, or a halogen atom, a cyano group, a lower alkoxyl group, a lower alkenyloxy group, a lower haloalkoxyl group, Represents a lower alkyl group which may be substituted with a phenoxy group, a lower aralkyloxy group, a phenyl group, or a lower cycloalkyl group. ] and the general formula [wherein R represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a naphthyl group, or Represents an ifhenyl group which may be substituted with a halogen atom, cyano group, nitro group, lower alkyl group, carboxyl group or lower alkoxyl group, or a halogen atom, cyano group, lower alkoxyl group, amine group, lower alkylamino represents a lower alkyl group 17 which may be substituted with a group or a phenoxy group, or has the general formula -CR. Here, M represents an oxygen atom or a sulfur atom, and R represents a lower alkenyl group, a lower alkynyl group, or a heteroaryl group, or may be substituted with a halogen atom or a lower alkyl group. represents a phenyl group, or represents a lower alkyl group optionally substituted with a halogen atom, a cyano group, a lower alkoxyl group, or a lower cycloalkyl group, R8 is a ru group,
Represents a lower alkynyl group or a lower alkoxyl group. ), W represents a halogen atom. ] N-phenyl carbamate represented by the general formula "wherein X, Y, Z, A, B, R and R have the same meanings as above." Method for producing system compounds. (5) General formula [wherein, X and Y are the same or different, a hydrogen atom,
represents a halogen atom, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxyl group or a cyan group, or a lower alkyl group which may be substituted with a halogen atom, a hydroxyl group or a cyan group, or , general formula -CH20R8, -COOR
', CB(OR8)2. -CHRZ>(CH2)n, -〇〇R2-CH=N-O
R4 or -c (JNR8R' represents a substituent (here, R represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group. R represents a hydrogen atom or a lower alkyl group.n is 2
゜Represents 3 or 4. ). However, this excludes the case where X and Y simultaneously represent a hydrogen atom. Z represents a hydrogen atom, a fluorine atom, a group of the general formula, or a lower alkyl group optionally substituted with a halogen atom, a lower alkoxyl group, or a lower cycloalkyl group. ). A and B are the same or different and represent an oxygen atom or a sulfur atom. R1 is a cyano group, or has the general formula -5R6 or -O
Represents a group represented by R (where R represents a hydrogen atom, a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a naphthyl group, or a halogen atom, It represents a phenyl group which may be substituted with a cyano group, a nitro group, a lower alkyl group, a carboxyl group or a lower alkoxyl group, or a halogen atom, a cyano group,
Represents a lower alkoxy group, an amino group, a lower alkylamino group, or a lower alkyl group optionally substituted with a phenoxy group (where M represents an oxygen atom or a sulfur atom, and R represents a lower alkenyl group, a lower alkynyl group) Yes
This represents a heteroaryl group, or represents a phenyl group optionally substituted with a halogen atom or a lower alkyl group, or) A represents a halogen atom, a cyano group, a lower alkoxyl group, or a lower cycloalkyl group. Indicates an optionally substituted lower alkyl group R8
represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower alkoxyl group. ). ). R2 represents a lower alkenyl group, a lower alkynyl group, a lower cycloalkyl group, a lower noroalkenyl group, or a lower haloalkynyl group, or a halogen atom, a cyano group, a lower alkoxyl group, a lower alkenyloxy group,
Represents a lower alkyl group which may be substituted with a lower haloalkoxyl group, phenoxy group, lower aralkyloxy group, phenyl group, or lower cycloalkyl group. ] An agricultural and horticultural fungicide characterized by containing the following N-phenyl carbamate compound as an active ingredient.