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    • 专利摘要:
    1. Claims for the contracting states : BE, CH, DE, FR, GB, IT, LU, NL, SE A 2-phenyl-4-pyrone derivative of the formula see diagramm : EP0017602,P16,F2 in which X1 and X2 , which are identical or different, each represent a hydrogen or halogen atom, with the proviso that at least one of these substituents represents a halogen atom, R1 represents an alkoxy radical containing from 1 to 4 carbon atoms, an alkenyloxy radical containing from 2 to 4 carbon atoms, the propargyloxy radical, a halogenalkoxy radical containing from 1 to 4 carbon atoms, an amino radical, an alkylamino radical containing from 1 to 4 carbon atoms or a dialkylamino radical in which the alkyl parts each of which comprising from 1 to 4 carbon atoms are identical or different, R2 represents a halogen atom, an alkyl radical containing from 1 to 5 carbon atoms, an alkoxy radical containing from 1 to 4 carbon atoms, an alkenyloxy radical containing from 3 to 4 carbon atoms, an alkynyloxy radical containing from 3 to 4 carbon atoms, an alkylthio radical containing from 1 to 4 carbon atoms, a halogenoalkyl radical containing from 1 to 4 carbon atoms, a halogenalkoxy radical containing from 1 to 4 carbon atoms, a halogenalkylthio radical containing from 1 to 4 carbon atoms or a nitro, hydroxyl, cyano or benzyloxy radical and n is an integer which can be equal to 0, 1, 2, 3, 4 or 5, it being understood that, if n is greater than or equal to 2, the substituents R2 can be identical or different. 1. Claims for the contracting state : AT A fungicidal composition, for protecting plants against fungal diseases, which contains, as active ingredient, at least one compound of the general formula : see diagramm : EP0017602,P17,F2 in which X1 and X2 , which are identical or different, each represent a hydrogen or halogen atom, with the proviso that at least one of these substituents represents a halogen atom, R1 represents an alkoxy radical containing from 1 to 4 carbon atoms, an alkenyloxy radical containing from 2 to 4 carbon atoms, the propargyloxy radical, a halogenalkoxy radical containing from 1 to 4 carbon atoms, an amino radical, an alkylamino radical containing from 1 to 4 carbon atoms or a dialkylamino radical in which the alkyl parts (C1 -C4 ) are identical or different, R2 represents a halogen atom, an alkyl radical containing from 1 to 5 carbon atoms, an alkoxy radical containing from 1 to 4 carbon atoms, an alkenyloxy radical containing from 3 to 4 carbon atoms, an alkynyloxy radical containing from 3 to 4 carbon atoms, an alkylthio radical containing from 1 to 4 carbon atoms, a halogenoalkyl radical containing from 1 to 4 carbon atoms, a halogenoalkoxy radical containing from 1 to 4 carbon atoms, a halogenalkylthio radical containing from 1 to 4 carbon atoms or a nitro, hydroxyl, cyano or benzyloxy radical and n is an integer which can be equal to 0, 1, 2, 3, 4 or 5, it being understood that, if n is greater than or equal to 2, the substituents R2 can be identical or different.
    公开号:SU938742A3
    申请号:SU802898701
    申请日:1980-03-26
    公开日:1982-06-23
    发明作者:Гиге Франсуа；Трэн Стефан
    申请人:Рон-Пуленк Агрошими(Фирма)；
    IPC主号:
    专利说明:

    593 under reflux for 1 h, then cool it down with a bath with a mixture of water and ice. 9.7 g of trichloroacrylic acid chloride are added dropwise to this solution, the temperature of which is maintained within 0-10 ° C, and the reaction mixture is kept under stirring at room temperature for 30 minutes. The reaction mixture is then poured into a mixture of 100 g of ice and 10 ml of concentrated sulfuric acid. After stirring the mixture for 1 h, the phase is decanted in toluene and the aqueous phase is extracted with 50 ml of toluene. The phases in toluene are combined, washed first with 100 ml of water, then with 100 ml of sodium bicarbonate solution and finally with 100 ml of water. After drying over anhydrous sodium sulfate and distilling off toluene, an oily liquid is obtained, which is heated in a partial vacuum under (vacuum 16 mm Hg) for 30 minutes, after which the residue is recrystallized from 200 ml of methylcyclohexane. Thus, 13 g of 2- (3-methylphenyl) -3-ethoxycarbonyl-5, 6-dichloro-pyrone having a melting point, corresponding to yield 79.5, are obtained. Elemental composition. Found,%: C 55.08; H 3.58; every 21.39. Calculated: С 55, Н 3.67; From 21.71. Example 2. The same operations are carried out in the same sequence as in Example 1, resulting in a compound. The chemical formulas of these compounds, as well as their physicochemical characteristics, are summarized in Table 1; in the column corresponding to R .., the numbers located in front of each of the substituents R, designation of the position of the substituent Rj. in the phenol cycle, which itself is in position 2 in the G-pyrone cycle.
    “Below 4
    about r- 1L
    .
    .1Л
    00% O lA L M

    incA 0%
    1L "8 t
    about X
    o

    u
    ""
    S
    u o
    Vi
    u o

    Kl

    about i
    Example 3 - In vitro study of fungicidal activity of compounds of general formula I.
    The effect of the compounds according to the invention on the fungal culture of PIricularia oryzae, causing rice piclariosis, was studied.
    The following operations were carried out in each of the individual tests. 5 ml of yellow gel (maltagar medium) were placed into each of the vessels for making experiments, after which the vessels were closed and sterilized for 20 minutes at. The vessels are placed in a water bath at 60 ° C. A certain amount of acetone solution (1%) of the test compound is injected into each vessel with a pipette in order to obtain a certain concentration on the culture, the concentration of this compound. After 2 hours, the vessels are inoculated with a syringe by injection with 0.5 ml of a spore suspension containing approximately 100,000 spores / ml. A vessel in which the agar medium does not contain the active ingredient is used as a comparative sample. The vessels were kept for 7 days at 2 ° C without illumination, after which the degree of development of the fungal disease in the vessels containing the tested active components was compared with the development of the disease in a comparative sample that did not undergo treatment. Also, for each of the tested compounds, a minimum dose was determined, allowing complete inhibition of the development of the fungal culture.
    This dose corresponds to: 0.2 g / l in the case of compounds I, 15, 18, 26 and 38; 0.1 g / l in the case of compounds 39Л1 and 42; 0.5 g / l for compounds 1.3. 6, 9 - 12, 17. 19, 27 29, 31 - З, 36, 37, 0. It is equal to or less than 0.01 g / l in the case of compounds 2, k, 5, 7, 8, 13, 17, 20 23, 30, 35, and ki.
    An example. Study of in vivo activity with respect to Plasmoraga viticola on grapes (preventive treatment).
    Grape (Gamai) plants grown in pots are sprayed from the inside of the leaves with an aqueous suspension of a wettable powder of the following composition,%:
    Test active substance 20
    Deflocculat nt (calcium lignosulfonate) 5 Humidifier (sodium alkylaryl sulfonate) 1 Carrier (aluminosilicate) 7
    in the appropriate dilution containing the active ingredient in the right dose. Each test is conducted three times.
    After 48 hours, the infection is carried out as a result of spraying on the inner leaf surface an aqueous suspension containing about 80,000 units / ml of Plasmopera viticola spores — a culture that causes mildew (a disease of grapes). The pots are then placed in a greenhouse for 48 hours, the relative humidity of which is 100, and the temperature is maintained at about.
    Control of the degree of disease of plants is carried out after 9 days. after infection.
    Under these conditions, there is observed the appearance of almost complete protection (more than 95%) in the case of given doses of the following proposed compounds: 0.015 g / l of compound 34; 0.06 g / l of Compound 1 and 35; 0.12 g / l of compound 31 and W 41; 0.25 g / l of compound 11, 18, 23, 33, 36-40.
    When used in the same dose (0.25 g / l), compounds 2–5, Yu, 12, 13, 15, 16, and 17 have a good protective effect (75–95%). In this experiment, any phytotoxicity phenomena were completely absent.
    Example 5 - In vivo activity test against Uromyce s phaseoli culture causing bean rust (preventive treatment).
    Bean plants are grown in 8 cm diameter pots filled with peat. At the growth stage, corresponding to the appearance of two seminal lobes, the plants are sprayed with an aqueous suspension of the same wettable powder as in Example 4, containing the test product in the required dose.
    After 48 hours, the beans are sprayed from a sprayer with a suspension of 21 spores (50,000 spores / ml) obtained from infected plants. Then the face is first placed in a greenhouse with 100% first in a greenhouse with a relative humidity and a temperature of 20 ° C for 8 hours, and then in a greenhouse in which the following conditions are maintained: 20-25 ° C Day temperature 15-20 ° C Night temperature Relative 70-80% humidity Control over the extent of damage is carried out on the day after infection when compared with a control sample that did not undergo treatment. 8 of these conditions, results were obtained indicating that, at a dose of 0.5 g, compounds L, 27, 30, 31, 35, Zb and 40 have almost full protective effects (over 95), and compounds 3 and 4 have good protective effects. (75-95). Example 6. In vivo activity test against Puccinia striiformis culture, which causes brown leaf rust of cereals (preventive treatment). Grains of wheat varieties of Joss sown in pots with a diameter of 8 cm. After 8 days. after sowing, neither the pots with wheat are treated by spraying from the sprayer an aqueous suspension of a wettable powder having the following weight composition,%: 2 - (- fluorophenyl) -3-ethoxycarbonyl-5, 6-dichloro-C-pyrone (compound 3) Lignosulfonate Calcium Alkylarylsulphonate Aluminosilicate Treatment is carried out using different concentrations of the active substance in an aqueous suspension, each test being repeated three times. After 48 hours after the treatment, the wheat is sprayed with the aid of the veterinarian’s bullets with a spore suspension (50,000 spores / ml) obtained from diseased plants. Then the wheat is placed in a greenhouse, the conditions in which correspond to Example 5. The control of the degree of damage is carried out on the 15th day after infection when compared with a control sample that has not been processed. Under these conditions, results were obtained indicating that, at a dose of 1 g / l, the compound was 222 and at a dose of 0.5 g / l, 0.250 g / l, and 0.125 g / l Compound 3 had a good protective effect (75 9b). In the course of this experiment, no signs of phytotoxicity were detected with respect to the treated plants. Example 7 Field trials of activity against Puccinia recondita culture, causing brown leaf rust of cereals. Wheat grains of the Nebraska variety are sown in the fall at experimental sites of 50 sq. M. On the 10th day of next year, wheat plants are processed by spraying pulp obtained by diluting a wettable powder with water with the following composition by weight: Test substance 500 Wetting agent (alkyl aryl sulfonate sodium) 10 Deflocculating agent (calcium lignosulfonate) 50 Counter-swelling agent (silica) 50 Media ( kaolinite) 390 This pulp contains 200 g / l of the active substance and is applied at a spray rate of 500 l / ha, which corresponds to a dose of 1000 g of the active substance per hectare. Each test is repeated k times. At the end of May, brown leaf rust has been noted. Secondary processing was carried out on June 7 using the same conditions that were maintained when processing 10 ma. Degree control was conducted on July 12th. At the same time, the (in;) surface of leaflets covered with brown leaf rust pustules was determined; the results obtained were compared with the results obtained in the case of the control area that was not processed. Under these conditions, results were obtained indicating that this percentage is on average 1.9 in the case of test plots treated with a composition containing compound 3, and 35. in the case of the control plot. Example 8. Field trials of activity in relation to the culture of Venturia inequalis, causing scab blon.
    23
    Experimental plots with an area of 30 sq. M., In which there are 5 blonds of the Golden Delicious variety, are treated on March 15 at the time of the occurrence of the disease with pulp obtained by diluting the same composition with water as in Example 7. This pulp contains 100 g / l of the active substance (compound 3) and is applied as a result of spraying at the rate of 1000 l / ha, which corresponds to a dose of 1 kg of the active substance per ta.
    Other test sites are treated the same day with pulp containing
    15 cent. The surface of the affected leaves.
    Example 9. Field trials of activity in relation to SeptdrTa ap culture and cephorus inducing septoriosis.
    Celery seedlings, a type of Genevile, were planted in experimental plots of 2 sq.m. On June 6, t icl at the same sites planted the diseased plants.
    The treatment was performed on August 7 and 23 using pulp obtained by diluting the same composition with water as in Example 7. This pulp contains 100 g / hl of the active substance and is applied by spraying. The preceding examples clearly illustrate significant fungicidal
    . 21
    syche.50 g / l of captan (N-trichloromethylmercaptotetrahydrophthalimide). This treatment is repeated in both cases under the same conditions as 5 and the first every 15 days, which corresponds to 6 treatments for each of the tested active compounds. Each test is repeated times. Several test sites, 10 not treated, were left as controls.
    The control over the degree of damage was carried out on 20 June, and the percentage of affected l was determined (1 st and 1% at the rate of 1000 l / ha, which corresponded to a BeTctsyeT dose of 1 kg / ha for the active substance.
    Other experimental sites were treated on the same days with a manebium at the rate of 2, kg / ha of active substance during each treatment. Several experimental sites that did not undergo treatment were used as controls.
    Control over the extent of damage was carried out on August 23, and the area (in%) of leaves affected by the disease was determined.
    权利要求:
    Claims (1)
    [1]
    properties of compounds of the general formula in relation to various types of fungi, in particular, basidomycetes (specifically - Puccima striiformis, Puceima recondita, Uromyces phascoli), ascomycetes (specifically - Ventu ris inequalis, fungi imperfecti (specifically - Piricularia orizae, Septorie apii), specifically, Plasmopara viticola), as well as a lack of activity in relation to the plants tested. Good results were also obtained for a variety of fungal seeds of the disease, for example, Fusarium nivale and Fusarium culmorum. Particularly good results were obtained when using the following dinene: 2- (4-fluorophenol) -3 ethoxycarbonyl-5, 6-dichloro-pyrone compound 3), 2- (3-trifluoromethylphenyl) -3-ethoxycarbonyl-5, 6 dichloro-pyro (compound 11). The doses in which the compounds are used can vary widely, depending on the degree of virulence of the fungi and on climatic conditions. In the General case, the compositions contain 0.01-5 g / l of the active ingredient. Good results are achieved. When used in practice, compounds of general formula I are rarely used in pure form. Usually they are an integral part of the compositions, which also fall within the scope of the invention and usually contain, besides the active component, the carrier and possibly the surfactant agent. The content of the active component in such compositions is usually in the range of 0.0005 - 95% weight .%. In the framework of the invention, the term carrier refers to an organic or inorganic product, natural or synthetic, with which the active substance is mixed in order to facilitate its use on plants, on grain or on soil, or to facilitate its transportation or operation. . This carrier is digestible to be inert and suitable for use in agriculture, specifically for use on plants. The carrier can be solid (clay, natural or synthetic silicates, resins, waxes, solid fertilizers, etc.) or liquid (water, alcohols, ketones, petroleum fractions, chlorine-substituted carbon dioxide, aromatic or paraffin hydrocarbons, liquefied gases and etc.). The surfactant may be an emulsifier, dispersing or wetting agent, having an ionic or non-ionic character. As examples, mention may be made of salts of polyacrylic, lignosulfonic, phenolsulfonic or naphthalenesulfonic acids, ethylene oxide polycondensates with fatty alcohols or with fatty acids, or with fatty amines, substituted phenols (specifically alkylphenols or arylphenols), salts of sulfonic acid, acidic acids, salts of esters of acidic acids, substituted phenols (specifically alkylphenols or arylphenols), salts of esters of sulfonic acids, substituted phenols (specifically alkylphenols or arylphenols), salts of sulfonyl esters, acidic acids, salts of esters of acidic acids, polyols, etc. alcohols or polyoxyethylene phenols. The compositions may also contain various other ingredients such as, for example, protective colloids, adhesives, thickeners, penetration agents, stabilizers, chelating organo-elemental compounds, etc., as well as other active ingredients that have pesticidal properties (specifically insecticides or fungicides), or plant growth accelerators (specifically, fertilizer). The compositions can be obtained in the form of wettable powders, soluble powders, powder for spraying, solutions, emulsifiable concentrates, emulsions, concentrated suspensions, aerosols. Wettable powders typically contain 20-95 ppm of active ingredient. In addition to solid carrier, they contain Ot5 wt.% Wetting agent, 310 weight. one or more stabilizers and / or other additives, such as penetration agents, adhesives or anticombing agents, dyes, etc. As an example, the weight composition of the composition of a wettable powder according to the invention is given, g: Active substance (compound 3) 5QO Calcium digosulfonate (deflocculate nt) 50 Isopropyl naphthalene sulfonate (anionic wetting agent) 10 Silica (antifouling agent) 50 Kaolin .390 Another example of a wetted powder according to The invention has the following composition by weight, g%: Active substance (compound 1) 700 Dibutyl naphthyl sodium sulfonate 50 Condensation product in a ratio of 3: 2: 1 naphthalene sulfonic acid, phenolsulfonic acid you and formaldehyde30 Kaolin 100 Chalk from Champagne 120 The third example of a wetted defect according to the invention corresponds to the following weight composition, g: Active substance 250 Equivorous mixture of chalk from Champagne and hydroxyethylcellulose 19 Sodium dibutylnaphthalene sulfonate 15 Silica 195 Chalk from Champagne 195 Cal. I can also be used in the form of powders for spraying, having, for example, the following weight composition, g: Active substance 50 Talc 950 Emulsifiable concentrates used as a result of spraying, contain t usually 10–50 wt./ab. of active ingredient and 2– .20 emulsifier. They may also contain, if necessary, 2–20 wt./ab. of suitable additives, such as surfactants, stabilizers, penetration agents. agents, and corrosion inhibitors, dyes, adhesives. As an example, the composition of an emulsifiable concentrate, g / l; Active substance (Compound 3) tOO Alkaline dodecylbenzenesulfonate Ionylphenol ethoxylated with 10 molecules of ethylene oxide 16 Cychexanone 200 Aromatic solvent Up to 1 l Suspended concentrates, so used by spraying, can be used in a manner that a stable, hasable body that has been put on a spray, to obtain a stable, colored, sprayable, according to the method that allows to get a sprayable material that can be used by spraying. ; they usually contain 10-75% of the weight of the active component, 0.5-15% of the weight of surface-active agents: 0.110 weightD of thixotropic agents, 010% weight,% of suitable additives, such as anti-foam agents, corrosion inhibitors, stabilizers, penetration agents and adhesives, and as a carrier, water or an organic liquid in which the active substance is practically insoluble; Some solid organic substances or mineral salts may then be dissolved in the carrier in order to either facilitate or impede sedimentation, or else to serve as anti-gel agents for water. The invention is a method for producing 2-phenyl-A-pyrone derivatives of the general formula O, Xg O, where X is a halogen atom; X is a hydrogen or halogen atom; R is an alkoxy group containing I-carbon atoms, an alkenyloxy group containing 3 carbon atoms, a propargyloxy group, a halogen-substituted alkyloxy group containing 1-i carbon atoms, a dialkylamino group in which each alkyl group is the same or different and contains -k y-hydrogen atom; Rj is a halogen atom or an alkyl containing 1-5 carbon atoms, an alkyloxy group containing -k carbon atoms, an alkenyloxy group containing 3- carbon atoms, a halogen-substituted alkyl containing 1-A carbon atoms, a nitro group or a benzyloxy group; n is an integer equal to 0, 1, 2 or 3, characterized by the benzylacetic derivative of the general formula J-c-CH -c-E WzV and n have the decree where R, parts, are reacted with a magnesium of the general formula CHC3) gMd. where R is alkyl C 4 in an anhydrous inert solvent at boiling to obtain a compound of the general formula n vy-c-cn-CM to r R and n have a decree where R, R values, 230 is reacted with di-or tri-halogenacrylic acid chloride Formulas About Xg nor CCC-Cl XT. have the indicated meanings; where X, and a halogen atom, in an environment of a non-aqueous inert solvent at 0-40 ° C, followed by cyclization of the resulting enol compound of the general formula,. "Wm the indicated values, by treating it with an aqueous solution of a strong acid, by separating the aqueous and organic phases, and by heating the organic phase by an SO-SC. Sources of information taken into account in the examination. USSR patent number, cl. C 07 O 309/38, 1975,
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    同族专利:
    公开号 | 公开日
    MA18788A1|1980-10-01|
    DE3060958D1|1982-11-25|
    EP0017602A1|1980-10-15|
    AR223867A1|1981-09-30|
    AU5681180A|1980-10-02|
    BG31478A3|1982-01-15|
    EP0017602B1|1982-10-20|
    OA06498A|1981-07-31|
    BR8001870A|1980-11-18|
    IL59608D0|1980-06-30|
    PL223044A1|1981-02-13|
    DD149891A5|1981-08-05|
    ES489964A0|1982-01-01|
    ES8206508A1|1982-01-01|
    FR2452487B1|1982-01-08|
    CU35252A|1982-08-24|
    FR2452487A1|1980-10-24|
    GB2046264A|1980-11-12|
    CS212344B2|1982-03-26|
    US4297367A|1981-10-27|
    AT1675T|1982-11-15|
    JPS55167286A|1980-12-26|
    GR67676B|1981-09-04|
    TR20293A|1981-01-07|
    ZA801763B|1981-03-25|
    PT71022A|1980-04-01|
    PT71022B|1981-06-25|
    DK131880A|1980-09-29|
    引用文献:
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    US4060533A|1976-06-25|1977-11-29|Sandoz, Inc.|Pyranone carboxamides|FR2494270B1|1980-11-14|1983-06-24|Rhone Poulenc Agrochimie|
    PH18960A|1981-06-03|1985-11-26|Ciba Geigy Ag|Novel 2--3--5,6-dihydro-4-pyrone derivatives,compositions containing them as active ingredients and the use thereof for combating weeds|
    US5250566A|1988-04-05|1993-10-05|Board Of Trustees Operating Michigan State University|Method for controlling nematodes|
    AU3419893A|1991-12-23|1993-07-28|Michigan State University|Method for controlling insects|
    AT128128T|1990-06-29|1995-10-15|Upjohn Co|ANTIATHEROSCLEROTIC AND ANTITHROMBOTIC 2- AMINO-6-PHENYL-4H-PYRAN-4-ONE.|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    FR7908569A|FR2452487B1|1979-03-28|1979-03-28|
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