JPH0239503B2 - NNFUENIRUKAABAMEETOKEIKAGOBUTSU * SONOSEIZOHOOYOBISOREOJUKOSEIBUNTOSURUNOENGEIYOSATSUKINZAI - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [wherein R is the general formula -CH ₂ R' or -CH
(CH ₃ ) Represents a group represented by R″. Here, R′ represents a hydrogen atom or a methyl group, or represents a saturated or unsaturated carbon chain of C ₃ or less substituted with a chlorine atom. R″ represents a saturated or unsaturated carbon chain of C ₂ or less which may be substituted with a methoxy group, or represents a cyclopropyl group. The present invention relates to an N-phenyl carbamate compound represented by the formula, a method for producing the same, and an agricultural and horticultural fungicide characterized by containing the same as an active ingredient. The N-phenyl carbamate compounds represented by the general formula [] include benomyl [methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate], fuberidazole [2-(2-furyl)benzimidazole], and thiabendazole [2 -(4-thiazolyl)benzimidazole],
Carbendazim [methyl benzimidazole]
2-yl carbamate], thiophanate methyl [1,2bis(3-methoxycarbonyl-2
-thiourido)benzene], thiophanate [1,2-bis(3-ethoxycarbonyl-2-
It is characterized by a strong selective bactericidal effect against drug-resistant bacteria that are resistant to benzimidazole/thiophanate fungicides such as thioureidobenzene]. 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. Ta. However, when these fungicides are continuously sprayed on crops, drug-resistant bacteria spread, and the control effect of the fungicides decreases, often resulting in situations where they cannot be used in practice. If spraying a fungicide does not have the expected control effect and the outbreak of disease cannot be suppressed, the damage to farmers and other users of the fungicide will be 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, the target disease is controlled by spraying other fungicides to which drug-resistant bacteria do not show cross-resistance, but benzimidazole-thiophanate fungicides have better control effects. There are very few species that show this, making it difficult to properly control them. Taking the above circumstances into consideration, 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 are present, and therefore, a fungicide with such properties can be expected. He worked hard to invent 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, and the present invention has been completed. The herbicide Barban [4-chloro-2-butynyl N
-(3-chlorophenyl)carbamate], chlorbufuam [1-methyl-2-provinyl N-
(3-chlorophenyl) carbamate], chlorbrofum [isopropyl N-(3-chlorophenyl) carbamate], and profum [isopropyl N-phenyl carbamate] have been reported to exhibit selective bactericidal activity (CRAcad,
Sc.Paris, t.289, S'erie D pages 691-693, 1979
Year). However, as is clear from the test examples described below, the compound of the present invention exhibits a far superior control effect against drug-resistant bacteria compared to these herbicides,
Moreover, it has almost no phytotoxic effects on agricultural and horticultural crops, and has high practical value. On the other hand, as is clear from their properties as herbicides, the above-mentioned herbicides have strong phytotoxic effects on agricultural and horticultural crops when sprayed on foliage, and their bactericidal effects against drug-resistant bacteria are not strong enough for practical use. . As mentioned above, the compound of the present invention exhibits a strong bactericidal effect selectively against bacteria that are resistant to benzimidazole/thiophanate fungicides, and therefore, it is expected that the compounds will appear or have appeared as a result of the use of the above-mentioned fungicides. It can be used to control resistant bacteria. For example, powdery mildew (Podosphaera leucotricha) on apples, Venturia inaequalis, Mycosphaerella pomi, Marssonina mali, Solerotinia mali, and Phyllactinia kakicola on persimmons. , Gloeosporium kaki, Solerotinia 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 melonis, Solerotinia sclerotiorum, Botrytis cinerea, Cladosporium
cucumerinum), tomato leaf mold (Cladosporium fulvum), gray mold (Botrytis cinerea), eggplant black blight (Corynespora 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, Diplocarpon rosae, Elsinos fawcetti, Ponicillium italicum, and Penicillium digitatum. It can be used to control. 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 [ ] is a new compound, and can be produced, for example, by the following method. (a) 3,4-diethoxyaniline and general formula [In the formula, R has the same meaning as above. ] This reaction involves reacting benzene, toluene, xylene,
Diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate,
The reaction is carried out in an organic solvent such as pyridine, dimethylformamide, or a mixture thereof, and can be carried out in high yield by using a dehydrochlorination agent such as pyridine, triethylamine, diethylaniline, sodium hydroxide, potassium hydroxide, etc. can. The reaction is cooled or heated (0 to
(150°C), the process can be completed instantly to 10 hours, and the desired product can be obtained in good yield. The starting material, 3,4-diethoxyaniline, can be easily obtained, for example, by the method described in Organic Synthetic Chemistry 17 (3) 166 (1959). (b) 3,4-diethoxyphenyl isocyanate and the general formula ROH [wherein R has the same meaning as above]. ] This reaction can be carried out without solvent or with benzene, toluene,
In an organic solvent such as xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, carbon tetrachloride, etc. without a catalyst or triethylamine, diethylaniline, 1,4-diazabicyclo(2,2,
2) Can be carried out with octane as a catalyst. The reaction is cooled or heated as necessary (0 to 50
°C), the process can be completed from instantaneous to 10 hours.
The target product can be obtained in good yield. 3,4-diethoxyphenyl isocyanate can be obtained by reacting 3,4-diethoxyaniline and 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 or in 10 hours, and the desired product can be obtained in good yield. 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] Next, the present invention will be explained in more detail with reference to Examples. Example 1 Synthesis of isopropyl N-(3,4-diethoxyphenyl)carbamate (according to method (a)) 1.8 g of 3,4-diethoxyaniline and 1.5 g of diethylaniline were dissolved in 20 ml of benzene and cooled on ice. 1.2 g of isopropyl chloroformate to 5
It was dripped in minutes. After stirring at room temperature for about 3 hours, the mixture was poured into ice water and extracted with ether. After washing with water and drying with magnesium sulfate, the solvent was distilled off to give a crude crystal of 2.6
I got g. This product was recrystallized from ethanol to obtain 2.3 g of white crystals of isopropyl N-(3,4-diethoxyphenyl) carbamate. melting point
100-100.5℃ Elemental analysis value C (%) H (%) N (%) Calculated value 62.92 7.92 5.27 (as C ₁₄ H ₂₁ NO ₄ ) Actual value 62.75 7.96 5.41 NMR δCDCl ₃ (TMS) 1.32 (6H, d, J = 7.5Hz) 1.44 (H, t, J
= 9Hz) 1.46 (3H, t, J = 9Hz) 4.05 (2H,
q, J=9Hz) 4.07 (2H, q, J=9Hz)
5.02 (1H, sept.J=7.5Hz) 6.55 (1H, br.)
6.77 (2H, br.) 7.18 (1H, br) Example 2 1-Butyn-3-yl N-(3,4-
Synthesis of (diethoxyphenyl) carbamate (according to method (b)) 1 g of triethylamine and 0.8 g of 1-butyn-3-ol were dissolved in 20 ml of toluene, and 3,4
-2.1 g of diethoxyphenyl isocyanate was added dropwise. After stirring at room temperature for about 6 hours, the mixture was poured into ice water and extracted with ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off to obtain 2.8 g of crude crystals.
This product was purified by silica gel column chromatography using a mixed solvent of hexane and acetone.
2.6 g of white crystals of 1-butyn-3-yl N-(3,4-diethoxy-phenyl) carbamate were obtained. Melting point 116-117℃ Elemental analysis value C (%) H (%) N (%) Calculated value 64.96 6.90 5.05 (as C ₁₅ H ₁₉ NO ₄ ) Actual value 65.11 6.87 5.18 NMR δCDCl ₃ (TMS) 1.38 (6H, t , J=8Hz) 1.51(3H, dJ=
8Hz) 2.43 (1H, dJ=2Hz) 3.95 (4H, qJ
=8Hz) 5.35 (1H, dqJ=2Hz, J=8
Hz) 6.75 (3H, br.) 7.10 (1H, br.) When actually applying the compound of the present invention obtained in this way, it can be used in pure form without adding other ingredients, and To facilitate use as a fungicide, it can be mixed with a carrier and applied in any of the commonly used forms, such as powders, wettable powders, oils, emulsions, tablets, granules, microgranules, aerosols, flowables, etc. can also be used. 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 preferable to use them in combination with the above-mentioned penzimidazole thiophanate fungicides, or to use them alternately. The active compound is generally contained in the formulation by weight.
1.0-95.0%, preferably 2.0-80.0%,
Usually, an application amount of 10 to 100 g per 10 ares 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,
Since it varies depending on the application time, 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 and insecticides, such as N-(3,5-diclophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, (E)- 1-(2,
4-dichlorophenyl)-4,4-dimethyl-2
-(1,2,4-triazol-1-yl)-1
-Penten-3-ol, 4-chloro-3-methylbenzothiazolone, S-normal-butyl-S
- paratertiary butylbenzyldithicarbonimidate, O,O-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, N-(trichloromethylthio)phthalimide, 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-oxathiine-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, fungicides such as aluminum ethyl phosphite, O,O-dimethyl O-(4-nitro-3-methylphenyl)phosphorothioate, O- (4-cyanophenyl)
O,O-dimethylphosphorothioate, O-(4
-cyanophenyl)0-ethylphenylphosphonothioate, O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate, 2
-Organophosphorus insecticides such as methoxy-4H-1,3,2-benzodioxaphosphorine-2-sulfide, O,O-dimethyl S-(1-ethoxycarbonyl-1-phenylmethyl)phosphorodithioate, α-cyano-3-phenoxybenzyl 2-
(4-chlorophenyl)isovalerate, 3-phenoxybenzyl 2,2-dimethyl-3-(2,
2-dichlorovinyl) cyclopropane carboxylate, α-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylate, etc. by mixing with birethroid insecticides. They can be used together without reducing the control effect of each single agent, and furthermore, a synergistic effect is expected when mixed. Next, test series and formulation examples will be given to further clarify the usefulness of the compounds of the present invention as agricultural and horticultural fungicides. 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 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 on the foliage of the seedlings until the droplets were sufficiently attached 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 (Sphaerotheca 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 degree of lesion appearance on the investigated leaves, 0.05, 1,
The disease was classified into indexes 2 and 4, and the severity of the disease was calculated using the following formula. (Infected digits) (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) × (number of leaves) / (number of investigated leaves) × 4 × 100 Subsequently, the control value was calculated from 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 2, the compound of the present invention has excellent control when inoculated with drug-resistant bacteria. It showed no control effect when inoculated with drug-susceptible bacteria. On the other hand, none of the commercially available fungicides benomyl, thiophanate methyl, carbendazim, and thiabendazole 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.

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[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 sufficient droplets 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 3, similar to the results of Test Example 1, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, whereas the commercially available fungicides benomyl and thiophanate methyl When inoculated with susceptible bacteria, excellent control effects were shown. 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.

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[Table] Test Example 3 Pear scab control effect A 90 ml plastic pot was filled with mixed soil of peat moss and sandy loam, and seeds collected from pear fruits (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 a wettable powder was sprayed on the foliage of the seedlings grown for one day until the droplets were sufficiently attached 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 4, 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. It was shown to be effective.

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[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 culturing in a greenhouse for 14 days, a water-diluted solution of the test compound in the form of an emulsion or wettable powder was sprayed on the foliage of the seedlings until enough droplets adhered to the leaf surface. A spore suspension of susceptible peanut brown spot fungus (Cercospora arachidicola) was spray inoculated. 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 5, 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] 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 sprayed on the foliage of the seedlings until the droplets were sufficiently attached to the leaf surface. After air-drying the chemical solution, young seedlings are infected with chemical-resistant or susceptible botrytis 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 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 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.

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[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 newly developed leaves. 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 the droplets were sufficiently attached to the leaf surface. After the chemical solution was air-dried, a microflora section (diameter 5
mm) was pasted on the leaf surface and inoculated. This at 25℃
After being left under humid conditions for 4 days to develop the disease, 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.

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[Table] Test Example 7 Effect on controlling citrus blue mold disease After washing tangerine fruit (variety: Unshu) thoroughly with water and air drying, the emulsion of the compound of the present invention or a control commercially available fungicide was diluted with water to a specified concentration for 1 minute. Soaked. 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 the disease index of 0, 1, 2, 3, 4, and 5 as shown below. (Disease status) (Infection index) No lesions observed 0 Lesions observed on less than 20% of the fruit surface area 1 24-40 2 40-60 3 60-80 4 80% or more 5. The calculation of the disease severity and control value was carried out in the same manner as in Test Example 1. As a result, as shown in Table 8, 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. It was shown to be effective.

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[Table] Note (14) Commercial fungicide thiabendazole test example 8 Phytotoxicity test on crops Fill 150ml plastic pots with sandy loam, and add wheat (variety: Norin No. 61) and apple (variety: No. 61).
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 seeds 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 chemical damage (degree) (Symptoms) - No abnormality + Abnormality due to chemical damage is observed in part of the crop Abnormality due to chemical damage is observed throughout the crop Death withered due to chemical damage As a result, it is clear from Table 9 As can be seen, no phytotoxic effects on crops were observed in the compounds of the present invention, whereas phytotoxic effects were observed in commercially available herbicides with chemical structures similar to those used as controls.

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[Table] Note (15) Commercial herbicide Sweep formulation example 1 Dust 2 parts of the compound 5 of the present invention, 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a dust with a base ingredient content of 2%. Formulation Example 2 Wettable powder: 30 parts of the present compound 1, 45 parts of diatomaceous earth, 20 parts of white carbon, wetting agent (sodium lauryl sulfate) 3
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 3, 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly mixing 2.5 parts of powder, a wettable powder with a base ingredient content of 50% can be obtained. Formulation Example 4 Emulsion 10 parts of the compound 11 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%.

Claims (1)

[Claims] 1. General formula [wherein R is the general formula -CH ₂ R' or -CH
(CH ₃ ) Represents a group represented by R″. Here, R′ represents a hydrogen atom or a methyl group, or represents a saturated or unsaturated carbon chain of C ₃ or less substituted with a chlorine atom. R″ represents a saturated or unsaturated carbon chain of C ₂ or less which may be substituted with a methoxy group, or represents a cyclopropyl group. ] An N-phenyl carbamate compound represented by: 2 3,4-diethoxyaniline and general formula [wherein R is the general formula -CH ₂ R' or -CH
(CH ₃ ) Represents a group represented by R″. Here, R′ represents a hydrogen atom or a methyl group, or represents a saturated or unsaturated carbon chain of C ₃ or less substituted with a chlorine atom. R″ represents a saturated or unsaturated carbon chain of C ₂ or less which may be substituted with a methoxy group, or represents a cyclopropyl group. ] General formula characterized by reacting with a chloroformic acid ester represented by [In the formula, R has the same meaning as above. ] A method for producing an N-phenyl carbamate compound represented by: 3 3,4-diethoxyphenyl isocyanate and the general formula ROH [wherein R is the general formula -CH ₂ R' or -CH
(CH ₃ ) Represents a group represented by R″. Here, R′ represents a hydrogen atom or a methyl group, or represents a saturated or unsaturated carbon chain of C ₃ or less substituted with a chlorine atom. R″ represents a saturated or unsaturated carbon chain of C ₂ or less which may be substituted with a methoxy group, or represents a cyclopropyl group. ] A general formula characterized by reacting with an alcohol represented by [In the formula, R has the same meaning as above. ] A method for producing an N-phenyl carbamate compound represented by: 4 General formula [wherein R is the general formula -CH ₂ R' or -CH
(CH ₃ ) Represents a group represented by R″. Here, R′ represents a hydrogen atom or a methyl group, or represents a saturated or unsaturated carbon chain of C ₃ or less substituted with a chlorine atom. R″ represents a saturated or unsaturated carbon chain of C ₂ or less which may be substituted with a methoxy group, or represents a cyclopropyl group. ] An agricultural and horticultural fungicide characterized by containing an N-phenyl carbamate compound represented by the following as an active ingredient.