• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    A new compound, named "Compound B-41D", has the formula: <IMAGE> and can be prepared by cultivating a microorganism of the genus Streptomyces, especially Streptomyces strain B-41-146. Compound B-41D has valuable acaricidal and anthelmintic activities.
    公开号:SU1011055A3
    申请号:SU802968603
    申请日:1980-08-22
    公开日:1983-04-07
    发明作者:Такигути @Е；Мисима Хироси；Ямамото Синдзиро；Терао Мития
    申请人:Санкио Компани Лимитед (Фирма)；
    IPC主号:
    专利说明:

    s
    The invention relates to microbiological washing and relates to the preparation of a substance with tick and anthelmintic activity. A known method for producing B-41 having an insecticidal and tick-borne activity, using Streptomyces B-il-H6 1. There is also a known method for producing a substance (milbenicine, which also has anthelmintic activity using the same product 2. However, the known methods do not provide the preparation of a substance of the formula bЪd 4Us HS HS. The purpose of this article is to obtain a wei-crea of formula I, which has anti-tick and anthelmintic activity. The goal is achieved by the fact that according to the method of obtaining a substance with anti-adhesive and anthelmintic activity of the formula I, Streptomyces 13-1-1 "b is expressed on a nutrient medium containing carbon sources water and nitrogen at 22 GP, with the subsequent separation of the target product from the culture fluid by concentration and purification. At the same time, cultivation was carried out (it was eluted on a medium containing glucose at a concentration of 6–8% as the main carbon source, maltose and / or maize starch at a concentration of 0, and as a source of nitrogen - a mixture of coarse soybean meal 0.5-1 and skim milk 1-2. In addition, concentration and purification are carried out until the content of the target product is 25-50. A substance with tick-borne and anthelmintic activity is obtained by cultivating the Streptomyces strain. This strain is deposited at the Fermentation Research Institute. Agencies of Industrial Sciences and Technology, Ministry of Foreign Trade and Industry, Japan, under the number, as well as under the name Bikoken-kinki 1 (CG. The strain is grown in a nutrient medium, (her sources of assimilable carbon and assimilable nitrogen). Carbon sources include glucose , sucrose, starch, glycerin, malt extract, moloza, and soya bean oil. The preferred carbon source is glucose, used in an amount of 6-8% (w / v, additional carbon sources — lactose, small Tozo and cr "hmal moisa in the amount of 0.5 to 2.0% C w / v ,. To maintain the pH at a constant level, excess glucose is added to the growth process. Nitrogen sources include coarse soy flour beans, wheat grains, meat extract, pentone, fresh yeast, steep maize liqueur, ammonium sulphate and ammonium nitrate. As a source of nitrogen, a mixture of coarse soybean flour 0,., 0% off milk 1, 0-2.0% If necessary, an amino acid (for example, glycine or arginine) is added to the culture medium. If necessary, inorganic salts are also added, such as calcium carbonate, sodium chloride, potassium chloride, or phosphates, other organic or inorganic materials can also be added that promote microbial growth and accelerate the formation of the substance. A high yield is obtained using a medium that contains 6–8% glucose, 0.5–2% lactose, and / or coarse soybean flour and 1.0–2.0% skim milk. The cultivation of the wasp is established under aerobic conditions at 22-3., Preferably at 28 ° C. The maximum productivity of the substance is reached after days after the beginning of the cultivation, which is carried out either with shaking or in a tank with a stirrer. The amount of the substance in the broth is determined as follows. A known amount, for example 3 g, of the culture broth, is poured into a small test tube, in
    31011
    which was added 10 ml of acetone. The mixture is then extracted with shaking and centrifuged. Acetone is added to the overhead solution to a total volume of 5 to 10 ml. The resulting solution is placed on a previously prepared place on a plate for thin-layer chromatography (silica gel, for example Kieselgel 6P F 25) in a quantity of, for example, 10-20 nl. The plate is then developed for 18 h with a 18:82 {vol. ) dioxane and tetra-. carbon chloride. The sample is examined using an is scanner or thin layer chromatography in a region with a wavelength of .45.
    The substance is isolated from the culture broth using a natural adsorbent (for example, activated carbon, aluminum dioxide or silica gel, a synthetic adsorbent (for example, Liaien HP-2PD absorbent (for example, Avitsel, ion exchange resin, ion exchange gel). filter.
    The isolation is carried out as follows.
    The fermentation broth is filtered using a filtration accelerator (such as diatomaceous earth) in order to obtain a filter cake, which is then extracted with methanol. Water is then added to the aqueous methane solution and the resulting solution is extracted with hexane. The hexane phase is separated and concentrated by evaporation under reduced pressure, resulting in the formation of an oily material containing the desired substance. This oily material is placed in a column containing silica gel (for example, Vakogel, G.-200) and eluted, for example, with a mixture of 95: 5 (Sb) hexane and acetone, in order to combine the fractions containing the desired substance. These fractions are concentrated by evaporation under reduced pressure, an oily material is again formed, which dissolves in a small amount of methanol, and added to a column of Sephadex H-20 material, then eluted with methanol. The fractions containing the desired material are collected, the solvent is removed and the residue is dissolved in a small amount of methanol. Water is added and the mixture is kept at room temperature.
    554;
    re. The result is a substance in the form of a foam or bubbles, KOTOpW after destruction gives an amorphous powder.
    After recrystallization from a mixture of 20: 1 (vol. Hexane and ethyl acetate, the substance is obtained as small needles with a melting point of 186-188 ° C. The procedure for purifying the substance can be carried out at any stage and use a crude product that contains the milbemycin mixture and the desired substance. If a mixture containing two or more of these substances is used without complete separation, it is sufficient that the resulting product gives 100 effect when used against ticks with a concentration of 5 ppm. The content of the substance in the crude product is preferably at least wt.%.
    The resulting substance has a high tick at application against adult mites and eggs, as well as anthelmintic activity.
    Substance mozhzt be applied against takihkleschey as spider mites two-spotted (Tetrahycniis urtrede), European red mite (Raponychus ulmi), the citrus red mite (Panonychus citri) and mites species Au lops or Aculus, which are parasitic on fruits, plants and flowers. The substance also has activity against ticks of the species 1x odidas doerma nyssidas and Sareopttdae, which parasitize animals. The substance also has high activity against ectoparasites such as Oestrus, Luci1 ha Hypoderma, Ctasurophilus, fleas, lice I, etc., as well as insects (such as cockroaches or flies and some other insects that are pests of the garden hosts such as tl and insect larvae of other Lepidoptera.In addition, the substance is active when applied against roundworms, such as worms of the species Meloidogyne, and ticks that inhabit the soil.
    When used against mites or insects, the preparation is preferably diluted with a carrier to form compositions such as powders, coarse powders, granules, fine granules, wettable powders, emulsifiable concentrates or an oil. 5 The carrier used to prepare such compositions may be synthetic or natural, inorganic or organic, and, in general, any carrier that is usually added to insecticides or acariids in order for the active ingredient to reach the object faster, which is processed (e.g., a plant, tick or insect pest), or to simplify storage, transport and handling of the active ingredient. Examples of their solid carriers are inorganic materials such as clay, diatomaceous earth talon, kaolin, bentonite, calcium carbonate or synthetic calcium silicate; natural or synthetic resins, such as coumarone, alkyd and polyvinyl chlorides; waxes such as palm and paraffin wax; walnut shells, such as walnut loops, or coarse soybean flour. Examples of suitable liquid carriers are water; alcohols, such as ethanol or isopropanol; glycols, such as ethylene glycol; glycol ethers such as ethylene glycol monophenyl ether or diethylene glycol monoethyl ether; ketones, such as acetone, methyl isobutyl ketone, cyclohexanone, acetophenone or isophorone; ethers, such as tetrahydrofuran or dioxane; aromatic hydrocarbons, such as benzene, toluene, xylene or methylnaphthalene) chlorinated hydrocarbons, such as trichloroethylene, and carbon tetrachloride; oil fractions having low, medium and high boiling points, containing kerosene, light petroleum products or aromatic hydrocarbons. The substance can be formulated as an aerosol, in which case the carrier can be fluorocarbons (including those known under the trade name Freon), liquefied non-volatile gas, dimethyl ether, and vinyl chloride monomer. If necessary, the compositions can also contain a surface-active agent with the purpose of emulsifying, dispersing, wetting or propagating the active compound, which can be either ionic or 55 "non-ionic material. Examples of suitable anionic surface-active agents can be whether sodium and calcium are ligno (. mono) sulfonic acids, sodium and potassium salts of oleic acid, sodium salt of lauryl (mono sulfonic acids and sodium salts and calcium dodecylbenzene {monosulfonic acids. Examples of suitable cationic surface-active agents include higher aliphatic amines and condensates of higher aliphatic amines with ethylene oxide. Examples of non-ionic surfactants include fatty acid glycerols, sucrose fatty acid layer ethers, ethylene oxide condensates with higher aliphatic alcohols, ethylene oxide with higher fatty acids; and ethylene oxide with alkylphenols or alkylnaphthols and copolymers of ethylene oxide with propylene oxide. In addition to the above, the prothioscleral or insecticidal compositions contain a protective colloid (such as gelatin, Arabic resin, casein, polyvinyl alcohol, or carboxymethyl cellulose J or a thixotropic agent (such as poly% osphate sodium or bentonite). The composition may also contain other compounds possessing anti-inflammatory or anti-thixotropic agent (such as poly% osphate sodium or bentonite). activity, for example, 2- (1-methylpropyl) -4, b-dinitrophenyl-f, &amp; -dimethyl acrylate, di- (p-chlorfereIl) -cyclopropylcarbonyl, N- (-chloro-2-methylphenyl) -N, N-dimethylformamine ; -2 ,,, 5-tetrachlorodiphenylsulfone; 1 , 1-bis- (p-chlorophenyl) -2,2, .- trichloroethanol; 2-sec-butylphenyl-M-methylcarbamate, m-tolyl-N-methylcarbamate or mineral oil, in some cases, to increase the activity of the composition; in In some cases, a synergistic effect can be expected. The substance can also be used in a mixture with other fungicides, herbicides, plant growth regulators, pest-attracting substances or fertilizers. The substance obtained in a known manner has activity against helminites in humans and animals and is used in the form of a drink. or caps ly. It can be applied as an aqueous solution or solution in other suitable non-toxic solvents or as a suspension or dispersion using accelerate 7. 101 levings of the suspension and wetting agents, bentonite, or other components. The drink should also contain an anti-foam agent. Preferably, the drink contains the active compound in an amount of 0.01-0.5 or 0.01-0.1% by weight. In addition, the substance can be applied in the form of dry solid capsules, pills or tablets containing a predetermined amount of the active compound. Such compositions can be prepared by blending and homogenizing mixing of the active compound with one or more finely divided materials, such as diluents, fillers, disintegrators, or binding agents (for example, starch, lactose, talc, magnesium stearate, or vegetable gums). The weight of the active ingredient can be varied over a wide range depending on the type of animal / which is processed, the degree of illness of the animal, and the body weight of the animal. The substance can be administered to animals evenly distributed in the feed or used in the form of balls. In order to achieve a satisfactory antiparasitic effect, the feed must contain an active compound in an amount of 0.00010, 02 weight .. The substance can also be dissolved or dispersed in a liquid carrier and administered parenterally to animals as an injection into the stomach, muscle, lungs or under the skin. When used as a parente, it is preferable to use vegetable oil, such as peanut or cottonseed oil. When administered parenterally, the active compound is contained in an amount of 0.0550% by weight of the total composition. The substance can be used topically, directly on an open skin area, for example, by spraying. Processing animals can be carried out in a short period of time, for example within 1-5 days. Example 1. Getting the substance. 600 ml of a previously prepared medium containing 2% w / v. glucose,}% flour of soybeans of coarse grinding, 0.5 saturated mums / liqueur and 0.21 sodium chloride, are placed in a Erlemeber flask with a capacity of 58 1 l. Colonies of the spore strain of Streptomyces. B-Ml-1 6 is grafted onto the above medium and then grown for CEH hours at. After this period of time has passed, the contents of two such 2 liter Erlenmeyer flasks are transferred to a fermenter equipped with a shaking device with a capacity of 30 liters, which already contains 20 liters of sterilized culture media containing k% w / v. glucose, 1 wt. / s, soybean flour large help, 0.5 wt./about. maize starch, 1 wt./about. With the addition of milk, 0,2% -ves. / about. saturated maize liqueur and 0.3 ml of sodium chloride. The pH value before sterilization is 7.2-7.5. Then the culture is incubated at 28 ° C with a pressure inside the fermentor of 0.5 kg / cm for 10 days. After completing this stage, 20 liters of broth for growing the culture is prepared to pH 3 by adding sulfuric acid, and then after adding 1 kg of Selite, auxiliary filtering material, the mixture is filtered under pressure, resulting in a filter cake weighing about 3 kg. Of this cake. extracted with 15L of methanol and the extract filtered. The 15 liters of methanol solution thus obtained are diluted with 5 liters of water and extracted with 20 liters of hexane. The resulting hexane solution was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure in a water bath at which resulted in the formation of 22 g of an oily material. The resulting oily material is dissolved in 30 ml of hexane and adsorbed on a column containing 2 kg of silica gel, balanced with hexane. The column was ejected with a mixture of hexane and acetone 95: 5 (06.). The 2l volume fraction containing the desired compound is collected and then concentrated under reduced pressure in a water bath at + 0-5 s, resulting in the formation of 550 mg of an oily material. This material is dissolved in 1 ml of methanol and the solution is placed in a column containing 200 ml of Sephadex LH-20, which is balanced with methanol. The column is then eluted with methanol, resulting in a b5 ml fraction containing the desired substance. This fraction was concentrated by evaporation under reduced pressure, and the resulting residue was dissolved in 2 ml of methanol and the methanol solution was diluted with 2 ml of water. The mixture was kept at room temperature, resulting in 110 mg of the compound as an amorphous powder. Example 2. Preparation of a substance In a 2-liter flask containing bOOML of a previously prepared medium containing% (weight, / v) sugar, 0.35% (w / v) polypeptone, and 0.05 (" its./about.) dikaliartofata, inoculate the colonies of the spore strain of Streptomyces strain and then the microorganisms are grown for 8 at. The contents of these three flasks are then transferred to a fermentation tank with a tank capacity that contains 300 l of a thoroughly sterilized culture medium, which contains 8% w / v glucose, 1 w / o coarse soybean flour, 0.5 w / o maize starch, 1 w / o removed milk, 0.2 w / o saturated maize liqueur, 0.3% w / o sodium chloride and 0.05% w / o calcium carbonate. The pH of the medium is maintained at 7,, 5. The cultivation is carried out at 28 ° C with stirring at a speed of 150,200 rpm and an internal pressure of 0.5-1.0 kg / cm-for 12 days. After this stage is completed, the amount of the substance in the medium is 180 µg / ml. In 300 l of the resulting culture medium, the pH is provided at a level of 3 by adding sulfuric acid, and then 15 Celite, a filter aid, is added to the mixture, and the mixture is filtered with pressure, resulting in a kQ filter cake. kg This pellet is extracted with 200 l of methanol and filtered. 150 liters of water are added to the methanol extract and the mixture is extracted twice, both times with 250 liters of hexane. The resulting hexane solution was dried over anhydrous sodium sulphate and then concentrated by evaporation under reduced pressure in a water bath at, resulting in 350 g of oil. This oil is dissolved in lOO ml of hexane and adsorbed on a column containing 3 kg of silica gel, which is pre-balanced with hexane. The column is eluted with a mixture of hexane and acetone 95: 5 vol. resulting in a fraction of the eluate containing the desired substance. This fraction is concentrated by evaporation under reduced pressure over a water bath at 045 ° C, resulting in 33 g of crude crystals. The obtained crystals are dissolved in a mixture of hexane and ethyl acetate 20: 1 (vol., From which, as a result of recrystallization, 17 g of the substance are obtained as colorless needle crystals that melt at 186-188 ° and have the previously described properties. Example 3. Powder. 10 parts by weight of the substance in the form of amorphous powder Ds are added and thoroughly mixed with 5 parts by weight of white carbon. 50 parts by weight of clay are added to this mixture.The mixture is thoroughly mixed, ground three times. in a mill of fine grinding of the shock type, and then again thoroughly mixing powder is produced. Example k. Wettable powder. 0 parts by weight of the substance is mixed in the form of amorphous powder with .0 weight of white carbon. To the mixture is added 5 parts by weight of sodium dodecylbenzenesulfonate, 2 weight; part of polyvinyl alcohol and 33 parts of clay; the resulting mixture is thoroughly mixed. Next, the mixture is ground three times in an impact grinding mill, thoroughly mixed again, and a wettable powder is obtained. Example 5. Emulsifiable concentrates. 3 weight.h. substances in the form of amorphous powder, 7 weight.h. polyoxyethylene nonylphenyl ether, 3 parts by weight Calcium dodecylbenzenesulfonate and 87% by weight of xylene are stirred and filtered, resulting in a solution that can be used as an emulsifiable concentrate. EXAMPLE 6 Oil Based Composition 10 weight.h. substances in the form of an amorphous powder are dissolved in 10 parts by weight. xylene and then added to the solution
    11101
    80 wt.h..machine oil. Next, the mixture is filtered, resulting in an oil-based composition,
    PRI mme R.7. The anti-mite activity regarding the double-spotted spider mite (Tetranychus urtlcae),
    3% by weight of the substance is emulsified, the concentrate is prepared as in Example 3. Then the concentrate is diluted with water to obtain the concentration of the active compound, which is listed in Table. 1, On the foliage of Chinese cowpea, containing adult females of Tetranychus urtlcae, spray the test solution in an amount; 5 cm by 2 sheets using spray.
    105512.
    Mizuho type glitter. Farther than the foliage, it is airborne and kept under conditions of fatigue at 2 ° C for 72 hours, after which
    S number of dead glues. This number is 30-35 per sheet; two sheets are used for each test.
    1§: The experiment is carried out using the presumed substance, and in the control experiments, neither lubemycins and eu and the well-known agricultural preparation Keltan (based on 1,1-bis (chlorophenyl) -2,2, 2-trichloroethanol L) are used. The obtained results are presented in Table 1.
    Table 1
    Example 8. Tick-borne activity relative to the eggs of two muddy spider mites (Tetra-nychus urticae).
    In this test, eggs were laid at the age of 1 day of Tetranychus urticae, which were previously applied to the leaves of Chinese cowpea. Leaf about | battered by the substance obtained
    by the proposed method as well as by the substances given in example 7. The number of eggs on one sheet is about 100. After 2 weeks. after processing, the number u1 | that are not hatched is determined.
    The results are given in Table 2, where the percentages of the total number of eggs are indicated. ..
     table 2
    citrus red mite (Panonychus citri). The test was carried out as in Example 7, except that in addition to the results shown in Table 2. 3, an experiment was conducted with a Kelta-25 emulsion at a concentration of 30 ppm, but even at such a concentration, the death of the tick is only 93.
    From the above results it can be seen that the proposed substance possesses a highly significant anti-tick activity compared to milbemycins c (. Io (which, in turn, have a significantly higher activity compared to the known anti-acaricide drug Keltan.
    PRI me R 10. Helminthicum against Nematospiroides ubris.
    Male mice at the age of weeks. RFVL species, whose weight is 18-22 g, are infected with the tomato method. parasite Via Nematospiroides dubius. The mice are then divided into groups of five animals each, and each mouse receives a feed containing the proposed substance in the amount indicated in Table. k, for 7 days after infection, and then they are given unprocessed food again. After 1 day after. 50 infected animals are euthanized and the number of parasites in the small intestine is determined. The result is compared with a control group that undergoes a similar infection procedure, Ss but does not receive the proposed substance.
    The results of anthelmintic activity are given in table. .
    adult female citrus red mite. The results are shown in Table. 3
    T a
    faces
    Table k
    0.05
    100
    0,005
    100
    96
    0.0005
    0.03
    32

    27.6 0.03
    The data table. k show that the proposed substance has anthelmintic activity, which is about 2 times higher than the activity of the milbemycin mixture.
    PRI me R 11. Anthelmintic activity against Tochosaga cati.
    18 cats of 13 males and 15 females weighing about 1.6-3.0 kg, which are naturally infected with the parasite Tochosaga cati, are used as animals. Each kitten in the dental method is administered a single dose of a substance dispersed in olive oil in the following amounts: 2 cats there — 5 mg / kg, 3 cats there — 2.5 mg / kg, 2 cats there / kg. 3 cats there - 0.5 mg / kg, 3 cats there - 0.25 mg / kg, 2 cats there 0, 1 mg / kg and 3 cats there - 0.05 mg / kg. Before treatment, the NGF index (i.e., the number of eggs per 1 g of feces) is 15016250. After 1 week of treatment, the same indicator is zero for all cats, and the total number of ejected worms during the same week is 2–10. As a result, the autopsy revealed that no one kitten has worms. Example 12. Antihelmintic activity against Tochosaga canis. As animals, 13 puppies (3 males and 10 females) weighing 1.2–13 kg are used, which naturally are infected with the parasite Tochosaga canis .: Each puppy is administered a single dose of a substance dispersed in olivine oil in the following way quantities: 1 puppy - 5 ug / kg animal weight; 2 puppies - 0.25 mg / kg, puppies - 0.1 mg / kg, 3 puppies - 0.05 mg / kg, 2 puppies - 0.025 mg / kg and 1 puppy - 0.01 mg / kg. Before administering the drug, the IGC index is lOO-ioo iOO. After 1 week after treatment, the same indicator for all puppies is zero, and the total number of expelled worms during the same week is 2-36 for each puppy. As a result, the autopsy found that no puppy has worms. ; Example 13. Antihelmintic activity against Trichuris vulpis. 5 dogs (2 females and 3 males) weighing 6.2-11.5 kg at the age of 2 or 3 years are used as animals. A single dose of 1 or 5 mg / kg iaieca of animal substance in the form of a capsule coated with gelatin is administered to each animal by the dental method. It has been established that these dogs are naturally infected with the parasite Trichurls vulpus. Before processing, the NGF index is 100-3500. One week after treatment, the same indicator is 0–200, and the total number of worms expelled during the week is 8–451. As a result of the dissection, it was established that the number of remaining parasites is 0-33., I.e. the effectiveness of the drug 92-100. An example is Sho Glistagonna activity against Ancylostoma canium. As animals, 5 dogs are used (2 females and 3 males weighing 7.0-11.5 kg at the age of 2 or 3 years. These dogs are naturally infected with the parasite Ancylostoma canium. Each dog is administered a single oral dose of a capsule substance. coated with gelatin. The substance is administered to dogs in the following amounts: 2 dogs - 0.5 m- / kg, animal weight; 2 dogs - 1 mg / kg and 1 dog - 5 mg / kg. Before administration of the compound, the IGC indicator 200-1550. After 1 week after treatment, the same indicator for all dogs is zero, and the total number of expelled worms during A week is about t-82 per dog. As a result of the dissection, it has been found that no dog has any worms. The proposed method allows to obtain a substance with a high pro-tick and anthelmintic activity.
    权利要求:
    Claims (3)
    [1]
    1. The method of obtaining substances with anti-mite and anthelmintic activity of the formula characterized in that the strain Streptomyces B = 41 = 146 is grown on a nutrient medium containing carbon and nitrogen sources at 22-30 ° C, followed by isolation of the target product from the culture fluid, concentration and purification.
    [2]
    2. The method according to p. 1, characterized in that the cultivation is carried out on a medium containing glucose at a concentration of 6-8% as the main carbon source and an additional carbon source - lactose, maltose and / or maize starch at a concentration of 0 , 5 _ 2% and, as a source of nitrogen, a mixture of coarse-ground flour soybeans 0.5-1% and skim milk 1-2%.
    [3]
    3. The method of pop. ^ characterized in that the concentration and purification is carried out to the content of the target product 25-50%.
    SS01I01ns “
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    同族专利:
    公开号 | 公开日
    FR2463773A1|1981-02-27|
    AU574695B2|1988-07-14|
    CH645899A5|1984-10-31|
    ES8106177A1|1981-06-16|
    DE3031756C2|1989-11-23|
    BR8005337A|1981-03-04|
    GB2056986B|1983-10-19|
    ES494435A0|1981-06-16|
    US4346171A|1982-08-24|
    NL8004791A|1981-02-25|
    IL60861D0|1980-10-26|
    MX6259E|1985-02-18|
    GB2056986A|1981-03-25|
    IT1209436B|1989-07-16|
    AU6166880A|1981-03-05|
    AU536200B2|1984-04-19|
    IT8068315D0|1980-08-25|
    NZ194742A|1982-12-07|
    DE3031756A1|1981-03-12|
    IL60861A|1983-09-30|
    HU189473B|1986-07-28|
    JPH0217555B2|1990-04-20|
    AU3081484A|1984-11-08|
    JPS5632481A|1981-04-01|
    FR2463773B1|1984-02-24|
    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    JP54107550A|JPH0217555B2|1979-08-23|1979-08-23|
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