JPH0465061B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [In the formula, X and Y are the same or different, and are any of a halogen atom, a lower alkyl group, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxy group, a cyano group, or a halogen atom, a hydroxyl group, or At least one of the cyano groups
lower alkyl group substituted with 1 atoms or substituents, or a substituent represented by the following general formula; _-CH2
OR3 ,

【formula】

【formula】

【formula】

[Formula]-CH=N- OR ₆ ,

[Formula] (However, R ₆ represents a lower alkyl group, lower alkenyl group, lower alkynyl group, or lower haloalkyl group. _{R 4} and R ₅ are the same or different and represent a lower alkyl group. n is 2, 3, or Indicates an integer of 4.
R ₆ represents a hydrogen atom or a lower alkyl group. ) is shown. Z represents an oxygen atom or a sulfur atom. R ₁
represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with at least one atom or substituent among a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. . R ₂ is a C ₁ to C ₃ alkyl group,
_C3 - _C8 alkenyl group, _C3 - _C8 alkynyl group,
lower cycloalkyl group, lower haloalkenyl group,
a lower haloalkynyl group, or at least one atom of a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group, a lower cycloalkyl group, or Indicates a lower alkyl group substituted with a substituent. However, X
and when Y is a bromine atom, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not a propargyl group, and X and Y are methoxy groups at the same time.
When R ₁ is a methyl group and Z is an oxygen atom,
When R ₂ is not an ethyl group, X and Y are both ethoxy groups, R ₁ is an ethyl group, and Z is an oxygen atom, R ₂ is not an ethyl group, X and Y are halogen atoms, and R ₁ is an ethyl group. It is a lower alkyl group which may be substituted with a halogen atom, and when Z is a sulfur atom, R ₂ is neither a methyl group nor an ethyl group, and X and Y are a halogen atom, a lower alkyl group, or a lower alkoxy group. When R ₁ is a lower alkyl group and Z is an oxygen atom, R ₂ has the general formula -W-C≡C-R ₇ (wherein, W represents an alkylene group and R ₇ represents an alkyl group). ) There are no substituents. ] It is indicated by. An agricultural and horticultural fungicide characterized by an N-phenyl carbamate compound, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient. In the general formula [], X and Y are preferably a fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, n-butyl group,
vinyl group, 1-propenyl group, 2-propenyl group, ethynyl group, methoxy group, ethoxy group, cyano group, 1,2-dibromoethyl group, hydroxymethyl group, cyanomethyl group, 2-cyanoethyl group,
2-cyanovinyl group, methoxymethyl group, ethoxymethyl group, allyloxymethyl group, propargyloxymethyl group, 2-fluoroethoxymethyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, 2-fluoroethoxycarbonyl group, Propargyloxycarbonyl group, dimethoxymethyl group, diethoxymethyl group, ethylenedioxymethyl group, formyl group,
Acetyl group, hydroxyiminomethyl group, methoxyiminomethyl group, carbamoyl group, N-methylcarbamoyl group, particularly preferably X and Y are chlorine atom, bromine atom, methyl group, ethyl group, n-propyl group, methoxymethyl group Yes, when X is a methoxy group, ethoxy group, or methoxymethyl group, Y is a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, a methoxy group, an ethoxy group,
Examples include cyano group, methoxymethyl group, methoxycarbonyl group, dimethoxymethyl group, and acetyl group. Further, Z preferably represents an oxygen atom.
R ₁ is preferably a methyl group, an ethyl group, an allyl group,
Examples include propargyl group, difluoromethyl group, and 2-chloroethyl group. R ₂ is preferably a methyl group, ethyl group, isopropyl group, sec-butyl group, allyl group, 1-ethylpropyl group, 1-
Methylbutyl group, 1-methylpentyl group, 1-methylheptyl group, 1-methyl-2-propenyl group, propargyl group, 2-butenyl group, 1-methyl-3-butenyl group, 1-pentyl-2-propenyl group, 1-methyl-2-propynyl group, 1-ethyl-2-propynyl group, 2-butynyl group, 3-
Butynyl group, 1-methyl-3-butynyl group, 1-
Butyl-2-propynyl group, 1-pentyl-2-
Propynyl group, cyclobutyl group, 2-cyanoethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2,2-trifluoroethyl group, 1-fluoromethyl-2-fluoroethyl group, 1 -chloromethylethyl group, 1-bromomethylpropyl group, 1-methoxymethyl-2
-chloroethyl group, 4-chloro-2-butenyl group, 4-chloro-2-butynyl group, 1-cyclopropylethyl group, 1-cyclopentylethyl group,
2-methoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-allyloxyethyl group, 2-(2-chloroethoxy)ethyl group, 2-benzyloxyethyl group, 1-methyl- 2-methoxyethyl group, 1-methyl-2-n
Examples include -butoxyethyl group, 1-methyl-2-n-butoxyethyl group, and 1-methyl-2-phenoxyethyl group. The present inventors previously described the general formula [A] [In the formula, Y is the same or different and represents a lower alkyl group, a lower alkoxy group, or a halogen atom. R represents a methyl group or an ethyl group. However, Y does not have a chlorine atom or a bromine atom at the same time. ] 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 such as the N-phenyl carbamate compounds shown below (hereinafter referred to as drug-resistant bacteria) It has been found that it has a selectively strong bactericidal effect against. After further investigation, it was discovered that the N-phenyl carbamate compound represented by the above general formula [] is also effective against drug-resistant bacteria, and the present invention was completed. The N-phenyl carbamate compounds represented by the general formula [] are benomyl [methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate], fuberidazole [2-(2-furyl)benzimidazole], and thiabendazole [2-ylcarbamate]. -(4-thiazolyl)benzimidazole],
Carbendazim [methyl benzimidazole-
2-ylcarbamate], thiophanate methyl [1,2-bis(3-methoxycarbonyl-2
-thioureido)benzene], thiophanate [1,2-bis(3-ethoxycarbonyl-2-
benzimidazole/thiophanate fungicides such as N-(3',
5'-Dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 3-
(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazoline-2,4-dione, 3
-(3',5'-dichlorophenyl)-5-methyl-5
-vinyloxazolidine-2,4-dione, ethyl (RS)-3-(3',5'-dichlorophenyl)-5
-Methyl-2,4-dioxoxazolidine-5
-It is characterized by a strong selective bactericidal effect against drug-resistant bacteria that are resistant to cyclic imide fungicides such as carboxylates. The aforementioned benzimidazole thiophanate fungicides exhibit excellent control effects against various pathogenic bacteria that parasitize agricultural and horticultural crops, and have been widely used as agricultural and horticultural fungicides since around 1970, greatly contributing to increased crop production. . However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria spread, reducing the control effectiveness of the fungicides, often making them practically unusable. If the spraying of fungicides does not have the expected control effect and the outbreak of disease cannot be suppressed, the damage to farmers and other fungicide users is enormous. Furthermore, it is known that bacteria that are resistant to any of the benzimidazole/thiophanate fungicides are also resistant to other fungicides in this group, exhibiting so-called cross-resistance. Therefore, in a field where no pest control effect is observed even when spraying Benomyl, no control effect can be expected even if other benzimidazole/thiophanate fungicides are sprayed. In fields where drug-resistant bacteria are prevalent, the use of benzimidazole/thiophanate fungicides must be discontinued, but there are many known cases in which the density of drug-resistant bacteria does not decrease even after discontinuing their use. If resistant bacteria emerge, the effects will be felt for a long time. In addition, in such fields, target diseases are controlled by spraying fungicides of other systems to which drug-resistant bacteria do not show cross-resistance, but benzimidazole-thiophanate fungicides are more effective at controlling diseases. There are very few that are effective, making appropriate control difficult. Cyclic imida fungicides are used to treat gray mold on various crops.
It is widely used as a fungicide for agricultural and horticultural purposes due to its excellent effectiveness in controlling sclerotinia, sclerotium, etc., and greatly contributes to increased crop production. recent years,
Due to soaring oil prices, greenhouse horticulture and other greenhouse horticulture have had to cut back on oil consumption for heating, and as a result, gray mold, which is active at low temperatures, has become a serious problem. Under these circumstances, cyclic imide fungicides, which are effective drugs for controlling gray mold, play an important role. Furthermore, there is no known practical fungicide that is sufficiently effective in controlling gray mold to replace this type of fungicide. However, it is generally said that if the same type of fungicide is used continuously, bacteria that become resistant to the fungicide will develop, reducing the disease control effect of the fungicide, and the case of cyclic imide fungicides is no exception. has become clear. That is, if any of the above-mentioned cyclic imide fungicides is continuously applied to crops for the purpose of controlling botrytis, botrytis fungi that are resistant to any of the cyclic imide fungicides will develop, reducing the control effect. Examples of this are becoming recognized. Considering the above circumstances, the present inventors believe that if there is a fungicide that selectively shows a bactericidal effect against drug-resistant bacteria, it can be expected to have a high disease control effect in fields where drug-resistant bacteria occur. We worked hard to develop a drug. As a result, it was found that the above-mentioned N-phenyl carbamate compound is a bactericidal agent that exhibits a strong bactericidal effect selectively against drug-resistant bacteria. That is, as is clear from the test examples described below, the compounds of the present invention are effective against diseases caused by wild fungi that are susceptible to benzimidazole/thiophanate fungicides or wild fungi that are sensitive to cyclic imide fungicides (hereinafter referred to as drug-susceptible bacteria). However, it showed an excellent control effect against diseases caused by drug-resistant bacteria, and the bactericidal activity of the compounds of the present invention against drug-resistant bacteria was extremely selective. The herbicide Barban [4-chloro-2-butynyl N-(3
-chlorophenyl) carbamate], chlorbufam [1-methyl-2-propynyl N-(3-chlorophenyl) carbamate], chlorprofam [isopropyl N-(3-chlorophenyl) carbamate], and profum [isopropyl N-phenyl carbamate]. It has already been reported that it exhibits selective bactericidal activity (CRAcad, Sc.
Daris, t.289, S'erie D pp. 691-693, 1979
However, as is clear from the test examples described later, the compound of the present invention shows a far superior control effect against benzimidazole/thiophanate fungicide-resistant bacteria compared to these herbicides, and It exhibits an excellent control effect against fungicide-resistant bacteria and has almost no phytotoxic effects on agricultural and horticultural crops, making it of high practical value. On the other hand, as is clear from their properties as herbicides, the above-mentioned herbicides have a strong phytotoxic effect on agricultural and horticultural crops when sprayed on foliage, and their bactericidal effects against benzimidazole/thiophanate fungicide-resistant bacteria are not practical. It's not as strong as it gets. As mentioned above, the compound of the present invention exhibits a strong bactericidal effect selectively against bacteria that are resistant to benzimidazole/thiophanate fungicides or cyclic imide fungicides, and therefore, the use of the above-mentioned fungicides can prevent the appearance of bacteria. It can be used to control expected or emerging drug-resistant bacteria. For example, apple powdery mildew (Podosphaera
leucotricha), Venturia
inaequalis), black spot fungus (Mycosphaerella
pomi), Marssorina mali, Sclerotinia mali, Phyllactinia kakicola, Gloeosporium kaki, Sclerotinia cinerea, Cladosporium carpophilum), Phomopsis sp., Botrytis cinerea, Cercospora
viticola), powdery mildew (Uncinula necator),
Elsinoe ampelina, late rot fungus (Glomerella cingulata), sugar beet brown spot fungus (Cercospora beticola), peanut brown spot fungus (Cercospora arachidicola), black bitter fungus (Cercospora personata), barley powdery mildew fungus ( Erysiphe graminis f.sp.hordei), I.
Spot disease fungus (Cercosporella)
herpotrichoides), Fusarium
nivale), wheat powdery mildew (Erysiphe
graminis f.sp. tritici), Sphaerotheca fuliginea, Mycosphaerella melohis, Sclerotinia sclerotiorum, Botrytis cinerea, Cladosporium
cucumerinum), tomato leaf mold (Cladosporium fulvum), gray mold (Botrytis cinerea), eggplant black blight (Coryhespora melongenae), strawberry powdery mildew (Sphaerotheca humuli), yellow chlorosis fungus (Fusarium oxysporum f.sp. fragariae), Botrytis alli on onions, Sclerotinia sclerotiorum on lettuce, Cercospora apii on celery, Phaeoisariopsis griseola on kidney beans, Botrytis cinerea on hops ), drug-resistant bacteria such as Erysiphe cichoracearum on tobacco, Diplocarpon rosae on roses, Elsinoe fawcetti on mandarin oranges, Penicillium italicum, and Penicillium digitatum. It can be used to control. In actual fields, when drug-resistant and sensitive bacteria coexist, benzimidazole
One or more types of thiophanate methyl-based fungicides or cyclic imide-based fungicides, and the compound of the present invention []
By mixing and using one or more types of N-phenyl carbamate compounds shown in the following, it is possible to control both drug-resistant bacteria and sensitive bacteria at the same time. As a result of further studies on the bactericidal activity of the N-phenyl carbamate compound represented by the general formula [], it was found that it is effective in controlling certain diseases regardless of the presence or absence of drug resistance. The compound of the present invention can be used, for example, in rice blast fungi (Pyricularia
oryzae), downy mildew of cucumbers (Pseudoperonospora cubensis), downy mildew of grapes (Plasmopara viticola), and Phytophthora infestans of potatoes. On the other hand, it has also become clear that the compound of the present invention has high safety for humans, livestock, and fish, and can be used without causing any harm to agriculturally useful crops. The compound of the present invention represented by the general formula [] is ethyl N-[(3,4,5-trimethoxy)phenyl]
All compounds are new except for three: carbamate, ethyl N-[(3,4,5-triethoxy)phenyl]carbamate, and propargyl N-[(3,5-dibromo-4-methoxy)phenyl]carbamate. These three compounds are respectively Arch.
Pharm., 272 , 221-235 (1934) French Patent
Although described in M8200 DT−OS 2041986,
It is not described that it has bactericidal activity or is useful as a bactericidal agent. The compound of the present invention [] can be produced by the following method. (a) General formula [] [In the formula, X, Y and R ₁ have the same meanings as above. ] Aniline derivatives shown by the general formula [ ] [In the formula, R ₂ and Z have the same meanings as above. ] A manufacturing method of reacting a chloroformic acid ester or a chloroformic acid thioester shown in the following. This reaction involves benzene, toluene, xylene, diethyl ether, tetrahydrofuran,
carried out in an organic solvent such as dioxane, chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethylformamide or a mixture thereof;
By using a dehydrochlorination agent such as pyridine, triethylamine, diethylaniline, sodium hydroxide, potassium hydroxide, etc., the reaction can be carried out in high yield. The reaction can be carried out by cooling or heating (0 to 150°C) as necessary.
The process can be completed instantly to 10 hours, and the desired product can be obtained in good yield. The aniline derivative represented by the general formula [] in production method (a) is the general formula [] [In the formula, X, Y and R ₁ have the same meanings as above. ] Obtained by the reduction reaction of the nitrobenzene derivative shown below. This nitrobenzene derivative has the general formula [] [In the formula, X and Y are as described above. ] A nitrophenol derivative represented by the general formula [] R ₁ A [] [wherein A represents a leaving group]. R ₁ is as described above. ] It can be obtained by reacting with the alcohol derivative or halide shown below. The leaving group represented by A here generally refers to a tosyloxy group,
Indicates a mesyloxy group or a halogen atom. The nitrophenol derivative represented by the general formula [] can be easily obtained, for example, by the method described in the literature JOG 1962, 27 , 218-226. The condensation reaction between the nitrophenol derivative represented by the general formula [] and the alcohol derivative or halide represented by the general formula [] is performed with benzene,
Toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform,
The reaction is carried out in an organic solvent such as carbon tetrachloride, ethyl acetate, ethanol, isopropanol, dimethyl formaldehyde, water, or a mixture thereof. pyridine, triethylamine,
By using a dehydrohalogenating agent such as caustic soda, caustic potash, or sodium carbonate, the reaction can be carried out in high yield. The reaction can be completed in 0.5 to 10 hours by heating or cooling as necessary, and the desired product can be obtained in good yield. Reduction reactions that lead the nitrobenzene derivative represented by the general formula [] to the aniline derivative represented by the general formula [] include catalytic reduction using catalysts such as platinum oxide, Raney nickel, platinum black, palladium on carbon, tin, iron, zinc, etc. Reduction of metals such as with acids such as hydrochloric acid and sulfuric acid, sodium, lithium, aluminum, magnesium,
Reduction with metals such as zinc in alcoholic solutions, reduction with sodium, zinc and alkali hydroxides or alcoholic alkalis, stannous chloride, ferrous sulfate, ferrous hydroxide, sodium sulfide, polysulfides. Examples include reduction using inorganic compounds such as sodium, ammonium sulfide, and hydrogen sulfide, and reduction using hydrazine compounds such as hydrazine and phenylhydrazine. For example, in the case of catalytic reduction using palladium on carbon, the reaction is hydrogenation in an organic solvent such as benzene, toluene, ethanol, methanol, isopropanol, tetrahydrofuran, dioxane, or a mixed solvent thereof under normal pressure or pressure. It is carried out by. The reaction is completed in 30 minutes to 10 hours, and the desired product can be obtained in good yield. (b) General formula [] [In the formula, X, Y and R ₁ have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula R ₂ ZH [wherein R ₂ and Z have the same meanings as above. ] A manufacturing method of reacting alcohols or thioalcohols shown in This reaction is carried out without a solvent or in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, carbon tetrachloride, etc. without a catalyst or with triethylamine,
This can be carried out using N,N-diethylaniline or 1,4-diazabicyclo-(2,2,2)octane as a catalyst. The reaction is cooled or heated as necessary (0 to 50
°C), the process can be completed instantly to 10 hours and the desired product can be obtained in good yield. The phenyl isocyanate derivative represented by the general formula [] can be obtained by reacting the aniline derivative represented by the general formula [] with phosgene. This reaction involves benzene, toluene, xylene,
It is carried out in an organic solvent such as ethyl acetate or a mixture thereof. By heating from 50° C. to reflux temperature as necessary, the reaction can be completed instantly or in 10 hours, and the desired product can be obtained in good yield. (c) General formula [] [In the formula, X, R ₁ , R ₂ and Z have the same meanings as above. ] Benzaldehyde represented by the general formula [ ] is reacted with hydroxylamine or lower alkoxyamine. [In the formula, X, R ₁ , R ₂ and Z have the same meanings as above. Y ₁ represents a hydroxyiminomethyl group or a lower alkoxyiminomethyl group. ] A method for producing an N-phenyl carbamate compound represented by: In the reaction, benzaldehyde represented by the general formula [] is dissolved in an inert solvent, and a solution of an equivalent or excess amount of hydroxylamine or lower alkoxyamine in an inert solvent is added thereto. The reaction is completed in 30 minutes to 12 hours. The inert solvent here is preferably methanol or ethanol. Next, examples of the compounds of the present invention represented by the general formula [] are as follows, but the compounds of the present invention are not limited to these. Note that the compound numbers shown here are commonly used in the following formulation examples and test examples.

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

[Table] Next, the present invention will be explained in more detail with reference to Examples. Example 1 Synthesis of isopropyl N-[(3-methoxy-4-ethoxy-5-chloro)phenyl]carbamate (according to method (a)) (3-methoxy-4-ethoxy-5-chloro)
2.0 g of aniline and N,N-diethylaniline
1.5 g was dissolved in 20 ml of toluene, and 1.2 g of isopropyl chloroformate was added dropwise over 5 minutes under ice cooling. After being left at room temperature for 12 hours, it was poured into ice water and extracted with toluene. The solvent was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid material was purified by recrystallization with toluene to obtain 1.9 g of white crystals of isopropyl N-[(3-methoxy-4-ethoxy-5-chloro)phenyl]carbamate.
I got it. (Yield 66.5%) Melting point 121-122℃ Elemental analysis value N (%) C (%) H (%) Cl (%) Calculated value 4.86 54.11 6.29 12.29 (as C ₁₈ H ₁₈ NO ₄ Cl) Actual value 4.89 54.51 6.28 12.21 Example 2 Isopropyl N-[(3,4-diethoxy)-5
-Methyl)phenyl]carbamate (according to method (b)) (3,4-diethoxy-5-methyl)aniline
2.0g was dissolved in 20ml of toluene and added dropwise to a toluene solution containing 10g of phosgene at 10-20°C. Heat slowly and reflux for 30 minutes. The temperature was returned to room temperature, and the solvent was distilled off under reduced pressure to obtain 2.2 g of 3,4-diethoxy-5-methylphenyl isocyanate. This was added without purification to 20 ml of isopropanol containing 1 g of triethylamine. After being left at room temperature for 12 hours, it was poured into ice water and extracted with toluene. The solvent was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting solid material was
Purified by recrystallization with toluene, isopropyl N
-2.5 g of [(3,4-diethoxy-5-methyl)phenyl]carbamate was obtained. (Yield: 88% from 3,4 diethoxy-5-methylaniline). Melting point 86-87.5℃ Elemental analysis N (%) C (%) H (%) Calculated value 4.98 64.03 8.24 (as C ₁₅ H ₂₃ NO ₄ ) Actual value 4.95 63.87 8.52 Example 3 Isopropyl N [(3,4- Synthesis of diethoxy-5-methoxyiminomethyl)phenyl]carbamate (according to method (c)) Isopropyl N-[(3,4-diethoxy-5-
0.6 g of formyl) phenyl] carbamate was dissolved in 20 ml of methanol. sodium hydroxide here
A solution of 0.32 g of methoxyamine hydrochloride and 0.66 g of methoxyamine hydrochloride dissolved in 10 ml of water was added. The mixture was stirred at room temperature for 12 hours, and then the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and dried over magnesium sulfate. After filtration, the filtrate is concentrated, the obtained solid is washed with hexane, and isopropyl N-
0.61 g of [(3,4-diethoxy-5-methoxyiminomethyl)phenyl]carbamate was obtained. (Yield 93%) Melting point 110-111.5°C Elemental analysis value C (%) H (%) N (%) Calculated value 59.24 7.46 8.64 (as C ₁₆ H ₂₄ N ₂ O ₅ ) Actual value 59.01 7.56 8.34 Compound of the present invention Alternatively, when actually applying the fungicidal composition of the present invention, it can be used in pure form without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. It can be used in any form such as powder, wettable powder, oil, emulsion, tablet, granule, fine granule, aerosol, and flowable. The formulations generally contain from 1.0 to 95.0% by weight of active compound (including mixed ingredients), preferably
Contains 2.0-80.0%, usually 2-100 per 10 ares
An application amount of 1.5 g is appropriate. Furthermore, the concentration used is
A range of 0.005% to 0.5% is desirable, but since the amount and concentration used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., it is not possible to increase or decrease without being limited to the above range. There is no problem. Furthermore, it can be used in admixture with other fungicides, herbicides, plant growth regulators and insecticides, such as S-normal-butyl S-para-tertiary-butylbenzyldithiocarbonimidate,
0,0-dimethyl O-(2,6-dichloro-4-
methylphenyl) phosphorothioate, N-trichloromethylthio-4-cyclohexene-1,2
-dicarboximide, cis-N-(1,1,2,
2-tetrachloroethylthio)-4-cyclohexene-1,2-dicarboximide, polyoxin, streptomycin, zinc ethylene bisdithiocarbamate, zinc dimethylthiocarbamate, manganese ethylene bisdithiocarbamate, bis(N,N-dimethylthiocarbamoyl) Disulfide, tetrachloroisophthalonitrile, 8-hydroxyquinoline, dodecylguanidine acetate, 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide, N'-dichlorofluoromethylthio-N,N
-dimethyl-N'-phenylsulfamide, 1-
(4-chlorophenoxy)-3,3-dimethyl-1
-(1,2,4-triazol-1-yl)-2-
Butanone, methyl N-(2,6-dimethylphenyl)-N-methoxyacetyl-2-methylglycinate, disinfectants such as aluminum ethyl phosphite, 2,4-dichlorophenoxyacetic acid, 2-methyl-4 -Chlorphenoxybutyric acid, 2-methyl-
Phenoxy herbicides such as 4-chlorophenoxyacetic acid (including esters and salts), 2,4-dichlorophenyl 4'-nitrophenyl ether, 2,4,
6-Trichlorophenyl 4'-nitrophenyl ether, 2-chloro-4-trifluoromethylphenyl 3'-ethoxy-4'-nitrophenyl ether, 2,4-dichlorophenyl 4'-nitro-3 ′−
Diphenyl ether herbicides such as methoxyphenyl ether, 2,4-dichlorophenyl 3'-methoxycarbonyl-4'-nitrophenyl ether,
2-chloro-4,6-bisethylamino-1,
3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-methylthio-4,6-bisethylamino-1,3,5-triazine, 2- Methylthio-4,6-bisisopropylamino-1,3,
5- Triazine herbicides such as triazine, 3-
(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1-
Methoxy-1-methylurea, 1-(α,α-dimethylbenzyl)-3-p-tolylurea, 1-
Urea herbicides such as (2-benzothiazolyl)-1,3-dimethylurea, isopropyl N-(3-chlorophenyl) carbamate, methyl N-(3,
Carbamate herbicides such as 4-dichlorophenyl)carbamate, S-(4-chlorobenzyl)N,
Thiol carbamate herbicides such as N-diethylthiol carbamate, S-ethyl N,N-hexamethylenethiol carbamate, 3,4-dichloropropionanilide, 2-chloro-N-methoxymethyl-2',6'-diethyl acetanilide,
2-chloro-2',6'-diethyl-N-(butoxymethyl)-acetanilide, 2-chloro-2',
6'-diethyl-N-(n-propoxyethyl)acetanilide, N-chloroacetyl-N-(2,
Acid anilide herbicides such as 6-diethylphenyl) glycine ethyl ester, uracil herbicides such as 5-bromo-3-secondary-butyl-6-methyluracil, 3-cyclohexyl-5,6-trimethyleneuracil, 1,1'-dimethyl-4,4'-
Pyridinium salt herbicides such as bipyridinium chloride, N-(phosphonomethyl)glycine, N,
N-bis(phosphonomethyl)glycine, O-ethyl O-(2-nitro-5-methylphenyl)N-
secondary butyl phosphoramidothioate,
S-(2-methyl-1-piperidylcarbonylmethyl)0,0-di-n-propyldithiophosphate, S-(2-methyl-1-piperidylcarbonylmethyl)0,0-diphenyl or di-n-
Phosphorous herbicides such as propyl dithiophosphate,
α,α,α-trifluoro-2,6-dinitro-
Toluidine herbicides such as N,N-dipropyl-p-toluidine, 5-tert-butyl-3-
(2,4-dichloro-5-isopropoxyphenyl), 1,3,4-oxadiazolin-2-one,
3-isopropyl-(1H)-2,1,3-benzothiadiazin-(3H)-one-2,2-dioxide, α-(β-naphthoxy)propionanilide, 4-(2,4-dichloro benzoyl)-1,3
-dimethylpyrazol-5-yl p-toluenesulfonate, 3-(methoxycarbonylamino)
Phenyl 3-methylphenyl carbamate, 4-
Amino-3-methyl-6-phenyl-1,2,4
-triazine, 0,0-dimethyl O-(4-nitro-3-methylphenyl) phosphorothioate,
0-(4-cyanophenyl)0,0-dimethylphosphorothioate, 0-(4-cyanophenyl)
0-ethylphenylphosphonothioate, 0,0
-dimethyl S-(N-methylcarbamoylmethyl)
Phosphorodithioate, 2-methoxy-4H-1,
Organophosphorus insecticides such as 3,2-benzodioxaphosphorine-2-sulfide, 0,0-dimethyl S-(1-ethoxycarbonyl-1-phenylmethyl)phosphorodithioate, α-cyano-3-phenyl Enoxybenzyl 2-(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-
Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate, α-cyano-3-
Phenoxybenzyl 2,2-dimethyl-3-(2,
It can be used in combination with pyrethroid insecticides such as 2-dibromovinyl)cyclopropanecarboxylate, and neither of them will reduce the control effect of each agent alone, and furthermore, a synergistic effect is expected by mixing. It is. Next, test examples and formulation examples will be given to further clarify the usefulness of the compounds of the present invention as agricultural and horticultural fungicides. Commercially available fungicides and control compounds used in the following Test Examples 1 to 9 are shown in Table 2.

【table】

【table】

【table】

[Table] Test Example 1 Powdery mildew control effect on cucumber A 90 ml plastic pot was filled with sandy loam, and cucumber (variety: Sagami Hanshiro) was sown. This was cultivated at room temperature for 8 days to obtain 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 the chemical solution was air-dried, the seedlings were spray-inoculated with a conidial suspension of a chemical-resistant or sensitive cucumber powdery mildew fungus (Pphaerotheca fuliginea). 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 severity was calculated by the following method. That is, depending on the appearance of lesions on the investigated leaves, 0, 0.5, 1,
The disease was classified into indexes 2 and 4, and the severity of the disease was calculated using the following formula. (Infection index) (Infection status) 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 less than 50% of the leaf area. 4...Bacterial flora or lesions are observed on the leaf surface over 50% of the leaf area. Disease severity (%) = Σ {(Sickness index) x (Number of leaves)} / (Number of inspected leaves) x 4
×100 Next, the control value was calculated using the following formula. Control value = 100 - (incidence in compound-treated area) / (incidence in non-treated area) x 100 As a result, as shown in Table 3, the compound of the present invention has an excellent control effect when inoculated with drug-resistant bacteria. show,
When inoculated with drug-susceptible bacteria, no control effect was shown. On the other hand, none of the commercially available fungicides, benomyl, thiophanate methyl, and carbendazim, showed any control effect when inoculated with drug-resistant bacteria, but showed excellent control effects when inoculated with drug-susceptible bacteria. Compounds with similar chemical structures and commercially available herbicides with similar chemical structures used for comparison showed almost no control effect when inoculated with any of the bacteria.

【table】

【table】

【table】

[Table] Test Example 2 Sugar beet brown spot control effect Fill a 90ml plastic pot with sandy loam and add 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 wettable powder until the droplets fully adhered to the leaf surface. After the chemical solution was air-dried, the seedlings were spray inoculated with a conidial suspension of chemically resistant or susceptible Cercospora beticola. After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, 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 4, similar to the results of Test Example 1, the compound of the present invention exhibited an excellent control effect when inoculated with drug-resistant bacteria; Jim showed excellent control effects when inoculated with drug-susceptible bacteria. Compounds with similar chemical structures and commercially available herbicides with similar chemical structures used for comparison showed almost no control effect when inoculated with any of the bacteria.

【table】

【table】

【table】

【table】

[Table] Test Example 3 Pear scab control effect A 90 ml plastic pot was filled with a mixed soil of peat moss and sandy loam, and seeds collected from pear fruit (variety: Chojuro) were sown. 20 minutes of this in a greenhouse
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 grown for one day until the droplets sufficiently adhered to the leaf surface. After air-drying the chemical solution, the seedlings were spray inoculated with a conidial suspension of Venturia nashicola, which is either resistant or susceptible to the drug. 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 5, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-sensitive bacteria. It was shown to be effective.

【table】

【table】

[Table] Test Example 4 Peanut brown spot control effect A 100 ml plastic pot was filled with sandy loam soil, and peanuts (variety: Chiba semi-erect) were sown. After 14 days of cultivation in a greenhouse, the resulting seedlings were sprayed with 10 ml of a water diluted solution of the test compound in the form of an emulsion or wettable powder per pot. After the chemical solution was air-dried, the seedlings were spray-inoculated with a spore suspension of chemically resistant or susceptible peanut brown spot fungus (Cercospora arachidicola). After cultivating it in a greenhouse for 10 days under humid conditions by covering it with a vinyl cover, 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 6, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria;
On the other hand, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria.

【table】

[Table] Test Example 5 Control effect on gray mold disease of cucumber A 90 ml plastic pot was filled with sandy loam, and cucumber (variety: Sagami Hanshiro) 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 ml per pot and sprayed on the foliage. After air-drying the chemical solution, young seedlings are infected with chemical-resistant or sensitive cucumber gray mold fungus (Botrytis).
cinerea) was pasted on the leaf surface and inoculated. This was left under humid conditions at 20°C for 3 days to develop the disease, and then 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 7, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria;
On the other hand, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria.

【table】

【table】

【table】

【table】

【table】

【table】

【table】

【table】

[Table] Test Example 6 Effect on controlling cucumber vine blight A 90 ml plastic pot 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 10 ml per pot and sprayed on the foliage. After air-drying the chemical solution, seedlings are infected with drug-resistant or susceptible cucumber vine blight fungus (Mycosphaerella
melonis) (5 mm in diameter) was pasted onto the leaf surface and inoculated. This was left under humid conditions at 25°C for 4 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 8, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria;
On the other hand, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria.

【table】

【table】

[Table] Test Example 7 Citrus blue mold control effect Citrus fruit (variety: Unshu) was thoroughly washed with water, air-dried, and then immersed for 1 minute in an emulsion of the compound of the present invention or a control commercially available chemical solution diluted with water to a predetermined concentration. did. After air-drying, conidia of drug-resistant or sensitive citrus blue mold fungus (Penicillium italicum) were suspended in water and sprayed onto the fruit surface. After being kept in a moist room for 14 days after inoculation, the degree of disease onset was investigated using a disease index of 0, 1, 2, 3, 4, and 5 as shown below. (Disease status) (Infection index) No lesions are observed 0 Lesions are observed on less than 20% of the fruit surface area 1 Lesions are observed on less than 20-40% 2 40-60% 3 60 ~80% 〃 4 〃 Lesions are observed in 80% or more 5 The disease severity and control value were calculated in the same manner as in Test Example 1. As a result, as shown in Table 9, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria;
On the contrary, the commercial fungicides benomyl, thiophanate methyl, and thiabendazole showed excellent control effects when inoculated with drug-susceptible bacteria.

【table】

[Table] Test Example 8 Rice Blast Control Effect A 90 ml plastic pot was filled with rice soil, and rice (variety: Kinki No. 33) was sown. This was grown in a greenhouse, and a water-diluted solution of the test compound in the form of an emulsion was sprayed on the foliage of the seedlings at the 3-leaf stage until the droplets sufficiently adhered to the leaf surface. After the chemical solution was air-dried, a spore suspension of rice blast fungus (Pyricularia oryzae) was spray inoculated. This was kept under humid conditions at 28°C for 3 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, the compound of the present invention showed an excellent pesticidal effect.

[Table] Test Example 9 Phytotoxicity test on crops A 150 ml plastic pot was filled with sandy loam, and rubber barley (variety: Norin No. 61) and apple (variety: No. 61) were added.
Kogyoku) and peanuts (variety: Chiba semi-erect) 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 placed in the greenhouse again, and after cultivation for 10 days, the presence or absence of phytotoxicity was investigated according to the following criteria. Criteria for degree of drug damage (degree) (symptoms) - None. + Abnormalities caused by chemical damage are observed in some of the crops. Abnormalities due to chemical damage are observed throughout the crop. The plant dies due to chemical damage. As a result, as is clear from Table 11, the compound of the present invention had no harmful effect on crops, and the commercially available herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.

【table】

[Table] Next, examples of mixing the N-phenyl carbamate compound (), which is a compound of the present invention, with a benzimidazole thiophanate fungicide and a cyclic imide fungicide will be described. The benzimidazole thiophanate fungicides and cyclic imide fungicides used in the following test examples and formulation examples are shown in Table 12.

【table】

【table】

[Table] Test Example 10 Powdery mildew control effect of cucumber Powdery mildew control effect A 90 ml plastic pot was filled with sandy loam, and cucumber (variety: Sagami Hanshiro) was sown. This was cultivated at room temperature for 8 days to obtain 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 infected with powdery mildew fungus (Sphaerotheca fuliginea).
A conidial suspension obtained by mixing drug-resistant and susceptible bacteria was inoculated by spraying. The plants were cultivated in a greenhouse 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 13, any of the compounds of the present invention and compounds (A), (B), (C), (D), (E), (F),
When sprayed mixed with either (G) or (H),
A superior control effect was observed compared to when they were sprayed alone.

【table】

【table】

【table】

[Table] Test Example 11 Tomato gray mold control effect A 90 ml plastic pot was filled with sandy loam, and tomatoes (variety: Fukuju No. 2) were sown. This was cultivated in a greenhouse for 4 weeks to obtain tomato seedlings at the 4-leaf stage. A water-diluted solution of the test compound in the form of an emulsion or a wettable powder was applied to the foliage at 10 ml per pot.
Botrytis cinerea after chemical air drying
A conidial liquid obtained by mixing drug-resistant and susceptible bacteria was spray inoculated. After this was placed in a humid room condition at 20°C for 5 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 a result, as shown in Table 14, when any of the compounds of the present invention is mixed with any of compounds (I), (J), (K), or (L) and sprayed, and when they are sprayed alone, In comparison, excellent pest control effects were obtained.

【table】

【table】

[Table] Formulation Example 1 Powder 2 parts of Compound 2 of the present invention, 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder with a base ingredient content of 2%. Formulation Example 2 Wettable powder: 30 parts of Compound 15 of the present invention, 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate)
1 part and 2 parts of a dispersant (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder with a base ingredient content of 30%. Formulation Example 3 Wettable powder 50 parts of the present compound 5, 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly grinding and mixing 2.5 parts, a hydrating agent with a base ingredient content of 50% can be obtained. Formulation Example 4 Emulsion 10 parts of Compound 22 of the present invention, 80 parts of cyclohexanone and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) are mixed to obtain an emulsion with a base ingredient content of 10%. Formulation Example 5 Powder If 2 parts of the compound 107 of the present invention, 88 parts of clay and 10 parts of talc are thoroughly ground and mixed, the base agent content will be 2%.
Obtain a powder. Formulation Example 6 Wettable powder 30 parts of the present compound 54, 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate)
1 part and 2 parts of a dispersant (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder with a base ingredient content of 30%. Formulation Example 7 Wettable powder 50 parts of the present compound 164, 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly grinding and mixing 2.5 parts, a hydrating agent with a base ingredient content of 50% can be obtained. Formulation Example 8 Emulsion 10 parts of the present compound 101, 80 parts of cyclohexanone
and 10 parts of emulsifier (polyoxyethylene alkyl allyl ether), the main ingredient content is 10 parts.
% emulsion is obtained. Formulation Example 9 Powder 2 parts of the compound 44 of the present invention, 88 parts of clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder with a base ingredient content of 2%. Formulation Example 10 Wettable powder: 30 parts of 79 parts of the compound of the present invention, 45 parts of diatomaceous earth, 20 parts of white carbon, wetting agent (sodium lauryl sulfate)
By thoroughly pulverizing and mixing 3 parts and 2 parts of a dispersant (calcium lignin sulfonate), a wettable powder having a base ingredient content of 30% can be obtained. Formulation Example 11 Wettable powder 50 parts of 29 parts of the compound of the present invention, 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly grinding and mixing 2.5 parts, a hydrating agent with a base ingredient content of 50% can be obtained. Formulation Example 12 Emulsion 10 parts of the compound 81 of the present invention, 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%. Formulation example 13 Powder 1 part of compound (15), 1 part of compound (I), clay
By thoroughly grinding and mixing 88 parts of talc and 10 parts of talc, a powder with a base ingredient content of 2% is obtained. Formulation example 14 Powder Compound (105) 2 parts, Compound (E) 2 parts, Clay 86
By thoroughly grinding and mixing 10 parts of talc and 10 parts of talc, a powder with a base ingredient content of 4% is obtained. Formulation example 15 Wettable powder: 20 parts of compound (141), 10 parts of compound (J), 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate), and 2 parts of dispersing agent (calcium lignin sulfonate). By thoroughly grinding and mixing, a hydrating agent with a base ingredient content of 30% can be obtained. Formulation example 16 Wettable powder Compound (181) 10 parts, Compound (B) 40 parts, Diatomaceous earth 45
1 part, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and 2.5 parts of dispersing agent (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder with a base ingredient content of 50%. Formulation example 17 Wettable powder Compound (54) 25 parts, Compound (I) 50 parts, diatomaceous earth
By thoroughly grinding and mixing 18 parts of wetting agent (calcium alkylbenzene sulfonate), 3.5 parts of wetting agent (calcium alkylbenzenesulfonate), and 3.5 parts of dispersing agent (calcium lignin sulfonate), a wettable powder with a base ingredient content of 75% is obtained. Formulation example 18 Wettable powder Compound (105) 20 parts, Compound (A) 30 parts, powdered sucrose 40 parts, white carbon 5 parts, wetting agent (sodium lauryl sulfate) 3 parts, and dispersant (calcium lignin sulfonate) By thoroughly pulverizing and mixing the two parts, a wettable powder with a base ingredient content of 50% can be obtained.

Claims (1)

[Claims] 1. General formula [In the formula, X and Y are the same or different, and are any of a halogen atom, a lower alkyl group, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxy group, a cyano group, or a halogen atom, a hydroxyl group, or At least one of the cyano groups
lower alkyl group substituted with 1 atoms or substituents, or a substituent represented by the following general formula; _-CH2
OR ₃ , -COOR ₃ , [Formula] [Formula] COR ₆ , -CH=N-OR ₆ , -CO-NH-R ₆ (However, R ₃ is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower It represents a haloalkyl group. R ₄ and R ₅ are the same or different and represent a lower alkyl group. n represents an integer of 2, 3 or 4.
R ₆ represents a hydrogen atom or a lower alkyl group. ) is shown. Z represents an oxygen atom or a sulfur atom. R ₁
represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with at least one atom or substituent among a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. _R2 is a _C1 - _C8 alkyl group, _C3
~ _C8 alkenyl group, _C3 to _C8 alkynyl group,
lower cycloalkyl group, lower haloalkenyl group,
Any of the lower haloalkynyl groups, or at least one atom of a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group, a lower cycloalkyl group, or Indicates a lower alkyl group substituted with a substituent. however,
When X and Y are both a bromine atom, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not a propargyl group, X and Y are both a methoxy group, and R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not an ethyl group, X and Y are both an ethoxy group and R ₁ is an ethyl group, and Z is an oxygen atom, R ₂ is not an ethyl group,
When Y is a halogen atom, R ₁ is a lower alkyl group optionally substituted with a halogen atom, and Z is a sulfur atom, R ₂ is neither a methyl group nor an ethyl group, and X and Y are a halogen atom, When R ₁ is a lower alkyl group or a lower alkoxy group and Z is an oxygen atom, R ₂ has the general formula -W-C≡C-R ₇ (wherein, W represents an alkylene group, R ₇ represents an alkyl group.) is not a substituent. ] 2 General formula [Wherein, X and Y are the same or different, fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, n-butyl group,
vinyl group, 1-propenyl group, 2-propenyl group, ethynyl group, methoxy group, ethoxy group, cyano group, 1,2-dibromoethyl group, hydroxymethyl group, cyanomethyl group, 2-cyanoethyl group,
2-cyanovinyl group, methoxymethyl group, ethoxymethyl group, allyloxymethyl group, propargyloxymethyl group, 2-fluoroethoxymethyl group, methoxycarbonyl group, ethoxycarbonyl group, allyloxycarbonyl group, 2-fluoroethoxycarbonyl group, It shows a propargyloxycarbonyl group, a dimethoxymethyl group, a diethoxymethyl group, an ethylenedioxymethyl group, a formyl group, an acetyl group, a hydroxyiminomethyl group, a methoxyiminomethyl group, a carbamoyl group, and an N-methylcarbamoyl group. R ₁ is a methyl group, an ethyl group,
n-propyl group, allyl group, propargyl group, 2
-butenyl group, 3-butenyl group, 3-butynyl group, difluoromethyl group, 2-chloroethyl group,
It shows a 2,2,2-trifluoroethyl group, a 2-methoxyethyl group, and a cyclopropylmethyl group.
R ₂ is a methyl group, an ethyl group, an isopropyl group,
sec-butyl group, allyl group, 1-ethylpropyl group, 1-ethyl-2-propynyl group, 1-methyl-2-propynyl group, 1-methyl-butyl group, 1
-Methyl-pentyl group, 1-methyl-heptyl group, 1-methyl-2-propenyl group, propargyl group, 2-butenyl group, 1-methyl-3-butenyl group, 1-pentyl-2-propenyl group, 2- Butynyl group, 3-butynyl group, 1-methyl-3-butynyl group, 1-butyl-2-propynyl group, 1-
pentyl-2-propynyl group, cyclobutyl group,
2-cyanoethyl group, 2-fluoroethyl group, 2
-chloroethyl group, 2-bromoethyl group, 2,
2,2-trifluoroethyl group, 1-fluoromethyl-2-fluoroethyl group, 1-chloromethylethyl group, 1-bromomethylpropyl group, 1-methoxymethyl-2-chloroethyl group, 4-chloro-2- butenyl group, 4-chloro-2-butynyl group, 1-cyclopropylethyl group, 1-cyclopentylethyl group, 2-n-propoxyethyl group,
2-isopropoxyethyl group, 2-allyloxyethyl group, 2-methoxyethyl group, 2-(2-chloroethoxy)ethyl group, 2-benzyloxyethyl group, 1-methyl-2-methoxyethyl group, 1
-Methyl-2-n-butoxyethyl group and 1-methyl-2-phenoxyethyl group. Z represents an oxygen atom or a sulfur atom. However, when X and Y are both bromine atoms, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not a propargyl group,
When X and Y are both methoxy groups, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not an ethyl group, and X and Y are both ethoxy groups.
When R ₁ is an ethyl group and Z is an oxygen atom,
_R2 is not an ethyl group, and X and Y are fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, n-butyl group
When R 1 is a methoxy group or an ethoxy group, R ₁ is a methyl group, ethyl group or n-propyl group, and Z is an oxygen atom, R ₂ is not a 2-butynyl group. ] The N-phenyl carbamate compound according to claim 1. 3 General formula [Wherein, X and Y are the same or different, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, 1-propenyl group, vinyl group, allyl group, ethynyl group, methoxy group, It shows a cyano group, 1,2-dibromoethyl group, methoxymethyl group, methoxycarbonyl group, dimethoxymethyl group, diethoxymethyl group, acetyl group, and methoxyiminomethyl group. R ₁ represents a methyl group, an ethyl group, an allyl group, a propargyl group, a difluoromethyl group, or a 2-chloroethyl group. R ₂ is a methyl group, ethyl group, isopropyl group, sec-butyl group,
Allyl group, 1-ethylpropyl group, 1-ethyl-
2-propynyl group, 1-methyl-2-propynyl group, 1-methyl-2-propenyl group, propargyl group, 2-butenyl group, 2-butynyl group, 1-methyl-3-butynyl group, 2-cyanoethyl group, 1
-fluoromethyl-2-fluoroethyl group, 1-
Fluoromethyl-2-fluoroethyl group, 1-chloromethylethyl group, 1-methoxymethyl-2-
Chloroethyl group, 4-chloro-2-butynyl group,
1-cyclopropylethyl group, 2-(2-chloroethoxy)ethyl group, 1-methyl-2-methoxyethyl group, 1-methyl-2-methoxyethyl group,
Indicates a 1-methyl-2-n-n-butoxyethyl group. However, if X and Y are both bromine atoms and
When R ₁ is a methyl group, R ₂ is not a propargyl group, and X and Y are both a methoxy group and
When R ₁ is a methyl group, R ₂ is not an ethyl group,
Furthermore, X and Y are simultaneously ethoxy groups, and R ₁
is an ethyl group, R ₂ is not an ethyl group, but X,
When Y is a chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, n-propyl group, methoxy group or ethoxy group, and R ₁ is a methyl group or an ethyl group, R ₂ is not a 2-butynyl group. ] The N-phenyl carbamate compound according to claim 1 or 2. 4 General formula [Wherein, when X is a methoxy group or an ethoxy group, Y is a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, a methoxy group, an ethoxy group,
Indicates a cyano group, methoxymethyl group, methoxycarbonyl group, dimethoxymethyl group, and acetyl group.
R ₁ is ethyl group, allyl group, propargyl group, 2
- indicates a chloroethyl group. R ₂ is a methyl group, ethyl group, isopropyl group, sec-butyl group, allyl group, 1-methyl-2-propenyl group, 1-methyl-2-propynyl group, propargyl group, 2-cyanoethyl group, 2-butynyl group , 4-chloro-2-
It shows a butynyl group and a 1-methyl-2-methoxyethyl group. However, when X and Y are both ethoxy groups and R ₁ is an ethyl group, R ₂ is not an ethyl group, but X is a methoxy or ethoxy group and Y is a chlorine atom, a bromine atom, a methyl group, an ethyl group, When n-propyl group, methoxy group or ethoxy group,
R ₂ is not a 2-butynyl group. ] The N-phenyl carbamate compound according to claim 1, 2, or 3. 5 General formula [In the formula, X and Y are the same or different and represent a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, or a methoxymethyl group. R ₁ is an ethyl group,
Indicates an allyl group, a propargyl group, and a 2-chloroethyl group. R ₂ is a methyl group, ethyl group, isopropyl group, sec-butyl group, allyl group, 1-methyl-
2-propenyl group, 1-methyl-2-propynyl group, propargyl group, 2-cyanoethyl group, 2-
Butynyl group, 4-chloro-2-butynyl group, 1-
Indicates methyl-2-methoxyethyl group. however,
When X, Y are chlorine atom, bromine atom, methyl group, ethyl group or n-propyl group and R ₁ is ethyl group,
R ₂ is not a 2-butynyl group. ] The N-phenyl carbamate compound according to claim 1, 2, or 3. 6. Among the compounds shown in claim 4, a compound in which Y is a chlorine atom, a methyl group, a methoxymethyl group, or a cyano group. 7. Among the compounds shown in claim 5, a compound in which X and Y are the same or different and are a chlorine atom, a methyl group, or a methoxyethyl group. 8. Among the compounds shown in claim 6, a compound in which R ₁ is an ethyl group. 9. Among the compounds shown in claim 7, a compound in which R ₁ is an ethyl group. 10 General formula [In the formula, X and Y are the same or different, and are any of a halogen atom, a lower alkyl group, a lower alkenyl group, a lower cyanoalkenyl group, a lower alkynyl group, a lower alkoxy group, a cyano group, or a halogen atom, a hydroxyl group, or a lower alkyl group substituted with at least one atom or substituent of a cyano group,
or a substituent represented by the following general formula; -CH ₂
OR ₃ , -COOR ₃ , [Formula] [Formula] -COR ₆ , -CH=N-OR ₆ , -CO-NH-R ₆ (However, R ₃ is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, Represents a lower haloalkyl group. R ₄ and R ₅ are the same or different and represent a lower alkyl group. n represents 2, 3 or 4. R ₆ represents either a hydrogen atom or a lower alkyl group.) show. Z represents an oxygen atom or a sulfur atom. R ₁
represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkyl group substituted with at least one atom or substituent among a halogen atom, a lower alkoxy group, or a lower cycloalkyl group. _R2 is a _C1 - _C8 alkyl group, _C3
~ _C8 alkenyl group, _C3 to _C8 alkynyl group,
lower cycloalkyl group, lower haloalkenyl group,
Any of the lower haloalkynyl groups, or at least one atom of a halogen atom, a cyano group, a lower alkoxy group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group, a lower cycloalkyl group, or Indicates a lower alkyl group substituted with a substituent. however,
When X and Y are simultaneously a bromine atom, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not a propargyl group, X and Y are simultaneously a methoxy group, R ₁ is a methyl group, and Z is an oxygen atom, R ₂ is not an ethyl group, X and Y are both an ethoxy group and R ₁ is an ethyl group, and Z is an oxygen atom, R ₂ is not an ethyl group,
When Y is a halogen atom, R ₁ is a lower alkyl group optionally substituted with a halogen atom, and Z is a sulfur atom, R ₂ is neither a methyl group nor an ethyl group, and X and Y are a halogen atom, When R ₁ is a lower alkyl group or a lower alkoxy group and Z is an oxygen atom, R ₂ has the general formula -W-C≡C-R ₇ (wherein, W represents an alkylene group, R ₇ represents an alkyl group). ] An agricultural and horticultural fungicide characterized by containing the following N-phenyl carbamate compound as an active ingredient.