JPS5855140B2 - Drug-resistant bacteria control agent - Google Patents

Description

Detailed Description of the Invention The present invention is based on the general formula [■] [wherein X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom.

R represents a methyl group, an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, a chlorine atom, a bromine atom, or an iodine atom, or X and Y are different from each other; -3 When an alkoxyl group or an iodine atom is represented, it represents a methyl group or an ethyl group, and when X and Y simultaneously represent a methyl group, it represents a methyl group.

An N-phenyl carbamate compound represented by the formula, its production method, and a benzimidazole- or thiophanate-based fungicide (hereinafter referred to as benzimidazole-thiophanate-based fungicide)-resistant bacterial control agent containing the compound as an active ingredient. It is.

The present inventors previously prepared a compound of the general formula [A] [wherein X represents a chlorine atom or a bromine atom, and R represents a methyl group or an ethyl group, respectively.

] The N-phenyl carbamate compounds shown in the formula have a selectively strong bactericidal effect against plant pathogenic bacteria and other filamentous fungi (hereinafter referred to as drug-resistant bacteria) that are resistant to benzimidazole/thiophanate fungicides as described below. We found that this shows that

As a result of further studies, it was discovered that the N-phenyl carbamate compound represented by the general formula [■] is also effective against drug-resistant bacteria, and the present invention was completed.

The N-phenylcarbamate compound represented by the general formula CI, :] is benomyl[methyl l-(butylcarbamoyl]benzimidazole-2-yl-bamate).
, fubelidazole (2-(2-funol)benzimidazole), thiabendazole (2-(4-thiazolyl)benzimidazole), carpendazim [methyl benzimidazol 2-yl carbamate], thiophanate methyl [1,2-bis(3-methoxy) carbonyl 2
-thiourido)benzene], thiophanate [1,2
-Bis(3-ethoxycarbonyl-2thioureido)benzene] is characterized by a strong selective bactericidal effect against drug-resistant bacteria that are resistant to benzimidazole/thiophanate fungicides.

The aforementioned benzimidazole/thiophanate fungicides exhibit excellent control effects against various pathogenic bacteria parasitic on 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 have become widespread, and the control effect of drugs has decreased, often making them unusable.

Even if fungicides were sprayed, the expected control effect could not be obtained.
If the outbreak of diseases cannot be suppressed, farmers and other chemical users will suffer tremendous damage.

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, for example, in a field where no pesticidal effect is observed even after spraying Benomyl, no pesticidal effect can be expected even if other benzimidazole/thiophanate fungicides are sprayed.

In fields where drug-resistant bacteria are prevalent, we have no choice but to stop using benzimidazole/thiophanate fungicides.
There are many known cases in which the density of drug-resistant bacteria does not decrease even after discontinuing use, and once drug-resistant bacteria occur, they will be affected for a long time.

In addition, in such fields, target diseases are controlled by spraying other fungicides to which drug-resistant bacteria do not show cross-resistance, but benzimidazole/thiophanate fungicides are superior. There are very few species that show pesticidal effects, making accurate pest control difficult.

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. He worked hard to invent a drug.

As a result, it was found that the above-mentioned N-phenylcarbamate compound is a bactericidal agent that exhibits a strong bactericidal effect selectively against drug-resistant bacteria.

In other words, as is clear from the test examples described below, the compound of the present invention does not exhibit any control effect on diseases caused by wild bacteria that are susceptible to benzimidazole/thiophanate fungicides (hereinafter referred to as drug-susceptible bacteria); The compounds of the present invention exhibited excellent control effects against diseases caused by resistant bacteria, and the bactericidal activity of the compounds of the present invention against drug-resistant bacteria was extremely selective.

For certain types of drug-resistant bacteria mentioned above, the herbicides are alvarpan [4-chloro-2-butynyl N-(3-chlorophenyl) carbamate] and chlorpfam [1-phthyl-2-propynyl N-(3-chlorophenyl)]. carbamate], chlorpropham [isopropyl N-(3-
It has already been reported that chlorophenyl [carbamate] and propham [isopropyl N-phenyl carbamate] exhibit selective bactericidal activity.

(C6R1Acad, Sc, Parislt, 289.
5erie D, pp. 691-693, 1979).

However, as is clear from the test examples described later, the compound of the present invention exhibits a far superior control effect against drug-resistant bacteria compared to these herbicides, and has almost no phytotoxic effects on agricultural and horticultural crops, making it unsuitable for practical use. It is of high value.

On the other hand, as is clear from its properties as a herbicide, the above-mentioned herbicides have a strong phytotoxic effect on agricultural and horticultural crops when sprayed on foliage, and their bactericidal effect on bacterial fungi is not strong enough for practical use. do not have.

As mentioned above, the compound of the present invention exhibits a strong bactericidal effect selectively against bacteria that are resistant to benzimidazole/thiophanate fungicides. It can be used to control resistant bacteria.

For example, apple udon and disease bacteria (Podosphae
ra 1eucotricha), Sclerosis fungus (Ve
Mycosphaerella pomi, Marssonina mali, Clerotinia mali, Phyllactinia ka k
icola ), anthracnose (Gloeosporium
kaki), peach sclerotinosis fungus (S clerotin)
ta cinerea), Clados
porium carpophilum), Phomopsis sp.
Botrytis cine
rea ), Cercospora vi
ticola), powdery mildew (Vncinula
necator), black and five disease fungi (Elsinoea
mpelina), late rot fungus (G lomerell
acingulata), sugar beet brown spot fungus (Ce
rcospora beticola), beannut brown spot fungus (CerCospora arach)
idicola), Cercospora
personata), powdery mildew fungus of barley (Erysiphe graminis f, sp.
hordei), eye spot fungus (Cercos
pore 11aherpotrichoides)
, Fusarium Hivale,
Powdery mildew fungus of wheat (Erysiphegramin)
is f, sp, tritici), powdery mildew of cucumber (5phaerotheca fuligi)
nea ), Mycosphaerel
la melonis), Sclerotinia fungus (5clerot
inia sclerotiorum), Botrytis cinerea, Cladosporium cucumerin
um), tomato leaf mold fungus (Cladospori
um fulvum), botrytis fungus (Botryti
s cinerea), eggplant black blight fungus (Cory
nespora melongenae), strawberry powdery mildew fungus (5phaerotheea humu
li), Fusarium oxyspo
rum f, sp, fragariae), onion gray rot fungus (Bottytis alli)
, 5clerotinia sc
lerotiorum), cell 9-spot disease fungus (Cer.
cospora api i), Phaeoisariopsis grise
ola), hop botrytis fungus (Botrytis
cinerea), five mildew fungi of tobacco (Erysi
phecichoracearum), rose blight fungus (Dipl.

carpon rosae), tangerine scab fungus (Elsinoe fawcetti), blue mold fungus (Penicillium italicum)
, Penicillium digit
Atum) and other drug-resistant bacteria can be controlled.

On the other hand, it has also been revealed that the compound of the present invention is highly safe for humans, livestock, and fish, and can be used without causing any harm to agriculturally useful crops.

The compound of the present invention [■] is a new compound and can be produced by the following method.

(a) General formula [■] [In the formula, X and Y are as described above.]

Aniline derivatives represented by general formula (III)] [In the formula, R is as described above.]

] A manufacturing method that involves reacting with a chloroformate shown in ].

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

The reaction is cooled or heated (0 to 150°C) as necessary.
), the reaction 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 (II) in leg-making a) is described, for example, in Pharmaceutical Journal 85.314-317 (19
65), Ber,, 4.3343-3354 (190
It can be easily obtained by the method described in 1).

(b) General formula (IV) [In the formula, X and Y are as described above.]

] Phenyl isocyanate derivatives represented by the general formula [
V] 0H (V) [wherein R is as described above.

A production method that involves reacting with an alcohol 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, diethylaniline, 1,4- diazabicyclo(
2.2.2) Octane can be used as a catalyst.

By cooling or heating (0 to 50° C.) as necessary, the reaction 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 CIV) can be obtained by reacting the aniline derivative represented by the general formula (II) with phosgene.

This reaction is carried out in an organic solvent such as benzene, toluene, xylene, ethyl acetate or a mixture thereof.

By heating from 50° C. to reflux temperature as necessary, the reaction can be completed instantly in 10 hours, and the desired product can be obtained in good yield.

Next, examples of the compounds of the present invention represented by general formulas CI and 1 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 examples.

Next, the present invention will be explained in more detail with reference to Examples.

Example 1 Synthesis of ethyl N-[(3,5-diisopropyloxy)phenyl]carbamate (according to method (a)) 3,5-diisopropyloxyaniline 21 and diethylaniline 1.5? was dissolved in 20 ml of benzene, and 1.2 L of ethyl chloroformate was added under water cooling. was added dropwise over 5 minutes.

After being left at room temperature for 12 hours, it was poured into ice water and extracted with ethyl acetate.

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 silica gel column chromatography using a mixed solvent of benzene and tetrahydrofuran to obtain ethyl N([3,5-diisopropyloxy)phenyl fucarbamate 1.91%
was obtained (yield 67.6%).

Melting point 81.5-82℃ Elemental analysis value N (%) C (%) H (%) Calculated value 4.98 64.03 8.24 (Cl5H2
(as 3NO4) Actual value 4.93 63.99 8.32 Example 2 Methyl N-((3,5-dimethoxy)phenyl fluoride)
Synthesis of bamate (according to method (b)).

) 3,5-dimethoxyaniline 8.41 to toluene 10
The mixture was dissolved in a volume of 0 ml and added dropwise to a toluene solution containing 20P of phosgene at 10 to 20°C.

After gradually heating and refluxing for 30 minutes, the mixture was returned to room temperature and the solvent was distilled off under reduced pressure to obtain (3,5-dimethoxy)phenylisocyanate) 9.1'.

Without purification, this was added to methanol 501rle containing triethylamine 1z.

After being left at room temperature for 12 hours, it was poured into ice water and extracted with ethyl acetate.

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 silica gel column chromatography using a mixed solvent of benzene and tetrahydrofuran to obtain methyl N-((3.5-
Dimethoxy) phenyl fucarbamate 10.2P was obtained (yield: 88% from 3.5-dimethoxyaniline).

Melting point 64.5-65℃ Elemental analysis value N (%) C (%) H (%) Calculated value 6.63 56,86 6.20 (C1o H
(as t 304 N) Actual value 6.65 56°97 6.31 When the compound of the present invention thus obtained is actually applied, it can be used in pure form without adding other components; To make it easier to use as a fungicide, it can be mixed with a carrier and applied in commonly used forms such as powders, wettable powders,
It can be used as an oil solution, emulsion, tablet, granule, fine granule, aerosol, flowable, etc.

Since the compound of the present invention shows high bactericidal activity selectively only against drug-resistant bacteria, it can be used alone when only drug-resistant bacteria are present, but when drug-sensitive wild bacteria are present, it can be used alone. It is desirable to use them in combination with the benzimidazole/thiophanate fungicides mentioned above, or to use them alternately.

The preparations generally contain active compounds (including mixed ingredients).
1.0 to 95.0%, preferably 2.0 to 95.0% by weight
Contains 80.0%, usually 10 to 100 per 10 ares
An application rate of 2 is appropriate.

Furthermore, the concentration used is preferably in the range of 0.005% to 0.5%, but the amount and concentration used depend on the dosage form, application period,
Since it varies depending on the method, location, target disease, target crop, etc., there is no problem in increasing or decreasing the amount without being limited to the above range.

Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.
3,5-dichlorophenyl)-1,2 dimethylcyclofuropane-1,2-dicarboximide, S-normal-
Butyl s-paratertiary butylbenzyl dithiocarbon imitate, 0-0-dimethyl 0-(2,6-dichloro4-methylphenyl) phosphorothioate, methyl 1-butylcarbamoyl-IH-benzimidazole-2-yl-bamate, N -trichloromethylthio-
4-cyclohexenate 2-dicarboximide, cis-N-(1.1.2.2tetrachloroethylthio)-4
-Cyclohexendo 2-dicarboximide, polyoxine, streptomycin, zinc ethylene bisdithiocarbamate, zinc dimethylthiocarbamate, manganese ethylene bisdithiocarbamate, bis(N-
N-dimethylthiocar/(moyl)disulfide, tetrachloroisophthalonitrile, 8-hydroxyquinoline, dotesylguanidine acetate, 5,6-sihydro-2-methyl-1,4-oxathiin-3-carboxanilide, N/- dichlorofluoromethylthio-N-N-
Dimethyl N/-phenylsulfamide, 1-(4-chlorophenoxy)-3,3-dimethyl-1-((2,4
-triazol-1-yl)-2-butanone, 1,2-
Bis(3-methoxycarbonyl-2-thioureido)benzene, methyl N-(2,6-dimethylphenyl)-N
- Disinfectants such as methoxyacetyl-2-methylglycinate, aluminum ethyl phosphite, 2,4-dichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxybutyric acid, 2-methyl-4-chlorophenoxyacetic acid (esters, salts) ), 2,4-dichlorophenyl 4'-nitrophenyl ether, 2,4-dichlorophenyl 4'-nitrophenyl ether,
6-) IJ Chlorphenyl 4'-nitrophenyl ether, 2-chloro-4-)lifluoromethylphenyl 3'-ethoxy-41-nitrophenyl ether,
Diphenyl ether herbicides such as 2,4-dichlorophenyl 4'-nitro-37-medoxyphenyl ether, 2,4-dichlorophenyl 37-medoxycarbonyl-4'-nitrophenyl ether, 2-chloro- 4,6-bisethylaminote 3,5-triazine, 2-chloro-
4ethylamino-6-improvil aminonot 3,5-
Triazine, 2-methylthio-4,6-bisethylaminote 3,5-triazine, 2-methylthio-4,6-
Triazine herbicides such as bisisopropylaminot 3,5-triazine, 3(3,4-dichlorophenyl)-
1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea, 1-(α・
α-dimethylbenzyl)-3-p-)lilurea, ■-
Urea herbicides such as (2-benzothiazolyl)-1,3-dimethylurea, carbamate herbicides such as isopropyl N-(3-chlorophenyl) carbamate, methyl N-(3,4-dichlorophenyl) carbamate, 5-(
Thiol carbamate herbicides such as 4-chlorobenzyl) N-N-diethylthiol carbamate and S-ethyl N-N-hexamethylenethiol carbamate, 3.4
-dichloropropionanilide, 2-chloroN-methoxymethyl-2',6'-diethylacetanilide, 2-
Chloro-2',6'-diethyl-N (butoxymethyl)
-acetanilide, 2-chloro-2',6'-diethyl-N-(n-propoxyethyl)acetanilide, N-
Acid anilide herbicides such as chloroacetyl-N(2,6-dichlorophenyl)chrysin ethyl ester, 5-bromo-3-secondary-butyl-6-methyluracil, 3
-Uracil herbicides such as cyclohexyl-5,6-trimethyleneuracil, pyridinium salt herbicides such as 1,1'-dimethyl 4,4'-bipyridinium chloride, N
-(phosphonomethyl)glycine, N-N-bis(phosphonomethyl)glycine〇-ethyl 0-(2-nitro-5-
methylphenyl)N-secondary-butylphosphoramidothio-I--), 5-(2-methyl-1-piperidylcarbonylmethyl)0-0-di-n-propyldithiophosphate, 5-(2-methyl- Phosphorus herbicides such as 1-piperidylcarbonylmethyl) 0-0-diphenyl or di-n-propyldithiophosphate, α・α・α-
Toluidine herbicides such as trifluoro-2,6-sinitro N-N-digropyr-p-toluidine, 5-tert-butyl 3-(2,4-dichloro-5-infropoxyphenyl)-1,3,4 -Oxadiazoline-2-
one, 3-inpropyl-(IH)-2,1,3-benzothiadiazin-(3H)-one-2,2-dioxide, α-(β-naphthoxy)propionanilide, 4-
(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl p-toluenesulfonate, 3-(
methoxycarbonylamino)phenyl 3-methylphenylcarbamate, 4-amino-3-notyl-6-phenyroot 2,4-triazine, 0-O-dimethyl 0-(
4-Nitro-3-methylphenyl) phosphorothioate, 0-(4-cyanophenyl)O.O-dimethylphosphorothioate, 0-(4-cyanophenyl)O-ethylphenylphosphonothioate, 0.0-dimethyl 5-(
N-methylcarbamoylmethyl)phosphorodithioate, 2-methoxy-4H-1,3,2-benzodioxaphosphorine-2-sulfide, 0-O-dimethyl S(1-
-Organophosphorus insecticides such as -[-)4dicarbonyl-1-phenylmethyl)phosphorodithioate, α-cyano-3
-Phenoxybenzyl 2-(4-chlorophenyl)invalerate, 3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclofuropanecarboxylate, α-cyano-3-phenoxybenzyl 2
- Can be used in combination with pyrethroid insecticides such as 2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate, without reducing the control effect of each single agent. Furthermore, a synergistic effect by mixing is also expected.

Next, test examples and formulation examples will be given to further clarify the usefulness of the compounds of the present invention as agents for controlling drug-resistant bacteria.

Test Example 1 Cucumber Powdery Mildew Control Effect A 90 ml plastic pot was filled with sandy loam, and cucumbers (variety: Sumo Hanshiro) were sown.

This was cultivated in a greenhouse 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 onto the foliage of the seedlings in an amount of 10 ml per pot.

After air-drying the chemical solution, seedlings were infected with chemical-resistant or sensitive cucumber powdery mildew fungus (5phaerotheca fuliginea).
) was inoculated by spraying with a conidial suspension.

This was 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 degree of appearance of leaf spots on the investigated leaves, 0.0.5.
The disease was classified into indexes 1.2.4 and the disease severity was calculated using the following formula.

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

As a result, as shown in Table 2, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, but did not show any control effect when inoculated with drug-susceptible bacteria.

On the other hand, commercially available fungicides benomyl, thiophanate methyl,
Both carpendazim and thiabendazole showed excellent control effects when inoculated with drug-resistant bacteria, and 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.

Test example 2 Sugar beet brown spot control effect 90ml! Fill a plastic pot with sandy loam,
Sugar beet (quality: Detroit dark red) was sown.

The seedlings obtained after 20 days of cultivation in a greenhouse were treated with a water diluted solution of the test compound in the form of an emulsion or wettable powder at 10% per pot.
Sprayed on the foliage by applying rIll.

After the chemical solution was air-dried, the seedlings were spray inoculated with a conidial suspension of a drug-resistant or sensitive sugar beet brown spot fungus (Cercospora beticola).

After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, the disease state was observed.

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

As a result, as shown in Table 3, similar to the results of Test Example 1, the compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria, whereas commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. showed excellent control effects.

Compounds with similar chemical structures and commercially available herbicides with similar chemical structures that were tested for comparison showed almost no control effect when inoculated with any of the bacteria.

Test Example 3 Effect on controlling pear blight A 90 ml plastic pot was filled with a mixed soil of peat moss and sandy loam, and seeds collected from pear fruits (variety: Nagakobu) were sown.

This was cultivated in a greenhouse for 20 days, and a water diluted solution of the test compound in the form of an emulsion or wettable powder was added to the resulting seedlings at 10% per pot.
I sprayed it on the stems and leaves.

After the chemical solution was air-dried, the seedlings were spray-inoculated with a conidial suspension of a drug-resistant or susceptible pear fungus (Venturianashicola).

47 Place this under humid conditions at 20℃ for 3 days, then
The plants were cultivated for 20 days under fluorescent lamp illumination at 0°C 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 4, the compounds 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 a small control effect when inoculated with drug-susceptible bacteria. did.

Test Example 4 Effect on controlling bean nut brown spot disease A plastic pot with a volume of 100 rnl was filled with sandy loam, and bean nuts (variety: Chiba erect) were sown.

The seedlings obtained after 14 days of cultivation in a greenhouse were treated with a water diluted solution of the test compound in the form of an emulsion or wettable powder at 10% per pot.
M1 was sprayed on the stems and leaves.

After air-drying the chemical solution, young seedlings were exposed to chemically resistant or susceptible peanut brown spot fungus (Cercospora arachidic).
A spore suspension of ola) was inoculated by spraying.

After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, the disease state was observed.

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

As 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-susceptible bacteria. Indicated.

Test Example 5 Effect on controlling mandarin blue mold disease Mandarin fruit (variety: Unshu) was thoroughly washed with water, air-dried, and then immersed for 1 minute in a chemical solution in which an emulsion of the compound of the present invention or a reference commercially available fungicide was diluted with water to a predetermined concentration.

After air-drying, the drug-resistant or susceptible tangerine blue fungus (P
enicillium italicum) conidia were soaked in water and inoculated by spraying onto the fruit surface.

After being kept in a moist room for 14 days after inoculation, the degree of disease onset was investigated using the disease index of 0.1.2.3.4.5 as shown below.

(Infection status) (Infection index) No lesions observed OOne lesion is observed on less than 20% of the fruit surface area * (Infection status) (Infection index) Lesions are observed in less than 20-40% of the fruit surface area Lesions are observed on less than 40 to 60% of the fruit surface area Lesions are observed on 60 to less than 80% of the fruit surface area Lesions are observed on more than 80% of the fruit surface area It was conducted in the same manner as Test Example 1.

As a result, as shown in Table 6, 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-susceptible bacteria. Ta.

Test Example 6 Phytotoxicity test on crops A 150 mg capacity plastic pot was filled with sandy loam.
Wheat (variety: Norin No. 61), apple (variety: Kogyoku),
Sow each type of Beanatsu (variety: Chiba erect),
Grown 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 cultivated for 10 days, after which the presence or absence of phytotoxicity was investigated according to the following criteria.

Criteria for degree of phytotoxicity* As a result, as is clear from Table 7, the compound of the present invention did not have a phytotoxic effect on crops, whereas a commercially available herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.

Formulation example l Powder 2 parts of the compound of the present invention 3, 88 parts of clay and 10 parts of talc
By thoroughly pulverizing and mixing the two parts, a powder containing 2% of the main ingredient can be obtained.

Formulation Example 2 Wettable powder: 30 parts of Compound 7 of the present invention, 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) are thoroughly ground and mixed to form the main ingredient. A hydrating agent with a content of 30% is obtained.

Formulation example 3 Irrigation agent If 50 parts of the present compound 2, 45 parts of diatomaceous earth, 2.5 parts of a wetting agent (calcium alkylbenzenesulfonate) and 25 parts of a dispersing agent (calcium ligninsulfonate) are thoroughly mixed as a powder, the main content will be Obtain 50% hydration.

Formulation Example 4 Emulsion 10 parts of Compound 8 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%.

Claims (1)

[Claims] 1 General formula [wherein X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom. R represents a methyl group, an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, a chlorine atom, a bromine atom, or an iodine atom, or X and Y are different from each other; An N-phenyl carbamate compound represented by the following when an alkoxyl group or an iodine atom of ~3 represents a methyl group or an ethyl group, and when X and Y both represent a methyl group, a methyl group. 2 General formula [wherein, X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom. Aniline derivatives represented by the general formula [wherein, or X and Y
When simultaneously represents an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, or an iodine atom, represents a methyl group or an ethyl group, and when X and Y simultaneously represent a methyl group,
Represents a methyl group. [In the formula, X, Y and R are as described above. A method for producing an N-phenyl carbamate compound represented by: 3 General formula [wherein X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom. Phenyl isocyanate derivatives represented by the general formula [wherein, , or X and Y
When simultaneously represents an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, or an iodine atom, represents a methyl group or an ethyl group, and when X and Y simultaneously represent a methyl group,
Represents a methyl group. [In the formula, X, Y and R are as described above.] ] A method for producing an N-phenyl carbamate compound. 4 General formula [wherein, X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom. A general formula obtained by reacting an aniline derivative represented by the following formula with phosgene [where X and Y are as described above]. ] Phenyl inocyanate derivatives represented by the general formula [wherein R is a methyl group, an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, a chlorine atom, a bromine atom, or an iodine atom, in which X and Y are different; or X and Y
When simultaneously represents an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, or an iodine atom, represents a methyl group or an ethyl group, and when X and Y simultaneously represent a methyl group,
Represents a methyl group. [In the formula, X, Y and R are as described above.] A method for producing an N-phenyl carbamate compound represented by: 5 General formula [wherein, X and Y are the same or different, a methyl group,
Ethyl group, alkoxyl group having 1 to 3 carbon atoms, chlorine atom,
Represents a bromine or iodine atom. R represents a methyl group, an ethyl group, an alkoxyl group having 1 to 3 carbon atoms, a chlorine atom, a bromine atom, or an iodine atom, or X and Y are different from each other; -3 When an alkoxyl group or an iodine atom is represented, it represents a methyl group or an ethyl group, and when X and Y simultaneously represent a methyl group, it represents a methyl group. A benzimidazole- or thiophanate-based fungicide-resistant bacteria control agent, which contains an N-phenylcarbamate-based compound as an active ingredient.